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
Application number
GB56794/66A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1122609A publication Critical patent/GB1122609A/en
Expired legal-status Critical Current

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.
GB56794/66A 1965-12-23 1966-12-19 Production of a mixture of stereoisomers of 4,4'-methylenedi(cyclohexylamine) Expired GB1122609A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US51610765A 1965-12-23 1965-12-23
US51614065A 1965-12-23 1965-12-23
US51609365A 1965-12-23 1965-12-23
US51609265A 1965-12-23 1965-12-23
US58797966A 1966-10-20 1966-10-20
US58798066A 1966-10-20 1966-10-20
US58798266A 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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (12)

* Cited by examiner, † Cited by third party
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
NL154495B (en) 1977-09-15
CH515882A (en) 1971-11-30
NL6618017A (en) 1967-06-26
JPS4938262B1 (en) 1974-10-16
DE1593293B2 (en) 1980-02-28
DE1593293A1 (en) 1970-07-16
LU52622A1 (en) 1967-02-20
DE1593293C3 (en) 1980-10-23

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