JP2012522819A5 - - Google Patents
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- Publication number
- JP2012522819A5 JP2012522819A5 JP2012503955A JP2012503955A JP2012522819A5 JP 2012522819 A5 JP2012522819 A5 JP 2012522819A5 JP 2012503955 A JP2012503955 A JP 2012503955A JP 2012503955 A JP2012503955 A JP 2012503955A JP 2012522819 A5 JP2012522819 A5 JP 2012522819A5
- Authority
- JP
- Japan
- Prior art keywords
- esterification
- carboxylic acid
- cyclohexanediol
- acid
- hydrogenation
- 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 12
- 238000004821 distillation Methods 0.000 claims 9
- 230000032050 esterification Effects 0.000 claims 7
- 238000005886 esterification reaction Methods 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 6
- 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 6
- 238000005984 hydrogenation reaction Methods 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-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
- 239000000047 product Substances 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- 150000001735 carboxylic acids Chemical class 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- -1 carboxylic acid methyl ester Chemical class 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
- 150000002148 esters Chemical class 0.000 claims 2
- 235000019253 formic acid Nutrition 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
- 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
- PNPPVRALIYXJBW-UHFFFAOYSA-N 6-oxohexanoic acid Chemical compound OC(=O)CCCCC=O PNPPVRALIYXJBW-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001299 aldehydes Chemical class 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
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 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
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 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 |
|---|---|---|---|
| EP09157511 | 2009-04-07 | ||
| EP09157511.8 | 2009-04-07 | ||
| PCT/EP2010/054053 WO2010115738A1 (de) | 2009-04-07 | 2010-03-29 | Verfahren zur herstellung von 1,6-hexandiol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012522819A JP2012522819A (ja) | 2012-09-27 |
| JP2012522819A5 true JP2012522819A5 (enExample) | 2013-05-16 |
| JP5586686B2 JP5586686B2 (ja) | 2014-09-10 |
Family
ID=42668286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012503955A Expired - Fee Related JP5586686B2 (ja) | 2009-04-07 | 2010-03-29 | １，６−ヘキサンジオールの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8629306B2 (enExample) |
| EP (1) | EP2417088B1 (enExample) |
| JP (1) | JP5586686B2 (enExample) |
| KR (1) | KR20120005018A (enExample) |
| CN (1) | CN102388009B (enExample) |
| CA (1) | CA2755696A1 (enExample) |
| ES (1) | ES2415156T3 (enExample) |
| SG (1) | SG174392A1 (enExample) |
| WO (1) | WO2010115738A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009047193A1 (de) | 2009-11-26 | 2011-06-01 | Basf Se | Verfahren zur Herstellung von Diolen durch Hydrierung eines Carbonsäure enthaltenden Gemisches mittels Kobalt enthaltenden Katalysatoren |
| 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 |
| US8865940B2 (en) | 2011-12-30 | 2014-10-21 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8962894B2 (en) | 2011-12-30 | 2015-02-24 | E I Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
| US8884036B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of hydroxymethylfurfural from levoglucosenone |
| CN104024197A (zh) | 2011-12-30 | 2014-09-03 | 纳幕尔杜邦公司 | 己二醇的制备方法 |
| BR112014015994A2 (pt) | 2011-12-30 | 2018-05-22 | Du Pont | processo. |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8846985B2 (en) | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US9018423B2 (en) | 2012-04-27 | 2015-04-28 | 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 |
| CN105727962B (zh) * | 2016-02-02 | 2018-07-31 | 上海华峰新材料研发科技有限公司 | 用于己二酸二甲酯制己二醇的催化剂及其制备方法和应用 |
| JP7598083B1 (ja) * | 2023-04-13 | 2024-12-11 | Dic株式会社 | ヘキサメチレン（メタ）アクリレート組成物、活性エネルギー線硬化型樹脂組成物、硬化物 |
Family Cites Families (22)
| 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 |
| 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 |
| 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 |
| US6008418A (en) * | 1996-03-01 | 1999-12-28 | Basf Aktiengesellschaft | Process for preparing 1,6 hexanediol with a level of purity over 99% |
| 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 |
| DE10313702A1 (de) | 2003-03-27 | 2004-10-07 | Basf Ag | Katalysator und Verfahren zur Hydrierung von Carbonylverbindungen |
| 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 |
| 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 |
| KR20100110830A (ko) | 2007-12-21 | 2010-10-13 | 바스프 에스이 | ε-카프로락톤의 제조 방법 |
| MY148679A (en) | 2008-02-15 | 2013-05-31 | Basf Se | Process for preparing 6-hydroxycaproic esters |
| CA2755698A1 (en) * | 2009-04-07 | 2010-10-14 | Basf Se | Method for producing 1,6-hexanediol and caprolactone |
| DE102009047193A1 (de) | 2009-11-26 | 2011-06-01 | Basf Se | Verfahren zur Herstellung von Diolen durch Hydrierung eines Carbonsäure enthaltenden Gemisches mittels Kobalt enthaltenden Katalysatoren |
| 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
- 2010-03-29 JP JP2012503955A patent/JP5586686B2/ja not_active Expired - Fee Related
- 2010-03-29 WO PCT/EP2010/054053 patent/WO2010115738A1/de not_active Ceased
- 2010-03-29 US US13/257,496 patent/US8629306B2/en not_active Expired - Fee Related
- 2010-03-29 ES ES10711879T patent/ES2415156T3/es active Active
- 2010-03-29 SG SG2011066388A patent/SG174392A1/en unknown
- 2010-03-29 KR KR1020117026357A patent/KR20120005018A/ko not_active Abandoned
- 2010-03-29 CA CA2755696A patent/CA2755696A1/en not_active Abandoned
- 2010-03-29 CN CN201080015253.6A patent/CN102388009B/zh not_active Expired - Fee Related
- 2010-03-29 EP EP10711879.6A patent/EP2417088B1/de not_active Not-in-force
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