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 butanol

Info

Publication number: NO852365L
Authority: NO; Norway
Prior art keywords: dialkyl; oxalate; alcohol; tertiary butanol; carbonate
Prior art date: 1984-06-14

Application number

NO852365A

Other languages

English (en)

Norwegian (no)

Inventor

Gillian Wainhouse

George Ernest Morris

Original Assignee

British Petroleum Co Plc

Priority date (The priority date 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 date listed.)

1984-06-14

Filing date

1985-06-11

Publication date

1985-12-16

1985-06-11 Application filed by British Petroleum Co Plc filed Critical British Petroleum Co Plc

1985-12-16 Publication of NO852365L publication Critical patent/NO852365L/no

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)
Treating Waste Gases (AREA)
Polyesters Or Polycarbonates (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO852365A 1984-06-14 1985-06-11 Fremgangsmaate for koproduksjon av enten et dialkylkarbonat eller et dialkyloksalat og tertiaer butanol NO852365L (no)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 NO NO852365A patent/NO852365L/no unknown
- 1985-06-11 AU AU43474/85A patent/AU4347485A/en not_active Abandoned
- 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
US4644078A (en)	1987-02-17
AU4347485A (en)	1985-12-19
EP0165746A2 (de)	1985-12-27
GB8415150D0 (en)	1984-07-18
ZA854378B (en)	1987-02-25
JPS6130540A (ja)	1986-02-12
NZ212353A (en)	1988-11-29
US4689430A (en)	1987-08-25
EP0165746A3 (de)	1987-01-21
CA1244464A (en)	1988-11-08

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