7176-19-4

Basic information

• Product Name: tris(oxiranylmethyl) benzene-1,3,5-tricarboxylate
• Synonyms: tris(oxiranylmethyl) benzene-1,3,5-tricarboxylate;1,3,5-Benzenetricarboxylic acid tris(oxiranylmethyl) ester;tris(oxiran-2-ylmethyl)benzene-1,3,5-tricarboxylate;5-((tri(oxiran-2-yl)methoxy)carbonyl)isophthalic acid
• CAS NO: 7176-19-4
• Molecular Formula: C₁₈H₁₈O₉
• Molecular Weight: 378.33012
• EINECS: 230-536-2
• Mol File: 7176-19-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 537.5°C at 760 mmHg
• Flash Point: 237.6°C
• Appearance: /
• Density: 1.432g/cm³
• Vapor Pressure: 1.27E-11mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: tris(oxiranylmethyl) benzene-1,3,5-tricarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tris(oxiranylmethyl) benzene-1,3,5-tricarboxylate(7176-19-4)
• EPA Substance Registry System: tris(oxiranylmethyl) benzene-1,3,5-tricarboxylate(7176-19-4)

Safety Data

• Hazardous Substances Data: 7176-19-4(Hazardous Substances Data)

Usage

General Description

Tris(oxiranylmethyl) benzene-1,3,5-tricarboxylate, also known as tris(3-glycidyloxypropyl) isocyanurate (TGIC), is a chemical compound used primarily as a crosslinking agent in the production of powder coatings. It is a tri-functional epoxide with three oxirane groups, and its benzene tricarboxylate structure provides a high level of thermal stability and chemical resistance. TGIC is commonly used in industrial and commercial applications due to its excellent adhesion and mechanical properties, making it a crucial component in the production of durable and highly resistant coatings for metal surfaces. However, it is important to handle and use TGIC with caution, as it can cause skin and eye irritation and may be harmful if inhaled or ingested.

InChI:InChI=1/C18H18O9/c19-16(25-7-13-4-22-13)10-1-11(17(20)26-8-14-5-23-14)3-12(2-10)18(21)27-9-15-6-24-15/h1-3,13-15H,4-9H2

Upstream product

• 17832-16-5 triallyl benzene-1,3,5-tricarboxylate 
• 554-95-0 benzene-1,3,5-tricarboxylic acid 
• 2672-58-4 1,3,5-tris-(methoxycarbonyl)benzene 
• 556-52-5 oxiranyl-methanol 

Relevant articles and documents

Quaternary Alkyl Ammonium Salt-Catalyzed Transformation of Glycidol to Glycidyl Esters by Transesterification of Methyl Esters

Catalytic transformation of glycidol while maintaining its epoxide moiety intact is challenging because the terminal epoxide that interacts with the hydroxyl group via a hydrogen bond is labile for the ring-opening reaction. We found that a quaternary alkyl ammonium salt catalyzes the selective transformation of glycidol to glycidyl esters by transesterification of methyl esters. The developed method can be applied to the synthesis of multiglycidyl esters, which are valuable epoxy resin monomers. Mechanistic studies revealed the formation of a binding complex of glycidol and quaternary alkyl ammonium salt in a nonpolar solvent and the generation of the alkoxide anion as a catalyst through the ring-opening reaction of the epoxide. Computational studies of the reaction mechanism indicated that the alkoxide anion derived from glycidol tends to abstract the proton of another glycidol rather than work as a nucleophile, initiating the catalytic transesterification. Payne rearrangement of the deprotonated glycidol, which produces a destabilized base that promotes nonselective reactions, is energetically unfavorable due to the double hydrogen bond between the anion and diol. The minimal interaction between the quaternary alkyl ammonium cation and the epoxide moiety inhibited the random ring-opening pathway leading to polymerization.