JPS5877845A - アクリル酸エステルまたはメタクリル酸エステルの製造方法 - Google Patents
アクリル酸エステルまたはメタクリル酸エステルの製造方法Info
- Publication number
- JPS5877845A JPS5877845A JP17455781A JP17455781A JPS5877845A JP S5877845 A JPS5877845 A JP S5877845A JP 17455781 A JP17455781 A JP 17455781A JP 17455781 A JP17455781 A JP 17455781A JP S5877845 A JPS5877845 A JP S5877845A
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- meth
- ester
- alcohol
- acrylic
- 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
- 125000005396 acrylic acid ester group Chemical group 0.000 title abstract description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 50
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000004821 distillation Methods 0.000 claims abstract description 32
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 238000005886 esterification reaction Methods 0.000 claims abstract description 12
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims description 19
- -1 acrylic ester Chemical class 0.000 claims description 18
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ICSVICPOSIKFLO-UHFFFAOYSA-N [C].CC(=C)C(O)=O Chemical compound [C].CC(=C)C(O)=O ICSVICPOSIKFLO-UHFFFAOYSA-N 0.000 claims 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 11
- 238000011084 recovery Methods 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 14
- 239000012071 phase Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 125000005395 methacrylic acid group Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 241000951471 Citrus junos Species 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 241001062472 Stokellia anisodon Species 0.000 description 1
- 241001504592 Trachurus trachurus Species 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 231100000895 deafness Toxicity 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000016354 hearing loss disease Diseases 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003505 mequinol Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17455781A JPS5877845A (ja) | 1981-11-02 | 1981-11-02 | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
| US06/393,484 US4464229A (en) | 1981-07-09 | 1982-06-29 | Process for producing acrylic or methacrylic esters |
| BR8203983A BR8203983A (pt) | 1981-07-09 | 1982-07-08 | Processo para produzir ester acrilico ou metacrilico |
| FR8211987A FR2509294A1 (fr) | 1981-07-09 | 1982-07-08 | Procede de fabrication d'esters de l'acide acrylique ou methacrylique |
| MX193511A MX163005B (es) | 1981-07-09 | 1982-07-08 | Procedimiento mejorado para producir un ester acrilico o metacrilico |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17455781A JPS5877845A (ja) | 1981-11-02 | 1981-11-02 | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5877845A true JPS5877845A (ja) | 1983-05-11 |
| JPS6320415B2 JPS6320415B2 (en, 2012) | 1988-04-27 |
Family
ID=15980634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17455781A Granted JPS5877845A (ja) | 1981-07-09 | 1981-11-02 | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5877845A (en, 2012) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6357554A (ja) * | 1986-08-29 | 1988-03-12 | Mitsubishi Rayon Co Ltd | アクリル酸又はメタクリル酸のフエニルエステル類の製法 |
| JPH01139547A (ja) * | 1987-04-16 | 1989-06-01 | Nippon Shokubai Kagaku Kogyo Co Ltd | 高純度メタクリル酸エステルの製造方法 |
| JP2002507194A (ja) * | 1997-05-20 | 2002-03-05 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー コーポレイション | アクリル酸ブチルの精製方法 |
| JP2003521478A (ja) * | 1999-06-17 | 2003-07-15 | ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション | 平衡律速反応を行う方法 |
| JP2004529071A (ja) * | 2000-10-17 | 2004-09-24 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | モノアミントランスポータとの高い親和性を有する化合物 |
| JP2018537466A (ja) * | 2015-12-18 | 2018-12-20 | ローム アンド ハース カンパニーＲｏｈｍ Ａｎｄ Ｈａａｓ Ｃｏｍｐａｎｙ | メタクリル酸メチルの精製のための方法 |
-
1981
- 1981-11-02 JP JP17455781A patent/JPS5877845A/ja active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6357554A (ja) * | 1986-08-29 | 1988-03-12 | Mitsubishi Rayon Co Ltd | アクリル酸又はメタクリル酸のフエニルエステル類の製法 |
| JPH01139547A (ja) * | 1987-04-16 | 1989-06-01 | Nippon Shokubai Kagaku Kogyo Co Ltd | 高純度メタクリル酸エステルの製造方法 |
| JP2002507194A (ja) * | 1997-05-20 | 2002-03-05 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー コーポレイション | アクリル酸ブチルの精製方法 |
| JP2003521478A (ja) * | 1999-06-17 | 2003-07-15 | ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション | 平衡律速反応を行う方法 |
| JP2004529071A (ja) * | 2000-10-17 | 2004-09-24 | プレジデント アンド フェロウズ オブ ハーバード カレッジ | モノアミントランスポータとの高い親和性を有する化合物 |
| JP2018537466A (ja) * | 2015-12-18 | 2018-12-20 | ローム アンド ハース カンパニーＲｏｈｍ Ａｎｄ Ｈａａｓ Ｃｏｍｐａｎｙ | メタクリル酸メチルの精製のための方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6320415B2 (en, 2012) | 1988-04-27 |
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