JP6522155B2 - 炭水化物源からエチレングルコールを製造する方法 - Google Patents
炭水化物源からエチレングルコールを製造する方法 Download PDFInfo
- Publication number
- JP6522155B2 JP6522155B2 JP2017555201A JP2017555201A JP6522155B2 JP 6522155 B2 JP6522155 B2 JP 6522155B2 JP 2017555201 A JP2017555201 A JP 2017555201A JP 2017555201 A JP2017555201 A JP 2017555201A JP 6522155 B2 JP6522155 B2 JP 6522155B2
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- Prior art keywords
- ethylene glycol
- tungsten
- catalyst system
- carbohydrate source
- diluent
- 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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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 217
- 150000001720 carbohydrates Chemical class 0.000 title claims description 100
- 238000000034 method Methods 0.000 title claims description 60
- 235000014633 carbohydrates Nutrition 0.000 claims description 98
- -1 alkylene glycol Chemical compound 0.000 claims description 69
- 238000006243 chemical reaction Methods 0.000 claims description 67
- 239000003085 diluting agent Substances 0.000 claims description 61
- 239000003054 catalyst Substances 0.000 claims description 55
- 229910052751 metal Inorganic materials 0.000 claims description 49
- 239000002184 metal Substances 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 26
- 150000003658 tungsten compounds Chemical class 0.000 claims description 26
- 229910052721 tungsten Inorganic materials 0.000 claims description 25
- 239000010937 tungsten Substances 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 229910052707 ruthenium Inorganic materials 0.000 claims description 19
- 150000002972 pentoses Chemical class 0.000 claims description 18
- 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 15
- 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 15
- 239000008103 glucose Substances 0.000 claims description 15
- 150000002402 hexoses Chemical class 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 239000001913 cellulose Substances 0.000 claims description 13
- 229920002678 cellulose Polymers 0.000 claims description 13
- 238000004517 catalytic hydrocracking Methods 0.000 claims description 11
- 229910052697 platinum Inorganic materials 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052741 iridium Inorganic materials 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims description 8
- 229920002472 Starch Polymers 0.000 claims description 7
- 230000000737 periodic effect Effects 0.000 claims description 7
- 239000008107 starch Substances 0.000 claims description 7
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- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 235000000346 sugar Nutrition 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 229920002488 Hemicellulose Polymers 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 150000008163 sugars Chemical class 0.000 claims description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 3
- 229910001887 tin oxide Inorganic materials 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- XAYGUHUYDMLJJV-UHFFFAOYSA-Z decaazanium;dioxido(dioxo)tungsten;hydron;trioxotungsten Chemical compound [H+].[H+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O XAYGUHUYDMLJJV-UHFFFAOYSA-Z 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 38
- 239000000047 product Substances 0.000 description 19
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
- 235000010980 cellulose Nutrition 0.000 description 12
- 150000002739 metals Chemical group 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 238000007327 hydrogenolysis reaction Methods 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000003377 acid catalyst Substances 0.000 description 7
- 239000010948 rhodium Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 150000004862 dioxolanes Chemical class 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000011973 solid acid Substances 0.000 description 4
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- 239000004386 Erythritol Substances 0.000 description 3
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- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
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- FYGDTMLNYKFZSV-ZWSAEMDYSA-N cellotriose 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]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-ZWSAEMDYSA-N 0.000 description 1
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- 239000004615 ingredient Substances 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
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- 238000002386 leaching Methods 0.000 description 1
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- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
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- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
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- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/30—Tungsten
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/19—Catalysts containing parts with different compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
したがって、本発明は、炭水化物源からエチレングルコールを製造する方法であって、
水素、炭水化物源、液体希釈剤、及び触媒システムが、反応剤として、反応ゾーンに導入され;
前記触媒システムは、タングステン化合物と、元素周期律表の第8、9、及び10族から選択される少なくとも1つの水素化分解金属とを含み;
反応ゾーンに導入される前記液体希釈剤は、アルキレングリコールを含み;
前記炭水化物源が、前記触媒システムの存在下で水素と反応して、エチレングリコールを含む生成物が得られる方法を提供する。
レングリコール及び希釈剤を含む生成物混合物がCSTRから取り出される。
Claims (19)
- 炭水化物源からエチレングリコールを製造するための方法であって、
水素、炭水化物源、液体希釈剤、及び触媒システムが、反応剤として、反応ゾーンに導入され;
前記触媒システムは、タングステン化合物と、元素周期律表の第8、9、又は10族から選択される少なくとも1つの水素化分解金属とを含み;
反応ゾーンに導入される前記液体希釈剤は、アルキレングリコールを含み;
前記炭水化物源が、前記触媒システムの存在下で水素と反応して、エチレングリコールを含む生成物が得られる方法。 - 前記液体希釈剤が、エチレングリコールを含む、請求項1に記載の方法。
- 前記炭水化物源が、セルロース、デンプン、ヘミセルロース糖、グルコース、及びそれらの混合物からなる群から選択される、請求項1又は2に記載の方法。
- 前記触媒システムが、少なくとも+2の酸化状態を有するタングステン化合物を含む、請求項1〜3のいずれか一項に記載の方法。
- 前記触媒システムが、タングステン酸(H2WO4)、タングステン酸アンモニウム、メタタングステン酸アンモニウム、パラタングステン酸アンモニウム、少なくとも1種の第1又は2族元素を含むタングステン酸塩化合物、少なくとも1種の第1又は2族元素を含むメタタングステン酸塩化合物、少なくとも1種の第1又は2族元素を含むパラタングステン酸塩化合物、酸化タングステン(WO3)、タングステンのヘテロポリ化合物、及びそれらの組み合わせからなる群から選択されるタングステン化合物を含む、請求項1〜4のいずれか一項に記載の方法。
- 前記触媒システムがタングステン酸を含む、請求項5に記載の方法。
- 元素周期律表の第8、9、又は10族から選択される前記水素化分解金属が、Cu、Fe、Ni、Co、Pd、Pt、Ru、Rh、Ir、Os、及びそれらの組み合わせからなる群から選択される、請求項1〜6のいずれか一項に記載の方法。
- 元素周期律表の第8、9、又は10族から選択される前記少なくとも1つの水素化分解金属が、担体上に担持された触媒の形態で存在し、前記担体が、活性炭、シリカ、アルミナ、シリカ−アルミナ、ジルコニア、チタニア、ニオビア、酸化鉄、酸化スズ、酸化亜鉛、シリカ−ジルコニア、ゼオライトアルミノシリケート、チタノシリケート、マグネシア、炭化ケイ素、クレイ、及びそれらの組み合わせからなる支持体から選択される、請求項1〜7のいずれか一項に記載の方法。
- 前記触媒システムが、活性炭上のルテニウムを含む、請求項7又は8に記載の方法。
- タングステンの前記少なくとも1つの水素化分解金属に対するモル比が1〜25の範囲である、請求項1〜9のいずれか一項に記載の方法。
- 前記タングステン化合物の濃度が、タングステンとして計算して、かつ炭水化物源の質量に基づいて、1〜35質量%の範囲である、請求項1〜10のいずれか一項に記載の方法。
- 前記炭水化物源が、少なくも1種のペントース含有炭水化物と、少なくとも1種のヘキソース含有炭水化物との組み合わせを含む、請求項1〜11のいずれか一項に記載の方法。
- 前記液体希釈剤が、アルキレングリコールと水との混合物であり、アルキレングリコールの量が、水及びアルキレングリコールの体積を基準にして、2〜25体積%の範囲である、請求項1〜12のいずれか一項に記載の方法。
- 前記液体希釈剤が、スルホキシド類、アルキレングリコール以外のアルコール類、アミド類、及びそれらの混合物からなる群から選択される1つ以上の化合物をさらに含む、請求項13に記載の方法。
- 前記エチレングリコールを含む生成物が、1つ以上の連行剤を用いて精製される、請求項1〜14のいずれか一項に記載の方法。
- 反応ゾーン内の温度が120〜300℃の範囲である、請求項1〜15のいずれか一項に記載の方法。
- 反応ゾーン内の水素分圧が1〜6MPaの範囲である、請求項1〜16のいずれか一項に記載の方法。
- 反応ゾーン内での触媒システムの平均滞留時間が5分〜6時間の範囲である、請求項1〜17のいずれか一項に記載の方法。
- 既にアルキルレングリコールを含む希釈剤を、触媒システムの存在下で炭水化物源を水素と反応させてエチレングリコールを含む生成物を得ることを反応ゾーンで開始する前に、前記反応ゾーンに導入する、請求項1〜18のいずれか一項に記載の方法。
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PCT/NL2016/050026 WO2016114658A1 (en) | 2015-01-13 | 2016-01-13 | Process for preparing ethylene glycol from a carbohydrate |
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EP (1) | EP3245182B1 (ja) |
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CA (1) | CA2973436C (ja) |
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AU2016207242B2 (en) * | 2015-01-13 | 2018-09-13 | Avantium Knowledge Centre B.V. | Continuous process for preparing ethylene glycol from a carbohydrate source |
PL3245183T3 (pl) | 2015-01-13 | 2020-07-27 | Avantium Knowledge Centre B.V. | Sposób wytwarzania glikolu etylenowego ze źródła węglowodanów |
PL3245182T3 (pl) | 2015-01-13 | 2020-06-29 | Avantium Knowledge Centre B.V. | Sposób wytwarzania glikolu etylenowego z węglowodanu |
EP3365316B2 (en) | 2015-10-20 | 2022-04-27 | Shell Internationale Research Maatschappij B.V. | Process for the production of glycols |
US10472310B2 (en) | 2016-06-03 | 2019-11-12 | Iowa Corn Promotion Board | Continuous processes for the highly selective conversion of sugars to propylene glycol or mixtures of propylene glycol and ethylene glycol |
CN109641191B (zh) | 2016-06-03 | 2023-04-04 | 爱荷华谷类推广协会 | 将产生己醛糖的碳水化合物高度选择性地转化为乙二醇的连续方法 |
CN106905109A (zh) * | 2017-01-18 | 2017-06-30 | 同济大学 | 一种催化氢解纤维素产丙二醇的方法 |
CN107573213A (zh) * | 2017-08-11 | 2018-01-12 | 厦门大学 | 一种生物质制乙醇和乙二醇的化学方法 |
EP3717445A4 (en) * | 2017-12-01 | 2021-07-07 | Iowa Corn Promotion Board | CONTINUOUS PROCESSES FOR THE HIGHLY SELECTIVE CONVERSION OF SUGARS TO PROPYLENE-GLYCOL OR MIXTURES OF PROPYLENE-GLYCOL AND ETHYLENE-GLYCOL |
BR112020017094B8 (pt) * | 2018-03-14 | 2024-03-05 | Avantium Knowledge Centre Bv | Processo contínuo ou semicontínuo para a preparação de etilenoglicol |
EA202092099A1 (ru) | 2018-03-14 | 2020-11-26 | Авантиум Нолидж Сентр Б.В. | Способ производства этиленгликоля |
WO2019175365A1 (en) * | 2018-03-14 | 2019-09-19 | Avantium Knowledge Centre B.V. | Process for the production of ethylene glycol and heterogeneous catalyst composition |
WO2020182456A1 (en) | 2019-03-14 | 2020-09-17 | Avantium Knowledge Centre B.V. | Process for the conversion of one or more polyols |
CA3155648A1 (en) | 2019-09-24 | 2021-04-01 | Iowa Corn Promotion Board | Continuous, carbohydrate to ethylene glycol processes |
CN110981691B (zh) * | 2019-12-16 | 2021-01-15 | 北京大学 | 一种利用单糖合成1,6-己二醇的方法 |
US11319269B2 (en) | 2020-09-24 | 2022-05-03 | Iowa Corn Promotion Board | Continuous processes for the selective conversion of aldohexose-yielding carbohydrate to ethylene glycol using low concentrations of retro-aldol catalyst |
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