JP2013537882A5 - - Google Patents
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- Publication number
- JP2013537882A5 JP2013537882A5 JP2013527563A JP2013527563A JP2013537882A5 JP 2013537882 A5 JP2013537882 A5 JP 2013537882A5 JP 2013527563 A JP2013527563 A JP 2013527563A JP 2013527563 A JP2013527563 A JP 2013527563A JP 2013537882 A5 JP2013537882 A5 JP 2013537882A5
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- esterification
- mixture
- hydrogenation
- distillation
- 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 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 14
- 230000032050 esterification Effects 0.000 claims 9
- 238000005886 esterification reaction Methods 0.000 claims 9
- 238000005984 hydrogenation reaction Methods 0.000 claims 9
- 238000004821 distillation Methods 0.000 claims 7
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims 6
- 238000009835 boiling Methods 0.000 claims 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 238000005809 transesterification reaction Methods 0.000 claims 3
- -1 6-hydroxycaproic acid ester Chemical class 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 239000000463 material Substances 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
- 238000007363 ring formation reaction Methods 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims 1
- 239000005751 Copper oxide Substances 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000004568 cement Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910000431 copper oxide Inorganic materials 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 229910052746 lanthanum Inorganic materials 0.000 claims 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000007493 shaping process Methods 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 239000010937 tungsten Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10175795.3 | 2010-09-08 | ||
| EP10175795 | 2010-09-08 | ||
| PCT/EP2011/065276 WO2012032002A2 (de) | 2010-09-08 | 2011-09-05 | VERFAHREN ZUR HERSTELLUNG VON ε-CAPROLACTON UND 1,6-HEXANDIOL |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013537882A JP2013537882A (ja) | 2013-10-07 |
| JP2013537882A5 true JP2013537882A5 (enExample) | 2014-10-23 |
| JP5855106B2 JP5855106B2 (ja) | 2016-02-09 |
Family
ID=44534445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013527563A Expired - Fee Related JP5855106B2 (ja) | 2010-09-08 | 2011-09-05 | ε−カプロラクトン及び１，６−ヘキサンジオールの製造法 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP2614056B1 (enExample) |
| JP (1) | JP5855106B2 (enExample) |
| CN (1) | CN103080098B (enExample) |
| ES (1) | ES2506465T3 (enExample) |
| RU (1) | RU2571082C2 (enExample) |
| SG (1) | SG187942A1 (enExample) |
| TW (1) | TWI496764B (enExample) |
| WO (2) | WO2012038848A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2598616B2 (ja) | 1994-09-05 | 1997-04-09 | 晃立工業株式会社 | 流紋岩質溶結凝灰岩を破砕してなる細骨材及びその製造方法 |
| CL2013003356A1 (es) | 2013-11-22 | 2014-08-08 | Univ Pontificia Catolica Chile | Mutantes del gen que codifica la enzina fenilacetona monooxigenasa (pamo) aislada de termofibida fusca o thermononospora fusca con sustitucines en las posiciones 93,94,y 440 (n,d y f, respectivamente) y combinaciones especificas de las posiciones 441,442,443 y/o 444(g o d,p o e,t,v,i o w y q respectivamente ) con alto rendimiento como catalizadores en la conversion de ciclohexanona a epailon-caprolactona y alta estabilidad termica , adn condificante y secuencias amino acidicas codificadas. |
| GB202109710D0 (en) | 2021-07-05 | 2021-08-18 | Johnson Matthey Davy Technologies Ltd | Separation process for the production of C5 or C6 alkanediol |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3524892A (en) | 1962-11-16 | 1970-08-18 | Celanese Corp | Hexanediol from cyclohexane |
| DE1618143C3 (de) | 1967-04-27 | 1975-08-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung von epsilon-Hydroxycapronsäurelacton und von Alkandicarbonsäuren |
| US3597330A (en) * | 1967-04-27 | 1971-08-03 | Basf Ag | Recovery of epsilon-caprolactone and alkane dicarboxylic acid by acid treatment and vacuum distillation |
| FR1585375A (enExample) | 1968-10-11 | 1970-01-16 | ||
| US3624258A (en) * | 1969-03-22 | 1971-11-30 | Teijin Ltd | Process for the preparation of {68 -caprolactone |
| DE3823213A1 (de) * | 1988-07-08 | 1990-01-11 | Basf Ag | Verfahren zur herstellung von caprolacton |
| DE4141199A1 (de) | 1991-12-13 | 1993-06-17 | Sued Chemie Ag | Chromfreier katalysator fuer die hydrierung von organischen verbindungen, die die carbonylfunktionen enthalten |
| DE19607954A1 (de) | 1996-03-01 | 1997-09-04 | Basf Ag | Verfahren zur Herstellung von 1,6-Hexandiol und Caprolacton |
| MY118128A (en) * | 1996-03-01 | 2004-09-30 | Basf Ag | The preparation of 1, 6-hexanediol and caprolactone |
| FR2757154B1 (fr) | 1996-12-12 | 2000-01-14 | Rhone Poulenc Fibres | Procede de preparation de diacides a partir des eaux de lavage des produits d'oxydation du cyclohexane |
| DE19750532A1 (de) * | 1997-11-14 | 1999-05-20 | Basf Ag | Verfahren zur Herstellung von 1,6-Hexandiol und 6-Hydroxycapronsäure bzw. deren Estern |
| GB9724480D0 (en) * | 1997-11-19 | 1998-01-14 | Hexagen Technology Limited | Screening process |
| DE10313702A1 (de) | 2003-03-27 | 2004-10-07 | Basf Ag | Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen |
| DE102004033556A1 (de) | 2004-07-09 | 2006-02-16 | Basf Ag | Katalysatorformkörper und Verfahren zur Hydrierung von Carbonylverbindungen |
| DE102005032726A1 (de) | 2005-07-13 | 2007-01-18 | Basf Ag | Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen |
| WO2008152001A1 (de) * | 2007-06-14 | 2008-12-18 | Basf Se | VERFAHREN ZUR HERSTELLUNG ε-CAPROLACTON |
| US8247580B2 (en) * | 2007-11-05 | 2012-08-21 | Basf Se | Process for preparing ε-caprolactone |
-
2011
- 2011-09-05 EP EP11749864.2A patent/EP2614056B1/de not_active Not-in-force
- 2011-09-05 WO PCT/IB2011/053872 patent/WO2012038848A1/en not_active Ceased
- 2011-09-05 ES ES11749864.2T patent/ES2506465T3/es active Active
- 2011-09-05 JP JP2013527563A patent/JP5855106B2/ja not_active Expired - Fee Related
- 2011-09-05 WO PCT/EP2011/065276 patent/WO2012032002A2/de not_active Ceased
- 2011-09-05 RU RU2013115238/04A patent/RU2571082C2/ru not_active IP Right Cessation
- 2011-09-05 SG SG2013013487A patent/SG187942A1/en unknown
- 2011-09-05 CN CN201180041480.0A patent/CN103080098B/zh not_active Expired - Fee Related
- 2011-09-07 TW TW100132321A patent/TWI496764B/zh not_active IP Right Cessation
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