US2371284A - Preparation of sulphated fatty - Google Patents

Preparation of sulphated fatty Download PDF

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US2371284A
US2371284A US2371284DA US2371284A US 2371284 A US2371284 A US 2371284A US 2371284D A US2371284D A US 2371284DA US 2371284 A US2371284 A US 2371284A
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molecular weight
alcohols
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated

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  • Another object is to provide an improved procedure for obtaining sulphonated or sulphated low molecular weight alkyl esters of high molecular fatty acids with enhanced yield.
  • a low molecular weight alkyl fatty ester is formed from a low molecular weight alkanol such as methanol, ethanol, isopropanol or butanol and an unsaturated or hydroxy fatty acid, such as oleic, ricinoleic, erucic, and so forth, in the presence of a suitable catalyst such as an alkylated naphthalene sulphonic acid.
  • a low molecular weight alkanol such as methanol, ethanol, isopropanol or butanol
  • an unsaturated or hydroxy fatty acid such as oleic, ricinoleic, erucic, and so forth
  • This reaction may be carried out at a temperature of 80 to 100 (1., withv refluxing, if necessary, *nd preferably with constant stirrin or agitation for a period of 2 to 8 hours.
  • the preferred temperature for the reaction is C. to 0., and the preferred time is from 4 to 6 hours, and generally when the reaction is carried on under these conditions there is a yield of ester amounting to 90% to 95%.
  • esters of somewhat lighter color may be produced.
  • the amount of catalyst usually found desirable for. optimum results may range from 5% to 10% of the amount of the reaction mixture and when the reaction is completed the catalyst together with the water produced in the reaction may bepermitted to settle out and drawn ofi if desired.
  • any alkylated aromatic sulphonic acid may be employed, which is not darkening, among which acids may be alkyls ated or unalkylated aromatic sulphonic acids, such as methyl, ethyl, propyl, butyl, amyl or other alkylated benzene, toluene or naphthalene sul phonic acids.
  • This first step appears to result in formation of low molecular weight alkyl esters of high molecular weight unsaturated or hydroxy fatty acids.
  • the ester which has been prepared in the first step above stated is cooled to a temperature of about to C., and a molal weight of a complex alcohol or ester having ether, ketone, or amino groups in the molecule is added per mol of fatty acid.
  • complex alcohols or esters ma be allphatic, aromatic, or mixed types and among the complex alcohols or esters which have been found to be particularly suitable are the following groups and classifications:
  • (l) Esters containing an ether grouping such as dietlvyleneglycol monobutyl ether acetate.
  • Alcohols containing an ether grouping such as the monobutyl ether of diethyleneglycol.
  • Alcohols containing amino groups such as monoethanolamine.
  • Ethylene glycol monomethyl ether acetate (methyl "Cellosolve” acetate)
  • Ethylene glycol monoethyl ether acetate (“Cellosolve acetate)
  • Ethylene glycol monobutyl ether acetate (butyl Among the preferred amino alcohols which may be used are:
  • the amount of sulphating agent should be at least of the total weight of the reaction mixture and may be as high as 300%.
  • the resulting product is washed, preferably with a 10% to 20% solution of common salt, and then neutralized with caustic soda or any other suitable alkali,
  • the final products are clear, oily liquid of either an amber or a reddish color and give clear solutions in water, which have remarkable foaming properties, even at highly attenuated dilutions.
  • a process of preparing sulphated fatty acid esters which comprises first treatinghigh molecular weight unsaturated fatty acids with a low molecular weight aliphatic monohydriic alcohol in the presence of a catalyst and then treating the thus obtained product with a complex aliphatic alcohol selected from the group consisting of low molecular weight ether alcohols, hetc alcohols, amino alcohols and the esters of these alcohols with low molecular weight fatty acids, inthe presence of a sulphating agent.
  • a process of preparing sulphated fatty acid esters which comprises first treating high molecular weight unsaturated fatty acids with a low molecular weight aliphatic monohydric alcohol in the presence of a catalyst and then treating the thus obtained product with a complex aliph'atic alcohol selected from the group consisting of low molecular weight ether alcohols, keto alcohols, amino alcohols and the esters of these alcohols with low molecular weight fatty acids, in the presence of concentrated sulphuric acid.
  • a process of preparing sulphated fatty acid esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic alcohol in the presence of an aromatic sulphonic acid and then combining the reaction mixture with an ether of a polyhydroxy low molecular weight aliphatic alcohol in the presence of a sulphating agent.
  • a process of preparing sulphated fatty acid esters which comprises first combining oleic acid with methyl alcohol in the presence of an aromatic sulphonic acid and then combining the reaction mixture with an ether of a polyhydroxy low moleoular'weight aliphatic alcohol in the presence of a sulphating agent.
  • a process of preparing sulphated fatty acid esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic alcohol in the presence of an aromatic sulphonic acid and then combining the reaction mixture with an ether of a polyhydroxy low molecular weight aliphatic alcohol selected from the group consisting of alkylene glycol mono-alkyl ethers in the presence of a sulphating agent.
  • a process of preparing sulphated fatty acid esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic alcohol in the presence of an aromatic sulphonic acid and then combining the reaction product with an alkanolamine in the presence of a sulphating agent.
  • a process of preparing sulphated fatty acid esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic. alcohol in the presence of an aromatic sulphonic acid and then combining the reaction product with hydroxyethyl ethylene diamine in the presence of a sulphating agent,
  • a process of preparing sulphated fatty acid esters which comprises first treating high molecular weight unsaturated fatty acids with a, low molecular weight aliphatic monohydricalcohol in the presence of an aromatic sulphonic acid and then treating the thus obtained product with a low molecular weight aliphatic acid ester of an ether of a polyhydroxy low molecular weight aliphatic alcohol in the presence of a sulphating agent.
  • a process of preparing sulphated fatty acid esters which comprises first treating high molecular weight unsaturatedfatty acids with a low molecular weight aliphatic monohydric alcohol in the presence of an aromatic sulphonic acid and then treating the thus obtained product with an acetate of an alkylene glycol mono-alkyl ether in the presence of a sulphating agent.
  • a process of preparing sulphated fatty aci esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic alcohol in the presence of a naphthalene sulphonic acid a'nd then combining the reaction product with mono-ethanolamine.
  • a process of preparing sulphated fatty acid esters which comprises first treating oleic acid with methyl alcohol in the presence of naphthalene sulphonic acid as a catalyst and then treating the thus obtained product with a complex aliphatic alcohol selected from the group consisting of low molecular weight ether alcohols, keto alco'hols, amino alcohols and their esters with low molecular weight fatty acids in the presence of concentrated sulphuric acid.
  • a process for preparing completely water soluble complex sulphated fatty acid esters comprising first treating high molecular weight unsaturated fatty acids with a low molecular weight monohydric aliphatic alcohol in the presence of a suitable catalyst while maintaining a temperature of about between 80 C. to 100 C.
  • a process for preparing completely water soluble complex sulphated fatty acid esters comprising first treating high molecular weight unsaturated fatty acids with a low molecular weight monohydric aliphatic alcohol in the presence of a suitable catalyst while maintaining a temperature of about between 80 C. to 100 C. for a period of about 2 to 8 hours and treating the hereby obtained ester in the purified freshly prepared state directly with a complex aliphatic alcohol selected from the group consisting of ether alcohols, keto alcohols, amino alcohols and the esters of these alcohols with low molecular weight fatty acids in the presence of at least an equal quantity of a sulphating agent while maintaining a'temperature of about 20 to 25 C. for a period of about 1 to 3 hours, the hereby produced complex sulphated fatty acid ester having wetting properties which are approximately three times more powerful than that obtained by a one step treatment of the commercially available ester.
  • a process forpreparing completely water soluble complex sulphated fatty acid esters comprising first treating high molecular weight unsaturated fatty acids with a low molecular weight monohydric aliphatic alcohol in the presence 01' a suitable catalyst while maintaining a temperature of about between C. to C.
  • a process for preparing completely water soluble complex sulphated fatty acid esters comprising first treating high molecular weight unsaturated fatty acids with a low molecular weight monohydric aliphatic alcohol in the presence of alkylated aromatic sulphuric acid as a catalyst while maintaining a temperature of about between 80 C. to 100 C.

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

Description

Patented 1 3, 1945 I 2,311.2 PREPARATION or sonrm'mn mm ns'rans Alton A. Cook, Glen Ridge, and Curt T-jorn and Joseph Zaparanick, Westfield, N. 1., assignors to Arkansas Companyfi lna, Newark, N. J., a
corporation of New York Application October 16, 1941, Serial No. 415,218
No Drawing.
-' 15 Claims. (c1. zoo-+400)" a strong sulphating or sulphonating agent.
For example, where butyl oleate or butyl ricinoleate are first prepared and then treated with sulphuric acid, most desirable results are not obtained.
This is also true in cases where mixtures of butyl alcohol and oleic acid are sulphonated or where butyl alcohol is first combined with sulphuric acid following which the butyl acid sulphate resets with the fatty acid.
Furthermore, many disadvantages have been observed in processes where the fatty acid glycerides are sulphonated in the presence of a low molecular weight aliphatic alcohol, as for example, where castor oil is sulphated or sulphonated in the presence. of isopropyl alcohol as a solvent.
It is among the objects of the present invention to prepare improved sulphated or sulphonated fatty esters with greater yield and with a smaller production of undesirable by-products, which may be more readily and effectively used as penetrating, emulsifying, and washing agents, and generally as surfac active agents particularly in the textile fields.
Another object is to provide an improved procedure for obtaining sulphonated or sulphated low molecular weight alkyl esters of high molecular fatty acids with enhanced yield.
Still further objects and advantages will appear from the more detailed description set forth below, it being understood, however, that this more detailed description is given by way of illustration, sinc various changes therein may be made by those skilled in the art without departing from the scope and spirit of the invention.
In accomplishing the above objects it has been found most satisfactory to form the fatty esters by a series of steps, preferably two in number, which are most economically and satisfactorily carried out in succession.
According to the first step a low molecular weight alkyl fatty ester is formed from a low molecular weight alkanol such as methanol, ethanol, isopropanol or butanol and an unsaturated or hydroxy fatty acid, such as oleic, ricinoleic, erucic, and so forth, in the presence of a suitable catalyst such as an alkylated naphthalene sulphonic acid.
This reaction may be carried out at a temperature of 80 to 100 (1., withv refluxing, if necessary, *nd preferably with constant stirrin or agitation for a period of 2 to 8 hours.
The preferred temperature for the reaction is C. to 0., and the preferred time is from 4 to 6 hours, and generally when the reaction is carried on under these conditions there is a yield of ester amounting to 90% to 95%.
By the use of lowertemperatures and shorter reaction periods esters of somewhat lighter color may be produced.
In all cases, however, it has been found most desirable to use molal proportions of alcohols and fatty acids, except in those cases wher the alcohol is highly volatile. In such cases about 10% in excess over molal proportions may be used to cover possible losses.
The amount of catalyst usually found desirable for. optimum results may range from 5% to 10% of the amount of the reaction mixture and when the reaction is completed the catalyst together with the water produced in the reaction may bepermitted to settle out and drawn ofi if desired. t
In this first step it is possible to use as the fatty acids:
Oleic Linoleic Linolenic Eleostearlc Erucic Ricinoleic or the mixed fatty acids derived from the following oils:
Soy bean oil Corn oil Olive oil Tea seed oil Sperm oil Fish oils Rice bran oil Grapefruit seed oil Sunflower seed oil As the low molecular weight alcohols there may be employed the following alcohols:
or instead of these low molecular weight alcohols it is also possible to use their esters such as Formates Acetates Propionates Butyrates Lactates Citrates Succinates As the catalyst, generally any alkylated aromatic sulphonic acid may be employed, which is not darkening, among which acids may be alkyls ated or unalkylated aromatic sulphonic acids, such as methyl, ethyl, propyl, butyl, amyl or other alkylated benzene, toluene or naphthalene sul phonic acids.
Among the preferred compounds which may be employed are:
Mono butyl alpha naphthalene snlphonic acid Beta naphthalene sulphonic acid Para toluene sulphonic acid Sulphuric acid itself is generally not utilized because of its darkening effect.
This first step appears to result in formation of low molecular weight alkyl esters of high molecular weight unsaturated or hydroxy fatty acids.
In the second step the ester which has been prepared in the first step above stated is cooled to a temperature of about to C., and a molal weight of a complex alcohol or ester having ether, ketone, or amino groups in the molecule is added per mol of fatty acid.
These complex alcohols or esters ma be allphatic, aromatic, or mixed types and among the complex alcohols or esters which have been found to be particularly suitable are the following groups and classifications:
(l) Esters containing an ether grouping, such as dietlvyleneglycol monobutyl ether acetate.
(2) Alcohols containing an ether grouping, such as the monobutyl ether of diethyleneglycol.
(3) Alcohols or esters containing a ketone group,
such as diacetone alcohol.
(4) Alcohols containing amino groups such as monoethanolamine.
As preferred alcohols and esters which may be used:
Ethylene glycol monomethyl ether acetate (methyl "Cellosolve" acetate) Ethylene glycol monoethyl ether acetate ("Cellosolve acetate) -Ethylene glycol monobutyl ether acetate (butyl Among the preferred amino alcohols which may be used are:
' Monoethanolamine Diethanolamine Trietltanolamine Phenylethanolamine Hydroxyethyl ethylenediamine Diethylaminoethanol 2 amino-2 methyl- 1 propanol Di n-butyl aminoethanol Trimethylol aminomethane ether (methyl The above mixture is, then treated with a sulphating agent, preferably commercial 66 B. sulphuric acid at a temperature of 20 to 25 C. for
l to 3 hours. The amount of sulphating agent should be at least of the total weight of the reaction mixture and may be as high as 300%.
During this second step or reaction it appears that the larger or more complex radical replaces the smaller and simpler radical at least in part; that is, if methyl oleate, produced by the first reaction is treated with the monobutyl ether of diethylene glycol acetate, the radical "butyl ether diethylene glycol" appears to replace in part the methyl group in its combination with oleic acid.
After completion of the second reaction step, the resulting product is washed, preferably with a 10% to 20% solution of common salt, and then neutralized with caustic soda or any other suitable alkali,
In most cases a partial neutralization to a pH of between 5 and 7 is preferable.
The final products are clear, oily liquid of either an amber or a reddish color and give clear solutions in water, which have remarkable foaming properties, even at highly attenuated dilutions.
On the Standard canvas disc method for measuring efficiency of penetration, these products give considerabl better results than sulphated esters produced by the other methods previously described.
To give some examples of various reagents which may be utilized, all parts being by weight:
, Ex'AMPLl: I
First'step Parts Oleic acid 282 Methyl alcohol 35 Catalyst 25 Second step Parts Methyl oleate 300 Diethyleneglycol monobutylether acetate--- 204 Sulphuric acid 600 EXAMPLE II First step' Parts Ricinoleic acid 298 Ethyl acetat 88 Catalyst 20 Second step Parts Ethyl ricinoleate 370 Monoethanolamine 60 Sulphuric acid 500 EXAMPLE III First step Parts Soya bean fatty acids 281 Anhydrous ethyl alcohol 50 Catalyst 20 Second step Ethyl soya bean fatty acid compound 309 Ethylene glycol monoethyl ether acetate 132 Sulphuric acid 500 EXAMPLE IV First step Rape seed fatty acids 303 Butyl alcohol '75 Catalyst 25 asrmss Second step Butyl rape seed I 359 Ethylene glycol mono butyl ether 118 Sulphuric acid 500 ExntruV a First step Corn oil fatty acids 28 Isopropanol 65 1 Catalyst I 7 Second step Isopropanol corn oil 326 Diacetone 116 sulphuric a 500 Exmrtz VI First step Peanut oil fatty acids. 2'18 Methanol 35 Catalyst 20 Second step Methyl peanut oil.... 292 Hydroxy ethyl ethylene diamine 105 Sulphuric acid 800 Emmett: VII
First step 0181c acid 382 Butyl air-ohm '15 Catalyst 20 Second step -Butyl oleate 338 Diethylene glycol mono phenyl ether-.'.. 138 Sulphuric acid----.... 600
EXAHPLI VIII First step Ricinoleic acid 298 Methanol 35 Catalyst 20 second step Methyl ricinoleatea; 312 Phenyl ethanolamine 13'! Sulphuric a id 600 The above wetting agents are effective penei the claimed invention, the practical embodiments herein described merely showing some of the various features entering into the application of the invention.
What is claimed is:
l. A process of preparing sulphated fatty acid esters which comprises first treatinghigh molecular weight unsaturated fatty acids with a low molecular weight aliphatic monohydriic alcohol in the presence of a catalyst and then treating the thus obtained product with a complex aliphatic alcohol selected from the group consisting of low molecular weight ether alcohols, hetc alcohols, amino alcohols and the esters of these alcohols with low molecular weight fatty acids, inthe presence of a sulphating agent.
2. A process of preparing sulphated fatty acid esters which comprises first treating high molecular weight unsaturated fatty acids with a low molecular weight aliphatic monohydric alcohol in the presence of a catalyst and then treating the thus obtained product with a complex aliph'atic alcohol selected from the group consisting of low molecular weight ether alcohols, keto alcohols, amino alcohols and the esters of these alcohols with low molecular weight fatty acids, in the presence of concentrated sulphuric acid.
3. A process of preparing sulphated fatty acid esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic alcohol in the presence of an aromatic sulphonic acid and then combining the reaction mixture with an ether of a polyhydroxy low molecular weight aliphatic alcohol in the presence of a sulphating agent.
4. A process of preparing sulphated fatty acid esters which comprises first combining oleic acid with methyl alcohol in the presence of an aromatic sulphonic acid and then combining the reaction mixture with an ether of a polyhydroxy low moleoular'weight aliphatic alcohol in the presence of a sulphating agent..
5. A process of preparing sulphated fatty acid esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic alcohol in the presence of an aromatic sulphonic acid and then combining the reaction mixture with an ether of a polyhydroxy low molecular weight aliphatic alcohol selected from the group consisting of alkylene glycol mono-alkyl ethers in the presence of a sulphating agent.
6. A process of preparing sulphated fatty acid esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic alcohol in the presence of an aromatic sulphonic acid and then combining the reaction product with an alkanolamine in the presence of a sulphating agent.
7. A process of preparing sulphated fatty acid esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic. alcohol in the presence of an aromatic sulphonic acid and then combining the reaction product with hydroxyethyl ethylene diamine in the presence of a sulphating agent,
' 8. A process of preparing sulphated fatty acid esters which comprises first treating high molecular weight unsaturated fatty acids with a, low molecular weight aliphatic monohydricalcohol in the presence of an aromatic sulphonic acid and then treating the thus obtained product with a low molecular weight aliphatic acid ester of an ether of a polyhydroxy low molecular weight aliphatic alcohol in the presence of a sulphating agent.
9. A process of preparing sulphated fatty acid esters which comprises first treating high molecular weight unsaturatedfatty acids with a low molecular weight aliphatic monohydric alcohol in the presence of an aromatic sulphonic acid and then treating the thus obtained product with an acetate of an alkylene glycol mono-alkyl ether in the presence of a sulphating agent.
a 10. A process of preparing sulphated fatty aci esters which comprises first combining high molecular weight fatty acids with a low molecular weight aliphatic alcohol in the presence of a naphthalene sulphonic acid a'nd then combining the reaction product with mono-ethanolamine.
11. A process of preparing sulphated fatty acid esters which comprises first treating oleic acid with methyl alcohol in the presence of naphthalene sulphonic acid as a catalyst and then treating the thus obtained product with a complex aliphatic alcohol selected from the group consisting of low molecular weight ether alcohols, keto alco'hols, amino alcohols and their esters with low molecular weight fatty acids in the presence of concentrated sulphuric acid.
12. A process for preparing completely water soluble complex sulphated fatty acid esters, comprising first treating high molecular weight unsaturated fatty acids with a low molecular weight monohydric aliphatic alcohol in the presence of a suitable catalyst while maintaining a temperature of about between 80 C. to 100 C. for a period of about 2 to 8 hours and treating the hereby obtained ester in the purified freshly prepared state directly with a complex aliphatic alcohol selected from the group consisting of ether alcohols, keto alcohols, amino alcohols and the esters of these alcohols with low molecular weight fatty acids in the presence of a sulphating agent, the hereby produced complex sulphated fatty acid ester having wetting properties which are approximately three times as powerful than that obtained by a one step treatment of the commer-' cially available ester.
13. A process for preparing completely water soluble complex sulphated fatty acid esters, comprising first treating high molecular weight unsaturated fatty acids with a low molecular weight monohydric aliphatic alcohol in the presence of a suitable catalyst while maintaining a temperature of about between 80 C. to 100 C. for a period of about 2 to 8 hours and treating the hereby obtained ester in the purified freshly prepared state directly with a complex aliphatic alcohol selected from the group consisting of ether alcohols, keto alcohols, amino alcohols and the esters of these alcohols with low molecular weight fatty acids in the presence of at least an equal quantity of a sulphating agent while maintaining a'temperature of about 20 to 25 C. for a period of about 1 to 3 hours, the hereby produced complex sulphated fatty acid ester having wetting properties which are approximately three times more powerful than that obtained by a one step treatment of the commercially available ester.
14. A process forpreparing completely water soluble complex sulphated fatty acid esters, comprising first treating high molecular weight unsaturated fatty acids with a low molecular weight monohydric aliphatic alcohol in the presence 01' a suitable catalyst while maintaining a temperature of about between C. to C. for a period of about 2 to 8 hours and treating the hereby obtained ester in the purified freshly prepared state directly with a complex aliphatic alcohol selected from the group consisting of ether alcohols, keto alcohols, amino alcohols and the esters of these alcohols with low molecular weight fatty acids in the presence of a sulphating substance, neutralizing the final product with alkali to a pH of between about 5 and 7, the hereby produced complex sulphated fatty acid ester having wetting properties which are approximately three times more powerful than that obtained by a one step treatment of the commercially available ester.
15. A process for preparing completely water soluble complex sulphated fatty acid esters, comprising first treating high molecular weight unsaturated fatty acids with a low molecular weight monohydric aliphatic alcohol in the presence of alkylated aromatic sulphuric acid as a catalyst while maintaining a temperature of about between 80 C. to 100 C. for a period of about 2 to 8 hours and treating the hereby obtained ester in the purified freshly prepared state directly with a complex aliphatic alcohol selected from the group consisting of ether alcohols, keto alcohols, amino alcoholsand the esters of these alcohols with low molecular weight fatty acids in the presence of a sulphating agent, the hereby produced complex sulphated fatty acid ester having wetting properties which are approximately three times more powerful than that obtained by a one step treatment of the commercially available ester.
ALTON A. COOK. CURT "I'JORN. JOSEPH ZAPARANICK.
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2447186A (en) * 1945-01-01 1948-08-17 Photo Technical Corp Producing lower alkyl esters
US2460968A (en) * 1943-09-28 1949-02-08 Innovations Chimiques Sinnova Method for the obtainment of aliphatic sulfonic acids and esters thereof
US2553716A (en) * 1946-07-19 1951-05-22 Rare Galen Inc Mild detergent and method of making same
US2623887A (en) * 1948-05-22 1952-12-30 Standard Oil Dev Co Rust inhibiting composition
US3027388A (en) * 1960-04-07 1962-03-27 Jr Cecil R Smith Method of preparing a drying oil and intermediates therefor
US3270038A (en) * 1961-05-26 1966-08-30 Colgate Palmolive Co Sulphonation of organic compounds
US4315040A (en) * 1978-11-25 1982-02-09 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Parting oil component for baked goods and parting oils
WO2015188233A1 (en) * 2014-06-13 2015-12-17 Southern Biofuel Technology Pty Ltd A process for the preparation of fatty acid alkyl esters

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2460968A (en) * 1943-09-28 1949-02-08 Innovations Chimiques Sinnova Method for the obtainment of aliphatic sulfonic acids and esters thereof
US2447186A (en) * 1945-01-01 1948-08-17 Photo Technical Corp Producing lower alkyl esters
US2553716A (en) * 1946-07-19 1951-05-22 Rare Galen Inc Mild detergent and method of making same
US2623887A (en) * 1948-05-22 1952-12-30 Standard Oil Dev Co Rust inhibiting composition
US3027388A (en) * 1960-04-07 1962-03-27 Jr Cecil R Smith Method of preparing a drying oil and intermediates therefor
US3270038A (en) * 1961-05-26 1966-08-30 Colgate Palmolive Co Sulphonation of organic compounds
US4315040A (en) * 1978-11-25 1982-02-09 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Parting oil component for baked goods and parting oils
WO2015188233A1 (en) * 2014-06-13 2015-12-17 Southern Biofuel Technology Pty Ltd A process for the preparation of fatty acid alkyl esters

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