CH653984A5 - Preparation de carbonates d'alcenes. - Google Patents
Preparation de carbonates d'alcenes. Download PDFInfo
- Publication number
- CH653984A5 CH653984A5 CH7020/82A CH702082A CH653984A5 CH 653984 A5 CH653984 A5 CH 653984A5 CH 7020/82 A CH7020/82 A CH 7020/82A CH 702082 A CH702082 A CH 702082A CH 653984 A5 CH653984 A5 CH 653984A5
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- alkene
- catalyst
- reaction
- carbon dioxide
- Prior art date
Links
- 150000001336 alkenes Chemical class 0.000 title claims description 35
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 239000003054 catalyst Substances 0.000 claims description 44
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 38
- -1 alkene carbonate Chemical class 0.000 claims description 32
- 239000001569 carbon dioxide Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 26
- 150000004820 halides Chemical group 0.000 claims description 14
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 11
- 150000001412 amines Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical group [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 claims description 7
- 150000003003 phosphines Chemical group 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 150000001462 antimony Chemical class 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
- 150000002334 glycols Chemical class 0.000 description 22
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 13
- 238000005755 formation reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 238000006703 hydration reaction Methods 0.000 description 9
- 230000036571 hydration Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- PTBXOARBTPRBHN-UHFFFAOYSA-N 4-oxo-7h-thieno[2,3-b]pyridine-5-carboxylic acid Chemical compound O=C1C(C(=O)O)=CNC2=C1C=CS2 PTBXOARBTPRBHN-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 150000001649 bromium compounds Chemical class 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 150000004694 iodide salts Chemical class 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- WMEDSSFYIKNTNG-UHFFFAOYSA-N 3,6-dimethyloctane-3,6-diol Chemical compound CCC(C)(O)CCC(C)(O)CC WMEDSSFYIKNTNG-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GEOAXVAOYRFVAS-UHFFFAOYSA-N 4-methyl-1,3-dioxolan-2-one;2-methyloxirane Chemical compound CC1CO1.CC1COC(=O)O1 GEOAXVAOYRFVAS-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical compound O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical compound [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- GOTIICCWNAPLMN-UHFFFAOYSA-M trimethylsulfanium;bromide Chemical compound [Br-].C[S+](C)C GOTIICCWNAPLMN-UHFFFAOYSA-M 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32644781A | 1981-12-02 | 1981-12-02 | |
| US06/441,191 US4786741A (en) | 1982-11-15 | 1982-11-15 | Preparation of alkylene carbonates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH653984A5 true CH653984A5 (fr) | 1986-01-31 |
Family
ID=26985411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7020/82A CH653984A5 (fr) | 1981-12-02 | 1982-12-02 | Preparation de carbonates d'alcenes. |
Country Status (18)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5138073A (en) * | 1981-12-02 | 1992-08-11 | Scientific Design Company, Inc. | Preparation of alkylene carbonates |
| US4400559A (en) * | 1982-06-14 | 1983-08-23 | The Halcon Sd Group, Inc. | Process for preparing ethylene glycol |
| US4931571A (en) * | 1984-10-25 | 1990-06-05 | Scientific Design Company, Inc. | Process for preparing alkylene carbonates from alkylene oxides |
| US4851555A (en) * | 1984-10-25 | 1989-07-25 | Scientific Design Company, Inc. | Process for preparing alkylene oxides from alkylene carbonates |
| DE4030283A1 (de) * | 1990-09-25 | 1992-03-26 | Ruetgerswerke Ag | Verfahren zur herstellung cyclischer carbonate |
| DE4105554A1 (de) | 1991-02-22 | 1992-08-27 | Bayer Ag | Verfahren zur herstellung von dialkylcarbonaten |
| JP3823149B2 (ja) | 2002-03-06 | 2006-09-20 | 独立行政法人産業技術総合研究所 | アルキレンカーボネート合成触媒 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE740366C (de) * | 1939-03-11 | 1943-10-19 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Glykolcarbonat |
| US2773070A (en) * | 1952-10-31 | 1956-12-04 | Jefferson Chem Co Inc | Catalytic process for producing alkylene carbonates |
| US2994705A (en) * | 1958-12-08 | 1961-08-01 | Pure Oil Co | Preparation of cyclic alkylene carbonates in the presence of organic phosphonium compounds |
-
1982
- 1982-11-24 IN IN869/DEL/82A patent/IN159117B/en unknown
- 1982-11-24 AU AU90842/82A patent/AU558415B2/en not_active Ceased
- 1982-12-01 NO NO824030A patent/NO162519C/no unknown
- 1982-12-01 DE DE19823244456 patent/DE3244456A1/de active Granted
- 1982-12-01 NL NL8204661A patent/NL8204661A/nl not_active Application Discontinuation
- 1982-12-01 SU SU823522506A patent/SU1574175A3/ru active
- 1982-12-01 FR FR8220165A patent/FR2517306B1/fr not_active Expired
- 1982-12-01 BR BR8206977A patent/BR8206977A/pt not_active IP Right Cessation
- 1982-12-01 KR KR8205390A patent/KR860001856B1/ko not_active Expired
- 1982-12-01 SE SE8206848A patent/SE454088B/sv not_active IP Right Cessation
- 1982-12-02 BG BG058786A patent/BG48693A3/xx unknown
- 1982-12-02 CH CH7020/82A patent/CH653984A5/fr not_active IP Right Cessation
- 1982-12-02 ES ES517885A patent/ES8401435A1/es not_active Expired
- 1982-12-02 GB GB08234366A patent/GB2113207B/en not_active Expired
- 1982-12-02 IT IT49611/82A patent/IT1189430B/it active
- 1982-12-02 MX MX195419A patent/MX163138B/es unknown
- 1982-12-02 RO RO82109206A patent/RO85557A/ro unknown
- 1982-12-02 AR AR291484A patent/AR231432A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| DE3244456C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-07-05 |
| NO824030L (no) | 1983-06-03 |
| SE8206848L (sv) | 1983-06-03 |
| GB2113207A (en) | 1983-08-03 |
| KR860001856B1 (ko) | 1986-10-24 |
| SE454088B (sv) | 1988-03-28 |
| MX163138B (es) | 1991-08-30 |
| AU9084282A (en) | 1983-06-09 |
| NO162519B (no) | 1989-10-02 |
| GB2113207B (en) | 1986-05-08 |
| NL8204661A (nl) | 1983-07-01 |
| IT1189430B (it) | 1988-02-04 |
| IT8249611A0 (it) | 1982-12-02 |
| FR2517306B1 (fr) | 1986-02-28 |
| FR2517306A1 (fr) | 1983-06-03 |
| AR231432A1 (es) | 1984-11-30 |
| BG48693A3 (en) | 1991-04-15 |
| SE8206848D0 (sv) | 1982-12-01 |
| BR8206977A (pt) | 1983-10-11 |
| NO162519C (no) | 1990-01-10 |
| DE3244456A1 (de) | 1983-06-23 |
| KR840002762A (ko) | 1984-07-16 |
| RO85557A (ro) | 1985-03-15 |
| IN159117B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-03-28 |
| SU1574175A3 (ru) | 1990-06-23 |
| AU558415B2 (en) | 1987-01-29 |
| ES517885A0 (es) | 1983-12-16 |
| ES8401435A1 (es) | 1983-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: SCIENTIFIC DESIGN COMPANY, INC. |
|
| PL | Patent ceased | ||
| PL | Patent ceased |