WO1993015170A1 - Procede de fabrication de sels de metaux alcalins de coloration claire stable, d'acides gras alpha-sulfones a activite detergente - Google Patents

Procede de fabrication de sels de metaux alcalins de coloration claire stable, d'acides gras alpha-sulfones a activite detergente Download PDF

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Publication number
WO1993015170A1
WO1993015170A1 PCT/EP1993/000159 EP9300159W WO9315170A1 WO 1993015170 A1 WO1993015170 A1 WO 1993015170A1 EP 9300159 W EP9300159 W EP 9300159W WO 9315170 A1 WO9315170 A1 WO 9315170A1
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WIPO (PCT)
Prior art keywords
alpha
alkali metal
formula
sulfofatty acid
salts
Prior art date
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PCT/EP1993/000159
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German (de)
English (en)
Inventor
Hans-Georg Rollberg
Herbert Lepper
Karl-Heinz Linde
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to EP93903230A priority Critical patent/EP0625183A1/fr
Priority to KR1019940702668A priority patent/KR950700395A/ko
Publication of WO1993015170A1 publication Critical patent/WO1993015170A1/fr

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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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids

Definitions

  • the invention relates to a process for the preparation of light-colored, color-stable alkali metal salts of wash-active alpha-sulfofatty acids, in which the alpha-sulfofatty acid ester salts or their mixtures are reacted in an aqueous medium with alkali metal hydroxides, the alkali metal alpha-sulfofatty acid salts formed precipitates from the aqueous phase and separates the solid products from the mother liquor.
  • Alkali metal salts of alpha-sulfofatty acids so-called “alpha-disalts” are usually produced by saponification or neutralization of alpha-sulfofatty acid ester salts and alpha-sulfofatty acids and, because of their good detergent properties, are important anionic surfactants for the production of washing and cleaning agents.
  • alpha-sulfofatty acid salts are either accumulate dark discoloration or discolour during storage and cannot be satisfactorily lightened by conventional bleaching processes.
  • the object of the invention was therefore to develop a method for producing light-colored, color-stable alpha-sulfofatty acid ester salts.
  • the invention relates to a process for the preparation of light-colored, color-stable alkali metal salts of wash-active alpha-sulfofatty acids of the formula (I),
  • Rl for a straight-chain or branched alkyl radical having 6 to 20 carbon atoms
  • R 1 and M have the meaning given for the formula (I) and R - is a straight-chain or branched alkyl radical having 1 to 6 C atoms, with strong alkalis at elevated temperature, which is distinguished by the fact that
  • alpha-sulfofatty acid ester salts of the formula (II) or their mixtures are reacted in an aqueous medium with an amount of alkali metal hydroxide such that at least 1 mole of A. talimetal hydroxide is available per mole of alpha-sulfofatty acid ester salt,
  • Velcro color numbers On the basis of the color behavior important for the assessment of detergent substances, usually declared as Velcro color numbers. it could be shown that the color quality of alpha-sulphonated ⁇ can be bis-alkali metal salts of fatty acid using the improved method erfindungsge ⁇ MAESSEN in an unforeseeable manner. This becomes particularly clear when unbleached alpha-sulfofatty acid alkali metal salts are subjected to the hydrolysis known from the prior art [DE-A-34 15 434] and used as a starting material for the process according to the invention.
  • a Velcro color number of 1000 was determined for a product made according to the prior art and left as a paste, while a product obtained and isolated from the same starting material by the process of the invention had a Velcro color number of 325.
  • Alpha sulfofatty acid ester salts are known substances which are accessible according to common methods of organic synthesis. The large-scale production of these compounds is currently carried out predominantly via the sulfation of corresponding fatty acid esters or fatty acid ester mixtures and subsequent neutralization of the sulfonation products with alkali metal hydroxide, preferably sodium hydroxide.
  • Suitable starting materials for this type of synthesis are preferably fatty acid esters whose fatty acid residues come from fats and / or oils of vegetable or animal origin, in particular esters of caprylic, capric, lauric, myristic, palmitic, stearic, Arachidonic and behenic acid.
  • esters of the fatty acids mentioned can form the basis for the alpha-sulfofatty acid ester salts as individual compounds.
  • fatty acid ester mixtures as can be obtained from natural fats and oils by transesterification with aliphatic alcohols having 1 to 6 carbon atoms, in the presence of suitable catalysts, the double bonds present in the fatty acid fraction being eliminated as completely as possible before or after the transesterification by hydrogenation.
  • Fatty acid ester mixtures which have an iodine number of less than 0.5 and in particular less than 0.1 are preferred.
  • Fatty acid alkyl esters can be used for the preparation of the alpha-sulfofatty acid ester salts both in the form of the mixtures obtained in their manufacture and in the form of certain fractions with a narrowed chain length range.
  • fatty acid alkyl ester fractions in which palmitic acid and stearic acid predominate and, for example, make up 90 to 97 percent by weight of the fatty acid fraction are of particular interest.
  • esters of synthetic, straight-chain or branched, saturated fatty acids with 8 to 22 carbon atoms are also suitable as the basis for the production of the alpha-sulfo fatty acid ester salts, provided that they are in alpha via a sulfatable carbon atom Position.
  • the alcohol content of the alpha-sulfofatty acid ester salts and the fatty acid esters on which they are based can originate from an alcohol from the group consisting of methanol, ethanol, n-propanol, n-butanol, n-pentanol, n-hexanol and their isomers.
  • Methyl esters preferably form the basis for the compounds of the formula (II).
  • the starting compounds of the formula (II) can be prepared from the fatty acid alkyl esters described above by one of the known processes by reaction with a suitable sulfonating agent and neutralization of the sulfonation product obtained with alkali metal hydroxide.
  • Chlorosulfonic acid and SO 3 gas are particularly suitable as sulfonating agents.
  • S03-inert gas mixtures in particular S03-air mixtures, are preferably used for the sulfonation.
  • the reaction is carried out under the conditions known for such sulfonations in conventional sulfonation reactors.
  • the fatty acid esters described above can be reacted at 70 to 130 ° C. in a falling film reactor with an S ⁇ 3 ⁇ air mixture in which the S ⁇ 3 fraction is 3 to 10% by volume for 10 to 20 minutes bring.
  • degrees of sulfonation of more than 90%, in particular 95 to 98%, can be achieved.
  • the products resulting from the sulfonation are liquid to solid and generally contain dissolved SO3 and SO3, which are converted into alkali metal sulfate or sulfite in the subsequent neutralization.
  • the viscosity maxima extend less far into the range of lower concentrations than for products based on fatty acids with a higher carbon number.
  • the concentration of the alkali metal hydroxide solutions used is designed so that aqueous alpha-sulfofatty acid ester-alkali metal salt compositions are formed whose concentrations are below or above the viscosity maxima. Both types of movable, pumpable solutions or pastes are suitable for use in the method according to the invention.
  • Aqueous compositions of this type are preferably used as the starting material, whose wash active substance content (WAS content) is in the range from 10 to 40% by weight, in particular in the range from 20 to 30% by weight, that is to say below the viscosity maxima.
  • WAS content wash active substance content
  • the ester sulfonate alkali metal salt solutions obtained in this way generally contain a proportion of salts of free alpha-sulfo fatty acids which, based on WAS, can make up about 5 to 30% by weight.
  • alpha-sulfofatty acid alkyl ester salts are suitable in the unbleached as well as in the bleached state as a starting material for the process according to the invention.
  • a number of known processes are available for the production of bleached alpha-sulfofatty acid ester salts. In this context reference is made, for example, to DE-A-33 19 591 and the patents cited therein.
  • Alpha-sulfofatty acid alkyl ester salts of the formula (II) whose fatty acid residues originate from fats and oils of vegetable or animal origin are advantageously used as starting material in the process according to the invention.
  • compounds of the formula (II) in which the radicals R! are straight-chain alkyl radicals having 12 to 20 carbon atoms, and in particular those in which R 1 is tetradecyl, hexadecyl and / or octadecyl. It is further preferred to use those alpha-sulfofatty acid alkyl ester salts of the formula (II) in which R 2 is methyl or ethyl, the methyl radical being of very particular interest.
  • the alpha-sulfofatty acid ester salts of the formula (II) are reacted in an aqueous medium with an amount of alkali metal hydroxide such that at least 1 mole of alkali metal hydroxide is available per mole of compounds of the formula (II).
  • Sodium hydroxide and potassium hydroxide are suitable as alkali metal hydroxides; from a practical point of view, sodium hydroxide is preferably used.
  • the alkali metal hydroxides are expediently in the form of concentrated aqueous solutions, for example in the form from 40 to 60% by weight solutions, mixed with the aqueous ester sulfonate salt compositions.
  • alkali metal hydroxide in a molar excess over the alpha-sulfofatty acid alkyl ester salt of the formula (II), the alkali metal hydroxide excess being kept within reasonable limits from an economic point of view. Accordingly, it is preferred to react the compounds of formula (II) with an amount of alkali metal hydroxide such that 1.1 to 1.5 moles of alkali metal hydroxide are available per mole of alpha-sulfofatty acid ester salt.
  • reaction of the compounds of formula (II) with alkali metal hydroxide is carried out at elevated temperature, in particular at 70 to 100 ° C., preferably at 85 to 95 ° C. At the temperatures indicated, the hydrolysis of the ester bonds proceeds rapidly. Adequate degrees of conversion are achieved from a reaction time of about 10 minutes. In order to convert the ester sulfonate salts into the alpha-sulfofatty acid bis-alkali salts as completely as possible, it is expedient to observe reaction times of 0.5 to 4 hours, preferably 1 to 2 hours.
  • reactors in which liquid reaction mixtures can be heated, cooled and vigorously mixed are suitable for carrying out the reaction, for example double-walled stirred kettles in which the content can be appropriately heated using liquid heat transfer media.
  • Such reactors are expediently equipped with a device in which the Reaction released, with the vapor phase distilling off alcohol can be condensed.
  • the alkali metal alpha-sulfofatty acid salts of the formula (I) formed are precipitated from the aqueous phase.
  • part of the bis-alkali metal salts formed is excreted as a solid product at the reaction temperatures of 70 to 100 ° C. which are preferably considered.
  • the reaction mixture is cooled to temperatures below 20 ° C.
  • the solid products can be separated from the mother liquor by the methods of the prior art known for such separation operations.
  • the solid alpha-sulfofatty acid bis-alkali metal salts of the formula (I) can be isolated from the reaction mixture, for example by centrifugation or preferably by filtration.
  • Adhering alkaline mother liquor can be removed by washing once or several times with a suitable but cold washing liquid, for example with water. After renewed isolation, the solid products obtained in this way can, if desired, be supplied in a moist state or after being slurried with water as a suspension for their use, for example as a detergent component.
  • Dry free-flowing products which are easily accessible are advantageous by subjecting the moist salts to one of the known drying processes, for example drying in a hot air stream at 70 to 80 ° C., and without them Redissolution directly z.
  • B. Powder detergents can be added.
  • the majority of the alpha-sulfofatty acid alkyl ester salts used are converted into light-colored alpha-sulfofatty acid bis-all-potassium metal salts in the course of the process described above.
  • the alpha-sulfofatty acid ester salts used have not reacted completely with the alkali metal hydroxide, so that the filtrate contains a more or less large amount of unhydrolyzed alpha-sulfofatty acid ester salts.
  • further alkali metal hydroxide can be added to the filtrate and process steps a) to c) repeated.
  • Disalze are characterized by light colors, storage stability and good detergent properties. They are suitable for the production of detergents and cleaning agents, in which they can be present in amounts of 1 to 25, preferably 5 to 15% by weight, based on the detergent.
  • Velcro color numbers given in the examples below were each measured on solutions of the products containing 5% by weight WAS in a mixture of water and ethanol (volume ratio 1: 1) at pH 7 in a 4 cm cuvette .
  • Aqueous solutions of alpha-sulfofatty acid bis-sodium salts as can be obtained by refluxing corresponding alpha-sulfofatty acid ester sodium salts with excess dilute sodium hydroxide solution, were used as comparison substances.
  • a technical grade alpha-sulfofatty acid methyl ester sodium salt paste with a detergent content (WAS content) of 31.5% by weight was used as the starting material, 19.3% of the existing WAS consisting of alpha-sulfofatty acid bis-sodium salts.
  • This ester sulfonate paste was obtained by sulfonating a fatty acid methyl ester mixture based on naturally occurring fatty acids (chain length distribution in the fatty acid residue in% by weight: 0.5 0 ⁇ 2 / 4.0 C14; 27.5 C15; 67.0 Cis?
  • Klett color number of 1000 was measured on an alpha-sulfofatty acid bis-sodium salt prepared according to the prior art from the above-mentioned ester sulfonate paste and left as a paste.
  • a technical grade alpha-sulfofatty acid methyl ester sodium salt paste with a WAS content of 37.5% by weight was used as the starting material, 22.2% of the existing WAS consisting of alpha-sulfofatty acid bis-sodium salts.
  • This ester sulfonate paste was obtained by conventional sulfonation of a fatty acid methyl ester mixture based on naturally occurring fatty acids (chain length distribution in the fatty acid residue in% by weight: 2.8 C14; 61.4 C16 35.1 Cis, 0.7 C20) with an SO 3 air Mixture up to a degree of sulfonation of 95.2%, subsequent neutralization and bleaching with NaOCl and H2O2 according to DE-A-33 19 591.
  • a Klett color number of 120 was measured on an alpha-sulfofatty acid bis-sodium salt prepared according to the prior art from the above-mentioned ester sulfonate paste and left as a paste.
  • a technical grade alpha-sulfofatty acid ethyl ester sodium salt paste with a WAS content of 30.8% by weight was used as the starting material, with 26.2% of the existing WAS consisting of alpha-sulfofatty acid bis-sodium salts.
  • This ester sulfonate paste was made from a fatty acid methyl ester mixture based on naturally occurring fatty acids (chain length distribution in the fatty acid residue in% by weight: 3.0 C14 47.0 C15; 49.0 Cig; 1.0 C20) by means of convergent sulfation with an S ⁇ 3- Air mixture up to a degree of sulfonation of 91.6%, subsequent neutralization and bleaching with NaOCl and H2O2 according to DE-A-33 19 591 were obtained.
  • the filtrate combined with the washing water was mixed with a further 2.3 g (0.06 mol) of sodium hydroxide in the form of a 50% strength by weight aqueous solution, heated to 95 ° C. for 1 h and then cooled to 18 ° C.
  • light-colored crystals separated out, which were separated from the mother liquor by filtration and washed twice with cold water.
  • Klett color number of 94 was measured on an alpha-sulfofatty acid bis-sodium salt prepared according to the prior art from the above-mentioned ester sulfonate paste and left as a paste.
  • a technical grade alpha-sulfofatty acid methyl ester sodium salt paste with a WAS content of 63.2% by weight was used as the starting material, 18.6% of the existing WAS consisting of alpha-sulfofatty acid bis-sodium salts.
  • This ester sulfonate paste was obtained by conventional sulfonation of a fatty acid methyl ester mixture based on naturally occurring fatty acids (chain length distribution in% by weight: 1.9 Cg_i4; 63.9 C15; 33.8 C13; 0.4 C20) with an S ⁇ 3- Air mixture up to a degree of sulfation of 93.8%, subsequent neutralization and bleaching with NaOCl and H2O2 according to DE-A-33 19 591.
  • the filtrate combined with the washing water was mixed with a further 2.1 g (0.05 mol) of sodium hydroxide in the form of a 50% strength by weight aqueous solution and worked up in the same way as described in Example 2.
  • a further 18.5 g of solid substance with an alpha-sulfofatty acid bis-sodium salt content of 85.0% by weight (6.2% of theory) were obtained.
  • the overall yield was 96% of theory.
  • a Klett color number of 60 was measured on an alpha-sulfofatty acid bis-sodium salt prepared according to the prior art from the above-mentioned ester sulfonate paste and left as a paste.

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

Des sels de métaux alcalins de coloration claire stable, d'acides gras alpha-sulfonés à activité détergente sont obtenus a) en amenant à réagir des sels d'esters d'acides gras alpha-sulfonés ou des mélanges de ceux-ci, en milieu aqueux, avec une quantité d'hydroxyde de métal alcalin, telle qu'on dispose d'au moins 1 mole d'hydroxyde de métal alcalin par mole d'ester d'acide gras alpha-sulfoné, b) en précipitant de la phase aqueuse les sels de métaux alcalins d'acides gras alpha-sulfonés formés et c) en séparant les produits solides de la lessive-mère.
PCT/EP1993/000159 1992-02-03 1993-01-25 Procede de fabrication de sels de metaux alcalins de coloration claire stable, d'acides gras alpha-sulfones a activite detergente WO1993015170A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP93903230A EP0625183A1 (fr) 1992-02-03 1993-01-25 Procede de fabrication de sels de metaux alcalins de coloration claire stable, d'acides gras alpha-sulfones a activite detergente
KR1019940702668A KR950700395A (ko) 1992-02-03 1993-01-25 세척 활성 α-술폰지방산의 담색의, 색안정성 알칼리 금속염의 제조 방법(METHOD OF PRODUCING PALE-COLOURED, COLOUR-STABLE ALKALI-METAL SALTS OF WASHING-ACTIVE α-SULPHONIC FATTY ACIDS)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4203001A DE4203001A1 (de) 1992-02-03 1992-02-03 Verfahren zur herstellung hellfarbiger, farbstabiler alkalimetallsalze waschaktiver alpha-sulfofettsaeuren
DEP4203001.3 1992-02-03

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WO1993015170A1 true WO1993015170A1 (fr) 1993-08-05

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PCT/EP1993/000159 WO1993015170A1 (fr) 1992-02-03 1993-01-25 Procede de fabrication de sels de metaux alcalins de coloration claire stable, d'acides gras alpha-sulfones a activite detergente

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EP (1) EP0625183A1 (fr)
KR (1) KR950700395A (fr)
AU (1) AU3451293A (fr)
DE (1) DE4203001A1 (fr)
MX (1) MX9300580A (fr)
WO (1) WO1993015170A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3104247A (en) * 1962-02-01 1963-09-17 Richardson Co Process for preparing alpha sulfo fatty acids and salts thereof
GB1214714A (en) * 1968-04-29 1970-12-02 Procter & Gamble Ltd Process for preparing monosodium alpha-sulphocarboxylic acids
DE3415434A1 (de) * 1983-06-30 1985-01-17 Lion Corp., Tokio/Tokyo Fluessiges wasch- und reinigungsmittel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3104247A (en) * 1962-02-01 1963-09-17 Richardson Co Process for preparing alpha sulfo fatty acids and salts thereof
GB1214714A (en) * 1968-04-29 1970-12-02 Procter & Gamble Ltd Process for preparing monosodium alpha-sulphocarboxylic acids
DE3415434A1 (de) * 1983-06-30 1985-01-17 Lion Corp., Tokio/Tokyo Fluessiges wasch- und reinigungsmittel

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J. AM. OIL CHEM. Bd. 52, September 1975, Seiten 323 - 329 W. STEIN ET AL. '@-Sulfonated Fatty Acids and Esters: Manufacturing Process, Properties, and Applications' *

Also Published As

Publication number Publication date
DE4203001A1 (de) 1993-08-05
KR950700395A (ko) 1995-01-16
EP0625183A1 (fr) 1994-11-23
AU3451293A (en) 1993-09-01
MX9300580A (es) 1993-09-01

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