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WO1993009091A1 - Procede de fabrication de pates d'alkenylsulfate de couleur claire - Google Patents

Procede de fabrication de pates d'alkenylsulfate de couleur claire Download PDF

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Publication number
WO1993009091A1
WO1993009091A1 PCT/EP1992/002499 EP9202499W WO9309091A1 WO 1993009091 A1 WO1993009091 A1 WO 1993009091A1 EP 9202499 W EP9202499 W EP 9202499W WO 9309091 A1 WO9309091 A1 WO 9309091A1
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WO
WIPO (PCT)
Prior art keywords
alcohols
lauric
fatty alcohols
carbon atoms
formula
Prior art date
Application number
PCT/EP1992/002499
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German (de)
English (en)
Inventor
Bert Gruber
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to JP5508156A priority Critical patent/JPH07500829A/ja
Priority to EP92922761A priority patent/EP0613460A1/fr
Publication of WO1993009091A1 publication Critical patent/WO1993009091A1/fr

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Classifications

    • 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
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids

Definitions

  • the invention relates to a process for producing light-colored alkenyl sulfate pastes by sulfonating lauric alcohols and subsequent neutralization and hydrolysis with aqueous bases.
  • Anionic surfactants of the alkyl sulfate type in particular those which contain 16 to 18 carbon atoms in the fat residue, show excellent detergent properties and are suitable for the production of detergents, dishwashing detergents and cleaning agents.
  • These substances are generally prepared from fatty alcohols which are first converted into the corresponding sulfuric acid semiesters using suitable sulfonating agents, for example gaseous sulfur trioxide, and then neutralized with bases, aqueous pastes of different solids content being obtained [J.Am .011.
  • alkyl sulfates based on saturated is limited by the fact that aqueous pastes of these products are gel-like to highly viscous and no longer pumpable even at solids contents of 30 to 40% by weight, so that, for example, the spray drying for the production of powder detergents for further processing is out of the question.
  • alkenyl sulfates that is to say sulfation products of unsaturated fatty alcohols, which in comparison have a significantly lower viscosity than the saturated products and, at paste concentrations of 50% by weight, are also flowable at room temperature.
  • alkenyl sulfates have the disadvantage that they have a significantly poorer color quality than alkyl sulfates and can therefore, for aesthetic reasons, generally only be used after complex bleaching operations.
  • the object of the invention was therefore to develop a process for producing light-colored alkenyl sulfate pastes which is free from the disadvantages described. Description of the invention
  • the invention relates to a process for producing light-colored alkenyl sulfate pastes, which is characterized in that it contains lauric alcohols
  • R 1 represents a linear, unsaturated, aliphatic hydrocarbon radical having 16 to 22 carbon atoms and 1, 2 or 3 double bonds and
  • R 2 represents a linear or branched, saturated, aliphatic hydrocarbon radical having 12 to 22 carbon atoms
  • the invention is based on the knowledge that the color of sulfonation products becomes more unsaturated Fatty alcohols deteriorate abruptly if the feedstocks exceed a critical iodine number of 50 and a critical content of polyunsaturated components of 1.5% by weight.
  • lauric alcohols are vegetable fatty alcohols, for. B. to understand on the basis of palm oil, palm kernel oil or Ko ⁇ kosöl, which have an iodine number in the range of 10 to 50 and a proportion of polyunsaturated components from 0.1 to 1.5 wt .-% - based on the fatty alcohol .
  • Typical examples of unsaturated fatty alcohols of the formula (I) which may be present in the lauric alcohols are palmitoleyl alcohol, oleyl alcohol, elaidyl alcohol, petroseline alcohol, linolyl alcohol, linolenyl alcohol, gadoleyl alcohol or erucyl alcohol.
  • the lauric alcohols preferably contain oleyl alcohol.
  • Saturated fatty alcohols of the formula (II), which may also be constituents of the lauric alcohols, are, for example, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachyl alcohol and behenyl alcohol.
  • the lauric alcohols preferably contain cetyl and / or stearyl alcohol.
  • the sulfonation of the lauric alcohols can take place in the manner known for fatty acid lower alkyl esters [J. Falbe (ed.), "Surfactants in consumer products", Springer Verlag, Berlin-Hei ⁇ delberg, 1987, p. 61], with continuous working reactors which operate according to the falling film principle are preferred.
  • the lauric alcohols and the sulfur trioxide can be used in a molar ratio of 1: 0.95 to 1: 1.3, preferably 1: 1.05 to 1: 1.1.
  • the sulfonation reaction can be carried out at temperatures T 1 of 25 to 90 ° C., but in particular 30 to 50 ° C.
  • the acidic sulfonation products obtained in the sulfonation are stirred into aqueous bases, neutralized and hydrolyzed at the same time in order to prevent the compounds from being acidified again.
  • the neutralization / hydrolysis can be carried out at temperatures from 70 to 90 ° C.
  • proportions of sultons formed are hydrolyzed to form sulfonates without the sulfate group being split off.
  • the acidic sulfonation products are neutralized immediately after leaving the reactor without further cooling, the hydrolysis also taking place at the same time.
  • bases for the neutralization come alkali metal hydroxides such as sodium, potassium and lithium hydroxide, alkaline earth metal oxides and hydroxides such as magnesium oxide, magnesium hydroxide, calcium oxide and calcium hydroxide, ammonia, mono-, di- and tri-C2-4-alkanolamines, for example mono-, di - And triethanolamine and primary, secondary or tertiary C ⁇ _4 ⁇ alkylamines into consideration.
  • the neutralization bases are preferably used in the form of 20 to 50% by weight aqueous solutions, aqueous sodium hydroxide solutions being preferred.
  • the sulfonation products of the lauric alcohols are mixtures which essentially contain alkyl and alkenyl sulfates. Since when unsaturated fatty alcohols are used in the sulfonation, sulfur trioxide also accumulates on the double bond, the mixture also contains substances which can contain an internal sulfonate group or a sulfonate and a sulfate group. The proportion of these internal sulfonation products can usually be 10 to 25% by weight, based on the amount of anionic surfactant.
  • the sulfonation products can be bleached in a manner known per se by adding hydrogen peroxide and / or sodium hypochlorite solution. Based on the solids content in the solution of the sulfonation products, 0.2 to 2% by weight hydrogen peroxide, calculated as 100% substance, and / or corresponding amounts of sodium hypochlorite are used.
  • the pH of the solutions can be adjusted to 7.5 to 10 by adding alkali. To stabilize against bacterial contamination, a preservation is also recommended, e.g. B. with formaldehyde solution, p-hydroxybenzoate, sorbic acid or other known preservatives.
  • the light-colored alkenyl sulfate pastes obtainable by the process according to the invention have excellent detergent properties and a high solubility in cold water. They are therefore suitable for the production of powdered or liquid detergents, dishwashing detergents and cleaning products and products for hair and body care, in which they are used in amounts of 0.1 to 25, preferably 1 to 10% by weight, based on the solid ⁇ substance content of the agents - may be included.
  • Anionic surfactant content 65.4% by weight sulfate content 53.1% by weight sulfonate content 12.3% by weight
  • the anionic surfactant content and the unsulfonated contents were determined according to the DGF standard methods, Stuttgart, 1950-1984, H-III-10 and G-II-6b.
  • the sulfate content was calculated as sodium sulfate, the water content was determined by the Fischer method.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

On obtient des pâtes d'alkénylsulfate de couleur claire en faisant réagir des alcools lauriques renfermant a) des alcools gras insaturés de formule (I): R1-OH dans laquelle R1 désigne un reste hydrocarbure aliphatique linéaire insaturé de 16 à 22 atomes de carbone avec 1, 2 ou 3 doubles liaisons, et b) des alcools gras saturés de formule (II): R2-OH dans laquelle R2 désigne un reste hydrocarbure aliphatique saturé, linéaire ou ramifié, de 12 à 22 atomes de carbone, avec du trioxyde de soufre gazeux, puis en neutralisant et en hydrolysant par des bases aqueuses les produits acides issus de la réaction.
PCT/EP1992/002499 1991-11-08 1992-10-30 Procede de fabrication de pates d'alkenylsulfate de couleur claire WO1993009091A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP5508156A JPH07500829A (ja) 1991-11-08 1992-10-30 薄色アルケニルスルフェートペーストの製法
EP92922761A EP0613460A1 (fr) 1991-11-08 1992-10-30 Procede de fabrication de pates d'alkenylsulfate de couleur claire

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4136784.7 1991-11-08
DE19914136784 DE4136784A1 (de) 1991-11-08 1991-11-08 Verfahren zur herstellung hellfarbiger alkenylsulfat-pasten

Publications (1)

Publication Number Publication Date
WO1993009091A1 true WO1993009091A1 (fr) 1993-05-13

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ID=6444359

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/002499 WO1993009091A1 (fr) 1991-11-08 1992-10-30 Procede de fabrication de pates d'alkenylsulfate de couleur claire

Country Status (4)

Country Link
EP (1) EP0613460A1 (fr)
JP (1) JPH07500829A (fr)
DE (1) DE4136784A1 (fr)
WO (1) WO1993009091A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19939565A1 (de) * 1999-08-20 2001-02-22 Cognis Deutschland Gmbh Verzweigte, weitgehend ungesättigte Fettalkoholsulfate

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2214254A (en) * 1939-01-18 1940-09-10 Procter & Gamble Method for reacting higher alcohols with sulphating agents
US3763208A (en) * 1970-10-19 1973-10-02 Electric Reduction Co Ltd Use of amine compounds in the sulfation of alcohols
WO1992016606A1 (fr) * 1991-03-21 1992-10-01 Henkel Kommanditgesellschaft Auf Aktien Procede de preparation de pates tres concentrees en sulfate d'alccools gras

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2214254A (en) * 1939-01-18 1940-09-10 Procter & Gamble Method for reacting higher alcohols with sulphating agents
US3763208A (en) * 1970-10-19 1973-10-02 Electric Reduction Co Ltd Use of amine compounds in the sulfation of alcohols
WO1992016606A1 (fr) * 1991-03-21 1992-10-01 Henkel Kommanditgesellschaft Auf Aktien Procede de preparation de pates tres concentrees en sulfate d'alccools gras

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 75, no. 1, 5. Juli 1971, Columbus, Ohio, US; abstract no. 5154, D. NOVAK ET AL. 'Sulfating of unsaturated aliphatic alcohols by gaseous sulfur trioxide.' Seite 432 ;Spalte 1 ; *
CHEMICAL ABSTRACTS, vol. 88, no. 8, 20. Februar 1978, Columbus, Ohio, US; abstract no. 52288m, A.S. YUSUPOV ET AL. 'Sulfating of unsaturated aliphatic alcohols by gaseous sulfur trioxide.' Seite 84 ;Spalte 2 ; *
TENSIDE DETERGENTS Bd. 15, Nr. 6, 1978, Seiten 299 - 306 M. MORAK ET AL. 'Sulfatierung von unges{ttigten Fettalkoholen' in der Anmeldung erw{hnt *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19939565A1 (de) * 1999-08-20 2001-02-22 Cognis Deutschland Gmbh Verzweigte, weitgehend ungesättigte Fettalkoholsulfate

Also Published As

Publication number Publication date
JPH07500829A (ja) 1995-01-26
DE4136784A1 (de) 1993-05-13
EP0613460A1 (fr) 1994-09-07

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