JPS6160834B2 - - Google Patents
Info
- Publication number
- JPS6160834B2 JPS6160834B2 JP7096378A JP7096378A JPS6160834B2 JP S6160834 B2 JPS6160834 B2 JP S6160834B2 JP 7096378 A JP7096378 A JP 7096378A JP 7096378 A JP7096378 A JP 7096378A JP S6160834 B2 JPS6160834 B2 JP S6160834B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- acrylate
- glycide
- meth
- 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.)
- Expired
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)
Description
【発明の詳細な説明】
本発明は、メチルメタクリレートまたはメチル
アクリレート〔以下両者をメチル（メタ）アクリ
レートという〕とグリシドとのエステル交換反応
において、触媒の存在下で、グリシジルメタクリ
レートまたはグリシジルアクリレート〔以下両者
をグリシジル（メタ）アクリレートという〕を製
造する方法に関する。Detailed Description of the Invention The present invention relates to a transesterification reaction between methyl methacrylate or methyl acrylate (hereinafter both referred to as methyl (meth)acrylate) and glycide in the presence of a catalyst. (referred to as glycidyl (meth)acrylate)].
触媒の存在下で、メチル（メタ）アクリレート
とグリシドとのエステル交換反応により、グリシ
ジル（メタ）アクリレートを製造することは、す
でに公知である。例えば触媒として、ホスフイ
ン類を用いる方法（特公昭47−38421号）、アル
カリアルコラートを用いる方法（特開昭50−
154205号）、シアン化アルカリなどを用いる方
法（特公昭53−6133号）などが知られている。し
かしながらこれらの触媒を用いた場合、工業的
な収率が低い、反応中にポリマーの発生を完全
におさえることが困難である、副反応による製
品純度の低下が避けられないなどの欠点がある。
特に重大な欠点は、これらの触媒を用いた場合、
反応系から触媒を完全に除去することがきわめて
困難であり、このため反応液を連続蒸留してグリ
シジル（メタ）アクリレートを得ることが困難な
点である。また上記従来の触媒はいずれも危険な
薬品であるために工業的規模での取扱いおよび保
管上に問題があつた。 It is already known to produce glycidyl (meth)acrylate by transesterification of methyl (meth)acrylate with glycide in the presence of a catalyst. For example, a method using phosphines as a catalyst (Japanese Patent Publication No. 47-38421), a method using an alkali alcoholate (Japanese Patent Publication No. 50-1988),
154205) and a method using alkali cyanide (Japanese Patent Publication No. 53-6133). However, when these catalysts are used, there are drawbacks such as low industrial yields, difficulty in completely suppressing the generation of polymer during the reaction, and unavoidable reduction in product purity due to side reactions.
A particularly serious drawback is that when these catalysts are used,
It is extremely difficult to completely remove the catalyst from the reaction system, which makes it difficult to continuously distill the reaction solution to obtain glycidyl (meth)acrylate. Furthermore, since all of the above conventional catalysts are dangerous chemicals, they pose problems in handling and storage on an industrial scale.
本発明者らは、これらの欠点を克服すべく鋭意
検討を重ねた結果、芳香族モノカルボン酸金属塩
が上記のエステル交換反応の触媒としてきわめて
有効、かつ工業的に有利なものであることを見出
し、本発明に到達した。 As a result of intensive studies to overcome these drawbacks, the present inventors have found that aromatic monocarboxylic acid metal salts are extremely effective and industrially advantageous as catalysts for the above-mentioned transesterification reactions. Heading, we arrived at the present invention.
本発明は、メチル（メタ）アクリレートとグリ
シドとのエステル交換反応において、触媒として
芳香族モノカルボン酸金属塩を使用するグリシジ
ル（メタ）アクリレートの製造法である。 The present invention is a method for producing glycidyl (meth)acrylate using an aromatic monocarboxylic acid metal salt as a catalyst in the transesterification reaction between methyl (meth)acrylate and glycide.
本発明に用いる芳香族モノカルボン酸として
は、安息香酸、アルキル安息香酸（例えば、o-、
m-及びp-トルイル酸、o-、m-及びp-エチル安息
香酸）、α及びβナフトエ酸、アルキルナフトエ
酸、サリチル酸などがあり、金属塩としては、カ
リウム塩、ナトリウム塩、マグネシウム塩および
カルシウム塩がある。上記の中で、カリウム塩が
特に有効であり、安息香酸カリウム、サリチル酸
カリウムが特にすぐれた触媒である。なお触媒の
使用量は、グリシド１モル当り0.005モル〜0.1モ
ル、特に0.01〜0.05モル使用するのが好ましい。 Aromatic monocarboxylic acids used in the present invention include benzoic acid, alkylbenzoic acids (e.g. o - ,
m - and p -toluic acid, o - , m - and p -ethylbenzoic acid), α and β naphthoic acid, alkylnaphthoic acid, salicylic acid, etc.; metal salts include potassium salt, sodium salt, magnesium salt and There are calcium salts. Among the above, potassium salts are particularly effective, and potassium benzoate and potassium salicylate are particularly excellent catalysts. The amount of catalyst to be used is preferably 0.005 mol to 0.1 mol, particularly 0.01 to 0.05 mol, per mol of glycide.
本発明においては出発物質としてメチル（メ
タ）アクリレートおよびグリシドを使用する。反
応に際しては、公知の重合禁止剤たとえばヒドロ
キノン、ヒドロキノンモノメチルエーテル、アミ
ノフエノール、シフエニルアミン、フエノチアジ
ンなどの存在下で行い、その添加量は全原料重量
に対して50〜1500ppmが適当である。メチル
（メタ）アクリレートとクリシドとの反応モル比
は15：１〜２：１で行い、好ましくは、10：１〜
４：１で行う。反応温度は、40〜100℃、好まし
くは50〜80℃である。反応は減圧下で空気を反応
液中に少量入れながら行い、同時に副生してくる
メタノールを過剰のメチル（メタ）アクリレート
との共沸により連続的に除去しながら進め、かつ
反応系のモル比をつねに15：１〜２：１に保つよ
うにする。このようにすれば1.5〜４時間で反応
は完了する。つぎに反応液を冷却し、ろ過により
触媒を除去回収後、ろ液を連続蒸留することによ
つてグリシジル（メタ）アクリレートが得られ
る。 In the present invention, methyl (meth)acrylate and glycide are used as starting materials. The reaction is carried out in the presence of a known polymerization inhibitor such as hydroquinone, hydroquinone monomethyl ether, aminophenol, cyphenylamine, phenothiazine, etc., and the appropriate amount thereof is 50 to 1500 ppm based on the weight of the total raw materials. The reaction molar ratio between methyl (meth)acrylate and criside is 15:1 to 2:1, preferably 10:1 to 2:1.
Do it at a ratio of 4:1. The reaction temperature is 40-100°C, preferably 50-80°C. The reaction is carried out under reduced pressure while introducing a small amount of air into the reaction solution, and at the same time, methanol produced as a by-product is continuously removed by azeotropy with excess methyl (meth)acrylate, and the molar ratio of the reaction system is Always keep the ratio between 15:1 and 2:1. In this way, the reaction will be completed in 1.5 to 4 hours. Next, the reaction solution is cooled, the catalyst is removed and recovered by filtration, and the filtrate is continuously distilled to obtain glycidyl (meth)acrylate.
本発明に使用する触媒は、いずれも反応中に重
合物および副反応物を生成せず、したがつて、得
られるグリシジル（メタ）アクリレートは、高純
度（98％以上）かつ高収率（89〜93％）である。
本発明に用いる触媒は、いずれも反応液から簡単
なろ過により容易にかつ完全に除去回収できる。
このためにろ液をただちに連続蒸留することが可
能となり、工業的にきわめて有利にグリシジル
（メタ）アクリレートを得ることができる。また
本発明に用いる触媒は、芳香族モノカルボン酸金
属塩であることから安全であり、その取扱いおよ
び保管上特に注意を要しないという利点を合わせ
て有している。 None of the catalysts used in the present invention generates polymers or side-reactants during the reaction, and therefore the glycidyl (meth)acrylate obtained has high purity (98% or more) and high yield (89% or more). ~93%).
Any catalyst used in the present invention can be easily and completely removed and recovered from the reaction solution by simple filtration.
This makes it possible to immediately carry out continuous distillation of the filtrate, making it possible to obtain glycidyl (meth)acrylate with great industrial advantage. Furthermore, the catalyst used in the present invention is safe because it is a metal salt of an aromatic monocarboxylic acid, and also has the advantage of not requiring special care in its handling and storage.
次に実施例で本発明を説明する。 Next, the present invention will be explained with examples.
実施例 １
1lフラスコに温度計、空気吹込み管、滴下槽お
よび精留塔を配し、これにメチルメタクリレート
500ｇ（５モル）及びグリシド74ｇ（１モル）を
とり、これに重合禁止剤としてヒドロキノンモノ
メチルエーテル0.4ｇを添加した。ついで触媒と
して安息香酸カリウム2.72ｇ（0.017モル）を加
え、70〜80℃に加熱し、空気を微量吹込みなが
ら、減圧下（180〜250mmＨｇ）で生成してくるメ
タノールをメチルメタクリレートとの共沸により
連続的に留去した。反応中は反応系のモル比（メ
チルメタクリレート：グリシド）が４：１以下に
ならないように注意し、留去液量及び組成比を測
定してこれによりモル比が低下したならば滴下槽
からメチルメタクリレートを所定量加えた。反応
は２時間で完了した。ガスクロマトグラフイーに
よりグリシドの転化率は99％であることを確認し
た。反応完了後直ちに反応液を冷却し、ろ過によ
り触媒を回収し、ろ液を連続蒸留器にかけて過剰
のメチルメタクリレート（沸点100.8℃／760mmＨ
ｇ）を回収し、つづいて連続蒸留によりグリシジ
ルメタクリレート（沸点75℃／10mmＨｇ）を、
127.3ｇ（純度99.1％、収率89.5％）得た。Example 1 A thermometer, an air blowing pipe, a dropping tank, and a rectification column were arranged in a 1L flask, and methyl methacrylate was added to the flask.
500 g (5 mol) and 74 g (1 mol) of glycide were taken, and 0.4 g of hydroquinone monomethyl ether was added thereto as a polymerization inhibitor. Next, 2.72 g (0.017 mol) of potassium benzoate was added as a catalyst, heated to 70-80°C, and while blowing a small amount of air, the methanol produced was azeotropically produced under reduced pressure (180-250 mmHg) with methyl methacrylate. was continuously distilled off. During the reaction, be careful not to make the molar ratio of the reaction system (methyl methacrylate: glycide) less than 4:1. Measure the amount of distilled liquid and the composition ratio, and if the molar ratio decreases, remove methyl methacrylate from the dropping tank. A predetermined amount of methacrylate was added. The reaction was completed in 2 hours. The conversion rate of glycide was confirmed to be 99% by gas chromatography. Immediately after the reaction is completed, the reaction solution is cooled, the catalyst is recovered by filtration, and the filtrate is passed through a continuous distillation vessel to remove excess methyl methacrylate (boiling point 100.8℃/760mmH).
g) was collected, followed by continuous distillation to obtain glycidyl methacrylate (boiling point 75°C/10mmHg).
127.3g (purity 99.1%, yield 89.5%) was obtained.
実施例 ２
実施例１と同様にして、メチルメタクリレート
500ｇ（５モル）、グリシド74ｇ（１モル）、重合
禁止剤としてフエノチアジン0.5ｇ及び触媒とし
てサリチル酸カリウム5.29ｇ（0.03モル）を加え
て反応した。グリシジルメタクリレートの生成率
は、97％であつた。連続蒸留により131.4ｇのグ
リシジルメタクリレートを得た（純度98.5％、収
率92.4％）。Example 2 In the same manner as in Example 1, methyl methacrylate
500 g (5 moles), 74 g (1 mole) of glycide, 0.5 g of phenothiazine as a polymerization inhibitor, and 5.29 g (0.03 moles) of potassium salicylate as a catalyst were added for reaction. The production rate of glycidyl methacrylate was 97%. 131.4 g of glycidyl methacrylate was obtained by continuous distillation (purity 98.5%, yield 92.4%).
実施例 ３
実施例１と同様にして、メチルメタクリレート
400ｇ（４モル）、グリシド74ｇ（１モル）、重合
禁止剤としてヒドロキノン0.3ｇ及び触媒として
安息香酸カルシウム5.65ｇ（0.02モル）を加えて
反応した。グリシジルメタクリレートの生成率は
96.2％であり、連続蒸留により128.0ｇのグリシ
ジルメタクリレートを得た。（純度98.2％、収率
90％）。Example 3 In the same manner as in Example 1, methyl methacrylate
400 g (4 mol), 74 g (1 mol) of glycide, 0.3 g of hydroquinone as a polymerization inhibitor, and 5.65 g (0.02 mol) of calcium benzoate as a catalyst were added for reaction. The production rate of glycidyl methacrylate is
96.2%, and 128.0 g of glycidyl methacrylate was obtained by continuous distillation. (Purity 98.2%, yield
90%).
実施例 ４
実施例１と同様にして、メチルメタクリレート
500ｇ（５モル）、グリシド74ｇ（１モル）、重合
禁止剤としてフエノチアジン0.4ｇ及び触媒とし
てサリチル酸ナトリウム2.4ｇ（0.015モル）を加
えて反応した。Example 4 In the same manner as in Example 1, methyl methacrylate
500 g (5 moles), 74 g (1 mole) of glycide, 0.4 g of phenothiazine as a polymerization inhibitor, and 2.4 g (0.015 moles) of sodium salicylate as a catalyst were added for reaction.
グリシジルメタクリレートの生成率は96.5％で
あり、連続蒸留により127.5ｇのグリシジルメタ
クリレートを得た（純度98.8％、収率89.8％）。 The production rate of glycidyl methacrylate was 96.5%, and 127.5 g of glycidyl methacrylate was obtained by continuous distillation (purity 98.8%, yield 89.8%).
実施例 ５
実施例１と同様にしてメチルメタクリレート
500ｇ（５モル），グリシド74ｇ（１モル）、重合
禁止剤としてヒドロキノンモノメチルエーテル
0.4ｇ及び触媒として安息香酸マグネシウム2.67
ｇ（0.01モル）を加えて反応した。グリシジルメ
タクリレートの生成率は96％であり、連続蒸留に
より126.8ｇのグリシジルメタクリレートを得た
（純度98％、収率89.3％）。Example 5 Methyl methacrylate was prepared in the same manner as in Example 1.
500g (5 moles), glycide 74g (1 mole), hydroquinone monomethyl ether as a polymerization inhibitor
0.4g and magnesium benzoate 2.67 as catalyst
g (0.01 mol) was added and reacted. The production rate of glycidyl methacrylate was 96%, and 126.8 g of glycidyl methacrylate was obtained by continuous distillation (purity 98%, yield 89.3%).
Claims (1)
ートとグリシドとのエステル交換反応において、
触媒として芳香族モノカルボン酸のカリウム塩、
ナトリウム塩、マグネシウム塩またはカルシウム
塩を使用することを特徴とするグリシジルメタク
リレートまたはグリシジルアクリレートの製造
法。 ２ 触媒が安息香酸カリウムまたはサリチル酸カ
リウムである特許請求の範囲第１項記載の製造
法。[Claims] 1. In the transesterification reaction between methyl methacrylate or methyl acrylate and glycide,
Potassium salt of aromatic monocarboxylic acid as catalyst,
A method for producing glycidyl methacrylate or glycidyl acrylate, characterized by using a sodium salt, a magnesium salt or a calcium salt. 2. The production method according to claim 1, wherein the catalyst is potassium benzoate or potassium salicylate.
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 (en) | 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 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108707126B (en) * | 2018-07-03 | 2020-06-02 | 山东柳湾新材料有限公司 | Method for synthesizing glycidyl methacrylate by adopting microchannel reaction device |
-
1978
- 1978-06-14 JP JP7096378A patent/JPS54163513A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54163513A (en) | 1979-12-26 |
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