US2692886A - Process for improving unsaturated fatty acids or derivatives thereof - Google Patents
Process for improving unsaturated fatty acids or derivatives thereof Download PDFInfo
- Publication number
- US2692886A US2692886A US180905A US18090550A US2692886A US 2692886 A US2692886 A US 2692886A US 180905 A US180905 A US 180905A US 18090550 A US18090550 A US 18090550A US 2692886 A US2692886 A US 2692886A
- Authority
- US
- United States
- Prior art keywords
- nickel
- catalyst
- fatty acids
- derivatives
- unsaturated fatty
- 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
- 238000000034 method Methods 0.000 title claims description 32
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims description 16
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims description 14
- 239000003054 catalyst Substances 0.000 claims description 33
- 239000005864 Sulphur Substances 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 18
- 229910017052 cobalt Inorganic materials 0.000 claims description 15
- 239000010941 cobalt Substances 0.000 claims description 15
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- 150000002739 metals Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 48
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- 229910052759 nickel Inorganic materials 0.000 description 22
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000000944 linseed oil Substances 0.000 description 9
- 235000021388 linseed oil Nutrition 0.000 description 9
- 230000021615 conjugation Effects 0.000 description 7
- 238000001035 drying Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000010685 fatty oil Substances 0.000 description 4
- -1 for example Substances 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 150000001869 cobalt compounds Chemical class 0.000 description 3
- FMQXRRZIHURSLR-UHFFFAOYSA-N dioxido(oxo)silane;nickel(2+) Chemical compound [Ni+2].[O-][Si]([O-])=O FMQXRRZIHURSLR-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical compound [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000010698 whale oil Substances 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/14—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by isomerisation
Definitions
- This invention relates to a process for improving unsaturated fatty acids or derivatives thereof.
- unsaturated fatty acids or derivatives thereof can be improved by heating them in the presence of the above mentioned catalysts to a temperature not exceeding 140 C. (preferably between 100 C. and 120 C.) and that the resulting products are substantially free from the above mentioned undesirable properties. Treatment at such lower temperatures prevents the materials from acquiring a dark colour, and films from oils so treated do not stay tacky after drying. Moreover, the percentage of conjugated double bonds can be raised to a figure which is considerably higher than in the case of the known process of heating to temperatures above 170 C.
- the present invention provides a process for improving unsaturated fatty acids or derivatives thereof by heating the fatty acid or derivative to a temperature not exceeding 140 C. with a nickel or cobalt catalyst containing nickel or cobalt silicate and a small proportion of sulphur and which has been prepared by the reduction of a nickel or cobalt compound.
- the preferred temperature is between 100 C. and 120 C.
- the process of the invention is particularly useful for the treatment of fatty oils.
- oils may be processed while crude or after a preliminary treatment such as neutralisation and/or bleaching.
- the fatty oils may be drying or semi-drying oils, and may also be non-drying (Cl. 26(l--405.6)
- oils containing oleic acid or other unsaturated fatty acid radicals with a single double bond are oils containing oleic acid or other unsaturated fatty acid radicals with a single double bond.
- Other substances to which the invention can be applied are unsaturated fatty acids such as oleic acid itself and the linseed oil fatty acids, and derivatives of the unsaturated fatty acids, other than the fatty oils, and their esters other than glycerides, for example, the alkyl esters such as the ethyl esters. Mixtures of these substances and materials containing these sub stances, are also suitable for processing according to the invention.
- the process is particularly important when applied to oils used in the paint industry, since it enables the production of oils which retain their light colour and which have acquired a high content of conjugated double bonds, as a result of which the oils will polymerise rapidly and dry quickly to waterproof non-tacky films.
- the specific gravity, viscosity and free fatty acid content of substances treated by the process of the invention remain practically unchanged.
- the double bonds change position.
- the cis form of the compound is converted into the trans form.
- the most important result of this change of position of the double bonds is the formation of conjugated double bonds.
- unsaturated fatty acids or their derivatives with a single double bond for example, oleic acid or its esters
- the conversion of the cisinto the trans-form causes a rise in melting point, which is of importance in the manufacture of margarine and other edible fats.
- the process of the invention may be carried out, with nickel or cobalt catalysts containing a small proportion of sulphur and which have been prepared by the reduction of a precipitate containing nickel or cobalt silicate.
- nickel or cobalt catalysts are usually prepared by prepicitating nickel or cobalt in the form of an insoluble compound from a solution of the metal salt, for example nickel or cobalt sulphate, in the presence of a material capable of forming a silicate with a part of the precipitate, for example, diatomaceous earth or water glass. The prepicitate is separated by filtering and washing.
- the sulphur content can be imparted to the catalyst in various ways at many stages in its preparation, for example by treatingv the precipitate formed with alkali with a solution of a sulphur-containing nickel or cobalt compound such as, for example, nickel sulphate or by mix-- ing the filtered and dried precipitate with sulphur or a sulphur compound. before reduction.
- a sulphur-containing nickel or cobalt compound such as, for example, nickel sulphate
- the sulphur content can be imparted to the catalyst subsequent to its preparation, for example, by treating the reduced catalyst with hydrogen sulphide or by using the reduced catalyst to hydrogenate a sulphur-containing oil.
- the most suitable proportion of sulphur is between 1 and 10% of the metal by weight.
- nickel catalyst in carrying out the process of the invention and preferably such a catalyst should contain about 4% of sulphur.
- the catalysts used in the process of the invention may contain other conventional ingredients such as carriers.
- the time of treatment depends on various factors such as the actual temperature employed, the nature of the catalyst, the desired isomerisation and the like. Usually, the treatment, is continued for from about 2 to 8 hours, although a shorter or longer period of treatment will often produce good results, depending on the circumstances. The best way of determining the most suitable period is to carry out an experimental test in each particular case.
- Lovibond Colour index of the product was measured in a one-inch cuvette; in Examples 3 and 5 it was. measured in a one-inchcell- 286 grammes of nickel sulphate (NiSOr'lHzO) was dissolved in water to 600 00s.; 30 grammes of diatomaceous earth was added to this solution and while stirring at boiling temperature 350 grammes sodium carbonate (NazCOa.l0I-I2O) dissolved in water to 720 ccs. was then slowly added over a period of, 1 hours. Boiling for a further short periodof' half-an-hour was followed by filtering and the precipitate was washed with water until no more cloudiness was observed with barium chloride solution.
- NiSOaTI-IzO nickel sulphate
- a quantity of the catalyst prepared. in this way was added to neutralized and bleached linseed oil, so that nickel to. a quantity of 10% by weight of oil was present. Quantities of this mixture were heated. while stirring in a carbon. dioxide atmosphere to various temperatures for four hours, and the following values were obtained for increase in refractive index, percentage of fatty acid groups with conjugated double bonds and Lovibond colour:
- Example 3 The following increases in melting point were obtained in a similar way with oils having a.
- Examples 1 to 3 show clearly that the best results are obtained at about 100 C. Specific gravity, viscosity and free fatty acid content hardly change at this temperature during isomerization, in contrast to treatment at 180 C.
- Example 4 Linseed oil fatty acids are processed in the same way as in Example 1 for 1 hour at 100 C.
- the increase in refractive index was 0.0120, and the colour was green, in consequence of dissolved nickel. This green colour was removed by sulphuric acid treatment. Linseed oil, treated for 1 hour at 100 C. likewise displayed an increase in refractive index of 0.0120.
- Example 5 The methyl esters of linseed oil fatty acids were treated in the same way as in Example 1 for 4 hours at 100 C. Increase in refractive index was 0.0155 and percentage conjugation 55, namely exactly the same as for linseed oil (compare Example 1), Lovibond colour was yellow 40, red 4.
- Example 6 Methyloleate was treated in the same way as in Example 1 for 4 hours at various temperatures, after which the free fatty acids were removed by saponification and soap splitting.
- Example 7 Linseed oil was treated in the same way as in Example 1, but with only 4% of catalyst calculated on the basis of nickel to oil for 4 hours at varying temperatures.
- a process for improving a substance selected from the group consisting of unsaturated fatty acids and derivatives thereof which process comprises heating said substance in :an inert atmosphere to a temperature not exceeding 140 C. with a catalyst selected from the group consisting of cobalt and nickel, and containing a silicate of one of said metals and a small proportion of sulphur said catalyst having been prepared by reduction of a compound of one of said metals.
- a process for improving a substance selected from a group consisting of unsaturated fatty acids, and derivatives thereof which process comprises heating said substance in an inert atmosphere to a temperature between C. and C. with a catalyst selected from the group consisting of cobalt and nickel and containing a silicate of one of said metals and a small proportion of sulphur, said catalyst having been prepared by reduction of a compound of one of said metals.
- a process for improving a substance selected from the group consisting of unsaturated fatty acids and derivatives thereof which process comprises heating said substance in an inert atmosphere .to a temperature not exceeding C. with a catalyst selected from the group consisting of cobalt and nickel and containing a silicate of one of said metals and a small proportion of sulphur, said catalyst having been prepared by subjecting to a reduction treatment a mixture consisting of said silicate with a compound of one of said metals which compound has been precipitated from an aqueous solution of a soluble salt of one of said metals.
- a process for improving a substance selected from the group consisting of unsaturated fatty acids and derivatives thereof which process comprises heating said substance in an inert atmosphere to a temperature not exceeding 140 C. with a nickel catalyst containing nickel silicate and a small proportion of sulphur said catalyst having been prepared by reduction of a nickel compound.
- a process for improving a fatty oil which comprises heating said oil in an inert atmosphere to a temperature not exceeding 140 C. with an amount calculated as metal between 5 to 10% by weight of the amount of oil of a catalyst selected from the group consisting of cobalt and nickel, and containing a silicate of one of said metals and a small proportion of sulphur, said catalyst having been prepared by reduction of a compound of one of said metals.
- a process for conjugating a substance selected from the group consisting of unsaturated fatty acids, and derivatives thereof which process comprises heating said substance in an inert atmosphere to a temperature not exceeding 140 C. and for such a time until maximum conjugation is attained with a catalyst selected from the group consisting of cobalt and nickel, and containing a silicate of one of said metals and a small proportion of sulphur, said catalyst having been prepared by reduction of a compound of one of said metals.
- a process of improving linseed oil which comprises heating said oil in an inert atmosphere to about 100 C. with an amount calculated as metal by weight of the amount of oil, of a nickel catalyst containing 4.5% by weight of sulphur and which has been prepared by reduction of a 3; Name Date Stejskal' May 15, 1951 Number precipitate containing nickel silicate which nickel silicate has been formed; by heating a suspension of precipitated nickel carbonate in water with diatomaceous earth.
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL148435A NL78104C (en)) | 1949-08-31 | 1949-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2692886A true US2692886A (en) | 1954-10-26 |
Family
ID=63103723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US180905A Expired - Lifetime US2692886A (en) | 1949-08-31 | 1950-08-22 | Process for improving unsaturated fatty acids or derivatives thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US2692886A (en)) |
| AT (1) | AT178151B (en)) |
| AU (1) | AU149990B1 (en)) |
| CH (1) | CH305123A (en)) |
| DE (1) | DE883892C (en)) |
| FR (1) | FR1039559A (en)) |
| GB (1) | GB693981A (en)) |
| NL (1) | NL78104C (en)) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274119A (en) * | 1963-03-01 | 1966-09-20 | Lever Brothers Ltd | Transparent soap bar |
| US4203911A (en) * | 1978-07-24 | 1980-05-20 | Scm Corporation | Process for conjugating unconjugated unsaturation of fatty acids or esters thereof |
| US4271066A (en) * | 1979-11-05 | 1981-06-02 | Arakawa Kagaku Kogyo Kabushiki Kaisha | Process for disproportionating rosin, poly-unsaturated fatty acids and mixtures thereof |
| CN114480883A (zh) * | 2021-12-16 | 2022-05-13 | 成都先进金属材料产业技术研究院股份有限公司 | 一种镍离子协同去除钒溶液中硅和铬以制备高纯五氧化二钒的方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746979A (en) * | 1951-06-14 | 1956-05-22 | Lever Brothers Ltd | Process for isomerizing unsaturated fatty acids or derivatives thereof |
| DE1089751B (de) * | 1954-02-05 | 1960-09-29 | Unilever Nv | Verfahren zum Isomerisieren von ungesaettigten Fettsaeuren oder ihren Estern |
| DE954958C (de) * | 1954-06-30 | 1956-12-27 | Bayer Ag | Verfahren zur Umlagerung von ª‰-Methylenglutarsaeuredinitril in ª‰-Methylglutaconsaeuredinitril |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468799A (en) * | 1943-10-20 | 1949-05-03 | Lever Brothers Ltd | Hydrogenating fat |
| US2553429A (en) * | 1951-05-15 | Semidrying oils |
-
1949
- 1949-08-31 NL NL148435A patent/NL78104C/xx active
-
1950
- 1950-08-08 GB GB19719/50A patent/GB693981A/en not_active Expired
- 1950-08-16 AU AU36327/50A patent/AU149990B1/en not_active Expired
- 1950-08-22 US US180905A patent/US2692886A/en not_active Expired - Lifetime
- 1950-08-29 DE DEL3467A patent/DE883892C/de not_active Expired
- 1950-08-30 CH CH305123D patent/CH305123A/de unknown
- 1950-08-31 FR FR1039559D patent/FR1039559A/fr not_active Expired
- 1950-08-31 AT AT178151D patent/AT178151B/de active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2553429A (en) * | 1951-05-15 | Semidrying oils | ||
| US2468799A (en) * | 1943-10-20 | 1949-05-03 | Lever Brothers Ltd | Hydrogenating fat |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274119A (en) * | 1963-03-01 | 1966-09-20 | Lever Brothers Ltd | Transparent soap bar |
| US4203911A (en) * | 1978-07-24 | 1980-05-20 | Scm Corporation | Process for conjugating unconjugated unsaturation of fatty acids or esters thereof |
| US4271066A (en) * | 1979-11-05 | 1981-06-02 | Arakawa Kagaku Kogyo Kabushiki Kaisha | Process for disproportionating rosin, poly-unsaturated fatty acids and mixtures thereof |
| CN114480883A (zh) * | 2021-12-16 | 2022-05-13 | 成都先进金属材料产业技术研究院股份有限公司 | 一种镍离子协同去除钒溶液中硅和铬以制备高纯五氧化二钒的方法 |
| CN114480883B (zh) * | 2021-12-16 | 2023-11-21 | 成都先进金属材料产业技术研究院股份有限公司 | 一种镍离子协同去除钒溶液中硅和铬以制备高纯五氧化二钒的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL78104C (en)) | 1955-06-15 |
| DE883892C (de) | 1953-07-23 |
| FR1039559A (fr) | 1953-10-08 |
| AU149990B1 (en) | 1950-10-19 |
| GB693981A (en) | 1953-07-08 |
| AT178151B (de) | 1954-04-10 |
| CH305123A (de) | 1955-02-15 |
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