JP2016516014A5 - - Google Patents
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- Publication number
- JP2016516014A5 JP2016516014A5 JP2015561383A JP2015561383A JP2016516014A5 JP 2016516014 A5 JP2016516014 A5 JP 2016516014A5 JP 2015561383 A JP2015561383 A JP 2015561383A JP 2015561383 A JP2015561383 A JP 2015561383A JP 2016516014 A5 JP2016516014 A5 JP 2016516014A5
- Authority
- JP
- Japan
- Prior art keywords
- triflate
- iii
- hexitol
- mole percent
- bismuth
- 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.)
- Granted
Links
- FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 4
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 1
- HZXJVDYQRYYYOR-UHFFFAOYSA-K Scandium(III) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N Trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 1
- FKOASGGZYSYPBI-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)alumanyl trifluoromethanesulfonate Chemical compound [Al+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F FKOASGGZYSYPBI-UHFFFAOYSA-K 0.000 claims 1
- UCYRAEIHXSVXPV-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)indiganyl trifluoromethanesulfonate Chemical compound [In+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F UCYRAEIHXSVXPV-UHFFFAOYSA-K 0.000 claims 1
- RBGLVWCAGPITBS-UHFFFAOYSA-L bis(trifluoromethylsulfonyloxy)tin Chemical compound [Sn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F RBGLVWCAGPITBS-UHFFFAOYSA-L 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 229910052733 gallium Inorganic materials 0.000 claims 1
- 239000011968 lewis acid catalyst Substances 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Claims (3)
- ヘキシトール及びモノアンヒドロヘキシトールの１つ又は両方からイソヘキシドを生成するための方法であって、１４０℃〜１６０℃の温度で１時間〜３時間の期間にわたり、減圧下で、脱水の過程で生成物混合物から水を継続的に除去して、ビスマス（ＩＩＩ）トリフラート、ガリウム（ＩＩＩ）トリフラート、スカンジウム（ＩＩＩ）トリフラート、アルミニウムトリフラート、インジウム（ＩＩＩ）トリフラート、スズ（ＩＩ）トリフラート、およびこれらの２種以上の組合せからなる群から選択される０．００５モルパーセント〜０．１モルパーセントの均質なルイス酸触媒と、上記開始材料とを接触させることを含む、方法。
- 前記ヘキシトールはソルビトールである、請求項１に記載の方法。
- 前記ヘキシトールはマンニトールであり、前記触媒はビスマス（ＩＩＩ）トリフラートである、請求項１に記載の方法。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361772642P | 2013-03-05 | 2013-03-05 | |
| US61/772,642 | 2013-03-05 | ||
| PCT/US2014/017563 WO2014137619A1 (en) | 2013-03-05 | 2014-02-21 | Process for acid dehydration of sugar alcohols |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016516014A JP2016516014A (ja) | 2016-06-02 |
| JP2016516014A5 true JP2016516014A5 (ja) | 2017-03-02 |
| JP6267240B2 JP6267240B2 (ja) | 2018-01-24 |
Family
ID=51491780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015561383A Expired - Fee Related JP6267240B2 (ja) | 2013-03-05 | 2014-02-21 | 糖アルコールの酸脱水のための方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9630974B2 (ja) |
| EP (1) | EP2964743B1 (ja) |
| JP (1) | JP6267240B2 (ja) |
| KR (1) | KR20150123923A (ja) |
| CN (1) | CN105026542A (ja) |
| WO (1) | WO2014137619A1 (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016137833A1 (en) | 2015-02-24 | 2016-09-01 | Archer Daniel Midland Company | Isoidide manufacture and purification |
| WO2017030684A1 (en) * | 2015-08-14 | 2017-02-23 | Archer Daniels Midland Company | Dehydrative cyclization of pentitols using water-tolerant lewis acid catalysts under mild conditions and derivatives |
| WO2017030685A1 (en) * | 2015-08-14 | 2017-02-23 | Archer Daniels Midland Company | One-pot synthesis of anhydropentitol mono- and diethers |
| WO2017100402A1 (en) * | 2015-12-11 | 2017-06-15 | Archer Daniels Midland Company | One-pot synthesis of anhydropentitol esters from pentitols, catalyzed by water-tolerant lewis acids |
| JP6803703B2 (ja) | 2016-08-29 | 2020-12-23 | 国立大学法人北海道大学 | マンニトールの脱水用固体触媒、およびこの触媒を使用する２，５−ソルビタン及び／又はイソマンニドの製造方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3223734A (en) * | 1961-04-26 | 1965-12-14 | Archer Daniels Midland Co | Process for producing tertiary amines |
| PL193289B1 (pl) * | 1999-11-12 | 2007-01-31 | Univ Gdanski | Sposób otrzymywania mieszaniny anhydroheks |
| CN1446221A (zh) * | 2000-05-26 | 2003-10-01 | 纳幕尔杜邦公司 | 借助于气体净化的脱水糖醇的制造方法 |
| US7439352B2 (en) | 2000-11-01 | 2008-10-21 | Archer-Daniels-Midland Company | Process for the production of anhydrosugar alcohols |
| US6849748B2 (en) | 2000-11-01 | 2005-02-01 | Archer-Daniels-Midland Company | Process for the production of anhydrosugar alcohols |
| US7772412B2 (en) * | 2006-01-26 | 2010-08-10 | Battelle Memorial Institute | Methods for dehydration of sugars and sugar alcohols |
| US7728156B2 (en) * | 2006-01-26 | 2010-06-01 | Battelle Memorial Institute | Method of performing sugar dehydration and catalyst treatment |
| EP1999134B1 (en) * | 2006-03-09 | 2015-11-11 | Archer-Daniels-Midland Company | Process for the production of anhydrosugar alcohols |
| CN101675055B (zh) | 2007-04-06 | 2013-06-26 | 苏德-化学公司 | 山梨糖醇的转化方法 |
| KR101172615B1 (ko) * | 2010-12-15 | 2012-08-08 | 주식회사 삼양제넥스 | 무수당 알코올의 증류 방법 및 이를 이용한 무수당 알코올의 제조 방법 |
| KR20140025379A (ko) * | 2011-03-10 | 2014-03-04 | 아처 다니엘 미드랜드 캄파니 | 당, 당 알콜 및 관련 탈수 생성물의 개선된 정량 분석 방법 |
| IN2014DN06491A (ja) | 2012-01-10 | 2015-06-12 | Archer Daniels Midland Co | |
| EP2825543B1 (en) | 2012-03-12 | 2017-12-20 | Archer Daniels Midland Company | Process for making sugar and/or sugar alcohol dehydration products |
| KR101421514B1 (ko) * | 2012-05-22 | 2014-07-30 | 대구가톨릭대학교산학협력단 | 물에 안정한 루이스 산을 이용한 소르비톨로부터 아이소소바이드의 제조방법 |
-
2014
- 2014-02-21 JP JP2015561383A patent/JP6267240B2/ja not_active Expired - Fee Related
- 2014-02-21 KR KR1020157027290A patent/KR20150123923A/ko not_active Application Discontinuation
- 2014-02-21 CN CN201480010308.2A patent/CN105026542A/zh active Pending
- 2014-02-21 US US14/771,825 patent/US9630974B2/en not_active Expired - Fee Related
- 2014-02-21 WO PCT/US2014/017563 patent/WO2014137619A1/en active Application Filing
- 2014-02-21 EP EP14759625.8A patent/EP2964743B1/en not_active Not-in-force
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