ES2554518T3 - Método para la producción de ésteres de ácido carboxílico - Google Patents
Método para la producción de ésteres de ácido carboxílico Download PDFInfo
- Publication number
- ES2554518T3 ES2554518T3 ES09795970.4T ES09795970T ES2554518T3 ES 2554518 T3 ES2554518 T3 ES 2554518T3 ES 09795970 T ES09795970 T ES 09795970T ES 2554518 T3 ES2554518 T3 ES 2554518T3
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- Prior art keywords
- alcohol
- organic phase
- reintroduced
- partially
- boiling points
- Prior art date
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 61
- 238000009835 boiling Methods 0.000 claims abstract description 47
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- 239000000203 mixture Substances 0.000 claims abstract description 25
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- 150000001875 compounds Chemical class 0.000 claims abstract description 15
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
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- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
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- 150000007517 lewis acids Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- FDSIFWDGJSJXMP-UHFFFAOYSA-N methyl 3-methyl-5-(5-methyl-1,2-oxazol-3-yl)-1,2-oxazole-4-carboxylate Chemical compound CC1=NOC(C2=NOC(C)=C2)=C1C(=O)OC FDSIFWDGJSJXMP-UHFFFAOYSA-N 0.000 description 1
- SAOSCTYRONNFTC-UHFFFAOYSA-N methyl-capric acid Natural products CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-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
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 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
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- JINJMFAIGCWUDW-UHFFFAOYSA-L zirconium(2+);diacetate Chemical compound [Zr+2].CC([O-])=O.CC([O-])=O JINJMFAIGCWUDW-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08171796 | 2008-12-16 | ||
| EP08171796 | 2008-12-16 | ||
| PCT/EP2009/067177 WO2010076192A1 (de) | 2008-12-16 | 2009-12-15 | Verfahren zur herstellung von carbonsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2554518T3 true ES2554518T3 (es) | 2015-12-21 |
Family
ID=42167505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09795970.4T Active ES2554518T3 (es) | 2008-12-16 | 2009-12-15 | Método para la producción de ésteres de ácido carboxílico |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8901343B2 (enExample) |
| EP (1) | EP2379481B1 (enExample) |
| JP (1) | JP5780967B2 (enExample) |
| KR (1) | KR101757936B1 (enExample) |
| CN (1) | CN102256923B (enExample) |
| CA (1) | CA2746599A1 (enExample) |
| ES (1) | ES2554518T3 (enExample) |
| MY (1) | MY158588A (enExample) |
| WO (1) | WO2010076192A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101967098A (zh) * | 2010-09-26 | 2011-02-09 | 昆山合峰化工有限公司 | 邻苯二甲酸二(2-丙基庚)酯的制备方法 |
| CN102001948B (zh) * | 2010-10-18 | 2015-04-15 | 华侨大学 | 一种酯化合成对苯二甲酸二异辛酯的方法 |
| DE102011006557A1 (de) * | 2011-03-31 | 2012-10-04 | Evonik Oxeno Gmbh | Gemisch von Bersteinsäureestern |
| JP6694713B2 (ja) | 2012-12-11 | 2020-05-20 | ブラッコ・イメージング・ソシエタ・ペル・アチオニＢｒａｃｃｏ Ｉｍａｇｉｎｇ Ｓ．Ｐ．Ａ． | （ｓ）−２−アセチルオキシプロピオン酸クロリドの連続製造方法 |
| US20150014148A1 (en) * | 2013-07-11 | 2015-01-15 | Celanese Acetate Llc | Process for Energy Recovery in Manufacturing Cellulose Esters |
| CN104418747B (zh) * | 2013-08-22 | 2016-08-10 | 中国科学院大连化学物理研究所 | 一种制备邻苯二甲酸二（2-丙基庚）酯的方法 |
| TWI654177B (zh) * | 2013-10-31 | 2019-03-21 | 德商巴斯夫歐洲公司 | 製備羧酸酯的方法及其作爲塑化劑的用途 |
| RU2016145450A (ru) * | 2014-04-22 | 2018-05-22 | Басф Се | Способ получения сложных эфиров карбоновых кислот в присутствии ионной жидкости и кислотного катализатора этерификации и их применение в качестве пластификатора |
| US9963416B2 (en) * | 2014-06-10 | 2018-05-08 | Bracco Imaging S.P.A. | Method for the preparation of (S)-2-acetyloxypropionic acid and derivatives thereof |
| EP3160930B1 (en) | 2014-06-24 | 2018-10-31 | Dow Global Technologies LLC | Process for producing low voc glycol ether esters |
| WO2015200088A1 (en) | 2014-06-24 | 2015-12-30 | Dow Global Technologies Llc | Process for producing low voc coalescing aids |
| TWI686444B (zh) | 2014-09-04 | 2020-03-01 | 德商巴斯夫歐洲公司 | 包含聚合二羧酸酯的塑化劑組成物 |
| WO2016046120A1 (de) * | 2014-09-24 | 2016-03-31 | Basf Se | Verfahren zur herstellung von terephthalsäurediestern mit rückalkohol-anreicherung |
| TR201904928T4 (tr) | 2014-09-24 | 2019-05-21 | Basf Se | Tereftalik asit diesterlerin resirküle alkol dehidratasyonu ile üretimi için yöntem. |
| US10239818B2 (en) | 2014-09-24 | 2019-03-26 | Basf Se | Method for producing diesters of terephthalic acid with circulation of the reaction mixture |
| RU2648983C1 (ru) * | 2014-09-24 | 2018-03-29 | Басф Се | Способ получения сложных диэфиров терефталевой кислоты |
| KR102138788B1 (ko) * | 2017-09-07 | 2020-07-28 | 주식회사 엘지화학 | 에스터 조성물의 제조 시스템 및 이를 이용한 에스터 조성물의 제조 방법 |
| WO2019185409A1 (de) | 2018-03-29 | 2019-10-03 | Basf Se | Pvc-zusammensetzung, enthaltend wenigstens einen weichmacher der wenigstens eine carbonsäureestergruppe aufweist und wenigstens eine carbodiimidverbindung |
| WO2020173818A1 (de) | 2019-02-25 | 2020-09-03 | Basf Se | Verfahren zur aufarbeitung von benzolpolycarbonsäureestern und deren verwendung zur herstellung von cyclohexanpolycarbonsäureestern |
| EP3854779B1 (en) * | 2019-04-04 | 2023-08-23 | LG Chem, Ltd. | Continuous refining method for esterification reaction products |
| US11512166B2 (en) | 2019-04-04 | 2022-11-29 | Lg Chem, Ltd. | Method and system for manufacturing ester-based composition |
| CN112955424A (zh) * | 2019-04-04 | 2021-06-11 | 株式会社Lg化学 | 酯类组合物的制备方法和制备系统 |
| EP3854774B1 (en) * | 2019-04-04 | 2024-03-20 | LG Chem, Ltd. | Method for preparing ester-based composition |
| CN112955425B (zh) * | 2019-04-04 | 2023-12-26 | 株式会社Lg化学 | 酯类组合物的制备方法和制备系统 |
| KR102489171B1 (ko) * | 2019-07-04 | 2023-01-18 | 주식회사 엘지화학 | 디에스터계 물질의 제조 유닛 및 이를 포함하는 디에스터계 물질의 제조 시스템 |
| KR102488351B1 (ko) * | 2019-07-04 | 2023-01-13 | 주식회사 엘지화학 | 디에스터계 물질의 연속식 제조방법 |
| KR102489173B1 (ko) * | 2019-07-04 | 2023-01-18 | 주식회사 엘지화학 | 열교환 시스템 및 이를 포함하는 디에스터계 조성물 제조 시스템 |
| KR102489174B1 (ko) * | 2019-07-04 | 2023-01-18 | 주식회사 엘지화학 | 디에스터계 조성물의 제조 시스템 및 방법 |
| KR102489172B1 (ko) * | 2019-07-04 | 2023-01-18 | 주식회사 엘지화학 | 디에스터계 물질의 제조 유닛 및 이를 포함하는 디에스터계 물질의 제조 시스템 |
| CN112239405B (zh) * | 2019-07-17 | 2023-05-02 | 中国石油化工股份有限公司 | 2,6-萘二甲酸二甲酯的合成方法 |
| KR102501597B1 (ko) * | 2019-09-25 | 2023-02-20 | 주식회사 엘지화학 | 디에스테르계 조성물의 제조 시스템 및 제조방법 |
| KR102595882B1 (ko) * | 2019-09-25 | 2023-10-30 | 주식회사 엘지화학 | 디에스터계 조성물의 제조 시스템 및 제조방법 |
| KR102819374B1 (ko) * | 2020-08-13 | 2025-06-11 | 주식회사 엘지화학 | 에스터의 제조방법 |
| EP4219442B1 (en) * | 2020-09-24 | 2025-06-04 | Lg Chem, Ltd. | Method for producing ester-based composition |
| KR102390132B1 (ko) * | 2020-09-24 | 2022-04-25 | 주식회사 엘지화학 | 에스터계 조성물의 제조방법 |
| KR102393901B1 (ko) * | 2020-09-24 | 2022-05-04 | 주식회사 엘지화학 | 에스터계 물질의 회분식 제조방법 |
| CN116137860A (zh) * | 2020-09-24 | 2023-05-19 | 株式会社Lg化学 | 酯类组合物的制备方法 |
| KR102797134B1 (ko) | 2020-11-17 | 2025-04-21 | 주식회사 엘지화학 | 디에스터계 화합물의 제조방법 |
| KR102797150B1 (ko) * | 2020-11-17 | 2025-04-21 | 주식회사 엘지화학 | 디에스터계 물질의 제조방법 |
| KR20220067352A (ko) * | 2020-11-17 | 2022-05-24 | 주식회사 엘지화학 | 디에스터계 물질의 제조방법 |
| KR102797136B1 (ko) * | 2020-11-17 | 2025-04-18 | 주식회사 엘지화학 | 디에스터계 화합물의 제조방법 |
| CN112439216A (zh) * | 2020-12-14 | 2021-03-05 | 河南久圣化工有限公司 | 一种从己二酸废液中回收二元羧酸的三级蒸发系统 |
| CN119657021A (zh) * | 2024-12-18 | 2025-03-21 | 中国石油化工股份有限公司 | 一种撬装式邻苯二甲酸二异壬酯合成装置及合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2648711A (en) * | 1949-07-19 | 1953-08-11 | Standard Oil Dev Co | Recovery of alcohols from direct hydration of olefins |
| DE1921110A1 (de) | 1969-04-25 | 1970-11-26 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Dicarbonsaeuredialkylestern |
| IN171820B (enExample) * | 1989-12-22 | 1993-01-16 | Lever Hindustan Ltd | |
| GB9102513D0 (en) | 1991-02-06 | 1991-03-27 | Exxon Chemical Patents Inc | Hydrocarbon production |
| DE4339713A1 (de) | 1993-11-22 | 1995-05-24 | Basf Ag | Verfahren zur Oligomerisierung von Olefinen zu hochlinearen Oligomeren und Katalysatoren dafür |
| CN100347146C (zh) * | 1999-06-17 | 2007-11-07 | 联合碳化化学及塑料技术公司 | 进行平衡限制反应的方法 |
| DE19955593A1 (de) | 1999-11-18 | 2001-05-23 | Basf Ag | C13-Alkoholgemisch und funktionalisiertes C13-Alkoholgemisch |
| DE10007213A1 (de) | 2000-02-17 | 2001-08-23 | Basf Ag | Verfahren zur Herstellung von Estern alpha,beta-ungesättigter Carbonsäuren |
| US6271410B1 (en) * | 2000-06-06 | 2001-08-07 | Creanova Inc. | Higher alkyl esters of cyanoacetic acid |
| 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 |
| TWI324592B (en) * | 2002-11-28 | 2010-05-11 | Sulzer Chemtech Ag | A method for the esterification of a fatty acid |
| US20040192957A1 (en) * | 2003-03-31 | 2004-09-30 | Wickens Danita Inez | Method of recovering 2-ethylhexyl alcohol from a mixture comprising 2-ethylhexyl acrylate |
| JP2007153814A (ja) | 2005-12-06 | 2007-06-21 | Mitsubishi Chemicals Corp | ジカルボン酸ジエステルの製造方法 |
-
2009
- 2009-12-15 JP JP2011541389A patent/JP5780967B2/ja not_active Expired - Fee Related
- 2009-12-15 MY MYPI2011002711A patent/MY158588A/en unknown
- 2009-12-15 CN CN2009801506516A patent/CN102256923B/zh not_active Expired - Fee Related
- 2009-12-15 CA CA2746599A patent/CA2746599A1/en active Pending
- 2009-12-15 ES ES09795970.4T patent/ES2554518T3/es active Active
- 2009-12-15 EP EP09795970.4A patent/EP2379481B1/de not_active Revoked
- 2009-12-15 KR KR1020117016501A patent/KR101757936B1/ko not_active Expired - Fee Related
- 2009-12-15 WO PCT/EP2009/067177 patent/WO2010076192A1/de not_active Ceased
- 2009-12-15 US US13/140,256 patent/US8901343B2/en not_active Expired - Fee Related
-
2014
- 2014-11-11 US US14/538,060 patent/US9260373B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20150141691A1 (en) | 2015-05-21 |
| CA2746599A1 (en) | 2010-07-08 |
| US20110251420A1 (en) | 2011-10-13 |
| MY158588A (en) | 2016-10-31 |
| CN102256923B (zh) | 2013-12-04 |
| JP5780967B2 (ja) | 2015-09-16 |
| KR101757936B1 (ko) | 2017-07-13 |
| CN102256923A (zh) | 2011-11-23 |
| US9260373B2 (en) | 2016-02-16 |
| WO2010076192A1 (de) | 2010-07-08 |
| EP2379481B1 (de) | 2015-08-26 |
| EP2379481A1 (de) | 2011-10-26 |
| JP2012512229A (ja) | 2012-05-31 |
| US8901343B2 (en) | 2014-12-02 |
| KR20110101205A (ko) | 2011-09-15 |
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