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GB760121A - Bis-decyl and bis-tridecyl esters of sulfosuccinic acid and preparation thereof - Google Patents

Bis-decyl and bis-tridecyl esters of sulfosuccinic acid and preparation thereof

Info

Publication number
GB760121A
GB760121A GB24374/53A GB2437453A GB760121A GB 760121 A GB760121 A GB 760121A GB 24374/53 A GB24374/53 A GB 24374/53A GB 2437453 A GB2437453 A GB 2437453A GB 760121 A GB760121 A GB 760121A
Authority
GB
United Kingdom
Prior art keywords
bis
alcohol
ammonium
sodium
alkali metal
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
GB24374/53A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB760121A publication Critical patent/GB760121A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton

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)
  • Detergent Compositions (AREA)

Abstract

The invention comprises bis-esters of sulphosuccinic acid, of the general formula <FORM:0760121/IV(b)/1> wherein Me represents an alkali metal or ammonium and R the radical of a primary alcohol having 10-19 (preferably 10-13) carbon atoms in the molecule and having the formula <FORM:0760121/IV(b)/2> wherein one X represents -CH2OH and the other hydrogen, R2 represents hydrogen or methyl, and n is whole number from 1-4 inclusive, and the preparation thereof by esterifying the appropriate alcohol with maleic acid or anhydride or fumaric acid (preferably at 60-190 DEG C. in the presence of an acidic catalyst), and sulphonating the resulting bis-ester with an alkali metal or ammonium bisulphite (preferably at 50-120 DEG C.). Suitable alcohols are distillation fractions of the products obtained by the oxo process from polypropylenes, polybutylenes and propylene-butylene copolymers. Suitable sulphonating agents are sodium and ammonium bisulphite or metabisulphite. In examples: (1) a C13 alcohol fraction is refluxed with maleic anhydride in toluene in the presence of p-toluenesulphonic acid and the product is refluxed with sodium metabisulphite in aqueous ethanol; (2) a slightly different C13 alcohol fraction is similarly treated, except that concentrated sulphuric acid is used as the esterification catalyst; (3) a C10 alcohol fraction is treated as in (2). Specification 446,568, [Group IV], is referred to.ALSO:Detergent compositions comprises one or more sulphosuccinic esters of the formula <FORM:0760121/III/1> (wherein Me represents an alkali metal or ammonium and R the radical of a primary alcohol having 10-19 (preferably 10-13) carbon atoms in the molecule and having the formula <FORM:0760121/III/2> wherein one X represents -CH2OH and the other hydrogen, R2 represents hydrogen or methyl, and n is a whole number from 1-4 inclusive) in admixture with one or more alkali metal or ammonium benzoates. The amount of benzoate is preferably 5-50 per cent of the weight of sulphosuccinate, and the compositions may also contain other ingredients such as sodium phosphate, soap, other detergents and inorganic fillers. The compositions may be prepared by mixing the ingredients in the presence of water or an aqueous organic solvent (e.g. an aqueous alcohol) and evaporating to dryness, e.g. in a tray-drier or on a revolving drum from which the solid material may be scraped off in thin flakes. In an example, an aqueous solution of sodium bis-tridecyl sulphosuccinate and sodium benzoate is spray dried by atomizing it in a rising vortex of hot air or hot products of combustion at 600-700 DEG F. Specification 446,568 is referred to.
GB24374/53A 1952-09-23 1953-09-03 Bis-decyl and bis-tridecyl esters of sulfosuccinic acid and preparation thereof Expired GB760121A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US760121XA 1952-09-23 1952-09-23

Publications (1)

Publication Number Publication Date
GB760121A true GB760121A (en) 1956-10-31

Family

ID=22129371

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24374/53A Expired GB760121A (en) 1952-09-23 1953-09-03 Bis-decyl and bis-tridecyl esters of sulfosuccinic acid and preparation thereof

Country Status (1)

Country Link
GB (1) GB760121A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3401059A (en) * 1965-01-22 1968-09-10 John A. Casey Manufacture of sugar
EP0130818A2 (en) 1983-07-01 1985-01-09 Unilever N.V. Process for the handling of dialkyl sulphosuccinates
EP0458099A2 (en) * 1990-05-25 1991-11-27 Pfersee Chemie GmbH Process for the preparation of salts of sulfosuccinic acid dialkylesters
US5908582A (en) * 1993-08-02 1999-06-01 Henkel Kommanditgesellschaft Auf Aktien Liquid formulations containing sulfosuccinic acid diester

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3401059A (en) * 1965-01-22 1968-09-10 John A. Casey Manufacture of sugar
EP0130818A2 (en) 1983-07-01 1985-01-09 Unilever N.V. Process for the handling of dialkyl sulphosuccinates
EP0458099A2 (en) * 1990-05-25 1991-11-27 Pfersee Chemie GmbH Process for the preparation of salts of sulfosuccinic acid dialkylesters
EP0458099A3 (en) * 1990-05-25 1992-03-04 Chemische Fabrik Pfersee Gmbh Process for the preparation of salts of sulfosuccinic acid dialkylesters
US5908582A (en) * 1993-08-02 1999-06-01 Henkel Kommanditgesellschaft Auf Aktien Liquid formulations containing sulfosuccinic acid diester

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