GB512629A - Manufacture of dithiohydantoins - Google Patents

Manufacture of dithiohydantoins

Info

Publication number
GB512629A
GB512629A GB729838A GB729838A GB512629A GB 512629 A GB512629 A GB 512629A GB 729838 A GB729838 A GB 729838A GB 729838 A GB729838 A GB 729838A GB 512629 A GB512629 A GB 512629A
Authority
GB
United Kingdom
Prior art keywords
compound
prepared
dithiohydantoins
carbon disulphide
cyanide
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
GB729838A
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.)
HERBERT CLARE CARRINGTON
Imperial Chemical Industries Ltd
Original Assignee
HERBERT CLARE CARRINGTON
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 HERBERT CLARE CARRINGTON, Imperial Chemical Industries Ltd filed Critical HERBERT CLARE CARRINGTON
Priority to GB729838A priority Critical patent/GB512629A/en
Publication of GB512629A publication Critical patent/GB512629A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

512,629. Dithiohydantoins. CARRINGTON, H. C., and IMPERIAL CHEMICAL INDUSTRIES, Ltd. March. 8, 1938, No. 7298. [Class 2 (iii)] Dithiohydantoins of the formula in which R represents a closed methylene chain, are prepared by reacting an amino-nitrile of the formula NH2-C(CN)=R with carbon disulphide. The amino-nitrile may be generated in situ from a ketone R=CO and ammonium cyanide or a mixture of alkali metal cyanide or a mixture of alkali metal cyanide and an ammonium salt. The products, in the form of their salts with amines, e.g., piperidine, cyclohexylamine, N-ethylcyclohexylamine or , diphenylguanidine, are useful as vulcanisation accelerators. According to the examples, (1) pentamethylene-5:5-spiro-2:4-dithiohydantoin is prepared by heating a methanol solution of cyclohexanone with an aqueous solution of ammonium chloride and sodium cyanide to which carbon disulphide has been added ; in a similar way, the tetramethylene-compound is prepared from cyclopentanone, the 3'-methylpentamethylene-compound from p methylcyclohexanone, the 1<1>-methylpentamethylenecompound from o-methyleyclohexanone, the 2<1>-methylpentamenthylene-compound from mmethylcyclohexanone, the 2<1>-methyltetramethylene-compound from 3-methylcyclopentanone. and the 2<1>methyl-5<1>-isopropylpentamethylenecompound from l-menthone; (2) pentamethylene-5:5<1>-spiro-2:4-dithiohydantoin is obtained when an ethanol solution of x-cyanocyclohenylamino and carbon disulphide is allowed to stand for several days.
GB729838A 1938-03-08 1938-03-08 Manufacture of dithiohydantoins Expired GB512629A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB729838A GB512629A (en) 1938-03-08 1938-03-08 Manufacture of dithiohydantoins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB729838A GB512629A (en) 1938-03-08 1938-03-08 Manufacture of dithiohydantoins

Publications (1)

Publication Number Publication Date
GB512629A true GB512629A (en) 1939-09-21

Family

ID=9830424

Family Applications (1)

Application Number Title Priority Date Filing Date
GB729838A Expired GB512629A (en) 1938-03-08 1938-03-08 Manufacture of dithiohydantoins

Country Status (1)

Country Link
GB (1) GB512629A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2732380A (en) * 1956-01-24 Process for the production of
US4189587A (en) * 1977-04-05 1980-02-19 Ciba-Geigy Corporation 1,3-Diaminomethyl-hydantoin additives for lubricating oils

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2732380A (en) * 1956-01-24 Process for the production of
US4189587A (en) * 1977-04-05 1980-02-19 Ciba-Geigy Corporation 1,3-Diaminomethyl-hydantoin additives for lubricating oils

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