JP2009504880A5 - - Google Patents
Download PDFInfo
- 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 |
| US20080242831A1 (en) * | 2007-03-27 | 2008-10-02 | Yanhui Niu | Lower-color polytrimethylene ether glycol using zero-valent metals |
| US7714174B2 (en) * | 2007-03-27 | 2010-05-11 | E. I. Du Pont De Nemours And Company | Lower-color polytrimethylene ether glycol using hydride compounds |
| US8703681B2 (en) | 2007-08-24 | 2014-04-22 | E I Du Pont De Nemours And Company | Lubrication oil compositions |
| CA2696371A1 (en) * | 2007-08-24 | 2009-03-05 | E.I. Du Pont De Nemours And Company | Lubrication oil compositions |
| BRPI0815314A2 (pt) * | 2007-08-24 | 2017-05-09 | Du Pont | coposição de óleo lubrificante |
| BRPI0815293A2 (pt) * | 2007-08-24 | 2017-05-09 | Du Pont | "composição de óleo lubrificante" |
| CA2696369A1 (en) * | 2007-08-24 | 2009-03-05 | 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 |
| 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 |
| 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 |
| US8598391B2 (en) * | 2009-09-30 | 2013-12-03 | E I Du Pont De Nemours And Company | 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 |
| EP2516505B1 (en) * | 2009-12-21 | 2014-09-17 | E.I. Du Pont De Nemours And Company | Processes for producing polytrimethylene ether glycol |
| CN103282406B (zh) * | 2011-03-17 | 2015-07-22 | 渥太华大学 | 用于制备聚甘油的方法 |
| 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 |
| DE4138982A1 (de) | 1991-11-27 | 1993-06-03 | Degussa | Verfahren zur herstellung von 3-hydroxyalkanalen |
| DE4138981A1 (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 |
| DE69817356T2 (de) | 1997-06-18 | 2004-07-08 | E.I. Du Pont De Nemours And Co., Wilmington | Verfahren zur herstellung von 1,3-propandiol durch hydrierung von 3-hydroxypropanal |
| 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 |
| JP4328026B2 (ja) | 1998-09-04 | 2009-09-09 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ３−ヒドロキシプロパナールの接触水素化による１，３−プロパンジオールの二段階製造法 |
| 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 |
| US6284930B1 (en) | 1999-07-30 | 2001-09-04 | E.I. Du Pont De Nemours And Company | Process for the preparation of 3-hydroxypropanal |
| 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 |
| AU2270901A (en) * | 1999-12-17 | 2001-06-25 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| EP1246861B1 (en) * | 1999-12-17 | 2006-05-17 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| 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 |
| US7342142B2 (en) * | 2003-05-06 | 2008-03-11 | E.I. Du Pont De Nemours And Company | Hydrogenation of polytrimethylene ether glycol |
| US7919658B2 (en) | 2003-05-06 | 2011-04-05 | E. I. Du Pont De Nemours And Company | Purification of biologically-produced 1,3-propanediol |
| US7084311B2 (en) | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| BRPI0410686A (pt) | 2003-05-06 | 2006-06-20 | Du Pont | processo e composição |
| WO2004099110A1 (ja) | 2003-05-08 | 2004-11-18 | Mitsubishi Chemical Corporation | １,３−プロパンジオールの製造方法 |
| 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 |
| 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 CN CN2006800299106A patent/CN101248104B/zh not_active Expired - Fee Related
- 2006-08-11 AT AT06789699T patent/ATE506391T1/de not_active IP Right Cessation
- 2006-08-11 JP JP2008527017A patent/JP2009504880A/ja active Pending
- 2006-08-11 WO PCT/US2006/031409 patent/WO2007021954A1/en not_active Ceased
- 2006-08-11 KR KR1020087006229A patent/KR20080035697A/ko not_active Ceased
- 2006-08-11 EP EP06789699A patent/EP1917288B1/en not_active Expired - Lifetime
- 2006-08-11 DE DE602006021434T patent/DE602006021434D1/de not_active Expired - Lifetime
- 2006-08-11 ES ES06789699T patent/ES2364577T3/es not_active Expired - Lifetime
- 2006-08-11 CA CA002616988A patent/CA2616988A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2440379A1 (en) | Glycolide production process, and glycolic acid oligomer for glycolide production | |
| US7157607B1 (en) | Manufacture of polytrimethylene ether glycol | |
| JP2008503486A5 (enExample) | ||
| CN1112559A (zh) | 丙交酯的提纯方法 | |
| EP1973962B1 (en) | Manufacture of polytrimethylene ether glycol | |
| JP2011520949A (ja) | 粗製グリセロールの精製方法 | |
| JP2013515060A5 (enExample) | ||
| CN108239265B (zh) | 有机磷腈盐催化剂及其制备方法和用途 | |
| RU97120887A (ru) | Способ обработки реакционных смесей, образующихся при окислении циклогексана | |
| JP5579737B2 (ja) | 有機カーボナート流からアルカノール不純物を除去する方法 | |
| JP2012510450A5 (enExample) | ||
| CN102267903A (zh) | (甲基)丙烯酸羟烷基酯的制造方法 | |
| CN103842351A (zh) | 包括液液萃取步骤的用于由粗甘油生产二氧戊环化合物的方法 | |
| JP5206736B2 (ja) | グリシジルオキシブチルアクリレートの製造方法 | |
| CN109153631B (zh) | 用于生产酯的方法 | |
| CN112409182A (zh) | 一种乳酸薄荷酯的合成及提纯分离方法 | |
| CN105017020A (zh) | 亚丙烯双乙酯的合成方法 | |
| CN103842352A (zh) | 从粗甘油生产二氧戊环化合物的方法 | |
| EP2609069B1 (fr) | Procede de preparation d'adipate de di-alpha-methylbenzyle | |
| JP5212953B2 (ja) | 光学活性γ−ラクトンの製造法 | |
| JP5547417B2 (ja) | レゾルシンホルムアルデヒド樹脂の製造方法 | |
| JP2023035371A (ja) | イオン液体のカチオン成分の回収方法およびイオン液体の再生方法 | |
| KR100988313B1 (ko) | 초산 회수방법 및 이에 의해 회수된 초산 | |
| CN101326158A (zh) | 用于制备纯化的甲酰基环丙烷化合物及其中间体的方法 | |
| WO2007064144A1 (en) | Method for extracting sterol from soybean deodorizer sludge |