CA2580569C - Improved method for alkoxylating active hydrogen containing compounds and the alkoxylated compounds made therefrom - Google Patents
Improved method for alkoxylating active hydrogen containing compounds and the alkoxylated compounds made therefrom Download PDFInfo
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- CA2580569C CA2580569C CA2580569A CA2580569A CA2580569C CA 2580569 C CA2580569 C CA 2580569C CA 2580569 A CA2580569 A CA 2580569A CA 2580569 A CA2580569 A CA 2580569A CA 2580569 C CA2580569 C CA 2580569C
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- Prior art keywords
- catalyst
- polyether
- mixture
- functionalizing
- vegetable oil
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims description 34
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- 239000001257 hydrogen Substances 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 143
- 239000000203 mixture Substances 0.000 claims abstract description 138
- 239000003999 initiator Substances 0.000 claims abstract description 101
- 229920000570 polyether Polymers 0.000 claims abstract description 44
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 41
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- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012508 resin bead Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 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
- 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
- C08G65/26—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 from cyclic ethers and other compounds
-
- 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
-
- 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
- C08G65/04—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 from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
-
- 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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2642—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 from cyclic ethers and other compounds characterised by the catalyst used
-
- 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
- C08G65/26—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 from cyclic ethers and other compounds
- C08G65/2696—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 from cyclic ethers and other compounds characterised by the process or apparatus used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62229804P | 2004-10-26 | 2004-10-26 | |
| US60/622,298 | 2004-10-26 | ||
| PCT/US2005/038220 WO2006047436A1 (en) | 2004-10-26 | 2005-10-24 | Improved method for alkoxylating active hydrogen containing compounds and the alkoxylated compounds made therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2580569A1 CA2580569A1 (en) | 2006-05-04 |
| CA2580569C true CA2580569C (en) | 2013-11-19 |
Family
ID=35945247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2580569A Expired - Fee Related CA2580569C (en) | 2004-10-26 | 2005-10-24 | Improved method for alkoxylating active hydrogen containing compounds and the alkoxylated compounds made therefrom |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20080125569A1 (enExample) |
| EP (1) | EP1807466B1 (enExample) |
| JP (1) | JP2008518088A (enExample) |
| KR (2) | KR101315527B1 (enExample) |
| CN (1) | CN101048441B (enExample) |
| AR (1) | AR051606A1 (enExample) |
| AT (1) | ATE460450T1 (enExample) |
| AU (1) | AU2005299522B2 (enExample) |
| BR (1) | BRPI0516890A (enExample) |
| CA (1) | CA2580569C (enExample) |
| DE (1) | DE602005019906D1 (enExample) |
| ES (1) | ES2338803T3 (enExample) |
| MX (1) | MX2007004969A (enExample) |
| MY (1) | MY144025A (enExample) |
| RU (1) | RU2007119396A (enExample) |
| WO (1) | WO2006047436A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060229375A1 (en) * | 2005-04-06 | 2006-10-12 | Yu-Ling Hsiao | Polyurethane foams made with alkoxylated vegetable oil hydroxylate |
| US8692030B1 (en) * | 2006-04-20 | 2014-04-08 | Pittsburg State University | Biobased-petrochemical hybrid polyols |
| CN100393767C (zh) * | 2006-07-24 | 2008-06-11 | 句容市宁武化工有限公司 | 聚氨酯泡沫用聚醚多元醇的制备方法及制得产品的应用 |
| WO2008026657A1 (fr) | 2006-08-31 | 2008-03-06 | Asahi Glass Company, Limited | Procédé de purification d'un composé polyéther |
| CN101802046B (zh) * | 2007-07-12 | 2014-06-18 | 陶氏环球技术有限责任公司 | 室温可固化聚合物及其前体 |
| PT2238195E (pt) * | 2008-01-29 | 2015-04-02 | Basf Se | Método para a produção de poliéter álcoois |
| DE102008011683A1 (de) * | 2008-02-28 | 2009-09-03 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyolen |
| EP2350191B1 (en) * | 2008-11-14 | 2013-09-11 | Dow Global Technologies LLC | Modified natural oils and products made therefrom |
| JP5342421B2 (ja) * | 2009-03-11 | 2013-11-13 | 信越化学工業株式会社 | 分子固定用基板の製造方法 |
| US20100317824A1 (en) * | 2009-06-15 | 2010-12-16 | Dow Global Technologies Inc. | Polyether derivatives of secondary hydroxy fatty acids and derivatives thereof |
| CN102471220A (zh) | 2009-07-10 | 2012-05-23 | 陶氏环球技术有限责任公司 | 仲羟基脂肪酸低聚物的酯及其制备 |
| CN102656209A (zh) * | 2009-12-09 | 2012-09-05 | 陶氏环球技术有限责任公司 | 仲羟基脂肪酸及其衍生物的聚醚衍生物 |
| US20110213170A1 (en) * | 2010-02-26 | 2011-09-01 | Daniele Vinci | Estolide derivatives useful as biolubricants |
| CN102906155A (zh) * | 2010-04-29 | 2013-01-30 | 陶氏环球技术有限责任公司 | 低聚酯烷氧基化物组合物 |
| US9115246B2 (en) | 2010-04-30 | 2015-08-25 | Basf Se | Polyether polyols, process for preparing polyether polyols and their use for producing polyurethanes |
| EP2563839B1 (de) * | 2010-04-30 | 2014-12-17 | Basf Se | Polyetherpolyole, verfahren zur herstellung von polyetherpolyolen, sowie deren verwendung zur herstellung von polyurethanen |
| JP5731651B2 (ja) * | 2010-08-20 | 2015-06-10 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリエーテルエステルポリオールの製造方法 |
| JP2014501826A (ja) * | 2010-12-20 | 2014-01-23 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | ポリエーテルエステルポリオールの製造方法 |
| WO2012091968A1 (en) | 2010-12-27 | 2012-07-05 | Dow Global Technologies Llc | Alkylene oxide polymerization using a double metal cyanide catalyst complex and a magnesium, group 3-group 15 metal or lanthanide series metal compound |
| US9012598B2 (en) * | 2012-08-01 | 2015-04-21 | Seeo, Inc. | Poly(ethyleneoxide) functionalization through alkylation |
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-
2005
- 2005-10-24 JP JP2007539026A patent/JP2008518088A/ja active Pending
- 2005-10-24 RU RU2007119396/04A patent/RU2007119396A/ru not_active Application Discontinuation
- 2005-10-24 WO PCT/US2005/038220 patent/WO2006047436A1/en not_active Ceased
- 2005-10-24 KR KR1020077009345A patent/KR101315527B1/ko not_active Expired - Fee Related
- 2005-10-24 CA CA2580569A patent/CA2580569C/en not_active Expired - Fee Related
- 2005-10-24 CN CN2005800367842A patent/CN101048441B/zh not_active Expired - Fee Related
- 2005-10-24 DE DE602005019906T patent/DE602005019906D1/de not_active Expired - Lifetime
- 2005-10-24 MY MYPI20054982A patent/MY144025A/en unknown
- 2005-10-24 AU AU2005299522A patent/AU2005299522B2/en not_active Ceased
- 2005-10-24 US US11/664,463 patent/US20080125569A1/en not_active Abandoned
- 2005-10-24 ES ES05817318T patent/ES2338803T3/es not_active Expired - Lifetime
- 2005-10-24 KR KR1020137015892A patent/KR101386288B1/ko not_active Expired - Fee Related
- 2005-10-24 EP EP05817318A patent/EP1807466B1/en not_active Expired - Lifetime
- 2005-10-24 MX MX2007004969A patent/MX2007004969A/es active IP Right Grant
- 2005-10-24 AT AT05817318T patent/ATE460450T1/de not_active IP Right Cessation
- 2005-10-24 BR BRPI0516890-2A patent/BRPI0516890A/pt not_active IP Right Cessation
- 2005-10-25 AR ARP050104460A patent/AR051606A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR051606A1 (es) | 2007-01-24 |
| EP1807466A1 (en) | 2007-07-18 |
| KR101386288B1 (ko) | 2014-04-17 |
| RU2007119396A (ru) | 2008-12-10 |
| CN101048441A (zh) | 2007-10-03 |
| AU2005299522B2 (en) | 2010-11-25 |
| BRPI0516890A (pt) | 2008-09-23 |
| MX2007004969A (es) | 2007-06-14 |
| ATE460450T1 (de) | 2010-03-15 |
| CN101048441B (zh) | 2010-11-03 |
| ES2338803T3 (es) | 2010-05-12 |
| JP2008518088A (ja) | 2008-05-29 |
| CA2580569A1 (en) | 2006-05-04 |
| DE602005019906D1 (de) | 2010-04-22 |
| WO2006047436A1 (en) | 2006-05-04 |
| US20080125569A1 (en) | 2008-05-29 |
| MY144025A (en) | 2011-07-29 |
| EP1807466B1 (en) | 2010-03-10 |
| KR20070083789A (ko) | 2007-08-24 |
| KR101315527B1 (ko) | 2013-10-08 |
| KR20130077902A (ko) | 2013-07-09 |
| AU2005299522A1 (en) | 2006-05-04 |
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