US3251868A - Sulfonation of saturated fatty acid esters of polyvalent alcohols - Google Patents

Sulfonation of saturated fatty acid esters of polyvalent alcohols Download PDF

Info

Publication number
US3251868A
US3251868A US194839A US19483962A US3251868A US 3251868 A US3251868 A US 3251868A US 194839 A US194839 A US 194839A US 19483962 A US19483962 A US 19483962A US 3251868 A US3251868 A US 3251868A
Authority
US
United States
Prior art keywords
sulfonation
fatty acid
sulfur
trioxide
mol
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 - Lifetime
Application number
US194839A
Other languages
English (en)
Inventor
Stein Werner
Weiss Herbert
Koch Otto
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
Application granted granted Critical
Publication of US3251868A publication Critical patent/US3251868A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

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
    • 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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom

Definitions

  • This invention relates to new and useful improvements in the sulfonation of fatty acid esters of polyvalent alcohols.
  • the invention more particularly relates to an improved procedure for allowing a trouble-free sulfonation of esters of fatty acids and polyvalent alcohols, particularly fatty acid triglycerides into the corresponding alpha sulfonic acids using gaseous sulfur trioxide.
  • One object of this invention is the sulfonation of fatty acid esters of polyvalent alcohols, such as fatty acid triglycen'des, using an excess of gaseous sulfur trioxide as the sulfonation agent, without the above-mentioned difficulties.
  • FIG. 1 diagrammatically shows an embodiment of a reaction vessel for effecting the sulfonation in accordance with the invention
  • FIG. 2 diagrammatically shows a further embodiment of an apparatus for effecting the sulfonation in accordance with the invention. 7
  • triglycerides As the starting material for carrying out of the process inaccordance with the invention, it is preferable to use natural triglycerides though synthetic triglycerides or synthetic esters of fatty acids with other polyvalent alcohols, such as for example glycols, pentaerythrite, mannite, sorbite, or the like may be used.
  • synthetic triglycerides or synthetic esters of fatty acids with other polyvalent alcohols such as for example glycols, pentaerythrite, mannite, sorbite, or the like may be used.
  • the fatty acid radicals present in both the fatty acid esters of polyvalent alcohols andfatty acids, fatty acid esters of monovalent alcohols or fatty acid nitriles, to be admixed therewith for the sulfonation in accordance with the invention may be of any origin and should contain 628 and preferably 8-18 carbon atoms.
  • These fatty acid ice radicals may, for example, some from the natural fats of plants, .land-or-Water-animals. Through selection of the starting fats, it is possible to extensively influence the properties of the sulfonates to be produced.
  • fats which preferably contain fatty acids with 10-14 carbon atoms per fatty acid radical particularly from the fats of the lauricacid group, which are rich in fatty acid with 12 carbon atoms
  • products which are readily soluble at lower temperatures of, for example 20-'45 C. are obtained.
  • From other fats, which preferably contain fatty acids with l6-l8 and more carbon atoms per fatty acid radical for example from other plant fats than the above named, from tallow or from the Whaleand dish-oils, there are obtained products which are particularly useful at temperatures within the range of 50'100 C.
  • the materials present in the mixture sulfonated in accordance with the invention should not contain further sulfatizable or sulfonatable groups, apart from alpha-position hydrogen atoms, such as for example double bonds or alcoholic hydroxyl groups.
  • the fatty acids, or their derivatives, i.e. the nitriles or esters with monovalent alcohols may be any such material having fatty acid radicals as specified above.
  • these alcohols may be of primary and secondary nature and contain 1-20 carbons atoms in the molecule.
  • the esters of fatty acids with methylto nonyl-alcohols are applicable though it is also possible to use the fatty acid esters which contain radicals of still higher alcohols in the molecule as may be produced for example through reduction from the initially mentioned fatty acids or fatty acid mixtures or in other ways synthetically.
  • Examples of easily accessible esters of fatty acids with higher fat-alcohols include the hydrogenation products of the oleylolate occurring in the sperm oil or the naturally occurring or synthetically produced wax-esters.
  • distillates are preferably used as the starting material, which is also advisable in connection with the fatty acid derivatives sofar as these are distillable under the technical prerequisites in each case.
  • the starting materials are not initially purified by distillation, on account of a high boiling point or for other reasons may be distilled, as for example in triglycerides, then it is advisable to initially remove the impurities present in the starting material to be sulfonated by other conventional methods.
  • albuminous substances and slimy substances are separated by the deacidification and refining of the oils in a manner known per se.
  • esters of primary or secondary alcohols containing 1-5 carbon atoms, have proved particularly suitable.
  • the fatty acids or other fatty acid derivatives, to be sulfonated in mixture with fatty acid esters of polyvalent alcohols may have a chain-length-distribution of the fatty acid radicals which deviates from that of the esters of polyvalent alcohols, ,or which corresponds with it.
  • the sulfonation may be carried out continuously or discontinuously, by bringing together the sulfur-trioxide, diluted with an inert gas, with the starting material to be sulfonated.
  • inert gases for example, air, nitrogen,
  • the sulfur-trioxide content should amount to 2-40 volume percent, preferably 3-20 volume percent of the gas mixture.
  • the sulfonation agent quantities to be used per mol of fatty acid radical lie within the range of 1.1-1.8, preferably of 1.2-1.6 mol sulfur-trioxide, wherein with increasing length of the fatty acid-and alcohol-radical, greater sulfonation agent quantities are needed in order to attain high degrees of sulfonation.
  • the reaction sets in with practically serviceable velocities at about 30 C. and is appropriately carried out at gradually rising temperature. degrees of sulfonation, temperatures of 70-100 C., preferably of 75-95' C. and particularly of 80-90 C., are necessary. Since the quantity of the colored by-products, formed in the sulfonation, increases with rising temperature, it is advisable to hold the reaction mixture for as short a time as possible at the end temperature.
  • reaction zones may have the form of reaction vessels connected behind one another, in which an inert gas stream, containing sulfurtrioxide, is introduced into .the reaction mixture and from which the sulfur-trioxide-free and/or sulfur-trioxide-poor inert gas stream is drawn off.
  • the temperature is gradually raised so that the sulfonation proceeds with technically serviceable speed, but not tocompletion, as for example to up to 70 and preferably up to 65 C. If there is obtained at these temperatures, up to 70C., a degree of sulfonation of at least 50% and preferably of 60-80%, then the sulfonation is completed by raising the temperature to at most 100 C. and preferably 75-95 and most preferably -90 C.
  • hydroxy hydrocarbon compounds contain as hydrophobic radical a hydrocarbon radical with 10-28 and preferably 12-18 carbon atoms, wherein in the case of alkyl-aromatic or cyclo-alkyl-aromatic radicals at least 8 of these carbon atoms must be of aliphatic or cyclo-aliphat-ic nature.
  • hydroxy hydrocarbon compounds examples include fat-alcohols or fatty acid alkylol amides or water-insoluble or water-soluble partial ethers or partial esters of fat alcohols, alkyl-phenols or fatty acids with polyvalent alcohols, wherein the partial ethers may be, in. the form of the addition products of ethylene oxide and/or propylene oxide to fat alcohols, alkyl phenols, acyl-phenols, fatty-acid amides or fatty acid alkylol amides or fatty acids.
  • the hydrogen peroxide is charged preferably as 20-75 weight percent and most preferably as 30-50 weight percent-product. Furthermore, it is advisable, to thus choose the concentration of the hydrogen peroxide to be used in dependence on its quantity so that the sulfuric acid forming at the start of the bleaching process from free sulfur-trioxide and the Water quantity introduced with the hydrogen-peroxide, is not more diluted than a 20% sulfuric-acid, Preferably this sulfuric acid is to represent, mathematically considered, a mixture of sulfur-trioxide and water with a sulfur-trioxide-con-tent up to 95 weight percent and preferably up to -95 weight percent.
  • the bleaching occurs at temperatures within the range of 20-100 and preferably of 40-80 C.
  • the bleaching of the sulfonation products may take place immediately subsequent to the sulfonation, or subsequent to the conversion of the excess sulfur-trioxide with hydroxy hydrocarbon compounds where provided. However, if the excess sulfonation agent is. converted after the bleaching with added hydroxy hydrocarbon compounds, then it is advisable to adjust quantity and concentration of the hydrogen peroxide in dependence on the sulfur-trioxide-content of the reaction product so that the mixture of 'sulfur-trioxide and water, present in the reaction product (mathematically considered), corresponds at least to a 98% sulfuric acid. One may keep the water content so low that this mixture, mathematically considered, consists up to 95 weight percent and preferably of 80-90 weight percent of sulfur-trioxide.
  • a conversion of the excess sulfonation agent with the added hydroxy hydrocarbon compound, carried out after the bleaching, is above all most technically interesting, in the processing of sulfonation products containing fatty acids which are to be esterified with the added hydroxyl compound, or if one simultaneously Wishes to re-esterify the sulfonated fatty acid esters.
  • the neutralization of the instant mixture of sulfonate and sulfuric acid ester with inorganic or organic bases takes place in the customary manner. If starting materials containing fatty acids have been sulfonated, then the preferably bleached sulfonic acids may be so neutralized that the sulfo-fatty-acids are present as mono-salts, which then are esterified in a manner known per se with added hydroxyl-compounds.
  • the triglycerides processed have been treated for the removal of slime and subjected to deacidification and hardening.
  • the iodine number of the hardened tallow amounts to 0, that of the hardened coconut oil amounts to 1.
  • the fatty acid esters processed are practically saturated (iodine number not greater than 0.2) and have been purified through distillation.
  • the anal-indications refer to the fatty acid radicals.
  • the sulfonation products obtained at the end of the sulfonation were still well fluid and no difiiculties whatsoever were encountered.
  • the viscosity of the reaction mixture rapidly increases and great quantities of a very stable foam form. Also a uniform working-in of the hydrogen peroxide into the sulfonation product cooled to temperatures below 50 C. is very difiicult.
  • Example 1 Into a mixture of 61 g. hardened coconut-oil (0.25 mol) and 63 g. of the ethylester of a hardened palmkernel-fatty-acid (0.25 mol) 52 g. sulfur-trioxide gas (0.65 mol), diluted with 20-fold volume-quantity of air, was introduced in the course of 60 minutes at 80 C. After the introduction, the mixture. still remained standing for about 15 minutes at 89 C. The crude acid sulfonation product was bleached with 3% of its weight of H (as 40% aqueous solution) for 30 minutes at 60 C., and then neutralized with 5%-soda-lye.
  • the degree of sulfonation of the, product was 96.4%. 5%-solution of the sulfonate, with reference to crude acid sulfonation product, showed in the Lovibond-Tintometer in a 4" cell, the, following color values:
  • Example 2 A mixture of 72 g. hydrogenated tallow (melting point 57.5 C; 0.25 mol) and 62 g. of the ethylester of a hydrogenated palm-kernel-fatty acid (0.25 mol), mentioned in Example 1, was, as described in Example 1, sulfonated, bleached and neutralized. The degree of sulfonation of the product amounted to 98.5%; the Lovibond color values were:
  • Example 3 A mixture of 83 g. hardened coconut-oil (0.375 mol) and 31 g. ethylester of a hardened palm-kernel-fattyacid (0.125 mol) was, as described in Example 1, sulfonated, bleached, and neutralized. The degree of sulg donation of the product amounted to 79.1%; the color values measured in the Lovibond-Tintometer in a 4" cell were:
  • Example 4 A mixture of 63 g. of the ethylester of a hardened palm-kernel-fatty-acid (0.25 mol), 37 g. of the ethylester-of a hardened tallow fatty-acid (0.125 mol) and 28 g. of a hardened coconut-oil (0.125 mol) was, as described in Example 1, sulfonated, bleached and neutralized. The degree of sulfonation of the product amounted to 96.1% the color values measuredin the Lovibond- Tintometer in a 4" cell were:
  • Example 5 I A mixture of 60 g. of the methyl-ester of a hardened palm-kernel-fatty-acid (0.25 mol), 36 g. of the methylester of a hardened tallow-fatty-acid (0.125 mol) and 28 g. hardened coconut-oil (0.125 mol) was, as described in Example 1, sulfonated, bleached and neutralized. The degree of sulfonation of the product amounted to 97.4% the color values measured in the Lovibond-Tintometer in a 4" cell were:
  • Example 6 For the carrying-out of the test here described, 5 of the vessels 13 shown in the drawing, were connected one after the other, in series.
  • the starting m-ateriahto be sulfonated is designated 3 and the lines 14 and 15 provided with the valves 16 and 17, are for the introduction of the starting material to be sulfonated and the sulfurtrioxide-air mixture.
  • 19 is an outlet for air, substantially free from sulfur-trioxide, and 18 an outlet for the reaction mixture.
  • the lower part of the reaction vessel is surrounded by the heat jacket 6 with the heat exchange inlet 7 and outlet 8.
  • the first four reaction vessels were filled with ester and the heating adjusted so that the reaction mixture in the vessels had during the entire test the following temperatures, rising from vessel to vessel: 1st vessel, 50; second vessel, 60, 3rd vessel 70 ,4th vessel, 80, 5th vessel C.
  • Sulfur-trioxide diluted with a 20- fold volume quantity of air, was blown into the first four vessels in such quantities that in the individual vessels, the following sulfur-trioxide-quantities- (indicated in percent of the stoichiometrically necessary quantity for a quantitative sulfonation) were taken up 1St-'52, 2nd 78, 3rd104, 4thl30%. No sulfur trioxide was blown into the last vessel.
  • Example 7 The sulfonation was effected in an apparatus according to FIG. 2.
  • This device consists of an absorption vessel 7 20 and the heat exchange device 40, which are connected with one another through the line 30.
  • the absorptionvessel 20 consists of an interior vessel 21, which is surrounded by a heating jacket 22 with feed-line 23 and discharge-line 24 for the heat exchange liquid.
  • the starting material is introduced through the nozzle 27, while the sulfur-trioxide-inert gas-mixture is conducted through the line 25 under the surface of the starting material in the vessel 21.
  • the inert-gas, practically free from sulfur trioxide, passes out at 26; the temperature is indicated'on the thermometer 28, which also may be developed as thermo-regulating device, such as a thermostat which controls the flow of the heat exchange liquid.
  • the starting material containing sulfur-trioxide
  • the line 30 is bent upward in a U-shape and thus fulfills the function of a level-regulator.
  • the deaerating-device 33 is mounted, while at the lowest point, shortly before the heat exchange device, is the discharge faucet 34.
  • fatty-acid-r-adicals Into about 1 mol (referred to fatty-acid-r-adicals) of this mixture, in the interior vessel 21 of the absorption-device 20, were blown-in in the course of about 2 hours at 30 C., 1.3 mol sulfur-trioxide, diluted with a 20-fold air quantity. After this quantity was dissolved, the sulfonation was continued as a continuous operation by adding per hour so much ester that the median time of stay of the ester in the absorption vessel amounted to 2 hours. The sulfur-trioxide was added continuously in a quantity of 1.3 mol per mol of fed fattyacid-radicals. The three heat exchange coils, connected behind the absorption vessel, were held at temperatures of 60, 80 andp90 C. The time of stay in each coil amounted to about 20 minutes. The material had, upon passing out of the first reaction coil, a degree of sulfonation of about 65-70%.
  • the product passing out of the last reaction coil was cooled, then bleached with 2% of its weight of H (used as 40%-aqueous-solution) for 2 hours at 50-60 C., and neutralized with l0%-soda-lye.
  • the degree of sulfonation of the product amounted to 94-95%.
  • the Lovibond color values of the bleached product measured as a- %-solution of the sulfonate, with reference to crude acid sulfonation product, in a 4" cell, were:
  • the improvement which comprises effecting the sulfonation with the ester in admixture with about 20 to 85% by weight of an ester of a fatty acid having from 6-28 carbon atoms with a monovalent alcohol.
  • triglycerides containing a substantially saturated unsubstituted fatty acid radicalhaving from 6-28 carbon atoms in which the triglyceride is reacted with an excess of a gaseous S0 the improvement which comprises effecting the sulfonation with the triglyceride in admixture with about 20 to' by weight of an ester of a fatty acid having from 6-28 carbon atoms with a monovalent alcohol.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (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)
  • Detergent Compositions (AREA)
  • Fats And Perfumes (AREA)
US194839A 1961-08-08 1962-05-15 Sulfonation of saturated fatty acid esters of polyvalent alcohols Expired - Lifetime US3251868A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEH43356A DE1186051B (de) 1961-08-08 1961-08-08 Verfahren zur Herstellung von Sulfonierungserzeugnissen

Publications (1)

Publication Number Publication Date
US3251868A true US3251868A (en) 1966-05-17

Family

ID=7155163

Family Applications (1)

Application Number Title Priority Date Filing Date
US194839A Expired - Lifetime US3251868A (en) 1961-08-08 1962-05-15 Sulfonation of saturated fatty acid esters of polyvalent alcohols

Country Status (6)

Country Link
US (1) US3251868A (de)
AT (1) AT239261B (de)
CH (1) CH439263A (de)
DE (1) DE1186051B (de)
DK (1) DK117141B (de)
GB (1) GB1001284A (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3971815A (en) * 1974-11-13 1976-07-27 The Procter & Gamble Company Acid mix process
US4623695A (en) 1984-01-25 1986-11-18 Henkel Kommanditgesellschaft Auf Aktien Acrylate hydrosols
US4820451A (en) * 1985-11-02 1989-04-11 Henkel Kommanditgesellschaft Auf Aktien Process for the production of mobile pastes of washing-active α-sulfofatty acid ester salts of high solids content
US5382677A (en) * 1990-05-30 1995-01-17 Henkel Kommanditgesellschaft Auf Aktien Process for the production of highly concentrated pastes of α-sulfofatty acid alkyl ester alkali metal salts
US5384422A (en) * 1990-05-30 1995-01-24 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored α-sulfofatty acid alkyl ester alkali metal salt pastes
US5391783A (en) * 1990-05-30 1995-02-21 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored pastes of α-sulfofatty acid alkyl ester alkali metal salts
US5391782A (en) * 1990-05-30 1995-02-21 Henkel Kommanditgesellschaft Auf Aktien Process for the production of highly concentrated pastes of α-sulfofatty acid alkyl ester alkali metal salts
US5429773A (en) * 1993-02-05 1995-07-04 The Procter & Gamble Company Process to improve alkyl ester sulfonate surfactant compositions
US5587500A (en) * 1993-09-17 1996-12-24 The Chemithon Corporation Sulfonation of fatty acid esters

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS522890B2 (de) * 1973-11-29 1977-01-25
JPS5143716A (en) * 1974-10-08 1976-04-14 Lion Fat Oil Co Ltd Arufua suruhoshibosanesuteruenno seizoho

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB288126A (en) * 1927-04-01 1929-04-22 Oranienburger Chem Fab Ag New or improved method for the production and use of stable sulpho-acids of high molecular weight and their salts
US1926442A (en) * 1927-06-07 1933-09-12 Ig Farbenindustrie Ag Production of sulfonic acids of aliphatic and hydroaromatic carboxylic acids
DE617347C (de) * 1927-01-25 1935-08-26 Farb Und Gerbstoffwerke Carl F Verfahren zur Darstellung sulfonierter Fette und OEle mit hohem Gehalt an organisch gebundener Schwefelsaeure
US2691040A (en) * 1951-03-29 1954-10-05 Universal Oil Prod Co Sulfonation of organic compounds with sulfur trioxide
US2878271A (en) * 1957-05-17 1959-03-17 Tennesse Corp Neutralization of sulfonation mixtures and products thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE582790C (de) * 1927-01-14 1933-08-23 Oranienburger Chem Fab Akt Ges Verfahren zur Herstellung von Reinigungs-, Emulgierungs- und Benetzungsmitteln

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE617347C (de) * 1927-01-25 1935-08-26 Farb Und Gerbstoffwerke Carl F Verfahren zur Darstellung sulfonierter Fette und OEle mit hohem Gehalt an organisch gebundener Schwefelsaeure
GB288126A (en) * 1927-04-01 1929-04-22 Oranienburger Chem Fab Ag New or improved method for the production and use of stable sulpho-acids of high molecular weight and their salts
US1926442A (en) * 1927-06-07 1933-09-12 Ig Farbenindustrie Ag Production of sulfonic acids of aliphatic and hydroaromatic carboxylic acids
US2691040A (en) * 1951-03-29 1954-10-05 Universal Oil Prod Co Sulfonation of organic compounds with sulfur trioxide
US2878271A (en) * 1957-05-17 1959-03-17 Tennesse Corp Neutralization of sulfonation mixtures and products thereof

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3971815A (en) * 1974-11-13 1976-07-27 The Procter & Gamble Company Acid mix process
US4623695A (en) 1984-01-25 1986-11-18 Henkel Kommanditgesellschaft Auf Aktien Acrylate hydrosols
US4820451A (en) * 1985-11-02 1989-04-11 Henkel Kommanditgesellschaft Auf Aktien Process for the production of mobile pastes of washing-active α-sulfofatty acid ester salts of high solids content
US5382677A (en) * 1990-05-30 1995-01-17 Henkel Kommanditgesellschaft Auf Aktien Process for the production of highly concentrated pastes of α-sulfofatty acid alkyl ester alkali metal salts
US5384422A (en) * 1990-05-30 1995-01-24 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored α-sulfofatty acid alkyl ester alkali metal salt pastes
US5391783A (en) * 1990-05-30 1995-02-21 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored pastes of α-sulfofatty acid alkyl ester alkali metal salts
US5391782A (en) * 1990-05-30 1995-02-21 Henkel Kommanditgesellschaft Auf Aktien Process for the production of highly concentrated pastes of α-sulfofatty acid alkyl ester alkali metal salts
US5429773A (en) * 1993-02-05 1995-07-04 The Procter & Gamble Company Process to improve alkyl ester sulfonate surfactant compositions
US5587500A (en) * 1993-09-17 1996-12-24 The Chemithon Corporation Sulfonation of fatty acid esters

Also Published As

Publication number Publication date
DK117141B (da) 1970-03-23
CH439263A (de) 1967-07-15
AT239261B (de) 1965-03-25
GB1001284A (en) 1965-08-11
DE1186051B (de) 1965-01-28

Similar Documents

Publication Publication Date Title
US2383632A (en) Process of treating fatty glycerides
US3372188A (en) Sulfoxidation process in the presence of sulfur trioxide
US3251868A (en) Sulfonation of saturated fatty acid esters of polyvalent alcohols
US5294726A (en) Process for the preparation of light-colored oleic acid sulfonates
US4164505A (en) Flow process for conjugating unconjugated unsaturation of fatty acids
GB2089793A (en) A process for the simplified production of light-coloured washing-active a-sulfofatty acid esters
US2383633A (en) Process for treating fatty glycerides
US3544613A (en) Alcohol sulfation
US3256303A (en) Sulfonation of fatty acids and their esters
US2383596A (en) Method of treating fatty glycerides
US2383602A (en) Process for treatment of fatty glycerides
US3159657A (en) Preparation of light-colored sulfonated fatty acids and fatty acid derivatives
US2065540A (en) Production of oxygenated organic compounds from unsaturated hydrocarbons
US2383599A (en) Treating fatty glycerides
US3158632A (en) Alpha-sulfonation of saturated fatty acids and their derivatives
US3531518A (en) Process for the reaction of alpha-olefins and gaseous sulfur trioxide
US1944887A (en) Esters and method of preparing same
US2474740A (en) Process of preparing partial esters of glycerine and fatty acids
US2458170A (en) Continuous fat splitting
US3240794A (en) Brominating higher fatty acids and esters
US2655522A (en) Process of producing monoesters of polyhydric alcohol
US1823815A (en) Production of esters of sulphonic acids
US2529539A (en) Sulfonation of unsaturated esters
US2967872A (en) Process for making acyl taurides
US2979521A (en) Preparation of glycerol sulfuric acids