CN1640874A - Method for preparing water-base vitamin E - Google Patents
Method for preparing water-base vitamin E Download PDFInfo
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- CN1640874A CN1640874A CN 200410016032 CN200410016032A CN1640874A CN 1640874 A CN1640874 A CN 1640874A CN 200410016032 CN200410016032 CN 200410016032 CN 200410016032 A CN200410016032 A CN 200410016032A CN 1640874 A CN1640874 A CN 1640874A
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 title claims abstract description 99
- 229930003427 Vitamin E Natural products 0.000 title claims abstract description 49
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 239000011709 vitamin E Substances 0.000 title claims abstract description 49
- 229940046009 vitamin E Drugs 0.000 title claims abstract description 49
- 235000019165 vitamin E Nutrition 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 238000001953 recrystallisation Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 10
- 239000012429 reaction media Substances 0.000 claims abstract description 7
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- -1 polyoxyethylene Polymers 0.000 claims description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 8
- 238000000967 suction filtration Methods 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000012970 tertiary amine catalyst Substances 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 150000003900 succinic acid esters Chemical class 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005554 pickling Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000047 product Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 229920000151 polyglycol Polymers 0.000 abstract 2
- 239000010695 polyglycol Substances 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- IELOKBJPULMYRW-NJQVLOCASA-N D-alpha-Tocopheryl Acid Succinate Chemical compound OC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C IELOKBJPULMYRW-NJQVLOCASA-N 0.000 abstract 1
- 229940099418 d- alpha-tocopherol succinate Drugs 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 229960005137 succinic acid Drugs 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 description 16
- 238000003756 stirring Methods 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- 208000033382 Rare hepatic disease Diseases 0.000 description 1
- 206010047631 Vitamin E deficiency Diseases 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Abstract
The present invention relates to the preparation of water soluble vitamin E, and is especially the preparation process of vitamin E polyglycol succinate. The preparation process includes the follow reactions: a) the tertiary amine catalyzed reaction of vitamin E and succinic acid or succinic anhydride in the weight ratio of 1 to 0.10-0.50 and dissolved in reaction medium, acid washing after reaction and water washing; and b) the acid catalyzed reaction of vitamin E succinate obtained in the last step and polyglycol in the weight ratio of 1 to 0.5-3.0 and dissolved in solvent, recovery of solvent after reaction, re-crystallization in solvent, sucking filtration and drying to obtain ultimate product. The said preparation process is simple, produces no side product, has easy separation and purification of the product, low production cost and high product quality, and is suitable for industrial production.
Description
Technical field
The invention belongs to chemical field, specifically a kind of preparation method of watermiscible vitamin E.
Background technology
Vitamin-E has another name called tocopherol, and it all has material impact to the reproductive function of human body, anti-oxidant and lipid metabolism, and vitamin E deficiency will give rise to diseases.Because traditional vitamin-E mostly is fat-soluble greatly, on using, just be subjected to certain restriction, and watermiscible vitamin E can dissolve in water fully, can make different formulations, can improve the bioavailability of vitamin-E greatly, easier being absorbed by the body, so watermiscible vitamin E plays an important role for suffering from rare hepatic diseases such as bile children that stop up and the crowd who suffers from the dyspoietic serious hepatic diseases of bile.Watermiscible vitamin E also can be used widely in food such as jelly, beverage (particularly transparent beverage), dairy products in addition.Vitamin-E is modified through certain structure, just can produce watermiscible vitamin E, vitamin E polyethylene glycol succinic acid ester (hereinafter to be referred as TPGS) is exactly a kind of in the watermiscible vitamin E, the preparation method who does not also occur relevant TPGS in the present document, therefore as how simple technology, the synthetic high-quality TPGS of lower cost is subject to the people's attention.
Summary of the invention
The technical assignment of technical problem to be solved by this invention and proposition is the defective that overcomes above-mentioned prior art, and a kind of preparation method of watermiscible vitamin E is provided, with simple technology and the lower original synthetic high-quality TPGS that becomes.
Technical scheme of the present invention is such: a kind of preparation method of watermiscible vitamin E, it is characterized in that reactions steps is as follows: a) vitamin-E and succsinic acid or succinyl oxide are 1 by weight: (0.10～0.50) is dissolved in the reaction medium, add tertiary amine and carry out catalyzed reaction, reaction is after pickling, washing, VE-succinate; B) VE-succinate that is obtained by step a and polyoxyethylene glycol in molar ratio 1: (0.5～3.0) is dissolved in the solvent, adding catalyst acid reacts, solvent is reclaimed in the reaction back, adds the recrystallization solvent recrystallization afterwards, through suction filtration, the dry final product vitamin E polyethylene glycol succinic acid ester that gets.This preparation method provides a kind of watermiscible vitamin E, has improved the bioavailability of vitamin-E greatly, easier being absorbed by the body; With the product purity height (〉=90.0%) that this method obtains, the solubleness in water is big.Raw material of the present invention can be a synthesising complex E, it also can be natural VE, therefore TPGS is divided into natural type TPGS and synthesis type TPGS again, and wherein the maxima solubility in water of natural type TPGS is about 20%, and the maxima solubility in the water of synthesis type TPGS is about 10%.
The preparation method of described a kind of watermiscible vitamin E, 20～80 ℃ of the temperature of reaction of step a, reaction times is 1～6 hour, and the weight ratio of vitamin-E and reaction medium is 1: (0.5～10.0), the mol ratio of vitamin-E and tertiary amine catalyst are 1: (0.1～2.5).
The preparation method of described a kind of watermiscible vitamin E, the reaction medium that step a adopts is toluene, acetone, butanone, hexane, hexanaphthene or sherwood oil.
The preparation method of described a kind of watermiscible vitamin E, the tertiary amine catalyst that step a adopts is triethylamine, Tetramethyl Ethylene Diamine or Dimethylamino pyridine.
The preparation method of described a kind of watermiscible vitamin E, the temperature of reaction of step b is 30～150 ℃, reaction times is 1～10 hour, and the weight ratio of VE-succinate and solvent is 1: (0.5～10.0), the mol ratio of vitamin-E and catalyst acid are 1: (0.5～5.0).
The preparation method of described a kind of watermiscible vitamin E, the solvent that step b adopts is toluene, acetone, butanone, hexane, hexanaphthene or tetrahydrofuran (THF).
The preparation method of described a kind of watermiscible vitamin E, the catalyst acid that step b adopts is sulfuric acid, phosphoric acid or p-methyl benzenesulfonic acid.
The recrystallization solvent that the preparation method of described a kind of watermiscible vitamin E, step b adopt is alcohols or ether compound, recrystallization temperature-5～20 ℃; Alcohol compound is methyl alcohol, ethanol, Virahol or isopropylcarbinol, and ether compound is ether or isopropyl ether.
The invention provides a kind of preparation method of watermiscible vitamin E, have following beneficial effect: the TPGS that makes has improved the bioavailability of vitamin-E greatly, easier being absorbed by the body; Synthesis technique of the present invention is simple, be difficult for to produce by product, and separation and purification of products is convenient, and production cost is low and quality product height (purity 〉=90.0%) is suitable for suitability for industrialized production.
Embodiment
Embodiment 1: the synthesising complex E that takes by weighing 105 grams 95.0%, 25 gram succinyl oxides, 10 gram Dimethylamino pyridines, 200ml toluene was put into three-necked bottle, 30 ℃ of following stirring reactions 2 hours, after reaction finishes, add dilute sulphuric acid, distilled water wash to neutral, keep toluene layer, behind the recovery toluene, add the 500ml tetrahydrofuran (THF), 200 gram polyoxyethylene glycol, 20 gram sulfuric acid reacted 4 hours down at 40 ℃, after reaction finishes, reclaim tetrahydrofuran (THF), add ethanol and stir the back at 0 ℃ of frozen recrystallization, suction filtration, the dry 201 gram TPGS that get, purity is 95.8%.
Embodiment 2: the synthesising complex E that takes by weighing 105 grams 95.0%, 30 gram succinyl oxides, 10 gram triethylamines, the 200ml sherwood oil was put into three-necked bottle, 40 ℃ of following stirring reactions 3 hours, after reaction finishes, add dilute sulphuric acid, distilled water wash to neutral, keep the ether layer, behind the recovery sherwood oil, add 600ml toluene, 200 gram polyoxyethylene glycol, 20 gram phosphoric acid reacted 5 hours down at 100 ℃, after reaction finishes, reclaim toluene, add ethanol and stir the back at 0 ℃ of frozen recrystallization, suction filtration, the dry 228 gram TPGS that get, purity is 95.0%.
Embodiment 3: the synthesising complex E that takes by weighing 105 grams 95.0%, 25 gram succinyl oxides, 10 gram Tetramethyl Ethylene Diamines, 200ml acetone, put into three-necked bottle, 50 ℃ of following stirring reactions 4 hours, after reaction finishes, add the 600ml hexane, add dilute sulphuric acid, distilled water wash to neutral, keep hexane layer, add 150 gram polyoxyethylene glycol, 20 gram tosic acid, reacted 6 hours down at 60 ℃, after reaction finishes, reclaim hexane, add ether and stir the back at 0 ℃ of frozen recrystallization, suction filtration, the dry 231 gram TPGS that get, purity is 93.4%.
Embodiment 4: the natural VE that takes by weighing 115 grams 87.0%, 40 gram succinyl oxides, 20 gram Dimethylamino pyridines, 500ml toluene, put into three-necked bottle, 50 ℃ of following stirring reactions 5 hours, after reaction finishes, add dilute sulphuric acid, distilled water wash to neutral, keep toluene layer, add 250 gram polyoxyethylene glycol, the sulfuric acid of 20 grams reacted 7 hours down at 90 ℃, after reaction finishes, reclaim toluene, add isopropyl ether and stir the back at 0 ℃ of frozen recrystallization, suction filtration, the dry 257 gram TPGS that get, purity is 95.9%.
Embodiment 5: the synthesising complex E that takes by weighing 105 grams 95.0%, 40 gram succinyl oxides, 20 gram triethylamines, the 200ml hexane, put into three-necked bottle, 50 ℃ of following stirring reactions 6 hours, after reaction finishes, add dilute sulphuric acid, distilled water wash to neutral, reclaim hexane, add 75 gram polyoxyethylene glycol, the phosphoric acid of 20 grams, the 500ml butanone, reacted 6 hours down at 70 ℃, after reaction finishes, reclaim butanone, add methyl alcohol and stir the back at 0 ℃ of frozen recrystallization, suction filtration, the dry 131 gram TPGS that get, purity is 95.1%.
Embodiment 6: the synthesising complex E that takes by weighing 105 grams 95.0%, 40 gram succinyl oxides, 20 gram Tetramethyl Ethylene Diamines, the 300ml hexane, put into three-necked bottle, 50 ℃ of following stirring reactions 4 hours, after reaction finishes, add dilute sulphuric acid, distilled water wash to neutral, keep hexane layer, add 100 gram polyoxyethylene glycol, the tosic acid of 20 grams reacted 5 hours down at 60 ℃, after reaction finishes, reclaim hexane, add ether and stir the back at 0 ℃ of frozen recrystallization, suction filtration, the dry 145 gram TPGS that get, purity is 95.5%.
Claims (9)
1, a kind of preparation method of watermiscible vitamin E, it is characterized in that reactions steps is as follows: a) vitamin-E and succsinic acid or succinyl oxide are 1 by weight: (0.10～0.50) is dissolved in the reaction medium, add tertiary amine and carry out catalyzed reaction, reaction is after pickling, washing, VE-succinate; B) VE-succinate that is obtained by step a and polyoxyethylene glycol in molar ratio 1: (0.5～3.0) is dissolved in the solvent, adding catalyst acid reacts, solvent is reclaimed in the reaction back, adds the recrystallization solvent recrystallization afterwards, through suction filtration, the dry final product vitamin E polyethylene glycol succinic acid ester that gets.
2, the preparation method of a kind of watermiscible vitamin E according to claim 1,20～80 ℃ of temperature of reaction that it is characterized in that step a, reaction times is 1～6 hour, the weight ratio of vitamin-E and reaction medium is 1: (0.5～10.0), the mol ratio of vitamin-E and tertiary amine catalyst are 1: (0.1～2.5).
3, the preparation method of a kind of watermiscible vitamin E according to claim 2 is characterized in that the reaction medium that step a adopts is toluene, acetone, butanone, hexane, hexanaphthene or sherwood oil.
4, the preparation method of a kind of watermiscible vitamin E according to claim 2 is characterized in that the tertiary amine catalyst that step a adopts is triethylamine, Tetramethyl Ethylene Diamine or Dimethylamino pyridine.
5, the preparation method of a kind of watermiscible vitamin E according to claim 1, the temperature of reaction that it is characterized in that step b is 30～150 ℃, reaction times is 1～10 hour, the weight ratio of vitamin-E and solvent is 1: (0.5～10.0), the mol ratio of vitamin-E and catalyst acid are 1: (0.5～5.0).
6, the preparation method of a kind of watermiscible vitamin E according to claim 5 is characterized in that the solvent that step b adopts is toluene, acetone, butanone, hexane, hexanaphthene or tetrahydrofuran (THF).
7, the preparation method of a kind of watermiscible vitamin E according to claim 5 is characterized in that the catalyst acid that step b adopts is sulfuric acid, phosphoric acid or p-methyl benzenesulfonic acid.
8, the preparation method of a kind of watermiscible vitamin E according to claim 5 is characterized in that the recrystallization solvent that step b adopts is alcohols or ether compound, recrystallization temperature-5～20 ℃.
9, the preparation method of a kind of watermiscible vitamin E according to claim 8 is characterized in that described alcohol compound is methyl alcohol, ethanol, Virahol or isopropylcarbinol, and ether compound is ether or isopropyl ether.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100160327A CN100335475C (en) | 2004-01-18 | 2004-01-18 | Method for preparing water-base vitamin E |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2004100160327A CN100335475C (en) | 2004-01-18 | 2004-01-18 | Method for preparing water-base vitamin E |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1640874A true CN1640874A (en) | 2005-07-20 |
| CN100335475C CN100335475C (en) | 2007-09-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100160327A Expired - Lifetime CN100335475C (en) | 2004-01-18 | 2004-01-18 | Method for preparing water-base vitamin E |
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| Country | Link |
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| CN (1) | CN100335475C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101787118A (en) * | 2010-03-10 | 2010-07-28 | 浙江大学 | Solvent-free method for synthesizing water-soluble vitamin E polyethylene glycol succinic acid ester |
| CN101912349A (en) * | 2010-08-19 | 2010-12-15 | 成都慧盈贸易有限公司 | Application of water soluble vitamin E for preparing transdermal enhancer and cosmetics prepared therefrom |
| CN106748946A (en) * | 2017-02-14 | 2017-05-31 | 烟台固特丽生物科技股份有限公司 | A kind of preparation method of containing water-soluble astaxanthin crop nutrient solution |
| CN113201131A (en) * | 2021-04-30 | 2021-08-03 | 山东新元素生物科技有限公司 | Method for preparing d-alpha-tocopherol polyethylene glycol succinate by using leftovers |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980481B (en) * | 2014-04-21 | 2016-01-20 | 江苏玺鑫维生素有限公司 | The preparation method of watermiscible vitamin E |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5234695A (en) * | 1990-07-24 | 1993-08-10 | Eastman Kodak Company | Water dispersible vitamin E composition |
| CN1199966C (en) * | 2001-02-07 | 2005-05-04 | 吴坤 | Process for preparing VE-succinate injection |
-
2004
- 2004-01-18 CN CNB2004100160327A patent/CN100335475C/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101787118A (en) * | 2010-03-10 | 2010-07-28 | 浙江大学 | Solvent-free method for synthesizing water-soluble vitamin E polyethylene glycol succinic acid ester |
| CN101787118B (en) * | 2010-03-10 | 2011-09-14 | 浙江大学 | Solvent-free method for synthesizing water-soluble vitamin E polyethylene glycol succinic acid ester |
| CN101912349A (en) * | 2010-08-19 | 2010-12-15 | 成都慧盈贸易有限公司 | Application of water soluble vitamin E for preparing transdermal enhancer and cosmetics prepared therefrom |
| CN101912349B (en) * | 2010-08-19 | 2012-07-18 | 成都慧盈贸易有限公司 | Application of water soluble vitamin E for preparing transdermal enhancer and cosmetics prepared therefrom |
| CN106748946A (en) * | 2017-02-14 | 2017-05-31 | 烟台固特丽生物科技股份有限公司 | A kind of preparation method of containing water-soluble astaxanthin crop nutrient solution |
| CN113201131A (en) * | 2021-04-30 | 2021-08-03 | 山东新元素生物科技有限公司 | Method for preparing d-alpha-tocopherol polyethylene glycol succinate by using leftovers |
| CN113201131B (en) * | 2021-04-30 | 2022-08-23 | 山东新元素生物科技有限公司 | Method for preparing d-alpha-tocopherol polyethylene glycol succinate by using leftovers |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100335475C (en) | 2007-09-05 |
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