JP2019501193A5 - - Google Patents
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- JP2019501193A5 JP2019501193A5 JP2018535315A JP2018535315A JP2019501193A5 JP 2019501193 A5 JP2019501193 A5 JP 2019501193A5 JP 2018535315 A JP2018535315 A JP 2018535315A JP 2018535315 A JP2018535315 A JP 2018535315A JP 2019501193 A5 JP2019501193 A5 JP 2019501193A5
- Authority
- JP
- Japan
- Prior art keywords
- weight
- reactor
- composition
- oxygen
- hydroxy
- 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.)
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Links
- 238000000034 method Methods 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 21
- 238000005984 hydrogenation reaction Methods 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000013467 fragmentation Methods 0.000 claims description 11
- 238000006062 fragmentation reaction Methods 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000197 pyrolysis Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- 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 1
- 229930091371 Fructose Natural products 0.000 claims 1
- 239000005715 Fructose Substances 0.000 claims 1
- 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 1
- 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 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims 1
- 229910000929 Ru alloy Inorganic materials 0.000 claims 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- 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 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims 1
- 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 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 150000002016 disaccharides Chemical class 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229930182830 galactose Natural products 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 229940015043 glyoxal Drugs 0.000 claims 1
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002772 monosaccharides Chemical class 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229940120731 pyruvaldehyde Drugs 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201600008 | 2016-01-07 | ||
| DKPA201600008 | 2016-01-07 | ||
| PCT/EP2017/050183 WO2017118686A1 (en) | 2016-01-07 | 2017-01-05 | Process for the preparation of ethylene glycol from sugars |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019501193A JP2019501193A (ja) | 2019-01-17 |
| JP2019501193A5 true JP2019501193A5 (enExample) | 2021-03-18 |
| JP6975152B2 JP6975152B2 (ja) | 2021-12-01 |
Family
ID=59273360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018535315A Active JP6975152B2 (ja) | 2016-01-07 | 2017-01-05 | 糖からエチレングリコールを製造する方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US10759726B2 (enExample) |
| EP (1) | EP3400208B1 (enExample) |
| JP (1) | JP6975152B2 (enExample) |
| KR (1) | KR102737311B1 (enExample) |
| CN (1) | CN108473401B (enExample) |
| AU (1) | AU2017205265B2 (enExample) |
| BR (1) | BR112018013543B1 (enExample) |
| CA (1) | CA3010748C (enExample) |
| DK (1) | DK3400208T3 (enExample) |
| MX (1) | MX2018007750A (enExample) |
| PL (1) | PL3400208T3 (enExample) |
| RU (1) | RU2737159C2 (enExample) |
| TW (1) | TWI739786B (enExample) |
| UA (1) | UA123827C2 (enExample) |
| WO (1) | WO2017118686A1 (enExample) |
| ZA (1) | ZA201803648B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102019113135A1 (de) * | 2019-05-17 | 2020-11-19 | Rheinisch-Westfälische Technische Hochschule (Rwth) Aachen | Verfahren zur Herstellung von Glycolen aus Zuckern und Zuckeralkoholen |
| EP4034524A4 (en) | 2019-09-24 | 2023-05-31 | Iowa Corn Promotion Board | METHOD OF RUNNING CONTINUOUS UNMODULATED PROCESSES WITH MULTIPLE CATALYTIC STEPS |
| US11680031B2 (en) | 2020-09-24 | 2023-06-20 | T. EN Process Technology, Inc. | Continuous processes for the selective conversion of aldohexose-yielding carbohydrate to ethylene glycol using low concentrations of retro-aldol catalyst |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2054601C3 (de) * | 1970-11-06 | 1980-02-14 | Ruhrchemie Ag, 4200 Oberhausen- Holten | Verfahren zur Herstellung von zweiwertigen Alkoholen |
| 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 |
| US4321141A (en) * | 1979-06-01 | 1982-03-23 | Corning Glass Works | Method for processing waste |
| 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 |
| 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 |
| US4762817A (en) * | 1986-11-03 | 1988-08-09 | Union Carbide Corporation | Aldehyde hydrogenation catalyst |
| 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 |
| DE4014261A1 (de) | 1990-05-04 | 1991-11-07 | Basf Ag | Expandierbare styrolpolymerisate |
| DE4218282A1 (de) * | 1992-06-03 | 1993-12-09 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| FI102474B (fi) | 1996-12-30 | 1998-12-15 | Neste Oy | Menetelmä moniarvoisten alkoholien valmistamiseksi |
| AU5798199A (en) | 1998-09-04 | 2000-03-27 | E.I. Du Pont De Nemours And Company | Two-stage process for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal |
| 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 |
| AU2002240870A1 (en) * | 2000-12-23 | 2002-07-08 | Degussa Ag | Method for producing alcohols by hydrogenating carbonyl compounds |
| US7663004B2 (en) * | 2002-04-22 | 2010-02-16 | The Curators Of The University Of Missouri | Method of producing lower alcohols from glycerol |
| MXPA06003819A (es) | 2003-10-07 | 2006-08-11 | Shell Int Research | Proceso para la produccion de 1,3-propanodiol por hidrogenacion catalitica de 3-hidroxipropanal en la presencia de un co-catalizador de hidratacion. |
| JP4474419B2 (ja) * | 2003-12-16 | 2010-06-02 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | グリコールアルデヒドの調製方法 |
| US7619119B2 (en) | 2006-06-07 | 2009-11-17 | The Procter & Gamble Company | Processes for converting glycerol to amino alcohols |
| ES2402216T3 (es) | 2006-06-07 | 2013-04-29 | The Procter & Gamble Company | Procesos para convertir glicerol en aminoalcoholes |
| AR063358A1 (es) | 2006-10-23 | 2009-01-21 | Archer Daniels Midland Co | Mejora de la selectividad en la hidrogenolisis de glicerol |
| CN100497274C (zh) * | 2007-01-25 | 2009-06-10 | 中国林业科学研究院林产化学工业研究所 | 一种甘油法制备1,3-丙二醇的方法 |
| FR2925046A1 (fr) | 2007-12-14 | 2009-06-19 | Rhodia Poliamida E Especialidades Ltda | Procede d'obtention d'alcool a partir d'un aldehyde |
| US20140024769A1 (en) | 2012-05-11 | 2014-01-23 | Metabolix, Inc. | Process for making chemical derivatives |
| US8809593B2 (en) * | 2010-02-26 | 2014-08-19 | Council Of Scientific And Industrial Research | Process for preparation of hydroxyacetone or propylene glycol |
| 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 |
| CN102649081B (zh) | 2011-02-25 | 2014-11-26 | 中国石油化工股份有限公司 | 草酸酯加氢制备乙二醇催化剂还原的方法 |
| 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 |
| US8969632B2 (en) | 2012-03-23 | 2015-03-03 | Eastman Chemical Company | Passivation of a homogeneous hydrogenation catalyst for the production of ethylene glycol |
| ITTO20130833A1 (it) | 2013-10-16 | 2015-04-17 | Biochemtex Spa | Procedimento per la produzione di polioli |
| WO2015154258A1 (en) | 2014-04-09 | 2015-10-15 | Petroliam Nasional Berhad (Petronas) | Selective conversion of saccharide containing feedstock to ethylene glycol |
| TWI508937B (zh) | 2014-04-30 | 2015-11-21 | Chien An Chen | 使用甲醇為原料經由甲醛、乙醇醛的中間產物而合成乙二醇的製造方法 |
| DK3145902T3 (en) * | 2014-05-19 | 2018-10-01 | Iowa Corn Promotion Board | PROCEDURE FOR CONTINUOUS PREPARATION OF ETHYLENGYLYCOL FROM CARBOHYDRATES |
| CN106470965B (zh) | 2014-06-30 | 2019-07-26 | 托普索公司 | 从糖制备乙二醇的方法 |
| US9644150B2 (en) | 2014-12-18 | 2017-05-09 | Inaeris Technologies, Llc | Method of thermolyzing biomass in presence of hydrogen sulfide |
-
2017
- 2017-01-05 PL PL17700115T patent/PL3400208T3/pl unknown
- 2017-01-05 CA CA3010748A patent/CA3010748C/en active Active
- 2017-01-05 CN CN201780005913.4A patent/CN108473401B/zh active Active
- 2017-01-05 MX MX2018007750A patent/MX2018007750A/es unknown
- 2017-01-05 AU AU2017205265A patent/AU2017205265B2/en active Active
- 2017-01-05 WO PCT/EP2017/050183 patent/WO2017118686A1/en not_active Ceased
- 2017-01-05 US US16/068,581 patent/US10759726B2/en active Active
- 2017-01-05 RU RU2018128473A patent/RU2737159C2/ru active
- 2017-01-05 KR KR1020187022285A patent/KR102737311B1/ko active Active
- 2017-01-05 EP EP17700115.3A patent/EP3400208B1/en active Active
- 2017-01-05 UA UAA201808545A patent/UA123827C2/uk unknown
- 2017-01-05 BR BR112018013543-7A patent/BR112018013543B1/pt active IP Right Grant
- 2017-01-05 JP JP2018535315A patent/JP6975152B2/ja active Active
- 2017-01-05 DK DK17700115.3T patent/DK3400208T3/da active
- 2017-01-06 TW TW106100431A patent/TWI739786B/zh active
-
2018
- 2018-05-31 ZA ZA2018/03648A patent/ZA201803648B/en unknown
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