CA2050167A1 - Process for the production of di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the trans-trans isomer - Google Patents

Process for the production of di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the trans-trans isomer

Info

Publication number
CA2050167A1
CA2050167A1 CA002050167A CA2050167A CA2050167A1 CA 2050167 A1 CA2050167 A1 CA 2050167A1 CA 002050167 A CA002050167 A CA 002050167A CA 2050167 A CA2050167 A CA 2050167A CA 2050167 A1 CA2050167 A1 CA 2050167A1
Authority
CA
Canada
Prior art keywords
trans
weight
aminocyclohexyl
production
methane containing
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.)
Granted
Application number
CA002050167A
Other languages
French (fr)
Other versions
CA2050167C (en
Inventor
Otto Immel
Gerhard Darsow
Rudolf Braden
Hans-Helmut Schwarz
Helmut Waldmann
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.)
Bayer AG
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2050167A1 publication Critical patent/CA2050167A1/en
Application granted granted Critical
Publication of CA2050167C publication Critical patent/CA2050167C/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • B01J23/40—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
    • 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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the traps-traps isomer can be obtained by the catalytic hydrogenation of di-(4-aminophenyl)-methane at elevated temperature and elevated hydrogen pressure in the presence of a ruthenium-containing supported catalyst containing 0.05 to 5% by weight ruthenium on an Al2 0 3 support which has been treated with compounds of rare earth metals and manganese.
CA002050167A 1990-09-06 1991-08-30 Process for the production of di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the trans-trans isomer Expired - Fee Related CA2050167C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4028270.8 1990-09-06
DE4028270A DE4028270A1 (en) 1990-09-06 1990-09-06 PROCESS FOR THE PREPARATION OF DI- (4-AMINOCYCLOHEXYL) -METHANE WITH A SHARE OF 15 TO 25% BY WEIGHT OF THE TRANS-TRANS ISOMER

Publications (2)

Publication Number Publication Date
CA2050167A1 true CA2050167A1 (en) 1992-03-07
CA2050167C CA2050167C (en) 2001-04-17

Family

ID=6413715

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002050167A Expired - Fee Related CA2050167C (en) 1990-09-06 1991-08-30 Process for the production of di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the trans-trans isomer

Country Status (4)

Country Link
EP (1) EP0476359B1 (en)
JP (1) JP3046862B2 (en)
CA (1) CA2050167C (en)
DE (2) DE4028270A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4328007A1 (en) * 1993-08-20 1995-02-23 Huels Chemische Werke Ag Catalyst for the production of bis-para-aminocyclohexylmethane with a low proportion of trans-trans isomer by hydrogenation of methylenediamine
DE4404220A1 (en) * 1994-02-10 1995-08-17 Bayer Ag Ruthenium catalysts, their production and a process for the preparation of cycloaliphatic polyamines using these catalysts
DE10231119A1 (en) * 2002-07-10 2004-02-05 Degussa Ag Process for increasing the selectivity of the hydrogenation of 4,4'-diaminodiphenylmethane to 4,4'-diaminodicyclohexylmethane in the presence of an N-alkyl-4,4'-diaminodiphenylmethane
US10294194B2 (en) 2015-03-09 2019-05-21 Mitsubishi Gas Chemical Company, Inc. Isomerization method for diaminodicyclohexylmethane

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3404098A (en) * 1965-12-23 1968-10-01 Du Pont Platinum group metal catalysts supported on rare earth carbonates
CH515882A (en) * 1965-12-23 1971-11-30 Du Pont 4,4'-Methylene di-(cyclohexylamine) prepn - with control of stereoisomer concn
US3644522A (en) * 1969-04-04 1972-02-22 Du Pont Catalytic hydrogenation of nitrogen containing compounds over supported ruthenium catalysts
DE3045719A1 (en) * 1980-12-04 1982-07-08 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING CYCLOALIPHATIC AND / OR AROMATIC AMINES
EP0324190B1 (en) * 1988-01-14 1993-05-12 Hüls Aktiengesellschaft Process for the production of 4,4'-diamino-dicyclohexylmethane with a low trans-trans isomer content by the catalytic hydrogenation of 4,4'-diaminodiphenylmethane
DE3824822A1 (en) * 1988-07-21 1990-01-25 Bayer Ag RUTHENIUM CARRIER CATALYST, ITS PRODUCTION AND ITS USE IN THE PRODUCTION OF CYCLOHEXYLAMINE SUBSTITUTEDLY, AND SUBSTITUTED DICYCLOHEXYLAMINE SUBSTITUTED, IF ANY

Also Published As

Publication number Publication date
EP0476359B1 (en) 1993-09-29
JP3046862B2 (en) 2000-05-29
DE4028270A1 (en) 1992-03-12
CA2050167C (en) 2001-04-17
JPH04247056A (en) 1992-09-03
DE59100432D1 (en) 1993-11-04
EP0476359A1 (en) 1992-03-25

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