JPH0710799B2 - Method for producing methacrylic acid ester - Google Patents
Method for producing methacrylic acid esterInfo
- Publication number
- JPH0710799B2 JPH0710799B2 JP62020593A JP2059387A JPH0710799B2 JP H0710799 B2 JPH0710799 B2 JP H0710799B2 JP 62020593 A JP62020593 A JP 62020593A JP 2059387 A JP2059387 A JP 2059387A JP H0710799 B2 JPH0710799 B2 JP H0710799B2
- Authority
- JP
- Japan
- Prior art keywords
- acid ester
- reaction
- methacrylic acid
- catalyst
- methoxyisobutyrate
- 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 - Lifetime
Links
- 125000005397 methacrylic acid ester group Chemical group 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 21
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 16
- -1 β-methoxyisobutyric acid ester Chemical class 0.000 claims description 16
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 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)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明はメタクリル酸エステルの製造方法に関する。TECHNICAL FIELD The present invention relates to a method for producing a methacrylic acid ester.
メタクリル酸エステルはアクリル樹脂製品の主成分とし
て使用される。代表的なメタクリル酸エステルであるメ
タクリル酸メチルは透明で光沢が良く、電気絶縁性、耐
薬品性及び加工性に優れている。また、メタクリル酸エ
チル、メタクリル酸プロピル、メタクリル酸ブチル等
は、塗料、接着剤及び繊維処理剤等として有用な化合物
である。Methacrylic acid ester is used as the main component of acrylic resin products. Methyl methacrylate, which is a typical methacrylic acid ester, is transparent and has good gloss, and is excellent in electrical insulation, chemical resistance, and processability. In addition, ethyl methacrylate, propyl methacrylate, butyl methacrylate and the like are compounds useful as paints, adhesives, fiber treatment agents and the like.
既にβ‐メトキシイソ酪酸エステルを脱アルコールして
メタクリル酸エステルを製造する方法としては、硫酸を
用いる方法、アリールスルホン酸、p-トルエンスルホン
酸及びベンゼンスルホン酸を用いる方法（特開昭48-146
17号公報）が知られている。As a method of already dealcoholating β-methoxyisobutyric acid ester to produce a methacrylic acid ester, a method using sulfuric acid, a method using arylsulfonic acid, p-toluenesulfonic acid and benzenesulfonic acid (Japanese Patent Laid-Open No.
No. 17) is known.
しかしながら、硫酸を用いた場合は一般に分解及び副生
成物が生じ易く、そのために目的とするメタクリル酸エ
ステルの収率が低くなる欠点があり、この時多量の硫酸
を必要とする。またアリールスルホン酸、p-トルエンス
ルホン酸及びベンゼンスルホン酸を用いる場合は反応温
度が100〜170℃と高く、またこの場合も副生成物が生じ
易く目的とするメタクリル酸エステルの収率が低くなる
欠点がある。However, when sulfuric acid is used, decomposition and by-products are generally likely to occur, which results in a low yield of the target methacrylic acid ester, and a large amount of sulfuric acid is required at this time. When arylsulfonic acid, p-toluenesulfonic acid, and benzenesulfonic acid are used, the reaction temperature is as high as 100 to 170 ° C, and in this case also, a by-product is easily generated and the yield of the target methacrylic acid ester is low. There are drawbacks.
前述の欠点を解消する触媒として、ナトリウムメトキサ
イドまたはカリウムメトキサイドの使用が提案されてい
るが、しかし、これらの触媒も反応中、触媒活性が失活
し易く、必要となる触媒量が多くなるという欠点を有す
る。The use of sodium methoxide or potassium methoxide has been proposed as a catalyst for solving the above-mentioned drawbacks, but these catalysts also tend to lose their catalytic activity during the reaction, resulting in a large amount of the required catalyst. It has the drawback.
本発明者らは、触媒としてナトリウムメトキサイドまた
はカリウムメトキサイドを使用した場合の欠点を解消す
るために鋭意検討を重ねた結果、触媒を経時的に反応系
へ添加することにより、少量で長時間高い触媒活性を維
持でき、かつ副生成物の生成を抑えることができること
を見出し本発明を完成させるに至った。The present inventors have conducted extensive studies in order to eliminate the drawbacks when using sodium methoxide or potassium methoxide as a catalyst, and as a result, by adding the catalyst to the reaction system over time, a small amount for a long time. They have found that a high catalytic activity can be maintained and the production of by-products can be suppressed, and the present invention has been completed.
すなわち、本発明は 一般式（１） （式中、Ｒは炭素数１〜４のアルキル基を示す）で表さ
れる、β‐メトキシイソ酪酸エステルを脱アルコール
し、対応するメタクリル酸エステルを製造するに際し
て、触媒としてナトリウムメトキサイドまたはカリウム
メトキサイドを経時的に反応系へ添加しながら反応させ
ることを特徴とするメタクリル酸エステルの製造方法で
ある。That is, the present invention relates to the general formula (1) (Wherein R represents an alkyl group having 1 to 4 carbon atoms), the β-methoxyisobutyric acid ester is dealcoholated to produce a corresponding methacrylic acid ester, and sodium methoxide or potassium methoxide is used as a catalyst. The method for producing a methacrylic acid ester is characterized in that the reaction is carried out while adding side to the reaction system over time.
以下、本発明の方法を詳細に説明する。Hereinafter, the method of the present invention will be described in detail.
本発明の方法に用いられるβ‐メトキシイソ酪酸エステ
ルとしては、β‐メトキシイソ酪酸メチル、β‐メトキ
シイソ酪酸エチル、β‐メトキシイソ酪酸n-プロピル、
β‐メトキシイソ酪酸iso-プロピル、β‐メトキシイソ
酪酸n-ブチル、β‐メトキシイソ酪酸iso-ブチル及びβ
‐メトキシイソ酪酸t-ブチルがあり、これらのβ‐メト
キシイソ酪酸エステルを原料として対応するメタクリル
酸メチル、メタクリル酸エチル、メタクリル酸n-プロピ
ル、メタクリル酸iso-プロピル、メタクリル酸ｎ−ブチ
ル、メタクリル酸iso-ブチル及びメタクリル酸t-ブチル
を製造することができる。Examples of β-methoxyisobutyric acid ester used in the method of the present invention include methyl β-methoxyisobutyrate, ethyl β-methoxyisobutyrate, and n-propyl β-methoxyisobutyrate.
β-methoxyisobutyrate iso-propyl, β-methoxyisobutyrate n-butyl, β-methoxyisobutyrate iso-butyl and β
-T-Butyl methoxyisobutyrate, and corresponding β-methoxyisobutyric acid ester as a raw material, corresponding methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, iso-propyl methacrylate, n-butyl methacrylate, isomethacrylate -Butyl and t-butyl methacrylate can be produced.
本発明の方法に用いられる触媒は、ナトリウムメトキサ
イドまたはカリウムメトキサイドであり、これらの触媒
は高活性を有するものであるが、反応中次第に活性が低
下したり、使用量が多くなる欠点を有している。そこで
触媒の使用に際しては、反応系に経時的に添加して反応
を進めることが必要であり、その添加の方法は間欠的ま
たは連続的のいずれであってもよい。触媒は固体の状態
で添加することもできるが、より活性を高め、使用量を
減らすためには、溶媒に溶解して添加することが好まし
い。溶媒としてはメタノールが適当である。The catalyst used in the method of the present invention is sodium methoxide or potassium methoxide, and although these catalysts have high activity, they have the drawbacks that the activity gradually decreases during the reaction and the amount used increases. is doing. Therefore, when the catalyst is used, it is necessary to add it to the reaction system over time to advance the reaction, and the addition method may be either intermittent or continuous. The catalyst can be added in a solid state, but it is preferable to add it after dissolving it in a solvent in order to further enhance the activity and reduce the amount used. Methanol is suitable as the solvent.
これらの触媒を溶媒に溶解して用いた場合の使用量はβ
‐メトキシイソ酪酸エステルに対して0.1〜10重量％の
範囲であり、より好ましくは0.2〜５重量％の範囲であ
る。また触媒の添加は反応終了時まで続けてもよいが、
β‐メトキシイソ酪酸エステルの転化率が80％に達すれ
ば、反応は添加済触媒の活性で完了するので、この時点
で触媒の添加を終了してもよい。When these catalysts are dissolved in a solvent and used, the usage amount is β
It is in the range of 0.1 to 10% by weight, preferably 0.2 to 5% by weight, based on -methoxyisobutyric acid ester. The addition of the catalyst may be continued until the end of the reaction,
When the conversion rate of β-methoxyisobutyric acid ester reaches 80%, the reaction is completed by the activity of the added catalyst, and thus the addition of the catalyst may be terminated at this point.
本発明の方法において脱アルコール反応は常圧あるいは
減圧下で実施できる。反応温度は50〜150℃の範囲であ
り、より好ましくは60〜110℃の範囲である。In the method of the present invention, the dealcoholization reaction can be carried out under normal pressure or reduced pressure. The reaction temperature is in the range of 50 to 150 ° C, more preferably 60 to 110 ° C.
反応時間は使用する原料量、温度及び触媒量等によって
変わるが通常は0.5〜５時間である。The reaction time varies depending on the amount of raw material used, temperature, amount of catalyst, etc., but is usually 0.5 to 5 hours.
目的物であるメタクリル酸エステルは反応終了後、蒸留
等の常用の方法で得ることができるが、反応時に生成及
び添加したメタノール、メタクリル酸エステルを速やか
に連続的に留去し、その後蒸留等により精製する方法が
好ましい。After the completion of the reaction, the target methacrylic acid ester can be obtained by a conventional method such as distillation.However, methanol and methacrylic acid ester produced and added during the reaction are rapidly and continuously distilled off, and then distilled or the like. The method of purification is preferred.
本発明の方法によれば多量の硫酸を用いたり、反応を高
温で行うといった操作を必要とせず、温和な条件のもと
で短時間のうちに反応を進めることができる。また触媒
活性は他の触媒に比べて十分高く、触媒を反応開始時に
一括添加した場合に比べて、少量の触媒量で反応を速や
かに進行せしめることが可能である。According to the method of the present invention, it is possible to proceed the reaction in a short time under mild conditions without the need of using a large amount of sulfuric acid or performing the reaction at a high temperature. Further, the catalytic activity is sufficiently higher than that of other catalysts, and the reaction can be rapidly advanced with a small amount of the catalyst as compared with the case where the catalysts are added all at once at the start of the reaction.
更に、メタクリル酸を始めとする副生成物が殆ど生成す
ることなく、目的とするメタクリル酸エステルを高収率
で製造することができる。Further, the target methacrylic acid ester can be produced in a high yield with almost no generation of by-products such as methacrylic acid.
以下、実施例により本発明の方法を具体的に説明する。 Hereinafter, the method of the present invention will be specifically described with reference to examples.
実施例１ 撹拌機、温度計及び分留塔を備えた内容積500mlのフラ
スコにβ‐メトキシイソ酪酸メチル330g（2.5mol）を仕
込み、反応圧力400mmHgで撹拌しながら加熱した。系内
が安定したところで触媒としてナトリウムメトキサイド
の28重量％メタノール溶液をマイクロチューブポンプを
用いて反応系に連続的に添加した。ナトリウムメトキサ
イドの28重量％メタノール溶液の添加速度は16g/時間
で、2.5時間添加した。ナトリウムメトキサイドの総添
加量は11.2gであった。反応開始後、生成及び添加した
メタノール、メタクリル酸メチルを留出させた。反応は
３時間で終了し、次いで圧力を60mmHgまで減じ、残りの
メタクリル酸メチルを留出せしめた。Example 1 A flask having an internal volume of 500 ml equipped with a stirrer, a thermometer and a fractionation tower was charged with 330 g (2.5 mol) of methyl β-methoxyisobutyrate and heated at a reaction pressure of 400 mmHg with stirring. When the system became stable, a 28 wt% methanol solution of sodium methoxide as a catalyst was continuously added to the reaction system using a microtube pump. The 28% by weight sodium methoxide solution in methanol was added at a rate of 16 g / hour for 2.5 hours. The total amount of sodium methoxide added was 11.2 g. After the reaction was started, the produced and added methanol and methyl methacrylate were distilled. The reaction was completed in 3 hours, then the pressure was reduced to 60 mmHg and the remaining methyl methacrylate was distilled off.
反応で生成した副生成物は1.0gで、仕込みβ‐メトキシ
イソ酪酸メチルの0.3重量％であった。The by-product produced in the reaction was 1.0 g, which was 0.3% by weight of the charged methyl β-methoxyisobutyrate.
反応終了後、留出液を水洗浄を行い、その後300mmHgで
減圧蒸留し、目的のメタクリル酸メチル240.2gを得た。
β‐メトキシイソ酪酸メチル基準の収率は96％であっ
た。After completion of the reaction, the distillate was washed with water and then distilled under reduced pressure at 300 mmHg to obtain 240.2 g of the target methyl methacrylate.
The yield based on methyl β-methoxyisobutyrate was 96%.
実施例２〜４ 実施例１と同じ装置を使用し、同様な方法で原料のβ‐
メトキシイソ酪酸エステルの種類を変えて対応するメタ
クリル酸エステルを合成した結果を表１に示す。Examples 2 to 4 Using the same equipment as in Example 1 and using the same method as the raw material β-
Table 1 shows the results of synthesizing corresponding methacrylic acid esters by changing the type of methoxyisobutyric acid ester.
実施例５ 実施例１と同じ装置を使用し、β‐メトキシイソ酪酸メ
チル330g（2.5mol）を仕込み、反応圧力400mmHgで撹拌
しながら加熱した。系内が安定したところで触媒として
カリウムメトキサイドの28重量％メタノール溶液を実施
例１と同様に添加速度16g/時間で添加した。添加時間は
３時間で、カリウムメトキサイドの総添加量は13.4gで
あった。反応時間は４時間であった。Example 5 Using the same apparatus as in Example 1, 330 g (2.5 mol) of methyl β-methoxyisobutyrate was charged and heated at a reaction pressure of 400 mmHg with stirring. When the inside of the system was stabilized, a 28 wt% methanol solution of potassium methoxide was added as a catalyst at the addition rate of 16 g / hour as in Example 1. The addition time was 3 hours, and the total amount of potassium methoxide added was 13.4 g. The reaction time was 4 hours.
反応で生成した副生成物は、仕込みβ‐メトキシイソ酪
酸メチルの0.6重量％であった。The by-product produced in the reaction was 0.6% by weight of the charged methyl β-methoxyisobutyrate.
反応終了後、実施例１と同様に精製し、メタクリル酸メ
チル209.0gを得た。β‐メトキシイソ酪酸メチル基準の
収率は83.5％であった。After completion of the reaction, purification was carried out in the same manner as in Example 1 to obtain 209.0 g of methyl methacrylate. The yield based on methyl β-methoxyisobutyrate was 83.5%.
Claims (1)
れる、β‐メトキシイソ酪酸エステルを脱アルコール
し、対応するメタクリル酸エステルを製造するに際し
て、触媒としてナトリウムメトキサイドまたはカリウム
メトキサイドを経時的に反応系へ添加しながら反応させ
ることを特徴とするメタクリル酸エステルの製造方法。1. A general formula (1) (Wherein R represents an alkyl group having 1 to 4 carbon atoms), the β-methoxyisobutyric acid ester is dealcoholated to produce a corresponding methacrylic acid ester, and sodium methoxide or potassium methoxide is used as a catalyst. A method for producing a methacrylic acid ester, which comprises reacting while adding side to a reaction system with time.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62020593A JPH0710799B2 (en) | 1987-02-02 | 1987-02-02 | Method for producing methacrylic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62020593A JPH0710799B2 (en) | 1987-02-02 | 1987-02-02 | Method for producing methacrylic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63190855A JPS63190855A (en) | 1988-08-08 |
| JPH0710799B2 true JPH0710799B2 (en) | 1995-02-08 |
Family
ID=12031553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62020593A Expired - Lifetime JPH0710799B2 (en) | 1987-02-02 | 1987-02-02 | Method for producing methacrylic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0710799B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19548912A1 (en) * | 1995-12-27 | 1997-07-03 | Basf Ag | Process for the esterification of (meth) acrylic acid with an alkanol |
-
1987
- 1987-02-02 JP JP62020593A patent/JPH0710799B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63190855A (en) | 1988-08-08 |
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