ES2554170T3 - Producción de ésteres de ácidos carboxílicos por arrastre con vapor de alcohol - Google Patents
Producción de ésteres de ácidos carboxílicos por arrastre con vapor de alcohol Download PDFInfo
- Publication number
- ES2554170T3 ES2554170T3 ES09799604.5T ES09799604T ES2554170T3 ES 2554170 T3 ES2554170 T3 ES 2554170T3 ES 09799604 T ES09799604 T ES 09799604T ES 2554170 T3 ES2554170 T3 ES 2554170T3
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- Spain
- Prior art keywords
- alcohol
- reaction
- reaction mixture
- reactor
- alcohol vapor
- 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.)
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- 150000001733 carboxylic acid esters Chemical class 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 68
- 239000011541 reaction mixture Substances 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000012071 phase Substances 0.000 claims abstract description 26
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 19
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- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000008346 aqueous phase Substances 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
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- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 238000010348 incorporation Methods 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
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000007769 metal material Substances 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
- 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
- 238000002156 mixing Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 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
- 238000006386 neutralization reaction Methods 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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
- 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
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium(IV) ethoxide Substances [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000009466 transformation Effects 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D19/00—Degasification of liquids
- B01D19/0005—Degasification of liquids with one or more auxiliary substances
- B01D19/001—Degasification of liquids with one or more auxiliary substances by bubbling steam through the liquid
- B01D19/0015—Degasification of liquids with one or more auxiliary substances by bubbling steam through the liquid in contact columns containing plates, grids or other filling elements
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/36—Azeotropic distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/38—Steam distillation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08171795 | 2008-12-16 | ||
| EP08171795 | 2008-12-16 | ||
| PCT/EP2009/067179 WO2010076194A1 (de) | 2008-12-16 | 2009-12-15 | Herstellung von carbonsäureestern unter strippen mit alkohol-dampf |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2554170T3 true ES2554170T3 (es) | 2015-12-16 |
Family
ID=42167488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09799604.5T Active ES2554170T3 (es) | 2008-12-16 | 2009-12-15 | Producción de ésteres de ácidos carboxílicos por arrastre con vapor de alcohol |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8901344B2 (enExample) |
| EP (1) | EP2379482B1 (enExample) |
| JP (1) | JP5698146B2 (enExample) |
| KR (1) | KR101733814B1 (enExample) |
| CN (1) | CN102256922B (enExample) |
| CA (1) | CA2746571C (enExample) |
| ES (1) | ES2554170T3 (enExample) |
| MY (1) | MY157837A (enExample) |
| WO (1) | WO2010076194A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN102295564B (zh) * | 2011-07-25 | 2013-07-10 | 浙江庆安化工有限公司 | 一种dop连续化生产工艺 |
| CN103822937A (zh) * | 2012-11-16 | 2014-05-28 | 哈尔滨飞机工业集团有限责任公司 | 三氯乙烯槽液沸点测试方法 |
| CN103113231A (zh) * | 2013-02-27 | 2013-05-22 | 寿光市鲁源盐化有限公司 | 二烯丙基二甘醇碳酸酯的合成方法 |
| TWI466863B (zh) * | 2013-03-21 | 2015-01-01 | Chang Chun Plastics Co Ltd | 對苯二甲酸二（２－乙基己酯）之製造方法 |
| 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 |
| 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 |
| CN105111074B (zh) * | 2015-07-20 | 2018-02-13 | 浙江大学 | 一种碱减量废水固体残渣甲酯化回收利用方法 |
| CN105111075A (zh) * | 2015-08-28 | 2015-12-02 | 华东理工大学 | 邻苯二甲酸酯类增塑剂连续生产新工艺 |
| KR101663586B1 (ko) | 2016-04-28 | 2016-10-10 | 애경유화주식회사 | 차별화 된 반응 온도 제어를 이용하여 반응 전환 속도를 높인 디옥틸테레프탈레이트의 제조방법 |
| 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 |
| KR102506500B1 (ko) * | 2018-11-29 | 2023-03-06 | 주식회사 엘지화학 | 디알킬 테레프탈레이트계 조성물의 제조방법 |
| KR102162204B1 (ko) * | 2019-04-04 | 2020-10-06 | 주식회사 엘지화학 | 에스터계 조성물의 제조방법 및 제조 시스템 |
| US11512166B2 (en) | 2019-04-04 | 2022-11-29 | Lg Chem, Ltd. | Method and system for manufacturing ester-based composition |
| KR102489173B1 (ko) * | 2019-07-04 | 2023-01-18 | 주식회사 엘지화학 | 열교환 시스템 및 이를 포함하는 디에스터계 조성물 제조 시스템 |
| KR102489172B1 (ko) * | 2019-07-04 | 2023-01-18 | 주식회사 엘지화학 | 디에스터계 물질의 제조 유닛 및 이를 포함하는 디에스터계 물질의 제조 시스템 |
| 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 |
| KR102489174B1 (ko) * | 2019-07-04 | 2023-01-18 | 주식회사 엘지화학 | 디에스터계 조성물의 제조 시스템 및 방법 |
| 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 |
| JP7293564B2 (ja) * | 2019-09-27 | 2023-06-20 | エルジー・ケム・リミテッド | ジエステル系物質の製造方法 |
| CN110938000A (zh) * | 2019-12-09 | 2020-03-31 | 江苏国胶新材料有限公司 | 一种丙烯酸异辛酯的生产工艺方法 |
| WO2022065852A1 (ko) * | 2020-09-24 | 2022-03-31 | 주식회사 엘지화학 | 에스터계 조성물의 제조방법 |
| US12551822B2 (en) * | 2022-07-07 | 2026-02-17 | Uop Llc | Process for recovery of pyrolysis oil extraction solvent |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2503195C3 (de) | 1975-01-27 | 1984-10-18 | Henkel KGaA, 4000 Düsseldorf | Verfahren und Vorrichtung zur kontinuierlichen katalytischen Veresterung von Fettsäuren mit Alkoholen |
| DE3809417A1 (de) | 1988-03-21 | 1989-10-12 | Henkel Kgaa | Verfahren zur kontinuierlichen veresterung von fettsaeuren |
| GB8618888D0 (en) * | 1986-08-01 | 1986-09-10 | Davy Mckee Ltd | Process |
| 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 |
| US5324853A (en) | 1993-01-19 | 1994-06-28 | Exxon Chemical Patents Inc. | Process for the production of plasticizer and polyolesters |
| DE4339713A1 (de) | 1993-11-22 | 1995-05-24 | Basf Ag | Verfahren zur Oligomerisierung von Olefinen zu hochlinearen Oligomeren und Katalysatoren dafür |
| ES2158419T3 (es) | 1996-10-14 | 2001-09-01 | Bayer Ag | Procedimiento de obtencion de esteres o de alcoholatos con separacion de agua. |
| JPH11189569A (ja) * | 1997-12-25 | 1999-07-13 | Mitsubishi Chemical Corp | ジアルキルフタレートの製造方法 |
| DE19955593A1 (de) | 1999-11-18 | 2001-05-23 | Basf Ag | C13-Alkoholgemisch und funktionalisiertes C13-Alkoholgemisch |
| 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 |
| TWI324592B (en) | 2002-11-28 | 2010-05-11 | Sulzer Chemtech Ag | A method for the esterification of a fatty acid |
| 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 |
| BRPI0815783A2 (pt) | 2007-08-31 | 2015-02-24 | Basf Se | Processo para a preparação de 1,2-propanodiol. |
| CN101855190A (zh) | 2007-08-31 | 2010-10-06 | 巴斯夫欧洲公司 | 通过甘油的低压氢化制备1,2-丙二醇的方法 |
| CN101855945B (zh) | 2007-11-13 | 2013-10-23 | 奥斯兰姆有限公司 | 用于驱动高压放电灯的电路装置和方法 |
| EP2107064A1 (de) | 2008-04-02 | 2009-10-07 | Basf Se | Verfahren zur Herstellung von Triamiden aus Ammoniak und Amido-Dichloriden |
| WO2009121881A1 (de) | 2008-04-01 | 2009-10-08 | Basf Se | Verfahren zur farbaufhellung von polyisocyanaten mit ozonhaltigem gas |
-
2009
- 2009-12-15 EP EP09799604.5A patent/EP2379482B1/de active Active
- 2009-12-15 CA CA2746571A patent/CA2746571C/en not_active Expired - Fee Related
- 2009-12-15 KR KR1020117016502A patent/KR101733814B1/ko not_active Expired - Fee Related
- 2009-12-15 JP JP2011541391A patent/JP5698146B2/ja not_active Expired - Fee Related
- 2009-12-15 CN CN200980150480.7A patent/CN102256922B/zh not_active Expired - Fee Related
- 2009-12-15 MY MYPI2011002712A patent/MY157837A/en unknown
- 2009-12-15 ES ES09799604.5T patent/ES2554170T3/es active Active
- 2009-12-15 US US13/140,274 patent/US8901344B2/en not_active Expired - Fee Related
- 2009-12-15 WO PCT/EP2009/067179 patent/WO2010076194A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2746571C (en) | 2017-08-22 |
| US8901344B2 (en) | 2014-12-02 |
| US20110301377A1 (en) | 2011-12-08 |
| CN102256922A (zh) | 2011-11-23 |
| JP2012512231A (ja) | 2012-05-31 |
| CA2746571A1 (en) | 2010-07-08 |
| CN102256922B (zh) | 2015-09-09 |
| KR101733814B1 (ko) | 2017-05-08 |
| EP2379482B1 (de) | 2015-08-26 |
| EP2379482A1 (de) | 2011-10-26 |
| KR20110101206A (ko) | 2011-09-15 |
| MY157837A (en) | 2016-07-29 |
| JP5698146B2 (ja) | 2015-04-08 |
| WO2010076194A1 (de) | 2010-07-08 |
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