DE60317553D1 - Herstellung von tocoferylazetaten - Google Patents
Herstellung von tocoferylazetatenInfo
- Publication number
- DE60317553D1 DE60317553D1 DE60317553T DE60317553T DE60317553D1 DE 60317553 D1 DE60317553 D1 DE 60317553D1 DE 60317553 T DE60317553 T DE 60317553T DE 60317553 T DE60317553 T DE 60317553T DE 60317553 D1 DE60317553 D1 DE 60317553D1
- Authority
- DE
- Germany
- Prior art keywords
- acetate
- trimethylhydroquinone
- phytyl
- sup
- alkylating
- 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
- RJDGWYMSVUNFJU-FUFCXQQYSA-N 2-[1,4-dihydroxy-2,3,6-trimethyl-5-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]cyclohexa-2,4-dien-1-yl]acetic acid Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C(C)=C(C)C(O)(CC(O)=O)C1C RJDGWYMSVUNFJU-FUFCXQQYSA-N 0.000 abstract 3
- 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 abstract 3
- -1 phytyl halide Chemical class 0.000 abstract 3
- OXEURVFAJQZVRZ-UHFFFAOYSA-N CC1C(C)=C(O)C=C(C)C1(O)CC(O)=O Chemical compound CC1C(C)=C(O)C=C(C)C1(O)CC(O)=O OXEURVFAJQZVRZ-UHFFFAOYSA-N 0.000 abstract 2
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 abstract 2
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-N 0.000 abstract 1
- BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 abstract 1
- HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 abstract 1
- 229930003427 Vitamin E Natural products 0.000 abstract 1
- BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 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 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000006462 rearrangement reaction Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 229940046009 vitamin E Drugs 0.000 abstract 1
- 239000011709 vitamin E Substances 0.000 abstract 1
- 235000019165 vitamin E Nutrition 0.000 abstract 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02025989 | 2002-11-21 | ||
| EP02025989 | 2002-11-21 | ||
| PCT/EP2003/010789 WO2004046126A1 (en) | 2002-11-21 | 2003-09-29 | Manufacture of tocopheryl acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60317553D1 true DE60317553D1 (de) | 2007-12-27 |
| DE60317553T2 DE60317553T2 (de) | 2008-10-23 |
Family
ID=32319545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60317553T Expired - Lifetime DE60317553T2 (de) | 2002-11-21 | 2003-09-29 | Herstellung von tocoferylazetaten |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7169943B2 (de) |
| EP (1) | EP1562929B1 (de) |
| JP (1) | JP4932158B2 (de) |
| KR (1) | KR101078957B1 (de) |
| CN (1) | CN100503593C (de) |
| AT (1) | ATE378325T1 (de) |
| AU (1) | AU2003271655A1 (de) |
| DE (1) | DE60317553T2 (de) |
| WO (1) | WO2004046126A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4558506B2 (ja) * | 2003-01-13 | 2010-10-06 | ディーエスエム アイピー アセッツ ビー．ブイ． | 酢酸α−トコフェリルの製造方法 |
| US7622591B2 (en) | 2003-09-15 | 2009-11-24 | Dsm Ip Assets B.V. | Route to α- tocopheryl alkanoates and percursors thereof |
| US20060235234A1 (en) * | 2003-09-15 | 2006-10-19 | Werner Bonrath | New route to alpha-tocopherol, alpha-tocopheryl alkanoates and precursors thereof |
| EA027287B1 (ru) * | 2010-08-26 | 2017-07-31 | ДСМ АйПи АССЕТС Б.В. | Способ получения 2,3,5-триметилгидро-п-бензохинона (варианты), способы получения промежуточных продуктов, способ получения витамина е и ацетата витамина е |
| US10047065B2 (en) | 2014-12-17 | 2018-08-14 | Dsm Ip Assets B.V. | Formation of chromanes based on intermolecular reaction of alkynes with dimethylfuran in the presence of gold(I) complexes |
| CN108203425A (zh) * | 2016-12-20 | 2018-06-26 | 浙江医药股份有限公司新昌制药厂 | 一种dl-α生育酚醋酸酯的制备方法 |
| JP2024517559A (ja) * | 2021-04-28 | 2024-04-23 | ディーエスエム アイピー アセッツ ビー．ブイ． | ２，３，５－トリメチルヒドロキノン及び不飽和アルコールのカップリング |
| WO2025242782A1 (en) * | 2024-05-23 | 2025-11-27 | Dsm Ip Assets B.V. | Mono-saponifaction of diesters of trimethylhydroquinone and its use in the process of manufacturing esterified alpha-tocopherol |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3708505A (en) * | 1971-02-25 | 1973-01-02 | Diamond Shamrock Corp | Process for preparation of d,l-alpha tocopherol |
| JPS5089372A (de) * | 1973-12-18 | 1975-07-17 | ||
| JPS5838434B2 (ja) * | 1976-10-12 | 1983-08-23 | 日清製粉株式会社 | ２，３，６−トリメチルハイドロキノン−１−ニコチン酸エステルの製造法 |
| DE3573598D1 (en) * | 1984-11-21 | 1989-11-16 | Hoffmann La Roche | Process for the preparation of hydrochinone derivatives |
| JP2947503B2 (ja) * | 1994-03-02 | 1999-09-13 | エーザイ株式会社 | アリルキノン誘導体の製造方法および中間体 |
| DE19757124A1 (de) * | 1997-12-20 | 1999-06-24 | Degussa | Verfahren zur Herstellung von alpha-Tocopherolestern |
| DE69931421T2 (de) | 1998-04-06 | 2006-11-09 | Dsm Ip Assets B.V. | Verfahren zur Herstellung von d,l-alpha-Tocopherol in einem Carbonat-Lösungsmittel und in Anwesenheit eines sauren schwefelhaltigen Katalysators |
| DE10011403A1 (de) * | 2000-03-09 | 2001-09-13 | Degussa | Verfahren zur Herstellung von alpha-Tocopherolacetat durch Kondensation von Trimethylhydrochinon mit Isophytol unter Recyclierung einer essigsauren Katalysatorlösung |
| ATE478960T1 (de) * | 2001-02-21 | 2010-09-15 | Dsm Ip Assets Bv | Verfahren zur herstellung eines vitamin e - zwischenproduktes |
| WO2003037883A1 (en) | 2001-10-31 | 2003-05-08 | Dsm Ip Assets B.V. | Manufacture of alpha- tocopherol |
-
2003
- 2003-09-29 EP EP03753473A patent/EP1562929B1/de not_active Expired - Lifetime
- 2003-09-29 WO PCT/EP2003/010789 patent/WO2004046126A1/en not_active Ceased
- 2003-09-29 AT AT03753473T patent/ATE378325T1/de not_active IP Right Cessation
- 2003-09-29 US US10/535,604 patent/US7169943B2/en not_active Expired - Lifetime
- 2003-09-29 AU AU2003271655A patent/AU2003271655A1/en not_active Abandoned
- 2003-09-29 CN CNB038253437A patent/CN100503593C/zh not_active Expired - Fee Related
- 2003-09-29 KR KR1020057009079A patent/KR101078957B1/ko not_active Expired - Fee Related
- 2003-09-29 DE DE60317553T patent/DE60317553T2/de not_active Expired - Lifetime
- 2003-09-29 JP JP2004552466A patent/JP4932158B2/ja not_active Expired - Fee Related
-
2006
- 2006-12-13 US US11/639,029 patent/US20070112206A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN100503593C (zh) | 2009-06-24 |
| JP2006515280A (ja) | 2006-05-25 |
| EP1562929B1 (de) | 2007-11-14 |
| US20060094886A1 (en) | 2006-05-04 |
| AU2003271655A1 (en) | 2004-06-15 |
| ATE378325T1 (de) | 2007-11-15 |
| US7169943B2 (en) | 2007-01-30 |
| KR20050083917A (ko) | 2005-08-26 |
| US20070112206A1 (en) | 2007-05-17 |
| JP4932158B2 (ja) | 2012-05-16 |
| KR101078957B1 (ko) | 2011-11-01 |
| CN1701066A (zh) | 2005-11-23 |
| DE60317553T2 (de) | 2008-10-23 |
| WO2004046126A1 (en) | 2004-06-03 |
| EP1562929A1 (de) | 2005-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |