JP2009504880A5 - - Google Patents
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- Publication number
- JP2009504880A5 JP2009504880A5 JP2008527017A JP2008527017A JP2009504880A5 JP 2009504880 A5 JP2009504880 A5 JP 2009504880A5 JP 2008527017 A JP2008527017 A JP 2008527017A JP 2008527017 A JP2008527017 A JP 2008527017A JP 2009504880 A5 JP2009504880 A5 JP 2009504880A5
- Authority
- JP
- Japan
- Prior art keywords
- ether glycol
- polytrimethylene ether
- polycondensation
- residual
- phase
- 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 Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 50
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 26
- -1 polytrimethylene Polymers 0.000 claims description 26
- 238000006068 polycondensation reaction Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 239000012074 organic phase Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000002009 diols Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/204,713 US7157607B1 (en) | 2005-08-16 | 2005-08-16 | Manufacture of polytrimethylene ether glycol |
| PCT/US2006/031409 WO2007021954A1 (en) | 2005-08-16 | 2006-08-11 | Manufacture of polytrimethylene ether glycol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009504880A JP2009504880A (ja) | 2009-02-05 |
| JP2009504880A5 true JP2009504880A5 (enExample) | 2009-09-24 |
Family
ID=37189046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008527017A Pending JP2009504880A (ja) | 2005-08-16 | 2006-08-11 | ポリトリメチレンエーテルグリコールの製造 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7157607B1 (enExample) |
| EP (1) | EP1917288B1 (enExample) |
| JP (1) | JP2009504880A (enExample) |
| KR (1) | KR20080035697A (enExample) |
| CN (1) | CN101248104B (enExample) |
| AT (1) | ATE506391T1 (enExample) |
| CA (1) | CA2616988A1 (enExample) |
| DE (1) | DE602006021434D1 (enExample) |
| ES (1) | ES2364577T3 (enExample) |
| TW (1) | TW200714632A (enExample) |
| WO (1) | WO2007021954A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7388115B2 (en) * | 2006-01-20 | 2008-06-17 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
| US20080108845A1 (en) * | 2006-11-07 | 2008-05-08 | Hari Babu Sunkara | Polytrimethylene ether glycol esters |
| US7714174B2 (en) * | 2007-03-27 | 2010-05-11 | E. I. Du Pont De Nemours And Company | Lower-color polytrimethylene ether glycol using hydride compounds |
| US20080242831A1 (en) * | 2007-03-27 | 2008-10-02 | Yanhui Niu | Lower-color polytrimethylene ether glycol using zero-valent metals |
| EP2181184A1 (en) * | 2007-08-24 | 2010-05-05 | E. I. du Pont de Nemours and Company | Lubrication oil compositions |
| CN101784643A (zh) * | 2007-08-24 | 2010-07-21 | 纳幕尔杜邦公司 | 润滑油组合物 |
| CN101842469A (zh) * | 2007-08-24 | 2010-09-22 | 纳幕尔杜邦公司 | 润滑油组合物 |
| AU2008293753A1 (en) * | 2007-08-24 | 2009-03-05 | E. I. Du Pont De Nemours And Company | Lubrication oil compositions |
| US8703681B2 (en) | 2007-08-24 | 2014-04-22 | E I Du Pont De Nemours And Company | Lubrication oil compositions |
| US8066757B2 (en) * | 2007-10-17 | 2011-11-29 | Mindframe, Inc. | Blood flow restoration and thrombus management methods |
| US8114957B2 (en) * | 2009-02-09 | 2012-02-14 | E. I. Du Pont De Nemours And Company | Process for preparing poly(trimethylene ether) glycol and copolymers thereof |
| US20100204439A1 (en) * | 2009-02-09 | 2010-08-12 | E.I. Du Pont De Nemours And Company | Processes for making poly(trimethylene ether) glycol using organophosphorous compound |
| TW201118131A (en) * | 2009-09-30 | 2011-06-01 | Du Pont | Polytrimethylene ether glycol or copolymers thereof having improved color and processes for their preparation |
| US20110112331A1 (en) * | 2009-11-09 | 2011-05-12 | E.I. Du Pont De Nemours And Company | Method for phase separation of polytrimethylene ether glycol in salt solution |
| WO2011084686A2 (en) * | 2009-12-21 | 2011-07-14 | E. I. Du Pont De Nemours And Company | Processes for producing polytrimethylene ether glycol and copolymers thereof |
| EP2686367B1 (en) * | 2011-03-17 | 2016-03-16 | University Of Ottawa | Methods for making polyglycerol |
| US8759559B2 (en) | 2012-04-18 | 2014-06-24 | E I Du Pont De Nemours And Company | Processes for preparing polytrimethylene ether glycol esters |
| US9145345B2 (en) * | 2012-08-30 | 2015-09-29 | Glyeco, Inc. | Method and apparatus for processing glycol |
| CN106543427B (zh) * | 2016-11-01 | 2018-08-28 | 万华化学集团股份有限公司 | 一种脱除聚醚多元醇中挥发性物质并降低气味的方法 |
| KR102492665B1 (ko) * | 2017-09-29 | 2023-01-26 | 에스케이케미칼 주식회사 | 폴리트리메틸렌 에테르 글리콜 및 이의 제조 방법 |
| KR20230037280A (ko) * | 2021-09-09 | 2023-03-16 | 에스케이케미칼 주식회사 | 폴리트리메틸렌 에테르 글리콜의 제조 방법 및 이에 따라 제조된 폴리트리메틸렌 에테르 글리콜 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0784517B2 (ja) * | 1987-04-30 | 1995-09-13 | ダイセル化学工業株式会社 | 新規ブロツク・コポリエ−テル・グリコ−ル |
| DE3926136A1 (de) | 1989-08-08 | 1991-02-14 | Degussa | Verfahren zur herstellung von 1,3-propandiol |
| DE4132663C2 (de) | 1991-10-01 | 1993-10-14 | Degussa | Verfahren zum Herstellen von 1,3-Propandiol durch Hydrieren von Hydroxypropionaldehyd |
| DE4138981A1 (de) | 1991-11-27 | 1993-06-03 | Degussa | Verfahren zur herstellung von 3-hydroxyalkanalen |
| DE4138982A1 (de) | 1991-11-27 | 1993-06-03 | Degussa | Verfahren zur herstellung von 3-hydroxyalkanalen |
| DE4218282A1 (de) | 1992-06-03 | 1993-12-09 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| DE4222708A1 (de) | 1992-07-10 | 1994-01-13 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| US5686276A (en) | 1995-05-12 | 1997-11-11 | E. I. Du Pont De Nemours And Company | Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism |
| US5633362A (en) | 1995-05-12 | 1997-05-27 | E. I. Du Pont De Nemours And Company | Production of 1,3-propanediol from glycerol by recombinant bacteria expressing recombinant diol dehydratase |
| DE19703383A1 (de) | 1997-01-30 | 1998-08-06 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| US5962745A (en) | 1997-02-14 | 1999-10-05 | E. I. Du Pont De Nemours And Company | Process for preparing 3-hydroxyalkanals |
| KR20010013907A (ko) | 1997-06-18 | 2001-02-26 | 메리 이. 보울러 | 3-히드록시프로피온알데히드의 수소화에 의한1,3-프로판디올의 제조 방법 |
| AUPO761697A0 (en) * | 1997-06-30 | 1997-07-24 | Cardiac Crc Nominees Pty Limited | Process for the purification of polyethers |
| US6235948B1 (en) | 1998-08-18 | 2001-05-22 | E. I. Du Pont De Nemours And Company | Process for the purification of 1,3-propanediol |
| AU5798199A (en) | 1998-09-04 | 2000-03-27 | E.I. Du Pont De Nemours And Company | Two-stage process for the production of 1,3-propanediol by catalytic hydrogenation of 3-hydroxypropanal |
| US6331264B1 (en) | 1999-03-31 | 2001-12-18 | E. I. Du Pont De Nemours And Company | Low emission polymer compositions |
| US6277289B1 (en) | 1999-07-01 | 2001-08-21 | E. I. Du Pont De Nemours And Company | Treatment of aqueous aldehyde waste streams |
| US6342646B1 (en) | 1999-07-30 | 2002-01-29 | E. I. Du Pont De Nemours And Company | Catalytic hydrogenation of 3-hydroxypropanal to 1,3-propanediol |
| US6284930B1 (en) | 1999-07-30 | 2001-09-04 | E.I. Du Pont De Nemours And Company | Process for the preparation of 3-hydroxypropanal |
| WO2001044348A1 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| EP1237835B1 (en) * | 1999-12-17 | 2006-09-20 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| JP4658296B2 (ja) * | 2000-09-07 | 2011-03-23 | 株式会社Adeka | （ポリ）グリセリルエーテルの製造方法 |
| US20040030095A1 (en) | 2002-08-09 | 2004-02-12 | Sunkara Hari B. | Poly(trimethylene-ethylene ether) glycols |
| US6608168B1 (en) | 2002-08-09 | 2003-08-19 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether esters |
| WO2004048440A1 (ja) * | 2002-11-22 | 2004-06-10 | Mitsubishi Chemical Corporation | ポリエーテルポリオールの製造方法 |
| JP2004182974A (ja) | 2002-11-22 | 2004-07-02 | Mitsubishi Chemicals Corp | ポリエーテルポリオールの製造方法 |
| JP4908218B2 (ja) | 2003-05-06 | 2012-04-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生化学的に誘導された１，３−プロパンジオールの水素化 |
| DE602004028359D1 (de) | 2003-05-06 | 2010-09-09 | Du Pont | Reinigung von biologisch produziertem 1,3-propandiol |
| US7084311B2 (en) | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| US7342142B2 (en) * | 2003-05-06 | 2008-03-11 | E.I. Du Pont De Nemours And Company | Hydrogenation of polytrimethylene ether glycol |
| JP2004352713A (ja) | 2003-05-08 | 2004-12-16 | Mitsubishi Chemicals Corp | １，３−プロパンジオールの製造方法 |
| CN1816509A (zh) | 2003-05-08 | 2006-08-09 | 三菱化学株式会社 | 1,3－丙二醇的制备方法 |
| US7074969B2 (en) | 2004-06-18 | 2006-07-11 | E.I. Du Pont De Nemours And Company | Process for preparation of polytrimethylene ether glycols |
| JP2006342344A (ja) * | 2005-05-13 | 2006-12-21 | Mitsubishi Chemicals Corp | ポリエーテルポリオールの製造方法 |
-
2005
- 2005-08-16 US US11/204,713 patent/US7157607B1/en not_active Expired - Fee Related
-
2006
- 2006-08-09 TW TW095129138A patent/TW200714632A/zh unknown
- 2006-08-11 DE DE602006021434T patent/DE602006021434D1/de active Active
- 2006-08-11 JP JP2008527017A patent/JP2009504880A/ja active Pending
- 2006-08-11 KR KR1020087006229A patent/KR20080035697A/ko not_active Ceased
- 2006-08-11 AT AT06789699T patent/ATE506391T1/de not_active IP Right Cessation
- 2006-08-11 WO PCT/US2006/031409 patent/WO2007021954A1/en not_active Ceased
- 2006-08-11 ES ES06789699T patent/ES2364577T3/es active Active
- 2006-08-11 CN CN2006800299106A patent/CN101248104B/zh not_active Expired - Fee Related
- 2006-08-11 EP EP06789699A patent/EP1917288B1/en not_active Not-in-force
- 2006-08-11 CA CA002616988A patent/CA2616988A1/en not_active Abandoned
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