CN1136211C - 制备α-生育酚酯的方法 - Google Patents
制备α-生育酚酯的方法 Download PDFInfo
- Publication number
- CN1136211C CN1136211C CNB981256864A CN98125686A CN1136211C CN 1136211 C CN1136211 C CN 1136211C CN B981256864 A CNB981256864 A CN B981256864A CN 98125686 A CN98125686 A CN 98125686A CN 1136211 C CN1136211 C CN 1136211C
- Authority
- CN
- China
- Prior art keywords
- acid
- tmhq
- acetate
- reaction
- vitamin
- 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 - Fee Related
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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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
共溶剂 | 最终重量(g) | 维生素E含量(wt%) | VE乙酸酯含量(wt%) | 总产率(理论值的%) |
/ | 20.9 | 40.3 | 53.2 | 93.9 |
正丁醇 | 21.5 | 45.5 | 49.2 | 97.8 |
1-戊醇 | 22.6 | 32.5 | 60.7 | 93.9 |
2-戊醇 | 22.2 | 23.3 | 66.0 | 93.2 |
3-戊醇 | 23.0 | 19.4 | 68.4 | 94.6 |
ZnCl2的量(mol%) | ZnCl2的量(g) | VE/VE-Ac的比 | VE含量(wt%) | VE乙酸酯含量(wt%) | 最终重量(g)* | 转化率(%) | 产率** |
0.0 | 0.0 | 99∶1 | 8.3 | 0.14 | 17.4 | 28.5 | 7.4 |
15.9 | 1.0 | 23∶77 | 14.7 | 53.9 | 22.6 | 81 | 72.6 |
25.4 | 1.6 | 35∶65 | 25.6 | 65.2 | 21.0 | 98.3 | 85.4 |
41.4 | 2.6 | 33∶67 | 28 | 62.3 | 21.3 | 97.3 | 91.0 |
51 | 3.2 | 31∶69 | 25.9 | 61.8 | 21.2 | 97.3 | 92.5 |
63.5 | 4.0 | 34∶66 | 28.9 | 61.7 | 22.1 | 99.0 | 94.8 |
82.9 | 5.2 | 43∶57 | 37.6 | 54.4 | 21.7 | 99.3 | 95.4 |
100 | 6.3 | 28∶72 | 22.1 | 62.5 | 21.8 | 98.3 | 98.3 |
ZnBr2的量(mol.%) | ZnBr2的量(g) | VE/VE-Ac的比 | VE含量(wt.%) | VE乙酸酯含量(wt.%) | 最终重量(g)* | 转化率(%) | 产率** |
10 | 1.04 | 32∶68 | 19.34 | 44.24 | 22.5 | 97.4 | 67.6 |
20 | 2.08 | 31∶69 | 25.57 | 63.71 | 22.2 | 99.3 | 93.5 |
30 | 3.11 | 37∶63 | 31.92 | 58.62 | 22.1 | 100 | 94.9 |
40 | 4.16 | 44∶56 | 37.66 | 53.62 | 21.6 | 100 | 93.6 |
60 | 6.22 | 30∶70 | 25.98 | 66.0 | 21.5 | 100 | 93.2 |
80 | 8.32 | 36∶64 | 30.85 | 60.2 | 22.2 | 100 | 95.8 |
100 | 10.38 | 40∶60 | 34.31 | 55.41 | 22.1 | 100 | 94.3 |
LeWis酸 | 质子酸类型 | 浓度(mol%) | 水浓度(mol%) | 产率(%)** | 转化率(%) | VE/VE-Ac(摩尔比) |
ZnBr2 | 浓盐酸(=37%) | 25 | 86(=0.95ml) | 91.7 | 99.9 | 48∶52 |
ZnBr2 | 浓氢溴酸(=47%) | 25 | 126(=1.35ml) | 92.2 | 99.8 | 51∶49 |
ZnBr2 | 浓氢碘酸(=57%) | 25 | 134(=1.52ml) | 91.7 | 99.9 | 50∶50 |
ZnBr2 | H2SO4(=30%) | 25 | 319(=3.1ml) | 92.9 | 99 | 60∶40 |
ZnBr2 | H2SO4(=60%) | 25 | 91(=1.26ml) | 89.5 | 99.8 | 47∶53 |
ZnBr2 | NaHSO4(=70%) | 25 | 86(=2.29g) | 79.4 | 98.4 | 22∶78 |
ZnBr2 | CF3SO3H(=30%) | 25 | 482(=5ml) | 83.8 | 98.9 | 44∶56 |
ZnBr2 | Cl3CO2H(=70%) | 25 | 96(=2.68g) | 32.2 | 69.6 | 2∶98 |
ZnBr2 | Cl3CO2H(=100%) | 50 | 0(=3.77g) | 41.2 | 71.5 | 3∶97 |
ZnBr2 | H3PO4(=60%) | 25 | 91(=1.32ml) | 68.2 | 88.6 | 29∶71 |
溶剂(ml) | 20 | 60 |
ZnCl2(mol%) | 40 | 40 |
H+浓度(mol%)** | 25 | 25 |
水浓度(mol%) | 85(=0.7ml | 85(=0.7ml |
产率(%)*** | 89.9 | 80.2 |
IP转化率(%) | 100 | 100 |
存留的TMHQ酯 | 92 | 89 |
VE/VE-Ac(摩尔比) | 3∶97 | 3∶97 |
ZnCl2(mol%) | H+浓度(mol%)* | 温度(℃) | 产率(%)** | IP转化率(%) | VE/VE-Ac(摩尔比) |
40 | 25 | 60 | 81.54 | 100 | 52∶48 |
40 | 25 | 100 | 78.4 | 100 | 85∶15 |
40 | 12.5 | 60 | 78.4 | 100 | 39∶61 |
40 | 12.5 | 80 | 79.8 | 100 | 54∶46 |
40 | 12.5 | 100 | 75.2 | 100 | 68∶32 |
Lewis酸(mol%) | 质子酸的类型 | 浓度(mol%)* | 水浓度(mol.%)** | 产率(%)*** | 转化率 | VE/VE-Ac(摩尔比) |
ZnBr2(82.9) | CF3SO3H | 25 | 482 | 83.8 | 98.9 | 44∶56 |
ZnBr2(82.9) | CF3SO3H | 25 | 96 | 94.5 | 100 | 45∶55 |
ZnBr2(82.9) | CF3SO3H | 10 | 96 | 97.1 | 100 | 46∶54 |
ZnBr2(82.9) | CF3SO3H | 10 | 48 | 90.1 | 100 | 29∶71 |
ZnBr2(82.9) | CF3SO3H | 5 | 96 | 82.7 | 97.3 | 15∶85 |
ZnBr2(82.9) | CF3SO3H | 5 | 48 | 80.6 | 97.1 | 17∶83 |
Claims (11)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19757124A DE19757124A1 (de) | 1997-12-20 | 1997-12-20 | Verfahren zur Herstellung von alpha-Tocopherolestern |
DE19757124.7 | 1997-12-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1224012A CN1224012A (zh) | 1999-07-28 |
CN1136211C true CN1136211C (zh) | 2004-01-28 |
Family
ID=7852911
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB981256864A Expired - Fee Related CN1136211C (zh) | 1997-12-20 | 1998-12-21 | 制备α-生育酚酯的方法 |
Country Status (12)
Country | Link |
---|---|
US (1) | US6048988A (zh) |
EP (1) | EP0924208B1 (zh) |
JP (1) | JPH11246549A (zh) |
CN (1) | CN1136211C (zh) |
BR (1) | BR9805589A (zh) |
CA (1) | CA2256988A1 (zh) |
DE (2) | DE19757124A1 (zh) |
ID (1) | ID21588A (zh) |
IL (1) | IL127634A (zh) |
IN (1) | IN185169B (zh) |
TW (1) | TW502029B (zh) |
YU (1) | YU58298A (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2784104B1 (fr) | 1998-09-18 | 2002-12-27 | Rhone Poulenc Nutrition Animal | Procede de preparation de la vitamine e |
DE19951006A1 (de) * | 1999-10-22 | 2001-04-26 | Degussa | Verfahren zur Herstellung von veresterten Chromanverbindungen |
DE10011402A1 (de) * | 2000-03-09 | 2001-09-13 | Degussa | Verfahren zur Herstellung von alpha-Tocopherolestern |
KR100533304B1 (ko) * | 2001-05-26 | 2005-12-05 | 주식회사 엘지생명과학 | 폴리에톡실화 알파 토코페롤 에스테르 유도체 및 이의제조방법 |
KR100787879B1 (ko) * | 2002-02-27 | 2007-12-27 | (주)아모레퍼시픽 | 항산화력을 갖는 토코페롤 유도체 및 그의 제조방법, 이를함유하는 화장료 조성물 |
DE60317553T2 (de) * | 2002-11-21 | 2008-10-23 | Dsm Ip Assets B.V. | Herstellung von tocoferylazetaten |
ES2347552T3 (es) | 2003-01-13 | 2010-11-02 | Dsm Ip Assets B.V. | Proceso para la fabricacion de acetato de alfa-tocoferilo. |
CN105418574A (zh) * | 2014-08-27 | 2016-03-23 | 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 |
CN113083339B (zh) * | 2021-04-15 | 2022-11-08 | 万华化学(四川)有限公司 | 一种用于制备维生素e的催化剂及其制备方法和应用 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH547278A (de) * | 1971-01-11 | 1974-03-29 | Hoffmann La Roche | Verfahren zur herstellung von chromanderivaten. |
FR2259822A1 (en) * | 1974-02-06 | 1975-08-29 | Teijin Ltd | Cpds. contg. chroman rings - from hydroquinones and carboxylic acid derivs in the presence of an insol solid acid catalyst |
JPS5180859A (en) * | 1975-01-11 | 1976-07-15 | Teijin Ltd | Arufua tokofuerooruruino seizoho |
US5663376A (en) * | 1994-07-27 | 1997-09-02 | Eisai Co., Ltd. | Process for the preparation of α-tocopherol |
-
1997
- 1997-12-20 DE DE19757124A patent/DE19757124A1/de not_active Withdrawn
-
1998
- 1998-12-04 DE DE59807380T patent/DE59807380D1/de not_active Expired - Fee Related
- 1998-12-04 EP EP98123135A patent/EP0924208B1/de not_active Expired - Lifetime
- 1998-12-15 TW TW087120855A patent/TW502029B/zh active
- 1998-12-16 YU YU58298A patent/YU58298A/sh unknown
- 1998-12-16 IN IN2182CA1998 patent/IN185169B/en unknown
- 1998-12-17 JP JP10359047A patent/JPH11246549A/ja active Pending
- 1998-12-17 ID IDP981642A patent/ID21588A/id unknown
- 1998-12-17 BR BR9805589-5A patent/BR9805589A/pt not_active IP Right Cessation
- 1998-12-18 CA CA002256988A patent/CA2256988A1/en not_active Abandoned
- 1998-12-18 IL IL12763498A patent/IL127634A/xx not_active IP Right Cessation
- 1998-12-21 CN CNB981256864A patent/CN1136211C/zh not_active Expired - Fee Related
- 1998-12-21 US US09/216,914 patent/US6048988A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
BR9805589A (pt) | 2000-04-11 |
IL127634A (en) | 2003-03-12 |
IL127634A0 (en) | 1999-10-28 |
ID21588A (id) | 1999-06-24 |
YU58298A (sh) | 2000-12-28 |
DE19757124A1 (de) | 1999-06-24 |
EP0924208B1 (de) | 2003-03-05 |
EP0924208A1 (de) | 1999-06-23 |
IN185169B (zh) | 2000-12-02 |
CN1224012A (zh) | 1999-07-28 |
DE59807380D1 (de) | 2003-04-10 |
TW502029B (en) | 2002-09-11 |
JPH11246549A (ja) | 1999-09-14 |
US6048988A (en) | 2000-04-11 |
CA2256988A1 (en) | 1999-06-20 |
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