JP2001504111A - d,1―α―トコフェロールの製造方法 - Google Patents
d,1―α―トコフェロールの製造方法Info
- Publication number
- JP2001504111A JP2001504111A JP52215398A JP52215398A JP2001504111A JP 2001504111 A JP2001504111 A JP 2001504111A JP 52215398 A JP52215398 A JP 52215398A JP 52215398 A JP52215398 A JP 52215398A JP 2001504111 A JP2001504111 A JP 2001504111A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- isophytol
- amount
- formula
- trimethylhydroquinone
- 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.)
- Ceased
Links
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. トリメチルヒドロキノンのイソフィトールとの触媒縮合によるd,l− α−トコフェロールの製造のための方法であって、触媒としての、ビスー(トリ フルオロメチルスルホニル)アミン[HN(SO2CF3)2]、又は式: Met[N(SO2CF3)2]n I [式中、Metは、リチウム、ホウ素、マグネシウム、アルミニウム、ケイ素 、スカンジウム、チタン、バナジウム、マンガン、鉄、コバルト、ニッケル、銅 、亜鉛、イットリウム、ジルコニウム、ロジウム、パラジウム、銀、スズ、ラン タン、セリウム、ネオジム、プラセオジム、ユウロピウム、ジスプロシウム、イ ッテルビウム、ハフニウム、プラチナ、及び金の群から選択される金属原子を表 し、 nは、金属原子Metの対応する原子価(1、2、3又は4)を表す] で示されるその金属塩の存在下、あるいは、触媒系としての、式(I)の金属塩 と強酸の組み合わせの存在下、有機溶媒中で縮合を行なう方法。 2. 非プロトン性溶媒、特に脂肪族又は環式ケトン、脂肪族又は環式エステ ル、あるいは芳香族炭化水素を有機溶媒として使用する、請求項1記載の方法。 3. 溶媒が、イソブチルメチルケトン、酢酸エチル、酢酸イソプロピル、又 はトルエンである、請求項2記載の方法。 4. 触媒として用いるビス−(トリフルオロメチルスルホニル)アミンの量 が、約0.08〜0.3モル%、そして用いる式(I)の触媒の量が、約0.5 〜4モル%である(いずれの場合も、トリメチルヒドロキノン又はイソフィトー ルの量に基づく)、請求項1〜3のいずれか1項記載の方法。 5. 式(I)の金属塩の量が、約0.1〜4モル%であり、ブレンステッド 酸の量が、約0.01〜0.5モル%である(いずれの場合も、反応物の量に基 づく)触媒系を用いる、請求項1〜4のいずれか1項記載の方法。 6. トリメチルヒドロキノン又はイソフィトール100mmol当り、約25〜 100ml、好ましくは約40〜50mlの有機溶媒を用いる、請求項1〜5のいず れか1項記載の方法。 7. 縮合を、約80℃〜約150℃の間、好ましくは約100℃〜約140 ℃の間、特に約105℃〜約120℃の間の温度で行なう、請求項1〜6のいず れか1項記載の方法。 8. トリメチルヒドロキノン及び触媒を溶媒に含む懸濁液にイソフィトール を滴下により加える、請求項1〜7のいずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96118037 | 1996-11-11 | ||
EP96118037.9 | 1996-11-11 | ||
PCT/EP1997/006227 WO1998021197A2 (en) | 1996-11-11 | 1997-11-10 | PROCESS FOR MANUFACTURING d,l-α-TOCOPHEROL |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2001504111A true JP2001504111A (ja) | 2001-03-27 |
Family
ID=8223387
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP52215398A Ceased JP2001504111A (ja) | 1996-11-11 | 1997-11-10 | d,1―α―トコフェロールの製造方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US5908939A (ja) |
EP (1) | EP0937055B1 (ja) |
JP (1) | JP2001504111A (ja) |
CN (1) | CN1105714C (ja) |
DE (1) | DE69711669T2 (ja) |
DK (1) | DK0937055T3 (ja) |
ES (1) | ES2173500T3 (ja) |
WO (1) | WO1998021197A2 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005511777A (ja) * | 2001-12-14 | 2005-04-28 | ディーエスエム アイピー アセッツ ビー.ブイ. | トリメチルヒドロキノンジアシレートの製造 |
JP2006514959A (ja) * | 2003-01-13 | 2006-05-18 | 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 |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6458373B1 (en) | 1997-01-07 | 2002-10-01 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
US7030155B2 (en) | 1998-06-05 | 2006-04-18 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
FR2784104B1 (fr) * | 1998-09-18 | 2002-12-27 | Rhone Poulenc Nutrition Animal | Procede de preparation de la vitamine e |
CA2288851A1 (en) * | 1998-11-11 | 2000-05-11 | F. Hoffmann-La Roche Ag | Process for manufacturing d,i-alpha-tocopherol |
EP1000940A1 (en) * | 1998-11-11 | 2000-05-17 | F. Hoffmann-La Roche Ag | Process for manufacturing d,l-alpha-tocopherol |
KR100452291B1 (ko) * | 1999-12-14 | 2004-10-08 | 에스케이 주식회사 | 고수율 및 고순도로 DL-α-토코페롤를 제조하는 방법 |
US6369242B2 (en) | 2000-03-17 | 2002-04-09 | Roche Vitamins Inc. | Tocopherol manufacture by tris(perfluorohydrocarbylsulphonyl) methane or metal methides thereof |
ES2204792T3 (es) | 2000-08-18 | 2004-05-01 | Roche Vitamins Ag | Procedimiento par ala obtencion de (todo-rac)-alfa-tocoferol. |
EP1370508A2 (en) * | 2001-03-12 | 2003-12-17 | The Queen's University of Belfast | Process catalysed by fluoroalkysulfonated compounds, preferably bis-triflimide compounds |
CN1266112C (zh) * | 2001-04-24 | 2006-07-26 | 麻省理工学院 | 铜-催化的碳-杂原子键和碳-碳键的形成 |
AU2003257062A1 (en) | 2002-08-02 | 2004-02-23 | Massachusetts Institute Of Technology | Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds |
CN100355745C (zh) * | 2005-03-18 | 2007-12-19 | 清华大学 | 离子液体催化合成D,L-α-生育酚的方法 |
FR2889519B1 (fr) * | 2005-08-04 | 2008-07-11 | Rhodia Chimie Sa | Procede de c-alkylation de composes aromatiques hydroxyles avec un catalyseur de type tfsih |
EP2050743A1 (en) * | 2007-10-19 | 2009-04-22 | Humboldt-Universität zu Berlin | Method for the synthesis of dl.(alpha)-tocopherol and means therefore |
US8226850B1 (en) * | 2009-09-22 | 2012-07-24 | Clemson University Research Foundation | Thermally enhanced oxygen scavengers including a transition metal and a free radical scavenger |
CN102285955B (zh) * | 2011-09-14 | 2012-12-05 | 重庆大学 | 一种α-生育酚乙酸酯的制备方法 |
CN102276572B (zh) * | 2011-09-14 | 2013-03-27 | 重庆大学 | 一种制备维生素e乙酸酯的方法 |
US9469620B2 (en) | 2012-12-21 | 2016-10-18 | Rhodia Operations | Process for forming a primary, a secondary or a tertiary amine via a direct amination reaction |
CN104936941A (zh) * | 2012-12-21 | 2015-09-23 | 罗地亚经营管理公司 | 用于经由直接胺化反应形成伯胺、仲胺或叔胺的方法 |
CN108017610B (zh) * | 2017-12-22 | 2020-11-06 | 浙江新和成药业有限公司 | 一种维生素e的制备方法 |
CN108409704A (zh) * | 2018-01-24 | 2018-08-17 | 上海优合生物科技有限公司 | 一种高纯度生育酚琥珀酸酯盐的制备方法 |
CN109705082B (zh) * | 2018-12-19 | 2021-04-20 | 万华化学集团股份有限公司 | 一种制备维生素e乙酸酯的方法 |
CN113321669B (zh) * | 2020-02-28 | 2023-03-24 | 中国科学院上海有机化学研究所 | 一种磺酰亚胺类金属盐、其制备方法及应用 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2723278A (en) * | 1954-01-25 | 1955-11-08 | Hoffmann La Roche | Preparation of alpha-tocopherol |
GB1148652A (en) * | 1965-07-20 | 1969-04-16 | Dunlop Co Ltd | Polymer compositions comprising polymerized episulphides and a process for the preparation of reaction products of polymerized episulphides |
US3459773A (en) * | 1966-12-27 | 1969-08-05 | Takasago Perfumery Co Ltd | Process for producing alpha-tocopherol and its esters |
CH547278A (de) * | 1971-01-11 | 1974-03-29 | Hoffmann La Roche | Verfahren zur herstellung von chromanderivaten. |
US4208334A (en) * | 1978-12-22 | 1980-06-17 | Hoffmann-La Roches Inc. | Process for preparation of α-tocopherol |
US4634781A (en) * | 1982-09-30 | 1987-01-06 | Basf Corporation | Alpha tocopherol process |
FR2637284B1 (fr) * | 1988-10-05 | 1991-07-05 | Elf Aquitaine | Methode de synthese de sulfonylimidures |
DE4243464A1 (de) * | 1992-12-22 | 1994-06-23 | Basf Ag | Verfahren zur Herstellung von alpha-Tocopherol und alpha-Tocopherylacetat in flüssigem oder überkritischem Kohlendioxid |
WO1994014794A1 (en) * | 1992-12-28 | 1994-07-07 | Yoshitomi Pharmaceutical Industries, Ltd. | 8-methoxyquinolonecarboxylic acid derivative |
US5526821A (en) * | 1993-06-03 | 1996-06-18 | Medical Biopsy, Inc. | Biopsy needle with sample retaining means |
JP3848380B2 (ja) * | 1993-12-14 | 2006-11-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | α−トコフェロール誘導体の製造法 |
JP3166959B2 (ja) * | 1994-03-11 | 2001-05-14 | セントラル硝子株式会社 | ルイス酸触媒 |
DE4425609A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Benzofuranyl- und Benzothienyloxazolidinone |
JP3117369B2 (ja) * | 1994-09-12 | 2000-12-11 | セントラル硝子株式会社 | スルホンイミドの製造方法 |
DE59610172D1 (de) * | 1996-01-05 | 2003-04-03 | Hoffmann La Roche | Verfahren zur Herstellung von d,l-alpha-Tocopherol in Gegenwart einer Perfluoralkylensulfonsäure als Katalysator |
-
1997
- 1997-10-16 US US08/951,273 patent/US5908939A/en not_active Expired - Lifetime
- 1997-11-10 DK DK97950150T patent/DK0937055T3/da active
- 1997-11-10 DE DE69711669T patent/DE69711669T2/de not_active Expired - Lifetime
- 1997-11-10 EP EP97950150A patent/EP0937055B1/en not_active Expired - Lifetime
- 1997-11-10 JP JP52215398A patent/JP2001504111A/ja not_active Ceased
- 1997-11-10 WO PCT/EP1997/006227 patent/WO1998021197A2/en not_active Application Discontinuation
- 1997-11-10 ES ES97950150T patent/ES2173500T3/es not_active Expired - Lifetime
- 1997-11-10 CN CN97199633A patent/CN1105714C/zh not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005511777A (ja) * | 2001-12-14 | 2005-04-28 | ディーエスエム アイピー アセッツ ビー.ブイ. | トリメチルヒドロキノンジアシレートの製造 |
JP2006514959A (ja) * | 2003-01-13 | 2006-05-18 | 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 |
Also Published As
Publication number | Publication date |
---|---|
ES2173500T3 (es) | 2002-10-16 |
CN1105714C (zh) | 2003-04-16 |
CN1237163A (zh) | 1999-12-01 |
WO1998021197A3 (en) | 1998-07-23 |
US5908939A (en) | 1999-06-01 |
EP0937055A2 (en) | 1999-08-25 |
DK0937055T3 (da) | 2002-07-29 |
DE69711669T2 (de) | 2002-10-02 |
EP0937055B1 (en) | 2002-04-03 |
WO1998021197A2 (en) | 1998-05-22 |
DE69711669D1 (de) | 2002-05-08 |
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Legal Events
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