[go: up one dir, main page]

WO1994001397A1 - Procede de fabrication de pates concentrees de sels d'acides gras alpha-sulfonique - Google Patents

Procede de fabrication de pates concentrees de sels d'acides gras alpha-sulfonique Download PDF

Info

Publication number
WO1994001397A1
WO1994001397A1 PCT/EP1993/001644 EP9301644W WO9401397A1 WO 1994001397 A1 WO1994001397 A1 WO 1994001397A1 EP 9301644 W EP9301644 W EP 9301644W WO 9401397 A1 WO9401397 A1 WO 9401397A1
Authority
WO
WIPO (PCT)
Prior art keywords
alpha
fatty acids
pastes
carbon atoms
formula
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.)
Ceased
Application number
PCT/EP1993/001644
Other languages
German (de)
English (en)
Inventor
Wolfgang Poly
Frank Wangemann
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of WO1994001397A1 publication Critical patent/WO1994001397A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • C11D1/28—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
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
    • C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
    • 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
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising

Definitions

  • the invention relates to a process for the production of concentrated pastes of alpha-sulfofatty acid salts, in which hardened fatty acids are sulfonated in the presence of small amounts of saturated triglycerides and then neutralized with aqueous bases.
  • Alpha-sulfofatty acid salts are addition products of sulfur trioxide with saturated fatty acids. Since the substances have a carboxylate and a sulfonate group, they are often referred to as "alpha-disalts".
  • Alpha-disalts are anionic surfactants that can be produced on the basis of low-refined animal or vegetable raw materials. Since they also have excellent detergent properties, they not only meet the market need for natural chemical raw materials, but are also particularly suitable for producing high-performance detergents, dishwashing detergents and cleaning agents.
  • Well ⁇ wood describes a process in which fatty acids are sulfonated with a SO3 / air mixture in a falling film reactor and free sulfur trioxide dissolved in the mixture is trapped immediately after sulfonation by adding alkylbenzene [DE- OS-22 13 155].
  • alkylbenzene [DE- OS-22 13 155]
  • the influence of unreacted sulfur trioxide on the sulfonate color is demonstrably low, so that this process also does not represent a breakthrough on the way to light-colored products; in addition, mixtures of alpha-disalts and alkylbenzenesulfonates are always obtained.
  • German patent DE 16 43 111 (Unilever), the same author proposes mixtures of short-chain and to sulfonate long-chain saturated fatty acids at very high temperatures from 95 to 150 ° C. and short reaction times from 10 seconds to 5 minutes with a 40 to 50 mol% excess of SO 3. With regard to good washing properties, however, alpha-disalts with short alkyl residues are less desirable. In addition, the use of sulfur trioxide in the abovementioned excess amounts is prohibited for economic and ecological reasons.
  • British Patent GB 1,338,935 discloses a process for producing light-colored alpha-disalts, in which the sulfonating agent is used in a deficit.
  • the advantages of a better color are more than compensated for by considerable reductions in the degree of sulfonation.
  • the object of the invention was therefore to provide an improved process for the production of concentrated alpha-di to develop salt pastes that are free from the disadvantages described.
  • the invention relates to a process for the preparation of concentrated pastes of alpha-sulfofatty acid salts, in which mixtures of
  • R 1 CO represents an acyl radical having 6 to 22 carbon atoms, and has an iodine number of 0 to 0.5 and
  • R ⁇ CO, R ⁇ CO and R ⁇ CO independently represent saturated acyl radicals having 6 to 22 carbon atoms, and also have an iodine number of 0 to 0.5. reacted with a sulfonating agent and then neutralized with aqueous bases.
  • the invention includes the finding that the alpha-disalts obtainable in this way have a degree of sulfonation of in some cases significantly more than 85% and that they meet the desired profile of requirements with colors below 50 Velcro. Since the saturated triglycerides are largely split into glycerol and fatty acids during the sulfonation, which in turn are accessible to sulfonation, the proportion of impurities in the reaction product is also negligibly low.
  • Typical examples of fatty acids (component a) which are suitable as starting materials for alpha-disalts are caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, pal itic acid, stearic acid, isostearic acid, arachic acid and behenic acid and their technical mixtures, such as those obtained by splitting natural fats and oils.
  • the technical fatty acids used are practically free of unsaturated components and in particular have iodine numbers of 0 to 0.5, in particular 0.1 to 0.2.
  • Preferred is the use of appropriately hardened Ci2 / 18 ⁇ ⁇ ° cos fatty or Ci6 / i8 "" Ta l ⁇ r ⁇ etts acids.
  • Triglycerides which can be used as component b) in the sense of the method according to the invention, are to be understood as tresters of glycerol with fatty acids, which can be of synthetic, but in particular natural, origin. Typical examples are hardened palm oil, palm kernel oil, beef tallow and in particular coconut oil. In principle, other hardened oils, such as olive oil, rapeseed oil or sunflower oil, are also suitable; due to their high proportion of unsaturated content, hardening to the required low iodine numbers is associated with greater problems.
  • Components a) and b) can be used in a weight ratio of 95: 5 to 85:15, preferably 90:10.
  • the sulfation of the mixtures of fatty acids and triglycerides can be carried out with gaseous sulfur trioxide or chlorosulfonic acid in the manner known for fatty acid lower alkyl esters [J. Falbe (ed.), "Surfactants in consumer product", Springer Verlag, Berlin-Heidelberg, 1987, p. 61] , with reactors working according to the falling film principle being preferred.
  • the sulfur trioxide is diluted with an inert gas, preferably air or nitrogen, and in the form of a gas mixture which contains the sulfonating agent in a concentration of 1 to 8, in particular 2 to 5,% by volume.
  • the mixture of components a) and b) and the sulfating agent in a molar ratio of 1: 1.05 up to 1: 1.5, preferably 1: 1.1 to 1: 1.2. It is also advisable to carry out the sulfonation at temperatures of 50 to 98, preferably 80 to 90 ° C.
  • the acidic sulfonation products obtained during the sulfonation are stirred into aqueous bases and neutralized.
  • 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 25 to 55% by weight aqueous solutions.
  • the neutralization is carried out with aqueous bases of a concentration such that pastes of alpha-sulfofatty acid salts with a solids content of 35 to 50% by weight result.
  • the sulfonation products can be bleached in a manner known per se by adding hydrogen peroxide or sodium hypochlorite solution.
  • hydrogen peroxide or sodium hypochlorite solution Based on the solids content of the alpha-disalting pastes, 0.2 to 2% by weight of hydrogen peroxide, calculated as a 100% substance, or corresponding amounts of sodium hypochlorite are used.
  • the pH of the pastes can be adjusted using suitable buffering agents, e.g. B. be kept constant with sodium phosphate or citric acid. To stabilize against bacterial attack, preservation is also recommended, e.g. B. with formaldehyde solution, p-hydroxybenzoate, sorbic acid or other known preservatives.
  • the alpha-sulfofatty acid salts obtainable by the process according to the invention are highly concentrated, light-colored and have a high degree of sulfonation. They are suitable for the production of detergents, dishwashing detergents and cleaning agents, and products for hair and body care, in which they are present in amounts of 1 to 50, preferably 5 to 30,% by weight, based on the composition - May be included.
  • Tab. 1 Sulfonation of tallow fatty acid, percentages as% by weight
  • IZ (FS) iodine number of the fatty acid used
  • K ⁇ coconut oil concentration
  • P paste concentration (solids content)
  • WAS - active detergent substance anionic surfactant content based on paste
  • the anionic surfactant content was determined according to the DGF standard methods, Stuttgart 1950-1984, H-III-10.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

On fabrique des pâtes de sels d'acides gras alpha-sulfoniques, d'une teneur en matière solide de 35 à 50 % en faisant réagir des mélanges composés (a) d'acides gras répondant à la formule (I): R1COOH dans laquelle R1CO désigne un reste alkyle ayant 6 à 22 atomes de carbone, et présentant un indice d'iode de 0 à 0,5, et (b) de triglycérides répondant à la formule (II), dans laquelle R?2CO, R3CO et R4¿CO désignent, indépendamment l'un de l'autre, un reste acyle saturé ayant 6 à 22 atomes de carbone et présentant également un indice d'iode de 0 à 0,5, avec un agent de sulfonation, puis en neutralisant au moyen de bases concentrées aqueuses.
PCT/EP1993/001644 1992-07-06 1993-06-28 Procede de fabrication de pates concentrees de sels d'acides gras alpha-sulfonique Ceased WO1994001397A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19924222169 DE4222169A1 (de) 1992-07-06 1992-07-06 Verfahren zur Herstellung konzentrierter Pasten von alpha-Sulfofettsäuresalzen
DEP4222169.2 1992-07-06

Publications (1)

Publication Number Publication Date
WO1994001397A1 true WO1994001397A1 (fr) 1994-01-20

Family

ID=6462593

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/001644 Ceased WO1994001397A1 (fr) 1992-07-06 1993-06-28 Procede de fabrication de pates concentrees de sels d'acides gras alpha-sulfonique

Country Status (2)

Country Link
DE (1) DE4222169A1 (fr)
WO (1) WO1994001397A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2195186A (en) * 1937-02-06 1940-03-26 Solvay Process Co Process for the production of sulphonated fatty acids
GB1214714A (en) * 1968-04-29 1970-12-02 Procter & Gamble Ltd Process for preparing monosodium alpha-sulphocarboxylic acids
DE1643111A1 (de) * 1966-05-02 1971-02-25 Unilever Nv Verfahren zur Herstellung von alpha-Sulfofettsaeuren
WO1991001972A1 (fr) * 1989-08-09 1991-02-21 Henkel Kommanditgesellschaft Auf Aktien Procede pour fabriquer des sulphonates d'acide oleique de couleur claire
DE4035935A1 (de) * 1990-11-12 1992-05-14 Henkel Kgaa Verfahren zur herstellung konzentrierter waessriger dispersionen von alpha-sulfofettsaeure-mono- und/oder -disalz

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2195186A (en) * 1937-02-06 1940-03-26 Solvay Process Co Process for the production of sulphonated fatty acids
DE1643111A1 (de) * 1966-05-02 1971-02-25 Unilever Nv Verfahren zur Herstellung von alpha-Sulfofettsaeuren
GB1214714A (en) * 1968-04-29 1970-12-02 Procter & Gamble Ltd Process for preparing monosodium alpha-sulphocarboxylic acids
WO1991001972A1 (fr) * 1989-08-09 1991-02-21 Henkel Kommanditgesellschaft Auf Aktien Procede pour fabriquer des sulphonates d'acide oleique de couleur claire
DE4035935A1 (de) * 1990-11-12 1992-05-14 Henkel Kgaa Verfahren zur herstellung konzentrierter waessriger dispersionen von alpha-sulfofettsaeure-mono- und/oder -disalz

Also Published As

Publication number Publication date
DE4222169A1 (de) 1994-01-13

Similar Documents

Publication Publication Date Title
DE4038477A1 (de) Verfahren zur kontinuierlichen herstellung von partialglyceridsulfaten
DE2355402B2 (de) Verfahren zur Herstellung einer polyfunktionellen, stabilen, flüssigen Detergentien-Mischung
WO1992008695A1 (fr) PROCEDE POUR LA FABRICATION DE DISPERSIONS AQUEUSES CONCENTREES DE MONO- ET/OU DISEL D'α-ACIDE GRAS SULFONIQUE
DE4220580A1 (de) alpha-Sulfocarbonylverbindungen
DE3936001A1 (de) Verfahren zur sulfierung ungesaettigter fettsaeureglycerinester
DE3941365A1 (de) Verfahren zur herstellung von salzen sulfierter fettsaeureglycerinester
DE2455891A1 (de) Verfahren zur herstellung von alphasulfofettsaeureestersalzen
WO1993012215A1 (fr) Procede de fabrication de triglycerides hydrophilises
DE3828892A1 (de) Oelsaeure-niedrigalkylestersulfonate, verfahren zu ihrer herstellung und ihre verwendung
WO1994001397A1 (fr) Procede de fabrication de pates concentrees de sels d'acides gras alpha-sulfonique
DE4432367B4 (de) Verwendung von Partialglyceriden in einem Verfahren zur Herstellung von hellfarbigen Fettsäuremonoglyceridsulfaten
WO1993010084A1 (fr) Procede de fabrication d'alcanolamides d'acides gras sulfates
DE4032910A1 (de) Verfahren zur herstellung von alkylsulfatpasten mit verbesserten fliesseigenschaften
WO1991016300A1 (fr) Procede de fabrication de sels d'alkylesters inferieurs d'acides gras alpha-sulfones detergents de teinte claire
WO1991013896A1 (fr) Procede de sulfonation de melanges contenant des glucosides d'alkyle
DE4136784A1 (de) Verfahren zur herstellung hellfarbiger alkenylsulfat-pasten
DE821208C (de) Emulgator für Öle, Fette und ähnliche Produkte
DE4110179A1 (de) Verfahren zur kontinuierlichen herstellung von waessrigen loesungen anionischer tenside
DE628064C (de) Verfahren zur Herstellung von Sulfonierungsprodukten
DE1443992C (de) Verfahren zur Sulfonierung von Fett saureestern mehrwertiger Alkohole
DE4341795A1 (de) Verfahren zur Herstellung wasserfreier alpha-Sulfofettsäuresalze
DE1812708C3 (de) Verfahren zur Herstellung eines toluolsulfonsäurehaltigen Gemisches und die danach hergestellten Sulfonsäuregemische als solche
DE4300935A1 (de) Sulfonierte Diester
DE4236502A1 (de) Verfahren zur Herstellung von seifenhaltigen Fettsäureisethionaten
DE1225798B (de) Schuett- und rieselfaehige, insbesondere pulverfoermige Wasch-, Netz- und Emulgiermittel

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase