US3047509A - Process for preparing a mixture of soap and fatty-acyl-aminomethane sulfonate - Google Patents

Process for preparing a mixture of soap and fatty-acyl-aminomethane sulfonate Download PDF

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Publication number
US3047509A
US3047509A US747844A US74784458A US3047509A US 3047509 A US3047509 A US 3047509A US 747844 A US747844 A US 747844A US 74784458 A US74784458 A US 74784458A US 3047509 A US3047509 A US 3047509A
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United States
Prior art keywords
soap
reaction
mixture
amide
fatty
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Expired - Lifetime
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US747844A
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English (en)
Inventor
Alsbury Allan
Kenneth A Phillips
Taylor Bernard
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Lever Brothers Co
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Lever Brothers Co
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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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • 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
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides

Definitions

  • This invention relates to an improvement in the preparation ofalkali-metal salts of fatty-acyl-aminomethane sulphonates of formula R-CO-NH'CH -SO M where R-CO is the acyl radical of a fatty acid and M is sodium or potassium.
  • Fatty acyl-aminomethane sulphonates have in the past been prepared by the reaction of a fatty amide with between about 0.8 and about 2 molecular proportions of sodium or potassium formaldehyde bisulp-hite at temperatures of from about 150 to 210 C.
  • the reaction mixture is initially quite fluid at the reaction temperature and may be handled in conventional jacketed vessels with light stirring gear, but, as the reaction proceeds, the mixture becomes more and more viscous and finally so stiff that it becomes incapable of being stirred with such gear and diificult to remove from the reaction vessel.
  • the react-ion mixture may be transferred from the first reaction vessel, after the reaction has proceeded to a certain degree but before the mixture has become too viscous to run from the vessel, into a second reaction vessel, of the kneader-mixer type with powerful sigma-shaped stirrers, to complete the reaction, but this process involves more labour, plant and power than is desirable.
  • fatty-acylsaminomethane sulphonates are required in the form of mixtures with soap.
  • the present invention provides, therefore, a process for the preparation of mixtures containing fatty-acylaminomethane sulphonates and soap in which fatty amides are caused to react with from 0.8 to 1.2 mols of sodium or potassium formaldehyde bisulphite in the presence of free fatty acid and soap, and the free fatty acid is subsequently neutralised.
  • the minimum amount of free fatty acid required to maintain the reaction mixture in the fluid state depends to some extent upon the reaction conditions, particularly the actual composition of the reaction mixture, the temperature of the reaction, and the extent to which the escape of water from the reaction mixture is allowed or promoted: a reaction mixture from which the water of reaction is continuously removed by a current of inert gas, for instance, will require more fatty acid to maintain fluidity at a given reaction temperature than one in which some water is retained in the mixture.
  • the amount of free fatty acid should be not less than about 15% by weight of the amide used.
  • the maximum amount of free fatty acid that can be used is not critical but excessive amounts may reduce the conversion of the amide to fatty-acylatent aminomethane sulphonate and may in any case give final products of restricted usefulness. Normally, therefore, the maximum amount of free fatty acid will be about 40% by weight of the amide.
  • the soap present should not exceed the amount by which the free fatty acid exceeds 14% by weight of the fatty amide. Since the upper limit for free fatty acid is about 40%, the upper limit of soap is about 26%, but normally much less is required.
  • the process will normally be applied to the preparation of mixtures containing sodium fatty-acyl-aminomethane sulphonates derived from acids containing about 10 to 18, preferably 12 to 14, carbon atoms.
  • Mixtures of such amides may be used, particularly mixtures such as may be obtained from the the mixed fatty acids of natural oils such as palm oil, palm kernel oil, coconut-oil, cottonseedoil, groundnut-oil and bone grease. It is preferred to use amides derived mainly or entirely from the fatty acids of palm kernel oil or coconut oil.
  • the fatty acids which are added in the process of the invention may also contain from 10 to 18 carbon atoms and may again be mixtures such as those derived from any of the usual natural fats or oils.
  • Commercial fatty amides normally contain a proportion of free fatty acids and the added free fatty acid may be the same as or different from that already present in the amide which, however, must be included when reckoning the amount of free fatty acid present.
  • the soap which is used in the process of the invention may again be derived from any fatty acid having from about 10 to 18 carbon atoms in the molecule, including mixtures of acids such as those obtained from natural oils, which may be the same as or different from the free fatty acid also present. Normally it is most convenient to add free fatty acid to the reaction mixture and to convert an appropriate proportion of this to soap in situ.
  • the cation of the soap may be an alkali metal, ammonium or an organic amine such as di-cyclohexylamine.
  • the soap should be water soluble. It is preferred to use the sodium soaps, which are conveniently made by adding the appropriate amount of sodium carbonate to a mixture of the free fatty acid and the other ingredients.
  • the reaction is carried out in conventional jacketed mixing vessels with paddle-type stirring gear at a temperature of C. to 210 C., preferably C. to C., and is preferably carried out in an inert atmosphere, for example an atmosphere of nitrogen, carbon dioxide or steam.
  • the time during which the reactants are maintained at the desired temperature depends upon the actual reaction temperature selected and on the proportions of the various ingredients of the reaction mixture.
  • a temperature of 175 C. to 180 3., for instance, a time of between 1 and 3 hours is usually satisfactory, the conversion having then reached its maximum.
  • the reaction mixture is still sufficiently fluid to be run from the mixing vessel, preferably under an inert gas blanket.
  • reaction product After cooling it may be fully or partially neutralised, for example by the addition of sodium carbonate or sodium hydroxide, and the resulting mixture subjected to any desired processing.
  • the reaction product, after neutralisation may be purified to some extent from the formaldehyde bisulphite and other water-soluble impurities by dissolving or slurrying it with hot Water and graining it out by the addition of sodium chloride or brine in accordance with the normal soap-making technique.
  • the grained-out mixture may contain a somewhat higher salt content, eg. 1.52.0%, than is normal for a grained-out soap but any tendency for this to cause efilorescence when the mixture is used for solid compositions may be counteracted :by adding small amounts, eg. 3% of sodium toluene sulphonate or sodium xylene sulphonate.
  • a process for the preparation of a mixture comprising a water soluble soap and an alkali metal salt of a fatty-acyl-aminomethane sulphonate selected from the group consisting of sodium and potassium salts and having from 10 to 18 carbon atoms in the acyl radical, said process comprising reacting a fatty amide having from 10 to 18 carbon atoms with from 0.8 to 1.2 molecular proportions of an alkali metal formaldehyde bisulphite selected from the group consisting of sodium formaldehyde bisulphite and potassium formaldehyde bisulphite, in the presence of: (a) from 15 to 40%, by weight of the amide, of a free fatty acid having from 10 to 18 carbon atoms, and (b) from about 1 to 26% by weight of the amide of a water soluble alkali metal soap having from 10 to 18 carbon atoms, the reaction being carried out at a temperature of from C. to 210 C.
  • a process for the preparation of a mixture comprising a water soluble soap and an alkali metal salt of a fatty-acyl-aminomethane sulphonate selected from the group consisting of sodium and potassium salts and having from 10 to 18 carbon atoms in the acyl radical, said process comprising reacting a fatty amide having from 10 to 18 carbon atoms with approximately an equal molecular proportion of an alkali metal formaldehyde bisulphite selected from the group consisting of sodium formaldehyde bisulphite and potassium formaldehyde bisulp-hite, in the presence of: (a) about 35%, by weight of the amide, of a free fatty acid having from 10 to 18 carbon atoms, and (b) about 10% by weight of the amide of a water soluble alkali metal soap having from 10 to 18 carbon atoms, the reaction taking place at a temperature of from to C.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US747844A 1957-07-15 1958-07-11 Process for preparing a mixture of soap and fatty-acyl-aminomethane sulfonate Expired - Lifetime US3047509A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB22304/57A GB830054A (en) 1957-07-15 1957-07-15 Improvements in or relating to detergent preparations

Publications (1)

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US3047509A true US3047509A (en) 1962-07-31

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US747844A Expired - Lifetime US3047509A (en) 1957-07-15 1958-07-11 Process for preparing a mixture of soap and fatty-acyl-aminomethane sulfonate

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US (1) US3047509A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE1074797B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (1) FR1199892A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB830054A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NL (1) NL229598A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3344174A (en) * 1962-08-21 1967-09-26 Monsanto Co Vicinal acylamido sulfonate compounds
US3494869A (en) * 1966-07-11 1970-02-10 Lever Brothers Ltd Superfatted soap bars and process for their preparation
US4618450A (en) * 1984-11-07 1986-10-21 The Lubrizol Corporation Aqueous systems containing amino sulfonic acid derivatives of carboxylic acids
US4786720A (en) * 1986-07-25 1988-11-22 Westvaco Corporation Sulfomethylated lignin amines
US4859362A (en) * 1986-07-25 1989-08-22 Westvaco Corporation Sulfomethylated lignin amines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8525503D0 (en) * 1985-10-16 1985-11-20 Unilever Plc Detergent component

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2313695A (en) * 1937-06-10 1943-03-09 Gen Aniline & Film Corp Process of preparing amino-sulphonic acids substituted in the amino group by acyl radicals of fatty acids
US2366452A (en) * 1939-08-02 1945-01-02 Gen Aniline & Film Corp Process of preparing condensation products
US2857370A (en) * 1954-11-22 1958-10-21 Gen Aniline & Film Corp Process of preparing ester and amide type anionic surface active agents
US2880219A (en) * 1954-11-22 1959-03-31 Gen Aniline & Film Corp Production of n-acyl taurides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2313695A (en) * 1937-06-10 1943-03-09 Gen Aniline & Film Corp Process of preparing amino-sulphonic acids substituted in the amino group by acyl radicals of fatty acids
US2366452A (en) * 1939-08-02 1945-01-02 Gen Aniline & Film Corp Process of preparing condensation products
US2857370A (en) * 1954-11-22 1958-10-21 Gen Aniline & Film Corp Process of preparing ester and amide type anionic surface active agents
US2880219A (en) * 1954-11-22 1959-03-31 Gen Aniline & Film Corp Production of n-acyl taurides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3344174A (en) * 1962-08-21 1967-09-26 Monsanto Co Vicinal acylamido sulfonate compounds
US3494869A (en) * 1966-07-11 1970-02-10 Lever Brothers Ltd Superfatted soap bars and process for their preparation
US4618450A (en) * 1984-11-07 1986-10-21 The Lubrizol Corporation Aqueous systems containing amino sulfonic acid derivatives of carboxylic acids
US4786720A (en) * 1986-07-25 1988-11-22 Westvaco Corporation Sulfomethylated lignin amines
US4859362A (en) * 1986-07-25 1989-08-22 Westvaco Corporation Sulfomethylated lignin amines

Also Published As

Publication number Publication date
GB830054A (en) 1960-03-09
NL229598A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE1074797B (de) 1960-02-04
FR1199892A (fr) 1959-12-16

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