GB719610A - Manufacture of new azapentylene diammonium compounds - Google Patents

Manufacture of new azapentylene diammonium compounds

Info

Publication number
GB719610A
GB719610A GB32483/52A GB3248352A GB719610A GB 719610 A GB719610 A GB 719610A GB 32483/52 A GB32483/52 A GB 32483/52A GB 3248352 A GB3248352 A GB 3248352A GB 719610 A GB719610 A GB 719610A
Authority
GB
United Kingdom
Prior art keywords
acid
azapentylene
reacted
give
compounds
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
GB32483/52A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB719610A publication Critical patent/GB719610A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62Quaternary ammonium compounds
    • C07C211/63Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention comprises new secondary 3-azapentylene - (1,5) - di - trialkyl ammonium compounds of formula: <FORM:0719610/IV (b)/1> in which R1-R6 represent alkyl residues with 1-3 carbon atoms and A- stands for an anion, and secondary amine salts thereof. A- may be a halogen ion, an ion of a therapeutically applicable acid, for example methyl sulphuric acid, or of an alkyl or aryl sulphonic acid or of an organic carboxylic acid, for example acetic acid, propionic acid, succinic acid, tartaric acid, citric acid or benzoic acid, or the hydroxyl ion. Particularly valuable compounds of the above formula in which R1 to R4 are methyl residues are N,N,N1,N1 - tetramethyl - N,N1 - diethyl-3 - azapentylene - (1,5) - diammonium compounds, e.g. the dibromide, and the N,N,N, N1,N1,N1 - hexamethyl - 3 - azapentylene-(1,5) - diammonium compounds, e.g. the diiodide. The new compounds are obtained when an azalkane diamine of formula <FORM:0719610/IV (b)/2> is treated with quaternating agents which are capable of introducing an alkyl residue with 1-3 carbon atoms. Suitable quaternating agents are alkyl halides, such as methyl or ethyl chloride, bromide or iodide; dialkyl sulphates such as dimethyl or diethyl sulphate; or alkyl or aryl sulphonic acid esters such as p-toluene sulphonic acid methyl ester. The reaction may be carried out in the presence of solvents such as alcohol or acetone. The quaternary ammonium salts may be converted into their quaternary ammonium hydroxides, for example by reaction of the halides with silver oxide or of the sulphates with barium hydroxide or by treatment of the quaternary salts with anion exchangers. From the bases thus obtained the quaternary salts of such acids as acetic, propionic, succinic, tartanic, citric and benzoic acids may be obtained by reaction with the acids. Secondary amine salts may be obtained by reacting these salts with acids such as hydrohalic acids. In the examples: (a) o ,o 1-tetramethyl diethylene triamine (obtained by hydrogenation of dimethyl-amino-acetonitrile) is dissolved in alcohol and reacted with methyl iodide to give N,N,N, N1,N1,N1 - hexamethyl - 3 - azapentylene - (1,5) diammonium diiodide of formula: <FORM:0719610/IV (b)/3> by treating with hydrogen iodide the hydriodide of formula: <FORM:0719610/IV (b)/4> is obtained; (b) o ,o 1-tetramethyl-dimethylene triamine is reacted with ethyl iodide to give <FORM:0719610/IV (b)/5> and (c) o ,o 1-tetramethyl diethylene triamine is reacted with ethyl bromide to give <FORM:0719610/IV (b)/6> which is reacted with silver oxide to give the dihydroxide; the dihydroxide is reacted with hydrochloric acid to give N,N,N1,N1-tetramethyl - N,N1 - diethyl - 3 - azapentylene-(1,5)-diammonium dichloride.
GB32483/52A 1952-01-29 1952-12-22 Manufacture of new azapentylene diammonium compounds Expired GB719610A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH719610X 1952-01-29

Publications (1)

Publication Number Publication Date
GB719610A true GB719610A (en) 1954-12-01

Family

ID=4531432

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32483/52A Expired GB719610A (en) 1952-01-29 1952-12-22 Manufacture of new azapentylene diammonium compounds

Country Status (1)

Country Link
GB (1) GB719610A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2321900A (en) * 1997-02-11 1998-08-12 Procter & Gamble Cationic surfactants

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2321900A (en) * 1997-02-11 1998-08-12 Procter & Gamble Cationic surfactants

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