7195-44-0

Basic information

• Product Name: bis(2,3-epoxypropyl) terephthalate
• Synonyms: bis(2,3-epoxypropyl) terephthalate;Terephthalic acid diglycidyl ester;1,4-Benzenedicarboxylic acid, bis(oxiranylmethyl) ester;diglycidyl terephthalate;Telephthalic acid diglycidyl;Terephthalic acid bis(2,3-epoxypropan-1-yl) ester;Terephthalic acid bis[(oxiranyl)methyl] ester;Terephthalic acid bisglycidyl ester
• CAS NO: 7195-44-0
• Molecular Formula: C₁₄H₁₄O₆
• Molecular Weight: 278.25736
• EINECS: 230-565-0
• Mol File: 7195-44-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 426.2°C at 760 mmHg
• Flash Point: 191.1°C
• Appearance: /
• Density: 1.351g/cm³
• Vapor Pressure: 1.8E-07mmHg at 25°C
• Refractive Index: 1.569
• Water Solubility: 77mg/L at 20℃
• CAS DataBase Reference: bis(2,3-epoxypropyl) terephthalate(CAS DataBase Reference)
• NIST Chemistry Reference: bis(2,3-epoxypropyl) terephthalate(7195-44-0)
• EPA Substance Registry System: bis(2,3-epoxypropyl) terephthalate(7195-44-0)

Safety Data

• Hazardous Substances Data: 7195-44-0(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C14H14O6/c15-13(19-7-11-5-17-11)9-1-2-10(4-3-9)14(16)20-8-12-6-18-12/h1-4,11-12H,5-8H2

Synthetic route

terephthalic acid (100-21-0) + epichlorohydrin (106-89-8) → terephthalic acid diglycidyl ester (7195-44-0)

Conditions	Yield
Stage #1: terephthalic acid; epichlorohydrin With n-butyl(triphenyl)phosphonium bromide In N,N-dimethyl-formamide at 100℃; for 5h; Large scale; Stage #2: With sodium hydroxide In dichloromethane at 40℃; for 5h; Solvent; Temperature; Reagent/catalyst; Time; Large scale;	91.9%
Stage #1: terephthalic acid; epichlorohydrin With cetyltrimethylammonium chloride at 90℃; for 3h; Stage #2: With sodium hydroxide In water at 30℃; for 6h;	80%

sodium tungstate (VI) dihydrate (10213-10-2) + diallyl terephthalate (1026-92-2) + Aliquat 336 (5137-55-3) → terephthalic acid diglycidyl ester (7195-44-0)

Conditions	Yield
With phosphoric acid; dihydrogen peroxide In water; toluene	85%

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + oxiranyl-methanol (556-52-5) → terephthalic acid diglycidyl ester (7195-44-0)

Conditions	Yield
With polystyrene supported trioctyl methyl ammonium chloride In hexane at 80℃; for 5h; Reagent/catalyst;	77%
With tridodecylmethylammonium chloride In hexane; toluene at 69℃; for 3h;	64%

C14H16Cl2O6 → terephthalic acid diglycidyl ester (7195-44-0)

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 20℃; for 3h;
With sodium hydroxide In dichloromethane at 40℃; for 6h; Solvent; Temperature;	1.49 g

Upstream product

• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 556-52-5 oxiranyl-methanol 
• 100-21-0 terephthalic acid 
• 106-89-8 epichlorohydrin 
• 10213-10-2 sodium tungstate (VI) dihydrate 
• 1026-92-2 diallyl terephthalate 
• 5137-55-3 Aliquat 336 

Relevant articles and documents

Synthesis and properties of a bio-based epoxy resin from 2,5-furandicarboxylic acid (FDCA)

A bio-based epoxy monomer, diglycidyl ester of 2,5-furandicarboxylic acid (DGF) was synthesized for the first time from the renewable 2,5-furandicarboxylic acid (FDCA). For comparison study, its petroleum-based counterpart, diglycidyl ester of terephthalic acid (DGT) was also prepared. Their chemical structures were confirmed in detail by 1H NMR, 13C NMR and FT-IR before they were cured by methylhexahydrophthalic anhydride (MHHPA) and poly(propylene glycol)bis(2-aminopropyl ether) (D230), respectively. The curing behaviors were investigated using differential scanning calorimetry (DSC). The thermal mechanical properties and thermal stabilities of the cured resins were evaluated using dynamic mechanical analysis (DMA) and thermogravimetric analysis (TGA). Results showed that DGF displayed higher curing activity, elevated glass transition temperature and similar mechanical properties compared with those of the cured DGT. This study indicated that FDCA had a huge potential to replace the petroleum-based terephthalic acid in the synthesis of epoxy resins with satisfactory performance.

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.

METHOD FOR PRODUCING GLYCIDYL ESTER

PROBLEM TO BE SOLVED: To provide a production method which makes it possible to obtain glycidyl ester with high yields from the ester exchange reaction between ester and glycidol with a convenient catalyst in a mild reaction condition. SOLUTION: Glycidyl ester is produced by the ester exchange reaction between ester and glycidol in the presence of a polystyrene-carrying quaternary ammonium salt. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT