RU2464267C2 - Способ получения 1,2-алкиленкарбоната - Google Patents
Способ получения 1,2-алкиленкарбоната Download PDFInfo
- Publication number
- RU2464267C2 RU2464267C2 RU2009143002/04A RU2009143002A RU2464267C2 RU 2464267 C2 RU2464267 C2 RU 2464267C2 RU 2009143002/04 A RU2009143002/04 A RU 2009143002/04A RU 2009143002 A RU2009143002 A RU 2009143002A RU 2464267 C2 RU2464267 C2 RU 2464267C2
- Authority
- RU
- Russia
- Prior art keywords
- distillation
- stream
- catalyst
- alkylene
- reactor
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 59
- 238000004821 distillation Methods 0.000 claims abstract description 144
- 239000003054 catalyst Substances 0.000 claims abstract description 115
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 106
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 53
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 53
- 238000003763 carbonization Methods 0.000 claims abstract description 26
- 238000004064 recycling Methods 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- -1 obtaining 1 Chemical compound 0.000 claims description 27
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 13
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000005809 transesterification reaction Methods 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical group CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 18
- 239000012467 final product Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000356 contaminant Substances 0.000 description 9
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- 230000002441 reversible effect Effects 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical group [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- WEGOLYBUWCMMMY-UHFFFAOYSA-N 1-bromo-2-propanol Chemical compound CC(O)CBr WEGOLYBUWCMMMY-UHFFFAOYSA-N 0.000 description 1
- DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical class [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 229910052915 alkaline earth metal silicate Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- OJTDGPLHRSZIAV-UHFFFAOYSA-N propane-1,2-diol Chemical compound CC(O)CO.CC(O)CO OJTDGPLHRSZIAV-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003476 thallium compounds Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052726 zirconium Chemical class 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
- B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
-
- 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
- Y02P20/584—Recycling of catalysts
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)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07106712 | 2007-04-23 | ||
| EP07106712.8 | 2007-04-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009143002A RU2009143002A (ru) | 2011-05-27 |
| RU2464267C2 true RU2464267C2 (ru) | 2012-10-20 |
Family
ID=38514135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009143002/04A RU2464267C2 (ru) | 2007-04-23 | 2008-04-17 | Способ получения 1,2-алкиленкарбоната |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20100130751A1 (enExample) |
| EP (1) | EP2137176B1 (enExample) |
| JP (1) | JP5378355B2 (enExample) |
| KR (1) | KR101548024B1 (enExample) |
| CN (1) | CN101663288B (enExample) |
| AT (1) | ATE496902T1 (enExample) |
| DE (1) | DE602008004753D1 (enExample) |
| ES (1) | ES2356278T3 (enExample) |
| RU (1) | RU2464267C2 (enExample) |
| TW (1) | TWI415843B (enExample) |
| WO (1) | WO2008128956A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101832447B1 (ko) | 2014-10-23 | 2018-02-26 | 주식회사 엘지화학 | 폴리알킬렌카보네이트를 포함하는 수지 조성물의 연속 제조방법 |
| US10829635B2 (en) | 2016-03-11 | 2020-11-10 | Lg Chem, Ltd. | Economical method of preparing a resin composition including polyalkylene carbonate with improved thermal stability and processability |
| KR101966135B1 (ko) | 2017-12-07 | 2019-04-05 | 한국에너지기술연구원 | 이산화탄소 포집공정과 연계된 알킬렌카보네이트의 정제를 위한 진공증류 시스템 |
| WO2022189318A1 (de) * | 2021-03-12 | 2022-09-15 | Covestro Deutschland Ag | Verfahren zur aufreinigung von cyclischen carbonaten |
| US11897860B2 (en) | 2022-03-14 | 2024-02-13 | Baker Hughes Oilfield Operations Llc | Direct synthesis of cyclic carbonates using choline chloride as catalyst under mild conditions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU170529A1 (ru) * | С. Левин , А. Л. Шапиро | Способ получения алкиленкарбонатов |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE2748718A1 (de) * | 1977-10-29 | 1979-05-03 | Bayer Ag | Verfahren zur herstellung von dialkylcarbonaten |
| US4314945A (en) * | 1977-12-22 | 1982-02-09 | Union Carbide Corporation | Alkylene carbonate process |
| US4221727A (en) * | 1979-08-17 | 1980-09-09 | The Dow Chemical Company | Ethylene oxide recovery |
| JPH01211579A (ja) * | 1979-08-17 | 1989-08-24 | Dow Chem Co:The | エチレンカーボネートの製造方法 |
| DE4030283A1 (de) * | 1990-09-25 | 1992-03-26 | Ruetgerswerke Ag | Verfahren zur herstellung cyclischer carbonate |
| DE4129316A1 (de) * | 1991-09-03 | 1993-03-04 | Bayer Ag | Verfahren zur kontinuierlichen herstellung von dialkylcarbonaten |
| DE4216121A1 (de) * | 1992-05-15 | 1993-11-18 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von Dialkylcarbonaten |
| DE4318892A1 (de) * | 1993-06-07 | 1994-12-08 | Bayer Ag | Verfahren zur Herstellung von Propylenglykolcarbonat |
| US5691041A (en) * | 1995-09-29 | 1997-11-25 | International Business Machines Corporation | Socket for semi-permanently connecting a solder ball grid array device using a dendrite interposer |
| ES2196643T3 (es) | 1998-10-07 | 2003-12-16 | Huntsman Spec Chem Corp | Procedimiento de preparacion de carbonato de alquileno. |
| US6384240B1 (en) * | 1998-10-07 | 2002-05-07 | Huntsman Petrochemical Corporation | Process for the purification of alkylene carbonate |
| US6458969B1 (en) * | 1998-10-07 | 2002-10-01 | Huntsman Petrochemical Corporation | Process for the purification of alkylene carbonate |
| JP4370777B2 (ja) * | 2002-12-19 | 2009-11-25 | 三菱化学株式会社 | アルキレンカーボネートの製造方法 |
| ES2293327T3 (es) * | 2003-06-30 | 2008-03-16 | Shell Internationale Research Maatschappij B.V. | Procedimiento para la preparacion de carbonato de propileno. |
-
2008
- 2008-04-17 JP JP2010504639A patent/JP5378355B2/ja active Active
- 2008-04-17 WO PCT/EP2008/054659 patent/WO2008128956A1/en not_active Ceased
- 2008-04-17 KR KR1020097024188A patent/KR101548024B1/ko active Active
- 2008-04-17 ES ES08736323T patent/ES2356278T3/es active Active
- 2008-04-17 RU RU2009143002/04A patent/RU2464267C2/ru active
- 2008-04-17 US US12/597,084 patent/US20100130751A1/en not_active Abandoned
- 2008-04-17 EP EP08736323A patent/EP2137176B1/en active Active
- 2008-04-17 CN CN2008800131617A patent/CN101663288B/zh active Active
- 2008-04-17 DE DE602008004753T patent/DE602008004753D1/de active Active
- 2008-04-17 AT AT08736323T patent/ATE496902T1/de not_active IP Right Cessation
- 2008-04-21 TW TW097114536A patent/TWI415843B/zh active
-
2015
- 2015-11-30 US US14/953,836 patent/US20160108017A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU170529A1 (ru) * | С. Левин , А. Л. Шапиро | Способ получения алкиленкарбонатов |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101548024B1 (ko) | 2015-08-27 |
| ES2356278T3 (es) | 2011-04-06 |
| JP2010525010A (ja) | 2010-07-22 |
| JP5378355B2 (ja) | 2013-12-25 |
| EP2137176B1 (en) | 2011-01-26 |
| DE602008004753D1 (de) | 2011-03-10 |
| CN101663288A (zh) | 2010-03-03 |
| TWI415843B (zh) | 2013-11-21 |
| ATE496902T1 (de) | 2011-02-15 |
| RU2009143002A (ru) | 2011-05-27 |
| EP2137176A1 (en) | 2009-12-30 |
| CN101663288B (zh) | 2013-08-21 |
| KR20100017175A (ko) | 2010-02-16 |
| US20100130751A1 (en) | 2010-05-27 |
| US20160108017A1 (en) | 2016-04-21 |
| TW200916455A (en) | 2009-04-16 |
| WO2008128956A1 (en) | 2008-10-30 |
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