US2159700A - Process for the manufacture of unsaturated fatty acids - Google Patents
Process for the manufacture of unsaturated fatty acids Download PDFInfo
- Publication number
- US2159700A US2159700A US54298A US5429835A US2159700A US 2159700 A US2159700 A US 2159700A US 54298 A US54298 A US 54298A US 5429835 A US5429835 A US 5429835A US 2159700 A US2159700 A US 2159700A
- Authority
- US
- United States
- Prior art keywords
- unsaturated fatty
- fatty acids
- alkali
- manufacture
- esters
- 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
Links
- 235000021122 unsaturated fatty acids Nutrition 0.000 title description 28
- 150000004670 unsaturated fatty acids Chemical class 0.000 title description 24
- 238000000034 method Methods 0.000 title description 19
- 238000004519 manufacturing process Methods 0.000 title description 14
- 239000003921 oil Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 239000003513 alkali Substances 0.000 description 12
- 150000002191 fatty alcohols Chemical class 0.000 description 12
- 239000000344 soap Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 7
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 7
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
- 239000005642 Oleic acid Substances 0.000 description 7
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 150000001447 alkali salts Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000000306 component Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- -1 unsaturated fatty acid salts Chemical class 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 229940084106 spermaceti Drugs 0.000 description 2
- 239000012177 spermaceti Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/295—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with inorganic bases, e.g. by alkali fusion
Definitions
- the alkali or earth alkali hydroxides are used preferably in a small excess previously to the reaction mixture.
- the end of the reaction is recognized when the evolution of the hydrogen gas stops.
- the formed soap is decomposed with acids.
- a mixture of unsaturated fattyacids of the type of oleic acid is obtained which not only resembles by colour, odour and physical and chemical com
- the process is suitably performed unstants the oleic acid obtained by the stearin' process by pressing of! the tallow but it is also like that product which is free of highly unsaturated easy inflammable and chemically unstable higher molecular weight unsaturated acids. Therefore it is suitable not only for greasing purposesbut also for the manufacture of textile soaps and textile soap preparations, for sulfonates for emulsion purposes and so on.
- the proposed method for the manufacture of valuable oleine is a new one and provides for obtaining those products from cheap raw materials not fit for food or for the manufacture of soaps, without troublesome pressure extraction or protracted fractional distillation. Therefore it is possible to make mixtures of high molecular unsaturated fatty acids in a more satisfactory way.
- the process above may also be performed by immediately submitting without previous filtration the raw materials to the fusion with alkali and then after decomposition of the formed soap separating by filtration the solid saturated fatty acids from the fluid unsaturated fatty acids of the type of oleic acid.
- Example 1 500 parts by weight of technical oleyl alcohol, (iodine number as obtained by cooling down to --15 C. and filtering in a cooled press the is distilling off. The temperature is slowly raised to 276-280 C., the quantity of hydrogen split off being a measure for the progress of the reaction. As soonas the evolutionof hydrogen is over the reaction mixture is cooled down and the formed soap is decomposed by diluted sulfuric acid. An oleic acid with the iodine number of 68-70 and a content of 9697% saponifiablefat is obtained.
- Example 2 500 parts by weight of sperm oil or arctic sperm oil (iodine number 85) are.worked up in the same manner as in Example 1 with 100 parts by weight of caustic soda and 25 parts by weight of water. The solid portions of the sperm oil or arctic sperm oil are separated in the manner described in Example l. 515 parts'by weight of a mixture of unsaturated fatty acids are obtained (saponification number 202, iodine number 78-80, stock point 3). The mixture is suitable generally as a substitute for the usual oleic acid.
- the process for the manufacture of unsaturated fatty acids which comprises separating from sperm oil the saturated portion'which is solid at low temperatures, reacting the residual fluid portion with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature above 200 C. and under super-atmospheric pressure until the esters present are saponified and alkali salts of unsaturated fatty acids are formed from com-- ponents of the esters and reacting the unsaturated fatty acid salts with a mineral acid to produceunsaturated fatty acids.
- esters present are -saponified and alkali salts of unsaturated fatty acids are formed from both components of the esters and reacting the unsaturated fatty acid salts with amineral acid to produce unsaturated fatty acids.
- the process for the manufacture of unsaturated fatty acids which comprises reacting a mixture of unsaturated fatty alcohols obtained from the oils of sea animals with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature between 200 and 280 C. and under a pressure of about 5 atmospheres until the same is converted to alkali salts of unsaturated fatty acids and reacting the unsaturated fatty acid salts with a mineral acid to produce unsaturated fatty acids.
- the process for the manufacture of unsaturated fatty acids which comprises reacting a mixture of unsaturated fatty esters obtained from the oils of sea animals with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature, between about 200 and about 280 .C. and
- esters present are saponified 'and'alkali salts of unsaturated fatty acids are formed from both components of the esters and reacting the unsaturated fatty acid salts with a mineral acid to produce ,unsaturated fatty acids.
- the process for the manufacture of unsaturated fatty acids which comprises reacting material of the group consisting of unsaturated fatty alcohols and esters of unsaturated fatty alcohols with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature above 200 C. and under superatmospheric pressure until the same is converted to alkali salts of unsaturated fatty acids.
- the process for the manufacture of unsaturated fatty acids which comprises reacting material of the group consisting of unsaturated fatty alcohols and esters of unsaturated fatty alcohols with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature between about 200 and about 280 C. and under a pressure of about 5 salts ofunsaturated fatty acids.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
Patented May 23, 1939 UNITED. STATES PROCESS FOR THE MANUFACTURE OF UN- SATURATED FATTY ACIDS Karl Hennig, Rosslau in Anhalt, Germany, as-
signor to Deutsche Hydrierwerke Aktiengesell schaft, Berlin-Charlottenburg, Germany, a corporation of Germany No Drawing. Application December 13, 1935, Se-
rial No. 54,298. In Germany December 15,
' 7 Claims. '(Cl. 260-413) a It is known to saponify spermaceti or spermaceti oil by alkalis at higher temperatures ;whereby the fatty -alcohols contained in these fatty products as constituents of the esters are converted into, fatty acids. Probably in the presence of unsaturated fat-stuffs reactions occur corresponding. to the so-called Varrentrapp reaction, i. e., the unsaturated oleic acid is decomposed to saturated palml'tic acid forming 10 the soap of this fatty acid on fusion with alkali.
Now it has been found that the action of the alkali on the mixtures of fatty alcohols occur- H ring in the oils of sea/animals or their esters, particularly the naturally occurring esters such as sperm oil or arctic sperm oil may be so conducted" that the double links existing in the raw materials are preserved by maintaining certainlimits of alkali, temperature and concentration, but particularly by applying superat- 0 mospheric pressure. In this manner unsaturated fatty acids are formed in a practically quantitative yield from unsaturated fatty alcohols and likewise from such esters which contain only unsaturated fatty acid and unsaturated fatty alcohol components. These-called Varrentrapp reaction, i. e., the formation of a saturated fatty acid from an unsaturated fatty acid under loss of two carbon atoms is entirely eliminated by avoiding excess of alkali and passing beyond certain limits of temperature. This observation is novel and renders it possibleto performflthe manufacture of. oleic acid and its homologues in a very simple way. It is only necessary to separate from the naturally occurringv mixtures of unsaturated'fatty alcohols or their esters, particularly naturally occurring esters like sperm oil or arctic sperm oil the portions which are solid in the cold by known processes from the raw materials. Often, for instance, a simple freezing out process is sufficient. The residual fluid of highly unsaturated oil is then converted into a soap in the method detailed below. Decomposition of the soap with acid yields finally an oleic-acid-like mixture of fatty acids. The
product of reaction itself, or after distilling or fractionating, is an excellent mixture of unsaturated fatty acids which may be used in the refining processes of textiles, in the production of textile assistants and in all cases in which heretofore oleic acid (so-called oleine) from tallow was applied. The conversion of the naturally occurring mixtures of fatty alcohols or their-esters, e. 5., sperm oil to fatty acids of oleic-acid-like nature is performed by first separating the solid portions of the raw materials by filtration in the cold or by other suitable processes and after addition of the necessary amount of alkali metal and alkaline earth metal hydroxides or mixtures there of by gradually heating while stirring at temperatures over 200 C. advantageously between 200 to 280 C. The alkali or earth alkali hydroxides are used preferably in a small excess previously to the reaction mixture. The end of the reaction is recognized when the evolution of the hydrogen gas stops. The formed soap is decomposed with acids. By this method a mixture of unsaturated fattyacids of the type of oleic acid is obtained which not only resembles by colour, odour and physical and chemical com The process is suitably performed unstants the oleic acid obtained by the stearin' process by pressing of! the tallow but it is also like that product which is free of highly unsaturated easy inflammable and chemically unstable higher molecular weight unsaturated acids. Therefore it is suitable not only for greasing purposesbut also for the manufacture of textile soaps and textile soap preparations, for sulfonates for emulsion purposes and so on. v
The proposed method for the manufacture of valuable oleine is a new one and provides for obtaining those products from cheap raw materials not fit for food or for the manufacture of soaps, without troublesome pressure extraction or protracted fractional distillation. Therefore it is possible to make mixtures of high molecular unsaturated fatty acids in a more satisfactory way.-
The process above may also be performed by immediately submitting without previous filtration the raw materials to the fusion with alkali and then after decomposition of the formed soap separating by filtration the solid saturated fatty acids from the fluid unsaturated fatty acids of the type of oleic acid.
Example 1 500 parts by weight of technical oleyl alcohol, (iodine number as obtained by cooling down to --15 C. and filtering in a cooled press the is distilling off. The temperature is slowly raised to 276-280 C., the quantity of hydrogen split off being a measure for the progress of the reaction. As soonas the evolutionof hydrogen is over the reaction mixture is cooled down and the formed soap is decomposed by diluted sulfuric acid. An oleic acid with the iodine number of 68-70 and a content of 9697% saponifiablefat is obtained.
Example 2 500 parts by weight of sperm oil or arctic sperm oil (iodine number 85) are.worked up in the same manner as in Example 1 with 100 parts by weight of caustic soda and 25 parts by weight of water. The solid portions of the sperm oil or arctic sperm oil are separated in the manner described in Example l. 515 parts'by weight of a mixture of unsaturated fatty acids are obtained (saponification number 202, iodine number 78-80, stock point 3). The mixture is suitable generally as a substitute for the usual oleic acid.
I claim:
1. The process for the manufacture of unsaturated fatty acids which comprises separating from sperm oil the saturated portion'which is solid at low temperatures, reacting the residual fluid portion with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature above 200 C. and under super-atmospheric pressure until the esters present are saponified and alkali salts of unsaturated fatty acids are formed from com-- ponents of the esters and reacting the unsaturated fatty acid salts with a mineral acid to produceunsaturated fatty acids.
2. The process for the manufacture. of unsaturated fatty acids which comprises separating from unsaturated fatty alcohol mixtures obtained from the oils of sea animals the saturated portion which is. solid at low temperatures, reacting 3. The process for the manufacture of unsat urated fatty acids which comprises separating from mixtures of esters occurring in the oils of sea animals the unsaturated esters fluid at low temperatures, reacting the same with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature above 200 C. and under superatmospheric pressure until the esters present are -saponified and alkali salts of unsaturated fatty acids are formed from both components of the esters and reacting the unsaturated fatty acid salts with amineral acid to produce unsaturated fatty acids.
4. The process for the manufacture of unsaturated fatty acids which comprises reacting a mixture of unsaturated fatty alcohols obtained from the oils of sea animals with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature between 200 and 280 C. and under a pressure of about 5 atmospheres until the same is converted to alkali salts of unsaturated fatty acids and reacting the unsaturated fatty acid salts with a mineral acid to produce unsaturated fatty acids.
5. The process for the manufacture of unsaturated fatty acids which comprises reacting a mixture of unsaturated fatty esters obtained from the oils of sea animals with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature, between about 200 and about 280 .C. and
under a pressure of about 5 atmospheres 'until the esters present are saponified 'and'alkali salts of unsaturated fatty acids are formed from both components of the esters and reacting the unsaturated fatty acid salts with a mineral acid to produce ,unsaturated fatty acids.
6. The process for the manufacture of unsaturated fatty acids which comprises reacting material of the group consisting of unsaturated fatty alcohols and esters of unsaturated fatty alcohols with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature above 200 C. and under superatmospheric pressure until the same is converted to alkali salts of unsaturated fatty acids. p
'7. The process for the manufacture of unsaturated fatty acids which comprises reacting material of the group consisting of unsaturated fatty alcohols and esters of unsaturated fatty alcohols with alkali of the group consisting of alkali metal and alkaline earth metal hydroxides in a slight excess at a temperature between about 200 and about 280 C. and under a pressure of about 5 salts ofunsaturated fatty acids.
KARL HENN'IG.
7 CERTIFICATE or CORRECTION. Patent No. 2,159,700. May- 2 1939. KARL HENNIG.
It is hereby certified that error appears in the of the above numbered patent requiring correction as fol-lows; Page 2,'f1rst column, line 10, for "276-280 0'." read 270-280 0,; line 1 0, after "from" insert the word both; and that'the said. Letters Patent should be read with this correction therein that the same may conform to the record of the easein the Pateht Office.
Signed and sealed this printed ape cification hth da of July, A, D. 1959.-
I I 4 Henry Van Arsdal'e (Seal) Acti ng Commissioner of Patents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2159700X | 1934-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2159700A true US2159700A (en) | 1939-05-23 |
Family
ID=7987846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US54298A Expired - Lifetime US2159700A (en) | 1934-12-15 | 1935-12-13 | Process for the manufacture of unsaturated fatty acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2159700A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2640840A (en) * | 1949-10-19 | 1953-06-02 | Compania Ind | Manufacture of odorless soap from low grade oils and fats |
| US2685593A (en) * | 1951-09-04 | 1954-08-03 | Countcil Of Scient And Ind Res | Manufacture of useful compounds and products from the seed oil of mallotus philippinensis muell. arg. |
| US2801971A (en) * | 1952-06-17 | 1957-08-06 | Exxon Research Engineering Co | Manufacture of lubricating greases by the in situ alkali fusion of alcohols |
| US2871249A (en) * | 1953-04-15 | 1959-01-27 | Ruhrchemie Ag | Working up of distillation fractions containing alcohols and hydrocarbons |
| US3503896A (en) * | 1966-08-30 | 1970-03-31 | Ethyl Corp | Compositions containing soaps of monounsaturated fatty acids derived by selective hydrogenation of polyunsaturated fatty acid soaps |
-
1935
- 1935-12-13 US US54298A patent/US2159700A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2640840A (en) * | 1949-10-19 | 1953-06-02 | Compania Ind | Manufacture of odorless soap from low grade oils and fats |
| US2685593A (en) * | 1951-09-04 | 1954-08-03 | Countcil Of Scient And Ind Res | Manufacture of useful compounds and products from the seed oil of mallotus philippinensis muell. arg. |
| US2801971A (en) * | 1952-06-17 | 1957-08-06 | Exxon Research Engineering Co | Manufacture of lubricating greases by the in situ alkali fusion of alcohols |
| US2871249A (en) * | 1953-04-15 | 1959-01-27 | Ruhrchemie Ag | Working up of distillation fractions containing alcohols and hydrocarbons |
| US3503896A (en) * | 1966-08-30 | 1970-03-31 | Ethyl Corp | Compositions containing soaps of monounsaturated fatty acids derived by selective hydrogenation of polyunsaturated fatty acid soaps |
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