KR970706237A - 방향족 아민의 수소화 속도를 향상시키는 방법(Method of increasing hyrogenation rate of aromatic amines) - Google Patents
방향족 아민의 수소화 속도를 향상시키는 방법(Method of increasing hyrogenation rate of aromatic amines)Info
- Publication number
- KR970706237A KR970706237A KR1019970701701A KR19970701701A KR970706237A KR 970706237 A KR970706237 A KR 970706237A KR 1019970701701 A KR1019970701701 A KR 1019970701701A KR 19970701701 A KR19970701701 A KR 19970701701A KR 970706237 A KR970706237 A KR 970706237A
- Authority
- KR
- South Korea
- Prior art keywords
- weight
- water
- aromatic amine
- amount
- increasing
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/36—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
- C07C209/72—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines by reduction of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
Landscapes
- 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
부산물의 총량을 현저하게 증가시키지 않으면서 수소화 반응 속도를 향상시키기 위하여 유효량의 귀금속 촉매, 수혼화성 유기 용매, 수산화리튬 촉매 촉진제 및 물의 존재하에서 방향족 아민과 수소를 반응시켜 방향족 아민의 촉매 수소화 반응 속도를 향상시키는 방법.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 화학식(1)의 방향족 아민을 포함하는 반응 혼합물(이는, 이의 중량을 기준으로 하여, 물을 7 내지 12중량%의 양으로 함유한다)을 귀금속 촉매, 수산화리튬 촉매 촉진제 및 수혼화성 수성 유기 용매의 존재하에 약 500 내지 약 4000psig의 압력에서 수소와 반응시킴을 포함하여, 화학식(1)의 방향족 아민을 촉매 수소화하는 방법.상기 화학식(1)에서 R1은 H, 탄소수 1 내지 6의 알킬 또는 사이클로알킬 그룹 및 NH2로 이루어진 그룹으로부터 선택되며, R2는 H, 탄소수 1 내지 6의 알킬 또는 사이클로 알킬 그룹 및로 이루어진 그룹으로부터 선택되고, R3및 R4는 H 및 탄소수 1 내지 6의 알킬 또는 사이클로알킬로 이루어진 그룹으로부터 선택된다.
- 제1항에 있어서, 물이, 반응 혼합물의 중량을 기준으로 하여, 7 내지 12중량%의 양으로 존재하는 방법.
- 제2항에 있어서, 물이, 반응 혼합물의 중량을 기준으로 하여, 7 내지 10중량%의 양으로 존재하는 방법.
- 제1항에 있어서, R1,R3및 R4가 H이고 R2가인 방법.
- 제1항에 있어서, 수산화리튬 촉매 촉진제가 방향족 아민의 약 0.01 내지 약 2중량%의 농도로 존재하는 방법.
- 제1항에 있어서, 수산화리튬 촉매 촉진제가 방향족 아민의 약 0.1 내지 약 1중량%의 양으로 존재하는 방법.
- 제1항에 있어서, 귀금속 촉매가 Ru/Al2O3인 방법.
- 제1항에 있어서, 이소프로필 알콜이 수혼화성 유기 영매로서 사용되는 방법.
- 제1항에 있어서, 반응이 약 110 내지 약 120℃의 온도 범위에서 수행되는 방법.
- 방향족 아민(a), 귀금속 촉매(b), 촉매 촉진제로서의 수산화리튬(c) 및 조성물의 중량을 기준으로 하여 7 내지 12중량%의 양으로 물을 함유하는 수혼화성 유기용매(d)를 포함하는, 방향족 아민의 촉매 수소화 반응에 유용한 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/307,215 | 1994-09-16 | ||
US08/307,215 US5550294A (en) | 1992-02-05 | 1994-09-16 | Method of increasing hydrogenation rate of aromatic amines |
PCT/US1995/010851 WO1996008462A1 (en) | 1994-09-16 | 1995-08-28 | Method of increasing hydrogenation rate of aromatic amines |
Publications (1)
Publication Number | Publication Date |
---|---|
KR970706237A true KR970706237A (ko) | 1997-11-03 |
Family
ID=23188757
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019970701701A KR970706237A (ko) | 1994-09-16 | 1995-08-28 | 방향족 아민의 수소화 속도를 향상시키는 방법(Method of increasing hyrogenation rate of aromatic amines) |
Country Status (8)
Country | Link |
---|---|
US (1) | US5550294A (ko) |
EP (1) | EP0781267B1 (ko) |
JP (1) | JPH10506386A (ko) |
KR (1) | KR970706237A (ko) |
AU (1) | AU3373495A (ko) |
DE (1) | DE69515046T2 (ko) |
ES (1) | ES2143649T3 (ko) |
WO (1) | WO1996008462A1 (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1824810B1 (en) * | 2004-12-16 | 2013-03-27 | Huntsman Petrochemical LLC | Co-production of cyclohexylamine and bis-(para-aminocyclohexyl)-methane |
CN102030657A (zh) * | 2010-11-25 | 2011-04-27 | 浙江台州清泉医药化工有限公司 | 一种3,3′-二甲基-4,4′-二氨基二环己基甲烷的合成方法 |
TWI534131B (zh) | 2014-11-27 | 2016-05-21 | 財團法人工業技術研究院 | 氫化4,4’-二胺基二苯甲烷的觸媒與方法 |
CN110078627B (zh) * | 2019-06-03 | 2022-01-07 | 万华化学集团股份有限公司 | 一种高收率合成h6mda的方法 |
CN114160127B (zh) * | 2021-12-01 | 2023-11-14 | 常州大学 | 一种防脱胺加氢催化剂及其制备方法和应用 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
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US2551028A (en) * | 1946-10-05 | 1951-05-01 | Wallace & Tiernan Inc | Lamp changing apparatus |
US2606928A (en) * | 1947-11-18 | 1952-08-12 | Du Pont | Preparation of amino alicyclic compounds |
US2606924A (en) * | 1949-06-09 | 1952-08-12 | Du Pont | Bis (4-aminocyclohexyl)-methane |
US2606925A (en) * | 1949-12-15 | 1952-08-12 | Du Pont | Ruthenium catalyzed hydrogenation process for obtaining aminocyclohexyl compounds |
US3155724A (en) * | 1961-12-29 | 1964-11-03 | Du Pont | Process for bringing stereoisomeric mixture of bis-(4-aminocyclohexane) methane close to the equilibrium concentration |
US3347917A (en) * | 1961-12-29 | 1967-10-17 | Du Pont | Process for the preparation of di (paraaminocyclohexyl) methane |
US3636108A (en) * | 1965-12-23 | 1972-01-18 | Du Pont | Catalytic hydrogenation of aromatic nitrogen containing compounds over alkali moderated ruthenium |
CH515882A (de) * | 1965-12-23 | 1971-11-30 | Du Pont | Verfahren zur Herstellung von 4,4'-Methylen-di-(cyclohexylamin) |
US3591635A (en) * | 1968-09-25 | 1971-07-06 | Upjohn Co | Catalytic hydrogenation process for preparing di(4 - aminocyclohexyl) methane |
US3644522A (en) * | 1969-04-04 | 1972-02-22 | Du Pont | Catalytic hydrogenation of nitrogen containing compounds over supported ruthenium catalysts |
US3679746A (en) * | 1969-10-27 | 1972-07-25 | Du Pont | Isomer enrichment of bicyclohexyl-4,4{40 -diamine |
US3711550A (en) * | 1970-02-16 | 1973-01-16 | Du Pont | Isomerization of 4,4'-methylenedi (cyclohexylamine) over moderated ruthenium catalyst |
US3697449A (en) * | 1970-12-14 | 1972-10-10 | Du Pont | Alkali moderation of supported ruthenium catalysts |
US3766272A (en) * | 1972-08-25 | 1973-10-16 | Du Pont | 4,4'-methylenedi(cyclohexylamine)isomerization over a supported catalyst |
US3856862A (en) * | 1973-06-25 | 1974-12-24 | Upjohn Co | Process for hydrogenation of di(4-aminophenyl)methane with a rhodium catalyst |
US3959374A (en) * | 1974-05-30 | 1976-05-25 | Jefferson Chemical Company, Inc. | Process for the preparation of mixed isomeric methylene-bridged polycyclohexylpolyamines |
JPS5379840A (en) * | 1976-12-23 | 1978-07-14 | Takeda Chem Ind Ltd | Preparation of bis(aminomethyl)cyclohexane |
JPS5416452A (en) * | 1977-07-08 | 1979-02-07 | Takeda Chem Ind Ltd | Preparation of dis(amnomethyl) cyclohexane |
US4181680A (en) * | 1979-02-01 | 1980-01-01 | Suntech, Inc. | Hydrogenation of aromatic amines |
US4394523A (en) * | 1981-06-01 | 1983-07-19 | Mobay Chemical Corporation | Catalytic hydrogenation of di (4-aminophenyl) methane |
US4394522A (en) * | 1981-06-01 | 1983-07-19 | Mobay Chemical Corporation | Catalytic hydrogenation of di(4-aminophenyl)methane |
US4448995A (en) * | 1982-12-13 | 1984-05-15 | Mobay Chemical Corporation | Catalytic hydrogenation of di(4-aminophenyl)methane |
US4754070A (en) * | 1986-01-23 | 1988-06-28 | Air Products And Chemicals, Inc. | Hydrogenation of methylenedianiline to produce bis(para-aminocyclohexyl)methane |
US4960941A (en) * | 1988-03-30 | 1990-10-02 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts |
WO1993016030A1 (en) * | 1992-02-05 | 1993-08-19 | Olin Corporation | Promoters for hydrogenation of aromatic amines |
-
1994
- 1994-09-16 US US08/307,215 patent/US5550294A/en not_active Expired - Lifetime
-
1995
- 1995-08-28 KR KR1019970701701A patent/KR970706237A/ko not_active Application Discontinuation
- 1995-08-28 ES ES95930286T patent/ES2143649T3/es not_active Expired - Lifetime
- 1995-08-28 DE DE69515046T patent/DE69515046T2/de not_active Expired - Fee Related
- 1995-08-28 EP EP95930286A patent/EP0781267B1/en not_active Revoked
- 1995-08-28 WO PCT/US1995/010851 patent/WO1996008462A1/en not_active Application Discontinuation
- 1995-08-28 JP JP8510203A patent/JPH10506386A/ja active Pending
- 1995-08-28 AU AU33734/95A patent/AU3373495A/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP0781267B1 (en) | 2000-02-09 |
US5550294A (en) | 1996-08-27 |
AU3373495A (en) | 1996-03-29 |
EP0781267A4 (en) | 1997-11-05 |
DE69515046T2 (de) | 2000-06-29 |
ES2143649T3 (es) | 2000-05-16 |
JPH10506386A (ja) | 1998-06-23 |
DE69515046D1 (de) | 2000-03-16 |
WO1996008462A1 (en) | 1996-03-21 |
EP0781267A1 (en) | 1997-07-02 |
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