JPS61251649A - Production of dicarboxylic acid dianilide - Google Patents

Production of dicarboxylic acid dianilide

Info

Publication number
JPS61251649A
JPS61251649A JP7227385A JP7227385A JPS61251649A JP S61251649 A JPS61251649 A JP S61251649A JP 7227385 A JP7227385 A JP 7227385A JP 7227385 A JP7227385 A JP 7227385A JP S61251649 A JPS61251649 A JP S61251649A
Authority
JP
Japan
Prior art keywords
dicarboxylic acid
aniline
reaction
solvent
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
Application number
JP7227385A
Other languages
Japanese (ja)
Other versions
JPH0465057B2 (en
Inventor
Masashi Inaba
正志 稲葉
Yukiyoshi Inui
乾 至良
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Petrochemical Co Ltd
Original Assignee
Mitsubishi Petrochemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Petrochemical Co Ltd filed Critical Mitsubishi Petrochemical Co Ltd
Priority to JP7227385A priority Critical patent/JPS61251649A/en
Publication of JPS61251649A publication Critical patent/JPS61251649A/en
Publication of JPH0465057B2 publication Critical patent/JPH0465057B2/ja
Granted legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PURPOSE:To obtain in a high yield a compound useful as a fluidity improver for resins, etc., under a condition of reduced loss of raw material aniline, by condensing a dicarboxylic acid with aniline by the use of a specific solvent under heating. CONSTITUTION:A dicarboxylic acid shown by the formula HOOC-R-COOH (R is 1-10C alkyl, alkenyl or aryl) is condensed with aniline in the presence of a solvent (e.g., ethylbenzene or diethylbenzene) having 80-200 deg.C boiling point to form an azeotropic mixture at atmospheric pressure under heating at 120-200 deg.C to give the aimed substance. The amount of the solvent used is 5-70wt%, preferably 10-40wt% based on the reaction mixture solution, the raw material carboxylic acid and aniline are used in a molar ratio of 1/2-1/10 and the reaction is carried out.

Description

【発明の詳細な説明】 技術分野 本発明は、ジカルボン酸ジアニリドの製造法に関するも
のである。
DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to a method for producing dicarboxylic dianilides.

本発明の方法によれば、目的物の着色が抑制されまた原
料アニIJンの損失を低下させた条件で収率よく目的と
するジカルボン酸ジアニリドが製造できる。
According to the method of the present invention, the desired dicarboxylic acid dianilide can be produced in good yield under conditions where coloring of the desired product is suppressed and loss of raw material aniline is reduced.

ジカルボン酸ジアニリドは、ポリフェニレンエーテル系
樹脂などの熱可塑性樹脂の流動改良剤となる(例えば特
開昭60−44547号公報等参照)など産業上有用な
゛物質である。
Dicarboxylic acid dianilide is an industrially useful substance that serves as a flow improver for thermoplastic resins such as polyphenylene ether resins (see, for example, Japanese Patent Application Laid-Open No. 60-44547).

先行技術 モノカルボン酸アニリド類は、例えば安息香酸とアニリ
ンとの混合物を加熱し、副生ずる水をアニリンとの共沸
により反応系外に留去する方法(Organic 5y
ntheais、  vol l 、  82(194
1) )、或いはギ酸とN−メチルアニリンとの混合物
をトルエンの存在下加熱し、副生する水をトルエンとの
共沸により反応系外へ留去する方法(OrganicS
ynthesis、vol II、590(1955)
 )等が知られているが、前者の場合留出した水にアニ
リンが溶解し損失となり、後者の場合ギ酸がトルエン及
び水と共に留出する為ギ酸が損失するといった欠点を有
している。また、上記文献にはジカルボン酸を出発原料
とする方法については何ら記載されていない。
Prior art monocarboxylic acid anilides can be produced by, for example, a method (Organic 5y
ntheais, vol. 82 (194
1) ), or a method in which a mixture of formic acid and N-methylaniline is heated in the presence of toluene, and by-produced water is distilled out of the reaction system by azeotropic distillation with toluene (OrganicS
synthesis, vol II, 590 (1955)
), but the disadvantages are that in the former case, aniline is dissolved in the distilled water, resulting in a loss, and in the latter case, formic acid is distilled out together with toluene and water, resulting in a loss of formic acid. Moreover, the above-mentioned literature does not describe any method using dicarboxylic acid as a starting material.

一方、ジカルボン酸ジアニリドは相当するジカルボン酸
塩化物とアニリンとを反応さ老ることKより製造できる
ことは既によく知られている。しかしこの場合、一般に
カルボン酸塩化物が高価であること及び塩化水素が副生
する為に工業的に生産するには不利であると考えられる
。そこでジカルボン酸塩化物以外のものを出発原料とす
るジカルボン酸ジアニリドの製造法が求められるが、こ
れに関しても以前から研究されていた。例えば、ジカル
ボン酸とジフェニル尿素とを混合加熱する方法(Che
m、 Ber、、旦、945(1953))、ジカルボ
ン酸とジフェニルスルファミドをピリジンの存在下で反
応させる方法(Chem、 Abstr、、899h(
1955))が提案されているが、いずれの場合もアミ
ド化試剤はアニリンより合成せねばならず工業的には満
足のいく水準ではなかった。
On the other hand, it is already well known that dicarboxylic acid dianilide can be produced from K by reacting the corresponding dicarboxylic acid chloride with aniline. However, in this case, it is considered to be disadvantageous for industrial production because the carboxylic acid chloride is generally expensive and hydrogen chloride is produced as a by-product. Therefore, there is a need for a method for producing dicarboxylic acid dianilides using materials other than dicarboxylic acid chlorides as starting materials, and this has also been studied for some time. For example, a method of mixing and heating dicarboxylic acid and diphenyl urea (Che
M, Ber, Dan, 945 (1953)), a method for reacting dicarboxylic acid and diphenylsulfamide in the presence of pyridine (Chem, Abstr, 899h (
1955)), but in both cases the amidation reagent had to be synthesized from aniline and was not at an industrially satisfactory level.

発明が解決しようとする問題点 本発明者らは、−ジカルボン酸とアニリントラ直接反応
させジカルボン酸ジアニリドを製造する方法につき検討
を行なった。しかしながらジカルボン酸とアニリンのみ
を直接反応させ副生する水をアニリンとの共沸により系
外へ留去させる方法で反応を実施した場合、次の様な欠
点を有することが判明した。すなわち第1には副生ずる
水を効率良く系外に留去させた場合反応温度が高くなり
、その為にアニリンによる熱的劣化等の副反応が増加し
且つ生成物のジカルボン酸ジアニIJドの色相が悪化す
る。そして更に、未反応のアニリンやジカルボン酸モノ
アニリドを循還再使用しようとする際には、製品色相が
一層悪くなる。第2には反応系外へ留去した水にアニリ
ンが溶解し損失量が多く工業的な実施においては不利と
なること等である。
Problems to be Solved by the Invention The present inventors have investigated a method for producing dicarboxylic acid dianilide by directly reacting -dicarboxylic acid with aniline. However, it has been found that when the reaction is carried out by directly reacting only the dicarboxylic acid and aniline and distilling by-product water out of the system by azeotroping with the aniline, the following drawbacks occur. Firstly, when the by-produced water is efficiently distilled out of the system, the reaction temperature becomes high, which increases side reactions such as thermal deterioration due to aniline, and reduces the dicarboxylic acid dianiline IJ-do product. The hue deteriorates. Furthermore, when unreacted aniline or dicarboxylic acid monoanilide is recycled and reused, the color of the product becomes even worse. Secondly, aniline is dissolved in the water distilled out of the reaction system, resulting in a large amount of loss, which is disadvantageous in industrial implementation.

発明の要旨 本発明は、上記問題点の解消を図るものである。Summary of the invention The present invention aims to solve the above problems.

即ち、本発明は、一般式、HOOC−R−COOH(式
中1Rは01〜10のアルキル基、アルケニル基又はア
リール基を示す)で表わされるジカルボン酸とアニIJ
ンとを溶媒の存在下加熱縮合反応させてジカルボン酸ジ
アニリドを製造する方法において、該溶媒が水と共沸す
る大気圧下の沸点が80〜200℃の範囲のものであり
、その使用量が反応混合液に対する重量割合で5〜70
%の範囲でありかつ加熱縮合反応が120〜200℃の
範囲で行われることを特徴とするジカルボン酸ジアニリ
ドの製造法を提供するものである。
That is, the present invention relates to a dicarboxylic acid represented by the general formula HOOC-R-COOH (in the formula, 1R represents an alkyl group, an alkenyl group, or an aryl group of 01 to 10) and an IJ
In the method for producing dicarboxylic acid dianilide by heating and condensing reaction with water in the presence of a solvent, the solvent has a boiling point azeotropically with water in the range of 80 to 200°C under atmospheric pressure, and the amount used is 5 to 70 in weight proportion to the reaction mixture
% range and the heating condensation reaction is carried out in the range of 120 to 200°C.

ByLすか艮 本発明の方法によれば目的物の色相を悪化させる様な副
反応が抑制でき、色相の良好なジカルボン酸ジアニリド
が得られるのでこれを樹脂の流動性改良剤等として使用
した時に着色等の問題が生じない。
According to the method of the present invention, side reactions that would deteriorate the hue of the target product can be suppressed, and a dicarboxylic dianilide with a good hue can be obtained, so when it is used as a fluidity improver for resins, etc., it can be colored easily. No such problems arise.

ま九、特定の溶媒を使用することにより原料の一つであ
るアニリンの損失が低下でき、反応混合物から目的物を
分離した残液を循環再使用しても目的物の色相悪化の問
題は生じない。
(9) By using a specific solvent, the loss of aniline, which is one of the raw materials, can be reduced, and even if the residual liquid after separating the target product from the reaction mixture is recycled and reused, the problem of deterioration of the color of the target product does not occur. do not have.

発明の詳細な説明 薄 本発明の方法において用いられる間諜は、水と共沸する
大気圧下での沸点が80〜200tl:の範囲のもので
ある。具体的にはエチルベンゼン、キシレン、キュメン
、ジエチルベンゼン、n−7”カン等が例示できるがキ
シレン、エチルベンゼン又はジエチルベンゼンが好まし
く、特にエチルベンゼン又はジエチルベンゼン゛が好ま
しい。
DETAILED DESCRIPTION OF THE INVENTION The liquid used in the process of the present invention has a boiling point at atmospheric pressure that is azeotropic with water and has a boiling point in the range of 80 to 200 tl. Specific examples thereof include ethylbenzene, xylene, cumene, diethylbenzene, n-7'' kane, etc., with xylene, ethylbenzene or diethylbenzene being preferred, and ethylbenzene or diethylbenzene being particularly preferred.

上記溶媒の使用量としては、反応混合液に対する重量割
合で5〜70%の範囲が好ましく、特に10〜40%の
範囲が好ましい。上記重量割合が5%より小さい場合に
は、アニリンの劣化による副反応が起こったり生成物の
ジカルボン酸ジアニリドに着色がみられる等好ましくな
い。また重量割合が70%を越える場合には反応速度が
低下し、工業的には不利である。
The amount of the solvent used is preferably in the range of 5 to 70%, particularly preferably in the range of 10 to 40%, based on the weight ratio of the reaction mixture. If the weight ratio is less than 5%, it is not preferable that side reactions occur due to deterioration of aniline or that the dicarboxylic acid dianilide product is colored. Furthermore, if the weight ratio exceeds 70%, the reaction rate decreases, which is industrially disadvantageous.

反応温度は、使用するジカルボン酸、アニリン及び溶媒
の重量比により変化するが一般に120〜200℃の範
囲が好ましい。
The reaction temperature varies depending on the weight ratio of the dicarboxylic acid, aniline, and solvent used, but is generally preferably in the range of 120 to 200°C.

本発明において用いられる一般式、 HOOC−R−COOHで表わされるジカルボン酸とし
てはRが01〜1Gのアルキル基、アルケニル基又はア
リール基である例えばマロン酸、コハク酸、グルタル酸
、アジピン酸、ピメリン酸、セパシン酸、ドデカンニ酸
、イタコン酸、フマル酸、マレイン酸、フタル酸等が挙
げられる。
The dicarboxylic acids represented by the general formula HOOC-R-COOH used in the present invention include malonic acid, succinic acid, glutaric acid, adipic acid, pimeline, where R is an alkyl group, alkenyl group, or aryl group of 01 to 1G. Examples include sepacic acid, dodecanoic acid, itaconic acid, fumaric acid, maleic acid, phthalic acid, and the like.

原料のジカルボン酸とアニリンとの使用モル比はV2〜
V1nの範囲が好ましく、特に”/2 、s 〜”/s
の範囲が好ましい。上記モル比が1/!を越えてジカル
ボン酸の量が多くなると未反応ジカルボン酸の残存量が
多くなり好ましくない。またモル比が1/10を越えて
アニリンの量が多い場合には反応液量が多くなり釜収率
が低下し経済性が悪化するので工業的に実施するには不
利である。
The molar ratio of raw material dicarboxylic acid and aniline used is V2 ~
The range of V1n is preferable, especially "/2, s ~"/s
A range of is preferred. The above molar ratio is 1/! If the amount of dicarboxylic acid increases beyond this value, the amount of unreacted dicarboxylic acid remaining will increase, which is not preferable. Furthermore, if the molar ratio exceeds 1/10 and the amount of aniline is large, the amount of reaction liquid will increase, the pot yield will decrease, and economic efficiency will deteriorate, which is disadvantageous for industrial implementation.

本発明を具体的に実施する方法としては、ジカルボン酸
、アニリン及び溶媒からなる反応混合物を加熱し、副生
する水を溶媒との共沸により反応系外へ留出させ溶媒層
と水層とに分離した後、溶媒層を反応系へ循環させる方
法が好ましい。アニリンは上記共沸混合物と共に留出し
てくるが、溶媒としてエチルベンゼン等の芳香族炭化水
素を用いた場合、アニリンの水層への損失は非常に低く
抑えられるので特に好ましい。
A specific method for implementing the present invention is to heat a reaction mixture consisting of a dicarboxylic acid, aniline, and a solvent, and distill by-produced water out of the reaction system by azeotropy with the solvent, thereby forming a solvent layer and an aqueous layer. A preferred method is to separate the solvent layer and then circulate the solvent layer to the reaction system. Aniline is distilled out together with the azeotrope, but it is particularly preferable to use an aromatic hydrocarbon such as ethylbenzene as the solvent because the loss of aniline to the aqueous layer can be suppressed to a very low level.

反応終了後反応混合物を冷却し、ジカルボン酸ジアニリ
ドを晶出、させ炉別すると粗ジカルボン酸ジアニリドが
得られる。このものをメタノールエタノール等の低級ア
ルコール類又はトルエン、キシレン、エチルベンゼン等
の芳香族炭化水素等で洗浄することにより白色の精製ジ
カルボン酸ジアニリドが得られる。
After the reaction is completed, the reaction mixture is cooled, dicarboxylic dianilide is crystallized, and the mixture is separated from the furnace to obtain crude dicarboxylic dianilide. By washing this product with lower alcohols such as methanol and ethanol, or aromatic hydrocarbons such as toluene, xylene, and ethylbenzene, white purified dicarboxylic acid dianilide is obtained.

反応混合物から目的物を晶出させた後の濾過Kにより得
られるPgは、アニリン、ジカルボン酸、シカルホン酸
モノアニリド、ジカルボン酸ジアニリド、反応溶媒を含
有しているので、これを反応工程に循環しジカルボン酸
ジアニリドの[料として再使用が可能である。
The Pg obtained by filtration K after crystallizing the target product from the reaction mixture contains aniline, dicarboxylic acid, sicarboxylic acid monoanilide, dicarboxylic acid dianilide, and reaction solvent, so it is recycled to the reaction process to obtain dicarboxylic acid. It can be reused as a raw material for acid dianilide.

実験例 実施例1〜11 ジカルボン酸、アニリン及び反応溶媒をそれぞれ表IK
示す優づつ内容量300mの三つロフラスコに仕込み、
生成する水を反応溶媒との共沸混合物として反応系外罠
留去しながら所定時間加熱攪拌した。反応終了後、反応
混合物を40C以下に冷却し結晶を晶出させ九。この結
晶を炉別し、溶剤で攪拌洗浄した後減圧下にて乾燥した
。得られた結晶は、IR,マススペクトル、聞「スペク
トル等でジカルボン酸ジアニリドであることを確認した
。留去した水中のアニリンはガスクロマトグラフィーに
よシ分析を行なった。反応及び分析の結果を表1に示し
た。ここで反応温度は、副生する水が反応溶媒との共沸
により糸外に留出し始めた時の反応混合物の温度及び所
定時間攪拌した直後の反応混合物の温度である。また、
ジカルボン酸アニリド収率は、仕込みジカルボン酸31
 (mol )に対する生成ジカルボン酸ジアニ!J)
’量(mol)の割合で示したものである。留出水中ア
ニリン濃度は、留出水重量と留出アニリン重量の和に対
するアニリンの重量%で表わしたものである。
Experimental Examples Examples 1 to 11 Dicarboxylic acid, aniline, and reaction solvent are shown in Table IK.
Pour into a three-bottle flask with a capacity of 300 m as shown below.
The resulting water was heated and stirred for a predetermined time while being distilled off from the reaction system as an azeotropic mixture with the reaction solvent. After the reaction is completed, the reaction mixture is cooled to below 40C to crystallize crystals.9. The crystals were separated in a furnace, stirred and washed with a solvent, and then dried under reduced pressure. The obtained crystals were confirmed to be dicarboxylic acid dianilide by IR, mass spectra, electrospectroscopy, etc.Aniline in the distilled water was analyzed by gas chromatography.The results of the reaction and analysis were It is shown in Table 1.Here, the reaction temperature is the temperature of the reaction mixture when by-product water starts to distill out of the thread through azeotropy with the reaction solvent, and the temperature of the reaction mixture immediately after stirring for a predetermined period of time. .Also,
The dicarboxylic acid anilide yield is based on the charged dicarboxylic acid 31
(mol) of produced dicarboxylic acid diani! J)
'It is expressed as a ratio of amount (mol). The aniline concentration in distilled water is expressed as the weight percent of aniline based on the sum of the weight of distilled water and the weight of distilled aniline.

(以下余白) 比較例1 アジピン酸43.8 ? (0,3モル)、アニリン1
76.7 f (1,9モル)を用い反応溶媒を添加し
ない他は実施例1〜11と同じ方法により反応を実施し
た。反応温度は161〜220℃、ジアニリド収率86
.5%であり生成物の色は灰褐色を滞びていた。留出水
量は9.82で、留出水中のアニリン濃度は2.8重i
t%でありた。
(Left below) Comparative Example 1 Adipic acid 43.8 ? (0.3 mol), aniline 1
The reaction was carried out in the same manner as in Examples 1 to 11, except that 76.7 f (1.9 mol) was used and no reaction solvent was added. Reaction temperature: 161-220°C, dianilide yield: 86
.. 5%, and the color of the product remained grayish brown. The amount of distilled water is 9.82, and the aniline concentration in the distilled water is 2.8
It was t%.

実施例12 アジピン酸43.89 (0,3モル)、アニリン13
9.5F(1,5モル)及びエチルベンゼン26.72
を用い実施例1〜11と同じ方法により反応を実施した
。反応終了後、反応混合物を40℃以下に冷却し晶出し
た結晶を炉別して得られたF液と、前記操作に於いて得
られた結晶をメタノールを用いて洗浄した後に炉別して
得られる洗浄液を濃縮して得られる残渣を合わせて回収
未反応物とし、このものに新たにアジピン酸、アニリン
及びエチルベンゼンを添加し反応させることを4回操9
返し実施した。5回実施した反応のアジピン酸ジア二リ
ドの平均収率はアジピン酸基準で95.4%でちゃ、製
品のジカルボン酸ジアニリドはいずれも白色であった。
Example 12 Adipic acid 43.89 (0.3 mol), aniline 13
9.5F (1.5 mol) and ethylbenzene 26.72
The reaction was carried out in the same manner as in Examples 1 to 11 using . After the reaction is completed, the reaction mixture is cooled to 40° C. or below, and the crystals that have crystallized are separated in a furnace.The F solution obtained is obtained by washing the crystals obtained in the above operation with methanol, and the washing liquid obtained by being separated in a furnace. The residue obtained by concentration was combined as the recovered unreacted material, and adipic acid, aniline, and ethylbenzene were newly added and reacted four times.
I implemented it again. The average yield of adipic dianilide in the five reactions was 95.4% based on adipic acid, and all dicarboxylic dianilide products were white.

Claims (1)

【特許請求の範囲】[Claims] (1)一般式、HOOC−R−COOH(式中、RはC
_1_〜_1_0のアルキル基、アルケニル基又はアリ
ール基を示す)で表わされるジカルボン酸とアニリンと
を溶媒の存在下加熱縮合反応させてジカルボン酸ジアニ
リドを製造する方法において、該溶媒が水と共沸する大
気圧下の沸点が80〜200℃の範囲のものであり、そ
の使用量が反応混合液に対する重量割合で5〜70%の
範囲でありかつ加熱縮合反応が 120〜200℃の範囲で行われることを特徴とするジ
カルボン酸ジアニリドの製造法。
(1) General formula, HOOC-R-COOH (wherein R is C
A method for producing a dicarboxylic acid dianilide by subjecting a dicarboxylic acid represented by _1_ to _1_0 (representing an alkyl group, alkenyl group or aryl group) and aniline to a heating condensation reaction in the presence of a solvent, in which the solvent is azeotropic with water. The boiling point under atmospheric pressure is in the range of 80 to 200°C, the amount used is in the range of 5 to 70% by weight of the reaction mixture, and the heating condensation reaction is carried out in the range of 120 to 200°C. A method for producing dicarboxylic acid dianilide, characterized by:
JP7227385A 1985-04-05 1985-04-05 Production of dicarboxylic acid dianilide Granted JPS61251649A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP7227385A JPS61251649A (en) 1985-04-05 1985-04-05 Production of dicarboxylic acid dianilide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP7227385A JPS61251649A (en) 1985-04-05 1985-04-05 Production of dicarboxylic acid dianilide

Publications (2)

Publication Number Publication Date
JPS61251649A true JPS61251649A (en) 1986-11-08
JPH0465057B2 JPH0465057B2 (en) 1992-10-16

Family

ID=13484510

Family Applications (1)

Application Number Title Priority Date Filing Date
JP7227385A Granted JPS61251649A (en) 1985-04-05 1985-04-05 Production of dicarboxylic acid dianilide

Country Status (1)

Country Link
JP (1) JPS61251649A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010006822A (en) * 2002-03-04 2010-01-14 Merck Hdac Research Llc Method of inducing terminal differentiation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010006822A (en) * 2002-03-04 2010-01-14 Merck Hdac Research Llc Method of inducing terminal differentiation
JP2014237669A (en) * 2002-03-04 2014-12-18 メルク・エイチ・デイ・エイ・シー・リサーチ,エル・エル・シー Method of inducing final differentiation

Also Published As

Publication number Publication date
JPH0465057B2 (en) 1992-10-16

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