CCR Technologies Inc.

Literature Search

Ethylenediamines
Ethylenediamines
Ethylenediamines are contaminants formed when amine molecules degrade, and they have been somewhat
controversial as a topic in the technical literature over the past couple of years. The controversy has centered on
(1) whether or not these compounds really do form in primary and secondary amines and formulated MDEA
solutions, and (2) whether or not they are in fact corrosive. We have done a literature search on these
compounds and have compiled this information, as well as information based on knowledge gained from
systems we have cleaned over the past few years. The following should provide a technical summary for
dealing with ethylenediamines and the amines from which they are derived.
Ethylenediames are also simply called diamines, or may even be referred to as dimers, and are generally formed
in the presence of primary or secondary amines when CO2 is present in the treated gas. They are not always
measured in amine analyses, possibly for economical reasons, marketing reasons, lack of clear understanding, or
a combination of these reasons.
We have found that ethylenediames have been an issue with some of our customers using generic primary and
secondary amines, as well as some amine blends. The issues surrounding these compounds have been related to
solution physical properties and how they effect unit operations. In some cases these compounds have been
implicated in raising the corrosive potential of the circulating solution.
Literature Search
We have done a limited literature search on ethylenediamines in gas treating solutions. Some of the information
is clear, and some of the information is contradictory. We have summarized this information to support our
findings and to allow plant operators to learn more on the subject.
1. Contamination and Purification of Alkaline Gas Treating Solutions
This 1996 paper addresses ethylenediamines and their complexing power towards the metal in the unit,
therefore addressing the corrosive potential of the compound. It also talks about the difficulty
associated with amine solution analysis.
2. Amine Degradation Chemistry in CO2 Service
This 1998 paper addresses ethylenediamine formation in the presence of CO2 in generic amine systems
and in formulated amine systems. This paper once again addresses the difficulty in analyzing the
solution and addresses how the ethylenediamine base strength may suggest higher active amine strength
than is really present in the solution. Finally the paper once again addresses the corrosive potential of
the contaminant.
3. Comparison of Laboratory and Operating Plant Data of MDEA/DEA Blends
This 1999 paper goes through the degradation mechanism of the circulating amine solution, and appears
to down play the affect of ethylenediamine formation in MDEA/DEA blends.
4. Mixed Amines In Gas Treating Service
This is a CCR Technical Bulletin highlighting an MDEA/DEA blend with a significant amount of
ethylenediamine (THEED) in the circulating solution. In this case, the THEED was implicated as the
potential corrosive agent in the solution, and the removal of it did help to lower the corrosive potential
of the solution.

CCR Technologies Inc., 1500 CityWest Blvd. - Suite 550, Houston, Texas 77042
Phone: (281) 988-5800 Fax: (281) 988-5858 www.reclaim.com

CCR Technologies Inc. Literature Search Ethylenediamines

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5. Contaminant Reporting in Amine Gas Treating Service

This 2000 paper addresses the importance of a complete solvent analysis to identify most if not all of the
issues surrounding each type of amine. The paper addresses ethylenediamine analytical reporting and
discusses ethylenediamines found in mixed systems (CO2 and H2S) as opposed to CO2 only systems.
6. Overcoming Operating Challenges at AEC Oil & Gas Sexsmith with Sulfinol D
This 2001 paper addresses ethylenediamines (referred to as dimers) in a mixed solvent. Experience
showed corrosion when dimers were present, and also showed lower corrosion rates once the dimers
were removed from the solution.
7. Canadian Gas Treating Solvent Quality Control Unique Challenges
This 2001 paper addresses the issue of ethylenediamines showing up in a standard analysis as useful
amine. The paper further goes on to show that removal of the ethylenediamines may give a false high
solvent loss rate during reclaiming operations.
8. Degradation of Amine Solvents and The Relation With Operational Problems
This 2002 paper again addresses the issue of ethylenediamine formation and in the paper they refer to
them as dimers. This paper further addresses the corrosive potential of these compounds and ways for
removing these compounds from the circulating solution.
Conclusions
While a literature search may sometimes seem confusing and contradictory, conclusions may still be reached
based on the consensus of the publications. In this case the conclusions are; (1) that ethylenediamines have the
ability to raise the corrosion potential of the circulating amine solution, and (2) analysis for ethylenediamine
compounds is expensive, complex, and is not always completed by all labs.
It is recommended, therefore, that an experienced lab periodically perform a complete sample analysis,
including direct measurement of water content and any ethylenediamines formed from amine degradation. This
will ensure that proper solvent quality control may be achieved to maximize the reliability of the gas treating
plant.
For more information or to inquire about a complete sample analysis contact CCR Technologies Inc. in Houston
at 281-988-5800, or visit us at www.reclaim.com.
References
1. McCullough, J. G., and R. B. Nielsen, Contamination and Purification of Alkaline Gas Treating Solutions,
Corrosion96, Paper No. 396, 1996.

2. Holub, P. E., J. E. Critchfield and W. Y. Su, Amine Degradation Chemistry in CO2 Service, Proceedings of the
3.
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8.

1998 Laurance Reid Gas Conditioning Conference.

Dupart, M. S., P. C. Rooney, and T.R. Bacon, Comparison of Laboratory and Operating Plant Data of
MDEA/DEA Blends, Proceedings of the 1999 Laurance Reid Gas Conditioning Conference.
CCR Technologies Inc. Technical Bulletin, Mixed Amines In Gas Treating Service, 2001.
Haws, R., and J. Jenkins, Contaminant Reporting in Amine Gas Treating Service, Proceedings of the 2000
Sulfur Recovery Symposium, Vail, Colorado.
Kehl, T., and R. Barker, Overcoming Operating Challenges at AEC Oil & Gas Sexsmith with Sulfinol D,
Proceedings of the 2001 Laurance Reid Gas Conditioning Conference.
Carlson, S., S. Canter, and J. Jenkins, Canadian Gas Treating Solvent Quality Control Unique Challenges
Proceedings of the 2001 Sulfur Recovery Symposium, Canmore, Alberta.
Smit, C. J., G. J. van Heeringen, and P. F. A. van Grinsven, Degradation of Amine Solvents and The Relation
With Operational Problems, Proceedings of the 2002 Laurance Reid Gas Conditioning Conference.

Disclaimer: The information in this document is to the best of our knowledge accurate at the date of publication. We shall
not be liable for any loss or damage resulting from reliance on its contents. All warranties howsoever made or implied in
respect of this publication are excluded.