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ESTERIFICATION
ESTERIFICATION
The basics of the reaction involve a process
called condensation in which a small molecule
of water is split out between two compounds,
leaving a linkage to form a larger molecule
from the original units:
Carboxylic Acid
Alcohol
Ester
Water
ESTER
Esters with low molecular weight are commonly used as
fragrances and found in essential oils and pheromones.
Substances associated with aromas and flavor essences. For
example, ethyl butanoate (aroma of pineapples):
Fats and oils are also esters. These are composed of the
triol glycerol, and long-chain "fatty" acids:
Example
Artificial flavours
Essences
Perfumes
Plasticizer
PVC
MAKING ESTERS
Produced when carboxylic acids are heated
with alcohols in the presence of an acid
catalyst.
Water is remove during the reaction.
Catalyst is usually concentrated sulphuric acid.
Catalyst is needed to make the reaction occur
at a useful rate.
Carboxylic acid
Ethanoic acid
alcohol
Ethanol
ester
water
Ethyl ethanoate
water
(colorless liquid with
sweet smell (similar to
pear drops))
pear drops
Advantages
Disadvantages
PROCESS:
PRODUCTION OF LEVULINIC ACID
AND LEVULINATE ESTER
( BIOFINE PROCESS)
** precursor is a compound that participates in the chemical reaction that produces another compound.
BIOFINE PROCESS
LEVULINIC ACID
Levulinic acid is derived from lignocellulosic biomass
Levulinic acid, or 4-oxopentanoic acid, is the simplest
member of the comparatively rare class of organic
compounds known as gamma-keto acids.
Having both a ketonic carbonyl group and an acidic
carboxyl group, it reacts as a ketone and as a fatty acid.
The chemical structure of levulinic acid may be
represented as:
CH3 COCH2 CH2 COOH
LA potential
LA is a valuable platform chemical due to its
particular chemistry it has two highly reactive
functional groups that allow a great number of
synthetic transformations.
LA can react as both a carboxylic acid and a
ketone.
Enzymatic Hydrolysis
Enzymatic hydrolysis and in conventional
dilute/concentrated acid hydrolysis
technologies use of biological agents to
convert sugars, fermentation process
takes a significant time.
Cellulase enzyme and fermentation
organisms require about 7 days to bring
about the conversion to ethanol.
lower range of feasible feedstocks.
Steric hindrance, caused by ligninpolysaccharide linkages, limits access of
fibrolytic enzymes to specific
carbohydrate moieties
Resulting in lower yields or the need for
steam-explosion pre-treatment
Feedstock
Sources
Post-fermentation liquor
Rice hull
Sumiki, 1948)
Oat residues
Rodriguez, 1973
Faerber, 1943
Fir sawdust
Haworth, 1966
Naphtha
Cotton balls, rice, straw, soybean skin, soybean oil residue, corn husks
Cotton stems
Cottonseed hulls
Akmamedov, 1962
Molasses
Starch
Takahashi, 1944
Shil'nikova, 1967
Tapioca meal
Chapman, 1971
Hydrolysis reaction
Crushing
Lignocellulosic
Material
Separation
CRUSHING
The biomass (lignocellulosic
undergoes crushing process.
Function:
Reduce the size ( 0.5-1.0 cm)
Efficient hydrolysis
Optimum yield
material)
HYDROLYSIS PROCESS
1) MIXING TANK
The biomass is move to high pressure air
injection system to a mixing tank
Sulphuric acid (HSO) being added as catalyst
Addition of some sodium/potassium sulphate
(to prevent coagulation)
2) TUBULAR REACTOR
The mixture is move to tubular reactor
Condition :
Temperature (210-220C)
Pressure (25 bar)
Time (12 s)
Function :
Depolymerise the polysaccharides onto the
soluble monomer (eg: hexose)
3) STIRRER TANK
Moved to continuous stirred tank reactor
Condition:
Time ( 20 min)
Product :
Furfural
Formic acid
SEPARATION
FILTRATION
References
http://www.chemtopics.com/aplab/ester.pdf
http://www.academia.edu/3203706/A_roadmap
_for_conversion_of_lignocellulosic_biomass_to_c
hemicals_and_fuels
Daniel J.Hayes et al. Production of Levulinic Acid,
Furfural and Formic acid from Lignocellulosic
Feedstock.
Anna Maria Galletti et al. Conversion of Biomass
to Levulinic acid, A New Feedstock for Chemical
Industry.