Synthesis of Arylmelamines. II. Synthesis of Diarylmelamines

Itaru HONDA

doi:10.5059/yukigoseikyokaishi.20.460

Synthesis of Arylmelamines. II.

Synthesis of Diarylmelamines

Itaru HONDA

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JOURNAL FREE ACCESS

1962 Volume 20 Issue 5 Pages 460-465

DOI https://doi.org/10.5059/yukigoseikyokaishi.20.460

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Published: May 01, 1962 Received: July 29, 1962 Available on J-STAGE: June 28, 2010 Accepted: - Advance online publication: - Revised: -
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Date of correction: June 28, 2010 Reason for correction: - Correction: DTRECEIVED Details: Right : 19620729

Date of correction: June 28, 2010 Reason for correction: - Correction: ABSTRACT Details: Wrong : Reaction of 2-amino-4, 6-dichloro-s-triazine and aromatic amines by a general method of refluxing for 2hrs, in water while neutralizing reaction solution yielded over 90% of diaryl-melamines in case of 4 kinds of liquid aromatic amines at room temperature. However, this method was unsuitable for reacton of 5 kinds of solid aromatic amines at room temperature. On the other hand, keeping of reacting solution weakly acidic and changing the time of reaction gave an improvement in yield over 90% in case of using of solid amines. Also it was found that an addition of neutralizing agent was not always necessary. Among 10 kinds of synthesized diarylmelamines, di-o-, -m-, and -p-toluylmelamines, mp 194-5°c, 139-40°c and 289-90°c, respectively, di-p-biphenylylmelamine, mp 278-9°c, di-β-naphthylmelamine, mp 217°c (8 hrs reaction), bis-p-acetylaminophenylmelamine, mp 300-1°c (10 min, reaction), and bis-p-aminophenylmelamine, mp 243-4°c (prepared by hydrolysis of the acetyl compound), are new compounds.
Right : Reaction of 2-amino-4, 6-dichloro-s-triazine and aromatic amines by a general method of refluxing for 2hrs, in water while neutralizing reaction solution yielded over 90% of diaryl-melamines in case of 4 kinds of liquid aromatic amines at room temperature. However, this method was unsuitable for reacton of 5 kinds of solid aromatic amines at room temperature. On the other hand, keeping of reacting solution weakly acidic and changing the time of reaction gave an improvement in yield over 90% in case of using of solid amines. Also it was found that an addition of neutralizing agent was not always necessary. Among 10 kinds of synthesized diarylmelamines, di-o-, -m-, and -p-toluylmelamines, mp 194-5°C, 139-40°C and 289-90°C, respectively, di-p-biphenylylmelamine, mp 278-9°C, di-β-naphthylmelamine, mp 217°C (8 hrs reaction), bis-p-acetylaminophenylmelamine, mp 300-1°C (10 min, reaction), and bis-p-aminophenylmelamine, mp 243-4°C (prepared by hydrolysis of the acetyl compound), are new compounds.

Abstract

Reaction of 2-amino-4, 6-dichloro-s-triazine and aromatic amines by a general method of refluxing for 2hrs, in water while neutralizing reaction solution yielded over 90% of diaryl-melamines in case of 4 kinds of liquid aromatic amines at room temperature. However, this method was unsuitable for reacton of 5 kinds of solid aromatic amines at room temperature. On the other hand, keeping of reacting solution weakly acidic and changing the time of reaction gave an improvement in yield over 90% in case of using of solid amines. Also it was found that an addition of neutralizing agent was not always necessary. Among 10 kinds of synthesized diarylmelamines, di-o-, -m-, and -p-toluylmelamines, mp 194-5°C, 139-40°C and 289-90°C, respectively, di-p-biphenylylmelamine, mp 278-9°C, di-β-naphthylmelamine, mp 217°C (8 hrs reaction), bis-p-acetylaminophenylmelamine, mp 300-1°C (10 min, reaction), and bis-p-aminophenylmelamine, mp 243-4°C (prepared by hydrolysis of the acetyl compound), are new compounds.

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