JPS62132840A - アクリル酸又はメタクリル酸のフエニルエステルの製造法 - Google Patents
アクリル酸又はメタクリル酸のフエニルエステルの製造法Info
- Publication number
- JPS62132840A JPS62132840A JP60271376A JP27137685A JPS62132840A JP S62132840 A JPS62132840 A JP S62132840A JP 60271376 A JP60271376 A JP 60271376A JP 27137685 A JP27137685 A JP 27137685A JP S62132840 A JPS62132840 A JP S62132840A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- acrylic acid
- methacrylic acid
- acid
- ion exchange
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 26
- 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 25
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- -1 phenyl ester Chemical class 0.000 title claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 230000002378 acidificating effect Effects 0.000 claims description 17
- 238000005886 esterification reaction Methods 0.000 claims description 17
- 239000003456 ion exchange resin Substances 0.000 claims description 17
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 17
- 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 description 16
- 150000002989 phenols Chemical class 0.000 claims description 16
- 238000006297 dehydration reaction Methods 0.000 claims description 15
- 230000018044 dehydration Effects 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 description 68
- 239000000243 solution Substances 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 21
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 235000010338 boric acid Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910015444 B(OH)3 Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JAAJQSRLGAYGKZ-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2C(O)CCCC2=C1 JAAJQSRLGAYGKZ-UHFFFAOYSA-N 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical group CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- YHAIWSIWRGOXDL-UHFFFAOYSA-N 4-(2-methylphenyl)phenol Chemical compound CC1=CC=CC=C1C1=CC=C(O)C=C1 YHAIWSIWRGOXDL-UHFFFAOYSA-N 0.000 description 1
- AHXXIALEMINDAW-UHFFFAOYSA-N 4-(methoxymethyl)phenol Chemical compound COCC1=CC=C(O)C=C1 AHXXIALEMINDAW-UHFFFAOYSA-N 0.000 description 1
- PEJIZIIPFKEOTF-UHFFFAOYSA-N 4-(oxolan-2-ylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CC1OCCC1 PEJIZIIPFKEOTF-UHFFFAOYSA-N 0.000 description 1
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 1
- HJSPWKGEPDZNLK-UHFFFAOYSA-N 4-benzylphenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1 HJSPWKGEPDZNLK-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 239000008096 xylene Substances 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 |
|---|---|---|---|
| JP60271376A JPS62132840A (ja) | 1985-12-04 | 1985-12-04 | アクリル酸又はメタクリル酸のフエニルエステルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60271376A JPS62132840A (ja) | 1985-12-04 | 1985-12-04 | アクリル酸又はメタクリル酸のフエニルエステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62132840A true JPS62132840A (ja) | 1987-06-16 |
| JPH0210138B2 JPH0210138B2 (enrdf_load_stackoverflow) | 1990-03-06 |
Family
ID=17499205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60271376A Granted JPS62132840A (ja) | 1985-12-04 | 1985-12-04 | アクリル酸又はメタクリル酸のフエニルエステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62132840A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006136842A (ja) * | 2004-11-15 | 2006-06-01 | Toagosei Co Ltd | エステル化触媒 |
| JP2007106749A (ja) * | 2005-09-13 | 2007-04-26 | Osaka Organic Chem Ind Ltd | ハイドロキノンモノ（メタ）アクリレートの製造方法 |
| JP2012531452A (ja) * | 2009-06-30 | 2012-12-10 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | 脂肪族カルボン酸のエステルの連続的製造方法 |
| KR20160135275A (ko) | 2014-06-12 | 2016-11-25 | 미쯔비시 레이온 가부시끼가이샤 | (메트)아크릴산 에스터의 제조 방법 및 카복실산 방향족 에스터의 제조 방법 |
| JP2017171623A (ja) * | 2016-03-25 | 2017-09-28 | オルガノ株式会社 | エステル化合物の製造方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0467538U (enrdf_load_stackoverflow) * | 1990-10-18 | 1992-06-16 | ||
| JPH06227309A (ja) * | 1993-02-02 | 1994-08-16 | Shin Caterpillar Mitsubishi Ltd | サービスカー |
| JP5039820B2 (ja) * | 2010-09-27 | 2012-10-03 | 昭和電工株式会社 | 二価フェノール類モノ（メタ）アクリレートを製造する方法 |
-
1985
- 1985-12-04 JP JP60271376A patent/JPS62132840A/ja active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006136842A (ja) * | 2004-11-15 | 2006-06-01 | Toagosei Co Ltd | エステル化触媒 |
| JP2007106749A (ja) * | 2005-09-13 | 2007-04-26 | Osaka Organic Chem Ind Ltd | ハイドロキノンモノ（メタ）アクリレートの製造方法 |
| JP2012531452A (ja) * | 2009-06-30 | 2012-12-10 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | 脂肪族カルボン酸のエステルの連続的製造方法 |
| KR20160135275A (ko) | 2014-06-12 | 2016-11-25 | 미쯔비시 레이온 가부시끼가이샤 | (메트)아크릴산 에스터의 제조 방법 및 카복실산 방향족 에스터의 제조 방법 |
| US9796652B2 (en) | 2014-06-12 | 2017-10-24 | Mitsubishi Chemical Corporation | Method for manufacturing (meth) acrylic acid ester and method for manufacturing aromatic carboxylic acid ester |
| JP2017171623A (ja) * | 2016-03-25 | 2017-09-28 | オルガノ株式会社 | エステル化合物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0210138B2 (enrdf_load_stackoverflow) | 1990-03-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI284123B (en) | Process for producing bisphenol A | |
| JP2000191590A (ja) | （メタ）アクリル酸フェニルエステルの製造方法 | |
| JPS62132840A (ja) | アクリル酸又はメタクリル酸のフエニルエステルの製造法 | |
| FR2592040A1 (fr) | Procede de synthese d'anhydrides (meth)acryliques | |
| JPS60172945A (ja) | フタル酸エステル類の製造方法 | |
| SE468714B (sv) | Foerfarande foer framstaellning av ditrimetylolpropan | |
| JPS6075446A (ja) | ３，５−ジ−ｔｅｒｔ−ブチル−４−ヒドロキシ安息香酸をエステル化するための改良された方法 | |
| EP0165529B1 (en) | Process for producing phenyl methacrylate or acrylate | |
| JPH04211031A (ja) | 精製パラ−クミルフェノール | |
| US4301297A (en) | Process for preparing dimethylaminoethyl methacrylate | |
| JPH0967306A (ja) | イソボルニル（メタ）アクリレートの製造方法 | |
| JPS637571B2 (enrdf_load_stackoverflow) | ||
| EP0044510B1 (en) | Process for the preparation of diaryl esters | |
| EP0669312B1 (en) | Method of preparing a vinyl compound with hydroxy group | |
| JP4238606B2 (ja) | 芳香族エステル化合物の製造方法 | |
| JPS61165349A (ja) | 多官能エステルの製法 | |
| US4081587A (en) | Process for the manufacture of ethylene-acrylic acid copolymers | |
| JPH07188108A (ja) | ジ（メタ）アクリル酸エステルの製造方法 | |
| JPS6042777B2 (ja) | トリメチロ−ルプロパントリアクリレ−ト又はトリメチロ−ルプロパントリメタクリレ−トの製造方法 | |
| SU1740365A1 (ru) | Способ получени м-феноксифенола | |
| JPS6377841A (ja) | 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 | |
| JPS63119432A (ja) | ４，４′−ジヒドロキシビフエニルの製造方法 | |
| JPH0211533A (ja) | スチレン化フエノールの製造方法 | |
| JPH03275644A (ja) | α―ヒドロキシイソ酪酸の製造方法 | |
| JP4586504B2 (ja) | 芳香族エステル化合物の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |