JPS62181231A - Production of acid anhydride - Google Patents
Production of acid anhydrideInfo
- Publication number
- JPS62181231A JPS62181231A JP60296115A JP29611585A JPS62181231A JP S62181231 A JPS62181231 A JP S62181231A JP 60296115 A JP60296115 A JP 60296115A JP 29611585 A JP29611585 A JP 29611585A JP S62181231 A JPS62181231 A JP S62181231A
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- reaction
- acid anhydride
- anhydride
- acid
- 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
- 150000008065 acid anhydrides Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 10
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims abstract description 9
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 6
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 3
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 3
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 3
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 3
- 229910052749 magnesium Inorganic materials 0.000 claims abstract 2
- 229910052700 potassium Inorganic materials 0.000 claims abstract 2
- 229910052708 sodium Inorganic materials 0.000 claims abstract 2
- 229910052720 vanadium Inorganic materials 0.000 claims abstract 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 25
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 150000004679 hydroxides Chemical class 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 235000019260 propionic acid Nutrition 0.000 abstract description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract description 2
- -1 acetic anhydride Chemical class 0.000 abstract 4
- 150000001455 metallic ions Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003841 chloride salts Chemical class 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 3
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 3
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010866 blackwater Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は有機カルボ／酸無水物とカルボン酸との交換反
応により酸無水物を合成する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for synthesizing acid anhydrides by an exchange reaction between an organic carbo/acid anhydride and a carboxylic acid.
カルボン酸無水物を合成する方法は種々知られているが
、無水酢酸のよう表酸無水物を用いる方法は特別な反応
装置も必要としないため工業的にも最も有用な方法の１
つである。この反応の機構は一般式（１）のように考え
られている。Various methods are known for synthesizing carboxylic acid anhydrides, but the method using a basic acid anhydride such as acetic anhydride is one of the most industrially useful methods because it does not require any special reaction equipment.
It is one. The mechanism of this reaction is thought to be as shown in general formula (1).
この反応の反応速度を上げる方法としては一般的には加
熱による方法が実施されている。As a method of increasing the reaction rate of this reaction, heating is generally used.
（ＲｌＣ−）２０＋Ｒ２Ｃ０Ｈ
（式中Ｒ，，Ｒ２は置換あるいは非置換のアルキル基、
了り−ル基等である。）
〔発明が解決しようとする問題点〕
反応速度を上げるために１００℃以上の高温に加熱する
従来の技術では、原料あるいは生成物としての酸無水物
が比較的熱的に不安定なため、補々の問題が起る。例え
ば、無水酢酸を使用した場合には、これが酢酸やケテン
に分解し、このクテンが重合反応を起しタール状物質が
生成するという欠点がある。又高温に加熱しない場合に
は反応時間が長くなるという欠点がある。(RlC-)20+R2C0H (wherein R,,R2 is a substituted or unsubstituted alkyl group,
It is a group such as ``Rir-ru''. ) [Problems to be solved by the invention] In the conventional technique of heating to a high temperature of 100°C or higher to increase the reaction rate, acid anhydrides as raw materials or products are relatively thermally unstable; A complementary problem arises. For example, when acetic anhydride is used, it has the disadvantage that it decomposes into acetic acid and ketene, and the ketene undergoes a polymerization reaction to produce a tar-like substance. Furthermore, there is a drawback that the reaction time becomes long if the reaction is not heated to a high temperature.
本発明の目的はこの様な問題点を解決することである。The purpose of the present invention is to solve these problems.
本発明者等は、有機カルボン酸無水物とカルボン酸との
交換反応を促進する方法について鋭意検討した結果触媒
として特定の金属イオンを添加することによシ、著しく
反応が促進されることを見い出し、本発明を完成した。The present inventors have conducted intensive studies on methods for promoting the exchange reaction between organic carboxylic acid anhydrides and carboxylic acids, and have discovered that the addition of specific metal ions as catalysts can significantly accelerate the reaction. , completed the invention.
即ち、本発明は、Ｃｏ、Ｎｉ、Ｍｎ、Ｆｅ、Ｌｉ、Ｎａ
、Ｋ、Ｍｇ。That is, the present invention provides Co, Ni, Mn, Fe, Li, Na
, K., Mg.
Ｃａ、Ｃｕ、Ｚｎ、Ａｌ、Ｔｉ、ｌ／から選ばれた１糎
以上の金属イオン５ ＰＰＭ以上の存在下で、有機カル
ボン酸無水物とカルボン酸との交換反応を行うことを特
徴とする酸無水物の製造方法に関するものである。An acid characterized by carrying out an exchange reaction between an organic carboxylic acid anhydride and a carboxylic acid in the presence of 5 PPM or more of one or more metal ions selected from Ca, Cu, Zn, Al, Ti, l/ The present invention relates to a method for producing anhydrides.
本発明は実施例に示したようＫ、有機カルボン酸無水物
とカルボン酸の混合物に触媒量の上記金属からなる金属
塩、あるいは水酸化物等を添加するのみで容易に実施さ
れる。The present invention can be carried out easily by simply adding a catalytic amount of a metal salt or hydroxide of the above-mentioned metal to a mixture of K, an organic carboxylic acid anhydride, and a carboxylic acid, as shown in the Examples.
本発明の金属イオンは硝酸塩、酢酸塩筒の金属塩あるい
は水酸化物、塩化物等として使用される。上記した金属
イオンのうち、Ｇｏ、Ｎｉ、Ｍｎが反応速度等の点でよ
り好ましい。The metal ions of the present invention are used in the form of nitrates, acetates, metal salts, hydroxides, chlorides, and the like. Among the metal ions mentioned above, Go, Ni, and Mn are more preferable in terms of reaction rate and the like.
又、これらの金属イオンは、その触媒効果の点から、反
応系に５ ＰＰＭ以上存在させることが必要である。Further, from the viewpoint of the catalytic effect, it is necessary that these metal ions be present in the reaction system in an amount of 5 PPM or more.
有機カルボン酸無水物とは炭素数１〜５の脂肪酸ような
る酸無水物が好ましく、例えば黒水酢酸、無水プロピオ
ン酸等が挙げられる。又混合酸無水物であってもよい。The organic carboxylic acid anhydride is preferably an acid anhydride such as a fatty acid having 1 to 5 carbon atoms, such as black water acetic acid, propionic anhydride, and the like. It may also be a mixed acid anhydride.
本発明のカルボン酸とは、酸無水物との交換反応により
無水化されるものであれば、特に限定されるものではな
く、脂肪族、芳香族、脂環式、複素環式のモノ、ジ、ト
リ、テトラ、その他ポリカルボン酸がある。中でも脂肪
族カルボン酸が好ましい。The carboxylic acids of the present invention are not particularly limited as long as they can be anhydrified by exchange reaction with acid anhydrides, and include aliphatic, aromatic, alicyclic, and heterocyclic mono- and di-carboxylic acids. , tri, tetra, and other polycarboxylic acids. Among them, aliphatic carboxylic acids are preferred.
具体的には、プロピオン酸、コハク酸、マレインシ、フ
ェニルプロピオン酸、モノクロル酢酸、アクリル酸等が
ある。Specifically, there are propionic acid, succinic acid, maleic acid, phenylpropionic acid, monochloroacetic acid, acrylic acid, and the like.
本発明の方法において反応温度は、使用する原料によシ
適宜選択されるが、通常は１０℃から、原料おるいは生
成物の沸点程度が好ましい。In the method of the present invention, the reaction temperature is appropriately selected depending on the raw materials used, but is usually from 10° C. to about the boiling point of the raw materials or products.
又、反応に使用する有機カルボン酸無水物は、カルボン
酸に対して、１当量以上用いられる。Further, the organic carboxylic acid anhydride used in the reaction is used in an amount of 1 equivalent or more based on the carboxylic acid.
本発明における反応は、平衡反応のため該反応温度にお
ける各成分の熱力学的安定性によって反応の変化率が決
定される。無水物の当Ｉ：を極力減らしたい場合は無水
酢酸を例にとると、生成する酢酸を蒸留等の方法により
反応系から除去すれば、はぼ理論量の無水酢酸が有れば
良い。Since the reaction in the present invention is an equilibrium reaction, the rate of change in the reaction is determined by the thermodynamic stability of each component at the reaction temperature. Taking acetic anhydride as an example, if it is desired to reduce the amount of anhydride (I) as much as possible, it is sufficient to have approximately the stoichiometric amount of acetic anhydride, as long as the produced acetic acid is removed from the reaction system by a method such as distillation.
また、目的の無水物が結晶として糸外に除去される場合
もほぼ理論量の無水酢酸によって目的が達成される。Furthermore, even when the target anhydride is removed from the thread in the form of crystals, the target can be achieved using a nearly stoichiometric amount of acetic anhydride.
（発明の効果〕
本発明の触媒を使用することにより、温和な条件で反応
が短時間に進行し、タール状物質の生成等が防止される
。(Effects of the Invention) By using the catalyst of the present invention, the reaction proceeds in a short time under mild conditions, and the formation of tar-like substances is prevented.
又、熱的に不安定な物質の合成をも可能にした。It also made it possible to synthesize thermally unstable substances.
実施例１および比較例１
゛ 無水酢酸１０２，９．プロピオンｒＲ７４，９をフ
ラスコに入れ１時間で７０℃まで昇温し、その後７０℃
を維持して反応をガスクロマトグラフィーで追跡した。Example 1 and Comparative Example 1 ゛ Acetic anhydride 102,9. Put propion rR74,9 in a flask and raise the temperature to 70℃ for 1 hour, then 70℃
The reaction was followed by gas chromatography.
同一条件で触媒として硝酸コバルト０．８ｇを加え２０
℃で１０分間攪拌した時点で反応は既に平衡し達してい
た（第１図への点線。）又、タール状物の生成もみられ
なかった。Under the same conditions, 0.8 g of cobalt nitrate was added as a catalyst for 20
By the time the mixture was stirred for 10 minutes at .degree. C., the reaction had already reached equilibrium (dotted line in FIG. 1), and no tar-like material was observed.
実施例２
とは＜ ２ ａｓ、ｓ ｇと無水酢［１５３９をフラス
コに入れ、１時間で５０℃まで昇温し、その後５０℃を
維持して副生する酢酸と無水酢酸の比率をガスクロマト
グラフィーで追跡した（第２図実線）。Example 2 means <2 as, s g and anhydrous vinegar [1539] were placed in a flask, the temperature was raised to 50 °C for 1 hour, and then the temperature was maintained at 50 °C to measure the ratio of by-produced acetic acid and acetic anhydride using gas chromatography. It was tracked graphically (solid line in Figure 2).
同一条件で硝酸コバルトｒｃｏ（Ｎｏ５）２−６Ｈ２０
）０．１ｇを添加し反応を行ったところ昇温終了時には
既に反応は終了していた。また更に硝酸コバルト量を２
０鑓に減した場合も同じ結果を得だ（第２図点線）。タ
ール分の生成も認められなかった。Cobalt nitrate rco(No5)2-6H20 under the same conditions
) 0.1 g was added and the reaction was carried out, but the reaction had already been completed by the time the temperature was raised. Furthermore, the amount of cobalt nitrate is 2
The same result is obtained when the number is reduced to 0 (dotted line in Figure 2). No formation of tar was observed.
第１図、第２図はそれぞれ実力例１．実施例２の結果を
示すグラフである。
出願人代理人 古 谷 娶
第 １ 図
反応時間（時間）
第２図
反応時間（時間）
手続補正書印釦
昭和６１年１０月３１日Figures 1 and 2 are examples of actual performance 1. 3 is a graph showing the results of Example 2. Applicant's agent: Ms. Furuya Figure 1 Reaction time (hours) Figure 2 Reaction time (hours) Procedural amendment stamp button October 31, 1986
Claims (1)
Ｃａ、Ｃｕ、Ｚｎ、Ａｌ、Ｔｉ、Ｖから選ばれた１種以
上の金属イオン５ＰＰＭ以上の存在下で、有機カルボン
酸無水物とカルボン酸との交換反応を行うことを特徴と
する酸無水物の製造方法。 ２ カルボン酸が置換あるいは非置換の脂肪族カルボン
酸である特許請求の範囲第１項記載の酸無水物の製造方
法。 ３ 金属イオンがＣｏ、Ｎｉ、Ｍｎである特許請求の範
囲第１項又は第２項記載の酸無水物の製造方法。[Claims] 1 Co, Ni, Mn, Fe, Li, Na, K, Mg,
An acid anhydride characterized by carrying out an exchange reaction between an organic carboxylic acid anhydride and a carboxylic acid in the presence of 5 PPM or more of one or more metal ions selected from Ca, Cu, Zn, Al, Ti, and V. manufacturing method. 2. The method for producing an acid anhydride according to claim 1, wherein the carboxylic acid is a substituted or unsubstituted aliphatic carboxylic acid. 3. The method for producing an acid anhydride according to claim 1 or 2, wherein the metal ion is Co, Ni, or Mn.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60296115A JPH0780806B2 (en) | 1985-12-25 | 1985-12-25 | Method for producing acid anhydride |
| AT0342186A AT395975B (en) | 1985-12-25 | 1986-12-23 | METHOD FOR PRODUCING AN ORGANIC CARBONIC ACID ANHYDRIDE |
| DE3644222A DE3644222C2 (en) | 1985-12-25 | 1986-12-23 | Process for the preparation of carboxylic anhydrides |
| US06/946,462 US4830789A (en) | 1985-12-25 | 1986-12-24 | Process for producing carboxylic acid anhydrides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60296115A JPH0780806B2 (en) | 1985-12-25 | 1985-12-25 | Method for producing acid anhydride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62181231A true JPS62181231A (en) | 1987-08-08 |
| JPH0780806B2 JPH0780806B2 (en) | 1995-08-30 |
Family
ID=17829328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60296115A Expired - Lifetime JPH0780806B2 (en) | 1985-12-25 | 1985-12-25 | Method for producing acid anhydride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0780806B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010016493A1 (en) * | 2008-08-05 | 2010-02-11 | 三菱レイヨン株式会社 | Method for producing (meth)acrylic acid anhydride, method for storing (meth)acrylic acid anhydride, and method for producing (meth)acrylate ester |
| CN112047834A (en) * | 2020-08-11 | 2020-12-08 | 浙江恒澜科技有限公司 | Device and method for continuously preparing isobutyric anhydride |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62158237A (en) * | 1985-12-24 | 1987-07-14 | ソシエテ シミツク デ シヤルボナ−ジユ エス．ア−． | Synthesis of (meth)acrylic acid anhydride |
-
1985
- 1985-12-25 JP JP60296115A patent/JPH0780806B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62158237A (en) * | 1985-12-24 | 1987-07-14 | ソシエテ シミツク デ シヤルボナ−ジユ エス．ア−． | Synthesis of (meth)acrylic acid anhydride |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010016493A1 (en) * | 2008-08-05 | 2010-02-11 | 三菱レイヨン株式会社 | Method for producing (meth)acrylic acid anhydride, method for storing (meth)acrylic acid anhydride, and method for producing (meth)acrylate ester |
| JPWO2010016493A1 (en) * | 2008-08-05 | 2012-01-26 | 三菱レイヨン株式会社 | Manufacturing method and storage method of (meth) acrylic anhydride, and manufacturing method of (meth) acrylic acid ester |
| US8586791B2 (en) | 2008-08-05 | 2013-11-19 | Mitsubishi Rayon Co., Ltd. | Method for producing (meth)acrylic anhydride, method for storing (meth)acrylic anhydride, and method for producing (meth)acrylate |
| JP5448830B2 (en) * | 2008-08-05 | 2014-03-19 | 三菱レイヨン株式会社 | Manufacturing method and storage method of (meth) acrylic anhydride, and manufacturing method of (meth) acrylic acid ester |
| US8710262B2 (en) | 2008-08-05 | 2014-04-29 | Mitsubishi Rayon Co., Ltd. | Method for producing (meth)acrylic anhydride, method for storing (meth)acrylic anhydride, and method for producing (meth)acrylate |
| CN112047834A (en) * | 2020-08-11 | 2020-12-08 | 浙江恒澜科技有限公司 | Device and method for continuously preparing isobutyric anhydride |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0780806B2 (en) | 1995-08-30 |
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