GB1176337A - Producing Amines by Catalytic Hydrogenation over supported Ruthenium Catalyst - Google Patents

Producing Amines by Catalytic Hydrogenation over supported Ruthenium Catalyst

Info

Publication number
GB1176337A
GB1176337A GB57281/66A GB5728166A GB1176337A GB 1176337 A GB1176337 A GB 1176337A GB 57281/66 A GB57281/66 A GB 57281/66A GB 5728166 A GB5728166 A GB 5728166A GB 1176337 A GB1176337 A GB 1176337A
Authority
GB
United Kingdom
Prior art keywords
ruthenium
compound
calculated
catalyst
hydrogenated
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
GB57281/66A
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 GB1176337A publication Critical patent/GB1176337A/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
    • B01J23/63—Platinum group metals with rare earths or actinides
    • 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
    • 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

Abstract

1,176,337. Amines. E. I. DU PONT DE NEMOURS & CO. 21 Dec., 1966 [23 Dec., 1965 (2); 20 Oct., 1966 (2)], No. 57281/66. Heading C2C. A process for the hydrogenation of adiponitrile or a compound having the formula where R is a phenyl, pyridyl, naphthyl, indolyl, phenanthryl, anthracenyl, fluorenyl or quinolinyl group ; A and B are the same or different and are amine groups -NR 1 R 2 in which R 1 and R 2 are the same or different and are hydrogen atoms, C 1-12 alkyl groups or phenyl groups, R 3 is a hydrogen atom, a C 1-12 alkyl group or a C 1-5 alkoxyl group, R 4 is a C 1-4 alkylene group or a cyclohexylidene, cyclopentylidene or oxy group, x is 1, 2, 3 or 4 and y is 1 or 2 comprises contacting the compound with hydrogen at a pressure of 500 to 15,000 pounds per square inch and a temperature of 120‹ to 300‹ C. in the presence of 0 to 200% of ammonia based on the weight of the compound to be hydrogenated and 0À001 to 10% (on the same basis and calculated as metallic ruthenium) of a ruthenium catalyst comprising ruthenium supported on alumina barium sulphate, or kieselguhr, said catalyst being alkali moderated with 0À1 to 15% of a basic alkali metal compound calculated as the alkali metal. In a modification compounds of the given formulµ are contacted with hydrogen at a pressure of 500 to 15,000p.s.i. and temperature of 120‹ to 300‹ C. in the presence of 0 to 200% of ammonia (based on the weight of the compound to be hydrogenated) and 0À001 to 10% (on the same basis and calculated as metallic ruthenium) of a ruthenium catalyst comprising ruthenium supported on calcium carbonate, a rare earth oxide or a mixture of two or more of these. In a further modification adiponitrile or a compound of one of the above formula where R is phenyl, R 1 , R 2 and R 3 are the same or different and hydrogen atoms or C 1-5 alkyl groups, R 4 is a C 1-4 alkylene group or a cyclohexylidene group, x is 1-4 and y is 1 or 2 is hydrogenated using a hydrogen pressure of 200-15,000 p.s.i. and a temperature of 120-300‹ C. in the presence of 1-100% ammonia (based on the weight of the compound to be hydrogenated) and of 0À001 to 10% (on the same basis and calculated as metallic ruthenium) of a ruthenium catalyst comprising ruthenium supported on alumina barium sulphate or kieselguhr said catalyst being alkali moderated with 0À1 to 15% of a basic alkali metal compound calculated as the alkali metal. In a further modification a hydrogen pressure of 200-15,000 p.s.i., a temperature of 120‹ to 300‹ C., 0 to 100% of ammonia (based on the weight of the compound to be hydrogenated and 0-001 to 10% (on the same basis and calculated as metallic ruthenium) of a ruthenium catalyst comprising ruthenium supported on calcium carbonate, a rare earth oxide, or a mixture of two or more of these are employed. Numerous examples are furnished. Specifications 1,122,609 and 1,150,380 are referred to.
GB57281/66A 1965-12-23 1966-12-21 Producing Amines by Catalytic Hydrogenation over supported Ruthenium Catalyst Expired GB1176337A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US51608365A 1965-12-23 1965-12-23
US51610865A 1965-12-23 1965-12-23
US58801166A 1966-10-20 1966-10-20
US58798166A 1966-10-20 1966-10-20

Publications (1)

Publication Number Publication Date
GB1176337A true GB1176337A (en) 1970-01-01

Family

ID=27504528

Family Applications (1)

Application Number Title Priority Date Filing Date
GB57281/66A Expired GB1176337A (en) 1965-12-23 1966-12-21 Producing Amines by Catalytic Hydrogenation over supported Ruthenium Catalyst

Country Status (7)

Country Link
BE (1) BE691615A (en)
CH (1) CH485646A (en)
DE (1) DE1593289C3 (en)
FR (1) FR1510239A (en)
GB (1) GB1176337A (en)
LU (1) LU52649A1 (en)
NL (1) NL154713B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5031140B1 (en) * 1970-06-29 1975-10-07
WO2007077903A2 (en) * 2005-12-28 2007-07-12 Kao Corporation Process for producing nitrogen-containing compounds
CN101346343B (en) * 2005-12-28 2012-05-30 花王株式会社 Process for producing nitrogen-containing compounds
CN114315635A (en) * 2021-12-27 2022-04-12 江苏康恒化工有限公司 2, 2' -dichloroazobenzene synthesis process

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2502893C2 (en) * 1975-01-24 1982-10-14 Bayer Ag, 5090 Leverkusen Cycloaliphatic amines
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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2606925A (en) * 1949-12-15 1952-08-12 Du Pont Ruthenium catalyzed hydrogenation process for obtaining aminocyclohexyl compounds
DE1282018B (en) * 1961-12-29 1968-11-07 Du Pont Process for the preparation of an isomer mixture of bis (4-aminocyclohxyl) methane with equilibrium distribution of the isomers

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5031140B1 (en) * 1970-06-29 1975-10-07
WO2007077903A2 (en) * 2005-12-28 2007-07-12 Kao Corporation Process for producing nitrogen-containing compounds
WO2007077903A3 (en) * 2005-12-28 2007-09-13 Kao Corp Process for producing nitrogen-containing compounds
CN101346343B (en) * 2005-12-28 2012-05-30 花王株式会社 Process for producing nitrogen-containing compounds
US8247611B2 (en) 2005-12-28 2012-08-21 Kao Corporation Process for producing nitrogen-containing compounds
CN114315635A (en) * 2021-12-27 2022-04-12 江苏康恒化工有限公司 2, 2' -dichloroazobenzene synthesis process

Also Published As

Publication number Publication date
LU52649A1 (en) 1967-02-20
DE1593289C3 (en) 1982-04-29
CH485646A (en) 1970-02-15
DE1593289A1 (en) 1970-07-30
DE1593289B2 (en) 1981-04-09
FR1510239A (en) 1968-01-19
BE691615A (en) 1967-06-22
NL154713B (en) 1977-10-17
NL6618015A (en) 1967-06-26

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