US3256303A - Sulfonation of fatty acids and their esters - Google Patents

Sulfonation of fatty acids and their esters Download PDF

Info

Publication number
US3256303A
US3256303A US194840A US19484062A US3256303A US 3256303 A US3256303 A US 3256303A US 194840 A US194840 A US 194840A US 19484062 A US19484062 A US 19484062A US 3256303 A US3256303 A US 3256303A
Authority
US
United States
Prior art keywords
sulfonation
sulfur trioxide
reaction
fatty acid
vessel
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
US194840A
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 US3256303A publication Critical patent/US3256303A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • 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
    • 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

Definitions

  • This invention relates to new and useful improvements in the sulfonation of fatty acids and their derivatives.
  • the invention more particularly relates to an improved process for sulfonating fatty acids or ltheir derivatives, such as their esters or nitriles, using an excess of sulfur trioxides gas as the sulfonation agent.
  • sulfonates of fatty acids and of fatty -acid derivatives, su-ch as esters or nitriles constitute commercially valuable materials due to Vtheir surface-active characteristics and resistance to hard water which render the same suitable as detergents and wetting agents.
  • These sulfonates are conventionally produced by the sulfonation of the corresponding fatty acids or fatty acid derivatives. When sulfonating these materials using an excess of gaseous sulfur trioxide, the reaction products produced were dark colored, brown-black products which, due to this discoloration, were unsuitable for commercial use.
  • One object of this invention is the obtaining of lighten colored reaction products, after the extensive sulfona-tion of fatty acids or their derivatives, using gaseous sulfur trioxide, as the sulfonation agent.
  • FIG. 1 diagrammatically shows an embodiment of an apparatus for effecting the sulfonation in accordance with sulfonated to lighter colored reaction products using -anv excess of gaesous S03 as the sulfonation agent if the sulfonation is initially effected at a temperature not exceeding 70 C. and using not more than about 65-90% of the total S03 quantity and, if, thereafter the sulfonation is continued preferably in a further sulfonation step or steps at a temperature above 70 C. using the remainder of the sulfur trioxide.
  • the sulfonation is initially effected in a first sulfonation step at a temperature between 30 and 70 and preferably 40-65 C., using not more than 65*90% of a l.l to 1.8 and preferably 1.2 to 1,6 molar quantity of S03 based on the fatty acid radicals to be sulfonated .and thereafter the sulfonation is concluded in one or more additional separate sulfonation steps at a ICC temperature between about and 95 C. and preferably -90" C., using the balance of said molar quantity. If more than two sulfonation steps are used, the temperature is preferably progressively increased within the range indicated from step to step.
  • the starting materials processed, in accordance with the invention are fatty acids or their derivatives, such as esters or nitriles which may be of any origin ⁇ and contain fatty acid radicals with y6-28, and preferably 8-18 carbon atoms. These fatty acid radicals may come from the natural fats of plants, landor water-animals. Through selection of the starting fats it is possible to extensively influence the properties of lthe sulfonates to be produced.
  • the starting materials should not contain apart from the alpha-position hydrogen atom, other sulfatizable or sulfonatable groups, such as forexample double-bonds or alcoholic hydroxyl-groups.
  • the fatty acid esters to be processed in accordance with the invention may be derived from monoor polyvalent alcohols, particularly from monoto trivalent-alcohols, and, as mentioned above, must not contain lany alcoholic hydroxyl groups or other sulfatizable or sulfonatable groups.
  • the radical may con-tain- 1-20 carbon atoms in the molecule.
  • the esters of fatty acids with methyl to nonyl-alcohols may be used.
  • fatty acid esters which contain radicals of such still higher alcohols'in the molecule as for example are produced by reduction of the initially mentioned fatty acids or fatty acid mixtures, or synthetically in some other manner.
  • Examples of readily available esters of fatty acids with higher fat alcohols include the hydrogenation products of the oleyloleate occurring in the sperm oil or the naturally occurring or synthetically produced wax esters.
  • fats particularly those of natural origin, and the fatty acids and their derivatives produced therefrom often contain accompanying substances, which, upon sulfonation produce strongly colored decomposition products. Although it is also possible to bleach these decomposition products according to a process mentioned hereinafter, it is advisable not to burden the sulfonation and the bleaching process through the decomposition products of such accompanying substances, which may be forthwith removed from .the fats and/ or the therefrom produced fatty ⁇ acids or their derivatives before the sulfonation.
  • Examples ofV products which give with the sulfonation agent strongly colored impurities include unsaturated fatty acids or fatty acid derivatives. Therefore, the fats to be processed are to be, as far as possible, extensively saturated, i.e., they are to have iodine numbers below 5, preferably below 2.
  • the starting fatty acids to be sulfonated are preferably in the form of distillates as are the fatty acid derivatives, insofar as these are distillable under the technical prerequisites in each case. If distillation is not practical on account of a high boiling point or for other reasons, such as for example in the case of triglycerides, then it is advisable to initially remove the impurities present in the starting material to be sulfonated in another manner. Thus, for example, in the case of the natural fats, and particularly the natural triglycerides, albuminous substances and slimy substances (mucins) should be separated in the deacidification and refining of the oils in a manner known per se.
  • the total quantity of sulfur-trioxide to be used is inter alia, dependent on the starting material to be sulfonated, and in general ranges from 1.1-1.8, preferably 1.2-1.6 m-ol sulfur-trioxide per mol fatty acid radical.
  • the quantity of the sulfur-trioxide applicable for as extensive as possible a sulfonation increases somewhat with the size of the fatty acid radical and in connection with monovalent alcohol esters, greatly increases with the size of the alcohol radical.
  • the sulfonation in accordance with the invention is effected in at least two reaction steps with the first reaction step conducted at temperatures between 30 and 70 and preferably between 40 and 65 C. and the second reaction 4step conducted at temperatures within the range of 75-95 and preferably 80-90 C. It is advisable to let the temperatures rise gradually so that the sulfur trioxide is constantly consumed and the temperature-limit of 70 C. is only exceeded after at least 50% preferably at least 65% of the total sulfur trioxide quantities have been used.
  • the sulfur trioxide is used in mixture with inert gases, such as for example air, nitrogen, carbonio acid, etc. and these mixtures may contain 2-40 volume percent, preferably 3-20 volume percent, sulfur trioxide.
  • the sulfur-trioxide addition and the course of the temperature are adjusted in dependence on one another and the time so that the sulfur trioxide added reacts as extensively as possible.
  • the rst reaction step is to be conducted over a longer reaction period than the second step with the latter requiring not more than l/s-t of the total reaction time but not less than about 5 and preferably not less thanA-15 minutes. If during the entire reaction time, the velocity of the sulfur trioxide addition is kept constant, then the second reaction step needs at most 1/3 of the entire reaction time. However, it is possible to still further shorten the reaction time in the second step through increased velocityof the sulfur trioxide addition.
  • the first step may also be effected with a non-uniform addition of the sulfur trioxide.
  • the velocity of the sulfur trioxide may be varied through the ow velocity of the sulfur trioxide and/ or in the case of sulfur trioxide inert gas mixtures through their concentration.
  • the reaction time depends on the starting material, on the sulfur trioxide quantity used, and on the temperature of the reaction. In general, times between and 150 minutes, preferably between 40 and 120 minutes, are to be used.
  • the products obtained in accordance with the invention' are sometimes still colored brown. However, they contain, assuming comparable conditions, such as for example equal degrees of sulfonation and equal sulfonation agent excesses, much less colored impurities than the products produced according to known processes. Theyl may thus be converted with much smaller bleaching agent quantities into light-colored unobjectionable products.
  • the bleaching of the acid sulfonation products may be carried out according to copending application Serial No. 194,998 tiled the same day herewith by treatment with hydrogen peroxide in amounts of 0.2-6 weight percent and preferably 1-4 weight percent hydrogen petroxide, calculated as 100% product.
  • hydrogen peroxide is preferably charged as 20-75 weight percent product and particularly as 30-50 weight percent product.
  • this sulfuric acid mathematically considered, should represent a mixture of sulfur trioxide and water with a sulfur trioxide content up to 95 weight percent and preferably up to -50 weight percent.
  • the bleaching is effected at temperatures within the range of 20-100 and preferably of 40-80 C.
  • the products produced may be converted into esters in a manner known per se.
  • esterication components the monoor polyvalent alcohols present as alcohol components in the initially mentioned fatty acid esters may be used. This esteriiication is desirable above all for the production of the esters from sulfo-carboxylic acids and monovalent alcohols containing at least 6 carbon atoms because the esters per se when used as startin-g materials fo-r the sulfonation react slower within increasing magnitude of the alcohol radical and good degrees of sulfonation are obtainable only with greater quantities of sulfur trioxide.
  • the esteriiication of the acid sulfonation products may take place before or after the bleaching. If the bleached su-lfo-fatty acids are used, then the mono-salts neutralized at the sulfo-'acid group may also be processed.
  • the sulfonation is preferably carried out continuously i in such a manner that the starting material is passed through reaction zones, in which the temperature is raised from zone to zone, and in which, according to the proportion of the consumption, sulfur trioxide is dissolved in the starting material.
  • the apparatus according to FIG. 1 may, for example, be used for the carrying out of the process.
  • the reaction vessel consists of the pipe 1, which is divided through partitions 2 into reaction zones. These partitions are here shown as sieve bottoms but, of course, in their place other separations which permit a owing through of the material to be sulfonated from above downwardly and of the sulfur trioxide inert gas mixture from below upwardly may be used.
  • the reaction zones may also be provided with contact improving installations, such as for example, filling bodies, bellor sieve-bottoms or other known installations, which improve the contact between gas and liquid wherein the liquid to be sulfonated lls the Zones more or less completely, or, for example, in trickling through vessels with bottom type installations only occupies a small part of the vessel space.
  • Each reaction zone is surrounded by a temperature jacket 6 which hasl an inlet and an outlet 7 and 8 for the heat exchange agent.
  • a line 9 leads into the reaction chamber, through which the sulfur trioxide inert gas mixture is introduced.
  • the starting material to be processed is passed through the line 4 into the head of the reaction vessel by means of the distributor 5 in the form of a sprinkler, a sprayer nozzle or the like. The material then ilowsthrough the individual reaction zones,
  • FIG. 2 shows a variant of the reaction zones according to FIG. 1.
  • each reaction zone is defined by an independent vessel connected 'behind the other in series.
  • the advantage of the working with the devices according to FIG.- 2 consists therein that in each reaction zone the inert gas free fram the sulfur trioxide is drawn off through the line 10.
  • substantially the same reference numbers are used as in FIG. 1.
  • FIG. 3 shows a device, as it has proved suitable for both production and laboratory scale carr/ing-out of the process.
  • the reaction vessel 13 is surrounded by a temperature jacket 6 with the inlet and outlet 7 and 8.
  • the lines 14 and 15 with the valves 16 and 17, through which the material to be sulfonated and the sulfur trioxide inert gas mixture are introduced.
  • the inert gas free from sulfur trioxide, leaves the reaction vessel through the line 19, and the processed material passes out, through the overflow 1.8 at a rate corresponding to the rate of introduction of new material into the reaction vessel.
  • the overliow 18 is connected to the inlet 4 of a further series connected reaction vessel of identical construction and several such vessels may be series connected.
  • Example 1 For the carrying out of the process described here, 5 vessels according to FiG. 3 are connected one after another in series. The content of each vessel up to the over-iiow amounts to 40 ccm.
  • a lauric acid methyl ester which had been obtained from a coconut-oil hardened to an iodine number of 0.2 and esteried with methyl alcohol followed by fractionating'out of the lauric acid methyl ester.
  • the first four reaction vessels were filled with this ester and the heating adjusted so that the reaction mixture present in the vessels had during the entire test the following temperatures, increasing from vessel to vessel: 1st vessel: second vessel: 60, third vessel: 70; vfourth vessel 80, fifth vessel: 80 C.
  • Sulfur trioxide, diluted with a 20-fold quantity of air was blown in the first four vessels in such quantities that in the individual Vessels the following sulfur trioxide quantities were taken up, in percent of the stoichiometrically necessary quantity for a quantitative sulfonation: 1st: 52, 2nd: 78, 3rd: 104, and 4th: 130%. No sulfur trioxide air mixture was blown 'into the 5th vessel.
  • the sulfonation product was bleachedfor 2 hours at 55-60" C. with 3% H2O2 and then neutralized with 5% soda-lye.
  • the degree of sulfo-V nation of the product was 94%.
  • a 5% solution of the crude acid sulfonation product showed in the Lovibond- Tintometer in a 4 cell, the following colorAvalues:
  • 117 g. of this mixture (iodine number 0.3) per hour were brought together with gaseous sulfur trioxide, diluted with a -fold air quantity, wherein the 1.3-fold of the S03 quantity stoichiometrically necessary for a quantitative sulfonation, was used.
  • the reaction vessels were kept during the sulfonation at the following temper passing: 50, 50, 65, 80, 80 C. respectively.
  • the reaction product running olf was bleached for 2 hours at 50 C. with 3% H2O2 (as aqueous solution), and then neutralized.
  • the color Lovibond values were:
  • Example 6 in the latter was used diluted with a 20-fold air quantity.
  • the temperatures in the vessels were, as also in Example 5, 50, 50, 65, 80 and 80 C. respectively.
  • the resulting reaction product was bleached for 2 hours at 55- 60 C. with 2% H2O2 (as 40% aqueous solution) and then neutralized with 5% aqueous-soda-lye.
  • the degree of sulfonation of the product amounted to 95.5%, the Lovibond color values were:
  • the first four reaction vessels were filled with the esterand the heating was so adjusted that the material in the vessels had during the entire test the following respective temperatures rising from vessel to vessel: 50, 50, 65, 80, 85 C.
  • ester per hour was continuously pumped into the first, and into the first four, reaction vessels so much of the above-mentioned sulfur trioxide air mixture was introduced that the ester passing out of the fourth vessel had taken up in all 1.3 mol per mol of fatty acid ester and in the 1st vessel 40% and in the 2nd to the 4th vessels 20% each of this sulfur trioxide quantity had been taken up. No sulfur trioxide was blown into the fifth vessel; this vessel serving for the after-reacting.
  • the product thus obtained was continuously bleached and for this purpose was rst of all cooled to 20-22 C. Then, 2420 g. per hour of the cooled product were mixed with 181 g. per hour of 20% aqueous hydrogen peroxide. The initially occurring reaction heat was removed in a cooler which the product left at a temperature of 40 -with the invention.
  • Example 8 The part-s a and b of this example demonstrate a continuous mode of operation falling outside of the scope of the invention for comparison with part c in accordance

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)
  • Fats And Perfumes (AREA)
US194840A 1961-08-08 1962-05-15 Sulfonation of fatty acids and their esters Expired - Lifetime US3256303A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1961H0043358 DE1246718C2 (de) 1961-08-08 1961-08-08 Verfahren zur Herstellung von sulfonierten Fettsaeuren bzw. sulfonierten Fettsaeureestern und gegebenenfalls deren Salzen

Publications (1)

Publication Number Publication Date
US3256303A true US3256303A (en) 1966-06-14

Family

ID=7155165

Family Applications (1)

Application Number Title Priority Date Filing Date
US194840A Expired - Lifetime US3256303A (en) 1961-08-08 1962-05-15 Sulfonation of fatty acids and their esters

Country Status (6)

Country Link
US (1) US3256303A (enrdf_load_stackoverflow)
CH (1) CH421082A (enrdf_load_stackoverflow)
DE (1) DE1246718C2 (enrdf_load_stackoverflow)
DK (1) DK117139B (enrdf_load_stackoverflow)
GB (1) GB1001286A (enrdf_load_stackoverflow)
NL (2) NL140235B (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969375A (en) * 1973-11-29 1976-07-13 Lion Fat & Oil Co., Ltd. Method of manufacturing salt of α-sulfofatty acid ester
US4547318A (en) * 1983-05-30 1985-10-15 Henkel Kgaa Preparation of color-stable, light-colored, aqueous salt pastes of wash-active, α-sulfofatty acid esters
US4671900A (en) * 1980-12-19 1987-06-09 Henkel Kommanditgesellschaft Auf Aktien Preparation of light-colored, wash active α-sulfofatty acid
US4695409A (en) * 1984-09-03 1987-09-22 Henkel Kommanditgesellschaft Auf Aktien Control of disalt in α-sulfofatty acid ester surfactants
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
US5587500A (en) * 1993-09-17 1996-12-24 The Chemithon Corporation Sulfonation of fatty acid esters
CN112540077A (zh) * 2020-11-30 2021-03-23 邢台学院 一种原位检测种子中脂肪酸不饱和度的方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5143716A (en) * 1974-10-08 1976-04-14 Lion Fat Oil Co Ltd Arufua suruhoshibosanesuteruenno seizoho
JPS58157762A (ja) * 1982-03-15 1983-09-19 Lion Corp α−スルホ脂肪酸エステルの製造方法
JPS58157763A (ja) * 1982-03-15 1983-09-19 Lion Corp αスルホ脂肪酸エステルの製造方法
DE3834393A1 (de) * 1988-10-10 1990-04-26 Henkel Kgaa Verfahren zur herstellung hellfarbiger alpha-sulfofettsaeurealkylestersalze
DE4017467A1 (de) * 1990-05-30 1991-12-05 Henkel Kgaa Verfahren zur herstellung von hellfarbigen alpha-sulfofettsaeurealkylester- alkalimetallsalzpasten

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE967585C (de) * 1952-10-14 1957-11-28 Henkel & Cie Gmbh Verfahren zur Herstellung von sulfonierten Fettsaeurenitrilen

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969375A (en) * 1973-11-29 1976-07-13 Lion Fat & Oil Co., Ltd. Method of manufacturing salt of α-sulfofatty acid ester
US4671900A (en) * 1980-12-19 1987-06-09 Henkel Kommanditgesellschaft Auf Aktien Preparation of light-colored, wash active α-sulfofatty acid
US4547318A (en) * 1983-05-30 1985-10-15 Henkel Kgaa Preparation of color-stable, light-colored, aqueous salt pastes of wash-active, α-sulfofatty acid esters
US4695409A (en) * 1984-09-03 1987-09-22 Henkel Kommanditgesellschaft Auf Aktien Control of disalt in α-sulfofatty acid ester surfactants
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
US5587500A (en) * 1993-09-17 1996-12-24 The Chemithon Corporation Sulfonation of fatty acid esters
CN112540077A (zh) * 2020-11-30 2021-03-23 邢台学院 一种原位检测种子中脂肪酸不饱和度的方法
CN112540077B (zh) * 2020-11-30 2022-12-06 邢台学院 一种原位检测种子中脂肪酸不饱和度的方法

Also Published As

Publication number Publication date
GB1001286A (en) 1965-08-11
CH421082A (de) 1966-09-30
NL281859A (enrdf_load_stackoverflow)
DK117139B (da) 1970-03-23
DE1246718C2 (de) 1974-05-22
DE1246718B (de) 1967-08-10
NL140235B (nl) 1973-11-15

Similar Documents

Publication Publication Date Title
US3256303A (en) Sulfonation of fatty acids and their esters
US2360844A (en) Preparation of detergents
Stein et al. α-Sulfonated fatty acids and esters: Manufacturing process, properties, and applications
US2383632A (en) Process of treating fatty glycerides
US4671900A (en) Preparation of light-colored, wash active α-sulfofatty acid
US4371470A (en) Method for manufacturing high quality fatty acid esters
US2383633A (en) Process for treating fatty glycerides
US2271619A (en) Process of making pure soaps
KR100202472B1 (ko) 알파-술폰지방산알킬에스테르알칼리금속염의담색페이스트의제조방법
US2383614A (en) Treatment of fatty glycerides
KR100202473B1 (ko) 엷은색알파-술폰지방산알킬에스테르알칼리금속염페이스트의제조방법
US3251868A (en) Sulfonation of saturated fatty acid esters of polyvalent alcohols
GB2141706A (en) Process for the production of color-stable, light-colored, aqueous salt pastes of wash-active -sulfofatty acid esters
US2383599A (en) Treating fatty glycerides
US3159657A (en) Preparation of light-colored sulfonated fatty acids and fatty acid derivatives
Yamane Recent findings and experiences with alpha olefin sulfonates
Chahine et al. Positional isomers formed during the hydrogenation of cottonseed oil
Norris et al. Interesterification reactions of triglycerides
US2164291A (en) Hydrogenated oil product
US3737444A (en) Continuous process for the separation of mixtures of fatty acids of different melting points
US2868812A (en) Manufacture of fatty acid monoesters of glycerol monosulfuric acid and salts thereof
US5990074A (en) Process to make soap
US2334850A (en) Refining of fatty acid esters and fatty acids
Mattil The formation of isomers of polyunsaturated acids during the hydrogenation of soybean oil
Eckey et al. Directed interesterification in glycerides. Reaction in presence of added glycerol