JP2012512230A5 - - Google Patents
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- Publication number
- JP2012512230A5 JP2012512230A5 JP2011541390A JP2011541390A JP2012512230A5 JP 2012512230 A5 JP2012512230 A5 JP 2012512230A5 JP 2011541390 A JP2011541390 A JP 2011541390A JP 2011541390 A JP2011541390 A JP 2011541390A JP 2012512230 A5 JP2012512230 A5 JP 2012512230A5
- Authority
- JP
- Japan
- Prior art keywords
- water
- ester
- process according
- pressure
- acid
- 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 description 17
- 238000005886 esterification reaction Methods 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 9
- -1 aliphatic monocarboxylic acid Chemical class 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000013522 chelant Chemical class 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- 238000012805 post-processing Methods 0.000 claims 1
- 230000003068 static effect Effects 0.000 claims 1
- 229910052845 zircon Inorganic materials 0.000 description 8
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 7
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 6
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical group [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- QUVMSYUGOKEMPX-UHFFFAOYSA-N 2-methylpropan-1-olate;titanium(4+) Chemical compound [Ti+4].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-] QUVMSYUGOKEMPX-UHFFFAOYSA-N 0.000 description 1
- DEVXQDKRGJCZMV-UHFFFAOYSA-K Aluminum acetoacetate Chemical compound [Al+3].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O.CC(=O)CC([O-])=O DEVXQDKRGJCZMV-UHFFFAOYSA-K 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- PBZJABRHZRYANY-UHFFFAOYSA-K aluminum;2-methylpropanoate Chemical compound [Al+3].CC(C)C([O-])=O.CC(C)C([O-])=O.CC(C)C([O-])=O PBZJABRHZRYANY-UHFFFAOYSA-K 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical group [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical group [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08171800 | 2008-12-16 | ||
| EP08171800.9 | 2008-12-16 | ||
| PCT/EP2009/067178 WO2010076193A1 (de) | 2008-12-16 | 2009-12-15 | Verfahren zur aufarbeitung eines rohen esters |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012512230A JP2012512230A (ja) | 2012-05-31 |
| JP2012512230A5 true JP2012512230A5 (https=) | 2013-12-26 |
| JP5559193B2 JP5559193B2 (ja) | 2014-07-23 |
Family
ID=42167495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011541390A Expired - Fee Related JP5559193B2 (ja) | 2008-12-16 | 2009-12-15 | 粗製エステルの後処理法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8729292B2 (https=) |
| EP (1) | EP2379483B1 (https=) |
| JP (1) | JP5559193B2 (https=) |
| KR (1) | KR101346396B1 (https=) |
| CN (1) | CN102256925B (https=) |
| CA (1) | CA2744130C (https=) |
| ES (1) | ES2422262T3 (https=) |
| MY (1) | MY156371A (https=) |
| WO (1) | WO2010076193A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010048311A1 (de) | 2010-10-14 | 2012-04-19 | Continental Automotive Gmbh | Verfahren und Vorrichtung zum Betreiben einer Brennkraftmaschine |
| CN102351692B (zh) * | 2011-10-10 | 2013-08-21 | 山东天兴生物科技有限公司 | 癸二酸二甲酯的制备方法 |
| DE102013015289A1 (de) * | 2013-09-14 | 2015-03-19 | Oxea Gmbh | Verfahren zur Nachbehandlung von Polyolestern |
| BR112017001912A2 (pt) * | 2014-08-01 | 2017-11-28 | Basf Se | ?processo para elaboração de um éster em bruto? |
| CN107074720B (zh) | 2014-09-24 | 2021-01-08 | 巴斯夫欧洲公司 | 以反应混合物的循环制备对苯二甲酸二酯的方法 |
| EP3197860A1 (de) | 2014-09-24 | 2017-08-02 | Basf Se | Verfahren zur herstellung von terephthalsäurediestern mit rückalkohol-anreicherung |
| MX2017003927A (es) | 2014-09-24 | 2017-06-30 | Basf Se | Proceso para producir diesteres de acido tereftalico. |
| MX2017003920A (es) | 2014-09-24 | 2017-06-28 | Basf Se | Metodo para producir diesteres de acido tereftalico con deshidratacion de alcohol recirculado. |
| CN107540621B (zh) * | 2017-09-27 | 2020-07-31 | 山西北化关铝化工有限公司 | 奥克托今合成产品抽滤效率提高的方法 |
| KR102528326B1 (ko) * | 2020-02-14 | 2023-05-02 | 한화솔루션 주식회사 | 에스테르계 화합물의 제조방법 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1945359B2 (de) | 1969-09-08 | 1973-05-10 | Verfahren zur gewinnung von estern | |
| DE2330435C3 (de) | 1973-06-15 | 1978-08-17 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Aufarbeitung von rohen Estern |
| DE4002949A1 (de) | 1990-02-01 | 1991-08-08 | Rwe Dea Ag | Verfahren zur aufarbeitung von rohem veresterungsgemisch |
| DE19721347B9 (de) * | 1997-05-22 | 2005-09-29 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Esterweichmachern |
| DE10043545A1 (de) * | 2000-09-05 | 2002-03-14 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Carbonsäureestern |
| DE10149350A1 (de) | 2001-10-06 | 2003-04-17 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Carbonsäureestern |
| DE10236279A1 (de) * | 2002-08-08 | 2004-02-19 | Basf Ag | Verfahren zur Abtrennung von Veresterungskatalysator |
| US7919649B2 (en) * | 2005-05-27 | 2011-04-05 | Exxonmobile Chemical Patents Inc. | Plasticiser esters |
| US7291748B2 (en) * | 2005-07-28 | 2007-11-06 | Basf Corporation | C10/C7 ester mixtures based on 2-propylheptanol |
-
2009
- 2009-12-15 KR KR1020117016489A patent/KR101346396B1/ko not_active Expired - Fee Related
- 2009-12-15 CA CA2744130A patent/CA2744130C/en active Active
- 2009-12-15 CN CN200980150535.4A patent/CN102256925B/zh not_active Expired - Fee Related
- 2009-12-15 WO PCT/EP2009/067178 patent/WO2010076193A1/de not_active Ceased
- 2009-12-15 MY MYPI2011002710A patent/MY156371A/en unknown
- 2009-12-15 US US13/140,239 patent/US8729292B2/en active Active
- 2009-12-15 JP JP2011541390A patent/JP5559193B2/ja not_active Expired - Fee Related
- 2009-12-15 EP EP09768101.9A patent/EP2379483B1/de active Active
- 2009-12-15 ES ES09768101T patent/ES2422262T3/es active Active
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