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GB771063A - Improvements in and relating to the production of amines - Google Patents

Improvements in and relating to the production of amines

Info

Publication number
GB771063A
GB771063A GB6470/54A GB647054A GB771063A GB 771063 A GB771063 A GB 771063A GB 6470/54 A GB6470/54 A GB 6470/54A GB 647054 A GB647054 A GB 647054A GB 771063 A GB771063 A GB 771063A
Authority
GB
United Kingdom
Prior art keywords
sec
butyl
aniline
groups
hydrogenation
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
GB6470/54A
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 GB6470/54A priority Critical patent/GB771063A/en
Publication of GB771063A publication Critical patent/GB771063A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • 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
    • 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
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/84—Purification
    • 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
    • C07C211/45—Monoamines
    • C07C211/46—Aniline
    • 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
    • C07C211/51—Phenylenediamines
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

In a process for the production of amines having the structure <FORM:0771063/IV(b)/1> where R1 and R11 are cycloaliphatic groups or groups having a structure <FORM:0771063/IV(b)/2> where R1 and R11 are alkyl or aralkyl groups, an amine of the structure <FORM:0771063/IV(b)/3> is coupled with a benzene diazonium salt to give an azo compound having a structure <FORM:0771063/IV(b)/4> which is catalytically hydrogenated in the presence of a cycloaliphatic ketone or a ketone having the structure R1.CO.R11, whereby amines having the structures <FORM:0771063/IV(b)/5> and <FORM:0771063/IV(b)/6> are formed simultaneously. In modifications of the process a substituted benzene diazonium salt, e.g. such as that produced from o-toluidine, and an N-substituted aniline containing alkyl or alkoxy groups situated in ortho or meta positions to the substituted amino group, e.g. N - methyl - o - toluidine, N - methyl - o - or m - anisidine, may be employed. In a further modification of the process the intermediate amino-azo compound may be converted to the corresponding nitrosamino compound of the formula <FORM:0771063/IV(b)/7> by treatment with sodium nitrite and hydrochloric acid prior to catalytic hydrogenation in the presence of a ketone of the kind defined. The intermediate amino-azo compound or the nitroso derivative thereof may be freed from traces of chlorine containing organic compounds before hydrogenation by solvent extraction or by treatment in solution with an anion exchange resin. 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. The hydrogenation is preferably carried out in the liquid phase. Aniline may be added to the reactants before the catalytic hydrogenation. The products may be used as antioxidants in stabilizing compounds liable to deterioration due to peroxide formation, e.g. petrols, aldehydes, ethers, esters of unsaturated carboxylic acids and unsaturated hydrocarbons or mixtures containing such compounds. In examples: N,N1-di-sec.-butyl-p-phenylenediamine is obtained by coupling N-sec. butyl-aniline with diazotized aniline in methanol solution, treating the reacted mixture with water and ammonia and extracting with petroleum ether the 4-sec. butyl-aminoazobenzene and hydrogenating the latter with methyl ethyl ketone in the presence of a platinum-on-charcoal catalyst (1); N,N1-di-isopropropyl - p - phenylene - diamine is obtained in a similar process employing N-isopropyl-aniline instead of N-sec. butyl-aniline and acetone instead of methyl ethyl ketone (3); N,N1-di-sec. butyl-p-phenylenediamine is obtained by a process similar to (1) except that the azo compound intermediate is converted to 4-N-(nitroso-sec. butyl)-amino azo benzene by treatment with hydrochloric acid and sodium nitrite before hydrogenation (2).ALSO:Petrols are stabilized with amines having the structure <FORM:0771063/III/1> wherein R1 and R11 are cyclo-aliphatic group or groups having a structure <FORM:0771063/III/2> wherein R1 and R11 are alkyl or aralkyl groups (see Group IV(b))
GB6470/54A 1954-03-05 1954-03-05 Improvements in and relating to the production of amines Expired GB771063A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB6470/54A GB771063A (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
GB6470/54A GB771063A (en) 1954-03-05 1954-03-05 Improvements in and relating to the production of amines

Publications (1)

Publication Number Publication Date
GB771063A true GB771063A (en) 1957-03-27

Family

ID=9815058

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6470/54A Expired GB771063A (en) 1954-03-05 1954-03-05 Improvements in and relating to the production of amines

Country Status (1)

Country Link
GB (1) GB771063A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116003292A (en) * 2022-12-12 2023-04-25 沈阳化工研究院有限公司 A kind of method of synthesizing amino azobenzene

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116003292A (en) * 2022-12-12 2023-04-25 沈阳化工研究院有限公司 A kind of method of synthesizing amino azobenzene
CN116003292B (en) * 2022-12-12 2024-11-01 沈阳化工研究院有限公司 Method for synthesizing amino azobenzene

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