JPS6160834B2 - - Google Patents

Info

Publication number: JPS6160834B2
Authority: JP; Japan
Prior art keywords: catalyst; reaction; acrylate; glycide; meth
Prior art date: 1978-06-14
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.): Expired

Application number

JP7096378A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54163513A (en

Inventor

Tatsuhei Tanabe

Juji Yokoyama

Masamiki Sakai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

NOF Corp

Original Assignee

Nippon Oil and Fats Co Ltd

Priority date (The priority date 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 date listed.)

1978-06-14

Filing date

1978-06-14

Publication date

1986-12-23

1978-06-14 Application filed by Nippon Oil and Fats Co Ltd filed Critical Nippon Oil and Fats Co Ltd

1978-06-14 Priority to JP7096378A priority Critical patent/JPS54163513A/ja

1979-12-26 Publication of JPS54163513A publication Critical patent/JPS54163513A/ja

1986-12-23 Publication of JPS6160834B2 publication Critical patent/JPS6160834B2/ja

Status Granted legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 claims description 23
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 13
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 11
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 7
-1 aromatic monocarboxylic acid Chemical class 0.000 claims description 6
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 5
238000005809 transesterification reaction Methods 0.000 claims description 5
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
235000010235 potassium benzoate Nutrition 0.000 claims description 3
239000004300 potassium benzoate Substances 0.000 claims description 3
229940103091 potassium benzoate Drugs 0.000 claims description 3
FRMWBRPWYBNAFB-UHFFFAOYSA-M potassium salicylate Chemical compound [K+].OC1=CC=CC=C1C([O-])=O FRMWBRPWYBNAFB-UHFFFAOYSA-M 0.000 claims description 3
229960003629 potassium salicylate Drugs 0.000 claims description 3
159000000007 calcium salts Chemical class 0.000 claims description 2
159000000003 magnesium salts Chemical class 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 22
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
238000001944 continuous distillation Methods 0.000 description 7
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000000034 method Methods 0.000 description 3
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
229950000688 phenothiazine Drugs 0.000 description 3
239000002253 acid Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000007664 blowing Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000010237 calcium benzoate Nutrition 0.000 description 1
239000004301 calcium benzoate Substances 0.000 description 1
HZQXCUSDXIKLGS-UHFFFAOYSA-L calcium;dibenzoate;trihydrate Chemical compound O.O.O.[Ca+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HZQXCUSDXIKLGS-UHFFFAOYSA-L 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 1
PJJZFXPJNUVBMR-UHFFFAOYSA-L magnesium benzoate Chemical compound [Mg+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 PJJZFXPJNUVBMR-UHFFFAOYSA-L 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229960004025 sodium salicylate Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1

Landscapes

Epoxy Compounds (AREA)

JP7096378A 1978-06-14 1978-06-14 Preparation of glycidyl (meth)acrylate Granted JPS54163513A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP7096378A JPS54163513A (en)	1978-06-14	1978-06-14	Preparation of glycidyl (meth)acrylate

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP7096378A JPS54163513A (en)	1978-06-14	1978-06-14	Preparation of glycidyl (meth)acrylate

Publications (2)

Publication Number	Publication Date
JPS54163513A JPS54163513A (en)	1979-12-26
JPS6160834B2 true JPS6160834B2 (de)	1986-12-23

Family

ID=13446670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7096378A Granted JPS54163513A (en)	1978-06-14	1978-06-14	Preparation of glycidyl (meth)acrylate

Country Status (1)

Country	Link
JP (1)	JPS54163513A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN108707126B (zh) *	2018-07-03	2020-06-02	山东柳湾新材料有限公司	采用微通道反应装置合成甲基丙烯酸缩水甘油酯的方法

1978
- 1978-06-14 JP JP7096378A patent/JPS54163513A/ja active Granted

Also Published As

Publication number	Publication date
JPS54163513A (en)	1979-12-26

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