JP2013507349A - スクロース−6−エステルを生成する低温単一溶媒方法 - Google Patents
スクロース−6−エステルを生成する低温単一溶媒方法 Download PDFInfo
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- JP2013507349A JP2013507349A JP2012532660A JP2012532660A JP2013507349A JP 2013507349 A JP2013507349 A JP 2013507349A JP 2012532660 A JP2012532660 A JP 2012532660A JP 2012532660 A JP2012532660 A JP 2012532660A JP 2013507349 A JP2013507349 A JP 2013507349A
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- sucrose
- reaction mixture
- ester
- organotin
- temperature
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- 238000000034 method Methods 0.000 title claims abstract description 85
- 239000002904 solvent Substances 0.000 title description 26
- 239000011541 reaction mixture Substances 0.000 claims abstract description 82
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- 239000005720 sucrose Substances 0.000 claims abstract description 79
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000003880 polar aprotic solvent Substances 0.000 claims abstract description 58
- 238000005917 acylation reaction Methods 0.000 claims abstract description 50
- 230000010933 acylation Effects 0.000 claims abstract description 49
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- 239000004376 Sucralose Substances 0.000 claims abstract description 27
- 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 27
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- JLHADLTXDDGZFX-UHFFFAOYSA-L [[acetyloxy(dibutyl)stannyl]oxy-dibutylstannyl] acetate Chemical group CCCC[Sn](CCCC)(OC(C)=O)O[Sn](CCCC)(CCCC)OC(C)=O JLHADLTXDDGZFX-UHFFFAOYSA-L 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000010923 batch production Methods 0.000 claims description 5
- 238000010924 continuous production Methods 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 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
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- CZFRZPMJNNTNDS-UHFFFAOYSA-L CCCC[Sn](O)(CCCC)O[Sn](CCCC)(CCCC)OC(C)=O Chemical group CCCC[Sn](O)(CCCC)O[Sn](CCCC)(CCCC)OC(C)=O CZFRZPMJNNTNDS-UHFFFAOYSA-L 0.000 claims description 2
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
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- 238000006731 degradation reaction Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
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- 238000006640 acetylation reaction Methods 0.000 description 9
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- 238000009835 boiling Methods 0.000 description 8
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- 238000010791 quenching Methods 0.000 description 8
- 150000003511 tertiary amides Chemical class 0.000 description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
- 239000000010 aprotic solvent Substances 0.000 description 7
- 150000001720 carbohydrates Chemical class 0.000 description 7
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 7
- 229910001887 tin oxide Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
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- 229910052718 tin Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
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- 239000012320 chlorinating reagent Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000003606 tin compounds Chemical class 0.000 description 5
- -1 4,1 ', 6'-trichloro-4,1', 6'-trideoxygalactosucrose ester Chemical class 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
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- 241000894007 species Species 0.000 description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VCZXRQFWGHPRQB-UHFFFAOYSA-N CC(C)CC(C)(C)C.CC(C)CC(C)(C)C Chemical compound CC(C)CC(C)(C)C.CC(C)CC(C)(C)C VCZXRQFWGHPRQB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000244489 Navia Species 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 3
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- 125000004185 ester group Chemical group 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
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- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
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Abstract
【選択図】図1
Description
(a)スクロース、極性非プロトン性溶媒及び有機スズベースのアシル化促進剤を含む第1の反応混合物を準備する工程と、
(b)前記第1の反応混合物から水を除去して、実質的に水を含まない第2の反応混合物を得る工程と、
(c)前記第2の反応混合物にカルボン酸無水物を添加し、第3の反応混合物を得て、それによりスクロース−6−エステルを生成する工程と
を順に含み、
工程(b)中に非極性共溶媒を添加せず、
工程(b)において温度が約80℃を超えない、方法である。
スクロース−6−エステルの調製
スクロースの6−ヒドロキシルの選択的保護は、有機スズベースのアシル化促進剤の存在下、本明細書中に記載の反応条件下で、スクロース−6−エステルを生成するのに十分な温度で十分な時間にわたって、無水極性非プロトン性溶媒中においてスクロースと無水酢酸又は安息香酸無水物等のカルボン酸無水物とを反応させることによって行うことができる。6−エステル基は6位のヒドロキシルを塩素化反応から遮る。したがって、塩素化反応条件に安定であり、得られたスクラロースに影響を与えない条件下で除去することができる任意のエステル基を使用することができる。スクロース−6−アセテートを調製する場合、有機スズベースのアシル化促進剤として例えば1,3−ジアセトキシ−1,1,3,3−テトラブチルジスタンノキサンを、カルボン酸無水物として無水酢酸を使用することができる。スクロース−6−エステルの調製は例えば、O'Brienの米国特許第4,783,526号、Naviaの米国特許第4,950,746号、Simpsonの米国特許第4,889,928号、Neiditchの米国特許第5,023,329号、Walkupの米国特許第5,089,608号、Vernonの米国特許第5,034,551号、Sankeyの特許文献1、Kahnの米国特許第5,440,026号、Clarkの特許文献3及びLiの米国特許出願公開第2007/0227897号(これらの開示は全て参照により本明細書中に援用される)に開示されている。
スクロース−6−エステルのスクラロース−6−エステルへの変換
スクロース−6−エステルをスクラロース−6−エステルへと変換するために、スクロース−6−エステルの4位、1’位及び6’位のヒドロキシルをクロロ基へと変換し、4位の立体化学的配置を反転させる。4位の立体化学的配置の反転を伴う、このエステルの4位、1’位及び6’位のヒドロキシルのクロロ基への変換は、Walkupの米国特許第4,980,463号、Jaiの米国特許出願公開第2006/0205936号及びFryの米国特許出願公開第2007/0100139号(これらの開示は全て参照により本明細書中に援用される)に開示されている。
スクラロース−6−エステルのスクラロースへの変換
得られた混合物は通常、スクラロース及びスクラロース−6−エステルの両方を含む。スクラロース及びスクラロース−6−エステルの混合物をスクラロースへと変換し、得られたスクラロースを当該技術分野で既知の方法によって精製及び単離することができる。スクラロース−6−エステルを加水分解し、スクラロースを単離し、かつ/又はスクラロースを精製する方法は、例えばCataniの米国特許第5,977,349号、同第6,943,248号、同第6,998,480号及び同第7,049,435号、Vernonの米国特許第6,890,581号、El Kabbaniの米国特許第6,809,198号及び同第6,646,121号、Naviaの米国特許第5,298,611号及び同第5,498,709号、並びに米国特許出願公開第2004/0030124号、Liesenの米国特許出願公開第2006/0188629号、Fryの米国特許出願公開第2006/0276639号、El Kabbaniの米国特許出願公開第2007/0015916号、Deshpandeの米国特許出願公開第2007/0160732号、並びにRatnamの米国特許出願公開第2007/0270583号(これらの開示は全て参照により本明細書中に援用される)に開示されている。
DMF N,N−ジメチルホルムアミド
DSDA 1,3−ジアセトキシ−1,1,3,3−テトラブチルジスタンノキサン(ジスタンノキサンジアセテート);(C4H9)2Sn(OAc)−O−Sn(OAc)(C4H9)2
実施例1
本実施例は本発明の方法を実証するものである。
実施例2
本実施例は、より低温の脱水を用いた方法を実証するものである。
実施例3
本実施例は、より低温の脱水を用いた方法を実証するものである。
実施例4
本実施例は、より低温のアセチル化を用いた方法を実証するものである。
実施例5
本実施例は、使用する溶媒を減らし、高い最終濃度のスクローススズ付加物をアセチル化に使用する方法を実証するものである。
実施例6
本実施例は、アセチル化を補助するために共溶媒を添加しない方法を実証するものである。
実施例7
本実施例は、無溶媒DSDAを脱水に使用する方法を実証するものである。
Claims (18)
- (a)スクロース、極性非プロトン性溶媒及び有機スズベースのアシル化促進剤を含む第1の反応混合物を準備する工程と、
(b)前記第1の反応混合物から水を除去して、実質的に水を含まない第2の反応混合物を得る工程と、
(c)前記第2の反応混合物にカルボン酸無水物を添加し、第3の反応混合物を得て、それによりスクロース−6−エステルを生成する工程と
を順に含み、
工程(b)中に非極性共溶媒を添加せず、
工程(b)において温度が約80℃を超えない、方法。 - 工程(b)中、水の除去が減圧で前記極性非プロトン性溶媒とともに水を蒸留することを含む、請求項1に記載の方法。
- 前記第1の反応混合物及び/又は前記第2の反応混合物が、スクロース、前記極性非プロトン性溶媒、前記有機スズベースのアシル化促進剤及び/又はそれらの反応生成物から本質的になる、請求項1又は2に記載の方法。
- 工程(c)中、前記第3の反応混合物を、前記スクロース−6−エステルを生成するのに十分な時間にわたって10℃以下に維持する、請求項1〜3のいずれか一項に記載の方法。
- 工程(b)における温度が約80℃〜約20℃である、請求項1〜4のいずれか一項に記載の方法。
- 工程(b)における温度が約78℃〜約30℃である、請求項1〜5のいずれか一項に記載の方法。
- 工程(b)における温度が約75℃〜約40℃である、請求項1〜6のいずれか一項に記載の方法。
- 工程(b)における温度が約70℃〜約50℃である、請求項1〜7のいずれか一項に記載の方法。
- 前記極性非プロトン性溶媒がN,N−ジメチルホルムアミドである、請求項1〜8のいずれか一項に記載の方法。
- 前記有機スズベースのアシル化促進剤が1,3−ジ(アシルオキシ)−1,1,3,3−テトラ−(ヒドロカルビル)ジスタンノキサンである、請求項1〜9のいずれか一項に記載の方法。
- 前記有機スズベースのアシル化促進剤が1,3−ジアセトキシ−1,1,3,3−テトラブチルジスタンノキサンである、請求項1〜10のいずれか一項に記載の方法。
- 前記有機スズベースのアシル化促進剤が1−アシルオキシ−3−ヒドロキシ−1,1,3,3−テトラ−(ヒドロカルビル)ジスタンノキサンである、請求項1〜9のいずれか一項に記載の方法。
- 前記有機スズベースのアシル化促進剤が1−アセトキシ−3−ヒドロキシ−1,1,3,3−テトラブチルジスタンノキサンである、請求項12に記載の方法。
- 前記カルボン酸無水物が無水酢酸であり、前記スクロース−6−エステルがスクロース−6−アセテートである、請求項1〜13のいずれか一項に記載の方法。
- 前記カルボン酸無水物が安息香酸無水物であり、前記スクロース−6−エステルがスクロース−6−ベンゾエートである、請求項1〜11のいずれか一項に記載の方法。
- バッチプロセスである、請求項1〜15のいずれか一項に記載の方法。
- 連続プロセスである、請求項1〜15のいずれか一項に記載の方法。
- 工程(c)の後に、前記スクロース−6−エステルをスクラロースに変換する更なる工程(単数又は複数)を更に含む、請求項1〜17のいずれか一項に記載の方法。
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US20230295210A1 (en) | 2020-09-10 | 2023-09-21 | Anhui Jinhe Industrial Co., Ltd. | Method for preparing sucrose-6-ester |
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JPH04225993A (ja) * | 1990-04-23 | 1992-08-14 | マクニール−ピーピーシー・インコーポレーテツド | サツカロース−6−エステルの製造法 |
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WO2002010180A1 (en) * | 2000-07-31 | 2002-02-07 | Tate & Lyle Public Limited Company | An improved method for the synthesis of sucrose-6-esters |
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JP5726195B2 (ja) | 2015-05-27 |
US20110087018A1 (en) | 2011-04-14 |
CN102639550B (zh) | 2016-01-27 |
EP2488541A1 (en) | 2012-08-22 |
GB2474311A (en) | 2011-04-13 |
WO2011045566A1 (en) | 2011-04-21 |
US8921540B2 (en) | 2014-12-30 |
GB0920385D0 (en) | 2010-01-06 |
IE20100653A1 (en) | 2011-05-11 |
KR20120089718A (ko) | 2012-08-13 |
IE86139B1 (en) | 2013-02-27 |
CN102639550A (zh) | 2012-08-15 |
GB2474311B (en) | 2012-10-17 |
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