JP3332341B2 - Method for producing acid chloride - Google Patents
Method for producing acid chlorideInfo
- Publication number
- JP3332341B2 JP3332341B2 JP06108298A JP6108298A JP3332341B2 JP 3332341 B2 JP3332341 B2 JP 3332341B2 JP 06108298 A JP06108298 A JP 06108298A JP 6108298 A JP6108298 A JP 6108298A JP 3332341 B2 JP3332341 B2 JP 3332341B2
- Authority
- JP
- Japan
- Prior art keywords
- acid chloride
- phosphorus trichloride
- distillation
- acid
- aliphatic carboxylic
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、着色の少ない酸ク
ロライドを製造する方法に関する。[0001] The present invention relates to a method for producing a less colored acid chloride.
【０００２】[0002]
【従来の技術】（メタ）アクリル酸クロライド等の酸ク
ロライドは、アシル化剤として有用であり、対象化合物
が有する水酸基、アミノ基、芳香核などの水素をアシル
基で置換することが出来る。しかも、（メタ）アクリル
酸クロライドのような反応性に富んだ二重結合を有する
酸クロライドは、前記対象化合物に反応性二重結合を導
入することもできるため、極めて有用である。2. Description of the Related Art Acid chlorides such as (meth) acrylic acid chloride are useful as acylating agents and can substitute hydrogen such as a hydroxyl group, an amino group or an aromatic nucleus of a target compound with an acyl group. Moreover, an acid chloride having a double bond with high reactivity such as (meth) acrylic acid chloride is extremely useful because a reactive double bond can be introduced into the target compound.
【０００３】この反応で得られた生成物は、主として各
種の機能性高分子の原料や医薬・農薬・殺虫剤等の原料
または中間体として重要である。酸クロライドを合成す
る方法として、従来、飽和または不飽和の脂肪族カルボ
ン酸と各種のリン化合物、チオニルクロライドまたはホ
スゲンとを反応させる方法が知られている。これらの方
法のうち、チオニルクロライド法は、副生する塩化水素
と亜硫酸ガスの処理にコストがかかる上に生成物への硫
黄化合物の混入が避けられないし、ホスゲン法は、反応
性が低いために高価な触媒を用いなければならず、しか
もホスゲンそのものの毒性の問題もあり、いずれも工業
的には優れた方法とはいいがたい。これに対し、三塩化
リン法は、原料価格的に有利であり、副生するリン化合
物は比較的容易に有用な無機リン化合物に変換再利用で
き、資源の有効利用の面からも好ましい方法である。The products obtained by this reaction are important mainly as raw materials for various functional polymers, raw materials or intermediates for pharmaceuticals, agricultural chemicals, insecticides and the like. As a method of synthesizing an acid chloride, a method of reacting a saturated or unsaturated aliphatic carboxylic acid with various phosphorus compounds, thionyl chloride or phosgene is conventionally known. Of these methods, the thionyl chloride method is expensive in treating by-produced hydrogen chloride and sulfur dioxide gas, and inevitably involves the incorporation of sulfur compounds into the product, and the phosgene method has low reactivity. Expensive catalysts must be used, and there is also the problem of toxicity of phosgene itself. Therefore, none of these methods is industrially excellent. On the other hand, the phosphorus trichloride method is advantageous in terms of raw material price, and a phosphorus compound produced as a by-product can be relatively easily converted and reused into a useful inorganic phosphorus compound, and is a preferable method from the viewpoint of effective use of resources. is there.
【０００４】この三塩化リン法を具体的に説明すれば、
従来は、（メタ）アクリル酸等の脂肪族カルボン酸と三
塩化リンを反応させてクロライドを高収率かつ効率よく
製造するために、得られた酸クロライドを単蒸留精製に
より得るようにしていた。具体的には、（メタ）アクリ
ル酸のような反応性二重結合を有する脂肪族カルボン酸
の場合にはパラメトキシフェノール（ＭＥＨＱ）のよう
な重合防止剤を添加しておいて、脂肪族カルボン酸に三
塩化リンを加えて反応させたのち、単蒸留を行い、酸ク
ロライドを留出分として得るのである。[0004] The phosphorus trichloride method is specifically described as follows.
Conventionally, in order to produce an chloride at a high yield and efficiently by reacting an aliphatic carboxylic acid such as (meth) acrylic acid with phosphorus trichloride, the obtained acid chloride was obtained by simple distillation purification. . Specifically, in the case of an aliphatic carboxylic acid having a reactive double bond such as (meth) acrylic acid, a polymerization inhibitor such as paramethoxyphenol (MEHQ) is added, and the aliphatic carboxylic acid is added. After phosphorus trichloride is added to the acid and reacted, simple distillation is performed to obtain acid chloride as a distillate.
【０００５】しかし、従来の単蒸留精製法で得られた酸
クロライドは、経時的に着色する（黄変する）と言う問
題があり、例えば、レンズ等の光学材料用途や医薬用途
などの合成に用いるには不適当であった。しかも、従来
の単蒸留精製法では、一度目の蒸留では留出分に着色が
残っているので、単蒸留を２回繰り返して精製するよう
にしており、工程が煩雑でコストが嵩んでいた。蒸留塔
の段数を多くして一度で精留することも考えられるが、
これにも費用が嵩むと言う問題がある。However, the acid chloride obtained by the conventional simple distillation purification method has a problem that it is colored (yellowing) with the passage of time. For example, the acid chloride is used for synthesis of optical materials such as lenses and pharmaceuticals. Unsuitable for use. In addition, in the conventional simple distillation purification method, since the distillate remains colored in the first distillation, purification is performed by repeating the simple distillation twice, and the process is complicated and the cost is increased. Although it is conceivable to increase the number of distillation columns and rectify at once,
This also has the problem of increased costs.
【０００６】[0006]
【発明が解決しようとする課題】したがって、本発明の
課題は、経時変化なく無色透明な酸クロライドを、必要
に応じ１回の単蒸留で得ることが出来る酸クロライドの
製造方法を提供することにある。SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a method for producing an acid chloride which can obtain a colorless and transparent acid chloride without change over time by one simple distillation as required. is there.
【０００７】[0007]
【課題を解決するための手段】本発明者は、酸クロライ
ドの黄着色の原因の究明のために、種々の実験を行っ
た。すなわち、三塩化リンを空気中に放置しておくと黄
色く着色してきて、一夜後には黄色の固形物が残った。
また、三塩化リンを少量の水で加水分解した場合、Ｐ−
Ｐ結合やＰ−Ｏ−Ｐ結合が下記のごとくランダムに位置
した黄色ポリマーが生成した。The present inventors have conducted various experiments in order to investigate the cause of yellow coloring of acid chloride. That is, when phosphorus trichloride was left in the air, it was colored yellow, and a yellow solid remained after one night.
Also, when phosphorus trichloride is hydrolyzed with a small amount of water, P-
A yellow polymer in which P bonds and P-O-P bonds were randomly located as described below was produced.
【０００８】[0008]
【化１】 Embedded image
【０００９】[0009]
【化２】 Embedded image
【００１０】[0010]
【化３】 Embedded image
【００１１】下記表１は反応生成物から精留したメタク
リル酸クロライドに、種々の量の三塩化リンを添加した
ときの室温下での色相の経時変化をＡＰＨＡ値で示して
いる。The following Table 1 shows APHA values showing changes over time in hue at room temperature when various amounts of phosphorus trichloride were added to methacrylic acid chloride rectified from the reaction product.
【００１２】[0012]
【表１】 [Table 1]
【００１３】ＡＰＨＡ値が大きいほど、着色が大きいこ
とを示す。ＡＰＨＡ値が５０を超えると、肉眼でも着色
が見える。表１に見るように、ＡＰＨＡ値は三塩化リン
の添加量が多くなるにつれて大きくなっている。なお、
表１では２０日を超えたときのＡＰＨＡ値は示していな
いが、三塩化リンに起因する黄色ポリマーの生成は２０
日を経過するとほぼ飽和に達する。The higher the APHA value, the greater the coloring. When the APHA value exceeds 50, coloring is visible to the naked eye. As shown in Table 1, the APHA value increases as the amount of phosphorus trichloride added increases. In addition,
Table 1 does not show APHA values beyond 20 days, but the formation of yellow polymer due to phosphorus trichloride
After a few days, saturation is reached.
【００１４】この実験結果から、本発明者は、反応生成
液中に残存する三塩化リンに由来する加水分解生成物が
黄色発色物質であることを突き止めた。そこで、本発明
者は、脂肪族カルボン酸と三塩化リンの反応生成物中に
おける三塩化リン残量を少なくする方法として、下記の
４方法を検討した。 （１） 仕込みモル比において脂肪族カルボン酸を過剰
にして、未反応三塩化リンを低減させる方法。From the results of this experiment, the present inventors have found that the hydrolysis product derived from phosphorus trichloride remaining in the reaction product solution is a yellow coloring substance. Thus, the present inventors have studied the following four methods as methods for reducing the residual amount of phosphorus trichloride in the reaction product of an aliphatic carboxylic acid and phosphorus trichloride. (1) A method of reducing the amount of unreacted phosphorus trichloride by increasing the amount of aliphatic carboxylic acid in the charged molar ratio.
【００１５】（２） 反応時に反応系に乾燥空気を吹き
込み、溶存塩酸量を減少させる方法。これは、反応によ
り生成した塩酸が単蒸留精製時に酸クロライドと一緒に
留出し、このとき、反応液中のリン化合物を随伴しやす
いので、その原因となる塩酸を減少しようとする方法で
ある。 （３） 反応生成液中のリン化合物を無機化合物に吸着
させる方法。(2) A method in which dry air is blown into the reaction system during the reaction to reduce the amount of dissolved hydrochloric acid. This is a method in which hydrochloric acid produced by the reaction is distilled out together with acid chloride at the time of simple distillation purification, and at this time, a phosphorus compound in the reaction solution is easily accompanied, so that hydrochloric acid which causes the reduction is reduced. (3) A method in which a phosphorus compound in a reaction product solution is adsorbed on an inorganic compound.
【００１６】（４） 生成液に、液中のリン化合物と錯
体を形成する添加物を加えておいて、酸クロライドを蒸
留精製する方法。これらの方法につき、種々検討した結
果、（４）の方法が工業的に最も有利であることを確認
した。さらに、三塩化リンと錯体を形成する添加物とし
てＮ，Ｎ−ジメチルホルムアミドを用いた場合に高い効
果が得られることを確認して、本発明を完成した。した
がって、本発明にかかる酸クロライドの製造方法は、脂
肪族カルボン酸と三塩化リンとを反応させ、その反応生
成物から蒸留により酸クロライドを得るにあたり、前記
反応生成物に対しＮ，Ｎ−ジメチルホルムアミドを加え
ておいて前記蒸留を行うことを特徴とする。(4) A method in which an additive which forms a complex with the phosphorus compound in the liquid is added to the product liquid, and the acid chloride is purified by distillation. As a result of various studies on these methods, it was confirmed that the method (4) was industrially most advantageous . Furthermore, as an additive that forms a complex with phosphorus trichloride,
High efficiency when using N, N-dimethylformamide
After confirming that the result was obtained , the present invention was completed. Therefore, the manufacturing method of the acid chloride to the present invention, by reacting an aliphatic carboxylic acid and phosphorus trichloride, in obtaining the acid chloride by distillation from the reaction product of that, with respect to the reaction product N, N- It is characterized in that the above-mentioned distillation is carried out with dimethylformamide added.
【００１７】本発明によれば、必要に応じ、前記蒸留は
一度の単蒸留のみを行う蒸留であることが出来る。According to the present invention, if necessary, the distillation can be a single distillation only.
【００１８】[0018]
【発明の実施の形態】本発明において、脂肪族カルボン
酸とはメタクリル酸のような不飽和の脂肪族カルボン酸
やプロピオン酸のような飽和の脂肪族カルボン酸であ
り、Ｎ，Ｎ−ジメチルホルムアミドは三塩化リンと錯体
を形成する添加物である。三塩化リンと錯体を形成する
添加物としては酸化マグネシウムも挙げられるが、本発
明ではＮ，Ｎ−ジメチルホルムアミドが用いられる。 DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, an aliphatic carboxylic acid is an unsaturated aliphatic carboxylic acid such as methacrylic acid or a saturated aliphatic carboxylic acid such as propionic acid, and N, N-dimethylformamide are additive to form a phosphorus trichloride and complexes. Forms a complex with phosphorus trichloride
Magnesium oxide is also an example of an additive.
For clarity, N, N-dimethylformamide is used.
【００１９】脂肪族カルボン酸と三塩化リンとを反応さ
せる方法としては、脂肪族カルボン酸に三塩化リンを滴
下して行くことにより反応させる方法が好適である。三
塩化リンに脂肪族カルボン酸を滴下する方法または三塩
化リンと脂肪族カルボン酸を一括して仕込んで反応させ
る方法のいずれの方法をとっても、前述の方法をとった
場合よりも一般に収率が低くなる傾向がある。しかし、
これらの方法によることも出来る。As a method of reacting the aliphatic carboxylic acid with phosphorus trichloride, a method of reacting the aliphatic carboxylic acid by dropping phosphorus trichloride dropwise is preferable. Either a method of dropping an aliphatic carboxylic acid into phosphorus trichloride or a method of reacting phosphorus trichloride and an aliphatic carboxylic acid in a batch is generally yield higher than that obtained by the above-described method. Tends to be lower. But,
These methods can also be used.
【００２０】三塩化リンを脂肪族カルボン酸に添加する
方法は連続的または継続的方法で行うことができる。通
常、滴下時間は０．５〜３時間が好ましい。滴下時間が
０．５時間より短すぎる場合は収率の向上が小さく、３
時間以上長くしてもさらなる収率の向上は得られず、滴
下時間をこれ以上長くする必要がない。反応系内には、
重合防止剤としてパラメトキシフェノール等のキノン類
などを添加しておくことが好ましい。The method of adding phosphorus trichloride to the aliphatic carboxylic acid can be carried out continuously or continuously. Usually, the dropping time is preferably 0.5 to 3 hours. When the dropping time is shorter than 0.5 hour, the improvement of the yield is small,
Even if the time is longer than this, no further improvement in yield can be obtained, and there is no need to further increase the dropping time. In the reaction system,
It is preferable to add a quinone such as paramethoxyphenol as a polymerization inhibitor.
【００２１】反応温度については、４０〜９０℃の間の
任意の温度で行い得るが、５０〜６０℃がより好まし
い。４０℃未満では反応は非常に遅く、９０℃を越える
温度では不飽和脂肪酸の反応の場合、重合物が増加す
る。三塩化リンの滴下終了後、直ちに酸クロライドを留
出させても差し支えないが、そうすると未反応三塩化リ
ンが製品に多量に混入する場合があるので、１／４〜２
時間の熟成時間をとることが好ましい。Regarding the reaction temperature, the reaction can be carried out at any temperature between 40 and 90 ° C., but more preferably between 50 and 60 ° C. If the temperature is lower than 40 ° C., the reaction is very slow, and if the temperature exceeds 90 ° C., the amount of the polymer increases in the case of the reaction of unsaturated fatty acids. After the completion of the dropping of the phosphorus trichloride, the acid chloride may be immediately distilled off. However, if this occurs, a large amount of unreacted phosphorus trichloride may be mixed into the product.
It is preferable to take time for aging.
【００２２】酸クロライドを留去させる手段としては特
別な蒸留塔は必要としない。例えば、ミストセパレータ
ーや簡単な蒸留塔を使用することも出来る。酸クロライ
ドを留出させる際、常圧でも差し支えないが、メタクリ
ル酸クロライドのような不飽和酸クロライドを留出させ
る場合には、重合等による収率の損失を確実に少なくす
るためには４００ｍｍＨｇ以下の減圧下で蒸留を行うこ
とが好ましい。好ましい実施態様としては２００ｍｍＨ
ｇ位から引きはじめ最終的に３０ｍｍＨｇ位で留出させ
る方法を挙げることができる。As a means for distilling out the acid chloride, no special distillation column is required. For example, a mist separator or a simple distillation column can be used. At the time of distilling out the acid chloride, normal pressure may be used. However, when distilling out the unsaturated acid chloride such as methacrylic acid chloride, 400 mmHg or less in order to surely reduce the loss of the yield due to polymerization or the like. The distillation is preferably performed under reduced pressure. The preferred embodiment is 200 mmH
A method of starting from the g-position and finally distilling at about 30 mmHg can be mentioned.
【００２３】三塩化リンと脂肪族カルボン酸の配合割合
は、特に限定する訳ではないが、三塩化リン／脂肪族カ
ルボン酸（モル比）＝１／４〜１／３であることが好ま
しい。三塩化リンと錯体形成添加物の配合割合は、特に
限定する訳ではないが、残存三塩化リンに対して過剰量
加えることが望ましい。例えば、発生する塩化水素を除
いた理論反応液量に対して３重量％以上添加することが
望ましい。The mixing ratio of phosphorus trichloride and aliphatic carboxylic acid is not particularly limited, but is preferably phosphorus trichloride / aliphatic carboxylic acid (molar ratio) = 1/4 to 1/3. The mixing ratio of the phosphorus trichloride and the complex forming additive is not particularly limited, but it is desirable to add an excessive amount to the remaining phosphorus trichloride. For example, it is desirable to add 3% by weight or more based on the theoretical reaction liquid amount excluding the generated hydrogen chloride.
【００２４】[0024]
【実施例】−実施例１− 攪拌機、温度計、還流冷却器および滴下ロートを備えた
容量１００ｍｌのフラスコにメタクリル酸５９．２ｇ
（０．６９モル）とパラメトキシフェノール５９．０ｍ
ｇを仕込み、５５℃の温度で１２０分間を掛けて三塩化
リン３０．０ｇ（０．２２モル）を滴下し、反応させ
た。その後、９０分を掛けて熟成しつつ温度３０℃に冷
却した。そして、Ｎ，Ｎ−ジメチルホルムアミド３．１
ｇ（０．０４モル）を５０分間掛けて滴下し、３０分熟
成した後、パラメトキシフェノール２．０ｍｇを加え
て、最高温度７０℃、最高減圧度４０Ｔｏｒｒで減圧蒸
留することにより、４０．０ｇ（０．３８モル）のメタ
クリル酸クロライドを得た（メタクリル酸仕込量に対す
る収率５５．５モル％）。EXAMPLES Example 1 59.2 g of methacrylic acid was placed in a 100 ml flask equipped with a stirrer, thermometer, reflux condenser and dropping funnel.
(0.69 mol) and 59.0 m of paramethoxyphenol
g of phosphorus trichloride over a period of 120 minutes at a temperature of 55 ° C., and 30.0 g (0.22 mol) of phosphorus trichloride was added dropwise and reacted. Thereafter, the mixture was cooled to a temperature of 30 ° C. while being aged for 90 minutes. And N, N-dimethylformamide 3.1
g (0.04 mol) was added dropwise over 50 minutes, and after aging for 30 minutes, 2.0 mg of paramethoxyphenol was added, followed by distillation under reduced pressure at a maximum temperature of 70 ° C. and a maximum degree of vacuum of 40 Torr to obtain 40.0 g. (0.38 mol) of methacrylic acid chloride was obtained (yield: 55.5 mol% based on the charged amount of methacrylic acid).
【００２５】得られたメタクリル酸クロライドの留出直
後のＡＰＨＡ値は２０であり、２０日経過後のＡＰＨＡ
値は２０であって、ともに肉眼で見ても着色がなかっ
た。 −比較例１− Ｎ，Ｎ−ジメチルホルムアミドを酸化マグネシウム９．
７５ｇ（０．２４モル）に変えたほかは、実施例１と同
様にして、３５．０ｇ（０．３３モル）のメタクリル酸
クロライドを得た（メタクリル酸仕込量に対する収率４
８．５モル％）。The APHA value immediately after the distillation of the obtained methacrylic acid chloride is 20, and the APHA value after 20 days has passed.
The value was 20, and there was no coloring even with the naked eye. Comparative Example 1 N, N-dimethylformamide was replaced with magnesium oxide9.
Except having changed to 75 g (0.24 mol), 35.0 g (0.33 mol) of methacrylic acid chloride was obtained in the same manner as in Example 1 (yield 4 based on the charged amount of methacrylic acid).
8.5 mol%).
【００２６】得られたメタクリル酸クロライドの留出直
後のＡＰＨＡ値は３０であり、２０日経過後のＡＰＨＡ
値は３０であって、ともに肉眼で見ても着色がなかっ
た。 −実施例２− 攪拌機、温度計、還流冷却器および滴下ロートを備えた
容量１００ｍｌのフラスコにプロピオン酸５１．８ｇ
（０．７０モル）を仕込み、５５℃の温度で１２０分間
を掛けて三塩化リン３０．０ｇ（０．２２モル）を滴下
し、反応させた。その後、９０分を掛けて熟成しつつ温
度３０℃に冷却した。そして、Ｎ，Ｎ−ジメチルホルム
アミド３．１ｇ（０．０４モル）を５０分間掛けて滴下
し、３０分熟成した後、常圧下で蒸留することにより、
３６．１ｇ（０．３９モル）のプロピオン酸クロライド
を得た（プロピオン酸仕込量に対する収率５５．８モル
％）。The APHA value immediately after the distillation of the obtained methacrylic acid chloride was 30, and the APHA value after 20 days had passed.
The value was 30, and there was no coloring even with the naked eye. Example 2 51.8 g of propionic acid in a 100 ml flask equipped with a stirrer, thermometer, reflux condenser and dropping funnel
(0.70 mol) was added, and 30.0 g (0.22 mol) of phosphorus trichloride was added dropwise at a temperature of 55 ° C. over 120 minutes to cause a reaction. Thereafter, the mixture was cooled to a temperature of 30 ° C. while being aged for 90 minutes. Then, 3.1 g (0.04 mol) of N, N-dimethylformamide was added dropwise over 50 minutes, aged for 30 minutes, and distilled under normal pressure.
36.1 g (0.39 mol) of propionic acid chloride was obtained (yield 55.8 mol% based on the amount of propionic acid charged).
【００２７】得られたプロピオン酸クロライドの留出直
後のＡＰＨＡ値は２０であり、２０日経過後のＡＰＨＡ
値は２０であって、ともに肉眼で見ても着色がなかっ
た。The APHA value immediately after the distillation of the obtained propionic acid chloride was 20, and the APHA value after 20 days had passed.
The value was 20, and there was no coloring even with the naked eye.
【００２８】[0028]
【発明の効果】本発明にかかる酸クロライドの製造方法
によれば、経時変化なく無色透明な酸クロライドを得る
ことが出来る。そのため、得られた酸クロライドは光学
用途や医薬用途等の材料などとして有利に用いることが
出来る。本発明にかかる酸クロライドの製造方法によれ
ば、蒸留を１度の単蒸留のみで行うことによって、酸ク
ロライドの製造工程を簡略化できるとともに、酸クロラ
イドの製造コストを低減することも出来る。According to the method for producing an acid chloride according to the present invention, a colorless and transparent acid chloride can be obtained without a change over time. Therefore, the obtained acid chloride can be advantageously used as a material for optical use or medical use. ADVANTAGE OF THE INVENTION According to the manufacturing method of the acid chloride which concerns on this invention, while performing distillation only by one simple distillation, the manufacturing process of an acid chloride can be simplified and the manufacturing cost of an acid chloride can also be reduced.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平６−41000（ＪＰ，Ａ) 特開 平６−63407（ＪＰ，Ａ) 特開 昭64−50839（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 51/64 C07C 53/42 C07C 57/66 ────────────────────────────────────────────────── ─── Continuation of front page (56) References JP-A-6-41000 (JP, A) JP-A-6-63407 (JP, A) JP-A-64-50839 (JP, A) (58) Investigation Field (Int.Cl. 7 , DB name) C07C 51/64 C07C 53/42 C07C 57/66
Claims (1)
せ、その反応液中から蒸留により酸クロライドを得るに
あたり、前記反応液に対しＮ，Ｎ−ジメチルホルムアミ
ドを加えておいて前記蒸留を行うことを特徴とする、酸
クロライドの製造方法。(1) An aliphatic carboxylic acid is reacted with phosphorus trichloride.
Was, in obtaining the acid chloride by distillation from the reaction solution in its, N to the reaction solution, N- dimethylformamidine
A method for producing acid chloride, wherein the distillation is carried out while adding an acid chloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06108298A JP3332341B2 (en) | 1998-03-12 | 1998-03-12 | Method for producing acid chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP06108298A JP3332341B2 (en) | 1998-03-12 | 1998-03-12 | Method for producing acid chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11255703A JPH11255703A (en) | 1999-09-21 |
| JP3332341B2 true JP3332341B2 (en) | 2002-10-07 |
Family
ID=13160845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP06108298A Expired - Lifetime JP3332341B2 (en) | 1998-03-12 | 1998-03-12 | Method for producing acid chloride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3332341B2 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5602981B2 (en) * | 2000-12-18 | 2014-10-08 | 株式会社ダイセル | Method for producing high purity methacrylic acid derivatives |
| JP2003073292A (en) * | 2001-09-04 | 2003-03-12 | Kagome Co Ltd | New cholesterol synthesis inhibitor |
| JP5209201B2 (en) * | 2006-11-30 | 2013-06-12 | 菊川 佐妃子 | Method for producing high-purity organic acid chloride having an unsaturated group in the molecule |
| CN106232566B (en) * | 2014-04-14 | 2018-10-12 | 日油株式会社 | The manufacturing method and fat acyl chloride of fat acyl chloride |
| WO2015159892A1 (en) * | 2014-04-14 | 2015-10-22 | 日油株式会社 | Method for manufacturing fatty acid chloride and fatty acid chloride |
| WO2016163551A1 (en) * | 2015-04-09 | 2016-10-13 | ダイキン工業株式会社 | Composition containing acrylic acid derivative, and method for stabilizing acrylic acid derivative |
| JP6160651B2 (en) * | 2015-04-09 | 2017-07-12 | ダイキン工業株式会社 | Acrylic acid derivative-containing composition and method for stabilizing acrylic acid derivative |
| CN113999110A (en) * | 2021-12-08 | 2022-02-01 | 新华制药（寿光）有限公司 | Method for continuously producing propionyl chloride |
-
1998
- 1998-03-12 JP JP06108298A patent/JP3332341B2/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| JPH11255703A (en) | 1999-09-21 |
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