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PERP Program New Report AlertAugust 2002

Chem Systems' Process Evaluation/Research Planning program has published a new report,Ethano lamin es (01/02S2).

Ethanolamines - monoethanolamine (MEA), diethanolamine (DEA), and triethanolamine(TEA) -- are a family of versatile chemicals that combine the properties of amines andalcohols. Because of the amine functionality, they are mildly alkaline and react with acids toform salts or soaps. The alcohol functionality permits esterification and imparts hygroscopicproperties.

Ethanolamines find uses in such diverse areas as gas sweetening, detergent and specialtycleaner formulations, flexible urethane foam catalysts, pharmaceuticals, textile processing

aids, personal care products, metalworking and oil well rust preventatives, concrete additives,agricultural chemicals, photographic emulsions, adhesive/rubber chemical intermediates,packaging and printing inks, and others.

Consolidation occurred in the industry in February 2001 when Union Carbide was acquiredby Dow. The Federal Trade Commission required Dow to sell its global ethanolaminesbusiness, and this was subsequently purchased by Ineos.

The technology of ethanolamines production has traditionally involved the uncatalyzedreaction of ethylene oxide with aqueous ammonia to give a mixture of mono-, di-, andtriethanolamines. The ratio of products in the mixture is influenced by the ratio of ammonia to

ethylene oxide in the reactor and the degree of recycling of the undesired compounds. Suchprocesses are actively licensed by Scientific Design and by Davy (Kvaerner) ProcessTechnology.

In an apparent move to maximize diethanolamine for use as an intermediate for glyphosateherbicides (e.g. Roundup), Nippon Shokubai has recently disclosed a process using azeolite catalyst to bias the product distribution towards diethanolamine. A conceptual catalyticprocess using anhydrous ammonia is evaluated in this report and compared to theconventional uncatalyzed process using aqueous ammonia. The main basis for selectionbetween the processes is the preferred product distribution and the degree of flexibilityrequired. Uncatalyzed processes offer more flexibility in the product distribution; however,

they are not particularly suitable for attaining a very high proportion of a specific ethanolamineproduct. While anhydrous processes excel in product selectivity, the high operating pressuresnecessary with anhydrous processes add to the safety requirements in handling of ethyleneoxide and to capital and operating costs.

Ethanolamines can be regarded as derivatives of ammonia in which one, two, or threehydrogen atoms have been replaced by a CH2-CH2-OH group. An alternative view is theformation of an addition product of ammonia with one, two, or three moles of ethylene oxide.

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NH3 + H2C CH2

O

H2N CH2 CH2 OH

Ammonia Ethylene Oxide Monoethanolamine

H2N CH2 CH2 OH + H2C CH2

OMonoethanolamine Diethanolamine

HN (CH2 CH2 OH)2 + H2C CH2

ODiethanolamine Triethanolamine

Q3_02\PERP\0002\4049\4049-1.CDX

HN (CH2 CH2 OH)2

N (CH2 CH2 OH)3

Nippon Shokubai has developed a process for ethanolamines that is capable of changing theproduction ratio of mono-, di-, and tri-ethanolamine to produce a high proportion ofdiethanolamine in comparison to the conventional process. The reactor uses a zeolitecatalyst, activated with rare earth metals, and operates in an anhydrous, liquid phaseenvironment. Reaction conditions are 140-150C and about 100 bars (1450 psi). The NipponShokubai process suppresses the production of TEA and produces more MEA and DEA,since the catalyst recognizes the size and shape of molecules.

The new process is being retrofitted into an existing 40,000 metric ton per year unit in theKawasaki Works at a revamp cost of $6 million. Start-up was scheduled for July 2002.

This new report from Nexant/Chem Systems compares the process technology andproduction economics of conventional un-catalyzed processes for making ethanolamines tothe emerging Nippon Shokubai catalytic process.

= = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = = =Nexant, Inc./Chem Systems (www.chemsystems.com) is a leading management consultancy to the globalenergy, chemical, and related industries. For over 30 years, Chem Systems has helped clients increase businessvalue through assistance in all aspects of business strategy, including business intelligence, project feasibility andimplementation, operational improvement, portfolio planning, and growth through M&A activities. Chem Systems

has its main offices in White Plains (New York) and London (UK), and satellite offices worldwide.

These reports are for the exclusive use of the purchasing company or its subsidiaries, from Nexant ChemSystems, 44 South Broadway, 5th Floor, White Plains, New York 10601-4425 U.S.A. For further information aboutthese reports contact Dr. Jeffrey S. Plotkin, Director, PERP Program, phone: 1-914-609-0315; fax: 1-914-609-0399; e-mail: jplotkin@nexant.com; or Heidi Junker Coleman, phone: 1-914-609-0381, e-mail address:hcoleman@nexant.com, Website: http://www.chemsystems.com

mailto:jplotkin@nexant.com;mailto:jplotkin@nexant.com;mailto:hcoleman@nexant.commailto:hcoleman@nexant.comhttp://www.chemsystems.com/http://www.chemsystems.com/http://www.chemsystems.com/mailto:hcoleman@nexant.commailto:jplotkin@nexant.com;