JPH06279378A - Production of naphthalenecarboxylic acid diimide - Google Patents
Production of naphthalenecarboxylic acid diimideInfo
- Publication number
- JPH06279378A JPH06279378A JP5092425A JP9242593A JPH06279378A JP H06279378 A JPH06279378 A JP H06279378A JP 5092425 A JP5092425 A JP 5092425A JP 9242593 A JP9242593 A JP 9242593A JP H06279378 A JPH06279378 A JP H06279378A
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- general formula
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- amine
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Classifications
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- 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
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規なナフタレンジカ
ルボン酸ジアミドの製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a novel naphthalene dicarboxylic acid diamide.
【０００２】[0002]
【従来の技術】本発明に係り、下記の一般式（１）で表
わされるナフタレンジカルボン酸ジアミドは、結晶性ポ
リプロピレン樹脂のβ晶核剤として有用な化合物である
（特願平４−１３５８９２号、特願平４−３４０８８
号）。BACKGROUND OF THE INVENTION In the present invention, naphthalene dicarboxylic acid diamide represented by the following general formula (1) is a compound useful as a β-crystal nucleating agent for crystalline polypropylene resin (Japanese Patent Application No. 4-135892). Japanese Patent Application No. 4-34088
issue).
【０００３】ナフタレンジカルボン酸ジアミドの製造方
法として、具体的には以下の方法が考えられる。即ち、 （１）カルボン酸と一級アミン若しくは二級アミン等の
アミン類との加熱脱水による方法。As a method for producing naphthalenedicarboxylic acid diamide, the following methods are specifically considered. That is, (1) a method of heating and dehydrating a carboxylic acid and an amine such as a primary amine or a secondary amine.
【０００４】（２）アルカリ触媒存在下、カルボン酸低
級アルキルエステルとアミン類とのエステル・アミド交
換反応による方法。(2) A method by an ester-amide exchange reaction between a lower alkyl carboxylic acid ester and amines in the presence of an alkali catalyst.
【０００５】（３）カルボン酸低級アルキルエステルと
アミン類との加熱下でのエステル・アミド交換反応によ
る方法。(3) A method by an ester-amide exchange reaction of a lower alkyl carboxylic acid ester and an amine with heating.
【０００６】（４）カルボン酸クロリドとアミン類との
反応のよる方法。(4) A method of reacting a carboxylic acid chloride with amines.
【０００７】[0007]
【発明が解決しようとする課題】本発明は、新規有用な
ナフタレンジカルボン酸ジアミド類を温和な条件で高収
率で製造しうる工業的に優れた製造方法を提供すること
を目的とする。SUMMARY OF THE INVENTION It is an object of the present invention to provide an industrially excellent production method capable of producing a novel and useful naphthalene dicarboxylic acid diamide in a high yield under mild conditions.
【０００８】[0008]
【課題を解決するための手段】本発明者らは、上記各方
法について鋭意比較検討の結果、特に上記（３）に係る
方法が所期の目的を達成し得る工業的に有利な製造方法
であることを見いだし、かかる知見に基づいて本発明を
完成するに至った。Means for Solving the Problems As a result of earnest comparison and examination of the above methods, the present inventors have found that the method according to (3) above is an industrially advantageous manufacturing method that can achieve the intended purpose. It was found that there is something, and the present invention has been completed based on such findings.
【０００９】即ち、本発明に係る一般式（１）で表わさ
れるナフタレンジカルボン酸ジアミド（以下「本ジアミ
ド類」という。）の製造方法は、一般式（２）で表され
るナフタレンジカルボン酸ジアルキル（以下「本ジエス
テル類」という。）と一般式（３）で表されるアミン類
（以下「本アミン類」と総称する。）を加熱してエステ
ル・アミド交換反応せしめることを特徴とする。That is, the method for producing the naphthalenedicarboxylic acid diamide represented by the general formula (1) according to the present invention (hereinafter referred to as "the present diamides") is the dialkyl naphthalenedicarboxylic acid represented by the general formula (2) ( Hereinafter, the "present diesters") and the amines represented by the general formula (3) (hereinafter collectively referred to as "present amines") are heated to cause an ester-amide exchange reaction.
【００１０】[0010]
【化４】 ［式中、Ｒ1、Ｒ2は同一又は異なって、水素原子、アル
キル基、アルケニル基、シクロアルキル基、シクロアル
ケニル基、アリール基又はアラルキル基を表わす。ここ
で、シクロアルキル基、シクロアルケニル基、アリール
基又はアラルキル基は置換基を有していてもよい。］[Chemical 4] [In the formula, R 1 and R 2 are the same or different and each represents a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group or an aralkyl group. Here, the cycloalkyl group, cycloalkenyl group, aryl group or aralkyl group may have a substituent. ]
【００１１】[0011]
【化５】 ［式中、Ｒ3、Ｒ4は同一又は異なって、炭素数１〜４の
アルキル基を表わす。］[Chemical 5] [In the formula, R 3 and R 4 are the same or different and each represents an alkyl group having 1 to 4 carbon atoms. ]
【００１２】[0012]
【化６】 ［式中、Ｒ1、Ｒ2は一般式（１）と同義である。］[Chemical 6] [In the formula, R 1 and R 2 have the same meaning as in the general formula (1). ]
【００１３】このとき、生成する水、アルコール等を反
応系外へ除去することにより当該反応を促進させること
ができる。At this time, the reaction can be promoted by removing the produced water, alcohol, etc. from the reaction system.
【００１４】一般式（１）に係るＲ1、Ｒ2としては、特
に水素原子、炭素数１〜２０のアルキル基、炭素数２〜
２０のアルケニル基、炭素数５〜２０のシクロアルキル
基、炭素数６〜２０のアリール基及び炭素数７〜２０の
アラルキル基が推奨される。As R 1 and R 2 in the general formula (1), a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, and 2 to 2 carbon atoms are particularly preferable.
A alkenyl group having 20 carbon atoms, a cycloalkyl group having 5 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms and an aralkyl group having 7 to 20 carbon atoms are recommended.
【００１５】上記の基を有する具体的なアミド基として
は、無置換アミド［−ＣＯＮＨ2］、Ｎ−メチルアミ
ド、Ｎ−ｎ−ヘキシルアミド、Ｎ−ｎ−オクチルアミ
ド、Ｎ−シクロペンチルアミド、Ｎ−シクロヘキシルア
ミド、Ｎ−４−メチルシクロヘキシルアミド、Ｎ−２−
メチルシクロヘキシルアミド、Ｎ−フェニルアミド、Ｎ
−４−メチルフェニルアミド、Ｎ−２，６−ジメチルフ
ェニルアミド等のＮ−モノアルキル（アルケニル）又は
アリール置換アミド、Specific amide groups having the above groups include unsubstituted amide [-CONH 2 ], N-methylamide, Nn-hexylamide, Nn-octylamide, N-cyclopentylamide, N- Cyclohexylamide, N-4-methylcyclohexylamide, N-2-
Methylcyclohexylamide, N-phenylamide, N
N-monoalkyl (alkenyl)-or aryl-substituted amide such as 4-methylphenylamide, N-2,6-dimethylphenylamide,
【００１６】Ｎ，Ｎ−ジメチルアミド、Ｎ，Ｎ−ジエチ
ルアミド、Ｎ，Ｎ−ジ−ｎ−プロピルアミド、Ｎ，Ｎ−
ジシクロヘキシルアミド、Ｎ，Ｎ−ジフェニルアミド等
のＮ，Ｎ−ジアルキル（アルケニル）又はアリール置換
アミド等の基が挙げられる。N, N-dimethylamide, N, N-diethylamide, N, N-di-n-propylamide, N, N-
Examples thereof include groups such as N, N-dialkyl (alkenyl) or aryl-substituted amides such as dicyclohexylamide and N, N-diphenylamide.
【００１７】一般式（１）に係る化合物において、ナフ
タレン核に置換するアミド基の位置は特に限定されるも
のではない。しかしながら、１，５位、２，６位、２，
７位等の同一核に２個の置換基を有しない本ジアミド類
は、特に高収率で得ることができる。In the compound represented by the general formula (1), the position of the amide group substituting the naphthalene nucleus is not particularly limited. However, 1st, 5th, 2nd, 6th, 2nd
The present diamides having no two substituents in the same nucleus such as the 7-position can be obtained in particularly high yield.
【００１８】本発明に係る製造方法は、ナフタレン核に
おけるアミド基の置換位置が２，６位であり、少なくと
も１個のシクロヘキシル基を有する本ジアミド類（以下
「本シクロヘキシルジアミド類」という。）に対して特
に有効である。In the production method according to the present invention, the present diamides (hereinafter referred to as "present cyclohexyldiamides") in which the substitution position of the amide group in the naphthalene nucleus is the 2,6-position and which has at least one cyclohexyl group. On the other hand, it is particularly effective.
【００１９】本シクロヘキシルジアミド類を構成するア
ミド基としては、Ｎ−シクロヘキシルアミド、Ｎ−２−
メチルシクロヘキシルアミド、Ｎ−２−エチルシクロヘ
キシルアミド、Ｎ−４−メチルシクロヘキシルアミド、
Ｎ−４−ｎ−プロピルシクロヘキシルアミド、Ｎ−４−
tert−ブチルシクロヘキシルアミド、Ｎ−２，４−ジメ
チルシクロヘキシルアミド、Ｎ−２，４−ジエチルシク
ロヘキシルアミド等のＮ−モノシクロヘキシル置換アミ
ド基が例示される。Examples of the amide group constituting the present cyclohexyldiamide include N-cyclohexylamide and N-2-
Methylcyclohexylamide, N-2-ethylcyclohexylamide, N-4-methylcyclohexylamide,
N-4-n-propylcyclohexylamide, N-4-
Examples are N-monocyclohexyl-substituted amide groups such as tert-butylcyclohexylamide, N-2,4-dimethylcyclohexylamide, N-2,4-diethylcyclohexylamide.
【００２０】本ジエステル類としては、ナフタレンジカ
ルボン酸ジメチル、ナフタレンジカルボン酸ジエチル、
ナフタレンジカルボン酸ジプロピル、ナフタレンジカル
ボン酸ジイソプロピル、ナフタレンジカルボン酸メチル
エチル等が例示され、中でもナフタレンジカルボン酸ジ
メチルが推奨される。The diesters include dimethyl naphthalenedicarboxylate, diethyl naphthalenedicarboxylate,
Examples thereof include dipropyl naphthalene dicarboxylate, diisopropyl naphthalene dicarboxylate, and methyl ethyl naphthalene dicarboxylate, and among them, dimethyl naphthalene dicarboxylate is recommended.
【００２１】一般式（３）で表される本アミン類は、一
般式（１）のＲ1、Ｒ2に対応する一級若しくは二級の脂
肪族、脂環族又は芳香族アミンである。The present amines represented by the general formula (3) are primary or secondary aliphatic, alicyclic or aromatic amines corresponding to R 1 and R 2 of the general formula (1).
【００２２】脂肪族一級アミンとしては、メチルアミ
ン、エチルアミン、ｎ−ヘキシルアミン、ｎ−オクチル
アミン、デシルアミン、ドデシルアミン、テトラデシル
アミン、ヘキサデシルアミン、オクタデシルアミン、オ
クタデセニルアミン等が例示され、中でもｎ−ヘキシル
アミン、ｎ−オクチルアミン等が推奨される。Examples of the aliphatic primary amine include methylamine, ethylamine, n-hexylamine, n-octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, octadecenylamine and the like. Among them, n-hexylamine, n-octylamine and the like are recommended.
【００２３】脂環族一級アミンとしては、シクロペンチ
ルアミン、シクロヘキシルアミン、２−メチルシクロヘ
キシルアミン、４−メチルシクロヘキシルアミン等が例
示され、中でもシクロヘキシルアミン、２−メチルシク
ロヘキシルアミン等が推奨される。Examples of the alicyclic primary amine include cyclopentylamine, cyclohexylamine, 2-methylcyclohexylamine, 4-methylcyclohexylamine and the like. Among them, cyclohexylamine, 2-methylcyclohexylamine and the like are recommended.
【００２４】芳香族一級アミンとしては、アニリン、４
−メチルアニリン、２，４−ジメチルアニリン、２，６
−ジメチルアニリン、２，６−ジエチルアニリン、ｐ−
メトキシアニリン、ｐ−クロロアニリン等が例示され、
中でもアニリン、２，６−ジエチルアニリン等が推奨さ
れる。As the aromatic primary amine, aniline, 4
-Methylaniline, 2,4-dimethylaniline, 2,6
-Dimethylaniline, 2,6-diethylaniline, p-
Examples include methoxyaniline and p-chloroaniline,
Among them, aniline and 2,6-diethylaniline are recommended.
【００２５】脂肪族二級アミンとしては、ジメチルアミ
ン、ジエチルアミン、ジ−ｎ−プロピルアミン、ジ−ｎ
−ブチルアミン、ジ−ｎ−ヘキシルアミン等が例示さ
れ、中でもジ−ｎ−ブチルアミン、ジ−ｎ−ヘキシルア
ミン等が推奨される。As the aliphatic secondary amine, dimethylamine, diethylamine, di-n-propylamine, di-n
-Butylamine, di-n-hexylamine and the like are exemplified, and among them, di-n-butylamine, di-n-hexylamine and the like are recommended.
【００２６】脂環族二級アミンとしては、ジシクロヘキ
シルアミン、シクロヘキシルメチルアミン等が例示さ
れ、中でも ジシクロヘキシルアミンが推奨される。Examples of the alicyclic secondary amine include dicyclohexylamine, cyclohexylmethylamine and the like. Among them, dicyclohexylamine is recommended.
【００２７】芳香族二級アミンとしては、ジフェニルア
ミン、ジ（４−メチル）フェニルアミン、ジ（２，４−
ジメチル）フェニルアミン等が例示され、中でもジフェ
ニルアミン、ジ（４−メチル）フェニルアミン等が推奨
される。As the aromatic secondary amine, diphenylamine, di (4-methyl) phenylamine, di (2,4-)
Examples thereof include dimethyl) phenylamine, and among them, diphenylamine and di (4-methyl) phenylamine are recommended.
【００２８】本アミン類は、本ジエステル類に対し、通
常、２〜３０倍モル、好ましくは２〜１０倍モル程度用
いられる。The present amines are generally used in an amount of 2 to 30 times, preferably 2 to 10 times the molar amount of the present diesters.
【００２９】本反応は、無溶媒系でも行うことができる
が、通常、有機系溶媒中で行われる。This reaction can be carried out in a solvent-free system, but it is usually carried out in an organic solvent.
【００３０】当該反応溶媒としては、ベンゼン、トルエ
ン、クロルベンゼン等の芳香族系溶媒、シクロヘキサ
ン、ヘプタン等の飽和炭化水素系溶媒、ジオキサン、ジ
グライム、アニソール等のエーテル系溶媒、Ｎ−メチル
−２−ピロリドン（以下「ＮＭＰ」と略記する。）、
Ｎ，Ｎ−ジメチルアセトアミド、ジメチルスルホキシド
等の極性溶媒等が用いられる。Examples of the reaction solvent include aromatic solvents such as benzene, toluene and chlorobenzene, saturated hydrocarbon solvents such as cyclohexane and heptane, ether solvents such as dioxane, diglyme and anisole, and N-methyl-2-. Pyrrolidone (hereinafter abbreviated as "NMP"),
A polar solvent such as N, N-dimethylacetamide or dimethylsulfoxide is used.
【００３１】その溶媒量は、特に限定されるものではな
いが、通常、本ジエステル類に対して０．１〜１０倍重
量、好ましくは０．５〜５倍重量程度用いる。Although the amount of the solvent is not particularly limited, it is usually used in an amount of 0.1 to 10 times, preferably 0.5 to 5 times the weight of the diester.
【００３２】又、上記反応溶媒の代わりに過剰量の本ア
ミン類を溶媒として用いることも可能である。この方法
には後処理工程等を簡略化することができる等の有利な
面が多く好ましい。かかる場合、本ジエステル類に対
し、通常、５〜５０倍モル、好ましくは５〜１０倍モル
程度の本アミン類を用いる。Further, it is possible to use an excess amount of the present amines as a solvent instead of the above reaction solvent. This method is preferable because it has many advantageous aspects such as being able to simplify the post-treatment process and the like. In this case, the amine is usually used in an amount of 5 to 50 times, preferably 5 to 10 times the mol of the diester.
【００３３】反応温度は、通常、１００〜３００℃程
度、好ましくは１５０〜２５０℃程度である。The reaction temperature is usually about 100 to 300 ° C, preferably about 150 to 250 ° C.
【００３４】反応時間は、２〜１２時間程度、好ましく
は３〜８時間攪拌することにより目的とする本ジアミド
類を得ることができる。The desired diamides can be obtained by stirring the reaction for 2 to 12 hours, preferably 3 to 8 hours.
【００３５】又、当該反応において、必要に応じて、酸
化スズ、テトラｎ−ブトキシチタネ−ト、テトラiso−
プロポキシチタネート等の酸触媒を用いることもでき
る。In the reaction, if necessary, tin oxide, tetra-n-butoxy titanate, tetra-iso-
An acid catalyst such as propoxy titanate can also be used.
【００３６】その使用量は、本ジエステル類に対して、
０．０１〜１０重量％、好ましくは０．１〜１重量％程
度である。The amount used is based on this diester.
It is about 0.01 to 10% by weight, preferably about 0.1 to 1% by weight.
【００３７】本発明方法により得られる本ジアミド類
は、通常、針状又は板状の結晶構造を有しており、濾
過、洗浄等の後処理を効率よく行うことができる。The present diamides obtained by the method of the present invention usually have a needle-like or plate-like crystal structure, and post-treatments such as filtration and washing can be efficiently carried out.
【００３８】[0038]
【実施例】以下、実施例を掲げて本発明を詳しく説明す
る。尚、各例における反応生成物が目的とするジアミド
であることは、ＤＩ−ＭＳ及びＦＴ−ＩＲによって確認
した。EXAMPLES The present invention will be described in detail below with reference to examples. It was confirmed by DI-MS and FT-IR that the reaction product in each example was the desired diamide.
【００３９】実施例１ 温度センサー、攪拌装置を備えた５００mlオートクレー
ブに２，６−ナフタレンジカルボン酸ジメチル２０ｇ
（０．０８２モル）、シクロヘキシルアミン６０ｇ
（０．６１モル）を加え、２２０℃、６時間加熱攪拌し
た。室温まで冷却後、濾過し、得られた白色柱状固体を
イソプロパノール−水（１／１＝ｖ／ｖ）混合溶媒３０
０mlで室温下、攪拌洗浄を行なった。濾過後、１２０℃
で減圧乾燥し、２，６−ナフタレンジシクロヘキシルア
ミド（白色針状固体）３０ｇ（収率９６．８％）を得
た。Example 1 20 g of dimethyl 2,6-naphthalenedicarboxylate was added to a 500 ml autoclave equipped with a temperature sensor and a stirrer.
(0.082 mol), cyclohexylamine 60 g
(0.61 mol) was added, and the mixture was heated with stirring at 220 ° C. for 6 hours. After cooling to room temperature, the mixture was filtered, and the obtained white columnar solid was mixed with isopropanol-water (1/1 = v / v) mixed solvent 30.
The mixture was washed with 0 ml under stirring at room temperature. 120 ℃ after filtration
After drying under reduced pressure, 30 g (yield 96.8%) of 2,6-naphthalenedicyclohexylamide (white needle-shaped solid) was obtained.
【００４０】実施例２ シクロヘキシルアミンに代えて、２−メチルシクロヘキ
シルアミン７０ｇ（０．６２モル）を用いた他は実施例
１と同様の操作を行ない、２，６−ナフタレンジ−２−
メチルシクロヘキシルアミド（白色針状固体）３２．５
ｇ（収率９７．６％）を得た。Example 2 The same operation as in Example 1 was carried out except that 70 g (0.62 mol) of 2-methylcyclohexylamine was used in place of cyclohexylamine to obtain 2,6-naphthalenedi-2-.
Methyl cyclohexylamide (white needle-shaped solid) 32.5
g (yield 97.6%) was obtained.
【００４１】実施例３ シクロヘキシルアミン６０ｇに代えてシクロヘキシルア
ミン２４．４ｇ（０．２５モル）、溶媒としてＮＭＰ４
０mlを用いた他は実施例１と同様の操作を行ない、２，
６−ナフタレンジシクロヘキシルアミド（白色板状固
体）２８．６ｇ（収率９２．３％）を得た。Example 3 24.4 g (0.25 mol) of cyclohexylamine instead of 60 g of cyclohexylamine and NMP4 as a solvent
The same operation as in Example 1 was performed except that 0 ml was used.
28.6 g (yield 92.3%) of 6-naphthalenedicyclohexylamide (white plate-like solid) was obtained.
【００４２】実施例４ シクロヘキシルアミンに代えて、ｎ−ヘキシルアミン６
０ｇ（０．５９モル）とした他は実施例１と同様の操作
を行ない、２，６−ナフタレンジ−ｎ−ヘキシルアミド
（白色固体）３０．４ｇ（収率９７．１％）を得た。Example 4 Instead of cyclohexylamine, n-hexylamine 6
The same operation as in Example 1 was carried out except that the amount was changed to 0 g (0.59 mol) to obtain 30.4 g (yield 97.1%) of 2,6-naphthalenedi-n-hexylamide (white solid). .
【００４３】実施例５ シクロヘキシルアミンに代えて、アニリン６０ｇ（０．
６５モル）とした他は実施例１と同様の操作を行ない、
２，６−ナフタレンジアニリド（白色固体）３２．９ｇ
（収率９０．０％）を得た。Example 5 Instead of cyclohexylamine, 60 g of aniline (0.
65 mol) and the same operation as in Example 1 was performed,
3,6-naphthalenedianilide (white solid) 32.9 g
(Yield 90.0%) was obtained.
【００４４】実施例６ シクロヘキシルアミンに代えて、ジ（ｎ−ブチル）アミ
ン８０ｇ（０．６２モル）とした他は実施例１と同様の
操作を行ない、２，６−ナフタレンビス（ジ−ｎ−ブチ
ル）アミド３７．７ｇ（収率８６．１％）を得た。Example 6 The same operation as in Example 1 was carried out except that 80 g (0.62 mol) of di (n-butyl) amine was used instead of cyclohexylamine, and 2,6-naphthalenebis (di-n) was used. -Butyl) amide 37.7 g (yield 86.1%) was obtained.
【００４５】実施例７ シクロヘキシルアミンに代えて、ジシクロヘキシルアミ
ン１１０ｇ（０．６１モル）とした他は実施例１と同様
の操作を行ない、２，６−ナフタレンビス（Ｎ，Ｎ−ジ
シクロヘキシル）アミド４７．３ｇ（収率８７．３％）
を得た。Example 7 The same operation as in Example 1 was carried out except that 110 g (0.61 mol) of dicyclohexylamine was used instead of cyclohexylamine to obtain 2,6-naphthalenebis (N, N-dicyclohexyl) amide 47. 0.3 g (yield 87.3%)
Got
【００４６】実施例８ シクロヘキシルアミンに代えて、ジフェニルアミン１０
０ｇ（０．５９モル）とした他は実施例１と同様の操作
を行ない、２，６−ナフタレンビス（Ｎ，Ｎ−ジフェニ
ル）アミド４７．６ｇ（収率９２．０％）を得た。Example 8 Instead of cyclohexylamine, diphenylamine 10
The same operation as in Example 1 was carried out except that the amount was changed to 0 g (0.59 mol) to obtain 47.6 g (yield 92.0%) of 2,6-naphthalenebis (N, N-diphenyl) amide.
【００４７】比較例１ ２，６−ナフタレンジカルボン酸ジメチルに代えて、
２，６−ナフタレンジカルボン酸２０ｇ（０．０９３モ
ル）とした他は実施例１と同様の操作を行なったとこ
ろ、対応するアミン塩を定量的に得た。Comparative Example 1 Instead of dimethyl 2,6-naphthalenedicarboxylate,
The same operation as in Example 1 was carried out except that 20 g (0.093 mol) of 2,6-naphthalenedicarboxylic acid was used, whereby the corresponding amine salt was quantitatively obtained.
【００４８】[0048]
【発明の効果】本発明方法を適用することにより、工業
的に有用なナフタレンジカルボン酸ジアミド類を簡便、
且つ効率的に収率よく製造することができる。INDUSTRIAL APPLICABILITY By applying the method of the present invention, industrially useful naphthalene dicarboxylic acid diamides can be easily prepared.
In addition, it can be efficiently and efficiently produced.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 池田 直紀 京都府京都市伏見区葭島矢倉町13番地 新 日本理化株式会社内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Naoki Ikeda 13 Yakura-cho, Yashima-jima, Fushimi-ku, Kyoto-shi, Kyoto Inside New Nippon Rika Co., Ltd.
Claims (1)
ルボン酸ジアルキルと一般式（３）で表されるアミン類
を加熱してエステル・アミド交換反応せしめることを特
徴とする一般式（１）で表されるナフタレンジカルボン
酸ジアミドの製造方法。 【化１】 ［式中、Ｒ1、Ｒ2は同一又は異なって、水素原子、アル
キル基、アルケニル基、シクロアルキル基、シクロアル
ケニル基、アリール基又はアラルキル基を表わす。ここ
で、シクロアルキル基、シクロアルケニル基、アリール
基又はアラルキル基は置換基を有していてもよい。］ 【化２】 ［式中、Ｒ3、Ｒ4は同一又は異なって、炭素数１〜４の
アルキル基を表わす。］ 【化３】 ［式中、Ｒ1、Ｒ2は一般式（１）と同義である。］1. A general formula (1) characterized in that a dialkyl naphthalenedicarboxylic acid represented by the general formula (2) and an amine represented by the general formula (3) are heated to cause an ester / amide exchange reaction. A method for producing a naphthalene dicarboxylic acid diamide represented by: [Chemical 1] [In the formula, R 1 and R 2 are the same or different and each represents a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group or an aralkyl group. Here, the cycloalkyl group, cycloalkenyl group, aryl group or aralkyl group may have a substituent. ] [Chemical 2] [In the formula, R 3 and R 4 are the same or different and each represents an alkyl group having 1 to 4 carbon atoms. ] [Chemical 3] [In the formula, R 1 and R 2 have the same meaning as in the general formula (1). ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5092425A JP3047672B2 (en) | 1993-03-26 | 1993-03-26 | Method for producing naphthalenedicarboxylic acid diamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5092425A JP3047672B2 (en) | 1993-03-26 | 1993-03-26 | Method for producing naphthalenedicarboxylic acid diamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06279378A true JPH06279378A (en) | 1994-10-04 |
| JP3047672B2 JP3047672B2 (en) | 2000-05-29 |
Family
ID=14054082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5092425A Expired - Fee Related JP3047672B2 (en) | 1993-03-26 | 1993-03-26 | Method for producing naphthalenedicarboxylic acid diamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3047672B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106316877A (en) * | 2015-06-18 | 2017-01-11 | 中国石油化工股份有限公司 | Preparation method of dicyclohexylterephthalamide |
-
1993
- 1993-03-26 JP JP5092425A patent/JP3047672B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106316877A (en) * | 2015-06-18 | 2017-01-11 | 中国石油化工股份有限公司 | Preparation method of dicyclohexylterephthalamide |
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| Publication number | Publication date |
|---|---|
| JP3047672B2 (en) | 2000-05-29 |
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