US3471536A - Process for improving fatty acids - Google Patents
Process for improving fatty acids Download PDFInfo
- Publication number
- US3471536A US3471536A US602560A US3471536DA US3471536A US 3471536 A US3471536 A US 3471536A US 602560 A US602560 A US 602560A US 3471536D A US3471536D A US 3471536DA US 3471536 A US3471536 A US 3471536A
- Authority
- US
- United States
- Prior art keywords
- fatty acid
- soap
- acid
- distillation
- amino compound
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 title description 66
- 239000000194 fatty acid Substances 0.000 title description 66
- 229930195729 fatty acid Natural products 0.000 title description 66
- 150000004665 fatty acids Chemical class 0.000 title description 66
- 238000000034 method Methods 0.000 title description 27
- 230000008569 process Effects 0.000 title description 25
- 239000000344 soap Substances 0.000 description 46
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 31
- -1 amino compound Chemical class 0.000 description 25
- 238000004821 distillation Methods 0.000 description 22
- 239000002253 acid Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- 239000000047 product Substances 0.000 description 16
- 150000001728 carbonyl compounds Chemical class 0.000 description 12
- 239000012535 impurity Substances 0.000 description 12
- 125000005456 glyceride group Chemical group 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 235000019483 Peanut oil Nutrition 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009874 alkali refining Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000312 peanut oil Substances 0.000 description 6
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 6
- 229940067157 phenylhydrazine Drugs 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
- 239000003240 coconut oil Substances 0.000 description 5
- 235000019864 coconut oil Nutrition 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000003139 primary aliphatic amines Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 4
- 235000021588 free fatty acids Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241001620634 Roger Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
- C11C1/10—Refining by distillation
- C11C1/103—Refining by distillation after or with the addition of chemicals
Definitions
- Edible oils and fats in the crude state always contain a certain amount of free fatty acid which has to be removed to prepare a neutral glyceride oil which can be used for the preparation of fatty foodstuffs.
- the most common method of removing the fatty acid is by alkali-refining in which the crude glyceride oil is neutralised with aqueous alkali, for instance caustic soda.
- aqueous alkali for instance caustic soda.
- soap stock is separated from the neutral glyceride oil by decantation or centrifugation, and contains the neutralised free fatty acid as well as other impurities and a small amount of glyceride oil.
- the latter is acidified, for example, with sulphuric acid, and the precipitated acid oil is separated.
- the acid oil is usually subjected to a further treatment to hydrolyse the glycerides still present into fatty acid and glycerol, and this is normally carried out by heating the acid oil to a high temperature in an autoclave in the presence of water.
- the separated acid is then distilled to separate volatile acid from nonvolatile impurities which are concentrated in a residual fraction.
- the acid thus obtained is commonly called a technical fatty acid.
- the distillation process can be modified to prepare, for example, specific fractions containing fatty acid of a certain chain length or in which highly volatile constituents are removed which are not very stable and affect soap made from the fatty acid.
- the technical fatty acid When the technical fatty acid is to be used in the manufacture of toilet soap it is important to obtain from the crude fatty acid a high proportion of a fraction which is suitable for the preparation of good quality soap.
- the crude vegetable or animal glyceride oils from which technical fatty acids are prepared also contain small proportions of impurities which can be generally designated by the terms oxidation products, oxidised fatty acids, and carbonyl derivatives, which generally result from the action of oxygen on the free fatty acids or on the oils.
- oxidising agents such as a hypochlorite, a permanganate or even ozone
- adsorption agents such as silica gel, active carbon and a bleaching earth.
- the invention provides a process for improving a fatty acid containing impurities giving rise to colour instability when soap is made from it, in which the fatty acid is contacted with an amino compound that is a hydrazine having a free amino group or is a primary aliphatic amine of from 12 to 18 carbon atoms in the molecule, and reaction products of the amino compound and the impurities are subsequently removed.
- the reaction products are removed by distillation of the fatty acid.
- the amino-compounds to be used can be generally represented by the formula R-NH in which R represents either an amino group in which one or both of the hydrogen atoms can be replaced by substituted or unsubstituted aliphatic or aromatic hydrocarbon radicals, especially substituted or unsubstituted alkyl, cycloalkyl or aryl groups, or R represents an aliphatic hydrocarbon radical containing from 12 to 18 carbon atoms, which can be saturated or unsaturated.
- the amino compounds of the first group are hydrazine and its monoand di-substitution derivatives, for instance phenylhydrazine, while the compounds of the second group are primary aliphatic amines, especially alkylamines, for instance stearylamine and lauryla-mine, and alkenylamines, for instance oleylamine.
- Hydrazine can be used in hydrated form, for instance as an aqueous solution of 20 to 30% concentration.
- the hydrazine compound contains from 1 to 30 carbon atoms, and especially from 1 to 15 carbon atoms in the molecule.
- a preferred group of amino compounds are those selected from the group consisting of hydrazine, phenylhydrazine and primary aliphatic amines having from 12 to 18 carbon atoms.
- the improvement of the quality of the fatty acids can be effected by stirring the fatty acid to be treated with a small quantity of the amino compound at a temperature which can be adapted to the type of fatty acid as well as to the type of amino compound.
- the amount of amino compound which is suitable depends on the conditions of treatment and the type and quality of the fatty acid to be treated, but in general it is between 0.01 and 5% by weight of the fatty acid to be treated, the best results being obtained when the amount of amino compound is between 0.05 and 1% by weight. It is preferable to combine the treatment with the distillation process itself.
- the fatty acid and the amino compound are brought together at a temperature substantially below the decomposition temperature of the amino compound, and the temperature of the acid is then raised to boiling point, as in distillation.
- the fatty acid is contacted with the amino compound at a temperature of from 40 to 160 C., and especially from 50 to 90 C. Conveniently the temperature of the fatty acid is then progressively increased until the distillation temperature, normally between 180 and 250 C., is reached.
- the oxidation products that are chemically combined with the free amino group of the amino compound are substantially removed during distillation, while the reduced oxidation products are harmless and can be left in the final product.
- the above procedure has the advantage that by combining the contacting step with the distillation it is not necessary to introduce a separate treatment step in the preparation of high-quality fatty acids suitable for the production of stable soaps.
- acid materials of inferior quality that are unsuitable for the preparation of soaps, can be improved by the process of the invention.
- Such acid materials comprise, for example, the product obtained by distilling the hydrolysed residue from the first distillation of crude fatty acid.
- Such a material is unsuitable for the preparation of soaps because soaps made starting with it become rapidly coloured, but when it is re-distilled in the presence of a small amount of the amino compound, a fatty acid can be obtained in a yield of about 80-90%, that can immediately be used for the preparation of stable soaps.
- the process of the invention can also be carried out after the normal distillation used in making technical fatty acids, but it is then necessary to remove substantially the reaction products of the oxidation products and the amino compounds, which can be done by agitating the treated fatty acids with a small amount of a bleaching earth at a temperature below 100 0., followed by filtration. Active carbon or silica gel in amounts of between 1 and 3% can also be used.
- Example 1 To a crude fatty acid of groundnut oil, obtained by hydrolysis of an acid oil obtained as a by-product during the neutralisation of crude groundnut oil with caustic soda, was added 0.4% by weight of a 24% aqueous solution of hydrazine hydrate; the mixture was stirred at 60 C. and subjected to distillation under normal conditions used in the production of a technical fatty acid.
- the temperature during the distillation was 225-230 C., the pressure 3-4 mm. of mercury and a conventional vacuum distillation column (Lurgi column) Was used, the fatty acid being introduced in the middle of the column after preliminary heating.
- the residue was recovered at the bottom and the improved fraction was recovered in the upper part of the apparatus, the distillation treatment being continued until the yield of the upper fraction was 80%.
- the acid obtained was converted to soap with potassium hydroxide.
- the colour of the soap was determined by means of a spectrophotometer (Jobin Yvon type) at a wave length of 470 millimicrons with a cell of 4 cm., using a 5% aqueous alcoholic solution of the soap.
- the optical density was determined as a measure of the colour of the soap, a value of about 0.200 indicating that the fatty acid is unsuitable for the preparation of soap while a value below 0.100 generally indicates an excellent quality of fatty acid.
- the presence of carbonyl compounds in the treated fatty acid was determined by thin layer chromatography.
- the adsorbent used was silica gel G, the film had a thickness of 250 microns and was activated for 2 hours at a temperature of 110 C.
- the mobile phase consisted of a mixture of light petroleum and ether (20%), containing a small amount of acetic acid, and the elution front was 15 cm. long.
- the chromatogram was treated with a 0.4% solution of 2,4-dinitrophenylhydrazine in 2 N hydrochloric acid in order to develop any spots due to the presence of carbonyl compounds: such spots have a yellow, orange or yellow-orange colour.
- Example 2 A crude coconut oil fatty acid obtained by the alkalirefining process was contacted under the same conditions as in Example 1 with 0.4% by weight of a 24% aqueous solution of hydrazine hydrate, and the product distilled to a yield of 80%, converted to soap and tested as before.
- the soap colour was 0.060 and no carbonyl compounds were detected.
- the same fatty acid which had been submitted to the normal distillation up to a yield of 80% without using hydrazine gave a soap of colour 0.120 and the presence of carbonyl compounds was detected.
- Example 3 A crude fatty acid of groundnut oil obtained by the alkali-refining process was treated as described in Example l, but using 0.3% by weight of phenylhydrazine instead of the hydrazine hydrate, and the product converted to soap and tested as before. The soap had a colour of 0.090 and no carbonyl compounds were detected. The process was repeated without the use of phenylhydrazine; the product gave a soap of colour 0.120 and carbonyl compounds were detected.
- Example 4 A coconut oil fatty acid obtained by hydrolysis of the residue of the distillation of a technical coconut oil fatty acid was treated as in Example 1, but using 0.5% by weight of a 24% aqueous solution of hydrazine hydrate, and continuing distillation to a yield of and soap was prepared and tested as before.
- the colour of the soap obtained was 0.100, while the colour of the soap obtained with the fatty acid distilled without the hydrazine treatment was 0.450.
- the first product did not contain carbonyl compounds, while the second product gave carbonyl spots on the chromatogram.
- Example 5 A crude coconut oil fatty acid obtained by acid hydrolysis of an acid oil was distilled in the presence of 0.1% of hydrazine by weight under the same conditions as described in Example 1, except that distillation was continued to a yield of 85 and the product was converted to soap and tested as before. The colour of the soap was 0.070. The same material distilled without hydrazine treatment gave a soap of colour 0.100 and showed traces of carbonyl compounds, which were absent from the product obtained using hydrazine.
- Example 6 A groundnut oil fatty acid obtained by hydrolysis of residual fatty material from a distillation of a technical fatty acid, was contacted with 0.1% by weight of hydrazine, distilled, and converted to soap which was tested, all as in Example 1.
- the colour of the soap was 0.040, and no carbonyl compounds were detected; when the same material was treated without hydrazine, the colour of the soap obtained was 0.700, and the soap showed traces of carbonyl compounds.
- Example 7 A crude groundnut oil fatty acid obtained by hydrolysis of an acid oil was treated with 0.6% by weight of laurylamine and distilled, converted into soap, and the soap tested as in Example 1. The colour of the soap obtained was 0.065, while the same fatty acid distilled without addition of laurylamine gave a soap of colour 0.150.
- Example 8 A crude coconut oil fatty acid obtained by the alkalirefining process is distilled to a yield of 80% and to the distillate at 75 C. is added 0.1% by weight of hydrazine hydrate. The mixture is stirred and 1.5% by weight of active carbon is added and the mixture again stirred. The active carbon is then removed by filtration, leaving an acid of improved quality for soap manufacture.
- a process for improving a fatty acid containing impurities giving rise to color instability when soap is made from it which comprises contacting the fatty acid with from 0.01 to 5% of its Weight of an amino compound selected from the group consisting of hydrazine, phenylhydrazine and a primary aliphatic amine having from 12 to 18 carbon atoms, and removing the fatty acid from the reaction products of the amino compound and the impurities.
- the fatty acid is one which has been obtained by the distillation of a hydrolysed acid oil from a soap stock prepared by alkali-refining a crude glyceride oil.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR44209A FR1475711A (fr) | 1965-12-29 | 1965-12-29 | Procédé pour améliorer les acides gras utilisés dans la fabrication du savon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3471536A true US3471536A (en) | 1969-10-07 |
Family
ID=8597221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US602560A Expired - Lifetime US3471536A (en) | 1965-12-29 | 1966-12-19 | Process for improving fatty acids |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3471536A (enrdf_load_html_response) |
| AT (1) | AT271686B (enrdf_load_html_response) |
| BE (1) | BE691916A (enrdf_load_html_response) |
| DE (1) | DE1617036A1 (enrdf_load_html_response) |
| FR (1) | FR1475711A (enrdf_load_html_response) |
| GB (1) | GB1163966A (enrdf_load_html_response) |
| LU (1) | LU52697A1 (enrdf_load_html_response) |
| NL (1) | NL6618161A (enrdf_load_html_response) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2939242A1 (de) | 1978-09-27 | 1980-04-17 | Nippon Oils & Fats Co Ltd | Verfahren zum reinigen von fettsaeuren |
| JPS55160742A (en) * | 1979-05-29 | 1980-12-13 | Nippon Oil & Fats Co Ltd | Purification of fatty acid |
| DE19531806C1 (de) * | 1995-08-30 | 1997-04-10 | Henkel Kgaa | Verfahren zur schonenden Destillation von Fettsäuren |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2126334A (en) * | 1936-05-25 | 1938-08-09 | Shell Dev | Process for refining vegetable oils and the like |
| US2581452A (en) * | 1947-03-29 | 1952-01-08 | Kellogg M W Co | Dehydration of organic acids |
| US2664430A (en) * | 1950-11-10 | 1953-12-29 | Colgate Palmolive Peet Co | Fatty acid treatment |
-
1965
- 1965-12-29 FR FR44209A patent/FR1475711A/fr not_active Expired
-
1966
- 1966-12-19 US US602560A patent/US3471536A/en not_active Expired - Lifetime
- 1966-12-22 GB GB57482/66A patent/GB1163966A/en not_active Expired
- 1966-12-24 NL NL6618161A patent/NL6618161A/xx unknown
- 1966-12-28 DE DE19661617036 patent/DE1617036A1/de active Pending
- 1966-12-28 LU LU52697D patent/LU52697A1/xx unknown
- 1966-12-28 BE BE691916D patent/BE691916A/xx unknown
- 1966-12-28 AT AT1191966A patent/AT271686B/de active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2126334A (en) * | 1936-05-25 | 1938-08-09 | Shell Dev | Process for refining vegetable oils and the like |
| US2581452A (en) * | 1947-03-29 | 1952-01-08 | Kellogg M W Co | Dehydration of organic acids |
| US2664430A (en) * | 1950-11-10 | 1953-12-29 | Colgate Palmolive Peet Co | Fatty acid treatment |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2939242A1 (de) | 1978-09-27 | 1980-04-17 | Nippon Oils & Fats Co Ltd | Verfahren zum reinigen von fettsaeuren |
| JPS55160742A (en) * | 1979-05-29 | 1980-12-13 | Nippon Oil & Fats Co Ltd | Purification of fatty acid |
| DE19531806C1 (de) * | 1995-08-30 | 1997-04-10 | Henkel Kgaa | Verfahren zur schonenden Destillation von Fettsäuren |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1617036A1 (de) | 1971-03-25 |
| LU52697A1 (enrdf_load_html_response) | 1968-08-05 |
| FR1475711A (fr) | 1967-04-07 |
| AT271686B (de) | 1969-06-10 |
| BE691916A (enrdf_load_html_response) | 1967-06-28 |
| NL6618161A (enrdf_load_html_response) | 1967-06-30 |
| GB1163966A (en) | 1969-09-10 |
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