JP2017519792A5 - - Google Patents
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- Publication number
- JP2017519792A5 JP2017519792A5 JP2016575912A JP2016575912A JP2017519792A5 JP 2017519792 A5 JP2017519792 A5 JP 2017519792A5 JP 2016575912 A JP2016575912 A JP 2016575912A JP 2016575912 A JP2016575912 A JP 2016575912A JP 2017519792 A5 JP2017519792 A5 JP 2017519792A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrogenation
- ethylene glycol
- product composition
- formaldehyde
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000197 pyrolysis Methods 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 235000000346 sugar Nutrition 0.000 claims description 6
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 4
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229940015043 glyoxal Drugs 0.000 claims description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 229910000929 Ru alloy Inorganic materials 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 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 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 229930182830 galactose Natural products 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229940120731 pyruvaldehyde Drugs 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 150000008163 sugars Chemical class 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims 1
- 238000005979 thermal decomposition reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14174976 | 2014-06-30 | ||
| EP14174972.1 | 2014-06-30 | ||
| EP14174976.2 | 2014-06-30 | ||
| EP14174972 | 2014-06-30 | ||
| PCT/EP2015/064741 WO2016001169A1 (en) | 2014-06-30 | 2015-06-29 | Process for the preparation of ethylene glycol from sugars |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017519792A JP2017519792A (ja) | 2017-07-20 |
| JP2017519792A5 true JP2017519792A5 (enExample) | 2018-11-08 |
| JP6861032B2 JP6861032B2 (ja) | 2021-04-21 |
Family
ID=53487377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016575912A Active JP6861032B2 (ja) | 2014-06-30 | 2015-06-29 | 糖からエチレングリコールを製造する方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10077222B2 (enExample) |
| EP (1) | EP3160928B1 (enExample) |
| JP (1) | JP6861032B2 (enExample) |
| KR (1) | KR102044453B1 (enExample) |
| CN (1) | CN106795079A (enExample) |
| AU (1) | AU2015282666B2 (enExample) |
| BR (1) | BR112016030694B1 (enExample) |
| CA (1) | CA2952535C (enExample) |
| ES (1) | ES2962507T3 (enExample) |
| MX (1) | MX387642B (enExample) |
| PL (1) | PL3160928T3 (enExample) |
| TW (1) | TWI660936B (enExample) |
| WO (1) | WO2016001169A1 (enExample) |
| ZA (1) | ZA201608381B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3010750C (en) * | 2016-01-07 | 2023-12-12 | Haldor Topsoe A/S | Process for the preparation of ethylene glycol from sugars |
| EP3414218A1 (en) * | 2016-02-08 | 2018-12-19 | Shell International Research Maatschappij B.V. | Process for the hydrogenation of glycolaldehyde |
| CN108602738A (zh) * | 2016-02-09 | 2018-09-28 | 国际壳牌研究有限公司 | 制造亚烷基二醇的方法 |
| CA3026268A1 (en) * | 2016-06-03 | 2017-12-07 | Iowa Corn Promotion Board | Continuous processes for the highly selective conversion of aldohexose-yielding carbohydrate to ethylene glycol |
| DK3472125T3 (da) | 2016-06-16 | 2021-01-18 | Haldor Topsoe As | Termolytisk fragmentering af sukre |
| EA036685B1 (ru) * | 2016-06-22 | 2020-12-08 | Хальдор Топсёэ А/С | Термолитическая фрагментация сахаров |
| CN108070079A (zh) * | 2016-11-09 | 2018-05-25 | 可口可乐公司 | 生物基meg和pet组合物以及制造它们的方法 |
| CN108070075A (zh) | 2016-11-09 | 2018-05-25 | 可口可乐公司 | 生物基meg和聚酯纤维组合物以及制造它们的方法 |
| KR102591904B1 (ko) | 2016-11-24 | 2023-10-20 | 토프쉐 에이/에스 | 글리콜산 및/또는 글리콜레이트의 생성 방법 및 시스템 |
| WO2018104508A1 (en) | 2016-12-08 | 2018-06-14 | Haldor Topsøe A/S | Production of glycolaldehyde by thermolytic fragmentation |
| CN109971803B (zh) * | 2017-12-28 | 2022-04-05 | 中国科学院天津工业生物技术研究所 | 一种l-赤藓酮糖和赤藓糖醇生产方法 |
| CN108610244B (zh) * | 2018-06-13 | 2020-05-15 | 北京大学 | 一种从醛糖制备乙二醛的方法 |
| EP4186884A1 (en) | 2018-07-16 | 2023-05-31 | Topsoe A/S | Thermolytic fragmentation of sugars using resistance heating |
| CN113631678B (zh) * | 2019-01-11 | 2023-09-08 | 阿彻丹尼尔斯米德兰公司 | 用于具有羰基碳原子的化合物选择性氢化的方法和催化剂 |
| CN111686747B (zh) * | 2019-03-15 | 2023-03-21 | 北京化工大学 | 葡萄糖氢解反应目标产物为二元醇的催化剂的制备方法 |
| JP2024521177A (ja) | 2021-05-28 | 2024-05-28 | トプソー・アクチエゼルスカベット | 含酸素化合物混合物の部分凝縮方法 |
| WO2024008924A1 (en) | 2022-07-08 | 2024-01-11 | Topsoe A/S | Process for condensing oxygenate mixtures |
| CN120513267A (zh) | 2022-12-22 | 2025-08-19 | 托普索公司 | 生产聚酯的方法 |
| CN120435450A (zh) | 2022-12-22 | 2025-08-05 | 托普索公司 | 包含乙二醇的经纯化的生物质基组合物及其生产聚酯的用途 |
| WO2024133660A1 (en) | 2022-12-22 | 2024-06-27 | Topsoe A/S | Purified biomass based compositions comprising ethylene glycol and use thereof to produce a polyester |
| CN116768843B (zh) * | 2023-05-06 | 2025-08-01 | 中国科学院合肥物质科学研究院 | 乙醇醛二聚体的制备方法 |
| EP4545645A1 (de) | 2023-10-27 | 2025-04-30 | Annikki GmbH | Verfahren zur herstellung einer wässerigen lösung enthaltend glycolsäure |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200765A (en) | 1976-09-17 | 1980-04-29 | National Distillers And Chemical Corporation | Glycol aldehyde and ethylene glycol processes |
| DE2861830D1 (en) | 1977-12-16 | 1982-07-01 | Monsanto Co | Hydroformylation of formaldehyde with rhodium catalyst |
| US4317946A (en) * | 1980-06-27 | 1982-03-02 | The Halcon Sd Group, Inc. | Process for producing ethylene glycol via catalytic hydrogenation of glycolaldehyde |
| US4321414A (en) * | 1980-08-26 | 1982-03-23 | The Halcon Sd Group, Inc. | Catalytic hydrogenation of glycolaldehyde to produce ethylene glycol |
| US4476331A (en) * | 1982-02-11 | 1984-10-09 | Ethyl Corporation | Two stage hydrogenolysis of carbohydrate to glycols using sulfide modified ruthenium catalyst in second stage |
| US4496781A (en) | 1984-04-05 | 1985-01-29 | The Halcon Sd Group, Inc. | Process for the production of ethylene glycol through the hydroformylation of glycol aldehyde |
| US5210337A (en) | 1988-12-15 | 1993-05-11 | Hoechst Celanese Corporation | Formaldehyde resistant catalyst for hydrogenation and hydrogenolysis of aldehydes, acetals, and esters |
| US5252188A (en) | 1990-03-26 | 1993-10-12 | Red Arrow Products Company, Inc. | Process for producing hydroxyacetaldehyde |
| DE4023255A1 (de) * | 1990-07-21 | 1992-01-23 | Basf Ag | Verfahren zur herstellung von glykolen, insbesondere propylenglykol aus formaldehyd |
| FR2789683B1 (fr) | 1999-02-17 | 2002-02-15 | Roquette Freres | Procede continu de preparation d'un ose hydrogene de haute purete par hydrogenation catalytique |
| CA2326471A1 (en) * | 2000-11-20 | 2002-05-20 | Resource Transforms International Ltd. | Production of glycolaldehyde by hydrous thermolysis of sugars |
| US6900361B2 (en) * | 2001-05-08 | 2005-05-31 | Battelle Memorial Institute | Process for lactose conversion to polyols |
| CN1762938A (zh) * | 2005-09-21 | 2006-04-26 | 徐昌洪 | 氢化裂解法生产乙二醇及低级多元醇的方法 |
| AR063358A1 (es) | 2006-10-23 | 2009-01-21 | Archer Daniels Midland Co | Mejora de la selectividad en la hidrogenolisis de glicerol |
| US8177980B2 (en) | 2007-11-09 | 2012-05-15 | Archer Daniels Midland Company | Separation of a mixture of polyhydric alcohols |
| CN101735014B (zh) | 2008-11-26 | 2013-07-24 | 中国科学院大连化学物理研究所 | 一种多羟基化合物制乙二醇的方法 |
| CN102190562B (zh) * | 2010-03-17 | 2014-03-05 | 中国科学院大连化学物理研究所 | 一种多羟基化合物制乙二醇的方法 |
| CN101781168A (zh) | 2010-03-18 | 2010-07-21 | 西安近代化学研究所 | 二元醇和多元醇的合成方法 |
| CN103402955B (zh) | 2011-03-14 | 2016-02-10 | 阿彻丹尼尔斯米德兰德公司 | 用于产生生物衍生的丙二醇的改进的方法 |
| US8222463B2 (en) | 2011-07-28 | 2012-07-17 | Uop Llc | Process for generation of polyols from saccharide containing feedstock |
| WO2013015996A2 (en) * | 2011-07-28 | 2013-01-31 | Uop Llc | Generation of polyols from saccharide containing feedstock |
| US9767173B2 (en) | 2012-10-22 | 2017-09-19 | Workday, Inc. | Systems and methods for interest-driven data sharing in interest-driven business intelligence systems |
| TWI630197B (zh) | 2013-02-27 | 2018-07-21 | 丹麥商哈爾德杜薩公司 | 從包含低分子量羰基化合物之組成物移除甲醛的方法 |
| DK3145902T3 (en) | 2014-05-19 | 2018-10-01 | Iowa Corn Promotion Board | PROCEDURE FOR CONTINUOUS PREPARATION OF ETHYLENGYLYCOL FROM CARBOHYDRATES |
-
2015
- 2015-06-29 WO PCT/EP2015/064741 patent/WO2016001169A1/en not_active Ceased
- 2015-06-29 PL PL15731382.6T patent/PL3160928T3/pl unknown
- 2015-06-29 US US15/322,680 patent/US10077222B2/en active Active
- 2015-06-29 AU AU2015282666A patent/AU2015282666B2/en active Active
- 2015-06-29 CN CN201580035793.3A patent/CN106795079A/zh active Pending
- 2015-06-29 CA CA2952535A patent/CA2952535C/en active Active
- 2015-06-29 EP EP15731382.6A patent/EP3160928B1/en active Active
- 2015-06-29 MX MX2016017154A patent/MX387642B/es unknown
- 2015-06-29 KR KR1020177001266A patent/KR102044453B1/ko active Active
- 2015-06-29 BR BR112016030694-5A patent/BR112016030694B1/pt active IP Right Grant
- 2015-06-29 ES ES15731382T patent/ES2962507T3/es active Active
- 2015-06-29 JP JP2016575912A patent/JP6861032B2/ja active Active
- 2015-06-30 TW TW104121106A patent/TWI660936B/zh active
-
2016
- 2016-12-05 ZA ZA2016/08381A patent/ZA201608381B/en unknown
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