CA2703786A1 - Process to make a poly(trimethylene carbonate) glycol - Google Patents
Process to make a poly(trimethylene carbonate) glycol Download PDFInfo
- Publication number
- CA2703786A1 CA2703786A1 CA2703786A CA2703786A CA2703786A1 CA 2703786 A1 CA2703786 A1 CA 2703786A1 CA 2703786 A CA2703786 A CA 2703786A CA 2703786 A CA2703786 A CA 2703786A CA 2703786 A1 CA2703786 A1 CA 2703786A1
- Authority
- CA
- Canada
- Prior art keywords
- trimethylene carbonate
- poly
- catalyst
- unsubstituted
- glycol
- 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.)
- Abandoned
Links
- -1 poly(trimethylene carbonate) Polymers 0.000 title claims abstract description 65
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 229920000166 polytrimethylene carbonate Polymers 0.000 title claims abstract description 41
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 27
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 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 25
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical class O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 60
- 239000011541 reaction mixture Substances 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 14
- 150000002009 diols Chemical class 0.000 claims description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 230000008014 freezing Effects 0.000 claims description 4
- 238000007710 freezing Methods 0.000 claims description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 3
- SELFXCFVPOJKBE-UHFFFAOYSA-N 2-(1-ethenoxypropan-2-yloxy)ethanesulfonic acid Chemical compound C=COCC(C)OCCS(O)(=O)=O SELFXCFVPOJKBE-UHFFFAOYSA-N 0.000 claims description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 238000006116 polymerization reaction Methods 0.000 abstract description 7
- 229920000557 Nafion® Polymers 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 14
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 12
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000376 reactant Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000002306 biochemical method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229920000554 ionomer Polymers 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001692 polycarbonate urethane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99147407P | 2007-11-30 | 2007-11-30 | |
| US60/991,474 | 2007-11-30 | ||
| PCT/US2008/084684 WO2009070582A1 (en) | 2007-11-30 | 2008-11-25 | Process to make a poly(trimethylene carbonate) glycol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2703786A1 true CA2703786A1 (en) | 2009-06-04 |
Family
ID=40347853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2703786A Abandoned CA2703786A1 (en) | 2007-11-30 | 2008-11-25 | Process to make a poly(trimethylene carbonate) glycol |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8252885B2 (enExample) |
| EP (1) | EP2215141B1 (enExample) |
| JP (1) | JP2011505467A (enExample) |
| KR (1) | KR20100102628A (enExample) |
| CN (1) | CN101878245A (enExample) |
| AT (1) | ATE541878T1 (enExample) |
| AU (1) | AU2008329773A1 (enExample) |
| BR (1) | BRPI0819041A2 (enExample) |
| CA (1) | CA2703786A1 (enExample) |
| ES (1) | ES2380173T3 (enExample) |
| MX (1) | MX2010005759A (enExample) |
| TW (1) | TW200938564A (enExample) |
| WO (1) | WO2009070582A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2010005760A (es) * | 2007-11-30 | 2010-06-11 | Du Pont | Composiciones de y procesos para producir poli(trimetilen glicol carbonato trimetilen glicol eter) diol. |
| CN108659718A (zh) * | 2018-04-14 | 2018-10-16 | 江苏天时新材料科技有限公司 | 一种车灯专用的高黏性密封蜡制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05339360A (ja) * | 1992-06-12 | 1993-12-21 | Idemitsu Petrochem Co Ltd | ポリカーボネートの製造方法 |
| JPH0710920A (ja) | 1992-12-01 | 1995-01-13 | Nippon Paint Co Ltd | 環状カーボネート化合物のアルコール性水酸基への開環付加方法 |
| JPH09176152A (ja) * | 1995-12-28 | 1997-07-08 | Sumitomo Bakelite Co Ltd | 環状カーボナート化合物の重合方法 |
| US6451949B2 (en) * | 2000-02-29 | 2002-09-17 | Shell Oil Company | Method for production of poly (trimethylene carbonate) |
| KR20100102629A (ko) * | 2007-11-30 | 2010-09-24 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 트라이메틸렌 카보네이트의 폴리(트라이메틸렌 글리콜 카보네이트 트라이메틸렌 글리콜 에테르) 다이올에로의 무용매 중합법 |
-
2008
- 2008-11-25 KR KR1020107014389A patent/KR20100102628A/ko not_active Withdrawn
- 2008-11-25 BR BRPI0819041 patent/BRPI0819041A2/pt not_active IP Right Cessation
- 2008-11-25 AT AT08854951T patent/ATE541878T1/de active
- 2008-11-25 WO PCT/US2008/084684 patent/WO2009070582A1/en not_active Ceased
- 2008-11-25 JP JP2010536126A patent/JP2011505467A/ja active Pending
- 2008-11-25 US US12/277,633 patent/US8252885B2/en not_active Expired - Fee Related
- 2008-11-25 AU AU2008329773A patent/AU2008329773A1/en not_active Abandoned
- 2008-11-25 CN CN2008801183106A patent/CN101878245A/zh active Pending
- 2008-11-25 MX MX2010005759A patent/MX2010005759A/es unknown
- 2008-11-25 ES ES08854951T patent/ES2380173T3/es active Active
- 2008-11-25 EP EP08854951A patent/EP2215141B1/en not_active Not-in-force
- 2008-11-25 CA CA2703786A patent/CA2703786A1/en not_active Abandoned
- 2008-11-28 TW TW097146470A patent/TW200938564A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN101878245A (zh) | 2010-11-03 |
| ES2380173T3 (es) | 2012-05-09 |
| WO2009070582A1 (en) | 2009-06-04 |
| US20090143562A1 (en) | 2009-06-04 |
| JP2011505467A (ja) | 2011-02-24 |
| US8252885B2 (en) | 2012-08-28 |
| MX2010005759A (es) | 2010-06-09 |
| BRPI0819041A2 (pt) | 2015-05-05 |
| KR20100102628A (ko) | 2010-09-24 |
| ATE541878T1 (de) | 2012-02-15 |
| EP2215141A1 (en) | 2010-08-11 |
| TW200938564A (en) | 2009-09-16 |
| AU2008329773A1 (en) | 2009-06-04 |
| EP2215141B1 (en) | 2012-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20131126 |