Valbiom Julieroiz Technicalandmarketsurvey July20121348649987

Author: Julie Roz, roiz@valbiom.be, +32 81 62 23 50.
ValBiom Gembloux Agro-Bio Tech Universit de Lige

Document FARR-Wal - Avec le soutien de la Rgion wallonne DGO3
Rf. 2012_JR_05

Biolubricants: technical and market survey
January 2012 July 2012

PATENT: new patents on biolubes (C10M) since January 2012.....01-14
TECHNICAL SIDE: whats new from labs?...15-50
LCA...................................................................................................................../
POLICY..51
LEGISLATION.../
ON THE WEB................................................................................................52-59
ECO-LABELS IN EUROPE...60-62

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01-- PATENT: ESTER OILS
Publication number: WO2012024808 (A1)
Publication date: 2012-03-01
Inventor: LAEMMLE PATRICK [CH]; WALTERSPIEL BERNARDO [CH]; WOYDT MATHIAS
[DE]
Applicant: PANOLIN AG [CH]; LAEMMLE PATRICK [CH]; WALTERSPIEL BERNARDO [CH];
WOYDT MATHIAS [DE]
Category: C10M105/36; C10M105/38
According to a first aspect, an ester oil, in particular for producing a hydraulic fluid
and/or a lubricant, containing an esterification product from the esterification of at least
one monoalcohol with at least one polycarboxylic acid, is characterized in that the
monoalcohol and/or the polycarboxylic acid originates from renewable raw materials.
According to a second aspect, an ester oil, in particular for producing a hydraulic fluid
and/or a lubricant, containing an esterification product from the esterification of at least
one monocarboxylic acid with at least one dialcohol, is characterized in that the dialcohol
and/or the monocarboxylic acid originates from renewable raw materials.

02-- PATENT: VEGETABLE OIL OF HIGH DIELECTRIC PURITY, METHOD FOR
OBTAINING SAME AND USE IN AN ELECTRICAL DEVICE
Patent number: US2012061629 (A1)
Inventor: PULIDO SANCHEZ ALBERTO JOSE [MX]; URZUA HERNANDEZ CARLOS MANUEL
[MX]; CAZARES MENDEZ SERGIO FRANCISCO [MX]; VILLARREAL RIOS JERONIMO R
[MX]; CONTRERAS DE LEON JOSE EULALIO [MX]; GUERRA ZUBIAGA DAVID APOLINAR
[MX]
Applicant: /
Category: C10M101/04; H01B3/20
A dielectric high purity vegetable oil-free from antioxidants and/or external additives to
be used in electric equipment such as transformers, as isolating element and as cooling
means and a method for obtaining the same in which the dielectric high purity vegetable
oil-is obtained by means of the optimization of the bleaching steps-and deodorizing-from
the Refining process-known as Modified Caustic Refining Long-Mix (RBD).

03-- PATENT: LUBRICANT ADDITIVES
Inventor: BLOOM PAUL [US]
Applicant: ARCHER DANIELS MIDLAND CO [US]
Category: C10G3/00; C10M129/70; C10M145/22
Processes are described for producing liquid, biobased lubricant additives containing from
50 to 100% biobased carbon according to ASTM D6866 from heat-bodied oils by
transesterification with biobased or petroleum based alcohols and by hydrotreatment of
at least the resulting diesters, triesters and polyesters.

04-- PATENT: BIOLUBRICANT ESTERS FROM THE ALCOHOLS OF UNSATURATED
FATTY ACIDS
Patent number: MX2011013133 (A)

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Inventor: MILLER STEPHEN JOSEPH [US]; ELOMARI SALEH; ZHOU ZHEN
Applicant: CHEVRON USA INC [US]
Category: C07C29/10D4; C07C29/147; C07C67/08; C07C69/30; C10M129/74
The present invention is generally directed to triester-based lubricant compositions. The
present invention is also directed to methods of making these and other similar lubricant
compositions. In some embodiments, the methods for making such triester-based
lubricants utilize a biomass precursor comprising mono-unsaturated fatty acids, wherein
such mono-unsaturated fatty acids are reduced to mono-unsaturated fatty alcohols en
route to the synthesis of triester species for use as/in the triester-based lubricant
compositions. Subsequent steps in such synthesis may employ carboxylic acids and/or
acyl halides/anhydrides derived from biomass and/or Fischer-Tropsch synthesis.

05-- PATENT: SYNTHESIS OF BIOLUBRICANT ESTERS FROM UNSATURATED
FATTY ACID DERIVATIVES
Patent number: MX2011013030 (A)
Inventor: MILLER STEPHEN JOSEPH [US]; ELOMARI SALEH A; ZHOU ZHEN
Applicant: CHEVRON USA INC [US]
Category: C07C29/132; C07C29/147; C07C67/08; C10M105/38; C11C3/00; C11C3/12
The present invention is generally directed to diester-based lubricant compositions
comprising one or more isomeric mixtures of diester species. The present invention is
also directed to methods of making these and other similar lubricant compositions. In
some embodiments, the methods for making such diester-based lubricants utilize a
biomass precursor material from which mono-unsaturated free lipid species can be
provided or otherwise generated, wherein such mono-unsaturated free lipid species are
converted to isomeric diol species en route to the synthesis of diester species for use
as/in the diester-based lubricant compositions.

06-- PATENT: STABILISER AND ADDITIVE COMPOUND FOR COMBUSTION
ENGINES
Patent number: CH703950 (B1)
Inventor: SCHAEFER VOLKER DR [DE]; BOTZ OTTO HEINRICH [CH]
Applicant: NATOIL AG [CH]
Category: C10M129/00; C10M141/06
Use of stabilizer composition comprising (A) at least one epoxidized natural oil and/or
fatty acid ester (a1) and (a2) at least one epoxidized natural fatty acid glyceride, as
component (A) with a sterically hindered phenol as component (B), for the stabilizing
crude oil, at least partially refined oil or synthetic esters, is claimed. An independent
claim is included for an additive composition comprising the components (A) and (B).

07-- PATENT: LUBRICANT FOR POWDER METALLURGY
Inventor: RAPP LINDENAU RENE [DE]; WIMBERT LARS [DE]
Applicant: /
Category: B22F1/00A4N; C04B35/632; C10M105/38; C10M105/40; C10M169/04

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A lubricant for use in a powder mixture is disclosed. This lubricant contains carnauba wax
and at least one plant- or animal-based fat. A powder mixture using this lubricant can be
used to compact green parts have higher densities and helps to improve the life of the
tools compacting the powder.

08-- PATENT: CONVERSION OF VEGETABLE OILS TO BASE OILS AND
TRANSPORTATION FUELS
Patent number: WO2012030646 (A2)
Inventor: MILLER STEPHEN J [US]
Applicant: CHEVRON USA INC [US]; MILLER STEPHEN JOSEPH [US]
Category: C10G3/00; C10G45/58; C10G50/00; C10G57/02; C10G65/04D; C10G69/12P;
C10L1/08; C10L1/16B; C10M101/00; C10M105/04; C10M107/10; Y02E50/13.
The present invention is directed to methods (processes) and systems for processing
triglyceride-containing, biologically-derived oils to provide for base oils and transportation
fuels, wherein partial oligomerization of fatty acids contained therein provide for an
oligomerized mixture from which the base oils and transportation fuels can be extracted.
Such methods and systems can involve an initial hydrotreating step or a direct
isomerization of the oligomerized mixture.

09-- PATENT: NON-AQUEOUS LUBRICANT AND FUEL COMPOSITIONS
COMPRISING FATTY ACID ESTERS OF HYDROXY- CARBOXYLIC ACIDS, AND
USES THEREOF
Inventor: WEST KEVIN RICHARD [GB]
Applicant: CASTROL LTD [GB]; WEST KEVIN RICHARD [GB]
Category: C10L1/19; C10L1/19F; C10L10/08; C10M129/70; C10M129/76; C10M129/78
The use as an anti-wear additive and/or friction modifier in a non-aqueous lubricant
composition and/or in a fuel composition of at least one long chain fatty acid ester of a
hydroxy carboxylic acid in which the long chain fatty acid has at least 4 carbon atoms
and the ester is an oil-soluble ester of a mono- or poly- hydroxy carboxylic acid having 1
to 4 groups which are independently carboxylic acid groups or lower hydrocarbyl esters
thereof and in which, when the hydroxy carboxylic acid is a mono-hydroxy carboxylic
acid, the ester has a long chain fatty acid ester moiety of the hydroxy group of the
hydroxy carboxylic acid and, when the hydroxy carboxylic acid is a poly-hydroxy
carboxylic acid, the ester has independently long chain fatty acid ester moieties of one or
two of the hydroxy groups of the poly-hydroxy carboxylic acid. Also, a non-aqueous
lubricant composition and a fuel composition for an internal combustion engine which
comprises at least one of said long chain fatty acid esters.

10-- PATENT: ASYMMETRIC ESTERS OF FATTY ACIDS USEFUL AS LUBRICANTS
Patent number: EP2444388 (A1)
Inventor: GARCIA COLOMER ALBERT [ES]; GRANERO TORNE FRANCESC [ES]; BELTRAN
GIRALT LLUIS [ES]; PLANAS SAUTER ANTONI [ES]
Applicant: IND QUIMICA LASEM S A [ES]
Category: C10M105/42; C10M129/78

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Composition comprising at least one ester of one or more saturated C 18 fatty acids and
an alcohol, wherein the fatty acids have between 1 and 3 pairs of vicinal ester groups of
formula R 1 COO-, the two vicinal ester groups in each pair being different, R 1 is a
radical independently selected from linear or branched (C 1 -C 18 ) alkyl; and the alcohol
is selected from the group consisting of a (C 1 -C 15 ) linear or branched monohydric
alcohol and a (C 2 -C 6 ) polyhydric alcohol having between 2 and 4 hydroxyl groups
obtainable by a process comprising: a) epoxidizing a product comprising at least an ester
of an unsaturated C 18 fatty acid and of an alcohol; followed by ring opening of the
epoxide and b) reacting the compound obtained in step a) with a (C 1 -C 18 ) linear or
branched carboxylic acid different from the one used in step a). The composition
obtainable by the process of the invention is useful as lubricant base stock oil or as an
additive to modulate the viscosity and/or the pour point of lubricant compounds.

11-- PATENT: ALKOXYLATED CARBOHYDRATE ESTERS AND THEIR USE
Inventor: MAINX HANS-GEORG [DE]; HOFER PETER [DE]; BUSCH STEFAN [DE];
MAHNKE EIKE-ULF [DE]
Applicant: COGNIS IP MAN GMBH [DE]
Category: C07C67/03; C07H13/06; C10M105/38
Suggested are new adducts of on average 1 to 80 moles ethylene oxide and/or propylene
oxide to esters of carbohydrates selected from the group consisting of dextrose,
saccharose, maltose and maltotriose.

12-- PATENT: ENVIRONMENTALLY-FRIENDLY LUBRICANT COMPOSITIONS
Inventor: MACPHERSON IAN [US]; PETTIGREW ANN [US]
Applicant: AFTON CHEMICAL CORP [US]
Category: C10M161/00; C10M171/00
A lubricant additive composition having environmentally compatible characteristics as
defined by European Council Directive 67/548/EEC is disclosed. Such a composition may
include components selected from non-persistent materials, non-bioaccumulative
materials, or non-toxic materials.

13-- PATENT: ESTOLIDE DERIVATIVES PREPARED FROM TRIGLYCERIDES
Inventor: NAIR SREEJIT [IN]; KAUJALGIKAR SAURABH [IN]; VINCI DANIELE [BE]
Applicant: DOW GLOBAL TECHNOLOGIES LLC [US]; NAIR SREEJIT [IN]; KAUJALGIKAR
SAURABH [IN]; VINCI DANIELE [BE]
Category: C10M105/42
A process to prepare an estolide derivative composition comprises reacting a triglyceride
having an unsaturation level of less than 0.1 m Eq/g and an alcohol having from 2 to 22
carbon atoms, under conditions such that a product including an oligomerized ester
having residual hydroxyl groups is formed; and reacting the product with a capping agent
under conditions such that an estolide derivative composition is formed. The
compositions may exhibit desirably low pour point, desirable viscosity and thermoxidative

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stability, and a high level of renewable carbons, making them suitable for use as
biolubricants, process fluids, plasticizers, or starting materials for polyurethane polymers.

14-- PATENT: MODIFIED VEGETABLE OIL LUBRICANTS
Inventor: ENECKE HERMAN PAUL [US]; GARBARK DANIEL B [US]; VIJAYENDRAN BHIMA
RAO [US]; CAFMEYER JEFFREY [US]
Applicant: BATTELLE MEMORIAL INSTITUTE [US]
Category: C10M105/42; C10M109/02; C11C3/00; C11C3/04
Lubricants based on renewable feedstocks and methods of making them.

15-- TECHNICAL SIDE: MICROWAVE-BASED MANUFACTURING FOR LOWER-COST
BIOBASED LUBRICANTS AND CHEMICALS: THE DEVELOPMENT OF MICROWAVE-
BASED PROCESSES FOR MANUFACTURING BIOBASED GREASE IS REVIEWED,
AND THE ECONOMIC IMPACT THESE PROCESSES COULD HAVE IS PRESENTED
(REVIEW)
International News on Fats, Oils and Related Materials
Volume 23, Issue 6, June 2012, Pages 388-394
L. Honary
A new technique to heat oil, based on the same principle as the household microwave
oven, could be used to manufacture biobased greases efficiently and with less danger of
fire.

16-- TECHNICAL SIDE: MICROWAVE BARREL REACTOR USE IN
TRIMETHYLOLPROPANE OLEATE SYNTHESIS BY CANDIDA ANTARCTICA LIPASE
IN A BIPHASIC NON-SOLVENT PROCESS
Green Chem., 2012, Advance Article
Publication date 30 May 2012
Manuel Happe, Pascal Grand, Sbastien Farquet, Sandrine Aeby, Jean-Claude
Hritier, Franois Corthay, Eric Mabillard, Roger Marti, Ennio Vanoli, Alain-
Franois Grogg, Samuel Nussbaum, Alain Roduit, Franois Tiche, Sam Salem,
Carole Constantin, Esther Schmitt, Silvan Zahno, Christoph Ellert, Ahmed Habib,
Julien Wyss and Fabian Fischer
A novel microwave barrel reactor (MBR) was constructed and used in lipase catalyzed
biolubricant synthesis. The MBR is thought as a versatile process tool for
biotransformation and green chemistry that overcomes current size limitations in
microwave reactors. A lipase mediated biotransformation in the MBR was compared to a
state of the art jacketed reactor with external heat exchanger. Oleic acid and
trimethylolpropane converted quantitatively (96%) into biolubricants using microwave
induction. The heat dissipation in the MBR was analyzed by thermal imaging and inside
thermometry. Conversion rates, rate constants and pseudo reaction orders were in line
with conventional processing and no microwave effect was detected. The MBR is a
versatile new reactor for non solvent, minimal and common solvent processing in the
microwave field. While the subject of investigations was biolubricant synthesis in the
MBR, the technology described is of wider potential interest in the field of biomass
processing and sustainable chemical manufacture.

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17-- TECHNICAL SIDE: SYNTHESIS OF TRIMETHYLOLPROPANE ESTERS WITH
IMMOBILIZED LIPASE FROM CANDIDA SP. 99-125
Journal of Molecular Catalysis B: Enzymatic
Volume 74, Issue 3-4, February 2012, Pages 151-155
Tao, Y. , Chen, B. , Liu, L. , Tan, T.
The lubricants of the future have to be more environmentally adapted, have a higher
level of performance. Synthesis esters (SEs) which can be used as raw materials for
biodegradable lubricant base oils are increasing in popularity due to superior technical
properties. Direct esterification of trimethylolpropane (TMP) with fatty acid in a solvent
free system, by immobilized lipase from Candida sp. 99-125 was studied. Investigations
of important factors were carried out involving temperature, time, enzyme amount,
substrates molar ratio and water content. For 2 g caprylic acid, under the optimal
conditions, with 0.4 g immobilized lipase, at substrates molar ratio 1:10 (TMP to acid),
temperature 40 C and water content controlled under 0.8% (w/w), the total conversion
of fatty acid with TMP reached up to 96% and the formation of trisubstituted TMP esters
reached 93%. Water content controlled during esterification process was found to be
critical for high yield of direct esterification.

18-- TECHNICAL SIDE: PRODUCTION OF CHEMOENZYMATIC CATALYZED
MONOEPOXIDE BIOLUBRICANT: OPTIMIZATION AND PHYSICOCHEMICAL
CHARACTERISTICS
Journal of Biomedicine and Biotechnology
Volume 2012, 2012, Article number 693848
Salimon, J. , Salih, N. , Abdullah, B.M.
Linoleic acid (LA) is converted to per-carboxylic acid catalyzedby an immobilized lipase
from Candida antarctica (Novozym 435). This per-carboxylic acid is only intermediate
and epoxidized itself in good yields and almost without consecutive reactions.
Monoepoxide linoleic acid 9(12)-10(13)-monoepoxy 12(9)-octadecanoic acid (MEOA) was
optimized using D-optimal design. At optimum conditions, higher yield (82.14) and
medium oxirane oxygen content (OOC) (4.91) of MEOA were predicted at 15L of H2O2,
120mg of Novozym 435, and 7h of reaction time. In order to develop better-quality
biolubricants, pour point (PP), flash point (FP), viscosity index (VI), and oxidative
stability (OT) were determined for LA and MEOA. The results showed that MEOA
exhibited good low-temperature behavior with PP of - 41 C. FP of MEOA increased to 128
C comparing with 115 C of LA. In a similar fashion, VI for LA was 224 generally several
hundred centistokes (cSt) more viscous than MEOA 130.8. The ability of a substance to
resist oxidative degradation is another important property for biolubricants. Therefore, LA
and MEOA were screened to measure their OT which was observed at 189 and 168 C,
respectively.

19-- TECHNICAL SIDE: NATURAL AND SYNTHETIC ANTIOXIDANT ADDITIVES
FOR IMPROVING THE PERFORMANCE OF NEW BIOLUBRICANT FORMULATIONS
J Agric Food Chem.
2011 Dec 28;59(24):12917-24. Epub 2011 Dec 1.
Quinchia LA, Delgado MA, Valencia C, Franco JM, Gallegos C.
Knowledge of the oxidative stability of vegetable oils for lubricant applications is a key
point, because vegetable oil oxidation potential is the main disadvantage for its use as a
lubricant. Oil degradation after an oxidation process can seriously affect its lubricating

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function and increase wear. In this work, two different methods for evaluating the
oxidation stability of lubricating vegetable oils, the oxidation onset temperature,
characterized through DSC measurements (ASTM E 2009-08), and the pressure drop in
the oxygen pressure vessel (ASTM D 942-02), have been used. Additionally,
thermogravimetric analysis and FTIR studies have also been carried out. High-oleic
sunflower (HOSO) and castor (CO) oils were selected and blended with natural ((+)--
tocopherol (TCP), propyl gallate (PG), l-ascorbic acid 6-palmitate (AP)) or synthetic
antioxidants (4,4-methylenebis(2,6-di-tert- butylphenol) (MBP)), with the aim of
formulating biodegradable vegetable-based lubricants according to REACH
regulation.(1)The results showed that the most effective biodegradable antioxidant is PG,
comparable to MBP, whereas lower effectiveness was obtained for TCP and AP. In relation
to the methods tested, DSC measurements achieve accurate data more quickly for
evaluating the oxidation stability of these basestocks, showing a linear correlation with
the traditional method based on the oxygen bomb test. The empirical equation obtained
depends on the mechanism involved in the antioxidant activity.

20-- TECHNICAL SIDE: FULLERENE C 60 AS AN INHIBITOR OF HIGH
TEMPERATURE LIPID OXIDATION
Carbon
Volume 50, Issue 10, August 2012, Pages 3943-3946
Czochara, R., Ziaja, P., Piotrowski, P., Pokrop, R., Litwinienko, G.
Non-isothermal oxidation of a model saturated lipid (stearic acid) in the bulk phase in the
presence of fullerene C 60 at concentrations of 1-8 mM was monitored by differential
scanning calorimetry in order to determine the kinetic parameters that describe the
global first order oxidation process. The activation energies, pre-exponential factors, and
rate constants calculated by the Ozawa-Flynn-Wall method for the first detectable
exothermic effect of oxidation, indicate the antioxidant behavior of C 60 over a wide
range of temperatures that makes it a non-corrosive agent effectively increasing the
oxidative stability of lubricants and biolubricants.

21-- TECHNICAL SIDE: POLYSULFIDE AND BIOBASED EXTREME PRESSURE
ADDITIVE PERFORMANCE IN VEGETABLE VS PARAFFINIC BASE OILS
Industrial and Engineering Chemistry Research
Volume 51, Issue 1, 11 January 2012, Pages 262-273
Biresaw, G. , Asadauskas, S.J., McClure, T.G.
Twist compression tribotester (TCT) and 4-ball extreme pressure (EP) methods were
used to investigate commercial polysulfide (PS) and biobased polyester (PE) EP additives
in paraffinic (150N) and refined soybean (SOY) base oils of similar viscosity. Binary
blends of EP additive and base oil were investigated as a function of additive
concentration. In addition to weld point (WP), 4-ball EP produced a set of preweld data,
notably peak torque and wear scar diameter, which were found to correlate with WP
results. TCT gave a 5-fold larger time-to-failure (TTF) for neat SOY than for neat 150N,
whereas 4-ball EP gave similar WP (120 kgf) values for both neat oils. This difference
was explained by invoking boundary contribution to TCT but not to 4-ball EP method.
Both additives improved the WP and TTF of the base oils, which further increased with
increasing additive concentration. However, the extent of the improvements was highly
dependent on the chemistries of the additive and base oil of the blends. Thus, at similar
concentrations, the WP of PE was higher in the 150N than in the SOY base oil, while the

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WP of PS was higher in the SOY than in the 150N base oil. Similarly, TTF of 150N was
higher with blended PE than PS; whereas for SOY, it was higher with blended PS than PE.
This chemistry effect was attributed to relative compatibility between EP additives and
base fluids. The results suggest that a substantial reduction (up to 4-fold) in EP additive
usage in commercial lubricant formulations can be achieved through proper selection of
compatible base fluids and additives.

22-- TECHNICAL SIDE: TRIBOLOGICAL STUDY OF BORON-CONTAINING
SOYBEAN LECITHIN AS ENVIRONMENTALLY FRIENDLY LUBRICANT ADDITIVE IN
SYNTHETIC BASE FLUIDS
Tribology Letters
2012, DOI: 10.1007/s11249-012-9994-8
Li, W., Wu, Y., Wang, X. , Liu, W.
Environmentally friendly boron-containing soybean lecithin (BSL) was synthesised.
Constant temperature and humidity box was applied to evaluate the hydrolytic stability of
the novel lubricant additive. The friction-reducing, anti-wear, and extreme pressure
performance of BSL in synthetic base fluids were studied by an optimol SRV-I oscillating
reciprocating friction and wear tester and four-ball tester. The hydrolytic resistance test
results reveal that BSL possesses good hydrolytic stability. Tribological tests show that
the friction-reducing performance of BSL in A51 is inferior to PAO10. The incorporation of
BSL in synthetic basestock can dramatically reduce the wear volume of the lower steel
disc under different test conditions. BSL can also enhance the load-carrying capacities of
the synthetic base fluids. Morphology and chemical composition of the wear surface were
characterized by scanning electron microscope and X-ray photoelectron spectroscopy.
The results indicated that excellent tribological performance of the BSL can be attribute
to the formation of chemisorption and chemical reaction protecting films composed of Fe
2O 3, iron polyphosphates, organic amines, and BN, etc.

23-- TECHNICAL SIDE: STUDY ON VISCOSITY MODIFIERS FOR BIODEGRADABLE
ESTER BASED LUBRICANTS (NOTE)
NLGI Spokesman
Volume 76, Issue 2, May 2012, Pages 33-34
Vargo, D.M., Devore, D.A.
The compatibility between several polymers and ester oils, e.g., synthetic ester and
vegetable oils, were studied. The relationship between the structure of the polymer and
the ester and their solubility characteristics in the ester oil was investigated. The ester
oils include typical synthetic esters, e.g., mono ester, adipate ester, phthalate ester,
tnmellitate ester, polyol ester, and trimethylopropane ester, and natural esters, e.g.,
soybean oil, canola oil, and castor oil. Mutual compatibility required similarities in
structure of the polymer and the base oil, e.g., the presence of double bonds and/or the
presence of ester functionality. Polymers that contain ester functionality, e.g., alkyl-
diester copolymer copolymers and polymers that contain double bonds, e.g.,
polybutadiene were the most soluble in various synthetic ester and vegetable base oils.

24-- TECHNICAL SIDE: TRIBOLOGICAL BEHAVIOR OF SOME LONG-CHAIN
DIMERCAPTOTHIADIAZOLE DERIVATIVES AS MULTIFUNCTIONAL LUBRICANT
ADDITIVES IN VEGETABLE OIL AND INVESTIGATION OF THEIR
TRIBOCHEMISTRY USING XANES

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Tribology Letters
Volume 45, Issue 3, March 2012, Pages 465-476
Chen, H. , Yan, J., Ren, T. , Zhao, Y., Zheng, L.
A series of novel long-chain dimercaptothiadiazole derivatives are prepared and used as
antiwear (AW) and extreme pressure (EP) additives in vegetable oil, and their tribological
performance is tested by using a four-ball tester. In order to understand the friction
process further, X-ray absorption near edge structure spectroscopy is adopted to analyze
the chemistry of tribofilms under AW/EP regime, and meanwhile thermal films are also
considered for comparison. These derivatives are capable in improving the tribological
characteristic of the base stock, and disubstituted derivatives are more effective than
other derivatives. Though disubstituted derivatives and disubstituted polysulfur
derivatives all fail in improving tribological performance at 0.1 wt%, they are still helpful
at other additive concentrations. All these long-chain thiadiazole derivatives, in particular
the disubstituted polysulfur ones, are good at improving the EP characteristic of the base
colza oil. Thermal films generated from these derivatives are composed of ferrous sulfate
and a small amount of adsorbed organic sulfide. During the heating process, these long-
chain derivatives easily undergo thermal oxidation to generate high-valent sulfate on the
metal surface. Ferrous sulfide is the main component of tribofilms generated by these
derivatives, while ferrous sulfate in these films almost vanishes at 1.0 wt%. These long-
chain derivatives tend to react with metal surface to generate low-valent sulfide under
rubbing conditions. On the other hand, ferrous sulfide is also the main component of EP
films generated by monosubstituted derivatives and disubstituted polysulfur derivatives
at 1.0 wt%. But the EP films formed by disubstituted derivatives are composed of ferrous
sulfide and ferrous sulfate.

25-- TECHNICAL SIDE: A SEARCH FOR ECOFRIENDLY DETERGENT/DISPERSANT
ADDITIVES FOR VEGETABLE-OIL BASED LUBRICANTS
Journal of Surfactants and Detergents
2011, Pages 1-11
Singh, A.K. , Singh, R.K.
Carbonaceous deposits in automotive engines are the major problems associated with oil
aging. Efficient detergents and dispersants have been used for several decades to solve
this problem particularly in petroleum oils. But future lubricants and new engine
hardware require development of new nontoxic detergent/dispersant additive
technologies. Environmental concerns limit the formulation of the future lubricants. It
requires not only the base oil to be ecofriendly but the additives also. In the present
work, some of the potential ecofriendly chemical's molecules were identified. Specific
detergents applications along with effects of chemical modifications were evaluated by
Blotters Spot and Panel Coker Tests. Among the studied compounds, the PIB
(polyisobutylene) succinimides are showing promising results at lower temperature, while
at higher temperature piperazine derivatives citrate and oleate have the best potential to
be develop as ecofriendly detergent/dispersant additives.

26-- TECHNICAL SIDE: EVALUATION OF PALM OIL METHYL ESTER AS
LUBRICANT ADDITIVE USING MILLING AND FOUR-BALL TESTS
International Journal of Mechanical and Materials Engineering
Volume 6, Issue 3, December 2011, Pages 374-379
Dayou, S., Liew, W.Y.H. , Ismail, M.A.B., Dayou, J.

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This paper examines the effectiveness of POME (palm-oil methyl ester) as lubricant
additive based on the results obtained in the four-ball and milling tests. The results
produced in the four-ball tests showed that small amount of POME as an additive in the
mineral oil resulted in shorter running-in period, lower steady-state friction coefficient
and degree of adhesion, and higher weld load. The presence of POME enhanced the
effectiveness of the mineral oil in suppressing coating delamination and delaying the
occurrence of cracking and fracture on the flank face of the tool during milling of stavax
(modified 420 stainless steel). The results obtained in the four-ball tests suggested
that this was due to a reduction in the cutting forces and lesser degree of welding of
asperities brought about by the presence of POME.

27-- TECHNICAL SIDE: APPLICATION OF ECLS AND TODAYS LEGISLATION
Journal of ASTM International
Volume 9, Issue 1, January 2012
Laemmle, P. , Rohrbach, P.
Environmentally considerate lubricants (ECLs)-the so called "bio oils"-were introduced in
the mid 80s to minimize impact of lubrication on the environment. In the early 1990s the
German RAL (Blue Angel) and the Swedish Standard organisations defined corresponding
specifications for ECLs, other Eco-Labels followed. In 2005 the European Community
released the directive 2005/360 defining the toxicity and ecotoxicity profile for ECLs,
which qualifies them for the Euro-Marguerite. For more than 20 years top tier ECLs were
used in mobile and stationary hydraulic equipment.Well documented field experiences
not only demonstrate these lubricants contribute to the fulfillment of the new laws but
also meet technical requirements for this equipment. In this paper important EC
Directives related to lubricants and the protection of the environment are discussed and
how they are implemented into national laws. In addition the benefits of ECL in hydraulic
equipment are addressed.

28-- TECHNICAL SIDE: PHYSICAL PROPERTIES STUDY ON PARTIALLY BIO-
BASED LUBRICANT BLENDS: THERMALLY MODIFIED SOYBEAN OIL WITH
POPULAR COMMERCIAL ESTERS
International Journal of Sustainable Engineering
5 (1), 2012, 33-37
Doll, K. M., Sharma, B. K.
Thermally polymerised soybean oil (SBO) is compared with several other vegetable oils,
including ordinary SBO and high-oleic SBO (HO SBO). Acid values (AVs) and kinematic
viscosities of the oils were measured over 28 days on oils stored at 85C. As expected,
the AVs and viscosities increased with time and the HO SBO demonstrated similar but
smaller effects. The thermally modified oil was not better than ordinary SBO
necessitating the need for an optimised blending strategy. Lubricant blends were
prepared by mixing thermally modified SBO with a series of compatible ester-based
synthetic fluids. These displayed oxidative stabilities, by pressurised differential scanning
calorimetry, similar to the bio-based oil. Furthermore, the kinematic viscosity and pour
point of the lubricant blend could be accurately controlled by careful tuning of the blend
ratio.

29-- TECHNICAL SIDE: EVIDENCE CONTRARY TO THE ACCEPTED DIELS-ALDER
MECHANISM IN THE THERMAL MODIFICATION OF VEGETABLE OIL

Rf. 2012_JR_05
JAOCS, Journal of the American Oil Chemists' Society
Arca, M., Sharma, B.K., Price, N.P.J., Perez, J.M., Doll, K.M.
A fatty methyl ester product has been made using two routes. Soybean oil was thermally
polymerized anaerobically without a catalyst at 330 C and the material was then
transesterified using base catalyst and methanol. Alternatively, a similar product can be
obtained by heating methyl linoleate to the same temperature in a pressure reactor. The
product structure was studied by NMR spectroscopy, gel permeation chromatography and
mass spectrometry. It is a dimeric product which does not contain substituted
cyclohexane structures. This evidence shows that the Diels-Alder reaction has not
occurred under these conditions. This is in contradiction to many literature reports, but in
agreement with a neglected paper from 1971. This correction has implications in both
biodiesel and industrial oil products.

30-- TECHNICAL SIDE: ELASTOHYDRODYNAMIC STUDY OF BLENDS OF BIO-
BASED ESTERS WITH POLYALPHAOLEFIN IN THE LOW FILM THICKNESS REGIME
JAOCS, Journal of the American Oil Chemists' Society
Bantchev, G.B. , Biresaw, G. , Cermak, S.C.
The film thickness in elastohydrodynamic (EHD) conditions for soybean oil (SBO), oleic
estolide ester (EST) and their binary blends with polyalphaolefins (PAO2 or PAO40) were
studied at 30 and 100 C. Changes with time, for up to 200 min, were monitored. SBO
and its blends with the lower viscosity PAO2 showed initially good agreement with the
Hamrock-Dowson (H-D) equation down to 1-3 nm film thickness. 60 min or more after
the start of the measurements, boundary layers with thickness up to 4.7 nm were
observed. The blend of SBO with the more viscous PAO40 showed initially a good
agreement with H-D at 100 C. Negative deviations in film thickness were observed 15
min after the start of the measurements. At extended periods of time, up to 200 min,
they were less pronounced but still detectable. EST-PAO2 blend showed initially
formation of boundary layers with thickness around 2 nm. The boundary layer at 30 C
did not change for 200 min, while at 100 C showed a decrease in thickness and/or
viscosity with time. The EST and the EST-PAO40 blends showed good agreement with the
H-D equation and did not display a boundary or fractionation layer within 200 min.

31-- TECHNICAL SIDE: EXPERIMENTAL EVALUATION OF REFINED, BLEACHED,
AND DEODORIZED PALM OLEIN AND PALM STEARIN IN COLD EXTRUSION OF
ALUMINUM A1050
Tribology transactions
2012, vol. 55, no2, pp. 199-209
Syahrullail, S., Kamitani, S., Nakanishi, K.
The performance of palm oil as a lubricant in a cold metal forming process was tested
and evaluated by carrying out plane strain extrusion experiments and experimental
analyses using a visioplasticity method. In the present research, two types of refined
palm oil, refined, bleached, and deodorized (RBD) palm olein and RBD palm stearin, were
tested as lubricants. The workpiece material was aluminum JIS-A1050. The experiments
were carried out at room temperature (22C). Paraffinic mineral oils with varying degrees
of viscosity were tested for comparison. The experiment used an extrusion apparatus in
which the taper dies were facing together, with zero frictional constraint at the contact

Rf. 2012_JR_05
plane (corresponding to the plane plate tool) conducted, and results were compared with
those extruded with lubricants. Extrusion load and surface roughness of the billets were
measured and compared. The distribution of the material flow velocity and effective
strain in the exit zone of the billets were calculated using the visioplasticity method, and
these data were also compared. The results confirmed that RBD palm olein and palm
stearin provide sufficient lubrication performance in the cold work metal forming process.

32-- TECHNICAL SIDE: LOW-TEMPERATURE FLOW BEHAVIOUR OF VEGETABLE
OIL-BASED LUBRICANTS
Industrial Crops and Products
Volume 37, Issue 1, May 2012, Pages 383388
Quinchia, L. A., Delgado, M. A., Franco, J. M., Spikes, H. A., Gallegos, C.
Low temperature performance is one of the main constraints concerning the use of
vegetable oils as lubricants, more than mineral or synthetic oil-based lubricants. In this
work, the low-temperature behaviour of a variety of vegetable oil basestocks for
lubricating applications, as well as their blends with some viscosity improvers and pour
point additives, was studied through pour point determinations, thermal analysis (DSC)
and viscosity measurements at low temperature. The concentration of polyunsaturated
fatty acids (PUFAs) was found a predominant parameter influencing the low-temperature
properties of vegetable oil-based lubricants. The pour point depressant (PPD) additives
used had a positive influence by lowering the pour point and increasing the low-
temperature performance of the vegetable oils studied, which was found dependent on
vegetable oil fatty acid composition. In this sense, the most striking result was shown by
the sunflower (SO)/PPD blend, whose pour point temperature reached -36C in
comparison to -18C for the neat oil. By contrast, the worst result was obtained for the
high oleic sunflower oil (HOSO)/PPD blend (-21C) in comparison with HOSO (-18C). On
the other hand, it was found that the ethyl cellulose (EC), used as viscosity modifier,
induces a delay in HOSO crystallization, producing a similar effect than PPD tested,
besides increasing the viscosity. However, the ethylene-vinyl acetate copolymer (EVA)
induces an undesirable increase in HOSO viscosity at around 13C.

33-- TECHNICAL SIDE: TRIESTER DERIVATIVES OF OLEIC ACID: THE EFFECT OF
CHEMICAL STRUCTURE ON LOW TEMPERATURE, THERMO-OXIDATION AND
TRIBOLOGICAL PROPERTIES
Volume 38, Issue 1, July 2012, Pages 107-114
Salimon, J. , Salih, N. , Yousif, E.
Due to the strict regulations imposed on mineral oil-based lubricants because of their
non-biodegradable wastes, the development and applications of biolubricants are
increasing daily. Plant oils are being investigated as a potential source of environmentally
favorable lubricants because of their biodegradability, renewability, viscosity-temperature
relationship, low volatility and excellent lubrication performance. However, the use of
plant oils has some restriction, the most critical being oxidative stability and low-
temperature problems. This paper presents systematic modifications to improve the
physicochemical and tribological properties of plant oil derivatives. Thin-film micro-
oxidation testing and pressure differential scanning calorimetry were used to compare
the thermo-oxidative stabilities. The results showed that among the oleic acid-based
triester compounds, 2-ethylhexyl 9-(myristoxy)-10-(heptanoyloxy)octadecanoate (9) had

Rf. 2012_JR_05
the lowest pour point (-47.19 C) while 2-ethylhexyl 9-(caprooxy)-10-
(heptanoyloxy)octadecanoate (5) had the highest onset temperature (103.10 C) and the
lowest amount of volatile loss and insoluble deposits at 89.17% and 78.51%,
respectively. Overall, the data indicate that the biolubricant basestocks based on this
chemical modification offer great potential for the development of industrial products.

34-- TECHNICAL SIDE: EFFECTS OF BLENDED VEGETABLE-BASED CUTTING
FLUIDS WITH EXTREME PRESSURE ON TOOL WEAR AND FORCE COMPONENTS
IN TURNING OF AL 7075-T6
Lubrication Science
Article first published online: 25 JUN 2012. Early View (Online Version of Record
published before inclusion in an issue)
Kuram, E., Ozcelik, B. , Huseyin Cetin, M., Demirbas, E., Askin, S.
In this study, performances of four different types of vegetable-based cutting fluids
(VBCFs) over a commercial mineral cutting fluid were evaluated for machinability of Al
7075-T6. Lubrication properties of VBCFs were improved with additive of extreme
pressure. Cutting force and tool wear data were obtained for performance analyses of
cutting fluids during longitudinal turning of Al 7075-T6. Cutting, feed and radial forces
indicated 1.70-38.25% improvements for VBCFs over the commercial mineral cutting
fluid. The lowest average values of flank and nose wears obtained with blended cutting
fluid containing 12% of extreme pressure were 0.09 and 0.10mm, respectively, whereas
these values for the commercial mineral cutting fluid were 0.18 and 0.15mm. The
scanning electron microscope results showed adherence of workpiece material occurred
on rake and flank faces, and flank and nose wears were the dominant wear modes. It
was found that performances of VBCFs during turning of Al 7075-T6 were better than
that of the commercial mineral cutting fluid.

35-- TECHNICAL SIDE: TRIBOLOGICAL PROPERTIES OF NON-FERROUS COATING
LUBRICATED WITH RAPESEED OIL CONTAINING LUBRICANT ADDITIVES
Lubrication Science
Article first published online: 18 JUN 2012. Early View (Online Version of Record
published before inclusion in an issue)
Xin Feng, Yanqiu Xia
With the increasing requirements of environmental protection, using lead, hexavalent
chromium and other heavy metals will be prohibited in different surface coatings. In this
paper, the non-ferrous CrN coatings and the rapeseed oil were chosen as friction pair and
biodegradable lubricant. The tribology properties were investigated using SRV-IV
reciprocating friction wear test. The worn surface of CrN coatings was observed and
analysed using scanning electron microscopy and X-ray photoelectron spectroscopy. The
results indicate that the rapeseed oil containing 1wt.% MoZn (MoDTC (molybdenum
dithiocarbamate)+ZnDTP (zinc dithiophosphate) (1:3)) exhibits better friction-reducing
properties than the rapeseed oil containing 1wt.% PN (an amine salt of an
alkoxylphosphate) additives, whereas the rapeseed oil containing 1wt.% PN additive
exhibits better wear resistance properties than the rapeseed oil containing 1wt.% MoZn
additives. This is partly attributed to the tribophysical and tribochemical reactions
between the lubricant and the CrN coating sliding surfaces.

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36-- TECHNICAL SIDE: LUBRICATION MECHANISMS OF LAMELLAR FATTY ACID
FLUIDS
Tribology Letters
Fay, H., Cayer-Barrioz, J., Mazuyer, D., Mondain-Monval, O., Ponsinet, V.,
Meeker, S.
The lubrication mechanisms of different lamellar fluids are investigated as they are
introduced in the thin contact zone between two macroscopic surfaces in motion in a
friction measurement set-up. We simultaneously measure the film thickness and its
lubricative properties under controlled contact kinematics. The lamellar phases consist of
nanometric flat bilayers of fatty acid surfactant molecules organized in periodic stacks
separated by a water/ethylene diamine solution. First, we examine the film forming
capability of these phases when the two surfaces are moving at the same velocity, i.e. in
''pure rolling'' conditions. We observe the growth of a thick film in the contact which
eventually reaches a stable value. The relatively high viscosity of the film leads to a
situation of so-called ''starved lubrication''. By modelling the film build-up process, we
determine the viscosity of the lubricant and its piezoviscosity. As shear is applied
between the surfaces, the lubricant film exhibits a constant thickness and a rather low
frictional response. We correlate this behaviour to the combination of a relatively high
viscosity value together with a low piezoviscosity. Through the addition of a hydrophobic
liquid (naphthenic oil) to the initial system, we increase the bilayer thickness whilst
keeping the lamellar characteristic packing distance constant. This changes both the film
forming capability and frictional behaviour of the lamellar fluid. We propose a model to
account for the observed friction responses of both lamellar phases and discuss the shear
localization in the lubricant film.

37-- TECHNICAL SIDE: SURFACE-ENHANCED RAMAN SPECTROSCOPY OF
TRIBOCHEMICALLY FORMED BOUNDARY FILMS OF REFINED AND UNREFINED
CANOLA OILS
International News on Fats, Oils and Related Materials
Chua, W. , Chapman, P., Stachowiak, G.W.
The paper reports the investigation of tribochemically formed boundary films of canola
oils using surface-enhanced Raman spectroscopy. This is the first time that metallic
surfaces lubricated by plant oils have been studied using this technique. The results of
this work provided strong evidence that fatty acids were liberated from the triglyceride
structure during sliding to form a fatty acid soap layer on the silver surface. The study
also revealed that the fatty acid chains of the unrefined canola oil were more disordered
and most likely in a gauche conformation, while that of the refined canola oil were tightly
packed and oriented perpendicular to the surface. It is believed that the greater presence
of polar minor components in the unrefined oil, such as phospholipids, interfered with the
ability of free fatty acids to form a tightly packed monolayer on the silver surface.

38-- TECHNICAL SIDE: HOW FRIENDLY ARE BIO-BASED GREASES WITH OTHER
GREASES? (NOTE)
NLGI Spokesman
Volume 76, Issue 2, May 2012, Page 18
Kumar, A., Mallory, B.

Rf. 2012_JR_05
Advances in bio-based fluids and their additive chemistries have considerably improved
the quality and performance of these lubricants, bringing it at par to mineral oil-based
greases. The compatibility of lubricating greases is an important property that plays a
crucial role at the manufacturing stage and in end use application. Compatibility studies
of various greases based on different thickeners have been carried out. However, the
compatibility charts available are based on thickener types and the role of base oil on
compatibility is not clearly defined. In light of this, the compatibility of aluminum
complex and lithium complex greases prepared in canola oil was studied with different
types of mineral and synthetic oil based greases. The bio-based greases covered were
based on canola oil only. The canola oil greases examined were with and/or without
additives.

39-- TECHNICAL SIDE: IMPROVEMENT OF POUR POINT AND OXIDATIVE
STABILITY OF SYNTHETIC ESTER BASESTOCKS FOR BIOLUBRICANT
APPLICATIONS
Arabian Journal of Chemistry
Volume 5, Issue 2, April 2012, Pages 193-200
Salimon, J. , Salih, N., Yousif, E.
For environmental reasons, as well as the dwindling source of petroleum, a new class of
environmentally acceptable and renewable biolubricants based on plant oils is available.
Even though plant oils possess excellent lubricant-related properties, there are some
concerns about using it as biolubricant base oil. In this study we present a series of
structures derived from oleic acid to be used as synthetic biolubricant basestocks.
Measuring of pour point (PP), flash point, viscosity index (VI), oxidation onset
temperature (OT) and signal maximum temperature (SMT) was carried out for each
compound. Furthermore, the friction and wear properties were measured using a high-
frequency reciprocating rig (HFRR). The resulting product structures were confirmed by
NMR and FTIR spectroscopic analysis. The results showed that ethylhexyl 9-
(octanoyloxy)-10-(behenoxy)octadecanoate with behenyl mid-chain ester exhibited the
most favorable low temperature performance (PP -48. C) and ethylhexyl 9-
(octanoyloxy)-10-(octyloxy)octadecanoate octyl mid-chain ester exhibited higher
oxidation stability (OT 142. C) than the other synthetic ester oils. On the other hand,
the highest ball wear scan diameter was obtained for ethylhexyl 9-(octanoyloxy)-10-
(behenoxy)octadecanoate while the lowest value was obtained for 9-hydroxy-10-
octyloxyoctadecanoic acid. Overall, it was concluded that these synthetic ester oils have
potential in formulation of industrial fluids for different temperature applications.

40-- TECHNICAL SIDE: SYNTHETIC BIOLUBRICANT BASESTOCKS BASED ON
ENVIRONMENTALLY FRIENDLY RAW MATERIALS
Journal of King Saud University Science
In Press, Corrected Proof, Available online 24 February 2011
Nadia Salih, Jumat Salimon, Emad Yousif
This work outlines modifications in the epoxidation, oxirane ring opening, esterification
and acylation reactions to produce oleic acid based triester derivatives. Measuring of pour
point (PP), flash point (FP), viscosity index (VI), oxidation onset temperature (OT) and
signal maximum temperature (SMT) was carried out for each compound. The resulting
product structures were confirmed by NMR and FTIR spectroscopic analysis. The results
showed that butyl 9-(decanoyloxy)-10-(behenoxy)octadecanoate with bulky ester

Rf. 2012_JR_05
behenyl mid chain exhibited the most favorable low-temperature performance (PP 47
C). On the other hand, butyl 9-(decanoyloxy)-10-(octyloxy)octadecanoate exhibited
higher oxidation stability (OT 173 C) than the other synthetic esters. In conclusion, an
increase in mid chain substituent length improves the PP and conversely lowers the OT.

41-- TECHNICAL SIDE: ASSESSMENT OF BIODEGRADABILITY AND OXIDATION
STABILITY OF MINERAL, VEGETABLE AND SYNTHETIC OIL SAMPLES
Advanced Materials Research
Volumes 455-456, pp 1182-1188
Bo Wu, Chang Lu Wang, Ya Qiong Liu, Dong He, Mian Hua Chen, Yu Rong Wang,
Feng Juan Li
A castor oil-based detection method for the analysis of biological degradation was
established on the base of CEC-L-33-A-93 test method and the domestic conventional
experimental methods. Difference of the test samples between the experimental and
published values was less then 0.50%. Maximum error of degradation rate was 1.92% in
parallel experimental. Compared to the domestic conventional methods, degradation rate
obtained by the improved analysis methods of castor oil-based is approximately higher
than 5.0%. Meanwhile, analysis and detection method of DIOS with advantage of high
accuracy, conveniency and good reproducibility is established and showed stability by
studying the correlation of parallel samples that the coefficient of variation is less than
5%.

42-- TECHNICAL SIDE: SYNTHESIS, CHARACTERIZATION AND
PHYSICOCHEMICAL PROPERTIES OF OLEIC ACID ETHER DERIVATIVES AS
BIOLUBRICANT BASESTOCKS (NOTE)
Journal of Oleo Science
Volume 60, Issue 12, 2011, Pages 613-618
Salimon, J. , Salih, N. , Yousif, E.
Petroleum is a finite source as well as causing several environmental problems. Therefore
petroleum needs to be replaced by alternative and sustainable sources. Plant oils and
oleochemicals derived from them represent such alternative sources; the use of
oleochemicals as biobased lubricants is of significant interest. This article presents a
series of chemical modification on oleic acid to yield synthetic biolubricant basestocks.
Measuring of density, volatility, cloud point (CP), pour point (PP), fl ash point (FP),
viscosity index (VI), onset temperature (OT) and signal maximum temperature (SMT)
was carried out for each compound. Furthermore, the friction and wear properties were
measured using high-frequency reciprocating rig (HFRR). The results showed that
octadecyl 9-octadecyloxy-10-hydroxyoctadecanoate exhibited the most favorable low-
temperature performance (CP -26C, PP -28C) and the lowest ball wear scan diameter
(42 m) while propyl 9-propyloxy-10-hydroxyoctadecanoate exhibited the higher
oxidation stability (OT 156C).

43-- TECHNICAL SIDE: FRICTION AND WEAR CHARACTERISTICS OF WASTE
VEGETABLE OIL CONTAMINATED LUBRICANTS
International Journal of Mechanical and Materials Engineering
Volume 6, Issue 3, December 2011, Pages 431-436
Kalam, M.A. , Masjuki, H.H., Varman, M., Liaquat, A.M.

Rf. 2012_JR_05
In this paper, a four-ball tribotester was used with standard test method IP-239 to
evaluate friction and wear characteristics of normal lubricant, additive added lubricant
and waste vegetable oil (WVO) contaminated lubricants. The balls used in four-ball
tribotester were based on carbon-chromium steel ball bearings. The results obtained to
present friction and wear characteristics are coefficient of friction (), wear scar diameter
(WSD), flash temperature parameter (FTP), viscosity index (VI) and total acid number
(TAN). Each test was conducted for five different loads from 50 kg to 90 kg with an
interval of 10 kg. The lubricant was contaminated with WVO from 1% to 5%. The normal
lubricant (as sample A) was used for comparison purposes. The test results showed that
WVO contaminated lubricants with suitable anti-wear additive can reduce wear and
friction coefficient. The objective of this investigation is to develop a new lubricant based
on waste palm oil (such as WVO).

44-- TECHNICAL SIDE: KINETIC STUDY OF JATROPHA BIOLUBRICANT FROM
TRANSESTERIFICATION OF JATROPHA CURCAS OIL WITH
TRIMETHYLOLPROPANE: EFFECTS OF TEMPERATURE
Volume 38, Issue 1, July 2012, Pages 87-92
Gunam Resul, M.F.M., Mohd. Ghazi, T.I. , Idris, A.
Jatropha curcas oil has good potential as the renewable energy as well as lubricant
feedstock. The synthesis of jatropha biolubricant was performed by transesterification of
jatropha methyl ester (JME) with trimethyl-ol-propane (TMP) and sodium methoxide
(NaOCH 3) as the catalyst. The effects of temperature on the synthesis were studied at a
range between 120C and 200C with pressure kept at 10mbar. The conversion of JME to
jatropha biolubricant was found to be the highest (47%) at 200C. However, it was
suggested that the optimum temperature of the reaction is at 150C due to insignificant
improvement in biolubricant production at higher temperature. To maintain forward
reaction, the excess amount of JME was maintained at 3.9:1 ratio to TMP. The kinetics of
the reaction was studied and compared. The synthesis was found to follow a second
order reaction with an overall rate constant of 1.4910 -1(%wt/wtminC) -1. The
estimated activation energy was 3.94kJ/mol. The pour point for jatropha biolubricant was
at -6C and the Viscosity Index (VI) ranged from 178 to 183. The basic properties of
jatropha biolubricant, pour point, oxidative stability, wear scar and viscosities are found
comparable to other plant based biolubricant, namely palm oil and soybean based
biolubricant.

45-- TECHNICAL SIDE: DIESTERS BIOLUBRICANT BASE OIL: SYNTHESIS,
OPTIMIZATION, CHARACTERIZATION, AND PHYSICOCHEMICAL
CHARACTERISTICS
International Journal of Chemical Engineering
2012, Article number 896598
Salimon, J. , Salih, N. , Abdullah, B.M.
Diesters biolubricant base oil, oleyl 9(12)-hydroxy-10(13)-oleioxy-12(9)- octadecanoate
(OLHYOOD) was synthesized based on the esterification reaction of 9,12-hydroxy-10,13-
oleioxy-12-octadecanoic acid (HYOOA) with oleyl alcohol (OL) and catalyzed by sulfuric
acid (SA). Optimum conditions of the experiment to obtain high yield of OLHYOOD were
predicted at ratio of OL/HYOOA of 2:1mol/mol, ratio of SA/HYOOA of 0.7:1mol/mol,
reaction temperature 110()C, and 7h of reaction time. At this condition, the yield of

Rf. 2012_JR_05
OLHYOOD was 88.7. Disappearance of carboxylic acid (C=O) peak has been observed by
FTIR with appearance of ester (C=O) peak at 1738cm -1. 13C, and 1HNMR spectra
analyses confirmed the result of OLHYOOD with the appearance of carbon-ester (C=O)
chemical shift at 173.93ppm and at 4.05ppm for 13C and 1HNMR, respectively. The
physicochemical characteristics of the OLHYOOD were also determined, which showed
improved low temperature properties (PP) -62C, viscosity index (VI) at 192 and also
increased oxidative stability (OT) up to 215.24C.

46-- TECHNICAL SIDE: BIOLUBRICANT BASESTOCKS FROM CHEMICALLY
MODIFIED RICINOLEIC ACID
Journal of King Saud University - Science
Volume 24, Issue 1, January 2012, Pages 11-17
Salimon, J. , Salih, N., Yousif, E.
This paper presents a series of chemically modified biolubricant basestocks derived from
ricinoleic acid. The reactions were monitored and products were confirmed by NMR and
FTIR. The synthesis protocol is carried out in three stages: (1) epoxidation of ricinoleic
acid; (2) synthesis of 10,12-dihydroxy-9-acyloxystearic acid from epoxidized ricinoleic
acid; (3) esterification of the acyloxystearic acid products with 2-ethylhexanol to yield 2-
ethylhexyl-10,12-dihydroxy-9-acyloxystearate. The viscosity index, flash point, pour
points (PP), and oxidative stability of the resulting products were measured. The
resulting esters could plausibly be used as bio-based industrial materials in biolubricants,
surfactants, or fuel because they have improved physicochemical properties.

47-- TECHNICAL SIDE: CHARACTERISTICS OF BASE FLUID IN
ENVIRONMENTALLY ACCEPTABLE LUBRICANTS
Journal of ASTM International
Volume 9, Issue 1, January 2012
Kusak, B. , Wright, G. , Krol, R. , Bailey, M.
The main component in environmentally acceptable lubricants and grease is the base
fluid. Typically it comprises greater than 70% of grease and 90% of a lubricant. Many
biodegradable fluids have specific characteristics, which make formulating finished
products difficult. Through a stepwise approach these characteristics will be discussed.
The fluids for testing will comprise natural and synthetic esters and some petroleum
based synthetics. The testing will find the extremes of performance at high and low
temperatures and the effects of common additives to improve performance. Testing will
include pour point, elastomer compatibility, oxidation and thermal stability. Based on the
testing a blended fluid will be made to offset the drawbacks of the individual fluids and
the performance discussed. This blend will serve as the base fluid to formulate
environmentally acceptable lubricating grease.

48-- TECHNICAL SIDE: 10-UNDECENOIC ACID-BASED POLYOL ESTERS AS
POTENTIAL LUBRICANT BASE STOCKS
Padmaja, K.V., Rao, B.V.S.K., Reddy, R.K., Bhaskar, P.S., Singh, A.K., Prasad,
R.B.N.
A new class of polyol esters were prepared by esterification of 10-undecenoic acid (UDA)
with three polyols namely trimethylolpropane (TMP), neopentyl glycol (NPG) and

Rf. 2012_JR_05
pentaerythritol (PE) in 92-96% yields. The esters were characterized by IR, 1H NMR,
HPLC and mass spectral studies. Polyol esters were evaluated for basic lubrication
properties and found to be: viscosity at 40C, 11.2-36.1cSt; at 100C, 3.2-7.3cSt;
viscosity index (VI), 162-172; pour point +3 to -36C; flash point, 254-296C. All the
three polyol esters synthesized exhibited good thermal stability with TGA onset
temperatures above 260C. The lubricating properties of the products compared well
with polyol esters based on oleic acid.

49-- TECHNICAL SIDE: DEVELOPMENT OF ECOFRIENDLY/BIODEGRADABLE
LUBRICANTS: AN OVERVIEW (REVIEW)
Renewable and Sustainable Energy Reviews
Nagendramma, P. , Kaul, S.
Synthetic and vegetable oil based esters offer the best choice in formulating environment
friendly lubricants. In the present review an attempt has been made to highlight some
recent developments in the area of biodegradable synthetic ester base stocks for
formulation of new generation lubricants including the efforts made so far at the author's
laboratory in this direction. The developed products find applications in automotive
transmission fluids, metal working fluids, cold rolling oils, fire resistant hydraulic fluids,
industrial gear oils, neat cutting oils and automotive gear lubricants either alone or in
formulations.

50-- TECHNICAL SIDE: CARBON DIOXIDE SOLUBILITY IN REFERENCE AND
VEGETABLE LUBRICANTS DEVELOPED FOR TWO STROKE ENGINES
Journal of Supercritical Fluids
Volume 68, August 2012, Pages 123-130
Regueira, T., Fandio, O., Lugo, L., Lpez, E.R., Fernndez, J.
The solubilities of carbon dioxide, CO
2
, in a reference semi-synthetic oil and in a
developed vegetable-sunflower-based oil for two stroke engines have been measured
from 283K to 348K and pressures up to 9 MPa in a high pressure gas solubility apparatus
that works in isochoric conditions. The densities of the developed vegetable oil from 293K
to 353K and pressures up to 60 MPa were also measured by using a vibrating tube
technique. It was found that the solubility of CO
2
in the vegetable oil is higher than in the
reference semi-synthetic oil. The solubility of CO
2
in both lubricants decreases when the
temperature increases. In addition, we have found that the solubilities of O
2
in these
lubricants are between 7 and 10 times lower than those of
CO2.
Furthermore, PC-SAFT
EoS was employed to model the solubility behavior of CO
2
in both lubricants and the
goodness of Carvalho and Coutinho model for prediction of CO
2
solubility in low volatile
solvents was checked for these lubricants.

51-- POLICY: FNR PRODUCT DATABASE BIO-LUBRICANTS
After the German market introduction programme was ended, the so-called
Positivliste was not continued over the last four years.
This positivlist was changed to a new Datenbank Bioschmierstoffe (product databse for
biolubricants) in which the compliance criteria are those from the CEN Technical Report
CEN/TR 16227:2011 "Liquidpetroleum products - Bio-lubricants - Recommandation for
terminology and characterisation of bio-lubricants and bio-based lubricants. More
information: http://www.bioschmierstoffe.info/service/datenbank-bioschmierstoffe.

Rf. 2012_JR_05
52-- ON THE WEB: CARGILL BUYS FR3 DIELECTRIC FLUID BUSINESS FROM
COOPER POWER SYSTEMS
On 19 June 2012, Cargill and Cooper Power Systems announced the purchase of the
global Envirotemp FR3 fluid business and brand from Milwaukee-based Cooper Power
Systems. Cargill currently manufactures the patented, industry leading FR3 renewable
dielectric fluid made from vegetable oil that is used in a wide range of applications for
transformers and other electrical equipment. Kurtis Miller, president, Cargill Industrial
Oils & Lubricants, said: Now, as a marketer and manufacturer, we will focus on growing
the business with other customers seeking a high-performance, renewable fluid we will
work closely with electrical utility and transformer customers to increase usage of
natural, ester-based FR3 fluid.

53-- ON THE WEB: R.T. VANDERBILT COMPANY, INC. EARNS USDA CERTIFIED
BIOBASED PRODUCT LABEL
On 28 July 2012, R.T. VANDERBILT company inc. announced it had earned the USDA
certified biobased product label for its Molyvan 855 friction reducer. The USDA Certified
Biobased Product Label verifies that the amount of renewable biobased ingredients meets
or exceeds prescribed USDA standards. Biobased products are goods composed in whole
or in significant part of agricultural, forestry, or marine materials. R. T. Vanderbilt
Company, Inc.s commitment to sustainability and to the development of products that
improve sustainability is demonstrated by having a key product, MOLYVAN 855
Friction Reducer, which is a USDA Certified Biobased Product. This product not only uses
a sustainable, biobased raw material, but also provides fuel economy improvement in
motor vehicles and reduces greenhouse emissions said Hugh B. Vanderbilt, Jr.,
Chairman & CEO. Such biobased claims are verified by independent labs and monitored
by the USDA. Consumers may rely on the accuracy of the biobased amount certification
in making informed purchasing decisions.
We are pleased that R.T. Vanderbilt Company, Inc. has earned the USDA Certified
Biobased Product Label, said Ron Buckhalt, USDA BioPreferred Program Manager.
"Biobased products provide opportunities to help add value to renewable commodities,
create jobs in rural communities and generate investment income."

54-- ON THE WEB: RAILMARK LAUNCHES TWO NEW ECO-SAFE PRODUCT LINES
On 10 May 2012, Railmark Holdings Inc. announced that it had launched two new
product lines designed to make the railroad industry a little more Green and a little
more Efficient.
One of the line is a new line of premium quality bio-based, biodegradable rail curve and
switch lubricants. Ultralube brand railroad lubricants are manufactured from renewable
USA-grown crop based oils. The brand will be supplied to the railroad industry by the
Companys Railmark Tarck Works Inc. subsidiary. These products are claimed to have
four times more lubricity than petroleum-based greases and oils while offering better
performance for rail lubricators and switch components and improve safety for
employees and the environment. These new products meet EPAs Environmental
Preferable Purchasing (EPP) criteria and are ECO-SAFE and Non-toxic.

55-- ON THE WEB: PLEWS INTRODUCES ULTRALUBE GREASES FOR RAIL
CURVES AND SWITCH PLATES

Rf. 2012_JR_05
On 16 April 2012, Plews, Inc., dba Plews & Edelmann, announced the introduction of
UltraLube Rail Curve Greases and Switch Plate Lubricants. These premium biobased
greases and lubricants formulated from U.S.-grown vegetable oils are available in
Hi-Visc and Lo-Visc formulations.
UltraLube Rail Curve Greases contain advanced extreme pressure additives to guard
against wheel and rail wear. Both the Hi-Visc and Lo-Visc formulations are available with
added molybdenum disulphide (MoS2), which offers enhanced effects for unsurpassed
protection. All formulations reduce friction and wear between the track and wheel flange,
and their superior lubricity helps improve train fuel efficiency.
The greases are formulated to resist port plugging in wiping bars, and they provide
longer carry down track from the lubricator. They offer better gauge face coefficient of
friction and less migration to the top of the rail than petroleum-based grease.
Recommended for heavy load applications such as coal trains, UltraLube Rail Curve
Greases are designed for wayside applicators with wide temperature requirements. Hi-
Visc Rail Curve Greases pump and carry when the grease temperature is between 2C
(35F) and 71C (160F); Lo-Visc Rail Curve Greases pump and carry when the grease
temperature is between 18C (0F) and 38C (100F). UltraLube Rail Curve Greases are
ideal for all Portec and other brand lubricators.
UltraLube Switch Plate Lubricants also available in Hi-Visc and Lo-Visc versions are
formulated with the best optimized natural seed oils and proprietary additives to protect
railway switches from wear and prevent rust and corrosion. Designed to be poured,
brushed, wiped or sprayed on railroad switches, the lubricants provide good penetration
into the switces. They help prevent dust and dirt buildup, and they resist washout from
rain or melting ice.
UltraLube Rail Curve Greases and Switch Plate Lubricants meet the EPAs Environmental
Preferable Purchasing (EPP) criteria, and their biodegradable formula makes them ideal
for use in environmentally sensitive areas near waterways.
With four times the natural lubricity of petroleum-based oils, UltraLube products instantly
penetrate into areas where lubrication is needed most, creating a long-lasting bond to
metal and plastic surfaces. Made from crops grown in the United States, UltraLubes
vegetable-based formula is eco-safe and non-toxic. Because they are VOC-free and non-
flammable with extremely high flash points, UltraLube greases and oils are ideal for
environmentally sensitive areas.

56-- ON THE WEB: COSAN COMPLETES ACQUISITION OF COMMA OIL
On 3 July 2012, COSAN S.A. INDSTRIA E COMRCIO announced that on July 1
st
2012 it
successfully completed the acquisition of Comma Oil & Chemicals Limited (Comma)
from Esso Petroleum Company, Limited (following a corporate reorganization).
The acquisition of Comma reinforce Cosan`s strategy to enter into the European
lubricants & specialties market.
The acquisition of Comma by Cosan includes finished lubricants and chemicals
manufacturing and sales to third parties; all assets located at Commas Gravesend site in
Kent, England; and ownership of the Comma trademarks and brands. In addition,
agreements will be in place to allow Comma to continue to distribute select Mobil-
branded lubricants into specific UK channels and to continue to manufacture and supply
ExxonMobil companies with a range of seasonal and ancillary automotive products.

Rf. 2012_JR_05
57-- ON THE WEB: ASTM RELEASES NEW COMPILATION ON TESTING AND USE
OF ENVIRONMENTALLY ACCEPTABLE LUBRICANTS
On 6 February 2012, ASTM announced the release of a new compilation, STP 1521, on
testing and use of environmentally acceptable lubricants. This compilation presents the
latest research on biobased and other environmentally acceptable (EA) lubricants.
With the increased interest in environmentally acceptable lubricants, STP 1521 is a must-
have for those in the agricultural, construction, forestry, lumber and mining industries
where involuntary or accidental fluid leakage or spillage is detrimental to the
environment.
The book includes ten peer-reviewed papers that cover:
Fundamentals of biobased lubricants;
Industrial trends;
Applications;
New test methods; and
Environmental policies.
More information on ASTM web site: www.astm.org.

58-- ON THE WEB: BIO-BASED FLUIDS COME IN FROM THE COLD
In the May 2012 issue of the Offshore Engineer magazine, Jennifer Pallanich talks to
Terresolve CEO Mark Miller about the bio-based fluids his company has been developing
for offshore use. Fluids working in hot temperature environments often have antioxidants
and fluid improvers while their cold-weather counterparts will require cold-flow improvers
and pour point depressants. Fluids used in wet applications frequently need hydrolytic
stabilizers, while those operating in dirty conditions contain detergency and dispersancy.
Terresolve's readily biodegradable fluids are made from an environmentally safe base
synthetic base oils that can withstand heat, water and contamination. The fluids can
withstand such conditions because of the way the base oils are combined with
performance chemistry modifiers. Terresolve has just wrapped up Arctic testing on
EnviroLogic 3046, a member of its EnviroLogic 3000 line of synthetic high-performance
readily biodegradable and non-toxic hydraulic fluids. Once a lubricant is properly
designed for one application, it is vital to ensure it can be appropriately used in a
different application.

59-- ON THE WEB: DOSSIER ON BIOLUBRICANTS IN THE FRENCH MAGAZINE
FORMULE VERTE
The issue number 10 of the French magazine Formule Verte includes a special dossier on
biolubricants entitled Biolubrifiants: la filire sorganise (interviews of Novance, Molydal, Motul
Tech, Condat, ITERG, ValBiom, Ple IAR).

60-- ECO-LABELS IN EUROPE: THE EU ECO-LABEL
Since one year, the European Commission has its own database for ecolabeled products.
This database has some technical problems and companies have difficulties to enter their
products in it. Therefore, the database is not yet up-to-date.
In this survey, last figures on ecolabeled lubricants and companies date back to June
2012. At this date, there were 26 companies producing 132 ecolabeled products (of
which some are different viscosities of the same product). These products comprised all
together: 82 hydraulic oils, 25 chain saw oils, 7 two stroke oils, 11 greases, 1 concrete
release agents and 6 niche loss lubricants.

Rf. 2012_JR_05
The progress made since 2007 is illustrated in the figure below. After a slow start, in
2008 the number of lubricants awarded with the flower increased largely reflecting the
increasing interest for ecolabeled lubricants.

Rf. 2012_JR_05

61-- ECO-LABELS IN EUROPE: LIST OF LUBRICANT SUPPLIERS THAT GOT LICENSES (UPDATED 10 JULY 2012
1
)

Swedish
Standard
Hydraulic oils
SS 15 54 34
Swedish
Standard
Lubricating
Greases
SS 15 54 70
Nordic Swan

BLUE ANGEL
Hydraulic Fluids
RAL-UZ 79
BLUE ANGEL
Lub. and Form.
Oils
RAL-UZ 64
EUROPEAN
ECO-Label

1
2 Agro Oil Agro Oil
3 Andreas Stihl
4 Aral
5 Avia Minerall
6 BASF SE BASF Pers. Care BASF SE
7 Bau +
Metallchemie

8 BayWa BayWa
9 Bechem (Carl) Bechem (Carl) Bechem (Carl) Bechem (Carl)
10 Binol Binol Binol Biosafe Oy
11 Bioil
12 Biostar oil
13 Blaser Swisslube
14 BP
15 Bremer & Leguil
16 Canadian Oil AB
17 Calpam Minerall
18
19 Cargo Oil Cargo Oil
20 Caterpillar
21 CEPSA lubricantes
22 Cognis Deutsch. Cognis Deutsch. Cognis
23 Condat
24 De Oliebron
25 EDE
26 Eliassons Maskin
27 ELASKON
SACHSEN

28 Eni
Schmiertechnik

Rf. 2012_JR_05
GmbH
29 Envirosys
30 Esso Deutschland Esso Deutshland
31 Eurol bv
32 Exxon Mobil Lub.
33 FINKE Minerallw. FINKE Minerallw.
34 F L Nordic
(Ambra)

35 Fragol
Schmierstoff
Fragol
Schmierstoff

36 Fuchs Fuchs Fuchs Fuchs
37 G. A. Lindberg
38 Green Oils
39 Gulf Oil
international

40 Handelsges. fr
Kr.
Handelsges. fr
Kr.

41 Hebro Chemie
42 Hunold
Schmierstoffe

43 Husqvarna austria
44 Hydroscand
45 Interflon
46 John Deere
Forestry

47 Kajo-Chemie Kajo-Chemie Kajo-Chemie Kajo-Chemie
48 Kettlitz Chemie Kettliz Chemie
49 Klber Lubrication
50 Komatsu Forest
51 KROON OIL
52 Lubrizol
53 Mastertec
54 Matzke (Roland)
55 Matrix Lubricants Matrix Lubricants
56 mbg d.o.o.
57 MC-Bauchemie
Mller

58 MCB Larsson Mill.
59 Midland Midland
60 Mobil Oil

Rf. 2012_JR_05
61 Morris lubricants
62 Motorex
63 Motul BP 94 Motul
64 Natoil AG Natoil AG
65 Neste Oil AB Neste Oil AB
66 Nordisk
Dck.(Agip)

67
68 Novance
69 NYCO. NYCO
70 OK-Q8 OK-Q8
71 OMV Refining and
marketing
72 Oy voitelukeskus
tontilla
73 Pakelo Motor Oil
74 Panolin
Scandinav.
Panolin Panolin Panolin AG
75 Peri
76 Petronas
77 Preem Preem

78 PRO FLUID
79 Ramby Oljor &
Verk.

80 REPSOL
81 Rottne Industri
82 Skand. Oljecentr.
83 SKF Maint. Prod.
84 Shell Svenska Shell Shell Deutshland Shell International
85 Schrling
Fahrzugbau
Haslingen Gmbh

86 Starke & Sohn
87 Statoil Lubricants Statoil Lubricants
88 S.T.L. Lubricants
89
90 Technolub
Schmier

91 Total Lub.Sweden TOTAL

Rf. 2012_JR_05
92 Trennfit GmbH &
Co.Bauindustrie
KG

93 Valvoline Intern.
94 Veba Oel Vertrieb
95 Voitel. Tont.
96 Voith TURBO
GmbH &Co.KG

97 Volvo CE Volvo CE Intern.
98 Zeller & Gmelin Zeller & Gmelin Zeller & Gmelin
99
Status
Dec.
2011
34 companies 13 companies 0 companie 25 companies 24 companies 28 companies
80 products 20 products 0 products 75 products 49 products 97 products
Status
June/Ju
y 2012
38 companies
(+2;-1)
14 companies
(+1)
0 companie 24 companies (-1) 27 companies
(+3)
26 companies
(+10;-8)
90 products 22 products 0 products

70 products 52 products 132 products

1
Since one year, the European Commission has its own database for ecolabeled products. This database has some technical problems and companies have difficulties to
enter their products in it. Therefore, the database is not yet up-to-date. In this survey, last figures on lubricants and companies awarded with the European ecolabel date
back to June 2012.

Rf. 2012_JR_05

62ECO-LABELS IN EUROPE: EVOLUTION OF COMPANIES AWARDED WITH AN ECO-LABEL (FROM JANUARY 2007 TO JULY
2

2012)

2
Since one year, the European Commission has its own database for ecolabeled products. This database has some technical problems and companies have difficulties to
enter their products in it. Therefore, the database is not yet up-to-date. In this survey, last figures on lubricants and companies awarded with the European Ecolabel (EEL)
date back to June 2012.

Valbiom Julieroiz Technicalandmarketsurvey July20121348649987

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Author: Julie Roz, roiz@valbiom.be, +32 81 62 23 50.

ValBiom Gembloux Agro-Bio Tech Universit de Lige

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