JP2011501692A - アルキレンオキサイドをアルキレングリコールに転換するために有用な固体触媒 - Google Patents
アルキレンオキサイドをアルキレングリコールに転換するために有用な固体触媒 Download PDFInfo
- Publication number
- JP2011501692A JP2011501692A JP2010528950A JP2010528950A JP2011501692A JP 2011501692 A JP2011501692 A JP 2011501692A JP 2010528950 A JP2010528950 A JP 2010528950A JP 2010528950 A JP2010528950 A JP 2010528950A JP 2011501692 A JP2011501692 A JP 2011501692A
- Authority
- JP
- Japan
- Prior art keywords
- ion exchange
- exchange resin
- alkylene
- glycol
- solid catalyst
- 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.)
- Pending
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 125000002947 alkylene group Chemical group 0.000 title claims abstract description 41
- -1 alkylene glycol Chemical compound 0.000 title claims abstract description 39
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000011949 solid catalyst Substances 0.000 title claims description 17
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 64
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 64
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract description 56
- 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 claims abstract description 52
- 239000003054 catalyst Substances 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 32
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 24
- 230000003197 catalytic effect Effects 0.000 claims abstract description 15
- 239000004793 Polystyrene Substances 0.000 claims abstract description 12
- 229920002223 polystyrene Polymers 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 125000005496 phosphonium group Chemical group 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000001450 anions Chemical class 0.000 claims description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 5
- 229920005990 polystyrene resin Polymers 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 2
- 206010016807 Fluid retention Diseases 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 abstract description 12
- 230000036571 hydration Effects 0.000 abstract description 9
- 239000007787 solid Substances 0.000 abstract description 4
- 239000011347 resin Substances 0.000 description 20
- 229920005989 resin Polymers 0.000 description 20
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000003957 anion exchange resin Substances 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 239000011324 bead Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 239000000376 reactant Substances 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical group C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
Classifications
-
- 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
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective 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)
- Catalysts (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/872,318 US8053609B2 (en) | 2007-10-15 | 2007-10-15 | Solid catalyst useful for converting an alkylene oxide to an alkylene glycol |
| PCT/US2008/078654 WO2009051972A1 (en) | 2007-10-15 | 2008-10-03 | Solid catalyst useful for converting an alkylene oxide to an alkylene glycol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011501692A true JP2011501692A (ja) | 2011-01-13 |
| JP2011501692A5 JP2011501692A5 (enExample) | 2011-09-29 |
Family
ID=40534877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010528950A Pending JP2011501692A (ja) | 2007-10-15 | 2008-10-03 | アルキレンオキサイドをアルキレングリコールに転換するために有用な固体触媒 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8053609B2 (enExample) |
| EP (1) | EP2212023B1 (enExample) |
| JP (1) | JP2011501692A (enExample) |
| KR (1) | KR101502921B1 (enExample) |
| CN (1) | CN101821002B (enExample) |
| BR (1) | BRPI0818057B1 (enExample) |
| CA (1) | CA2702498A1 (enExample) |
| MX (1) | MX2010004077A (enExample) |
| RU (1) | RU2470706C2 (enExample) |
| TW (1) | TWI527625B (enExample) |
| WO (1) | WO2009051972A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106478375A (zh) * | 2015-08-25 | 2017-03-08 | 中国石油化工股份有限公司 | 一种以阴离子交换树脂为催化剂合成邻二醇类化合物的方法 |
| CN106478374A (zh) * | 2015-08-25 | 2017-03-08 | 中国石油化工股份有限公司 | 一种通过开环反应制备邻二醇类化合物的方法 |
| CN106478365A (zh) * | 2015-08-25 | 2017-03-08 | 中国石油化工股份有限公司 | 一种邻二醇类化合物的合成方法 |
| CN112239393B (zh) * | 2019-07-17 | 2023-06-06 | 中国石油化工股份有限公司 | 纳米复合离子交换树脂催化剂及其应用 |
| CN116020557A (zh) * | 2021-10-25 | 2023-04-28 | 中国石油化工股份有限公司 | 离子交换树脂催化剂及其制备方法和应用 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6314744A (ja) * | 1986-06-30 | 1988-01-21 | ユニオン、カ−バイド、コ−ポレ−ション | メタレ−ト含有固体を使用するアルキレングリコ−ルの改良製造方法 |
| JPH07204523A (ja) * | 1994-01-19 | 1995-08-08 | Mitsubishi Chem Corp | 陰イオン交換樹脂およびその製造方法 |
| JPH07289912A (ja) * | 1994-03-01 | 1995-11-07 | Mitsubishi Chem Corp | 固体塩基性触媒 |
| JPH1112206A (ja) * | 1997-04-30 | 1999-01-19 | Mitsubishi Chem Corp | アルキレングリコール類の製造方法 |
| JP2002030112A (ja) * | 2000-07-18 | 2002-01-31 | Mitsubishi Chemicals Corp | アニオン交換樹脂、その製法及びこれを用いるクランピング防止方法 |
| JP2002508340A (ja) * | 1997-12-18 | 2002-03-19 | ザ ダウ ケミカル カンパニー | エチレングリコールの製造方法 |
| JP2002532448A (ja) * | 1998-12-14 | 2002-10-02 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | アルキレンオキシドの触媒的加水分解におけるカルボン酸塩 |
| JP2002532446A (ja) * | 1998-12-14 | 2002-10-02 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | アルキレンオキシドの触媒加水分解における第四級ホスホニウム塩触媒 |
| JP2005060289A (ja) * | 2003-08-11 | 2005-03-10 | Mitsui Chemicals Inc | フェノール類の製造方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6056141B2 (ja) | 1981-02-24 | 1985-12-09 | 株式会社日本触媒 | アルキレングリコールの製造方法 |
| US4560813A (en) | 1984-03-28 | 1985-12-24 | Union Carbide Corporation | Processes for the production of alkylene glycol in the presence of organometalate |
| RU2002726C1 (ru) | 1992-05-19 | 1993-11-15 | Государственное научно-производственное предпри тие "Совинтех" | Способ получени алкиленгликолей |
| RU2001901C1 (ru) | 1992-05-19 | 1993-10-30 | Государственное научно-производственное предпри тие "Совинтех" | Способ получени алкиленгликолей |
| CZ292902B6 (cs) | 1994-01-31 | 2004-01-14 | Shell Internationale Research Maatschappij B. V. | Způsob přípravy ethylenglykolu |
| WO1997033850A1 (fr) | 1996-03-11 | 1997-09-18 | Valery Fedorovich Shvets | Procede de production d'alcyleneglycols |
| CA2268158A1 (en) * | 1996-10-04 | 1998-04-09 | The Dow Chemical Company | A method for producing glycols |
| US6156942A (en) * | 1998-12-14 | 2000-12-05 | Shell Oil Company | Catalyst stabilizing additive in the hydrolysis of alkylene oxides |
| MY121124A (en) * | 1998-12-14 | 2005-12-30 | Shell Int Research | Catalyst stabilising additive in the hydrolysis of alkylene oxides |
| US6153801A (en) * | 1998-12-14 | 2000-11-28 | Shell Oil Company | Carboxylates in catalytic hydrolysis of alkylene oxides |
| US6211419B1 (en) * | 2000-04-24 | 2001-04-03 | The Dow Chemical Company | Process for the preparation of alkylene glycols |
| US6730816B2 (en) * | 2000-12-29 | 2004-05-04 | Rohm And Haas Company | High productivity bisphenol-A catalyst |
-
2007
- 2007-10-15 US US11/872,318 patent/US8053609B2/en active Active
-
2008
- 2008-10-03 EP EP08838859.0A patent/EP2212023B1/en active Active
- 2008-10-03 JP JP2010528950A patent/JP2011501692A/ja active Pending
- 2008-10-03 CN CN200880111607.XA patent/CN101821002B/zh active Active
- 2008-10-03 CA CA2702498A patent/CA2702498A1/en not_active Abandoned
- 2008-10-03 RU RU2010119451/04A patent/RU2470706C2/ru active
- 2008-10-03 BR BRPI0818057-1A patent/BRPI0818057B1/pt active IP Right Grant
- 2008-10-03 KR KR1020107010705A patent/KR101502921B1/ko active Active
- 2008-10-03 MX MX2010004077A patent/MX2010004077A/es active IP Right Grant
- 2008-10-03 WO PCT/US2008/078654 patent/WO2009051972A1/en not_active Ceased
- 2008-10-09 TW TW097139098A patent/TWI527625B/zh active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6314744A (ja) * | 1986-06-30 | 1988-01-21 | ユニオン、カ−バイド、コ−ポレ−ション | メタレ−ト含有固体を使用するアルキレングリコ−ルの改良製造方法 |
| JPH07204523A (ja) * | 1994-01-19 | 1995-08-08 | Mitsubishi Chem Corp | 陰イオン交換樹脂およびその製造方法 |
| JPH07289912A (ja) * | 1994-03-01 | 1995-11-07 | Mitsubishi Chem Corp | 固体塩基性触媒 |
| JPH1112206A (ja) * | 1997-04-30 | 1999-01-19 | Mitsubishi Chem Corp | アルキレングリコール類の製造方法 |
| JP2002508340A (ja) * | 1997-12-18 | 2002-03-19 | ザ ダウ ケミカル カンパニー | エチレングリコールの製造方法 |
| JP2002532448A (ja) * | 1998-12-14 | 2002-10-02 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | アルキレンオキシドの触媒的加水分解におけるカルボン酸塩 |
| JP2002532446A (ja) * | 1998-12-14 | 2002-10-02 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | アルキレンオキシドの触媒加水分解における第四級ホスホニウム塩触媒 |
| JP2002030112A (ja) * | 2000-07-18 | 2002-01-31 | Mitsubishi Chemicals Corp | アニオン交換樹脂、その製法及びこれを用いるクランピング防止方法 |
| JP2005060289A (ja) * | 2003-08-11 | 2005-03-10 | Mitsui Chemicals Inc | フェノール類の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0818057B1 (pt) | 2022-05-17 |
| KR20100090260A (ko) | 2010-08-13 |
| BRPI0818057A2 (pt) | 2015-03-31 |
| EP2212023B1 (en) | 2016-05-11 |
| CN101821002B (zh) | 2014-11-05 |
| TWI527625B (zh) | 2016-04-01 |
| US20090099393A1 (en) | 2009-04-16 |
| RU2010119451A (ru) | 2011-11-27 |
| CN101821002A (zh) | 2010-09-01 |
| RU2470706C2 (ru) | 2012-12-27 |
| KR101502921B1 (ko) | 2015-03-16 |
| MX2010004077A (es) | 2010-05-24 |
| US8053609B2 (en) | 2011-11-08 |
| WO2009051972A1 (en) | 2009-04-23 |
| CA2702498A1 (en) | 2009-04-23 |
| EP2212023A4 (en) | 2010-12-01 |
| TW200934586A (en) | 2009-08-16 |
| EP2212023A1 (en) | 2010-08-04 |
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