JP2012522823A5 - - Google Patents
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- Publication number
- JP2012522823A5 JP2012522823A5 JP2012503978A JP2012503978A JP2012522823A5 JP 2012522823 A5 JP2012522823 A5 JP 2012522823A5 JP 2012503978 A JP2012503978 A JP 2012503978A JP 2012503978 A JP2012503978 A JP 2012503978A JP 2012522823 A5 JP2012522823 A5 JP 2012522823A5
- Authority
- JP
- Japan
- Prior art keywords
- ester
- cyclohexanediol
- process according
- esterification
- fraction
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 15
- 238000004821 distillation Methods 0.000 claims 11
- -1 6-hydroxycaproic acid ester Chemical class 0.000 claims 8
- 230000032050 esterification Effects 0.000 claims 8
- 238000005886 esterification reaction Methods 0.000 claims 8
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims 7
- 239000000047 product Substances 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 6
- 238000005984 hydrogenation reaction Methods 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 239000002184 metal Substances 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 3
- 229910052707 ruthenium Inorganic materials 0.000 claims 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- 235000011037 adipic acid Nutrition 0.000 claims 2
- 239000001361 adipic acid Substances 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 2
- 229910017052 cobalt Inorganic materials 0.000 claims 2
- 239000010941 cobalt Substances 0.000 claims 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 2
- ODZTXUXIYGJLMC-UHFFFAOYSA-N 2-hydroxycyclohexan-1-one Chemical compound OC1CCCCC1=O ODZTXUXIYGJLMC-UHFFFAOYSA-N 0.000 claims 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 claims 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- CEQMDSFVFKDZCR-UHFFFAOYSA-N butyl 6-hydroxyhexanoate Chemical compound CCCCOC(=O)CCCCCO CEQMDSFVFKDZCR-UHFFFAOYSA-N 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- ARSRKIQSWHMOJO-UHFFFAOYSA-N cyclohexane cyclohexanone Chemical compound C1CCCCC1.C1(CCCCC1)=O.C1(CCCCC1)=O ARSRKIQSWHMOJO-UHFFFAOYSA-N 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YDJZXHZRXDLCEH-UHFFFAOYSA-N methyl 6-hydroxyhexanoate Chemical compound COC(=O)CCCCCO YDJZXHZRXDLCEH-UHFFFAOYSA-N 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052702 rhenium Inorganic materials 0.000 claims 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000004408 titanium dioxide Substances 0.000 claims 1
- 238000003809 water extraction Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09157503 | 2009-04-07 | ||
| EP09157503.5 | 2009-04-07 | ||
| PCT/EP2010/054285 WO2010115798A2 (de) | 2009-04-07 | 2010-03-31 | Verfahren zur herstellung von 1,6-hexandiol und caprolacton |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012522823A JP2012522823A (ja) | 2012-09-27 |
| JP2012522823A5 true JP2012522823A5 (enExample) | 2013-05-16 |
| JP5566450B2 JP5566450B2 (ja) | 2014-08-06 |
Family
ID=42667987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012503978A Expired - Fee Related JP5566450B2 (ja) | 2009-04-07 | 2010-03-31 | １，６−ヘキサンジオールおよびカプロラクトンの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8471042B2 (enExample) |
| EP (1) | EP2417089B1 (enExample) |
| JP (1) | JP5566450B2 (enExample) |
| KR (1) | KR20120004513A (enExample) |
| CN (1) | CN102388010B (enExample) |
| CA (1) | CA2755698A1 (enExample) |
| ES (1) | ES2421150T3 (enExample) |
| SG (1) | SG174394A1 (enExample) |
| WO (1) | WO2010115798A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120005018A (ko) * | 2009-04-07 | 2012-01-13 | 바스프 에스이 | 1,6-헥산디올을 제조하기 위한 방법 |
| DE102009047194A1 (de) | 2009-11-26 | 2011-06-01 | Basf Se | Verfahren zur Herstellung von Kunststoffen mit 1,6-Hexandiol mit einem Aldehydanteil von kleiner 500ppm |
| US8889922B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
| WO2013101970A1 (en) | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Production of 5-hydroxymethyl-2-furfural from levoglucosenone |
| US8865940B2 (en) | 2011-12-30 | 2014-10-21 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| EP2797868A4 (en) | 2011-12-30 | 2015-08-12 | Du Pont | PROCESS FOR PRODUCING HEXANEDIOLS |
| CN104136424A (zh) | 2011-12-30 | 2014-11-05 | 纳幕尔杜邦公司 | 由异山梨醇制备四氢呋喃-2,5-二甲醇 |
| US9018423B2 (en) | 2012-04-27 | 2015-04-28 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US8846985B2 (en) | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US8859826B2 (en) | 2012-04-27 | 2014-10-14 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| CN102671695B (zh) * | 2012-06-04 | 2014-10-08 | 湖南大学 | 一种六棱柱形貌的Co负载MFI分子筛及其制备方法 |
| KR102048986B1 (ko) * | 2018-03-22 | 2019-11-26 | 표상현 | ε-카프로락톤의 제조 방법 |
| CN111995612A (zh) * | 2020-08-24 | 2020-11-27 | 青岛科技大学 | 一种己内酯的合成方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235879B (de) | 1964-03-17 | 1967-03-09 | Basf Ag | Verfahren zur Herstellung von Alkoholen durch katalytische Hydrierung von Carbonsaeuren |
| DE1618143C3 (de) | 1967-04-27 | 1975-08-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung von epsilon-Hydroxycapronsäurelacton und von Alkandicarbonsäuren |
| JPS4815314B1 (enExample) * | 1969-08-18 | 1973-05-14 | ||
| DE2060548C3 (de) | 1970-12-09 | 1979-10-11 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von sehr reinem 1,6-Hexandiol durch Kristallisation |
| DE2321101C2 (de) | 1973-04-26 | 1982-07-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung im wesentlichen trägerfreier Kobaltkatalysatoren |
| US3933930A (en) * | 1975-03-06 | 1976-01-20 | Celanese Corporation | Hexanediol from cyclohexane |
| DE3823213A1 (de) | 1988-07-08 | 1990-01-11 | Basf Ag | Verfahren zur herstellung von caprolacton |
| MY118128A (en) * | 1996-03-01 | 2004-09-30 | Basf Ag | The preparation of 1, 6-hexanediol and caprolactone |
| DE19607954A1 (de) | 1996-03-01 | 1997-09-04 | Basf Ag | Verfahren zur Herstellung von 1,6-Hexandiol und Caprolacton |
| CN1092174C (zh) * | 1996-03-01 | 2002-10-09 | 巴斯福股份公司 | 纯度超过99%的1,6－己二醇的制备方法 |
| DE19730939A1 (de) | 1997-07-18 | 1999-01-21 | Basf Ag | Verfahren zur Hydrierung von Carbonylverbindungen |
| DE19738464A1 (de) | 1997-09-03 | 1999-03-04 | Basf Ag | Verwendung von Formkörpern als Katalysator zur Herstellung von Caprolactam |
| DE10128249A1 (de) * | 2001-06-11 | 2002-12-12 | Basf Ag | Verfahren zur Entfernung von Ameisensäure aus wässrigen Lösungen |
| DE10334489A1 (de) * | 2003-07-29 | 2005-02-24 | Basf Ag | Verfahren zur hydrierenden Zersetzung von Ammoniumformiaten in polyolhaltigen Reaktionsgemischen |
| DE102004033557A1 (de) | 2004-07-09 | 2006-02-16 | Basf Ag | Verfahren zur Herstellung von 1,6-Hexandiol in einer Reinheit von über 99,5% |
| DE102004054047A1 (de) | 2004-11-05 | 2006-05-11 | Basf Ag | Verfahren zur Herstellung von 1,6-Hexandiol |
| CN101679342A (zh) * | 2007-06-14 | 2010-03-24 | 巴斯夫欧洲公司 | 生产ε-己内酯的方法 |
| CN101848904B (zh) | 2007-11-05 | 2013-05-01 | 巴斯夫欧洲公司 | 生产ε-己内酯的方法 |
| EP2225220B1 (de) | 2007-12-21 | 2013-05-22 | Basf Se | Verfahren zur Herstellung von epsilon-Caprolacton |
| WO2009100989A2 (de) | 2008-02-15 | 2009-08-20 | Basf Se | Verfahren zur herstellung von 6-hydroxycapronsäureestern |
| DE102009047194A1 (de) | 2009-11-26 | 2011-06-01 | Basf Se | Verfahren zur Herstellung von Kunststoffen mit 1,6-Hexandiol mit einem Aldehydanteil von kleiner 500ppm |
-
2010
- 2010-03-31 EP EP10711899.4A patent/EP2417089B1/de not_active Not-in-force
- 2010-03-31 JP JP2012503978A patent/JP5566450B2/ja not_active Expired - Fee Related
- 2010-03-31 US US13/258,166 patent/US8471042B2/en not_active Expired - Fee Related
- 2010-03-31 CN CN201080015293.0A patent/CN102388010B/zh not_active Expired - Fee Related
- 2010-03-31 KR KR1020117026356A patent/KR20120004513A/ko not_active Abandoned
- 2010-03-31 CA CA2755698A patent/CA2755698A1/en not_active Abandoned
- 2010-03-31 ES ES10711899T patent/ES2421150T3/es active Active
- 2010-03-31 WO PCT/EP2010/054285 patent/WO2010115798A2/de not_active Ceased
- 2010-03-31 SG SG2011066404A patent/SG174394A1/en unknown
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