CN103509177B - 改进的醇解方法和用于从产物混合物分离催化剂的方法及其装置 - Google Patents
改进的醇解方法和用于从产物混合物分离催化剂的方法及其装置 Download PDFInfo
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- CN103509177B CN103509177B CN201310252804.6A CN201310252804A CN103509177B CN 103509177 B CN103509177 B CN 103509177B CN 201310252804 A CN201310252804 A CN 201310252804A CN 103509177 B CN103509177 B CN 103509177B
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- exchange resin
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- catalyst
- diester
- ion exchange
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- 239000003054 catalyst Substances 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 59
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000011347 resin Substances 0.000 claims abstract description 42
- 229920005989 resin Polymers 0.000 claims abstract description 42
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 35
- -1 polytetramethylene Polymers 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000003513 alkali Substances 0.000 claims abstract description 24
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims abstract description 11
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- 229920000570 polyether Polymers 0.000 claims description 39
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 38
- 229920005862 polyol Polymers 0.000 claims description 36
- 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 description 35
- 239000003456 ion exchange resin Substances 0.000 claims description 34
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 34
- 150000003077 polyols Chemical class 0.000 claims description 33
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000005690 diesters Chemical class 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- 239000002245 particle Substances 0.000 claims description 19
- 150000004703 alkoxides Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000011521 glass Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims 4
- 238000000643 oven drying Methods 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 229920001429 chelating resin Polymers 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 28
- 239000000047 product Substances 0.000 abstract description 21
- 238000006136 alcoholysis reaction Methods 0.000 abstract description 16
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 14
- 239000006227 byproduct Substances 0.000 abstract description 11
- 150000002500 ions Chemical class 0.000 abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 19
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 10
- 229920000909 polytetrahydrofuran Polymers 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000006140 methanolysis reaction Methods 0.000 description 6
- 238000000066 reactive distillation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
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- 230000002378 acidificating effect Effects 0.000 description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
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- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000002479 acid--base titration Methods 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 238000004448 titration Methods 0.000 description 2
- LSOKZQFZUDUBBI-UHFFFAOYSA-N 2,2-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)CCO1 LSOKZQFZUDUBBI-UHFFFAOYSA-N 0.000 description 1
- WUKHWLIEBSRTRH-UHFFFAOYSA-N 2-(2,2,3,3,4,4,5,5,5-nonafluoropentyl)oxirane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)CC1CO1 WUKHWLIEBSRTRH-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- AIUUAKHKOQFCKF-UHFFFAOYSA-N 3-ethyloxolane Chemical compound CCC1CCOC1 AIUUAKHKOQFCKF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920006309 Invista Polymers 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- ICFSECSJAGXHHZ-UHFFFAOYSA-N acetic acid oxolane Chemical compound CC(O)=O.CC(O)=O.C1CCOC1 ICFSECSJAGXHHZ-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 229920001400 block copolymer Polymers 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/30—Post-polymerisation treatment, e.g. recovery, purification, drying
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/24—Stationary reactors without moving elements inside
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261663015P | 2012-06-22 | 2012-06-22 | |
| US61/663,015 | 2012-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103509177A CN103509177A (zh) | 2014-01-15 |
| CN103509177B true CN103509177B (zh) | 2017-04-12 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310252804.6A Active CN103509177B (zh) | 2012-06-22 | 2013-06-24 | 改进的醇解方法和用于从产物混合物分离催化剂的方法及其装置 |
| CN201320364301.3U Expired - Lifetime CN204138580U (zh) | 2012-06-22 | 2013-06-24 | 用于从产物混合物分离催化剂的装置 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201320364301.3U Expired - Lifetime CN204138580U (zh) | 2012-06-22 | 2013-06-24 | 用于从产物混合物分离催化剂的装置 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20150158976A1 (https=) |
| EP (1) | EP2864392A4 (https=) |
| KR (1) | KR20150024840A (https=) |
| CN (2) | CN103509177B (https=) |
| BR (1) | BR112014029525A2 (https=) |
| IN (1) | IN2015MN00017A (https=) |
| RU (1) | RU2014149845A (https=) |
| WO (1) | WO2013191987A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105131274B (zh) * | 2015-08-20 | 2017-11-10 | 西安蓝晓科技新材料股份有限公司 | 一种用于聚四氢呋喃生产中除钠离子的方法 |
| EP3392288A1 (en) | 2017-04-21 | 2018-10-24 | Sulzer Chemtech AG | A process to prepare a cyclic oligomer and a cyclic oligomer obtainable thereby and a process to polymerize it |
| US12515212B2 (en) | 2022-10-12 | 2026-01-06 | Covestro Llc | Processes for purifying polyether polyols using ion exchange resins |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0376157B1 (en) * | 1988-12-29 | 1992-10-14 | BASF Corporation | Process for purification of catalysts from polyols using ion exchange resins |
| CN1204348A (zh) * | 1995-12-14 | 1999-01-06 | 纳幕尔杜邦公司 | 通过反应蒸馏实现聚醚多元醇酯的链烷醇分解 |
| JPH11279275A (ja) * | 1998-03-27 | 1999-10-12 | Mitsubishi Chemical Corp | ポリテトラメチレンエーテルグリコールの製造方法 |
| US6037381A (en) * | 1997-12-31 | 2000-03-14 | Basf Aktiengesellschaft | Preparation of polytetrahydrofuran with terminal hydroxyl groups using ion exchangers |
| DE10112116A1 (de) * | 2001-03-14 | 2002-09-19 | Basf Ag | Verfahren zur Herstellung von Polyetherolen mit definiertem CPR-Wert |
| CN101080433A (zh) * | 2005-03-17 | 2007-11-28 | 三菱化学株式会社 | 聚醚多元醇化合物的制造方法 |
| CN102026965A (zh) * | 2008-05-15 | 2011-04-20 | 旭化成化学株式会社 | 异氰酸酯的制造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| DE10140949A1 (de) | 2001-08-21 | 2003-03-06 | Basf Ag | Verfahren zur Herstellung einer alkoholischen Lösung von Polytetrahydrofuran mit endständigen OH-Gruppen |
| KR20140117590A (ko) * | 2012-01-26 | 2014-10-07 | 인비스타 테크놀러지스 에스.에이 알.엘. | 개선된 가알칸올분해 프로세스 |
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- 2013-06-12 WO PCT/US2013/045412 patent/WO2013191987A1/en not_active Ceased
- 2013-06-12 RU RU2014149845A patent/RU2014149845A/ru not_active Application Discontinuation
- 2013-06-12 BR BR112014029525A patent/BR112014029525A2/pt not_active IP Right Cessation
- 2013-06-12 KR KR1020147035429A patent/KR20150024840A/ko not_active Withdrawn
- 2013-06-12 IN IN17MUN2015 patent/IN2015MN00017A/en unknown
- 2013-06-12 EP EP13806916.6A patent/EP2864392A4/en not_active Withdrawn
- 2013-06-12 US US14/407,296 patent/US20150158976A1/en not_active Abandoned
- 2013-06-24 CN CN201310252804.6A patent/CN103509177B/zh active Active
- 2013-06-24 CN CN201320364301.3U patent/CN204138580U/zh not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2014149845A (ru) | 2016-08-10 |
| US20150158976A1 (en) | 2015-06-11 |
| IN2015MN00017A (https=) | 2015-10-16 |
| EP2864392A1 (en) | 2015-04-29 |
| CN103509177A (zh) | 2014-01-15 |
| EP2864392A4 (en) | 2015-12-23 |
| KR20150024840A (ko) | 2015-03-09 |
| WO2013191987A1 (en) | 2013-12-27 |
| BR112014029525A2 (pt) | 2017-06-27 |
| CN204138580U (zh) | 2015-02-04 |
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