JPS6139294B2 - - Google Patents
Info
- Publication number
- JPS6139294B2 JPS6139294B2 JP59176321A JP17632184A JPS6139294B2 JP S6139294 B2 JPS6139294 B2 JP S6139294B2 JP 59176321 A JP59176321 A JP 59176321A JP 17632184 A JP17632184 A JP 17632184A JP S6139294 B2 JPS6139294 B2 JP S6139294B2
- Authority
- JP
- Japan
- Prior art keywords
- formaldehyde
- ethylene glycol
- present
- mixed gas
- phenol
- 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.)
- Expired
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 72
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 65
- 239000007789 gas Substances 0.000 claims description 13
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- -1 glycolic acid ester Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59176321A JPS6153235A (ja) | 1984-08-24 | 1984-08-24 | エチレングリコ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59176321A JPS6153235A (ja) | 1984-08-24 | 1984-08-24 | エチレングリコ−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6153235A JPS6153235A (ja) | 1986-03-17 |
| JPS6139294B2 true JPS6139294B2 (US20110009641A1-20110113-C00185.png) | 1986-09-03 |
Family
ID=16011536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59176321A Granted JPS6153235A (ja) | 1984-08-24 | 1984-08-24 | エチレングリコ−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6153235A (US20110009641A1-20110113-C00185.png) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61192173U (US20110009641A1-20110113-C00185.png) * | 1985-05-17 | 1986-11-29 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5731472A (en) * | 1995-12-06 | 1998-03-24 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| EP2915584A1 (en) * | 2014-03-05 | 2015-09-09 | Basf Se | Ruthenium-phenol catalysts for transfer hydrogenation reactions |
-
1984
- 1984-08-24 JP JP59176321A patent/JPS6153235A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61192173U (US20110009641A1-20110113-C00185.png) * | 1985-05-17 | 1986-11-29 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6153235A (ja) | 1986-03-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0625031A (ja) | 酸素化されたアセチル化合物の合成方法 | |
| US4556744A (en) | Process for the production of ethanol and/or acetaldehyde by the metal catalysed liquid phase reaction of methanol, carbon monoxide and hydrogen in the presence of a solvent | |
| EP0078616A2 (en) | Process for preparing ethylene glycol | |
| JPS6139294B2 (US20110009641A1-20110113-C00185.png) | ||
| CA1184203A (en) | Preparation of ethylene glycol | |
| EP0146291B1 (en) | Process for the production of carboxylic acids and/or esters thereof | |
| CA1192226A (en) | Process for preparing ethylene glycol and lower monohydric alcohols from syngas using a novel catalyst system | |
| EP0151822B1 (en) | Process for the preparation of 1,4-butanediol | |
| AU558487B2 (en) | Process for the production of dihydrocarbyl oxalates | |
| US4423257A (en) | Process for producing ethanol | |
| US4433178A (en) | Process for preparing acetaldehyde from methanol and synthesis gas using a novel catalyst composition | |
| EP0075952A1 (en) | Hydrogenolysis process for the production of monoethylene glycol monomethyl ether, monoethylene glycol and ethanol | |
| EP0036724A1 (en) | Process for the production of ethanol by the liquid phase hydrocarbonylation of methanol | |
| JPS624373B2 (US20110009641A1-20110113-C00185.png) | ||
| CA1192227A (en) | Process for preparing ethylene glycol and lower monohydric alcohols from syngas using a novel catalyst system | |
| US4433177A (en) | Process for preparing acetaldehyde from methanol and synthesis gas using a novel catalyst composition | |
| US4283582A (en) | Pre-pressuring methanol-cobalt with carbon monoxide in homologation of methanol | |
| US4661643A (en) | Hydrogenolysis process for the production of monoethylene glycol monomethyl ether, monoethylene glycol and ethanol | |
| JP3756537B2 (ja) | ジメチルデカンジアールおよびその製造方法 | |
| US4351907A (en) | Preparation of ethylene glycol | |
| JPS6048940A (ja) | メタノ−ル及び合成ガスからのエタノ−ルの製造方法 | |
| JPS599529B2 (ja) | エタノ−ルの製造方法 | |
| JPS6139292B2 (US20110009641A1-20110113-C00185.png) | ||
| EP0076461A1 (en) | Hydrogenolysis of polyalkylene glycols to produce monoethylene glycol monoalkyl ethers, monoethylene glycol and ethanol | |
| JPS606929B2 (ja) | エチレングリコ−ルの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |