GB719610A - Manufacture of new azapentylene diammonium compounds - Google Patents
Manufacture of new azapentylene diammonium compoundsInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary 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.
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2321900A (en) * | 1997-02-11 | 1998-08-12 | Procter & Gamble | Cationic surfactants |
-
1952
- 1952-12-22 GB GB32483/52A patent/GB719610A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2321900A (en) * | 1997-02-11 | 1998-08-12 | Procter & Gamble | Cationic surfactants |
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