JPS588042A - Distilling method of methyl acrylate - Google Patents
Distilling method of methyl acrylateInfo
- Publication number
- JPS588042A JPS588042A JP10622881A JP10622881A JPS588042A JP S588042 A JPS588042 A JP S588042A JP 10622881 A JP10622881 A JP 10622881A JP 10622881 A JP10622881 A JP 10622881A JP S588042 A JPS588042 A JP S588042A
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- methyl acrylate
- water
- methyl
- methyl alcohol
- 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
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 105
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 238000004821 distillation Methods 0.000 claims abstract description 17
- 238000005886 esterification reaction Methods 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- -1 furinol and octatool Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance 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
- 238000009835 boiling Methods 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
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229950000688 phenothiazine Drugs 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
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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
化反応によってえられる、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、水とともて同
伴される傾向のあっ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, methyl alcohol, which is obtained by the esterification reaction of acrylic acid and methyl alcohol,
The present invention relates to a distillation method for efficiently obtaining the target product, methyl acrylate, from an esterification reaction product consisting of acrylic acid, water, and methyl acrylate. 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 subsequent 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ってえられる。Methyl acrylate is obtained by an esterification reaction between acrylic acid and methyl alcohol.
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。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、複雑友
な工程や多量の１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 a large amount of water. It has the disadvantage that it cannot be used.
一方、上記親和性を抑えるだ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、キルンなどを
エステル化反応生成物に加工、エステル化によって生成
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、フリノールやオクタツールなどの高
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、１−かも、この操作も簡単で
ない場合が多い。On the other hand, an azeotropic agent that suppresses the above affinity and has a stronger affinity with water, such as benzene, toluene, kiln, etc., is processed into an esterification reaction product, and the water produced by esterification is removed from the system by azeotropy. Although this method is advantageous in esterification reactions with higher alcohols such as furinol and octatool, in the case of producing methyl acrylate from lower alcohols, methyl alcohol acrylic acid Due to the relatively low boiling point of methyl, separate additional operations (e.g. distillation) are required for separation from the entrainer, which is also often not simple.
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ットを提供する。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、アクリル酸、水お
よびアクリル酸メチル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重量ヂ、好ましくは、５〜
７重量係の範囲に調整する−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) When distilling a mixture substantially consisting of methyl alcohol, acrylic acid, water and methyl acrylate and distilling methyl acrylate together with water and methyl alcohol, methyl acrylate is introduced into the distillation column; The water content in the distillate is 3 to 8% by weight, preferably 5 to 8% by weight.
A method for distilling methyl acrylate, characterized in that a distillate substantially free of acrylic acid is obtained by adjusting the weight to a range of 7% by weight.
（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っ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.
（３） 当該混合物の組成が、メチルアルコール１〜
２０重量係、アクリル酸２５〜４５重量係、水５〜２０
重４４％およびアクリル酸メチル２５〜５０重量係の範
囲である上記（１）ま、そは（２）記載の方法。(3) The composition of the mixture is methyl alcohol 1 to
20 weight ratio, acrylic acid 25-45 weight ratio, water 5-20
The method according to (1) or (2) above, wherein the weight is 44% and the methyl acrylate content is in the range of 25 to 50% by weight.
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っ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かえられる。The mixture essentially consisting of methyl alcohol, acrylic acid, water and methyl acrylate specified by the present invention is obtained by an esterification reaction of acrylic acid and methyl alcohol, for example, 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 containing a large amount of water and a large amount of acrylic acid as defined in (3) above can be obtained.
蒸留は通常の条件によって行われる。すなわち、理論段
数５〜２０段、圧力２ ０ ０ 〜２ ０ ０ ０ ｍ
ｉＨｇ（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
、ノ・イドロキノン、ノ・イドロキノンモノメチルエー
テル、フェノチアジンなどの重合防止剤が５〜５０００
ｐｐｍ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 m
iHg (absolute pressure), tower top temperature 40 to 100°C, and tower bottom temperature 60 to 130°C. In order to prevent polymerization in the tower, a polymerization inhibitor such as no-hydroquinone, no-hydroquinone monomethyl ether, or phenothiazine is added at 5 to 5,000 ml.
It is added in a ppm range.
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
りなルモ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
係、好ましくは５〜７重量重量節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, the remaining 5% by weight being water and Alcohol, such as methyl alcohol, can also be used satisfactorily. 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, 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
物かえられ、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える。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。Thus, the methyl alcohol, water and methyl acrylate mixture is returned as a substantially acrylic acid-free fraction, from which the methyl alcohol, water is easily removed to yield methyl acrylate. On the other hand, the supplied acrylic acid is substantially retained in the bottom liquid part of the distillation column.
In addition, some methyl alcohol, water, and methyl acrylate may remain. This bottom liquid can be subjected to the esterification reaction again.
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
るように々す、こればアク゛リル酸をも同伴して留出せ
しめる蒸気組成となってしまうのである。逆に多すきる
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きず、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。It is important to control the water content in the distillate distillate within the above range. For example, if the input amount of methyl acrylate is too small, the water content of the distillate should exceed 8% by weight, resulting in a vapor composition that allows acrylic acid to be distilled out as well. It's put away. On the other hand, it is preferable to use too much acrylic acid, which does not entrain acrylic acid and only reduces the water content in the distillate, but this would result in useless distillation of methyl acrylate and is economically disadvantageous. Moreover, since the polymerizable substance called methyl acrylate is needlessly exposed to high temperatures, it is better to minimize the amount of the polymerizable substance 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。Hereinafter, the present invention will be explained in more detail with reference to Examples and Comparative Examples.
実施例１
容量１１の釜をもった３２ｍ＋＊内径、１０段の多孔板
蒸留塔に、メチルアルコール７、♀％（重量％、以下同
様）、アクリル酸３５，６％、水１４．７チ、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１５００ ｇｒ／Ｈｒで供
給し、塔頂付近よジノ・イドロキノンを０．０２％含む
アクリル酸メチルを６００ｇ ｒ ／Ｈｒで供給し、常
圧で蒸留を行った。塔頂より留出液１２００ ｇ ｒ／
Ｈｒをえた。この留出液の組成ハ、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％以下であった。こ
の時の塔頂温域は６９”′Ｃ１釜温度は１０２℃であっ
た。Example 1 In a 32 m+* inner diameter, 10-stage perforated plate distillation column having a pot with a capacity of 11, methyl alcohol 7%♀% (weight%, hereinafter the same), acrylic acid 35.6%, water 14.7%, An esterification reaction product consisting of 42.1% methyl acrylate and 0.1% hydroquinone was fed at 1500 gr/Hr, and 600 g r/Hr of methyl acrylate containing 0.02% dinohydroquinone was fed near the top of the column. Distillation was carried out at normal pressure. 1200 g r/distillate from the top of the column
I got an hour. The composition of this distillate is: methyl alcohol 6
．． 7%, water 7.5% and methyl acrylate 85.8%
The content of acrylic acid was 0.0005% or less. At this time, the tower top temperature range was 69'''C1 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ｌ ５００ｇｒｌＨｒで供給し１、
塔頂付近より、ハイドロキノンを０．０２係含むアクリ
ル酸メチルを４５８ ｇｒ／Ｈｒで供給し蒸留を行った
。塔頂より留出液１０５８．５ ｇ ｒ／Ｈｒをえた。Comparative Example 1 Using the same equipment and operation as in Example 1, an esterification reaction product of the same composition was fed at 1 500 grlHr.
Methyl acrylate containing 0.02 parts of hydroquinone was supplied from near the top of the column at 458 gr/Hr for distillation. A distillate of 1058.5 g r/hr was obtained from the top of the column.
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８３９５％であり、アク
リル酸００４７％を含んでいた。この時の塔頂温度は７
０℃、釜温度は１０２℃であった。The composition of this distillate is 7.5% methyl alcohol and 8% water.
．． 5% and 8395% methyl acrylate, and contained 0047% acrylic acid. At this time, the tower top temperature was 7
The temperature of the pot 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３６２％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１５００ｇｒβｒ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５６８ ｇ ｒ／Ｈｒで供給し
蒸留を行った。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 362% and hydroquinone 0.1
% of the esterification reaction product was fed at 1500 gr
Distillation was carried out by supplying methyl acrylate containing 568 g r/Hr.
塔頂より留出液ｔ１６８ｇｒ／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％以下であった。この時の塔頂温度は６８
．５℃、釜温度は９８°Ｃであった。A distillate of 168 gr/Hr was obtained from the top of the column. The composition of this distillate was 19.6% methyl alcohol, 5.5% water, and 74.9% methyl acrylate, with acrylic acid being 0.0005% or less. 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１５００ ｇ
ｒ／Ｈｒで供給し、塔頂付近よりノ・イドロキノンを０
．０２％含むアクリ、！し酸メチル１５６ ｇｒ／Ｈｒ
を供給し、蒸留を行った。塔頂より留出液７５８．３
ｇｒ／Ｈｒをえた０この留出液の組成はメチルアルコー
ル３０．１％、水８．５チおよびアクリル酸メチル６１
．１ ％であり、アクリル酸は０．３％であった。この
時の塔頂温度は７０℃、釜温凌は９８°Ｃであった。Comparative Example 2 Using the same equipment and operation as in Example 1, 1500 g of an esterification reaction product having the same composition as in Example 2 was prepared.
r/Hr, and 0 hydroquinone from near the top of the tower.
．． Acrylic containing 02%! Methyl phosphate 156 gr/Hr
was supplied and distilled. Distillate from the top of the column 758.3
The composition of this distillate was 30.1% methyl alcohol, 8.5% water, and 61% methyl acrylate.
．． 1%, and acrylic acid was 0.3%. At this time, the tower top temperature was 70°C, and the pot temperature was 98°C.
Claims (3)
水およびアクリル酸メチルよりなる混合物を蒸留シ、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重量重量節囲に調整す
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) Substantially methyl alcohol, acrylic acid,
When distilling a mixture of water and methyl acrylate and distilling methyl acrylate together with water and methyl alcohol, methyl acrylate is charged into the distillation column and the water content in the distillate is adjusted to 3 to 8% by weight. A method for distilling methyl acrylate, characterized in that a distillate containing substantially no acrylic acid is obtained by adjusting the volume to a certain degree.
ルとのエステル化反応によってえられたものである特許
請求の範囲（１）記載の方法。(2) The method according to claim (1), wherein the mixture is obtained by an esterification reaction of acrylic acid and methyl alcohol.
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−の範囲
である特許請求の範囲（１）または（２）記載の方法。(3) The composition of the mixture is methyl alcohol 1 to
20% by weight, 25-45% by weight of acrylic acid, 5-20% by weight of water
% by weight and methyl acrylate ranges from 25 to 50% by weight.
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 |
| FR8211987A FR2509294A1 (en) | 1981-07-09 | 1982-07-08 | PROCESS FOR PRODUCING ESTERS OF ACRYLIC ACID OR METHACRYLIC ACID |
| MX193511A MX163005B (en) | 1981-07-09 | 1982-07-08 | IMPROVED PROCEDURE FOR PRODUCING AN ACRYLIC OR METHACRYL ESTER |
| 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 true JPS588042A (en) | 1983-01-18 |
| JPS6320416B2 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 |
|---|---|---|---|---|
| JPS59181239A (en) * | 1983-03-30 | 1984-10-15 | Mitsubishi Rayon Co Ltd | Method for producing fluorine-containing acrylic ester or methacrylic ester |
Families Citing this family (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 |
-
1981
- 1981-07-09 JP JP10622881A patent/JPS588042A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59181239A (en) * | 1983-03-30 | 1984-10-15 | Mitsubishi Rayon Co Ltd | Method for producing fluorine-containing acrylic ester or methacrylic ester |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6320416B2 (en) | 1988-04-27 |
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