BR112015006802B1 - Processo para a produção de benzoato de 2-butoxi-etila - Google Patents
Processo para a produção de benzoato de 2-butoxi-etila Download PDFInfo
- Publication number
- BR112015006802B1 BR112015006802B1 BR112015006802-2A BR112015006802A BR112015006802B1 BR 112015006802 B1 BR112015006802 B1 BR 112015006802B1 BR 112015006802 A BR112015006802 A BR 112015006802A BR 112015006802 B1 BR112015006802 B1 BR 112015006802B1
- Authority
- BR
- Brazil
- Prior art keywords
- butoxy
- ethyl benzoate
- column
- stream
- process according
- Prior art date
Links
- NMBQBIACXMPEQB-UHFFFAOYSA-N 2-butoxyethyl benzoate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1 NMBQBIACXMPEQB-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 61
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000009928 pasteurization Methods 0.000 claims abstract description 20
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 14
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 14
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000047 product Substances 0.000 claims description 39
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 30
- 238000005192 partition Methods 0.000 claims description 29
- 239000012535 impurity Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 7
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- -1 glycol ester Chemical class 0.000 description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 27
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- 238000000926 separation method Methods 0.000 description 9
- 238000004088 simulation Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- 150000002334 glycols Chemical class 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000005265 energy consumption Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000000998 batch distillation Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229920001600 hydrophobic polymer Polymers 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- IRZWYOFWPMYFHG-UHFFFAOYSA-N butanal Chemical compound CCCC=O.CCCC=O IRZWYOFWPMYFHG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Images
Classifications
-
- 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
- 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)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261706835P | 2012-09-28 | 2012-09-28 | |
| US61/706,835 | 2012-09-28 | ||
| PCT/US2013/061368 WO2014052298A2 (en) | 2012-09-28 | 2013-09-24 | Process for the production of high purity glycol esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112015006802A2 BR112015006802A2 (pt) | 2017-07-04 |
| BR112015006802B1 true BR112015006802B1 (pt) | 2021-12-21 |
Family
ID=49301678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112015006802-2A BR112015006802B1 (pt) | 2012-09-28 | 2013-09-24 | Processo para a produção de benzoato de 2-butoxi-etila |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9481629B2 (enExample) |
| EP (1) | EP2900627B1 (enExample) |
| JP (1) | JP2015530416A (enExample) |
| CN (1) | CN104797551B (enExample) |
| BR (1) | BR112015006802B1 (enExample) |
| CA (1) | CA2885432C (enExample) |
| ES (1) | ES2617733T3 (enExample) |
| WO (1) | WO2014052298A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2952237A1 (en) * | 2014-06-02 | 2015-12-09 | Sulzer Chemtech AG | Method for purification of benzoic acid |
| ES2709386T3 (es) * | 2014-06-24 | 2019-04-16 | Dow Global Technologies Llc | Proceso para producir agentes coalescentes con contenidos bajos de COV |
| ES2705759T3 (es) | 2014-06-24 | 2019-03-26 | Dow Global Technologies Llc | Procedimiento para producir éter-ésteres de glicol con bajo nivel de COV |
| SG11201802755WA (en) | 2015-10-14 | 2018-05-30 | Dow Global Technologies Llc | Process for purification of methyl methacrylate |
| KR101935239B1 (ko) | 2017-05-29 | 2019-01-04 | 한국과학기술연구원 | 에스터-알코올 혼합물로부터 에스터 화합물의 분리방법 |
| CN114072213A (zh) * | 2019-06-27 | 2022-02-18 | 沙特基础工业全球技术公司 | 使用分壁式蒸馏塔分离乙二醇混合物的方法 |
| CN110183326A (zh) * | 2019-07-03 | 2019-08-30 | 上海中溶科技有限公司 | 一种连续制备提纯苯甲酸乙二醇单丁醚酯的方法 |
| CN110283073A (zh) * | 2019-07-03 | 2019-09-27 | 上海中溶科技有限公司 | 苯甲酸乙二醇单丁醚酯及其制备方法 |
| CN110698340A (zh) * | 2019-10-21 | 2020-01-17 | 天津大学 | 一种反应精馏隔壁塔技术生产乳酸乙酯的工艺方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4658003A (en) | 1984-07-02 | 1987-04-14 | The Dow Chemical Company | Novel phosphinyl-containing ethylenically unsaturated compounds |
| US4733005A (en) | 1986-04-21 | 1988-03-22 | The Dow Chemical Company | Phosphinyl-containing ethylenically unsaturated compounds |
| JPH0350246A (ja) * | 1989-07-17 | 1991-03-04 | Kyowa Yuka Kk | 新規可塑剤 |
| DE19618152C1 (de) * | 1996-05-07 | 1997-08-14 | Huels Chemische Werke Ag | Verfahren zur Trennung von Rohester im DMT-Prozeß |
| CN1169421A (zh) * | 1996-05-07 | 1998-01-07 | 希尔斯股份公司 | 对苯二甲酸二甲酯工艺中的粗酯分离方法 |
| DE10160180A1 (de) * | 2001-12-07 | 2003-06-18 | Basf Ag | Verfahren zur Isolierung von Trimethylolpropan aus einem Reaktionsgemisch |
| EP1371633A1 (en) | 2002-06-14 | 2003-12-17 | Bayer Ag | Process for the purification of mixtures of toluenediisocyanate incorporating a dividing-wall distillation column |
| JP2005239564A (ja) * | 2004-02-24 | 2005-09-08 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸エステルの製造方法 |
| US20090288939A1 (en) * | 2008-05-20 | 2009-11-26 | Smith Michael R | Distillation Apparatus |
| CN101328119B (zh) * | 2008-06-20 | 2011-03-23 | 中国石油大学(华东) | 一种乙酸甲酯的合成工艺方法及其装置 |
| CN101357887A (zh) * | 2008-07-31 | 2009-02-04 | 中国石油大学(华东) | 一种乙酸乙酯的合成工艺方法及其装置 |
| US8372516B2 (en) | 2008-10-31 | 2013-02-12 | Basf Se | (Meth)acrylate phosphonic esters as adhesion promoters |
| US7956157B2 (en) | 2008-12-31 | 2011-06-07 | Fina Technology, Inc. | Processes using dividing wall distillation column |
| JP5811410B2 (ja) | 2009-03-19 | 2015-11-11 | エルジー・ケム・リミテッド | 高純度のアクリル酸生産のための分離壁型蒸留塔及びこれを利用した分別蒸留方法 |
| CN202438166U (zh) * | 2012-01-06 | 2012-09-19 | 长岭炼化岳阳工程设计有限公司 | 提纯醋酸叔丁酯用带分隔壁的分离装置 |
| CN102584576A (zh) * | 2012-01-06 | 2012-07-18 | 长岭炼化岳阳工程设计有限公司 | 利用分隔壁塔提纯醋酸叔丁酯的方法及其装置 |
-
2013
- 2013-09-24 CN CN201380059842.8A patent/CN104797551B/zh active Active
- 2013-09-24 ES ES13771735.1T patent/ES2617733T3/es active Active
- 2013-09-24 EP EP13771735.1A patent/EP2900627B1/en active Active
- 2013-09-24 WO PCT/US2013/061368 patent/WO2014052298A2/en not_active Ceased
- 2013-09-24 CA CA2885432A patent/CA2885432C/en active Active
- 2013-09-24 BR BR112015006802-2A patent/BR112015006802B1/pt active IP Right Grant
- 2013-09-24 JP JP2015534596A patent/JP2015530416A/ja active Pending
- 2013-09-24 US US14/430,719 patent/US9481629B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN104797551A (zh) | 2015-07-22 |
| WO2014052298A3 (en) | 2014-09-12 |
| ES2617733T3 (es) | 2017-06-19 |
| CN104797551B (zh) | 2016-08-31 |
| EP2900627A2 (en) | 2015-08-05 |
| BR112015006802A2 (pt) | 2017-07-04 |
| WO2014052298A2 (en) | 2014-04-03 |
| US20150274635A1 (en) | 2015-10-01 |
| CA2885432A1 (en) | 2014-04-03 |
| EP2900627B1 (en) | 2017-01-11 |
| JP2015530416A (ja) | 2015-10-15 |
| CA2885432C (en) | 2017-04-25 |
| US9481629B2 (en) | 2016-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 24/09/2013, OBSERVADAS AS CONDICOES LEGAIS. |