JPS6263544A - アクリル酸またはメタクリル酸のタ−シヤリ−ブチルエステルの製造方法 - Google Patents
アクリル酸またはメタクリル酸のタ−シヤリ−ブチルエステルの製造方法Info
- Publication number
- JPS6263544A JPS6263544A JP60183879A JP18387985A JPS6263544A JP S6263544 A JPS6263544 A JP S6263544A JP 60183879 A JP60183879 A JP 60183879A JP 18387985 A JP18387985 A JP 18387985A JP S6263544 A JPS6263544 A JP S6263544A
- Authority
- JP
- Japan
- Prior art keywords
- isobutylene
- acrylic acid
- reaction
- methacrylic acid
- tert
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 56
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims description 53
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 73
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 64
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000009835 boiling Methods 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 230000002378 acidificating effect Effects 0.000 claims abstract description 24
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 23
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 23
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000010409 thin film Substances 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 28
- 238000000926 separation method Methods 0.000 claims description 10
- 238000011084 recovery Methods 0.000 claims description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 7
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- SIINAHBZNVOMMM-UHFFFAOYSA-N 6-tert-butyl-2,3-dimethylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1C SIINAHBZNVOMMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 9
- 239000006227 byproduct Substances 0.000 abstract description 4
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 abstract description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 2
- 238000005194 fractionation Methods 0.000 abstract 2
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- IAHOUQOWMXVMEH-UHFFFAOYSA-N 2,4,6-trinitroaniline Chemical compound NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O IAHOUQOWMXVMEH-UHFFFAOYSA-N 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 19
- 239000007788 liquid Substances 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 230000007423 decrease Effects 0.000 description 9
- 239000012043 crude product Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 230000008014 freezing Effects 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910001882 dioxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229950007538 pecazine Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DELBTKKZBXDCEW-UHFFFAOYSA-M silver;n,n-dibutylcarbamodithioate Chemical compound [Ag+].CCCCN(C([S-])=S)CCCC DELBTKKZBXDCEW-UHFFFAOYSA-M 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60183879A JPS6263544A (ja) | 1985-08-23 | 1985-08-23 | アクリル酸またはメタクリル酸のタ−シヤリ−ブチルエステルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60183879A JPS6263544A (ja) | 1985-08-23 | 1985-08-23 | アクリル酸またはメタクリル酸のタ−シヤリ−ブチルエステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6263544A true JPS6263544A (ja) | 1987-03-20 |
| JPH0159261B2 JPH0159261B2 (enrdf_load_html_response) | 1989-12-15 |
Family
ID=16143426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60183879A Granted JPS6263544A (ja) | 1985-08-23 | 1985-08-23 | アクリル酸またはメタクリル酸のタ−シヤリ−ブチルエステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6263544A (enrdf_load_html_response) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004505101A (ja) * | 2000-07-28 | 2004-02-19 | ビーエーエスエフ アクチェンゲゼルシャフト | 脂肪族Ｃ１〜Ｃ４カルボン酸のｔ−ブチルエステルの製造方法 |
| WO2006082965A1 (ja) * | 2005-02-07 | 2006-08-10 | Mitsubishi Rayon Co., Ltd. | （メタ）アクリル酸ｔ－ブチルの合成方法 |
| CN107597187A (zh) * | 2017-10-11 | 2018-01-19 | 万华化学集团股份有限公司 | 连续生产（甲基）丙烯酸羟基酯和（甲基）丙烯酸二酯的方法及磺酸树脂催化剂 |
| KR20180092986A (ko) * | 2015-12-15 | 2018-08-20 | 바스프 에스이 | 에틸렌계 불포화 카르복실산의 tert-부틸 에스테르의 제조 |
-
1985
- 1985-08-23 JP JP60183879A patent/JPS6263544A/ja active Granted
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004505101A (ja) * | 2000-07-28 | 2004-02-19 | ビーエーエスエフ アクチェンゲゼルシャフト | 脂肪族Ｃ１〜Ｃ４カルボン酸のｔ−ブチルエステルの製造方法 |
| WO2006082965A1 (ja) * | 2005-02-07 | 2006-08-10 | Mitsubishi Rayon Co., Ltd. | （メタ）アクリル酸ｔ－ブチルの合成方法 |
| US7803964B2 (en) | 2005-02-07 | 2010-09-28 | Mitsubishi Rayon Co., Ltd. | Method for synthesizing t-butyl (meth)Acrylate |
| JP2012211177A (ja) * | 2005-02-07 | 2012-11-01 | Mitsubishi Rayon Co Ltd | （メタ）アクリル酸ｔ−ブチルの合成方法 |
| JP5114193B2 (ja) * | 2005-02-07 | 2013-01-09 | 三菱レイヨン株式会社 | （メタ）アクリル酸ｔ−ブチルの合成方法 |
| KR20180092986A (ko) * | 2015-12-15 | 2018-08-20 | 바스프 에스이 | 에틸렌계 불포화 카르복실산의 tert-부틸 에스테르의 제조 |
| JP2019501907A (ja) * | 2015-12-15 | 2019-01-24 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | エチレン性不飽和カルボン酸のｔｅｒｔ−ブチルエステルの製造 |
| CN107597187A (zh) * | 2017-10-11 | 2018-01-19 | 万华化学集团股份有限公司 | 连续生产（甲基）丙烯酸羟基酯和（甲基）丙烯酸二酯的方法及磺酸树脂催化剂 |
| CN107597187B (zh) * | 2017-10-11 | 2020-06-02 | 万华化学集团股份有限公司 | 连续生产(甲基)丙烯酸羟基酯和(甲基)丙烯酸二酯的方法及磺酸树脂催化剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0159261B2 (enrdf_load_html_response) | 1989-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |