FR2581384A1 - Procede d'extraction de tocopherol a l'aide de methanol - Google Patents
Procede d'extraction de tocopherol a l'aide de methanol Download PDFInfo
- Publication number
- FR2581384A1 FR2581384A1 FR8606550A FR8606550A FR2581384A1 FR 2581384 A1 FR2581384 A1 FR 2581384A1 FR 8606550 A FR8606550 A FR 8606550A FR 8606550 A FR8606550 A FR 8606550A FR 2581384 A1 FR2581384 A1 FR 2581384A1
- Authority
- FR
- France
- Prior art keywords
- tocopherol
- sep
- phase
- temperature
- methanol
- 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.)
- Withdrawn
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 163
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products 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 114
- 239000011732 tocopherol Substances 0.000 title claims abstract description 112
- 229930003799 tocopherol Natural products 0.000 title claims abstract description 111
- 229960001295 tocopherol Drugs 0.000 title claims abstract description 103
- 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 title claims abstract description 103
- 235000010384 tocopherol Nutrition 0.000 title claims abstract description 102
- 238000000034 method Methods 0.000 title claims description 34
- 238000000605 extraction Methods 0.000 title description 69
- 239000000463 material Substances 0.000 claims abstract description 16
- 239000012535 impurity Substances 0.000 claims description 25
- 239000000945 filler Substances 0.000 claims description 22
- 238000000746 purification Methods 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 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 abstract description 7
- 229930003427 Vitamin E Natural products 0.000 abstract description 6
- 235000019165 vitamin E Nutrition 0.000 abstract description 6
- 239000011709 vitamin E Substances 0.000 abstract description 6
- 229940046009 vitamin E Drugs 0.000 abstract description 6
- 239000012071 phase Substances 0.000 description 74
- 239000000126 substance Substances 0.000 description 9
- 235000019149 tocopherols Nutrition 0.000 description 9
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000011084 recovery Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 229930182558 Sterol Natural products 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 235000003702 sterols Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000003432 sterols Chemical class 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 150000003722 vitamin derivatives Chemical class 0.000 description 3
- DFUSDJMZWQVQSF-XLGIIRLISA-N (2r)-2-methyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol Chemical class OC1=CC=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 DFUSDJMZWQVQSF-XLGIIRLISA-N 0.000 description 2
- 241001133760 Acoelorraphe Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 150000003611 tocopherol derivatives Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 235000004835 α-tocopherol Nutrition 0.000 description 2
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 2
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 235000010389 delta-tocopherol Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000010382 gamma-tocopherol Nutrition 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- -1 sterol hydrocarbons Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 150000003505 terpenes Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 150000003772 α-tocopherols Chemical class 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73117885A | 1985-05-06 | 1985-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2581384A1 true FR2581384A1 (fr) | 1986-11-07 |
Family
ID=24938396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8606550A Withdrawn FR2581384A1 (fr) | 1985-05-06 | 1986-05-06 | Procede d'extraction de tocopherol a l'aide de methanol |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS61268677A (de) |
| DE (1) | DE3615029A1 (de) |
| FR (1) | FR2581384A1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120130094A1 (en) * | 2009-07-30 | 2012-05-24 | Patcharin Raviyan | System and method for extracting vitamin e from fatty acid distillates |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4228476C2 (de) * | 1992-08-27 | 2002-05-02 | Cognis Deutschland Gmbh | Verfahren zum Gewinnen von Tocopherol und/oder Sterin |
| ES2207931T3 (es) | 1998-01-29 | 2004-06-01 | Eastman Chemical Company | Procedimientos para separar un tocotrienol de una mezcla a base de tocol y composiciones producidas segun dichos procedimientos. |
| US6706898B2 (en) | 1998-01-29 | 2004-03-16 | Archer-Daniels-Midland Company | Methods for separating a tocopherol from a tocopherol-containing mixture |
| US7416756B2 (en) | 2003-09-10 | 2008-08-26 | Eastman Chemical Company | Process for the recovery of a phytolipid composition |
| AU2004272561A1 (en) * | 2003-09-10 | 2005-03-24 | Eastman Chemical Company | Process for the recovery of a phytolipid composition |
| CN103012351B (zh) * | 2012-09-03 | 2015-09-02 | 宁波大红鹰生物工程股份有限公司 | 一种天然维生素e的提纯工艺 |
| JP6681843B2 (ja) * | 2014-02-11 | 2020-04-15 | エボニック オペレーションズ ゲーエムベーハー | 天然油からのビタミンｅ濃縮組成物、特にトコトリエノール濃縮組成物の製造方法 |
| MY184673A (en) * | 2018-03-16 | 2021-04-15 | Palm Nutraceuticals Sdn Bhd | A process of preparing vitamin e concentrate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3402182A (en) * | 1966-04-28 | 1968-09-17 | Eisai Co Ltd | Method of isolating and refining tocopherol homologues |
| US4550183A (en) * | 1984-08-02 | 1985-10-29 | Henkel Corporation | Purification of tocopherols |
-
1986
- 1986-05-02 DE DE19863615029 patent/DE3615029A1/de not_active Withdrawn
- 1986-05-06 FR FR8606550A patent/FR2581384A1/fr not_active Withdrawn
- 1986-05-06 JP JP10460186A patent/JPS61268677A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3402182A (en) * | 1966-04-28 | 1968-09-17 | Eisai Co Ltd | Method of isolating and refining tocopherol homologues |
| US4550183A (en) * | 1984-08-02 | 1985-10-29 | Henkel Corporation | Purification of tocopherols |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120130094A1 (en) * | 2009-07-30 | 2012-05-24 | Patcharin Raviyan | System and method for extracting vitamin e from fatty acid distillates |
| US9078850B2 (en) * | 2009-07-30 | 2015-07-14 | The Thailand Research Fund | System and method for extracting vitamin E from fatty acid distillates |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3615029A1 (de) | 1986-11-06 |
| JPS61268677A (ja) | 1986-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Withdrawal of published application |