GB770299A - Improvements in and relating to the production of amines - Google Patents

Improvements in and relating to the production of amines

Info

Publication number
GB770299A
GB770299A GB6469/54A GB646954A GB770299A GB 770299 A GB770299 A GB 770299A GB 6469/54 A GB6469/54 A GB 6469/54A GB 646954 A GB646954 A GB 646954A GB 770299 A GB770299 A GB 770299A
Authority
GB
United Kingdom
Prior art keywords
diphenylamine
sec
aniline
platinum
produced
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
GB6469/54A
Inventor
Walter Theodore Dent
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB6469/54A priority Critical patent/GB770299A/en
Publication of GB770299A publication Critical patent/GB770299A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
    • C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
    • C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A process for the production of amines of the general formula <FORM:0770299/IV(b)/1> where R is a cycloaliphatic radical, or a radical having a structure <FORM:0770299/IV(b)/2> wherein R1 and R11 are alkyl, aryl or aralkyl groups, comprises the steps of coupling diphenylamine with a benzene diazonium salt whereby p-phenylaminoazobenzene which has the structure <FORM:0770299/IV(b)/3> is produced, and subsequently catalytically hydrogenating this compound in the presence of a cycloaliphatic ketone or a ketone R1COR11 whereby there is produced a mixture of amines having the structures <FORM:0770299/IV(b)/4> <FORM:0770299/IV(b)/5> The diphenylamin employed may contain alkyl or alkoxy groups in one or both of the benzene rings ortho or meta to the NH group and the benzene diazonium salt may be substituted. Hydrogenation catalysts specified comprise copper or a metal selected from Group VIII of the Periodic System, e.g. copper chromite, finely-divided nickel or platinum or platinum oxide. Chlorine-containing organic compounds may be removed from the intermediate amino azo compound by solvent extraction or by contacting a solution with an anion exchange resin. In examples: 4-isopropylamino diphenylamine and N-isopropyl aniline are obtained by diazotizing aniline dissolved in methanol and hydrochloric acid and coupling the product with diphenylamine dissolved in methanol and hydrochloric acid, separating p-phenylene aminoazobenzene hydrochloride, mixing the product with ammonia, dissolving the free base in acetone and after treating the solution with an anion exchange resin, passing the p-phenyl-aminoazo benzene dissolved in acetone with hydrogen over a copper chromite catalyst at elevated temperature and pressure and fractionating the products (1); in a similar process treatment with ether instead of anion-exchange resin is employed (2); 4-sec.-butylaminodiphenylamine and N-sec.-butylaniline are obtained in a similar process using aniline, diphenylamine and methyl ethyl ketone and a platinum-on-charcoal hydrogenation catalyst (3); 4-cyclohexylaminodiphenylamine is obtained by hydrogenating p-phenylaminoazobenzene, produced as in (1), in cyclohexanone solution using a platinum-on-charcoal catalyst (4); 4 - isopropylaminodiphenylamine is produced by a process similar to (1) in which an excess of the diazonium salt is employed and recycled (5); 3 : 31-dimethyl-4 - sec. - butylaminodiphenylamine is obtained in a process similar to (3) using 3 : 31-dimethyldiphenylamine as starting material (6); and in similar processes diphenylamine and p-toluidine (7), m-toluidine (8) and p-anisidine (9) are employed instead of aniline to obtain 4-sec.-butylamino-diphenylamine. The products of the invention may be used in stabilizing compounds liable to peroxide formation, e.g. petrols, aldehydes, ethers, esters of unsaturated carboxylic acids and unsaturated hydrocarbons or mixtures thereof.ALSO:Petrols are stabilized with amines having the structure <FORM:0770299/III/1> wherein R is a cycloaliphatic radical or a radical -CH(R1)(R11) where R1 and R11 are alkyl, aryl or aralkyl groups (see Group IV(b))
GB6469/54A 1954-03-05 1954-03-05 Improvements in and relating to the production of amines Expired GB770299A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB6469/54A GB770299A (en) 1954-03-05 1954-03-05 Improvements in and relating to the production of amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB6469/54A GB770299A (en) 1954-03-05 1954-03-05 Improvements in and relating to the production of amines

Publications (1)

Publication Number Publication Date
GB770299A true GB770299A (en) 1957-03-20

Family

ID=9815038

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6469/54A Expired GB770299A (en) 1954-03-05 1954-03-05 Improvements in and relating to the production of amines

Country Status (1)

Country Link
GB (1) GB770299A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993024450A1 (en) * 1992-05-22 1993-12-09 Monsanto Company Process for preparing substituted aromatic amines
WO1994025425A1 (en) * 1993-04-26 1994-11-10 Monsanto Company Process for preparing substituted aromatic amines
CN102875412A (en) * 2012-10-22 2013-01-16 浙江万丰化工有限公司 Method for oxidatively preparing azoic compound by amino compounds

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993024450A1 (en) * 1992-05-22 1993-12-09 Monsanto Company Process for preparing substituted aromatic amines
WO1994025425A1 (en) * 1993-04-26 1994-11-10 Monsanto Company Process for preparing substituted aromatic amines
US5451702A (en) * 1993-04-26 1995-09-19 Monsanto Company Process for preparing substituted aromatic amines
CN1046701C (en) * 1993-04-26 1999-11-24 孟山都公司 Process for preparing substituted aromatic amines
CN102875412A (en) * 2012-10-22 2013-01-16 浙江万丰化工有限公司 Method for oxidatively preparing azoic compound by amino compounds

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