AU762975B2 - Method for producing phytosterols from reduced quantities of methanol by crystallization - Google Patents
Method for producing phytosterols from reduced quantities of methanol by crystallization Download PDFInfo
- Publication number
- AU762975B2 AU762975B2 AU45411/00A AU4541100A AU762975B2 AU 762975 B2 AU762975 B2 AU 762975B2 AU 45411/00 A AU45411/00 A AU 45411/00A AU 4541100 A AU4541100 A AU 4541100A AU 762975 B2 AU762975 B2 AU 762975B2
- Authority
- AU
- Australia
- Prior art keywords
- methanol
- sterols
- phytosterols
- crystallization
- weight
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 78
- 229940068065 phytosterols Drugs 0.000 title claims abstract description 11
- 238000002425 crystallisation Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 11
- 230000008025 crystallization Effects 0.000 title description 10
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 12
- 229930182558 Sterol Natural products 0.000 claims description 32
- 235000003702 sterols Nutrition 0.000 claims description 32
- 150000003432 sterols Chemical class 0.000 claims description 31
- 240000002791 Brassica napus Species 0.000 claims description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 4
- 244000068988 Glycine max Species 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 4
- -1 fatty acid esters Chemical class 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 description 8
- 238000005809 transesterification reaction Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229940083492 sitosterols Drugs 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- 235000019149 tocopherols Nutrition 0.000 description 2
- 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 2
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000012886 linear function Methods 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19916034 | 1999-04-09 | ||
| DE19916034A DE19916034C1 (de) | 1999-04-09 | 1999-04-09 | Verfahren zur Gewinnung von Phytosterinen |
| PCT/EP2000/002849 WO2000061603A1 (de) | 1999-04-09 | 2000-03-31 | Verfahren zur gewinnung von phytosterinen durch kristallisation aus verminderten mengen methanols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU4541100A AU4541100A (en) | 2000-11-14 |
| AU762975B2 true AU762975B2 (en) | 2003-07-10 |
Family
ID=7904011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU45411/00A Ceased AU762975B2 (en) | 1999-04-09 | 2000-03-31 | Method for producing phytosterols from reduced quantities of methanol by crystallization |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7244856B2 (https=) |
| EP (1) | EP1169335B1 (https=) |
| JP (1) | JP4796695B2 (https=) |
| AT (1) | ATE255124T1 (https=) |
| AU (1) | AU762975B2 (https=) |
| CA (1) | CA2369977C (https=) |
| DE (2) | DE19916034C1 (https=) |
| NZ (1) | NZ514667A (https=) |
| WO (1) | WO2000061603A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001032682A1 (en) * | 1999-11-04 | 2001-05-10 | Kao Corporation | Process for the purification of phytosterol from fatty acids and their esters |
| DE10038442A1 (de) | 2000-08-07 | 2002-02-21 | Cognis Deutschland Gmbh | Verfahren zur Gewinnung von Sterinen aus fettsäurehaltigen Rückständen |
| DE10038456A1 (de) * | 2000-08-07 | 2002-02-21 | Cognis Deutschland Gmbh | Verfahren zur Gewinnung von Sterinen |
| DE10038457B4 (de) * | 2000-08-07 | 2008-09-25 | Cognis Ip Management Gmbh | Verfahren zur Gewinnung von Sterinen und Tocopherolen |
| US7144595B2 (en) * | 2001-11-16 | 2006-12-05 | Brandeis University | Prepared foods containing triglyceride-recrystallized non-esterified phytosterols |
| CN101331149A (zh) * | 2005-11-08 | 2008-12-24 | 科学与工业研究会 | 从植物油的除臭机馏出物制备高纯度植物甾醇的方法 |
| ES2425149T3 (es) | 2005-11-25 | 2013-10-11 | Morinaga Milk Industry Co., Ltd. | Extracto de Aloe vera, método de preparación de extracto de Aloe vera y agente mejorador de la hiperglucemia |
| FI20070137A0 (fi) * | 2007-02-15 | 2007-02-15 | Raisio Benecol Oy | Menetelmä rasvahappojen, hartsihappojen ja sterolien eristämiseksi mäntyöljypiestä |
| US7790495B2 (en) * | 2007-10-26 | 2010-09-07 | International Business Machines Corporation | Optoelectronic device with germanium photodetector |
| WO2009113935A1 (en) * | 2008-03-10 | 2009-09-17 | Sunpine Ab | Recovery of phytosterols from residual vegetable oil streams |
| PL2635592T5 (pl) | 2010-11-03 | 2025-09-08 | Verbio Se | Sposób otrzymywania fitosteroli i/lub tokoferoli z pozostałości po destylacji estrów olejów roślinnych, korzystnie z pozostałości po destylacji z transestryfikacji olejów roślinnych |
| US10398162B2 (en) | 2014-03-20 | 2019-09-03 | Morinaga Milk Industry Co., Ltd. | Method for manufacturing aloe extract, and aloe extract |
| WO2019124075A1 (ja) | 2017-12-19 | 2019-06-27 | 森永乳業株式会社 | アロエ粉末の製造方法 |
| EP4034620A1 (en) | 2019-09-27 | 2022-08-03 | Basf Se | Process for the production of sterols and/or tocopherols with recovery of by-products |
| CA3146079A1 (en) | 2019-09-27 | 2021-04-01 | Valerie Eychenne | Process for the production and purification of sterols |
| CA3146266A1 (en) | 2019-09-27 | 2021-04-01 | Basf Se | Process for the purification of phytosterol |
| JPWO2022045354A1 (https=) | 2020-08-31 | 2022-03-03 | ||
| FI131000B1 (en) | 2020-12-01 | 2024-07-29 | Forchem Oyj | Procedure for cleaning sterols from tallow pitch |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB635497A (en) * | 1946-08-07 | 1950-04-12 | Distillation Products Inc | An improved process for separating sterols from oil concentrates |
| US5424457A (en) * | 1994-05-27 | 1995-06-13 | Eastman Chemical Company | Process for the production of sterol and tocopherol concentrates |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI65440C (fi) * | 1981-07-21 | 1984-05-10 | Kaukas Ab Oy | Foerfarande foer separering av beta-sitosterol med en laog alfa-sitosterolhalt |
| JPS6042495A (ja) * | 1983-08-17 | 1985-03-06 | 日清製油株式会社 | 油脂脱臭留出物のメチルエステル化法 |
| JPS6150996A (ja) * | 1984-08-16 | 1986-03-13 | Daicel Chem Ind Ltd | ステロ−ルの製造方法 |
| EP0333472B1 (en) * | 1988-03-16 | 1997-10-08 | PALM OIL RESEARCH & DEVELOPMENT BOARD | Production of high concentration tocopherols and tocotrienols from palm oil by-products |
| DE4228476C2 (de) * | 1992-08-27 | 2002-05-02 | Cognis Deutschland Gmbh | Verfahren zum Gewinnen von Tocopherol und/oder Sterin |
| US5487817A (en) * | 1993-02-11 | 1996-01-30 | Hoffmann-La Roche Inc. | Process for tocopherols and sterols from natural sources |
| RU2165431C2 (ru) * | 1994-09-29 | 2001-04-20 | Дзе Юниверсити оф Бритиш Колумбия | Способ выделения композиции фитостеролов, композиции, терапевтический продукт |
-
1999
- 1999-04-09 DE DE19916034A patent/DE19916034C1/de not_active Expired - Fee Related
-
2000
- 2000-03-31 DE DE50004569T patent/DE50004569D1/de not_active Expired - Lifetime
- 2000-03-31 AU AU45411/00A patent/AU762975B2/en not_active Ceased
- 2000-03-31 CA CA002369977A patent/CA2369977C/en not_active Expired - Lifetime
- 2000-03-31 WO PCT/EP2000/002849 patent/WO2000061603A1/de not_active Ceased
- 2000-03-31 JP JP2000611545A patent/JP4796695B2/ja not_active Expired - Lifetime
- 2000-03-31 AT AT00926783T patent/ATE255124T1/de active
- 2000-03-31 NZ NZ514667A patent/NZ514667A/xx not_active IP Right Cessation
- 2000-03-31 EP EP00926783A patent/EP1169335B1/de not_active Expired - Lifetime
-
2004
- 2004-07-22 US US10/896,486 patent/US7244856B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB635497A (en) * | 1946-08-07 | 1950-04-12 | Distillation Products Inc | An improved process for separating sterols from oil concentrates |
| US5424457A (en) * | 1994-05-27 | 1995-06-13 | Eastman Chemical Company | Process for the production of sterol and tocopherol concentrates |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4541100A (en) | 2000-11-14 |
| ATE255124T1 (de) | 2003-12-15 |
| JP2002542161A (ja) | 2002-12-10 |
| WO2000061603A1 (de) | 2000-10-19 |
| DE19916034C1 (de) | 2000-08-03 |
| CA2369977A1 (en) | 2000-10-19 |
| DE50004569D1 (de) | 2004-01-08 |
| NZ514667A (en) | 2002-12-20 |
| US7244856B2 (en) | 2007-07-17 |
| CA2369977C (en) | 2009-06-16 |
| EP1169335A1 (de) | 2002-01-09 |
| US20040260104A1 (en) | 2004-12-23 |
| JP4796695B2 (ja) | 2011-10-19 |
| EP1169335B1 (de) | 2003-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK6 | Application lapsed section 142(2)(f)/reg. 8.3(3) - pct applic. not entering national phase | ||
| TH | Corrigenda |
Free format text: IN VOL 15, NO 5, PAGE(S) 796-799 UNDER THE HEADING APPLICATIONS LAPSED, REFUSED OR WITHDRAWN PLEASE DELETE ALL REFERENCE TO APPLICATION NO. 45411/00 |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| TC | Change of applicant's name (sec. 104) |
Owner name: COGNIS DEUTSCHLAND GMBH AND CO. KG Free format text: FORMER NAME: COGNIS DEUTSCHLAND GMBH |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |