IE86139B1 - Low temperature, single solvent process for the production of sucrose-6-ester - Google Patents
Low temperature, single solvent process for the production of sucrose-6-ester Download PDFInfo
- Publication number
- IE86139B1 IE86139B1 IE20100653A IE20100653A IE86139B1 IE 86139 B1 IE86139 B1 IE 86139B1 IE 20100653 A IE20100653 A IE 20100653A IE 20100653 A IE20100653 A IE 20100653A IE 86139 B1 IE86139 B1 IE 86139B1
- Authority
- IE
- Ireland
- Prior art keywords
- sucrose
- reaction mixture
- ester
- polar aprotic
- aprotic solvent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 86
- 239000002904 solvent Substances 0.000 title description 28
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000011541 reaction mixture Substances 0.000 claims abstract description 82
- 239000005720 sucrose Substances 0.000 claims abstract description 81
- 229930006000 Sucrose Natural products 0.000 claims abstract description 79
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract description 78
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 64
- 238000005917 acylation reaction Methods 0.000 claims abstract description 47
- 230000010933 acylation Effects 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 239000004376 Sucralose Substances 0.000 claims abstract description 26
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 claims abstract description 26
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- 238000004821 distillation Methods 0.000 claims abstract description 13
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- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 5
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- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical group CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims description 3
- AFHCRQREQZIDSI-OVUASUNJSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate Chemical group O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(=O)C=2C=CC=CC=2)O1 AFHCRQREQZIDSI-OVUASUNJSA-N 0.000 claims description 3
- AFHCRQREQZIDSI-UHFFFAOYSA-N sucrose-6-benzoate Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC(=O)C=2C=CC=CC=2)O1 AFHCRQREQZIDSI-UHFFFAOYSA-N 0.000 claims description 3
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- 238000002360 preparation method Methods 0.000 abstract description 9
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- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000007971 pharmaceutical suspension Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000185 sucrose group Chemical group 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- WVZPYZMQQDNINJ-UHFFFAOYSA-N tributyl(butylstannyloxy)stannane Chemical class CCCC[SnH](CCCC)O[SnH](CCCC)CCCC WVZPYZMQQDNINJ-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25068109P | 2009-10-12 | 2009-10-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE20100653A1 IE20100653A1 (en) | 2011-05-11 |
| IE86139B1 true IE86139B1 (en) | 2013-02-27 |
Family
ID=41565635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE20100653A IE86139B1 (en) | 2009-10-12 | 2010-10-12 | Low temperature, single solvent process for the production of sucrose-6-ester |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8921540B2 (enExample) |
| EP (1) | EP2488541A1 (enExample) |
| JP (1) | JP5726195B2 (enExample) |
| KR (1) | KR20120089718A (enExample) |
| CN (1) | CN102639550B (enExample) |
| GB (1) | GB2474311B (enExample) |
| IE (1) | IE86139B1 (enExample) |
| WO (1) | WO2011045566A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201110520D0 (en) * | 2011-05-10 | 2011-08-03 | Tate & Lyle Technology Ltd | Extraction of carboxylic acids with tin compounds |
| CN104098617A (zh) * | 2013-04-08 | 2014-10-15 | 南京工业大学 | 一种蔗糖-6-乙酸酯的制备方法 |
| US10047038B2 (en) | 2013-11-27 | 2018-08-14 | Tate & Lyle Technology Limited | Waste treatment process |
| US10227367B2 (en) | 2013-12-16 | 2019-03-12 | Tate & Lyle Technology Limited | Chlorination of sucrose-6-esters |
| GB2544217B (en) | 2014-08-08 | 2020-03-25 | Tate & Lyle Tech Ltd | Chlorination of sucrose-6-esters |
| CN104774226A (zh) * | 2015-04-08 | 2015-07-15 | 常州市牛塘化工厂有限公司 | 一种蔗糖-6-乙酯的制备方法 |
| CN105254684B (zh) * | 2015-11-03 | 2019-01-01 | 浙江新和成股份有限公司 | 一种蔗糖-6-乙酸酯的制备方法 |
| GB2551591B (en) | 2016-06-23 | 2019-08-07 | Tate & Lyle Tech Ltd | Liquid-liquid extraction of DMF |
| CN106349300B (zh) * | 2016-08-30 | 2019-02-26 | 安徽金禾实业股份有限公司 | 三氯蔗糖酯化单溶剂反应方法 |
| CN108558962B (zh) | 2018-05-22 | 2020-06-30 | 山东新和成精化科技有限公司 | 一种用于合成蔗糖-6-酯的方法 |
| CN109438533A (zh) * | 2018-12-10 | 2019-03-08 | 安徽金禾实业股份有限公司 | 一种三氯蔗糖生产中高温连续酰化的方法 |
| CN109575069A (zh) * | 2018-12-10 | 2019-04-05 | 安徽金禾实业股份有限公司 | 一种三氯蔗糖生产中催化剂的回收方法 |
| CN112973166B (zh) * | 2019-12-17 | 2024-04-30 | 无锡弘鼎华化工设备有限公司 | 一种三氯蔗糖中和液溶剂的回收装置及方法 |
| CN111574572A (zh) * | 2020-05-22 | 2020-08-25 | 安徽金禾实业股份有限公司 | 一种三氯蔗糖生产中有机锡催化剂连续性制备补充的方法 |
| WO2022051988A1 (zh) | 2020-09-10 | 2022-03-17 | 安徽金禾实业股份有限公司 | 一种蔗糖-6-酯的制备方法 |
| CN112808048B (zh) * | 2021-01-04 | 2022-05-31 | 安徽金禾实业股份有限公司 | 蔗糖-6-酯的制造设备及制造方法 |
| US12434171B2 (en) * | 2021-02-19 | 2025-10-07 | Anhui Jinhe Industrial Co., Ltd. | Production apparatus and production method of sucrose-6-ester |
| EP4163001B1 (en) * | 2021-02-19 | 2024-12-11 | Anhui Jinhe Industrial Co., Ltd. | Production apparatus and production method for sucrose-6-ester |
| CN112933634B (zh) * | 2021-03-04 | 2022-04-08 | 安徽金禾实业股份有限公司 | 一种环列式的蔗糖-6-酯连续生产设备及生产工艺流程 |
| CN112973164B (zh) * | 2021-03-04 | 2022-09-02 | 安徽金禾实业股份有限公司 | 一种高效率的蔗糖6酯连续生产设备及方法 |
| WO2024082175A1 (zh) | 2022-10-19 | 2024-04-25 | 安徽金禾实业股份有限公司 | 一种三氯蔗糖精品的制备方法 |
| CN115894579A (zh) * | 2022-11-17 | 2023-04-04 | 安徽金禾实业股份有限公司 | 一种三氯蔗糖生产中b糖的处理方法 |
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| DE3062467D1 (en) * | 1979-12-20 | 1983-04-28 | Tate & Lyle Plc | Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose |
| EP0043649B1 (en) | 1980-07-08 | 1984-09-12 | TATE & LYLE PUBLIC LIMITED COMPANY | Process for the preparation of 4, 1',6'-trichloro-4,1',6'-trideoxygalactosucrose (tgs) |
| CA1183133A (en) * | 1980-10-28 | 1985-02-26 | Tate & Lyle Public Limited Company | Sweet chlorine-substituted disaccharides |
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| GB8525871D0 (en) * | 1985-10-21 | 1985-11-27 | Tate & Lyle Plc | Chemical compound |
| GB8622345D0 (en) * | 1986-09-17 | 1986-10-22 | Tate & Lyle Plc | Sucrose derivatives |
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| GB8822673D0 (en) * | 1988-09-27 | 1988-11-02 | Tate & Lyle Plc | Selective acylation of sugars |
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| GR910100356A (el) * | 1990-08-27 | 1992-08-31 | Mcneil Ppc Inc | Καταλυόμενη μέ?οδος εστέρος-6-σακχαρόζης. |
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| CA2128820A1 (en) * | 1993-07-27 | 1995-01-28 | Walter G. Gowan, Jr. | Rapidly disintegrating pharmaceutical dosage form and process for preparation thereof |
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| US6890581B2 (en) * | 2002-04-05 | 2005-05-10 | Tate & Lyle Public Limited Company | Methods for buffer stabilized aqueous deacylation |
| US20040030124A1 (en) * | 2002-08-06 | 2004-02-12 | Catani Steven J. | Process for recovering chlorosucrose compounds |
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| US20060188629A1 (en) * | 2005-01-21 | 2006-08-24 | Greg Liesen | Method for the purification of sucralose |
| US20090105470A1 (en) * | 2005-02-22 | 2009-04-23 | Pharmed Medicare Private Limited , A Corporation | Tin Mediated Regioselective Synthesis of Sucrose-6-Esters |
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| KR20080016826A (ko) | 2005-06-01 | 2008-02-22 | 팜드 메디케어 프리베이트 리미티드 | 용매 추출에 의한 염소화 수크로스 유도체의 정제 방법 |
| US20060276639A1 (en) | 2005-06-01 | 2006-12-07 | Healthy Brands, Llc | Conversion of sucralose-6-ester to sucralose |
| US20100197906A1 (en) | 2005-06-06 | 2010-08-05 | Pharmed Medicare Private Limited | Method for purification of chlorinated sucrose derivatives from reaction mixture by chromatography |
| CN101253189A (zh) | 2005-08-30 | 2008-08-27 | 法马德医疗保险私人有限公司 | 基于从反应混合物中直接萃取到有机溶剂中随后蒸除溶剂的纯化三氯半乳蔗糖的方法 |
| US20070100139A1 (en) * | 2005-10-31 | 2007-05-03 | Healthy Brands, Llc | Methods for chlorinating sucrose-6-ester |
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| CN100418976C (zh) * | 2006-04-03 | 2008-09-17 | 广州科宏食品添加物有限公司 | 一种三氯蔗糖的制备方法 |
| GB0702854D0 (en) | 2007-01-09 | 2007-03-28 | Tate & Lyle Plc | Method for the synthesis of sucrose-6-esters |
| US20090076261A1 (en) * | 2007-09-13 | 2009-03-19 | Polymed Therapeutics, Inc. | Novel process for preparing sucrose-6-esters |
-
2009
- 2009-11-20 GB GB0920385.2A patent/GB2474311B/en active Active
-
2010
- 2010-10-11 US US12/901,808 patent/US8921540B2/en active Active
- 2010-10-12 CN CN201080054223.6A patent/CN102639550B/zh active Active
- 2010-10-12 JP JP2012532660A patent/JP5726195B2/ja not_active Expired - Fee Related
- 2010-10-12 KR KR1020127012141A patent/KR20120089718A/ko not_active Ceased
- 2010-10-12 WO PCT/GB2010/001904 patent/WO2011045566A1/en not_active Ceased
- 2010-10-12 EP EP10766092A patent/EP2488541A1/en not_active Withdrawn
- 2010-10-12 IE IE20100653A patent/IE86139B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2474311B (en) | 2012-10-17 |
| EP2488541A1 (en) | 2012-08-22 |
| GB0920385D0 (en) | 2010-01-06 |
| KR20120089718A (ko) | 2012-08-13 |
| CN102639550A (zh) | 2012-08-15 |
| JP5726195B2 (ja) | 2015-05-27 |
| US8921540B2 (en) | 2014-12-30 |
| IE20100653A1 (en) | 2011-05-11 |
| GB2474311A (en) | 2011-04-13 |
| CN102639550B (zh) | 2016-01-27 |
| JP2013507349A (ja) | 2013-03-04 |
| WO2011045566A1 (en) | 2011-04-21 |
| US20110087018A1 (en) | 2011-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |