GB1122609A - Production of a mixture of stereoisomers of 4,4'-methylenedi(cyclohexylamine) - Google Patents
Production of a mixture of stereoisomers of 4,4'-methylenedi(cyclohexylamine)Info
- Publication number
- GB1122609A GB1122609A GB56794/66A GB5679466A GB1122609A GB 1122609 A GB1122609 A GB 1122609A GB 56794/66 A GB56794/66 A GB 56794/66A GB 5679466 A GB5679466 A GB 5679466A GB 1122609 A GB1122609 A GB 1122609A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixture
- methylenedi
- cyclohexylamine
- ruthenium
- stereoisomers
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/58—Platinum group metals with alkali- or alkaline earth metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/63—Platinum group metals with rare earths or actinides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
The invention relates to a process for the preparation of a mixture of approximately equilibrium concentration of the stereo-isomers of 4,41-methylenedi (cyclohexylamine) which comprises contacting either (a) p,p1-methylenedianiline or (b) a mixture of other than equilibrium concentration of the stereoisomers of 4,41-methylenedi (cyclohexylamine), with hydrogen at a pressure of from 500 to 15,000 pounds per square inch and a temperature from about 150 DEG to 300 DEG C., in the presence of from 0 to 500 per cent ammonia and from 0 to 100 parts of an inert liquid organic solvent (both reckoned on the weight of (a) or (b) starting material) in the presence also of from 0.001 to 10% of ruthenium catalyst (reckoned on the same basis and calculated as ruthenium) comprising either (1) ruthenium supported on calcium carbonate, a rare earth oxide or a mixture of two or more of these or (2) ruthenium supported on alumina, barium sulphate or kieselguhr, and alkali-moderated with from 0.1 to 15% of a basic alkali metal compound.
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US51614065A | 1965-12-23 | 1965-12-23 | |
US51609365A | 1965-12-23 | 1965-12-23 | |
US51609265A | 1965-12-23 | 1965-12-23 | |
US51610765A | 1965-12-23 | 1965-12-23 | |
US58798066A | 1966-10-20 | 1966-10-20 | |
US58798266A | 1966-10-20 | 1966-10-20 | |
US58797966A | 1966-10-20 | 1966-10-20 | |
US58798966A | 1966-10-20 | 1966-10-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1122609A true GB1122609A (en) | 1968-08-07 |
Family
ID=27575458
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB56794/66A Expired GB1122609A (en) | 1965-12-23 | 1966-12-19 | Production of a mixture of stereoisomers of 4,4'-methylenedi(cyclohexylamine) |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS4938262B1 (en) |
CH (1) | CH515882A (en) |
DE (1) | DE1593293C3 (en) |
GB (1) | GB1122609A (en) |
LU (1) | LU52622A1 (en) |
NL (1) | NL154495B (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0066210A1 (en) * | 1981-06-01 | 1982-12-08 | Mobay Chemical Corporation | Catalytic hydrogenation of di-(4-aminophenyl) methane |
EP0066212A1 (en) * | 1981-06-01 | 1982-12-08 | Mobay Chemical Corporation | Process for the catalytic hydrogenation of di-(4-aminophenyl) methane |
US4960941A (en) * | 1988-03-30 | 1990-10-02 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts |
US5196594A (en) * | 1988-01-14 | 1993-03-23 | Miles, Inc. | Process for the production of 4,4'-diamino-dicyclohexylmethane with a low trans-trans isomer content by the catalytic hydrogenation of 4,4'-diamino-diphenylmethane |
US5214212A (en) * | 1992-02-27 | 1993-05-25 | Olin Corporation | Promoters for hydrogenation of aromatic amines |
US5360934A (en) * | 1993-06-25 | 1994-11-01 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts |
US5550294A (en) * | 1992-02-05 | 1996-08-27 | Olin Corporation | Method of increasing hydrogenation rate of aromatic amines |
US6121493A (en) * | 1993-03-30 | 2000-09-19 | Air Products And Chemicals, Inc. | Isomerization of cyclohexylamines to produce their thermodynamic isomeric form |
US6140540A (en) * | 1993-04-06 | 2000-10-31 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts |
EP1251119A2 (en) * | 2001-04-19 | 2002-10-23 | Bayer Ag | Continuous process for preparing diamino dicyclohexylmethane |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4020104A (en) * | 1976-09-20 | 1977-04-26 | The Upjohn Company | Process for isomerizing cis,cis- and cis,trans-isomers of di-(p-aminocyclohexyl)methane to the corresponding trans,trans-isomer |
JPS5416479U (en) * | 1977-07-06 | 1979-02-02 | ||
DE4028270A1 (en) * | 1990-09-06 | 1992-03-12 | Bayer Ag | PROCESS FOR THE PREPARATION OF DI- (4-AMINOCYCLOHEXYL) -METHANE WITH A SHARE OF 15 TO 25% BY WEIGHT OF THE TRANS-TRANS ISOMER |
US7465833B2 (en) * | 2005-09-22 | 2008-12-16 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to alicyclic amines using a lithium aluminate-based catalyst |
DE102008002002A1 (en) | 2008-05-27 | 2009-12-03 | Evonik Degussa Gmbh | Low chlorine multi-step process for the preparation of cycloaliphatic diisocyanates |
CN109535007A (en) * | 2018-11-07 | 2019-03-29 | 万华化学集团股份有限公司 | A kind of diamino-dicyclohexyl methane isomer separation method |
-
1966
- 1966-12-15 CH CH1798066A patent/CH515882A/en not_active IP Right Cessation
- 1966-12-19 GB GB56794/66A patent/GB1122609A/en not_active Expired
- 1966-12-19 LU LU52622D patent/LU52622A1/xx unknown
- 1966-12-22 NL NL666618017A patent/NL154495B/en not_active IP Right Cessation
- 1966-12-22 JP JP41083796A patent/JPS4938262B1/ja active Pending
- 1966-12-23 DE DE1593293A patent/DE1593293C3/en not_active Expired
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0066210A1 (en) * | 1981-06-01 | 1982-12-08 | Mobay Chemical Corporation | Catalytic hydrogenation of di-(4-aminophenyl) methane |
EP0066212A1 (en) * | 1981-06-01 | 1982-12-08 | Mobay Chemical Corporation | Process for the catalytic hydrogenation of di-(4-aminophenyl) methane |
US4394523A (en) * | 1981-06-01 | 1983-07-19 | Mobay Chemical Corporation | Catalytic hydrogenation of di (4-aminophenyl) methane |
US5196594A (en) * | 1988-01-14 | 1993-03-23 | Miles, Inc. | Process for the production of 4,4'-diamino-dicyclohexylmethane with a low trans-trans isomer content by the catalytic hydrogenation of 4,4'-diamino-diphenylmethane |
US4960941A (en) * | 1988-03-30 | 1990-10-02 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts |
US5550294A (en) * | 1992-02-05 | 1996-08-27 | Olin Corporation | Method of increasing hydrogenation rate of aromatic amines |
US5214212A (en) * | 1992-02-27 | 1993-05-25 | Olin Corporation | Promoters for hydrogenation of aromatic amines |
US6121493A (en) * | 1993-03-30 | 2000-09-19 | Air Products And Chemicals, Inc. | Isomerization of cyclohexylamines to produce their thermodynamic isomeric form |
US6140540A (en) * | 1993-04-06 | 2000-10-31 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts |
US5360934A (en) * | 1993-06-25 | 1994-11-01 | Air Products And Chemicals, Inc. | Hydrogenation of aromatic amines to produce their ring hydrogenated counterparts |
EP1251119A2 (en) * | 2001-04-19 | 2002-10-23 | Bayer Ag | Continuous process for preparing diamino dicyclohexylmethane |
EP1251119A3 (en) * | 2001-04-19 | 2003-11-05 | Bayer Ag | Continuous process for preparing diamino dicyclohexylmethane |
Also Published As
Publication number | Publication date |
---|---|
DE1593293B2 (en) | 1980-02-28 |
JPS4938262B1 (en) | 1974-10-16 |
NL6618017A (en) | 1967-06-26 |
LU52622A1 (en) | 1967-02-20 |
CH515882A (en) | 1971-11-30 |
NL154495B (en) | 1977-09-15 |
DE1593293A1 (en) | 1970-07-16 |
DE1593293C3 (en) | 1980-10-23 |
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