GB538718A - Manufacture of acid salts of quaternary ammonium bases - Google Patents
Manufacture of acid salts of quaternary ammonium basesInfo
- Publication number
- GB538718A GB538718A GB3151?/39D GB3151239D GB538718A GB 538718 A GB538718 A GB 538718A GB 3151239 D GB3151239 D GB 3151239D GB 538718 A GB538718 A GB 538718A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- dimethylaminobenzyl
- prepared
- base
- tertiary
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
538,718. Acid salts of quaternary ammonium bases. GEIGY AKT.-GES., J. R. Dec. 5, 1939, No. 31512. Convention date, Dec. 6, 1938. Samples furnished. [Class 2 (iii)] Acid quaternary ammonium salts are prepared by reacting (a) a quaternary mono or poly ammonium base containing at least one radicle of 8 or more carbons with an aliphatic or cycloaliphatic carboxylic acid having at least 8 carbon atoms and an acid having a molecular weight below 144 in either order ; (b) a tertiary mono or polyamine containing at least one radicle of 8 or more carbons with an aliphatic or cycloaliphatic carboxylic acid having at least 8 carbons and reacting the resulting salt with an alkylating agent which introduces an anionoid radicle having a molecular weight below 144 ; or (c) a tertiary amine containing at least one hydrogen attached to oxygen or other hetero atom with an aliphatic or cycloaliphatic acid having at least 8 carbons in sufficient proportion that after acylation at least one molecular proportion of acid is available for salt formation and treating the acylated product with an alkylating agent which introduces an anionoid radicle having a molecular weight below 144. In an example, 4-dimethylamine - 4<SP>1</SP> -methylhydroxyethylaminodiphenylmethane is melted with a mixture of stearic and palmitic acids and the esterification completed by heating and raising the pressure by introducing carbon dioxide. An acid quaternary salt is produced by treating with olein and dimethylsulphate. Products are mentioned which are prepared from the following bases : (1) methylhydroxyethylaniline ; (2) α:#-dihydroxypropylmethyltoluidine (from methyltoluidine and glycerolchlorhydrin) ; (3) 4:4<SP>1</SP>- di-(p-dimethylaminobenzyl) diphenylamine, prepared from: 1 mol. diphenylamine and 2 mols. p-dimethylaminobenzylsulphanilic acid ; (4) a tertiary base prepared from methylhydroxyethylaniline and N-(dimethylaminobenzyl) sulphanilic acid; (5) a tertiary base from ethylhydroxyethylaniline and N-(dimethylaminobenzyl) sulphanilic acid ; (6) a tertiary base from methyl-#-α-dihydroxypropylaniline and N-(dimethylaminobenzyl)-sulphanilic acid; (7) a tertiary base from 2-amino-5-dimethylaminotoluene and N-(dimethylaminobenzyl) sulphanilic acid ; (8) a tertiary base from 1 mol. 4-dimethylaminoaniline and 2 mols. N-(dimethylaminobenzyl)-sulphanilic acid ; (9) a tertiary base from 1 mol. 4:4<SP>1</SP>-diaminodiphenylmethane and 4 mols. of N-(dimethylaminobenzylsulphanilic acid. Samples have been furnished under Sect. 2(5) of products prepared (a) by esterifying 4-dimethylamino - 4<SP>1</SP> - methylhydroxyethylaminodiphenylmethane with stearic acid and converting the resulting ester into a bis quaternary salt with dimethylsulphate ; the free bis quaternary base is then formed by means of alcoholic potash and reacted with stearic and acetic acids; (b) by esterifying 2:4-(p-dimethylaminobenzyl) N-methylhydroxyethylaniline, prepared from N-methylhydroxyethylaniline hydrochloride and twice the molecular quantity of N-(p-dimethylaminobenzyl) sulphanilic acid, with stearic acid chloride and converting the resulting ester into a tris quaternary salt with dimethylsulphate; the free base is then treated with stearic and acetic acids.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH538718X | 1938-12-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB538718A true GB538718A (en) | 1941-08-14 |
Family
ID=4518937
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3151?/39D Expired GB538718A (en) | 1938-12-06 | 1939-12-05 | Manufacture of acid salts of quaternary ammonium bases |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB538718A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2653156A (en) * | 1949-06-21 | 1953-09-22 | Lehn & Fink Products Corp | Quaternary ammonium compounds and process for producing the same |
US2775604A (en) * | 1953-02-09 | 1956-12-25 | Atlas Powder Co | Quaternary ammonium halides |
-
1939
- 1939-12-05 GB GB3151?/39D patent/GB538718A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2653156A (en) * | 1949-06-21 | 1953-09-22 | Lehn & Fink Products Corp | Quaternary ammonium compounds and process for producing the same |
US2775604A (en) * | 1953-02-09 | 1956-12-25 | Atlas Powder Co | Quaternary ammonium halides |
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