WO2006114417A2 - Procede de production d'amines d'ethylene - Google Patents

Procede de production d'amines d'ethylene Download PDF

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Publication number
WO2006114417A2
WO2006114417A2 PCT/EP2006/061823 EP2006061823W WO2006114417A2 WO 2006114417 A2 WO2006114417 A2 WO 2006114417A2 EP 2006061823 W EP2006061823 W EP 2006061823W WO 2006114417 A2 WO2006114417 A2 WO 2006114417A2
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WO
WIPO (PCT)
Prior art keywords
meoa
range
reaction
reaction stage
catalyst
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PCT/EP2006/061823
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German (de)
English (en)
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WO2006114417A3 (fr
Inventor
Holger Evers
Johann-Peter Melder
Walter Himmel
Thomas Krug
Till Gerlach
Michael Jödecke
Jan Nouwen
Roderich RÖTTGER
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Basf Aktiengesellschaft
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Publication of WO2006114417A2 publication Critical patent/WO2006114417A2/fr
Publication of WO2006114417A3 publication Critical patent/WO2006114417A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins

Definitions

  • the present invention relates to a process for the production of ethylene amines.
  • Ethyleneamines are used as solvents, stabilizers, for the synthesis of chelating agents, resins, drugs, inhibitors and surfactants.
  • WO-A1-01 / 94290 discloses a process for the preparation of alkanolamines from alkylene oxide and ammonia, wherein a controlled control of the temperature in the reaction space.
  • EP-A2-1 291 339 (BASF AG) relates to a continuous process for the preparation of monoethanolamine, diethanolamine and triethanolamine by reacting ammonia and ethylene oxide in the liquid phase in the presence of water as catalyst in a pressure column.
  • DE-A-1 941 859 (Mo Och Domsjö Aktiebolag) (US equivalent 3,697,598) relates to a continuous process for the preparation of monoalkanolamines from an alkylene oxide and ammonia in the presence of a cation exchange resin catalyst.
  • EP-A1-652 207 (Nippon Shokubai) describes a process for preparing an alkanolamine by reacting an alkylene oxide with ammonia in the liquid phase in the presence of a catalyst comprising a rare earth element on an inorganic heat-resistant support (eg phyllosilicate) ,
  • the ethylene dichloride (EDC) process involves the chlorination of ethylene and subsequent reaction with ammonia.
  • Disadvantage of the implementation is the comparison wise costly functionalization by reaction with chlorine, associated with an inevitable salt attack in the substitution with ammonia. Subsequently, the neutralization with sodium hydroxide to release the ethyleneamines is inevitable.
  • a reaction of monoethanolamine and ammonia to amination catalysts takes place in the presence of hydrogen.
  • Raw material base is also ethylene, which is first functionalized to ethylene oxide.
  • the opening of the epoxide with ammonia provides a mixture of mono-, di- and triethanolamine, which is separated by distillation into the individual components.
  • Monoethanolamine (MEOA) is then by amination in a mixture of ethylenediamine (60- 80 wt .-%), Diethylentria- min (5-15 wt .-%) and higher linear polyethyleneamines in addition to piperazine and piperazine derivatives (5-15 wt .-%) as cyclic secondary products.
  • by-product aminoethylethanolamine (AEEA, 5-15% by weight) is obtained by intermolecular reductive amination of two MEOA units.
  • EP-A2-146 508 (Berol Kemi AB) relates to specific Ru catalysts and their use in processes for the amination of alkanolamines.
  • EP-A2-839 575 (BASF AG) describes Ru catalysts for the amination of alcohols, such. Monoethanolamine.
  • WO-A-05/014523 (BASF AG) relates to a process for the preparation of ethyleneamines by reacting monoethanolamine (MEOA) with ammonia in the presence of a catalyst in a reactor (1) and separating the resulting reaction output, wherein obtained in the separation Ethylenediamine (EDA) is reacted in a separate reactor (2) in the presence of a catalyst to diethylenetriamine (DETA) and the resulting reaction effluent is fed to the separation of the reaction effluent resulting from reactor 1.
  • MEOA monoethanolamine
  • DETA diethylenetriamine
  • US-A-3,597,483 (BASF AG) relates to the direct preparation of 1, 2-diamines by reaction of 1, 2-epoxides with ammonia, primary or secondary amines in the presence of water, hydrogen and a hydrogenation catalyst.
  • DD-A-149 509 (VEB Leuna-Werke) describes a process for the preparation of polyethylenepolyamines directly from ammonia and ethylene oxide by reaction in a staggered temperature pressure reactor for the uncatalyzed reaction of ammonia with ethylene oxide and for the metal-catalyzed amination of Monoethanolamine.
  • the reaction product is a polyamine mixture.
  • EP-A 1-75 940 and EP-A1-75 941 both UCC relate to the preparation of ethylenediamine or polyethylene polyamines by reacting ethylene oxide with ammonia and subsequent amination of the resulting ethanolamines.
  • the procedures involve the recycling of unreacted MEOA after separation from the monoethanolamine (MEOA) amination product mixture to the amination reactor to ensure sufficient excess of MEOA for amination to drive back amination of the co-products DEOA and TEOA. Although this makes it possible to achieve a sufficient conversion of the fresh MEOA supplied, the quantities of the secondary components DEOA and TEOA produced are not reduced. The space-time yield of the MEOA reaction decreases and the amination of DEOA and TEOA can not be completely suppressed.
  • MEOA monoethanolamine
  • the conventional water-catalyzed NH 3 -EO reaction provides only a kinetically controlled MEOA, DEOA, TEOA mix with a very high proportion of DEOA and TEOA. Even with NH 3 / EO molar ratios up to 40: 1, maximum product mixtures comprising MEOA, DEOA and TEOA in the weight ratio 70 - ⁇ 80: 10 - 20: 2-5 are obtained by conventional processes.
  • the present invention has for its object, overcoming one or more disadvantages of the prior art, to find an improved economical process for the production of ethylene amines.
  • the process should be based on the starting material ethylene oxide and an intermediate isolation of monoethanolamine should not take place.
  • the process should provide especially ethylenediamine with high space-time yield and selectivity and the catalysts have a long service life.
  • EO ethylene oxide
  • DEOA Diethanolamine
  • TEOA triethanolamine
  • the ethyleneamines are, in particular, ethylenediamine (EDA), diethylenetriamine (DETA), aminoethylethanolamine (AEEA), piperazine (PIP) and / or triethylenetetramine (TETA).
  • EDA ethylenediamine
  • DETA diethylenetriamine
  • AEEA aminoethylethanolamine
  • PIP piperazine
  • TETA triethylenetetramine
  • the procedure can be carried out as follows.
  • Ethylene oxide (EO) is continuously fed together with ammonia into a reactor, preferably tubular reactor.
  • the molar ratio of EO to NH 3 is preferably in the range from 1:10 to 30, in particular from 1:15 to 29, especially from 1:20 to 28, very particularly from 1: 23 to 27, for example from 1:25.
  • the heterogeneous catalyst is an inorganic ion exchanger. The catalyst is preferably arranged in the reactor as a fixed bed.
  • the inorganic ion exchanger is preferably a silicate, in particular a framework silicate and / or sheet silicate, e.g. as described in the "Textbook of Inorganic Chemistry” (Holleman-Wiberg), 91st-100th Edition, 1985, at pages 771-778.
  • Preferred examples of framework silicates are feldspars and zeolites.
  • Preferred examples of sheet silicates are clay minerals such as bentonite, montmorillonite (e.g., K10) or saponite.
  • the inorganic ion exchanger is preferably used as a shaped body.
  • All known and / or suitable kneading and shaping devices or methods can be used. Among others, these include:
  • pelleting i. Compacting by circular and / or rotating motions
  • sintering i. the material to be deformed is subjected to a thermal treatment.
  • the shaping may be selected from the following group, the combination of at least two of these methods being explicitly included: briquetting by stamping presses, roll pressing, ring roll pressing, briquetting without binder;
  • the proportion of the inorganic ion exchanger in the catalyst molding is preferably at least 5 wt .-%, in particular at least 10 wt .-%, particularly preferably at least 50 wt .-%.
  • the pore volume of the shaped catalyst bodies for pores having diameters in the range from 2 nm to 10 ⁇ m, measured by means of Hg porosimetry according to DIN 66134, is preferably in the range from 0.1 to 1.5 cm 3 / g, particularly preferably in the range from 0.3 to 1.0 cm 3 / g.
  • the reaction of the ethylene oxide to MEOA, DEOA and TEOA provides particularly favorable product mixtures for the subsequent amination of the alcohol when it is carried out on a scandium, yttrium and / or lanthanide-doped catalyst molding.
  • the shaped body contains one or more metals in the oxidation state III, selected from scandium, yttrium and / or the lanthanides (such as lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolium, terbium, dysprosium, Holmium, erbium, thulium, ytterbium, lutetium).
  • the lanthanides such as lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolium, terbium, dysprosium, Holmium, erbium, thulium, ytterbium, lutetium.
  • metals are preferably in the range from 0.5 to 50% by weight, in particular from 1 to 30% by weight, in particular from 7 to 15% by weight (in each case based on the silicate weight).
  • the reaction is preferably carried out at an absolute pressure in the range of 50 to
  • 150 bar especially 90 to 110 bar, and preferably at a temperature in the range of
  • the LHSV of the reactor is preferably in the range of 5 to 15 I / 1 (catalyst) • h, in particular in the range of 7 to 12 1/1 (K ata ysator l) * h.
  • MEOA monoethanolamine
  • DEOA diethanolamine
  • TEOA triethanolamine
  • Typical weight ratios are, depending on the NH 3 : EO molar ratio (MV) used:
  • the reactor is, preferably without relaxation and preferably without cooling, with hydrogen (eg 0.01 to 10 wt .-% based on the total feed) and in a second reactor, preferably tubular reactor, driven.
  • a mixing section can be installed in front of the second reactor.
  • the heterogeneous hydrogenation catalyst in the second reaction stage preferably contains one or more metals selected from Ni, Co, Cu, Ru, Re, Pd and / or Pt on a support selected from Al 2 O 3 , TiO 2 , ZrO 2 and / or SiO 2 .
  • the catalyst is preferably arranged in the reactor as a fixed bed.
  • catalyst is an amination catalyst, for example a catalyst containing Ni, Co and Cu on an oxidic support, such as Al 2 O 3 , ZrO 2 , SiO 2 .
  • catalysts used in the second reaction stage are the catalysts disclosed in DE-A-19 53 263 (BASF AG) containing cobalt, nickel and copper and aluminum oxide and / or silicon dioxide having a metal content of from 5 to 80% by weight %, in particular 10 to 30 wt .-%, based on the total catalyst, wherein the catalysts, calculated on the metal content, 70 to 95 wt .-% of a mixture of cobalt and nickel and 5 to 30 wt .-% copper and wherein the weight ratio of cobalt to nickel 4: 1 to 1: 4, in particular 2: 1 to 1: 2, for example, the catalyst used in the examples there with the composition 10 wt .-% CoO, 10 wt. % NiO and 4 wt.% CuO on Al 2 O 3 .
  • the reductive amination is preferably carried out at an absolute pressure in the range of 150 to 250 bar, in particular 170 to 220 bar, and preferably at a temperature in the range of 160 to 22O 0 C, especially 170 to 21O 0 C.
  • connection between the reactors of the two reaction stages is sufficiently isolated, preheating before the second reactor stage is not necessary. However, the reaction can be run within the described reaction temperatures at freely selectable temperature differences between the first and second reactor.
  • a metered addition of NH 3 before the second reactor stage is not necessary to produce a customary product mixture of ethylene amines (ethylenediamine, diethylenetriamine, piperazine, aminoethylethanolamine, diethanolamine, triethanolamine, etc.), but can optionally be used to increase the proportion of lower ethyleneamines (ethylenediamine, diethylenetriamine). be performed.
  • ethylene amines ethylenediamine, diethylenetriamine, piperazine, aminoethylethanolamine, diethanolamine, triethanolamine, etc.
  • the amination of the MEOA-DEOA-TEOA mixture from the EO reaction of the first reaction stage is preferably not driven to the full conversion of the three ethanolamines in order to increase the proportion of linear, lower ethyleneamines (ie EDA, DETA, AEEA). hen. Instead, preferred ranges of turnover of 50 to 80% are set with respect to MEOA. Under these conditions, DEOA and TEOA are only partially converted, about 30% of the DEOA are converted into the value product AEEA. In addition, no increased proportion of morpholine, hydroxyethylpiperazine and hydroxy-ethlylmorpholin is formed, which could lead to difficulties in the distillative workup due to relatively low boiling points.
  • the reaction product of the process according to the invention contains ethylenediamine, diethylenetriamine, piperazine, triethylenetetramine, aminoethylethanolamine and higher cyclic and linear ethylene amines on amination products.
  • unreacted MEOA, DEOA and TEOA are obtained.
  • a typical reaction effluent in the event that MEOA is not recycled to the amination reactor, additionally contains 25-50% by weight of MEOA and EDA, DETA, AEEA, PIP and DEOA in the proportions indicated above.
  • the separation of the products is preferably carried out by distillation, being separated after increasing boiling point NH 3 , H 2 O, ethylenediamine, piperazine, monoethanolamine, diethylenetriamine, aminoethylethanolamine and DEOA.
  • NH 3 is preferably reduced to the EO conversion (first reaction stage).
  • Unreacted MEOA can be recycled with the linear and cyclic ethylene amines and aminoethylethanolamine as co-product or the MEOA is recycled and thus the overall yield of the amination compared to the Alcohols increased.
  • the recycling may optionally be done before the first (EO amination) or second (alcohol amination) reactor stage
  • Appendix 2 is a scheme for a process variant according to the invention with MEOA feedback.
  • Example 1 Coupled production of ethylene amines and MEOA
  • the mixture is admixed with hydrogen (1 g / h) and run in a second reactor (for example: volume 190 ml, length 1000 cm, diameter 1 cm).
  • the amination is carried out on a Ni, Co, Cu catalyst on Al 2 O 3 (10 wt .-% CoO, 10 wt .-% NiO and 4 wt .-% CuO to Al 2 O 3 ) (LHSV -4, 5 h "1), at a pressure of 200 bar and a temperature in the range of 170-210 0 C.
  • EDA 38 g / h
  • DETA 6 g / h
  • Piperazine 4 g / h
  • AEEA 5 g / h
  • the MEOA (21 g / h) obtained in this otherwise analogous variant is completely recycled to the second reactor (amination reactor).
  • the catalyst used in the EO reaction is a montmorillonite doped with 10% by weight of lanthanum (analogous to EP-A-652 207, Catalyst E).
  • the bottom of the DEOA column is not further separated.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de production d'amines d'éthylène. Dans une première étape de réaction, on convertit en continu de l'oxyde d'éthylène (EO) avec de l'ammoniaque dans des conditions exemptes d'eau au niveau d'un échangeur d'ions inorganiques en tant que catalyseur hétérogène. Le produit de réaction résultant contient de l'amine de monoéthanol (MEOA), de l'amine de diéthanol (DEOA) et de l'amine de triéthanol (TEOA) dans un rapport en poids MEOA: DEOA: TEOA = 80 - 94: 5,9 - 15: 0,1 5. Ensuite, le produit de réaction est ensuite converti en continu dans un deuxième étage de conversion avec de l'ammoniaque en présence d'hydrogène et un catalyseur d'hydrogénation hétérogène.
PCT/EP2006/061823 2005-04-26 2006-04-25 Procede de production d'amines d'ethylene WO2006114417A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005019373.0 2005-04-26
DE200510019373 DE102005019373A1 (de) 2005-04-26 2005-04-26 Verfahren zur Herstellung von Ethylenaminen

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WO2006114417A2 true WO2006114417A2 (fr) 2006-11-02
WO2006114417A3 WO2006114417A3 (fr) 2007-01-11

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Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7615665B2 (en) 2005-09-30 2009-11-10 Basf Se Method for producing ethylene amines
US7635790B2 (en) 2006-02-14 2009-12-22 Basf Se Method for producing ethylene amines and ethanol amines by the hydrogenating amination of monoethylene glycol and ammonia in the presence of a catalyst
US7696384B2 (en) 2005-09-30 2010-04-13 Basf Se Process for producing ethyleneamines
WO2010042168A2 (fr) 2008-10-06 2010-04-15 Dow Global Technologies Inc. Procédés de fabrication d'éthanolamine(s) et d'éthylèneamine(s) à partir d'oxyde d'éthylène et d'ammoniac, et procédés associés
US7700806B2 (en) 2006-02-14 2010-04-20 Basf Aktiengesellschaft Method for producing ethylene amines ethanol amines from monoethylene glycol (MEG)
US8188318B2 (en) 2008-10-06 2012-05-29 Union Carbide Chemicals & Plastics Technology Llc Method of manufacturing ethyleneamines
US8187997B2 (en) 2008-10-06 2012-05-29 Union Carbide Chemicals & Technology LLC Low metal loaded, catalyst compositions including acidic mixed metal oxide as support
WO2012087553A1 (fr) 2010-12-21 2012-06-28 Dow Global Technologies Llc Procédés permettant de séparer un ou plusieurs sous-produits aminés d'une ou de plusieurs amines souhaitées
CN102617363A (zh) * 2012-03-13 2012-08-01 河北科技大学 一种乙二胺和环氧乙烷合成羟乙基乙二胺的新工艺
US8293676B2 (en) 2008-10-06 2012-10-23 Union Carbide Chemicals & Plastics Technology Llc Low metal loaded, alumina supported, catalyst compositions and amination process
CN102782002A (zh) * 2010-03-02 2012-11-14 巴斯夫欧洲公司 线性三亚乙基四胺作为环氧树脂固化剂的用途
WO2013182468A1 (fr) 2012-06-06 2013-12-12 Basf Se Procédé de production de pipérazine
WO2013182465A1 (fr) 2012-06-06 2013-12-12 Basf Se Procédé de production de pipérazine
US8637668B2 (en) 2010-06-15 2014-01-28 Basf Se Process for preparing a cyclic tertiary methylamine
US8884015B2 (en) 2012-06-01 2014-11-11 Basf Se Process for the preparation of a mono-N-alkypiperazine
US8927712B2 (en) 2012-06-01 2015-01-06 Basf Se Process for the preparation of a mono-N-alkylpiperazine
US8933223B2 (en) 2010-10-14 2015-01-13 Basf Se Process for preparing a cyclic tertiary amine
US8981093B2 (en) 2012-06-06 2015-03-17 Basf Se Process for preparing piperazine
WO2016139594A1 (fr) 2015-03-05 2016-09-09 Sabic Global Technologies B.V. Systèmes et procédés se rapportant à la production d'oxyde d'éthylène, d'éthylène glycol et/ou d'éthanolamines
CN106608825A (zh) * 2015-10-22 2017-05-03 中国石油化工股份有限公司 乙醇胺法生产乙二胺的方法
US9783486B2 (en) 2013-12-02 2017-10-10 Dow Global Technologies Llc Preparation of high molecular weight, branched, acyclic polyalkyleneamines and mixtures thereof
JP2021500389A (ja) * 2017-10-27 2021-01-07 ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ エチレンアミンの製造方法
CN115010611A (zh) * 2022-04-27 2022-09-06 北京金隅水泥节能科技有限公司 一种二乙醇单异丙醇胺的生产工艺

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JP5897904B2 (ja) 2008-10-06 2016-04-06 ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー エルエルシー 環状、ｎ−アミノ官能性トリアミンの生成方法
EP2883862A1 (fr) * 2013-12-10 2015-06-17 Basf Se Procédé de fabrication d'amines

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DE1953263A1 (de) * 1969-10-23 1972-02-17 Basf Ag Verfahren zur Herstellung von Aminen aus Alkoholen
EP0075940A1 (fr) * 1981-09-30 1983-04-06 Union Carbide Corporation Procédé pour la fabrication d'éthylènediamine
EP0652207A1 (fr) * 1993-11-02 1995-05-10 Nippon Shokubai Co., Ltd. Procédé de préparation d'aminoalcanol, catalyseur pour la mise en oeuvre de ce procédé et préparation du catalyseur

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Publication number Priority date Publication date Assignee Title
DE1953263A1 (de) * 1969-10-23 1972-02-17 Basf Ag Verfahren zur Herstellung von Aminen aus Alkoholen
EP0075940A1 (fr) * 1981-09-30 1983-04-06 Union Carbide Corporation Procédé pour la fabrication d'éthylènediamine
EP0652207A1 (fr) * 1993-11-02 1995-05-10 Nippon Shokubai Co., Ltd. Procédé de préparation d'aminoalcanol, catalyseur pour la mise en oeuvre de ce procédé et préparation du catalyseur

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7696384B2 (en) 2005-09-30 2010-04-13 Basf Se Process for producing ethyleneamines
US7615665B2 (en) 2005-09-30 2009-11-10 Basf Se Method for producing ethylene amines
US7635790B2 (en) 2006-02-14 2009-12-22 Basf Se Method for producing ethylene amines and ethanol amines by the hydrogenating amination of monoethylene glycol and ammonia in the presence of a catalyst
US7700806B2 (en) 2006-02-14 2010-04-20 Basf Aktiengesellschaft Method for producing ethylene amines ethanol amines from monoethylene glycol (MEG)
US8293676B2 (en) 2008-10-06 2012-10-23 Union Carbide Chemicals & Plastics Technology Llc Low metal loaded, alumina supported, catalyst compositions and amination process
WO2010042168A2 (fr) 2008-10-06 2010-04-15 Dow Global Technologies Inc. Procédés de fabrication d'éthanolamine(s) et d'éthylèneamine(s) à partir d'oxyde d'éthylène et d'ammoniac, et procédés associés
WO2010042168A3 (fr) * 2008-10-06 2010-10-07 Dow Global Technologies Inc. Procédés de fabrication d'éthanolamine(s) et d'éthylèneamine(s) à partir d'oxyde d'éthylène et d'ammoniac, et procédés associés
US8188318B2 (en) 2008-10-06 2012-05-29 Union Carbide Chemicals & Plastics Technology Llc Method of manufacturing ethyleneamines
US8187997B2 (en) 2008-10-06 2012-05-29 Union Carbide Chemicals & Technology LLC Low metal loaded, catalyst compositions including acidic mixed metal oxide as support
CN102239134B (zh) * 2008-10-06 2014-04-16 陶氏环球技术有限责任公司 由环氧乙烷和氨制造乙醇胺类和1，2-亚乙基胺类的方法及相关方法
EP2487151A1 (fr) 2008-10-06 2012-08-15 Dow Global Technologies LLC Procédés de séparation d'alkyléthylèneamine(s) d'une composition d'éthylèneamine(s)
CN102782002A (zh) * 2010-03-02 2012-11-14 巴斯夫欧洲公司 线性三亚乙基四胺作为环氧树脂固化剂的用途
US8637668B2 (en) 2010-06-15 2014-01-28 Basf Se Process for preparing a cyclic tertiary methylamine
US8933223B2 (en) 2010-10-14 2015-01-13 Basf Se Process for preparing a cyclic tertiary amine
WO2012087553A1 (fr) 2010-12-21 2012-06-28 Dow Global Technologies Llc Procédés permettant de séparer un ou plusieurs sous-produits aminés d'une ou de plusieurs amines souhaitées
US8895785B2 (en) 2010-12-21 2014-11-25 Dow Global Technologies Llc Processes for separating one or more amine byproducts from one or more desired amines
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