NO852365L - Fremgangsmaate for koproduksjon av enten et dialkylkarbonat eller et dialkyloksalat og tertiaer butanol - Google Patents
Fremgangsmaate for koproduksjon av enten et dialkylkarbonat eller et dialkyloksalat og tertiaer butanolInfo
- Publication number
- NO852365L NO852365L NO852365A NO852365A NO852365L NO 852365 L NO852365 L NO 852365L NO 852365 A NO852365 A NO 852365A NO 852365 A NO852365 A NO 852365A NO 852365 L NO852365 L NO 852365L
- Authority
- NO
- Norway
- Prior art keywords
- dialkyl
- oxalate
- alcohol
- tertiary butanol
- carbonate
- Prior art date
Links
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 28
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 title claims description 26
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title claims description 22
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- 239000001282 iso-butane Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 18
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 17
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 17
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 15
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 239000001273 butane Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
- 230000018044 dehydration Effects 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 10
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 claims description 9
- 238000005810 carbonylation reaction Methods 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 238000006317 isomerization reaction Methods 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 230000006315 carbonylation Effects 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- -1 copper-activated palladium Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims 1
- LOMVENUNSWAXEN-NUQCWPJISA-N dimethyl oxalate Chemical group CO[14C](=O)[14C](=O)OC LOMVENUNSWAXEN-NUQCWPJISA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- 150000003901 oxalic acid esters Chemical class 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 5
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000000075 primary alcohol group Chemical group 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000006079 antiknock agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
-
- 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
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
-
- 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
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Treating Waste Gases (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848415150A GB8415150D0 (en) | 1984-06-14 | 1984-06-14 | Coproduction of dialkyl carbonate/dialkyl and tertiary butanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852365L true NO852365L (no) | 1985-12-16 |
Family
ID=10562411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852365A NO852365L (no) | 1984-06-14 | 1985-06-11 | Fremgangsmaate for koproduksjon av enten et dialkylkarbonat eller et dialkyloksalat og tertiaer butanol |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US4644078A (de) |
| EP (1) | EP0165746A3 (de) |
| JP (1) | JPS6130540A (de) |
| AU (1) | AU4347485A (de) |
| CA (1) | CA1244464A (de) |
| GB (1) | GB8415150D0 (de) |
| NO (1) | NO852365L (de) |
| NZ (1) | NZ212353A (de) |
| ZA (1) | ZA854378B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4740215A (en) * | 1987-01-27 | 1988-04-26 | Union Oil Company Of California | Composition for cetane improvement of diesel fuels |
| US5183920A (en) * | 1992-01-13 | 1993-02-02 | The Dow Chemical Company | Integrated process for the production of dimethyl carbonate |
| US5312998A (en) * | 1993-06-10 | 1994-05-17 | Arco Chemical Technology, L.P. | Integrated process for the production of ditertiary butyl peroxide |
| US6008399A (en) * | 1999-03-11 | 1999-12-28 | Mobil Oil Corporation | Process for preparing organic carbonates |
| CN102442903A (zh) * | 2010-10-15 | 2012-05-09 | 安徽淮化股份有限公司 | 工业生产乙二醇的废气中草酸二甲酯、碳酸二甲酯的回收方法 |
| CN102391167B (zh) * | 2011-08-26 | 2013-11-27 | 湘潭大学 | 一种异丁烷氧化制备叔丁基过氧化氢和叔丁醇的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL65254C (de) * | 1943-10-04 | |||
| FR929276A (fr) * | 1946-06-18 | 1947-12-22 | Bataafsche Petroleum | Procédé pour l'isomérisation du butane normal en isobutane |
| US2862973A (en) * | 1956-04-27 | 1958-12-02 | Shell Dev | Di-tertiary-alkyl peroxide production |
| US3987115A (en) * | 1971-03-16 | 1976-10-19 | Atlantic Richfield Company | Production of hydroperoxides |
| US4160107A (en) * | 1976-04-12 | 1979-07-03 | Montedison S.P.A. | Process for the preparation of esters of oxalic acid |
| US4138580A (en) * | 1976-10-06 | 1979-02-06 | Ube Industries, Ltd. | Process for preparing diesters of dicarboxylic acids |
| US4404406A (en) * | 1981-10-05 | 1983-09-13 | Shell Oil Company | Oxidation of isobutane under super-critical conditions |
| CA1213607A (en) * | 1982-12-15 | 1986-11-04 | George E. Morris | Process for the production of dihydrocarbyl oxalates |
| CA1218670A (en) * | 1982-12-15 | 1987-03-03 | The British Petroleum Company P.L.C. | Process for the production of dihydrocarbyl carbonates, their use as fuels additives and fuel compositions containing them |
-
1984
- 1984-06-14 GB GB848415150A patent/GB8415150D0/en active Pending
-
1985
- 1985-06-04 US US06/741,250 patent/US4644078A/en not_active Expired - Fee Related
- 1985-06-06 EP EP85304042A patent/EP0165746A3/de not_active Withdrawn
- 1985-06-07 NZ NZ212353A patent/NZ212353A/xx unknown
- 1985-06-10 ZA ZA854378A patent/ZA854378B/xx unknown
- 1985-06-11 AU AU43474/85A patent/AU4347485A/en not_active Abandoned
- 1985-06-11 NO NO852365A patent/NO852365L/no unknown
- 1985-06-11 CA CA000483622A patent/CA1244464A/en not_active Expired
- 1985-06-13 JP JP12907685A patent/JPS6130540A/ja active Pending
-
1986
- 1986-11-17 US US06/931,606 patent/US4689430A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB8415150D0 (en) | 1984-07-18 |
| EP0165746A2 (de) | 1985-12-27 |
| CA1244464A (en) | 1988-11-08 |
| ZA854378B (en) | 1987-02-25 |
| EP0165746A3 (de) | 1987-01-21 |
| AU4347485A (en) | 1985-12-19 |
| NZ212353A (en) | 1988-11-29 |
| JPS6130540A (ja) | 1986-02-12 |
| US4689430A (en) | 1987-08-25 |
| US4644078A (en) | 1987-02-17 |
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