JP2011512339A5 - - Google Patents
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- Publication number
- JP2011512339A5 JP2011512339A5 JP2010546284A JP2010546284A JP2011512339A5 JP 2011512339 A5 JP2011512339 A5 JP 2011512339A5 JP 2010546284 A JP2010546284 A JP 2010546284A JP 2010546284 A JP2010546284 A JP 2010546284A JP 2011512339 A5 JP2011512339 A5 JP 2011512339A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- aqueous phase
- carboxylic acid
- hydroxycaproic
- cyclohexane
- 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
- 238000000034 method Methods 0.000 claims 8
- 239000008346 aqueous phase Substances 0.000 claims 7
- 150000001735 carboxylic acids Chemical class 0.000 claims 5
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 claims 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 4
- WHZIPJSAMHDEOG-UHFFFAOYSA-N 6-hydroperoxyhexanoic acid Chemical compound OOCCCCCC(O)=O WHZIPJSAMHDEOG-UHFFFAOYSA-N 0.000 claims 3
- -1 6-hydroxycaproic acid ester Chemical class 0.000 claims 3
- PNPPVRALIYXJBW-UHFFFAOYSA-N 6-oxohexanoic acid Chemical compound OC(=O)CCCCC=O PNPPVRALIYXJBW-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- 229910001882 dioxygen Inorganic materials 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 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
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000002244 precipitate Substances 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
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08101692 | 2008-02-15 | ||
| PCT/EP2009/051000 WO2009100989A2 (de) | 2008-02-15 | 2009-01-29 | Verfahren zur herstellung von 6-hydroxycapronsäureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011512339A JP2011512339A (ja) | 2011-04-21 |
| JP2011512339A5 true JP2011512339A5 (enExample) | 2012-03-15 |
Family
ID=40674192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010546284A Pending JP2011512339A (ja) | 2008-02-15 | 2009-01-29 | ６−ヒドロキシカプロン酸エステルの製造方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8183411B2 (enExample) |
| EP (1) | EP2244996B2 (enExample) |
| JP (1) | JP2011512339A (enExample) |
| KR (1) | KR20100127782A (enExample) |
| CN (1) | CN101945847B (enExample) |
| CA (1) | CA2714574A1 (enExample) |
| ES (1) | ES2393838T5 (enExample) |
| MY (1) | MY148679A (enExample) |
| WO (1) | WO2009100989A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010066674A2 (de) | 2008-12-09 | 2010-06-17 | Basf Se | Verfahren zur herstellung von polymethylolen |
| US8575401B2 (en) | 2008-12-09 | 2013-11-05 | Basf Se | Method for purifying crude polymethylols |
| EP2385933B1 (de) | 2009-01-12 | 2014-06-25 | Basf Se | Verfahren zur herstellung von polymethylolen |
| CA2755698A1 (en) | 2009-04-07 | 2010-10-14 | Basf Se | Method for producing 1,6-hexanediol and caprolactone |
| JP5586686B2 (ja) | 2009-04-07 | 2014-09-10 | ビーエーエスエフ ソシエタス・ヨーロピア | １，６−ヘキサンジオールの製造方法 |
| CN102452919B (zh) * | 2010-10-27 | 2014-10-01 | 中国石油化工股份有限公司 | 一种内酯催化氧化制备相应羟基酸的方法 |
| PL227792B1 (pl) * | 2012-03-23 | 2018-01-31 | Korzeniowski Waclaw Chemenergia | Sposób otrzymywania estrów syntetycznych |
| JP6274573B2 (ja) * | 2014-06-04 | 2018-02-07 | 宇部興産株式会社 | カルボン酸並びにケトン及び／又はアルコールの製造方法 |
| CN114845983B (zh) * | 2019-12-18 | 2025-12-05 | 巴斯夫欧洲公司 | 制备环己醇和环己酮的方法 |
| CN111892501A (zh) * | 2020-07-15 | 2020-11-06 | 江西盛伟科技股份有限公司 | 一种6-羟基己酸甲酯的制备方法 |
| CN112010753A (zh) * | 2020-08-18 | 2020-12-01 | 青岛科技大学 | 一种6-羟基己酸酯的制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1210785B (de) * | 1963-11-27 | 1966-02-17 | Basf Ag | Verfahren zur Gewinnung von epsilon-Hydroxycapron-saeure |
| FR1505363A (fr) | 1966-04-20 | 1967-12-15 | Rhone Poulenc Sa | Perfectionnement à la préparation des cycloalcanols et des mélanges cycloalcanols/cycloalcanones |
| FR1585375A (enExample) | 1968-10-11 | 1970-01-16 | ||
| US3772375A (en) * | 1968-10-11 | 1973-11-13 | Rhone Poulenc Sa | Process for producing epsilon-hydroxycaproic acid |
| JPS4815314B1 (enExample) * | 1969-08-18 | 1973-05-14 | ||
| US3848003A (en) * | 1970-06-26 | 1974-11-12 | Celanese Corp | Hydrogenolysis of carboxylic acids with cobalt catalysts |
| US3752861A (en) * | 1970-08-17 | 1973-08-14 | Celanese Corp | Production of hydroxy compounds by hydrogenolysis of buffered carboxylate salts |
| CA1049041A (en) | 1972-11-23 | 1979-02-20 | Stamicarbon B.V. | Process for the preparation of cycloalkanones and/or cycloalkanols |
| US3933930A (en) | 1975-03-06 | 1976-01-20 | Celanese Corporation | Hexanediol from cyclohexane |
| DE3823695A1 (de) | 1988-07-13 | 1990-01-18 | Basf Ag | Verfahren zur herstellung von 6-hydroxycapronsaeureestern |
| 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 |
| DE19738464A1 (de) | 1997-09-03 | 1999-03-04 | Basf Ag | Verwendung von Formkörpern als Katalysator zur Herstellung von Caprolactam |
| DE19750532A1 (de) * | 1997-11-14 | 1999-05-20 | Basf Ag | Verfahren zur Herstellung von 1,6-Hexandiol und 6-Hydroxycapronsäure bzw. deren Estern |
| US6063958A (en) * | 1998-12-22 | 2000-05-16 | China Petrochemical Development Corporation | Method of recovering adipic acid and 6-hydroxycaproic acid from waste solution of alkali metal salts of organic acids coming from the process of cyclohexane oxidation |
| FR2846652B1 (fr) | 2002-10-30 | 2006-09-22 | Rhodia Polyamide Intermediates | Procede de fabrication d'acides carboxyliques |
| 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 |
-
2009
- 2009-01-29 MY MYPI2010003736A patent/MY148679A/en unknown
- 2009-01-29 CA CA2714574A patent/CA2714574A1/en not_active Abandoned
- 2009-01-29 EP EP09709624.2A patent/EP2244996B2/de not_active Not-in-force
- 2009-01-29 CN CN2009801053107A patent/CN101945847B/zh not_active Expired - Fee Related
- 2009-01-29 WO PCT/EP2009/051000 patent/WO2009100989A2/de not_active Ceased
- 2009-01-29 ES ES09709624.2T patent/ES2393838T5/es active Active
- 2009-01-29 US US12/867,509 patent/US8183411B2/en not_active Expired - Fee Related
- 2009-01-29 KR KR1020107020520A patent/KR20100127782A/ko not_active Ceased
- 2009-01-29 JP JP2010546284A patent/JP2011512339A/ja active Pending
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