KR20080105088A - 알케인디올 및 디알킬 카보네이트의 제조 방법 - Google Patents
알케인디올 및 디알킬 카보네이트의 제조 방법 Download PDFInfo
- Publication number
- KR20080105088A KR20080105088A KR1020087022816A KR20087022816A KR20080105088A KR 20080105088 A KR20080105088 A KR 20080105088A KR 1020087022816 A KR1020087022816 A KR 1020087022816A KR 20087022816 A KR20087022816 A KR 20087022816A KR 20080105088 A KR20080105088 A KR 20080105088A
- Authority
- KR
- South Korea
- Prior art keywords
- alkanol
- carbonate
- stream
- dialkyl carbonate
- rich stream
- 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.)
- Withdrawn
Links
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 111
- 238000004821 distillation Methods 0.000 claims abstract description 46
- -1 alkylene carbonate Chemical compound 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 26
- 238000009835 boiling Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 17
- 238000000746 purification Methods 0.000 claims abstract description 6
- 238000004064 recycling Methods 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract description 27
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 abstract description 16
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract description 12
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 description 16
- 238000000895 extractive distillation Methods 0.000 description 15
- 239000006227 byproduct Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 229960004063 propylene glycol Drugs 0.000 description 8
- 235000013772 propylene glycol Nutrition 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000012808 vapor phase Substances 0.000 description 6
- 230000000295 complement effect Effects 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000066 reactive distillation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-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
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 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
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
- C07C68/065—Preparation of esters of carbonic or haloformic acids from organic carbonates from alkylene carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/08—Purification; Separation; Stabilisation
-
- 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)
- 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 |
|---|---|---|---|
| US77546906P | 2006-02-22 | 2006-02-22 | |
| US60/775,469 | 2006-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080105088A true KR20080105088A (ko) | 2008-12-03 |
Family
ID=38024231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087022816A Withdrawn KR20080105088A (ko) | 2006-02-22 | 2007-02-20 | 알케인디올 및 디알킬 카보네이트의 제조 방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7563919B2 (enExample) |
| EP (1) | EP1986988B1 (enExample) |
| JP (1) | JP5322658B2 (enExample) |
| KR (1) | KR20080105088A (enExample) |
| CN (1) | CN101389591B (enExample) |
| TW (1) | TWI378087B (enExample) |
| WO (1) | WO2007096342A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI383976B (zh) * | 2006-02-22 | 2013-02-01 | Shell Int Research | 製備碳酸二烷酯及烷二醇的方法 |
| CN101605751B (zh) * | 2007-01-23 | 2013-01-02 | 国际壳牌研究有限公司 | 制备烷二醇和二甲基碳酸酯的方法 |
| RU2461541C2 (ru) * | 2007-01-23 | 2012-09-20 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения алкандиола и диалкилкарбоната |
| WO2008099370A2 (en) * | 2007-02-16 | 2008-08-21 | Sabic Innovative Plastics Ip Bv | Process for manufacturing dimethyl carbonate |
| CN101627003B (zh) * | 2007-02-16 | 2016-03-16 | 沙特基础全球技术有限公司 | 碳酸二甲酯的制备方法 |
| TW200906774A (en) * | 2007-04-23 | 2009-02-16 | Shell Int Research | Process for the preparation of an 1,2-alkylene diol and a dialkylcarbonate |
| US20100121078A1 (en) * | 2008-05-06 | 2010-05-13 | Cyrille Paul Allais | Process for preparing alkanediol and dialkyl carbonate |
| DE102009030680A1 (de) * | 2009-06-26 | 2010-12-30 | Bayer Materialscience Ag | Verfahren zur Herstellung von Dialkylcarbonaten aus Alkylencarbonaten und Alkoholen |
| EP2464620B1 (en) * | 2009-08-12 | 2013-10-02 | Shell Internationale Research Maatschappij B.V. | Process for removing an alkanol impurity from a dialkyl carbonate stream |
| US9475751B2 (en) * | 2012-11-21 | 2016-10-25 | Covestro Deutschland Ag | Process for producing dialkyl carbonates |
| CN105646219A (zh) * | 2016-01-24 | 2016-06-08 | 辽宁会福化工有限公司 | 一种利用强酸性阳离子树脂催化合成碳酸二乙酯的方法 |
| WO2020075152A2 (en) | 2018-10-11 | 2020-04-16 | Shell Oil Company | A composition and uses thereof |
| WO2025057960A1 (ja) * | 2023-09-15 | 2025-03-20 | 旭化成株式会社 | アリール基を有するカーボネートの製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2994705A (en) * | 1958-12-08 | 1961-08-01 | Pure Oil Co | Preparation of cyclic alkylene carbonates in the presence of organic phosphonium compounds |
| US3803201A (en) * | 1971-02-22 | 1974-04-09 | Dow Chemical Co | Synthesis of dimethyl carbonate |
| DE2740243A1 (de) | 1977-09-07 | 1979-03-15 | Bayer Ag | Verfahren zur herstellung von dialkylcarbonaten |
| 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 |
| JPS6022698B2 (ja) | 1978-11-08 | 1985-06-03 | 日曹油化工業株式会社 | ジアルキル炭酸エステルの製法 |
| GB8307613D0 (en) | 1983-03-18 | 1983-04-27 | Bp Chem Int Ltd | Carbonates |
| US4508927A (en) * | 1983-08-02 | 1985-04-02 | The Halcon Sd Group, Inc. | Preparation of glycols from ethylene oxide |
| US4851555A (en) | 1984-10-25 | 1989-07-25 | Scientific Design Company, Inc. | Process for preparing alkylene oxides from alkylene carbonates |
| JPS61291545A (ja) | 1985-06-18 | 1986-12-22 | Daicel Chem Ind Ltd | 炭酸エステルの製造方法 |
| US4691041A (en) * | 1986-01-03 | 1987-09-01 | Texaco Inc. | Process for production of ethylene glycol and dimethyl carbonate |
| FR2608812B1 (fr) | 1986-12-23 | 1989-04-07 | Organo Synthese Ste Fse | Procede de preparation de carbonates organiques par transesterification |
| US4877886A (en) | 1987-06-19 | 1989-10-31 | Union Carbide Chemicals And Plastics Company Inc. | Process for the production of alkylene carbonate |
| JP2557099B2 (ja) | 1989-02-13 | 1996-11-27 | ダイセル化学工業株式会社 | ジメチルカーボネートの分離方法 |
| CN1060091A (zh) | 1990-09-21 | 1992-04-08 | 北京理工大学 | 二羟乙二肟的合成 |
| DE4030283A1 (de) * | 1990-09-25 | 1992-03-26 | Ruetgerswerke Ag | Verfahren zur herstellung cyclischer carbonate |
| GB2255972A (en) * | 1991-04-12 | 1992-11-25 | Davy Res & Dev Ltd | Production of diaryl carbonates. |
| 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 |
| KR940003917A (ko) | 1992-08-20 | 1994-03-14 | 고지마 아끼로 | 반응 제어방법 |
| DE4318892A1 (de) * | 1993-06-07 | 1994-12-08 | Bayer Ag | Verfahren zur Herstellung von Propylenglykolcarbonat |
| DE4318893A1 (de) * | 1993-06-07 | 1994-12-08 | Bayer Ag | Reaktor und damit durchzuführendes kontinuierliches Verfahren zur Herstellung von Ethylenglykolcarbonat bzw. Propylenglykolcarbonat |
| DE4342713A1 (de) * | 1993-12-15 | 1995-06-22 | Bayer Ag | Verfahren zur Abtrennung von Methanol aus einem Gemisch von Dimethylcarbonat und Methanol |
| CN1049212C (zh) | 1994-06-24 | 2000-02-09 | 华东理工大学 | 一种改进的碳酸二烷基酯的合成方法 |
| JP3652035B2 (ja) | 1995-10-31 | 2005-05-25 | 旭化成ケミカルズ株式会社 | ジアルキルカーボネートおよびジオールの連続的製造法 |
| US5763691A (en) | 1995-11-30 | 1998-06-09 | Mitsubishi Chemical Corporation | Ethylene glycol process |
| DE69620470T2 (de) * | 1995-12-22 | 2002-11-21 | Asahi Kasei Kabushiki Kaisha, Osaka | Verfahren zur kontinuierlichen herstellung von dialkylcarbonaten und diolen |
| DE19819586A1 (de) | 1998-04-30 | 1999-11-04 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von 1,3-Dioxolan-2-onen |
| JP2000005503A (ja) | 1998-06-24 | 2000-01-11 | Nippon Shokubai Co Ltd | 反応蒸留装置および反応蒸留方法 |
| SG77264A1 (en) * | 1998-08-10 | 2000-12-19 | Mitsubishi Chem Corp | Process for producing an alkylene glycol |
| JP2000113144A (ja) | 1998-10-06 | 2000-04-21 | Hitachi Chem Co Ltd | 非接触式icカード |
| US6156160A (en) * | 1998-10-07 | 2000-12-05 | Huntsman Petrochemical Corporation | Alkylene carbonate process |
| AU2827900A (en) * | 1999-03-03 | 2000-09-21 | Asahi Kasei Kabushiki Kaisha | Process for continuously producing dialkyl carbonate and diol |
| US6407279B1 (en) * | 1999-11-19 | 2002-06-18 | Exxonmobil Chemical Patents Inc. | Integrated process for preparing dialkyl carbonates and diols |
| US6294684B1 (en) * | 1999-12-08 | 2001-09-25 | General Electric Company | Method and apparatus for the continuous production of diaryl carbonates |
| JP3659109B2 (ja) * | 2000-01-19 | 2005-06-15 | 三菱化学株式会社 | エチレングリコールと炭酸エステルの併産方法 |
| US6392078B1 (en) * | 2000-06-12 | 2002-05-21 | Catalytic Distillation Technologies | Process and catalyst for making dialkyl carbonates |
| US6774256B2 (en) * | 2001-06-22 | 2004-08-10 | Exxonmobil Chemical Patents Inc. | Low corrosive integrated process for preparing dialkyl carbonates |
| WO2003006418A1 (en) | 2001-07-10 | 2003-01-23 | Mitsubishi Chemical Corporation | Method for producing dialkylcarbonate |
| JP2003081893A (ja) | 2001-09-10 | 2003-03-19 | Mitsui Chemicals Inc | ジアルキルカーボネートとグリコールの連続的同時製造方法 |
| US6573396B2 (en) * | 2001-10-12 | 2003-06-03 | Exxonmobil Chemical Patents Inc. | Co-production of dialkyl carbonates and diols with treatment of hydroxy alkyl carbonate |
| JP3969065B2 (ja) | 2001-11-19 | 2007-08-29 | 三菱化学株式会社 | アルキルアリールカーボネートの製造方法 |
| JP3960525B2 (ja) * | 2002-03-13 | 2007-08-15 | 三菱化学株式会社 | ジメチルカーボネート及びエチレングリコールの製造方法 |
| JP2003300936A (ja) * | 2002-04-09 | 2003-10-21 | Mitsui Chemicals Inc | ジアルキルカーボネートとグリコールの連続同時製造方法 |
| JP4000912B2 (ja) | 2002-05-30 | 2007-10-31 | 三菱化学株式会社 | ジメチルカーボネートの製造方法 |
| TW200503997A (en) | 2002-12-20 | 2005-02-01 | Shell Int Research | Process for the preparation of alkylene glycol |
| ES2293327T3 (es) | 2003-06-30 | 2008-03-16 | Shell Internationale Research Maatschappij B.V. | Procedimiento para la preparacion de carbonato de propileno. |
| CN1241900C (zh) | 2003-10-16 | 2006-02-15 | 华东理工大学 | 一种联产碳酸二烷基酯和二元醇的方法 |
| US20050148787A1 (en) | 2003-11-26 | 2005-07-07 | Beckers Johannes Gerhardus J. | Process for the preparation of propylene carbonate |
-
2007
- 2007-02-16 TW TW096106260A patent/TWI378087B/zh not_active IP Right Cessation
- 2007-02-20 CN CN2007800064459A patent/CN101389591B/zh not_active Expired - Fee Related
- 2007-02-20 JP JP2008555774A patent/JP5322658B2/ja not_active Expired - Fee Related
- 2007-02-20 KR KR1020087022816A patent/KR20080105088A/ko not_active Withdrawn
- 2007-02-20 EP EP07704658.9A patent/EP1986988B1/en not_active Not-in-force
- 2007-02-20 WO PCT/EP2007/051585 patent/WO2007096342A1/en not_active Ceased
- 2007-02-22 US US11/677,999 patent/US7563919B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7563919B2 (en) | 2009-07-21 |
| CN101389591B (zh) | 2012-06-27 |
| TW200738603A (en) | 2007-10-16 |
| EP1986988A1 (en) | 2008-11-05 |
| JP5322658B2 (ja) | 2013-10-23 |
| TWI378087B (en) | 2012-12-01 |
| EP1986988B1 (en) | 2015-06-10 |
| JP2009527529A (ja) | 2009-07-30 |
| CN101389591A (zh) | 2009-03-18 |
| WO2007096342A1 (en) | 2007-08-30 |
| US20070197814A1 (en) | 2007-08-23 |
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