TWI281913B - Production method for both end-hydroxyl group-terminated diols - Google Patents
Production method for both end-hydroxyl group-terminated diols Download PDFInfo
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- TWI281913B TWI281913B TW091101391A TW91101391A TWI281913B TW I281913 B TWI281913 B TW I281913B TW 091101391 A TW091101391 A TW 091101391A TW 91101391 A TW91101391 A TW 91101391A TW I281913 B TWI281913 B TW I281913B
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- catalyst
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- 150000002009 diols Chemical class 0.000 title claims abstract description 92
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 91
- 239000003054 catalyst Substances 0.000 claims abstract description 215
- 238000000034 method Methods 0.000 claims abstract description 74
- -1 diol compound Chemical class 0.000 claims abstract description 73
- 238000006243 chemical reaction Methods 0.000 claims description 132
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 92
- 239000001257 hydrogen Substances 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 88
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 63
- 150000005846 sugar alcohols Chemical class 0.000 claims description 62
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 61
- 229910052799 carbon Inorganic materials 0.000 claims description 46
- 239000002904 solvent Substances 0.000 claims description 35
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- 229910000420 cerium oxide Inorganic materials 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 26
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 26
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 20
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000005984 hydrogenation reaction Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
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- 229910052742 iron Inorganic materials 0.000 claims description 5
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- 229910021536 Zeolite Inorganic materials 0.000 claims description 4
- 229940043232 butyl acetate Drugs 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
- 229910052759 nickel Inorganic materials 0.000 claims description 4
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
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- WLLURKMCNUGIRG-UHFFFAOYSA-N alumane;cerium Chemical compound [AlH3].[Ce] WLLURKMCNUGIRG-UHFFFAOYSA-N 0.000 claims 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 1
- 150000000185 1,3-diols Chemical class 0.000 abstract description 2
- 238000004517 catalytic hydrocracking Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 105
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- 229910052757 nitrogen Inorganic materials 0.000 description 58
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 56
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- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 45
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 41
- 229940035437 1,3-propanediol Drugs 0.000 description 41
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 41
- 239000006228 supernatant Substances 0.000 description 36
- 150000001728 carbonyl compounds Chemical class 0.000 description 35
- 239000000243 solution Substances 0.000 description 34
- 206010036790 Productive cough Diseases 0.000 description 32
- 210000003802 sputum Anatomy 0.000 description 32
- 208000024794 sputum Diseases 0.000 description 32
- 238000003756 stirring Methods 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
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- 239000000203 mixture Substances 0.000 description 23
- 239000000126 substance Substances 0.000 description 22
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 description 21
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 13
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- UAXUUTJPGCTGPL-UHFFFAOYSA-N cyclohexyl(oxiran-2-yl)methanol Chemical compound C1CCCCC1C(O)C1CO1 UAXUUTJPGCTGPL-UHFFFAOYSA-N 0.000 description 1
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- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
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- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 150000004704 methoxides Chemical class 0.000 description 1
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- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- QHUCJYPNJYZEOQ-UHFFFAOYSA-N oxiran-2-yl(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)C1CO1 QHUCJYPNJYZEOQ-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
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- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
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Classifications
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/75—Cobalt
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- 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
- B01J25/00—Catalysts of the Raney type
-
- 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
- B01J25/00—Catalysts of the Raney type
- B01J25/02—Raney nickel
-
- 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
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001081783 | 2001-03-22 | ||
| JP2001373977A JP4296739B2 (ja) | 2001-03-22 | 2001-12-07 | 両末端ジオール類製造用触媒、該触媒の製造方法、該触媒を用いた両末端ジオール類の製造方法及び該製造方法で得られた両末端ジオール類 |
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| TWI281913B true TWI281913B (en) | 2007-06-01 |
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| TW091101391A TWI281913B (en) | 2001-03-22 | 2002-01-28 | Production method for both end-hydroxyl group-terminated diols |
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| US (2) | US20030119666A1 (enExample) |
| EP (1) | EP1370358A1 (enExample) |
| JP (1) | JP4296739B2 (enExample) |
| CN (1) | CN1231437C (enExample) |
| TW (1) | TWI281913B (enExample) |
| WO (1) | WO2002076610A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9799893B2 (en) * | 2006-10-18 | 2017-10-24 | Daimler Ag | Catalyst support for fuel cell |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8884036B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of hydroxymethylfurfural from levoglucosenone |
| CN104024197A (zh) | 2011-12-30 | 2014-09-03 | 纳幕尔杜邦公司 | 己二醇的制备方法 |
| BR112014015994A2 (pt) | 2011-12-30 | 2018-05-22 | Du Pont | processo. |
| US8962894B2 (en) | 2011-12-30 | 2015-02-24 | E I Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
| US8865940B2 (en) | 2011-12-30 | 2014-10-21 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8859826B2 (en) | 2012-04-27 | 2014-10-14 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US8846985B2 (en) * | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US9018423B2 (en) | 2012-04-27 | 2015-04-28 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| CN108786804B (zh) * | 2018-05-31 | 2021-01-26 | 王鹏飞 | 氢化催化剂、其制备方法及应用 |
| KR102079120B1 (ko) * | 2018-06-18 | 2020-02-19 | 한국과학기술연구원 | 칼슘염에 담지된 금속 촉매, 이의 제조방법 및 이를 이용한 함산소 화합물의 수첨탈산소 반응방법 |
| CN109806871A (zh) * | 2019-02-27 | 2019-05-28 | 浙江大学 | 缩水甘油加氢制备1,3-丙二醇的钴-氧化铝催化剂及其制备方法 |
| CN109821538B (zh) * | 2019-02-27 | 2020-11-06 | 浙江大学 | 缩水甘油加氢制备1,3-丙二醇的碳膜包覆钴催化剂及其制备方法 |
| CN116408086B (zh) * | 2023-03-28 | 2025-03-07 | 湖北大学 | 环氧丙醇高选择氢化制1,3-丙二醇催化剂的制备方法 |
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| US577166A (en) * | 1897-02-16 | Hay rake and loader combined | ||
| US397449A (en) * | 1889-02-05 | Bottle-stopper | ||
| US2895819A (en) * | 1957-09-03 | 1959-07-21 | Bjorksten Res Lab Inc | Method for preparing a catalytic metal foam and use thereof |
| GB970790A (en) * | 1961-04-06 | 1964-09-23 | Henkel & Cie Gmbh | Process for the preparation of primary alcohols |
| US3975449A (en) * | 1974-08-05 | 1976-08-17 | Chevron Research Company | Hydrogenation of epoxides to primary alcohols |
| GB1581379A (en) * | 1976-12-28 | 1980-12-10 | Du Pont | Preparation of diols by hydrogenation and hyrdrolysis of cyclic acetals |
| US4590313A (en) * | 1982-06-02 | 1986-05-20 | Atlantic Richfield Company | Method for producing primary alcohols by catalytic hydrogenation of terminal epoxides |
| BR9408460A (pt) | 1993-12-28 | 1997-08-05 | Rhone Poulenc Chimie | Processo de hidrogenação catalítica de nitrilas em aminas com o auxílio de um catalisador do tipo níquel de raney |
| US5744419A (en) * | 1994-12-19 | 1998-04-28 | Council Of Scientific And Industrial Research | Process for the preparation of an improved supported catalyst, containing nickel and cobalt, with or without noble metals, useful for the oxidative conversion of methane, natural gas and biogas to syngas |
| CN1093003C (zh) | 1999-04-29 | 2002-10-23 | 中国石油化工集团公司 | 一种加氢精制催化剂及其制备方法 |
| KR100416404B1 (ko) * | 1999-04-29 | 2004-01-31 | 차이나 피트로케미컬 코포레이션 | 수소화 촉매 및 이의 제조 방법 |
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- 2002-03-22 CN CNB028068386A patent/CN1231437C/zh not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| US20030119666A1 (en) | 2003-06-26 |
| EP1370358A1 (en) | 2003-12-17 |
| JP2002346390A (ja) | 2002-12-03 |
| US7230145B2 (en) | 2007-06-12 |
| CN1231437C (zh) | 2005-12-14 |
| JP4296739B2 (ja) | 2009-07-15 |
| US20040236156A1 (en) | 2004-11-25 |
| CN1498132A (zh) | 2004-05-19 |
| WO2002076610A1 (en) | 2002-10-03 |
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