JPS6320416B2 - - Google Patents
Info
- Publication number
- JPS6320416B2 JPS6320416B2 JP10622881A JP10622881A JPS6320416B2 JP S6320416 B2 JPS6320416 B2 JP S6320416B2 JP 10622881 A JP10622881 A JP 10622881A JP 10622881 A JP10622881 A JP 10622881A JP S6320416 B2 JPS6320416 B2 JP S6320416B2
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- methyl acrylate
- water
- methyl alcohol
- methyl
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 87
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 86
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 34
- 238000005886 esterification reaction Methods 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 13
- 239000007795 chemical reaction product Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 5
- 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
- 230000000052 comparative effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- -1 butanol and octanol Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N monomethylhydroquinone Natural products CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、アクリル酸メチルの蒸留方法に関す
る。詳しく述べるとアクリル酸とメチルアルコー
ルとのエステル化反応によつてえられる、主とし
てメチルアルコール、アクリル酸、水およびアク
リル酸メチルよりなるエステル化反応生成物か
ら、目的物であるアクリル酸メチルを効率よく取
得するための蒸留方法に関する。とくに本発明
は、当該アクリル酸メチルを、水およびメチルア
ルコールとともに留出せしめるに際し、従来、水
とともに同伴される傾向のあつたアクリル酸を実
質的に同伴させない蒸留方法を提供することによ
り、以後のアクリル酸メチルの精製工程を大巾に
簡略化することを目的とする。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for distilling methyl acrylate. Specifically, the target product, methyl acrylate, can be efficiently obtained from the esterification reaction product mainly consisting of methyl alcohol, acrylic acid, water, and methyl acrylate, which is obtained by the esterification reaction of acrylic acid and methyl alcohol. Regarding the distillation method for obtaining. In particular, the present invention provides a distillation method in which acrylic acid, which conventionally tends to be entrained with water, is not substantially entrained when the methyl acrylate is distilled together with water and methyl alcohol. The purpose is to greatly simplify the purification process of methyl acrylate.
アクリル酸メチルは、アクリル酸とメチルアル
コールとのエステル化反応によつてえられる。こ
の反応は平衡反応であり、えられる反応生成物中
には、アクリル酸メチルのほかに、未反応のメチ
ルアルコールやアクリル酸およびかなりの量の生
成水とが共存している。 Methyl acrylate is obtained by an esterification reaction between acrylic acid and methyl alcohol. This reaction is an equilibrium reaction, and in addition to methyl acrylate, unreacted methyl alcohol, acrylic acid, and a considerable amount of produced water coexist in the reaction product obtained.
従来は、このような反応生成物より、アクリル
酸メチル、メチルアルコールおよび水を分離する
ために蒸留処理すると、水とアクリル酸との親和
性が強く、蒸留段数や還流比を上げても、水とと
もにアクリル酸が不可避的に同伴留出し、結果的
には、このアクリル酸は、エステル化反応の収率
損を招く一因ともなり、また、留出したメチルア
ルコール、水およびアクリル酸メチルの混合物中
に、アクリル酸が含まれると留出液を再び蒸留処
理したり、中和、水洗などの処理でアクリル酸を
除去しなければならず、複雑な工程や多量の廃水
を発生させざるをえない欠点を有する。 Conventionally, when distillation treatment was performed to separate methyl acrylate, methyl alcohol, and water from such reaction products, the affinity between water and acrylic acid was strong, and even if the number of distillation stages and reflux ratio were increased, water was not removed. At the same time, acrylic acid is inevitably distilled out along with it, and as a result, this acrylic acid contributes to the loss of yield in the esterification reaction, and also causes a mixture of distilled methyl alcohol, water, and methyl acrylate. If acrylic acid is contained in the distillate, the distillate must be distilled again, or the acrylic acid must be removed by neutralization, water washing, etc., resulting in complicated processes and the generation of large amounts of wastewater. Has no drawbacks.
一方、上記親和性を抑えるため水との親和性が
より強い共沸剤、たとえば、ベンゼン、トルエ
ン、キシレンなどをエステル化反応生成物に加
え、エステル化によつて生成した水分を共沸によ
り系外に留去することも知られているが、この方
法は、ブタノールやオクタノールなどの高級アル
コールとのエステル化反応において有利ではある
ものの、低級アルコールからのアクリル酸メチル
製造の場合は、メチルアルコール、アクリル酸メ
チルの沸点が比較的低く、共沸剤との分離の点で
別の付加的操作（たとえば蒸留）が必要となり、
しかも、この操作も簡単でない場合が多い。 On the other hand, in order to suppress the above affinity, an azeotropic agent with stronger affinity for water, such as benzene, toluene, xylene, etc., is added to the esterification reaction product, and the water produced by esterification is azeotropically distilled. Although this method is advantageous in esterification reactions with higher alcohols such as butanol and octanol, when producing methyl acrylate from lower alcohols, methyl alcohol The boiling point of methyl acrylate is relatively low and separate additional operations (e.g. distillation) are required for separation from the entrainer;
Moreover, this operation is often not easy.
本発明は、メチルアルコールおよびアクリル酸
とのエステル化反応生成物より、水およびアクリ
ル酸メチルを効果的に留出せしめるに際し、実質
的にアクリル酸を同伴せしめない方法を提供する
ことを目的とする。かくして、アクリル酸を実質
的に缶液側に残留せしめえたために、本発明の方
法は、留出せしめてえられる、メチルアルコー
ル、水およびアクリル酸メチルを主体とする混合
物のアクリル酸メチル取得という以降のプロセス
がきわめて簡素化されるというメリツトを提供す
る。 An object of the present invention is to provide a method for effectively distilling water and methyl acrylate from an esterification reaction product of methyl alcohol and acrylic acid without substantially entraining acrylic acid. . In this way, since the acrylic acid was substantially left in the tank liquid side, the method of the present invention can be used to obtain methyl acrylate from a mixture mainly consisting of methyl alcohol, water and methyl acrylate obtained by distillation. This provides the advantage that subsequent processes are extremely simplified.
本発明は、以下の如く特定しうる。 The present invention can be specified as follows.
(1) 実質的にメチルアルコール１〜20重量％、ア
クリル酸25〜45重量％、水５〜20重量％および
アクリル酸メチル25〜50重量％よりなる混合物
を蒸留し、アクリル酸メチルを水およびメチル
アルコールとともに留出せしめるに際し、アク
リル酸メチルを当該蒸留塔に投入し、留出液中
の水含量を３〜８重量％の範囲に調整すること
により実質的にアクリル酸を含有しない留出液
をえることを特徴とするアクリル酸メチルの蒸
留方法。(1) A mixture consisting essentially of 1 to 20% by weight of methyl alcohol, 25 to 45% by weight of acrylic acid, 5 to 20% by weight of water, and 25 to 50% by weight of methyl acrylate is distilled, and the methyl acrylate is dissolved in water and When distilling together with methyl alcohol, methyl acrylate is charged into the distillation column and the water content in the distillate is adjusted to a range of 3 to 8% by weight, thereby producing a distillate that does not substantially contain acrylic acid. A method for distilling methyl acrylate, characterized in that it yields.
(2) 当該混合物がアクリル酸とメチルアルコール
とのエステル化反応によつてえられたものであ
る上記(1)記載の方法。(2) The method according to (1) above, wherein the mixture is obtained by an esterification reaction between acrylic acid and methyl alcohol.
本発明が特定する実質的にメチルアルコール、
アクリル酸、水およびアクリル酸メチルよりなる
混合物は、たとえば上記(2)記載のように、アクリ
ル酸とメチルアルコールとのエステル化反応によ
つてえられるものである。反応によりえられる反
応混合物の組成としては、エステル化反応に使用
する触媒、反応温度、圧力、反応時間等反応条件
およびプロセスの違いにより異るが、メチルアル
コールのアクリル酸に対するモル比が３以下とい
うアルコール分の比較的低い領域でエステル化反
応せしめることにより、上記(3)で規定したごとき
水分の多い、また、アクリル酸の多い反応混合物
がえられる。 Substantially methyl alcohol as specified by the present invention,
A mixture of acrylic acid, water and methyl acrylate is obtained, for example, by an esterification reaction between acrylic acid and methyl alcohol, as described in (2) above. The composition of the reaction mixture obtained by the reaction varies depending on the reaction conditions and process, such as the catalyst used in the esterification reaction, reaction temperature, pressure, and reaction time, but the molar ratio of methyl alcohol to acrylic acid is 3 or less. By carrying out the esterification reaction in a relatively low alcohol content region, a reaction mixture rich in water and rich in acrylic acid as defined in (3) above can be obtained.
蒸留は通常の条件によつて行われる。すなわ
ち、理論段数５〜20段、圧力200〜2000mmHg（絶
対圧）、塔頂温度40〜100℃、塔底温度60〜130℃
である。塔内での重合を防止するために、ハイド
ロキノン、ハイドロキノンモノメチルエーテル、
フエノチアジンなどの重合防止剤が５〜5000ppm
の範囲で添加される。 Distillation is carried out under conventional conditions. That is, the number of theoretical plates is 5 to 20, the pressure is 200 to 2000 mmHg (absolute pressure), the top temperature is 40 to 100°C, and the bottom temperature is 60 to 130°C.
It is. Hydroquinone, hydroquinone monomethyl ether,
Polymerization inhibitor such as phenothiazine is 5 to 5000 ppm
It is added within the range of
蒸留塔に投入されるアクリル酸メチルとして
は、実質的にアクリル酸メチルよりなるものが好
ましいが、95重量％以上の純度のもの、たとえ
ば、95重量％アクリル酸メチル、残り５重量％が
水およびメチルアルコールよりなるものも十分使
用しうる。アクリル酸メチルの投入量は、留出液
中の水分が上記特定になる、３〜８重量％、好ま
しくは５〜７重量％の範囲に維持されるように調
節される。 The methyl acrylate fed into the distillation column is preferably one consisting essentially of methyl acrylate, but one with a purity of 95% by weight or more, for example, 95% by weight methyl acrylate and the remaining 5% by weight water and methyl acrylate. Those made of methyl alcohol may also be used. The amount of methyl acrylate added is adjusted so that the water content in the distillate is maintained within the above specified range of 3 to 8% by weight, preferably 5 to 7% by weight.
かくして、実質的に、アクリル酸が含まれない
留分として、メチルアルコール、水およびアクリ
ル酸メチル混合物がえられ、これから、メチルア
ルコール、水が容易に除かれて、アクリル酸メチ
ルを得る。一方、蒸留塔の缶液部には、供給され
たアクリル酸が実質的に保留され、その他、メチ
ルアルコール、水およびアクリル酸メチルが一部
残留することもある。この缶液は再びエステル化
反応に供することができる。蒸留塔留出液中の水
分を上記の範囲に調節することは重要である。た
とえばアクリル酸メチル投入量が少な過ぎたとき
は、留出液中の水分が８重量％を越える組成をと
るようになり、これはアクリル酸をも同伴して留
出せしめる蒸気組成となつてしまうのである。逆
に多すぎることは、アクリル酸を同伴することは
ないし留出液中の水分が減るだけではあるもの
の、これではアクリル酸メチルの無益な蒸留を行
うにすぎず、経済的に不利であるばかりか、アク
リル酸メチルという重合性物質を無駄に高温にさ
らすこととなるので、その投入量は出来るだけ少
なくするのがよいことになる。 Thus, a mixture of methyl alcohol, water and methyl acrylate is obtained as a fraction substantially free of acrylic acid, from which methyl alcohol and water are easily removed to obtain methyl acrylate. On the other hand, the supplied acrylic acid is substantially retained in the bottom liquid portion of the distillation column, and in addition, methyl alcohol, water, and methyl acrylate may partially remain. This bottom liquid can be subjected to the esterification reaction again. It is important to control the water content in the distillate distillate within the above range. For example, if the amount of methyl acrylate input is too small, the distillate will have a water content of more than 8% by weight, resulting in a vapor composition that will cause acrylic acid to be distilled out as well. It is. On the other hand, too much acrylic acid will not entrain acrylic acid and will only reduce the water content in the distillate, but this will only result in useless distillation of methyl acrylate, which is economically disadvantageous. Otherwise, the polymerizable substance called methyl acrylate is needlessly exposed to high temperatures, so it is better to minimize the amount of acrylate added.
本発明はかくして工業的に有利に実施される。 The present invention can thus be carried out industrially with advantage.
以下、実施例および比較例にて、本発明をさら
に詳しく説明する。 The present invention will be explained in more detail below using Examples and Comparative Examples.
実施例 １
容量１の釜をもつた32mm内径、10段の多孔板
蒸留塔に、メチルアルコール7.5％（重量％、以
下同様）、アクリル酸35.6％、水14.7％、アクリ
ル酸メチル42.1％およびハイドロキノン0.1％よ
りなるエステル化反応生成物を1500gr／Hrで供
給し、塔頂付近よりハイドロキノンを0.02％含む
アクリル酸メチルを600gr／Hrで供給し、常圧で
蒸留を行つた。塔頂より留出液1200gr／Hrをえ
た。この留出液の組成は、メチルアルコール6.7
％、水7.5％およびアクリル酸メチル85.8％であ
り、アクリル酸は0.0005％以下であつた。この時
の塔頂温度は69℃、釜温度は102℃であつた。Example 1 In a 32 mm inner diameter, 10-stage perforated plate distillation column having a pot with a capacity of 1, 7.5% methyl alcohol (by weight, the same applies hereinafter), 35.6% acrylic acid, 14.7% water, 42.1% methyl acrylate, and hydroquinone were added. An esterification reaction product containing 0.1% was fed at a rate of 1500gr/Hr, and methyl acrylate containing 0.02% hydroquinone was fed from near the top of the column at a rate of 600gr/Hr, followed by distillation at normal pressure. 1200gr/hr of distillate was obtained from the top of the column. The composition of this distillate is methyl alcohol 6.7
%, water 7.5% and methyl acrylate 85.8%, and acrylic acid was less than 0.0005%. At this time, the tower top temperature was 69°C and the pot temperature was 102°C.
比較例 １
実施例１と同じ装置および操作により、同じ組
成のエステル化反応生成物を1500gr／Hrで供給
し、塔頂付近より、ハイドロキノンを0.02％含む
アクリル酸メチルを458gr／Hrで供給し蒸留を行
つた。塔頂より留出液1058.5gr／Hrをえた。こ
の留出液の組成は、メチルアルコール7.5％、水
8.5％およびアクリル酸メチル83.95％であり、ア
クリル酸0.047％を含んでいた。この時の塔頂温
度は70℃、釜温度は102℃であつた。Comparative Example 1 Using the same equipment and operation as in Example 1, an esterification reaction product of the same composition was fed at 1500gr/Hr, and methyl acrylate containing 0.02% hydroquinone was fed from near the top of the column at 458gr/Hr for distillation. I went there. A distillate of 1058.5gr/hr was obtained from the top of the column. The composition of this distillate is 7.5% methyl alcohol, water
8.5% and 83.95% methyl acrylate, and contained 0.047% acrylic acid. At this time, the tower top temperature was 70°C and the pot temperature was 102°C.
実施例 ２
実施例１と同じ装置および操作により、メチル
アルコール18.9％、アクリル酸32.3％、水12.5％、
アクリル酸メチル36.2％およびハイドロキノン
0.1％よりなるエステル化反応生成物を1500gr／
Hrで供給し、一方塔頂付近よりハイドロキノン
を0.02％含むアクリル酸メチルを568gr／Hrで供
給し蒸留を行つた。塔頂より留出液1168gr／Hr
をえた。この留出液の組成は、メチルアルコール
19.6％、水5.5％およびアクリル酸メチル74.9％で
あり、アクリル酸は0.0005％以下であつた。この
時の塔頂温度は68.5℃、釜温度は98℃であつた。Example 2 Using the same equipment and operation as in Example 1, 18.9% methyl alcohol, 32.3% acrylic acid, 12.5% water,
Methyl acrylate 36.2% and hydroquinone
1500gr of esterification reaction product consisting of 0.1%
At the same time, methyl acrylate containing 0.02% hydroquinone was fed from near the top of the column at a rate of 568 gr/Hr for distillation. Distillate 1168gr/Hr from the top of the tower
I got it. The composition of this distillate is methyl alcohol
19.6%, water 5.5% and methyl acrylate 74.9%, and acrylic acid was less than 0.0005%. At this time, the tower top temperature was 68.5°C and the pot temperature was 98°C.
比較例 ２
実施例１と同じ装置および操作により、実施例
２におけると同じ組成のエステル化反応生成物を
1500gr／Hrで供給し、塔頂付近よりハイドロキ
ノンを0.02％含むアクリル酸メチル156gr／Hrを
供給し、蒸留を行つた。塔頂より留出液
758.3gr／Hrをえた。この留出液の組成はメチル
アルコール30.1％、水8.5％およびアクリル酸メ
チル61.1％であり、アクリル酸は0.3％であつた。
この時の塔頂温度は70℃、釜温度は98℃であつ
た。Comparative Example 2 Using the same equipment and operation as in Example 1, an esterification reaction product with the same composition as in Example 2 was produced.
Distillation was carried out by feeding 1500gr/Hr of methyl acrylate containing 0.02% hydroquinone from near the top of the column. Distillate from the top of the tower
Earned 758.3gr/Hr. The composition of this distillate was 30.1% methyl alcohol, 8.5% water, and 61.1% methyl acrylate, with 0.3% acrylic acid.
At this time, the tower top temperature was 70°C and the pot temperature was 98°C.
Claims (1)
クリル酸25〜45重量％、水５〜20重量％およびア
クリル酸メチル25〜50重量％よりなる混合物を蒸
留し、アクリル酸メチルを水およびメチルアルコ
ールとともに留出せしめるに際し、アクリル酸メ
チルを当該蒸留塔に投入し、留出液中の水含量を
３〜８重量％の範囲に調整することにより実質的
にアクリル酸を含有しない留出液をえることを特
徴とするアクリル酸メチルの蒸留方法。 ２ 当該混合物がアクリル酸とメチルアルコール
とのエステル化反応によつてえられたものである
特許請求の範囲１記載の方法。[Claims] 1. A mixture consisting essentially of 1 to 20% by weight of methyl alcohol, 25 to 45% by weight of acrylic acid, 5 to 20% of water and 25 to 50% by weight of methyl acrylate is distilled to obtain acrylic acid. When distilling methyl together with water and methyl alcohol, methyl acrylate is charged into the distillation column and the water content in the distillate is adjusted to a range of 3 to 8% by weight, thereby substantially containing acrylic acid. A method for distilling methyl acrylate, characterized by obtaining a distillate with no 2. The method according to claim 1, wherein the mixture is obtained by an esterification reaction between acrylic acid and methyl alcohol.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10622881A JPS588042A (en) | 1981-07-09 | 1981-07-09 | Distilling method of methyl acrylate |
| US06/393,484 US4464229A (en) | 1981-07-09 | 1982-06-29 | Process for producing acrylic or methacrylic esters |
| MX193511A MX163005B (en) | 1981-07-09 | 1982-07-08 | IMPROVED PROCEDURE FOR PRODUCING AN ACRYLIC OR METHACRYL ESTER |
| FR8211987A FR2509294A1 (en) | 1981-07-09 | 1982-07-08 | PROCESS FOR PRODUCING ESTERS OF ACRYLIC ACID OR METHACRYLIC ACID |
| BR8203983A BR8203983A (en) | 1981-07-09 | 1982-07-08 | PROCESS TO PRODUCE ACRYLIC OR METACRYLIC ESTER |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10622881A JPS588042A (en) | 1981-07-09 | 1981-07-09 | Distilling method of methyl acrylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS588042A JPS588042A (en) | 1983-01-18 |
| JPS6320416B2 true JPS6320416B2 (en) | 1988-04-27 |
Family
ID=14428264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10622881A Granted JPS588042A (en) | 1981-07-09 | 1981-07-09 | Distilling method of methyl acrylate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS588042A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63144505A (en) * | 1986-12-09 | 1988-06-16 | Mitsubishi Electric Corp | Magnetic field leakage canceling device |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59181239A (en) * | 1983-03-30 | 1984-10-15 | Mitsubishi Rayon Co Ltd | Production of fluorine-containing acrylic or methacrylic ester |
-
1981
- 1981-07-09 JP JP10622881A patent/JPS588042A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63144505A (en) * | 1986-12-09 | 1988-06-16 | Mitsubishi Electric Corp | Magnetic field leakage canceling device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS588042A (en) | 1983-01-18 |
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