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Method of Manufacturing Ethyleneamines Verfahren Zur Herstellung Von Ethylenaminen Méthode De Fabrication D Éthylène-Amines

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Method of Manufacturing Ethyleneamines Verfahren Zur Herstellung Von Ethylenaminen Méthode De Fabrication D Éthylène-Amines (19) TZZ ¥Z_T (11) EP 2 346 809 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 209/08 (2006.01) C07C 209/22 (2006.01) 13.01.2016 Bulletin 2016/02 C07C 211/10 (2006.01) C07C 211/14 (2006.01) (21) Application number: 09736706.4 (86) International application number: PCT/US2009/005470 (22) Date of filing: 06.10.2009 (87) International publication number: WO 2010/042158 (15.04.2010 Gazette 2010/15) (54) METHOD OF MANUFACTURING ETHYLENEAMINES VERFAHREN ZUR HERSTELLUNG VON ETHYLENAMINEN MÉTHODE DE FABRICATION D ÉTHYLÈNE-AMINES (84) Designated Contracting States: • SRNAK, Thomas Z. AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Arlington Heights HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL Illinois 60004 (US) PT RO SE SI SK SM TR (74) Representative: Beck Greener (30) Priority: 06.10.2008 US 195454 P Fulwood House 12 Fulwood Place (43) Date of publication of application: London WC1V 6HR (GB) 27.07.2011 Bulletin 2011/30 (56) References cited: (73) Proprietor: Union Carbide Chemicals & Plastics WO-A1-99/24389 WO-A1-03/010125 Technology LLC IL-A- 57 019 US-A- 2 861 995 Midland, MI 48674 (US) US-A- 3 037 023 US-A- 5 321 160 US-A- 5 750 790 (72) Inventors: • PETRAITIS, David M. • DATABASE WPI Week 200452 Thomson Covington Scientific, London, GB; AN 2004-541915 Louisiana 70433 (US) XP002563784 & RU 2 226 189 C1 (KAUSTIK • KING, Stephen W. STOCK CO) 27 March 2004 (2004-03-27) League City Texas 77573 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 346 809 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 346 809 B1 Description BACKGROUND 5 [0001] Numerous processes for the production of ethyleneamines are known. Of these processes, the two most commonly used process are (1) the reaction of ethylene dichloride (EDC) with ammonia (NH 3) followed by neutralization with sodium hydroxide (NaOH) to produce ethyleneamines and salt (referred to herein as "EDC Process"); and (2) the reductive amination of monoethanolamine (MEA) with ammonia (NH 3) over a heterogeneous catalyst (referred to herein as "RA Process"). A third viable technology, which is not commonly practiced in the industry for the production of 10 ethyleneamines, is condensation. A condensation reaction is a chemical reaction in which two molecules (groups) combine to form a single molecule together with a loss of a small molecule (e.g., water or ammonia). [0002] The EDC process typically produces a full range of ethyleneamines whereas the RA process is highly selective in the production of lighter amines, for example, ethylenediamine and diethylenetriamine. The condensation process typically produces a product mix that is somewhere between an EDC process and an RA processes. For each of these 15 technologies, the degree of mix flexibility attainable is constrained by the chemistry, the process employed and the investment required to operate over a broad range of reaction conditions and the capital investment and operating costs required to recycle materials to the reactor. [0003] In view of the limitations inherent in known ethyleneamine-generating processes, it would be desirable to have available a method of manufacturing ethyleneamines that is capable of providing an ethyleneamine manufacturer with 20 improved product mix flexibility, and that could be cost-effectively retrofitted into an existing ethyleneamines-generating process or designed into a new plant. [0004] US 5 321 160 A discloses a process for producing an ethylenamine, which comprises reacting ammonia and/or an ethylenamine with an ethanolamine in the presence of hydrogen to obtain an ethylenamine having an increased number of ethylene chains over the ammonia and/or the ethylenamine used as the starting material. 25 [0005] US 2 861 995 A discloses a continuous process for converting ethanolamine into multiple-nitrogen-containing products including ethylene diamine, polyethylne polyamines and piperazine. The process includes passing a stream of ethanolamine and ammonia, under pressure, over a fixed bed of a metal hydrogenation catalyst while being maintained at an elevated temperature. [0006] WO 03/010125 A1 discloses a process for the manufacture of diethylenetriamine and higher polyethylenep- 30 olyamines by a transamination of ethylenediamine. The transamination is performed at a temperature from 135 °C to 180 °C at a pressure from 5 Mpa to 40 Mpa in the presence of hydrogen and a particulate catalyst containing 26 to 65% by weight of nickel on an oxide carrier. SUMMARY 35 [0007] The present invention provides methods of manufacturing ethyleneamines that makes use of an ethyleneamine- generating processthat is coupledto a transamination process. The combinationof an ethyleneamine-generating process with a transamination process improves the mix flexibility that can be obtained from the single process allowing the production of ethyleneamine compositions having a controllably different and more desirable product mix. More specif- 40 ically, a relatively less desirable ethyleneamine product mix (e.g., coming from a relatively less controllable ethylene- amines-generating process such as reductive amination) can be transformed into a more desirable ethyleneamine product mix by subjecting the less desirable ethyleneamines product mix to a transamination process. [0008] The method comprises the steps of: (a) manufacturing an ethyleneamines composition comprising a mixture of ethyleneamines using an ethyleneamine-generating process in an ethylenedichloride (EDC) or a reductive amination 45 (RA) reactor, the ethyleneamines-generating step being selected from an EDC process or an RA process; and (b) transaminating at least a portion of the ethyleneamines composition in a transamination reactor to form a transaminated ethyleneamines composition. The transaminated ethyleneamines composition comprises at least one ethyleneamine that is present in an amount that is greater than the amount that the at least one ethyleneamine is present in the ethyleneamines composition that is transaminated in step (b). In this way, the composition of the product is increased 50 in one or more desirable ethyleneamines (e.g., DETA, AEP and TETA) as compared to the composition that is transam- inated in step (b). BRIEF DESCRIPTION OF THE FIGURES 55 [0009] FIG. 1 is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. 2 EP 2 346 809 B1 FIG. 1A is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. FIG. 1B is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. 5 FIG. 1C is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. FIG. 1D is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. FIG. 1E is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the 10 present invention. FIG. 2 is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. FIG. 2A is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. 15 FIG. 2B is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. FIG. 2C is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the present invention. FIG. 2D is a flow chart of an embodiment of an ethyleneamines manufacturing process in accordance with the 20 present invention. DETAILED DESCRIPTION [0010] Reference will now be made in detail to representative embodiments of the invention. While the invention will 25 be described in conjunction with the enumerated embodiments, it will be understood that they are not intended to limit the invention to those embodiments. On the contrary, the invention is intended to cover all alternatives, modifications, and equivalents that may be included within the scope of the present invention as defined by the claims. [0011] One skilled in the art will recognize many methods and materials similar or equivalent to those described herein, which could be used in and are within the scope of the practice of the present invention. The present invention is in no 30 way limited to the methods and materials described. [0012] All publications and patents mentioned herein are incorporated herein by reference in their respective entireties for the purpose of describing and disclosing, for example, the constructs and methodologies that are described in the publications which might be used in connection with the presently described invention. The publications discussed above and throughout the text are provided solely for their disclosure prior to the filing date of the present application. Nothing 35 herein is to be construed as an admission that the inventor is not entitled to antedate such disclosure by virtue of prior invention. [0013] Unless defined otherwise, technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although any methods, devices, and materials similar or equivalent to those described herein can be used in the practice or testing of the invention, the 40 preferred methods, devices and materials are now described. [0014] As used herein, the following abbreviations have the following meanings: AEEA refers to aminoethyleth- anolamine. AEP refers to aminoethylpiperazine. DETA refers to diethylenetriamine.
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