CA2885432C - Process for the production of high purity glycol esters - Google Patents
Process for the production of high purity glycol esters Download PDFInfo
- Publication number
- CA2885432C CA2885432C CA2885432A CA2885432A CA2885432C CA 2885432 C CA2885432 C CA 2885432C CA 2885432 A CA2885432 A CA 2885432A CA 2885432 A CA2885432 A CA 2885432A CA 2885432 C CA2885432 C CA 2885432C
- Authority
- CA
- Canada
- Prior art keywords
- column
- dividing wall
- stream
- butanal
- distillation
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 150000002334 glycols Chemical class 0.000 title description 8
- 238000004821 distillation Methods 0.000 claims abstract description 60
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 42
- NMBQBIACXMPEQB-UHFFFAOYSA-N 2-butoxyethyl benzoate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1 NMBQBIACXMPEQB-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 18
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 18
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 37
- 239000012043 crude product Substances 0.000 claims description 15
- 239000012535 impurity Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 40
- 239000000047 product Substances 0.000 description 38
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 28
- -1 glycol ester Chemical class 0.000 description 24
- 239000000203 mixture Substances 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- 238000009835 boiling Methods 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 238000004088 simulation Methods 0.000 description 9
- 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 6
- 238000009928 pasteurization Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 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
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000012856 packing 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920001600 hydrophobic polymer Polymers 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 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
- 239000006227 byproduct Substances 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
- 230000001419 dependent effect Effects 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
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 239000000376 reactant 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
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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 |
|---|---|
| CA2885432A1 CA2885432A1 (en) | 2014-04-03 |
| CA2885432C true CA2885432C (en) | 2017-04-25 |
Family
ID=49301678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2885432A Active CA2885432C (en) | 2012-09-28 | 2013-09-24 | Process for the production of high purity glycol esters |
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 |
| CN106458832B (zh) * | 2014-06-24 | 2020-10-16 | 陶氏环球技术有限责任公司 | 用于制造低voc二醇醚酯的方法 |
| EP3160931B1 (en) * | 2014-06-24 | 2018-11-14 | Dow Global Technologies LLC | Process for producing low voc coalescing aids |
| WO2017065969A1 (en) | 2015-10-14 | 2017-04-20 | 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 |
| 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 |
| 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 |
| 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 (17)
| 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 |
| JPS64991A (en) * | 1987-06-24 | 1989-01-05 | Toshiba Corp | Information processor |
| 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 |
| CA2739713A1 (en) | 2008-10-31 | 2010-05-06 | 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 |
| US8932434B2 (en) | 2009-03-19 | 2015-01-13 | Lg Chem, Ltd. | Dividing wall distillation column for producing high purity acrylic acid and fractional distillation method using the same |
| 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 CA CA2885432A patent/CA2885432C/en active Active
- 2013-09-24 EP EP13771735.1A patent/EP2900627B1/en active Active
- 2013-09-24 JP JP2015534596A patent/JP2015530416A/ja active Pending
- 2013-09-24 CN CN201380059842.8A patent/CN104797551B/zh active Active
- 2013-09-24 BR BR112015006802-2A patent/BR112015006802B1/pt active IP Right Grant
- 2013-09-24 ES ES13771735.1T patent/ES2617733T3/es active Active
- 2013-09-24 US US14/430,719 patent/US9481629B2/en active Active
- 2013-09-24 WO PCT/US2013/061368 patent/WO2014052298A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US9481629B2 (en) | 2016-11-01 |
| CN104797551A (zh) | 2015-07-22 |
| ES2617733T3 (es) | 2017-06-19 |
| BR112015006802A2 (pt) | 2017-07-04 |
| US20150274635A1 (en) | 2015-10-01 |
| EP2900627B1 (en) | 2017-01-11 |
| CN104797551B (zh) | 2016-08-31 |
| BR112015006802B1 (pt) | 2021-12-21 |
| WO2014052298A3 (en) | 2014-09-12 |
| WO2014052298A2 (en) | 2014-04-03 |
| EP2900627A2 (en) | 2015-08-05 |
| JP2015530416A (ja) | 2015-10-15 |
| CA2885432A1 (en) | 2014-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20150318 |