KR960037640A - 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법 - Google Patents

아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법 Download PDF

Info

Publication number
KR960037640A
KR960037640A KR1019950009689A KR19950009689A KR960037640A KR 960037640 A KR960037640 A KR 960037640A KR 1019950009689 A KR1019950009689 A KR 1019950009689A KR 19950009689 A KR19950009689 A KR 19950009689A KR 960037640 A KR960037640 A KR 960037640A
Authority
KR
South Korea
Prior art keywords
amination reaction
nickel
reaction catalyst
reduction amination
aminoethylethanolamine
Prior art date
Application number
KR1019950009689A
Other languages
English (en)
Other versions
KR100216935B1 (ko
Inventor
웨인 킹 스티븐
Original Assignee
카렌 엘. 존슨
유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀로지 코포레이션
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to EP95302456A priority Critical patent/EP0737669B1/en
Priority to DE69512381T priority patent/DE69512381T2/de
Priority to CA002146903A priority patent/CA2146903C/en
Priority to MX9501842A priority patent/MX9501842A/es
Application filed by 카렌 엘. 존슨, 유니온 카바이드 케미칼즈 앤드 플라스틱스 테크놀로지 코포레이션 filed Critical 카렌 엘. 존슨
Priority to KR1019950009689A priority patent/KR100216935B1/ko
Priority to JP7125620A priority patent/JP2876464B2/ja
Priority to US08/461,549 priority patent/US5600000A/en
Priority to US08/465,186 priority patent/US5891820A/en
Publication of KR960037640A publication Critical patent/KR960037640A/ko
Application granted granted Critical
Publication of KR100216935B1 publication Critical patent/KR100216935B1/ko

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/14Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/007Mixed salts
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/889Manganese, technetium or rhenium
    • B01J23/8896Rhenium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20Carbon compounds
    • B01J27/232Carbonates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14Preparation 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
    • C07C209/16Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/26Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/582Recycling of unreacted starting or intermediate materials

Landscapes

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

Abstract

본 발명은 모노에탄올아민과 암모니아를 수소와 다양한 환원 아민화 반응 촉매의 존재하에서 반응시켜 아미노에틸에탄올 아민과 같은 아사이클릭 생성물에 대한 높은 선택도를 수득하고 피페라진과 같은 사이클릭 생성물의 생성을 감소시키는 개선된 환원 아민화 반응법에 관한 것이다. 본 발명의 방법을 전이 알루미나 담체위에 니켈 또는 니켈-레늄과 같은 금속을 함유하는 환원 아민화 반응 촉매의 존재하에서 수행하는 경우, 목적하는 생산물에 대한 생산성과 선택도가 증가한다. 또한 본 방법은 촉진제의 사용에 의해 성능이 향상되는 하이드로탈사이트계 또는 타코바이트계 촉매의 존재하에서 수행하여 목적하는 결과를 달성할 수 있다.

Description

아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 암모니아, 수소 및 전이 알루미나 담체에 혼입시킨 하나 이상의 촉매 작용성 환원 아민화 금속을 포함하는 환원 아민화 반응 촉매(여기서, 니켈 대 레늄의 원자비는 약 1 : 1 내지 약 200 : 1이다)의 존재하에 모노에탄올아민(MEA)을 반응시켜, 피페라진에 대해 아미노에틸에탄올아민량이 증가된 생성 혼합물을 수득함을 포함하는 환원 아민화 반응법.
  2. 제1항에 있어서, 촉매 작용성 환원 아민화 금속이 니켈, 레늄, 코발트, 로듐, 이리듐, 루테늄, 팔라듐 및 백금으로 이루어진 그룹으로부터 선택되는 방법.
  3. 제1항에 있어서, 전이 알루미나 담체가 델타상, 쎄타상, 감마/쎄타상, 델타/쎄타상, 쎄타/알파상 및 이들의 혼합물로 이루어진 그룹으로부터 선택되는 방법.
  4. 제1항에 있어서, 환원 아민화 반응 촉매가 주기율표의 ⅠA족, ⅡA족 및 ⅡB족으로부터 선택되는 원소를 함유하는 화합물로 이루어진 그룹으로부터 선택되는 촉진제를 추가로 포함하는 방법.
  5. 제4항에 있어서, 촉진제가 마그네슘, 아연 또는 이들의 혼합물인 방법.
  6. 암모니아, 수소 및, 일반식〔Mx 2+My 3+(OH)2x+2y〕〔Ay/n n-〕·zH2O의 물질〔여기서, Mx 2+는 마그네슘이고 ; My3+는 알루미늄이고 ; A는 n-가의 탄산염이고 ; n은 1 이상〔예를 들면, 1 내지 4, 주로 1 내지 3)이고 ; z는 양수이다〕과 추가로 니켈 촉진제를 포함하는 환원 아민화 반응 촉매의 존재하에서 MEA를 반응시켜, 피페라진에 대해 아미노에틸에탄올아민량이 증가된 생성 혼합물을 수득함을 포함하는 환원 아민화 반응법.
  7. 암모니아, 수소 및, 일반식〔Mx 2+My 3+(OH)2x+2y〕〔Ay/n n-〕·zH2O의 물질〔여기서, Mx 2+는 니켈이고 ; My 3+는 알루미늄이고 ; A는 n-가의 탄산염이고 ; n은 1 이상〔예를 들면, 1 내지 4, 주로 1 내지 3)이고 ; z는 양수이다〕을 포함하는 환원 아민화 반응 촉매의 존재하에서 MEA를 반응시켜, 피페라진에 대해 아미노에탄올 아민량이 증가된 생성 혼합물을 수득함을 포함하는 환원 아민화 반응법.
  8. 제7항에 있어서, 환원 아민화 반응 촉매가 레늄 금속을 추가로 포함하는 방법.
  9. 일반식〔Mx 2+My 3+(OH)2x+2y〕〔Ay/n n-〕·zH2O의 물질〔여기서, Mx 2+는 니켈이고 ; My 3+는 알루미늄이고 ; A는 n-가의 탄산염이고 ; n은 1 이상〔예를 들면, 1 내지 4, 주로 1 내지 3)이고 ; z는 양수이다〕과 추가로 레늄 금속을 포함하는, 아미노에틸에탄올아민(AEEA)의 선택적 제조용 환원 아민화 반응 촉매.
  10. 일반식〔Mx 2+My 3+(OH)2x+2y〕〔Ay/n n-〕·zH2O의 물질〔여기서, Mx 2+는 마그네슘이고 ; My 3+는 알루미늄이고 ; A는 n-가의 탄산염이고 ; n은 1 이상 (예를 들면, 1 내지 4, 주로 1 내지 3)이고 ; z는 양수이다〕과 추가로 니켈 또는 니켈/레늄 촉진제를 포함하는, AEEA의 선택적 제조용 환원 아민화 반응 촉매.
    ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
KR1019950009689A 1993-12-22 1995-04-25 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법 KR100216935B1 (ko)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EP95302456A EP0737669B1 (en) 1993-12-22 1995-04-12 Reductive amination processes for the selective production of aminoethylethanolamine
DE69512381T DE69512381T2 (de) 1993-12-22 1995-04-12 Reduktive Aminierung zur selektiven Herstellung von Aminoethylethanolamin
CA002146903A CA2146903C (en) 1993-12-22 1995-04-12 Reductive amination catalysts for the selective production of aminoethylethanolamine
MX9501842A MX9501842A (es) 1993-12-22 1995-04-19 Procesos de aminacion reductivos para la produccion selectiva de aminoetiletanolamina.
KR1019950009689A KR100216935B1 (ko) 1993-12-22 1995-04-25 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법
JP7125620A JP2876464B2 (ja) 1993-12-22 1995-04-27 アミノエチルエタノールアミンを選択的に製造するための還元アミノ化方法
US08/461,549 US5600000A (en) 1993-12-22 1995-06-05 Reductive amination processes for the selective production of amino-ethylethanolamine
US08/465,186 US5891820A (en) 1993-12-22 1995-06-05 Reductive amination processes for the selective production of amino-ethyylethanolamine

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US17153993A 1993-12-22 1993-12-22
EP95302456A EP0737669B1 (en) 1993-12-22 1995-04-12 Reductive amination processes for the selective production of aminoethylethanolamine
CA002146903A CA2146903C (en) 1993-12-22 1995-04-12 Reductive amination catalysts for the selective production of aminoethylethanolamine
MX9501842A MX9501842A (es) 1993-12-22 1995-04-19 Procesos de aminacion reductivos para la produccion selectiva de aminoetiletanolamina.
KR1019950009689A KR100216935B1 (ko) 1993-12-22 1995-04-25 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법
JP7125620A JP2876464B2 (ja) 1993-12-22 1995-04-27 アミノエチルエタノールアミンを選択的に製造するための還元アミノ化方法
US08/465,186 US5891820A (en) 1993-12-22 1995-06-05 Reductive amination processes for the selective production of amino-ethyylethanolamine

Publications (2)

Publication Number Publication Date
KR960037640A true KR960037640A (ko) 1996-11-19
KR100216935B1 KR100216935B1 (ko) 1999-10-01

Family

ID=32097192

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019950009689A KR100216935B1 (ko) 1993-12-22 1995-04-25 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법

Country Status (7)

Country Link
US (1) US5891820A (ko)
EP (1) EP0737669B1 (ko)
JP (1) JP2876464B2 (ko)
KR (1) KR100216935B1 (ko)
CA (1) CA2146903C (ko)
DE (1) DE69512381T2 (ko)
MX (1) MX9501842A (ko)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19706876A1 (de) * 1997-02-21 1998-08-27 Basf Ag Verfahren zur Herstellung von Carbonsäuren oder deren Estern durch Carbonylierung von Olefinen
SE513250C2 (sv) * 1997-11-11 2000-08-07 Akzo Nobel Nv Amineringsförfarande för framställning av polyaminer
US6534441B1 (en) * 1999-03-06 2003-03-18 Union Carbide Chemicals & Plastics Technology Corporation Nickel-rhenium catalyst for use in reductive amination processes
DE10028432A1 (de) * 2000-06-13 2001-12-20 Basell Polyolefine Gmbh Auf calciniertes Hydrotalcit geträgerter Katalysatorfeststoff zur Olefinpolymerisation
DE10349059A1 (de) * 2003-10-17 2005-05-19 Basf Ag Verfahren zur destillativen Auftrennung von Gemischen enthaltend Ethylenamine
JP4972315B2 (ja) * 2005-12-28 2012-07-11 花王株式会社 含窒素化合物の製造方法
CN101910107B (zh) 2008-01-03 2013-03-13 阿克佐诺贝尔股份有限公司 制备亚乙基胺的方法
WO2010042164A2 (en) 2008-10-06 2010-04-15 Union Carbide Chemicals & Plastics Technology Llc Transalkoxylation of nucleophilic compounds
WO2010042157A1 (en) 2008-10-06 2010-04-15 Union Carbide Chemicals & Plastics Technology Llc Low metal loaded, alumina supported, catalyst compositions and amination process
WO2010042160A1 (en) 2008-10-06 2010-04-15 Union Carbide Chemicals & Plastics Technology Llc A process to selectively manufacture diethylenetriamine (deta) or other desirable ethylenamines via continuous transamination of ethylenediamine (eda), and other ethyleneamines over a heterogeneous catalyst system
BRPI0914054A2 (pt) 2008-10-06 2015-11-03 Union Carbide Chem Plastic método para produzir etilenoaminas
JP5480276B2 (ja) 2008-10-06 2014-04-23 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 担体として酸性混合金属酸化物を含む低金属(ニッケル及びレニウム)触媒組成物
BRPI0914085A2 (pt) 2008-10-06 2015-10-27 Dow Global Technologies Llc processo para a produção de uma ou mais etanolaminas e uma ou mais etilenoaminas e processo para separar uma ou mais alquiletilenodiaminas de etilenodiamina
CN102227413B (zh) 2008-10-06 2014-11-05 联合碳化化学品及塑料技术公司 制备环状n-氨基官能化三胺的方法
BR112014015064A2 (pt) * 2011-12-22 2017-06-13 Dow Global Technologies Llc método para preparar composição contendo piperazina e aminoetiletanolamina
EP2797901B1 (en) 2011-12-29 2017-05-10 Dow Global Technologies Llc Formation of higher molecular weight cyclic polyamine compounds from cyclic polyamine compounds
PL2797902T3 (pl) 2011-12-29 2017-09-29 Dow Global Technologies Llc Kompozycje zawierające cykliczne związki aminowe i wytworzone z nich pianki poliuretanowe
US9611351B2 (en) 2011-12-29 2017-04-04 Dow Global Technologies Llc. Amine polyether polyols and polyurethane foam compositions made from cyclic amine compounds
JP2017500386A (ja) 2013-12-02 2017-01-05 ダウ グローバル テクノロジーズ エルエルシー 高分子量の分岐鎖非環式ポリアルキレンアミン及びその混合物の調製
CN107075995B (zh) 2014-09-03 2019-09-10 康宁股份有限公司 具有分层塞子的蜂窝体及其制造方法
CN114315613B (zh) * 2021-12-27 2024-03-19 江苏康恒化工有限公司 一种羟乙基乙二胺的合成工艺

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4123462A (en) * 1976-01-07 1978-10-31 Union Carbide Corporation Amination process using nickel-rhenium catalysts
GB8707304D0 (en) * 1987-03-26 1987-04-29 Bp Chem Int Ltd Chemical process
US5202490A (en) * 1987-09-30 1993-04-13 Union Carbide Chemicals & Plastics Technology Corporation Process for thr manufacture of diethylenetriamine and aminoethylethanolamine
US5352835A (en) * 1993-02-08 1994-10-04 Texaco Chemical Company Supported catalysts for amination
US5340466A (en) * 1993-04-19 1994-08-23 Texaco Inc. Hydrodesulfurization of cracked naphtha with hydrotalcite-containing catalyst

Also Published As

Publication number Publication date
JP2876464B2 (ja) 1999-03-31
KR100216935B1 (ko) 1999-10-01
EP0737669B1 (en) 1999-09-22
MX197579B (ko) 2000-07-18
MX9501842A (es) 1997-04-30
CA2146903A1 (en) 1996-10-13
JPH08319261A (ja) 1996-12-03
US5891820A (en) 1999-04-06
EP0737669A1 (en) 1996-10-16
DE69512381D1 (de) 1999-10-28
CA2146903C (en) 2000-01-25
DE69512381T2 (de) 2000-04-06

Similar Documents

Publication Publication Date Title
KR960037640A (ko) 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법
US5773657A (en) Hydrogenation of aromatic compounds in which at least one amino group is bonded to an aromatic nucleus
KR850002822A (ko) 아세틸렌의 수소화방법
KR960037115A (ko) 개선된 환원성 아민화 촉매
JP5124486B2 (ja) 触媒の存在でモノエチレングリコール及びアンモニアの水素化アミノ化によるエチレンアミン及びエタノールアミンの製造方法
CN1927794B (zh) 丙酮的氢化
EP0034480A2 (en) Alkylation of amines
US3644522A (en) Catalytic hydrogenation of nitrogen containing compounds over supported ruthenium catalysts
RU2215734C2 (ru) Способ аминирования
DE19507007A1 (de) Katalysatoren für die Aminierung von Alkoholen, Ketonen und Aldehyden
Trotta et al. Selective mono-N-alkylation of aromatic amines by dialkyl carbonate under gas-liquid phase-transfer catalysis (GL-PTC) conditions
JPS60130551A (ja) 第3級アミンの製造方法
JP5426362B2 (ja) 高汚染メチレンジアニリンの水素化方法
US4053515A (en) Catalytic hydrogenation of unsaturated dinitriles employing high purity alumina
KR890002429B1 (ko) 히드록시 알킬 아민 및 히드록시 알킬 피페라진의 제조 방법
US3880929A (en) Catalytic hydrogenation of unsaturated dinitriles
EP0618895B1 (en) Process for the preparation of an aminonitrile by partial hydrogenation of a nitrile compound with two or more nitrile groups
CA1065343A (en) Preparation of tertiary amines
EP0618188B1 (en) Process for the preparation of cyclohexylamines by catalytic hydrogenation of anilines
SU427925A1 (ru) Способ получения ксилилендиамина или цианбензиламина
JPH0417942B2 (ko)
GB2044759A (en) Hydrogenation of aromatic bis - methyl - amines
US6121493A (en) Isomerization of cyclohexylamines to produce their thermodynamic isomeric form
Labadie et al. Selective catalytic syntheses of mixed alkyl amines
US6140540A (en) Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts

Legal Events

Date Code Title Description
A201 Request for examination
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
LAPS Lapse due to unpaid annual fee