RU2178795C2 - Способ получения станоловых эфиров - Google Patents
Способ получения станоловых эфиров Download PDFInfo
- Publication number
- RU2178795C2 RU2178795C2 RU99120095/04A RU99120095A RU2178795C2 RU 2178795 C2 RU2178795 C2 RU 2178795C2 RU 99120095/04 A RU99120095/04 A RU 99120095/04A RU 99120095 A RU99120095 A RU 99120095A RU 2178795 C2 RU2178795 C2 RU 2178795C2
- Authority
- RU
- Russia
- Prior art keywords
- transesterification
- hydrogenation
- solvent
- stanol
- catalyst
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 60
- 150000002148 esters Chemical class 0.000 title claims abstract description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 65
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 53
- 239000003054 catalyst Substances 0.000 claims abstract description 45
- 239000002904 solvent Substances 0.000 claims abstract description 39
- 229930182558 Sterol Natural products 0.000 claims abstract description 32
- 235000003702 sterols Nutrition 0.000 claims abstract description 32
- 150000003432 sterols Chemical class 0.000 claims abstract description 27
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 24
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
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- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 description 1
- 229940058690 lanosterol Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 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 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Fats And Perfumes (AREA)
- Compounds Of Unknown Constitution (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI970802 | 1997-02-26 | ||
| FI970802A FI107538B (fi) | 1997-02-26 | 1997-02-26 | Menetelmä stanoliesterien valmistamiseksi |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99120095A RU99120095A (ru) | 2001-07-27 |
| RU2178795C2 true RU2178795C2 (ru) | 2002-01-27 |
Family
ID=8548283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99120095/04A RU2178795C2 (ru) | 1997-02-26 | 1998-02-25 | Способ получения станоловых эфиров |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20020045773A1 (https=) |
| EP (1) | EP0975656B1 (https=) |
| JP (1) | JP4368949B2 (https=) |
| AT (1) | ATE217320T1 (https=) |
| AU (1) | AU6101798A (https=) |
| CA (1) | CA2280081C (https=) |
| DE (1) | DE69805295T2 (https=) |
| FI (1) | FI107538B (https=) |
| RU (1) | RU2178795C2 (https=) |
| WO (1) | WO1998038206A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999048907A1 (de) * | 1998-03-23 | 1999-09-30 | Cognis Deutschland Gmbh | Verfahren zur herstellung von stanolen |
| CA2267929A1 (en) * | 1999-04-06 | 2000-10-06 | B.C. Chemicals Ltd. | Preparation of saturated phytosterols |
| US6413571B1 (en) * | 1999-10-21 | 2002-07-02 | The Board Of Regents For Oklahoma State University | Sterol esters of conjugated linoleic acids and process for their production |
| JP3774110B2 (ja) | 2000-07-19 | 2006-05-10 | 花王株式会社 | 食用油脂及びその製造法 |
| JP4212278B2 (ja) * | 2001-03-01 | 2009-01-21 | 日本たばこ産業株式会社 | 移植片拒絶反応抑制剤 |
| GB2372990B (en) * | 2001-03-09 | 2003-01-22 | Diarmaid Joseph Long | A process for the manufacture of sterol esters |
| US20060233863A1 (en) * | 2003-02-10 | 2006-10-19 | Enzymotec Ltd. | Oils enriched with diacylglycerols and phytosterol esters and unit dosage forms thereof for use in therapy |
| AU2005270825B2 (en) * | 2004-08-09 | 2011-07-07 | Enzymotec Ltd. | Food products for diabetics |
| AU2005270831B2 (en) | 2004-08-10 | 2011-08-25 | Enzymotec Ltd. | Mixture of phytosterol ester(s) and 1, 3-diglyceride(s) for use in the treatment of medical conditions |
| US20070031571A1 (en) * | 2005-08-03 | 2007-02-08 | Peter Cremer North America, Lp | Phytosterol esters |
| US20070148311A1 (en) * | 2005-12-22 | 2007-06-28 | Bunge Oils, Inc. | Phytosterol esterification product and method of make same |
| EP1815745A1 (en) | 2006-02-03 | 2007-08-08 | Friesland Brands B.V. | Cholesterol-lowering dairy products and methods for their preparation |
| DE102006041302A1 (de) * | 2006-03-08 | 2007-09-13 | Cognis Ip Management Gmbh | Sterolester mit kurzkettigen Fettsäuren |
| EP1991070A2 (de) * | 2006-03-08 | 2008-11-19 | Cognis IP Management GmbH | Sterolhaltige pulver |
| EP2318426B1 (en) * | 2008-07-25 | 2014-07-02 | Raisio Nutrition Ltd. | Effective hydrogenation process |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4428885A (en) * | 1980-09-01 | 1984-01-31 | The Nisshin Oil Mills, Ltd. | Esterification reaction products |
| RU2095367C1 (ru) * | 1991-05-03 | 1997-11-10 | Райсион Техтаат ой АБ | Вещество, понижающее уровень холестерина в сыворотке крови, и способ его получения |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0914329B1 (en) * | 1996-07-05 | 2003-05-21 | Unilever N.V. | Method of manufacturing an ester mixture |
| FI107015B (fi) * | 1996-08-09 | 2001-05-31 | Raisio Benecol Oy | Kasvistanolirasvahappoestereiden seos ja sen käyttö sekä elintarvike |
| DK1298194T3 (da) | 1997-08-22 | 2006-11-27 | Unilever Nv | Staniolholdige sammensætninger |
-
1997
- 1997-02-26 FI FI970802A patent/FI107538B/fi not_active IP Right Cessation
-
1998
- 1998-02-25 JP JP53734698A patent/JP4368949B2/ja not_active Expired - Fee Related
- 1998-02-25 WO PCT/FI1998/000166 patent/WO1998038206A1/en not_active Ceased
- 1998-02-25 AU AU61017/98A patent/AU6101798A/en not_active Abandoned
- 1998-02-25 CA CA002280081A patent/CA2280081C/en not_active Expired - Fee Related
- 1998-02-25 AT AT98905436T patent/ATE217320T1/de active
- 1998-02-25 EP EP98905436A patent/EP0975656B1/en not_active Expired - Lifetime
- 1998-02-25 US US09/367,836 patent/US20020045773A1/en not_active Abandoned
- 1998-02-25 DE DE69805295T patent/DE69805295T2/de not_active Expired - Lifetime
- 1998-02-25 RU RU99120095/04A patent/RU2178795C2/ru not_active IP Right Cessation
-
2002
- 2002-09-05 US US10/234,138 patent/US6855837B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4428885A (en) * | 1980-09-01 | 1984-01-31 | The Nisshin Oil Mills, Ltd. | Esterification reaction products |
| RU2095367C1 (ru) * | 1991-05-03 | 1997-11-10 | Райсион Техтаат ой АБ | Вещество, понижающее уровень холестерина в сыворотке крови, и способ его получения |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030004361A1 (en) | 2003-01-02 |
| EP0975656B1 (en) | 2002-05-08 |
| CA2280081A1 (en) | 1998-09-03 |
| US6855837B2 (en) | 2005-02-15 |
| CA2280081C (en) | 2007-12-18 |
| FI970802A0 (fi) | 1997-02-26 |
| JP4368949B2 (ja) | 2009-11-18 |
| WO1998038206A1 (en) | 1998-09-03 |
| JP2001516344A (ja) | 2001-09-25 |
| US20020045773A1 (en) | 2002-04-18 |
| ATE217320T1 (de) | 2002-05-15 |
| FI970802L (fi) | 1998-08-27 |
| DE69805295T2 (de) | 2002-08-29 |
| EP0975656A1 (en) | 2000-02-02 |
| AU6101798A (en) | 1998-09-18 |
| DE69805295D1 (de) | 2002-06-13 |
| FI107538B (fi) | 2001-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130226 |