JP6241314B2 - アクリル酸ブチルの製造方法 - Google Patents
アクリル酸ブチルの製造方法 Download PDFInfo
- Publication number
- JP6241314B2 JP6241314B2 JP2014032781A JP2014032781A JP6241314B2 JP 6241314 B2 JP6241314 B2 JP 6241314B2 JP 2014032781 A JP2014032781 A JP 2014032781A JP 2014032781 A JP2014032781 A JP 2014032781A JP 6241314 B2 JP6241314 B2 JP 6241314B2
- Authority
- JP
- Japan
- Prior art keywords
- butyl acrylate
- acrylic acid
- butanol
- washing
- water
- 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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Links
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 title claims description 52
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 69
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 59
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 59
- 238000004140 cleaning Methods 0.000 claims description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- 239000007788 liquid Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 27
- 238000006386 neutralization reaction Methods 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 230000003472 neutralizing effect Effects 0.000 claims description 6
- 238000005406 washing Methods 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000012044 organic layer Substances 0.000 description 28
- 239000003377 acid catalyst Substances 0.000 description 25
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 21
- 239000011734 sodium Substances 0.000 description 21
- 229910052708 sodium Inorganic materials 0.000 description 21
- 238000005886 esterification reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000000605 extraction Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000010410 layer Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- 238000000066 reactive distillation Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 5
- 238000005979 thermal decomposition reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- 229940048053 acrylate Drugs 0.000 description 3
- -1 acrylic ester Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- BMOACRKLCOIODC-UHFFFAOYSA-N butyl 3-butoxypropanoate Chemical compound CCCCOCCC(=O)OCCCC BMOACRKLCOIODC-UHFFFAOYSA-N 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KOTRGELQEAFGGI-UHFFFAOYSA-N butan-2-ol;prop-2-enoic acid Chemical compound CCC(C)O.OC(=O)C=C KOTRGELQEAFGGI-UHFFFAOYSA-N 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Images
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014032781A JP6241314B2 (ja) | 2014-02-24 | 2014-02-24 | アクリル酸ブチルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014032781A JP6241314B2 (ja) | 2014-02-24 | 2014-02-24 | アクリル酸ブチルの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015157777A JP2015157777A (ja) | 2015-09-03 |
| JP2015157777A5 JP2015157777A5 (enrdf_load_stackoverflow) | 2016-11-10 |
| JP6241314B2 true JP6241314B2 (ja) | 2017-12-06 |
Family
ID=54182092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014032781A Active JP6241314B2 (ja) | 2014-02-24 | 2014-02-24 | アクリル酸ブチルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP6241314B2 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113121343A (zh) * | 2021-03-15 | 2021-07-16 | 江苏新东风化工科技有限公司 | 一种丙烯酸正丁酯的中和生产工艺 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2723089B1 (fr) * | 1994-07-28 | 1996-09-06 | Atochem Elf Sa | Procede de fabrication de l'acrylate de butyle par esterification directe |
| JP2003226672A (ja) * | 2001-11-27 | 2003-08-12 | Mitsubishi Chemicals Corp | （メタ）アクリル酸エステルの製造方法 |
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- 2014-02-24 JP JP2014032781A patent/JP6241314B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015157777A (ja) | 2015-09-03 |
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