GB824447A - Improved process of preparing anionic surface active agents - Google Patents
Improved process of preparing anionic surface active agentsInfo
- Publication number
- GB824447A GB824447A GB23955/57A GB2395557A GB824447A GB 824447 A GB824447 A GB 824447A GB 23955/57 A GB23955/57 A GB 23955/57A GB 2395557 A GB2395557 A GB 2395557A GB 824447 A GB824447 A GB 824447A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- hydroxy
- reaction
- sulphonic
- acids
- 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
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/10—Running-in-oil ; Grinding
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Abstract
Anionic surface-active agents prepared by reaction of carboxylic acids containing at least 8 carbon atoms with compounds of general formula <FORM:0824447/III/1> where R = H1 or C1-C2 alkyl, and M = alkali metal, alkaline earth metal or a sterically hindered secondary or tertiary amine (see Group IV (b)) are used as additives to petroleum lubricating oils, for breaking petroleum emulsions and, in aqueous solution, emulsions or in oils, used for the milling or cutting of metals.ALSO:The invention comprises a process for the preparation of esters of a 2-hydroxy alkane sulphonic acid, by reaction of one mol. of a salt of such an acid, of general formula <FORM:0824447/IV (b)/1> where R is hydrogen, methyl or ethyl and M is an alkali metal, alkaline earth metal or a sterically hindered secondary or tertiary amine with 1 to 10 mols. of an aliphatic, aromatic or alicyclic carboxylic acid having at least eight carbon atoms, at 185-300 DEG C. in the presence of o-phosphoric acid in an amount from 2-2 1/2 % by weight of the carboxylic acid, and the reaction is carried out at atmospheric pressure in an inert atmosphere of, e.g., nitrogen, carbon dioxide or steam, at a pH of 2.0 to 5. The reaction time is usually between 1/2 and 2 hours. Monocarboxylic acids specified as starting materials are caprylic, pelargonic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic, lauronolic, cycloalkane or heptane carboxylic, o- or mtoluic, cumic, phenylacetic, tall oil, hydrogenated tall and tallow, naphthenic, abietic, dodecylbenzoic, nonylbenzoic, octylbenzoic, and nonylnaphthoic acids. Acids from oxo alcohols, and aldehydes, or from oxidized petroleum fractions may be used, as well as acid mixtures from natural plant and animal oils such as olive, tallow, castor, peanut, coconut, soybean, cottonseed, ucahuba, linseed, cod, herring, menhaden, neetsfoot, sperm, palm, corn, butter, babassu, kapok, hempseed, mustard, rubberseed, rape, safflower, and sesame oils. 2-Hydroxyalkane sulphonic acid salts specified, which may be condensed with the above monocarboxylic acids, are the calcium, magnesium, barium, lithium, sodium, potassium, trioctylamine, N,N-diphenylmethylamine, N,N - dimethyloctadecylamine, N,N - dioctodecylethylamine, and N,N-dihexadecylmethylamine salts of isethionic, 2-hydroxy-3-butane sulphonic, 2-hydroxy-propane-sulphonic, and 2-hydroxy-1-butane sulphonic acids. These salts may be used as aqueous solutions or as dry powders; in the former case the water is removed during the reaction in the presence of a monocarboxylic acid. Examples are given of the reaction between (A) a coconut oil fatty acid and sodium isethionate, (1) in the absence of a catalyst, and (2) in the presence of boric acid at pH 6.6, (3) in accordance with the invention; (B) lauric acid and sodium isethionate; (C) stearic acid and sodium isethionate; (D) a coconut fatty acid and (1) sodium BETA-methylisethionate, (2) the potassium salt of 2-hydroxypropane sulphonic acid, (3) the sodium salt of 2-hydroxy-1-butane sulphonic acid; (E) lauric acid and the tri-octylamine salt of 2-hydroxy-1 -butane sulphonic acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US824447XA | 1956-08-10 | 1956-08-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB824447A true GB824447A (en) | 1959-12-02 |
Family
ID=22171260
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23955/57A Expired GB824447A (en) | 1956-08-10 | 1957-07-29 | Improved process of preparing anionic surface active agents |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB824447A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3098817A (en) * | 1960-10-28 | 1963-07-23 | Armour & Co | Phosphate ore flotation process |
US4405526A (en) * | 1981-08-24 | 1983-09-20 | Lever Brothers Company | Process for producing directly esterified fatty acyl isethionate by a mixed zinc oxide-sulfonic acid catalyst |
EP0735020A2 (en) * | 1995-03-29 | 1996-10-02 | Hoechst Aktiengesellschaft | Process for the preparation of acyloxyalkanesulfonates |
WO2012175935A1 (en) | 2011-06-20 | 2012-12-27 | Innospec Limited | Composition comprising fatty acyl isethionate and synthetic wax and method producing the same |
US9493716B2 (en) | 2008-07-11 | 2016-11-15 | Innospec Limited | Fuel composition with enhanced low temperature properties |
-
1957
- 1957-07-29 GB GB23955/57A patent/GB824447A/en not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3098817A (en) * | 1960-10-28 | 1963-07-23 | Armour & Co | Phosphate ore flotation process |
US4405526A (en) * | 1981-08-24 | 1983-09-20 | Lever Brothers Company | Process for producing directly esterified fatty acyl isethionate by a mixed zinc oxide-sulfonic acid catalyst |
EP0735020A2 (en) * | 1995-03-29 | 1996-10-02 | Hoechst Aktiengesellschaft | Process for the preparation of acyloxyalkanesulfonates |
EP0735020A3 (en) * | 1995-03-29 | 2001-09-19 | Clariant GmbH | Process for the preparation of acyloxyalkanesulfonates |
US9493716B2 (en) | 2008-07-11 | 2016-11-15 | Innospec Limited | Fuel composition with enhanced low temperature properties |
WO2012175935A1 (en) | 2011-06-20 | 2012-12-27 | Innospec Limited | Composition comprising fatty acyl isethionate and synthetic wax and method producing the same |
US9593298B2 (en) | 2011-06-20 | 2017-03-14 | Innospec Limited | Composition comprising fatty acyl isethionate and synthetic wax and method producing the same |
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