2451-62-9

Basic information

• Product Name: 1,3,5-Triglycidyl isocyanurate
• Synonyms: 6(1h,3h,5h)-trione,1,3,5-tris(2,3-epoxypropyl)-s-triazine-4;6(1h,3h,5h)-trione,tris(2,3-epoxypropyl)-s-triazine-4;glycidylisocyanurate;n,n’,n’’-triglycidylisocyanurate;tgt;tri(Epoxypropyl)isocyanurate;triglycidyl;tris(epoxypropyl)isocyanurate
• CAS NO: 2451-62-9
• Molecular Formula: C₁₂H₁₅N₃O₆
• Molecular Weight: 297.26
• EINECS: 219-514-3
• Product Categories: Oxiranes;Simple 3-Membered Ring Compounds;curing agent
• Mol File: 2451-62-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 95-98°C
• Boiling Point: 438.78°C (rough estimate)
• Flash Point: 256.9 °C
• Appearance: white crystalline solid
• Density: 1,42 g/cm3
• Vapor Pressure: 3.56E-10mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• PKA: -2.44±0.20(Predicted)
• Water Solubility: <0.1 g/100 mL at 20℃
• CAS DataBase Reference: 1,3,5-Triglycidyl isocyanurate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Triglycidyl isocyanurate(2451-62-9)
• EPA Substance Registry System: 1,3,5-Triglycidyl isocyanurate(2451-62-9)

Safety Data

• Hazard Codes: T
• Statements: 46-23/25-41-43-48/22-52/53
• Safety Statements: 53-45-61
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: XZ1994900
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 2451-62-9(Hazardous Substances Data)

Usage

Industrial Application

1,3,5-triglycidyl isocyanurate (TGIC) is a white powder or granular solid and is normally sold under the trade name ARALDITE PT810R or TEPIC G R. As a tri-functional epoxy monomer, TGIC is used in large scale as curing agent for powder coatings or for cross-linking elastomers. Rosin acids of natural origin may also be cured with TGIC for versatile applications. TGIC has also been used for pharmaceutical purposes, in membranes, for curing intelligent gels or liquid crystal elastomers. Especially, this curing agent has been widely used in dry powder coating for over 40 years.

Health Toxicity

It has been known that TGIC is toxic by inhalation and if swallowed. It is a severe eye irritant, and a mild skin and nasal irritant, although it has the potential to cause skin sensitisation in people which can lead to severe skin rashes. Exposure to TGIC in powder paints may cause not only contact dermatitis, but also occupational asthma. Kidney damage has also been observed in rats repeatedly exposed to TGIC by oral dosing, and damage to the developing sperm cells has been observed in mice repeatedly exposed to TGIC orally and by inhalation. There is an evidence that exposure of males to TGIC produces genetic changes in the sperm which may lead to heritable effects in the offspring. There is cause for concern that these effects could occur in humans, so that TGIC has been classified in the EU as a Category 2 mutagen. Exposures to TGIC during manufacturing procedures have been identified as hazardous to workers.

Description

Occupational contact dermatitis can occur in people producing this chemical, in those producing the powder coat paint and in sprayers.

Chemical Properties

White powder or chunks

Uses

Different sources of media describe the Uses of 2451-62-9 differently. You can refer to the following data:
1. 1,3,5-triglycidyl isocyanurate be used for curing agent of polyester and acrylic resin carboxyl-containing powder coating, manufacturing an electrical insulating laminates, adhesives, plastics stabilizers.
2. TGIC is widely used as a cross-linking agent or curing agent in powder coating industry, It is used also in the printed circuit board industry, electrical insulation and as a stabilizer in plastic industry. Typical applications of polyester TGIC powder coatings are where sharp edges and corners exist such as on automotive wheels, air conditioners, lawn furniture, and air conditioner cabinets.
3. Triglycidyl isocyanurate is used as cross-linker in heat-cured polyester paints, such as laminated sheetings, printed circuits, tools, inks, adhesives, lining materials etc.

General Description

White crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Fire Hazard

Flash point data for 1,3,5-Triglycidyl isocyanurate are not available; however, 1,3,5-Triglycidyl isocyanurate is probably combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

Triglycidyl isocyanurate is a triazine epoxy compound used as a resin hardener in polyester powder paints, in the plastics industry, resin molding systems, inks, and adhesives. Occupational contact dermatitis can occur in people producing this chemical, in those producing the powder coat paint, and in sprayers. Respiratory symptoms have been observed.

InChI:InChI=1/C12H15N3O6/c16-10-13(1-7-4-19-7)11(17)15(3-9-6-21-9)12(18)14(10)2-8-5-20-8/h7-9H,1-6H2

Synthetic route

sodium isocyanate (917-61-3) + epichlorohydrin (106-89-8) → teroxirone (2451-62-9)

Conditions	Yield
With dihydrogen peroxide; benzyl bromide In dimethyl sulfoxide at 20 - 70℃; for 4h; Reagent/catalyst; Solvent; Temperature;	85%

cyanuric acid (108-80-5) + epichlorohydrin (106-89-8) → teroxirone (2451-62-9)

Conditions	Yield
Stage #1: cyanuric acid With sodium hydroxide at 60℃; pH=7.5; Stage #2: epichlorohydrin With benzyltrimethylammonium chloride at 115 - 120℃; for 7.5h; Catalytic behavior; Temperature;	84%
Stage #1: cyanuric acid; epichlorohydrin With benzyltrimethylammonium chloride In water Autoclave; Heating; Stage #2: With sodium hydroxide In dichloromethane	67%

triallyl isocyanurate (1025-15-6) → teroxirone (2451-62-9)

Conditions	Yield
With sodium phosphate dodecahydrate; dihydrogen peroxide; sodium hydrogencarbonate; sodium carbonate In methanol; water; acetonitrile at 20℃; for 15h; pH=10.6;

1,3,5-tris-(3-chloro-2-hydroxy-propyl)-[1,3,5]triazinane-2,4,6-trione (7423-53-2) → teroxirone (2451-62-9)

Conditions	Yield
With sodium hydroxide In methanol at 15℃; for 1.5h; Temperature; Solvent; Large scale;
With potassium hydroxide In water at 35 - 50℃; for 4h; Temperature; Reagent/catalyst;

isocyanuric acid (108-80-5) + epichlorohydrin (106-89-8) → teroxirone (2451-62-9)

Conditions	Yield
Stage #1: isocyanuric acid; epichlorohydrin With N-benzyl-N,N,N-triethylammonium chloride at 80℃; Stage #2: With sodium hydroxide at 15℃; for 1h; Temperature;

1,3-Dichloro-2-propanol (96-23-1) + isocyanuric acid (108-80-5) → teroxirone (2451-62-9)

Conditions	Yield
With sodium hydroxide In water at 55 - 80℃; for 5h; Reagent/catalyst; Temperature;

4-ethoxycarbonylpiperazine (120-43-4) + teroxirone (2451-62-9) → carboxylate protected tris(2,3-epoxypropyl)isocyanurate

Conditions	Yield
In methanol; 1,2-dimethoxyethane at 25℃; for 51h;	100%

Mono(2-methacryloyloxy)ethylphthalate + teroxirone (2451-62-9) → THPICTHP

Conditions	Yield
Stage #1: Mono(2-methacryloyloxy)ethylphthalate; teroxirone With triphenylantimony at 100℃; for 5h; Stage #2: With triphenylphosphine at 100℃; for 3h;	100%

teroxirone (2451-62-9) + diallylamine (124-02-7) → 1,3,5-tris-(3-diallylamino-2-hydroxy-propyl)-[1,3,5]triazine-2,4,6-trione

Conditions	Yield
In methanol for 24h; Heating / reflux;	98.6%
In methanol at 60℃; for 24h;	96.6%

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE (36768-62-4) + teroxirone (2451-62-9) → tris[2-hydroxy-3-(2,2,6,6-tetramethyl-4-piperidylamino)propyl] isocyanurate (144923-25-1)

Conditions	Yield
	97.4%

2,4-Xylenol (105-67-9) + teroxirone (2451-62-9) → metaxalone (1665-48-1)

Conditions	Yield
With potassium hydroxide; 4-methyl-2-pentanone at 0 - 120℃; for 3 - 4h;	97%

pentaerythritol triacrylate (3524-68-3) + teroxirone (2451-62-9) → C66H81N3O36

Conditions	Yield
With 4-methoxy-phenol; triphenylphosphine at 95℃; for 14h;	94.58%

dibutylamine (111-92-2) + teroxirone (2451-62-9) → tris(dibutylaminoglycidyl) isocyanurate

Conditions	Yield
In ethanol at 20 - 78℃; for 48h; Inert atmosphere;	90.85%

C22H28O10 + teroxirone (2451-62-9) → C81H105N3O36

Conditions	Yield
With triphenyl phosphite; 4-methoxy-phenol; triethylamine at 95℃; for 14h;	85.6%

N-methylaniline (100-61-8) + teroxirone (2451-62-9) → 1,3,5-tris(2-hydroxy-3-(methyl(phenyl)amino)propyl)-1,3,5-triazinane-2,4,6-trione (1335044-85-3)

Conditions	Yield
at 110℃; for 8h;	85%
at 110℃; for 8h;

2-((3,5-dimethylphenyl)amino)ethanol (857035-61-1) + teroxirone (2451-62-9) → C42H60N6O9 (1335044-87-5)

Conditions	Yield
at 110℃; for 8h;	85%

3,5-dimethyl-N-ethylaniline (13342-22-8) + teroxirone (2451-62-9) → C42H60N6O6 (1335044-86-4)

Conditions	Yield
at 110℃; for 8h;	83%

teroxirone (2451-62-9) + 3,5-Dimethylphenol (108-68-9) → metaxalone (1665-48-1)

Conditions	Yield
With sodium hydroxide In water; ethyl acetate; acetone	81%
Stage #1: 3,5-Dimethylphenol With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In 1-methyl-pyrrolidin-2-one; 4-methyl-2-pentanone at 40℃; for 0.5h; Stage #2: teroxirone In 1-methyl-pyrrolidin-2-one; 4-methyl-2-pentanone at 100 - 120℃; for 4.5h; Product distribution / selectivity;	65%

teroxirone (2451-62-9) + 2-Anilinoethanol (122-98-5) → 1,3,5-tris(2-hydroxy-3-((2-hydroxyethyl)(phenyl)amino)propyl)-1,3,5-triazinane-2,4,6-trione (1443765-28-3)

Conditions	Yield
at 110℃;	75%

teroxirone (2451-62-9) + 4-Hydroxybenzophenone (1137-42-4) → anilazine (101-05-3)

Conditions	Yield
With triphenylphosphine In chloroform	70%

teroxirone (2451-62-9) + 4-Hydroxybenzophenone (1137-42-4) → C51H45N3O12 (917248-81-8)

Conditions	Yield
triphenylphosphine at 130℃; for 0.0333333h; Inert atmosphere;	70%
Stage #1: teroxirone; 4-Hydroxybenzophenone With triphenylphosphine at 130℃; Inert atmosphere; Stage #2: With triphenylphosphine for 0.0333333h; Inert atmosphere;	70%
With triphenylphosphine at 130℃; for 0.0333333h; Inert atmosphere;	70%

propionic acid (802294-64-0) + teroxirone (2451-62-9) → Propionic acid 3-(3,5-bis-oxiranylmethyl-2,4,6-trioxo-[1,3,5]triazinan-1-yl)-2-hydroxy-propyl ester

Conditions	Yield
	68%

Cyasorb UV531 (1843-05-6) + teroxirone (2451-62-9) → C75H93N3O15 (920017-65-8)

Conditions	Yield
Stage #1: Cyasorb UV531; teroxirone at 130℃; for 0.166667h; Inert atmosphere; Stage #2: With triphenylphosphine for 72h; Inert atmosphere;	68%

teroxirone (2451-62-9) → 1,3,5-tris(3-azido-2-hydroxypropyl)-1,3,5-triazinane-2,4,6-trione (1000416-74-9)

Conditions	Yield
With sodium azide; ammonium chloride In water; N,N-dimethyl-formamide at 20℃;	55%

carbon disulfide (75-15-0) + teroxirone (2451-62-9) → 1,3,5-tris[(2-thioxo-1,3-oxathiolan-5-yl)methyl]-1,3,5-triazinane-2,4,6-trione

Conditions	Yield
With lithium bromide In acetonitrile at 20℃; for 24h;	44%

1-deoxy-1-(methylamino)-D-glucitol (6284-40-8) + teroxirone (2451-62-9) → 1,3,5-tris{2-hydroxy-3-[N-methyl-(2',3',4',5',6'-pentahydroxy-D-gluco-hexyl)amino]propyl}-(1H,3H,5H)-1,3,5-triazin-2,4,6-trione

Conditions	Yield
In ethanol for 7h; Reflux;	40%

morpholine (110-91-8) + teroxirone (2451-62-9) → Diglycidyl-(2-hydroxy-3-N-morpholinopropyl) isocyanurate

Conditions	Yield
	30%

propan-1-ol (71-23-8) + teroxirone (2451-62-9) → diglycidyl-(2-hydroxy-3-propoxypropyl)isocyanurate

Conditions	Yield
	23%

methacryloyl anhydride (760-93-0) + teroxirone (2451-62-9) → 1,3-diglycidyl-5-(2,3-dimethacryloyloxy)propyl isocyanurate

Conditions	Yield
With benzyltrimethylammonium chloride; 4-methoxy-phenol In toluene at 80℃; for 10h;	21.6%

teroxirone (2451-62-9) + recorcinol (108-46-3) → m-bis(2-oxooxazolidin-5-ylmethoxy)benzene

Conditions	Yield
sodium hydroxide

Octanethiol (111-88-6) + teroxirone (2451-62-9) → Diglycidyl-2-hydroxy-3-n-octylthio-propyl isocyanurate

Conditions	Yield
With triethylamine In methanol

Upstream product

• 96-23-1 1,3-Dichloro-2-propanol 
• 108-80-5 isocyanuric acid 
• 106-89-8 epichlorohydrin 
• 7423-53-2 1,3,5-tris-(3-chloro-2-hydroxy-propyl)-[1,3,5]triazinane-2,4,6-trione 
• 1025-15-6 triallyl isocyanurate 
• 108-80-5 cyanuric acid 
• 917-61-3 sodium isocyanate 

Downstream Products

• 1443765-28-3 1,3,5-tris(2-hydroxy-3-((2-hydroxyethyl)(phenyl)amino)propyl)-1,3,5-triazinane-2,4,6-trione 
• 681258-76-4 C₃₃H₃₀Cl₃N₃O₁₂ 
• 681258-74-2 C₃₃H₃₃N₃O₁₅ 
• 948994-02-3 C₄₂H₃₆N₆O₁₅ 
• 1335044-86-4 C₄₂H₆₀N₆O₆ 
• 1335044-87-5 C₄₂H₆₀N₆O₉ 
• 920017-65-8 C₇₅H₉₃N₃O₁₅ 
• 1335044-85-3 1,3,5-tris(2-hydroxy-3-(methyl(phenyl)amino)propyl)-1,3,5-triazinane-2,4,6-trione 
• 1048964-64-2 N,N,N'-tris-(3-{acetyl-[3,5-bis-(2 3-dihydroxy-propyl-carbamoyl)-2,4,6-triiodo-phenyl]-amino}-2-hydroxy-propyl)-dicarbonimidic diamide 
• 1665-48-1 metaxalone 
• 101-05-3 anilazine 
• 917248-81-8 C₅₁H₄₅N₃O₁₂ 

Relevant articles and documents

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Preparation method of triglycidyl isocyanurate

The invention relates to a preparation method of triglycidyl isocyanurate. The preparation method comprises the steps that cyanuric acid and dichloropropanol are subjected to a heating reaction in thepresence of alkali and a solvent, the molar ratio of cyanuric acid to dichloropropanol is 1: 2 to 8, and the molar ratio of the addition amount of alkali to the addition amount of dichloropropanol is2: 1. The raw material conversion rate of the triglycidyl isocyanurate prepared by the method is high and reaches 95% or above, the product selectivity is good and reaches 95% or above, and the product yield is high and reaches 90% or above and is far higher than the yield of about 80% in the prior art.

Method for synthesizing TGIC and coproducing ECH from dichloropropanol

The invention provides a method for synthesizing TGIC and coproducing ECH from dichloropropanol. The method comprises the following steps: (1) proportionally adding cyanuric acid, dichloropropanol, aquaternary ammonium salt phase transfer catalyst and water, heating and stirring the mixture and carrying out temperature control reaction in stages, heating and stirring the mixture to a certain temperature, carrying out heat preservation reaction for a period of time, heating the mixture, carrying out heat preservation reaction for a period of time, and cooling a reaction product; (2) in the reaction system in the step (1), adjusting the vacuum degree, dropwise adding liquid caustic soda while carrying out steam stripping with water within a certain period of time, carrying out heat preservation reaction for a period of time after dropwise adding is finished, and then removing solid salt through plate-and-frame filter pressing; (3) carrying out reduced pressure distillation on the filtrate obtained in the step (2) to remove ECH, and collecting a crude product TGIC from the kettle liquid; (4) recrystallizing the crude product TGIC in an organic solvent for a period of time under a low-temperature condition, and then centrifugally separating, washing and drying the product to obtain a TGIC product. According to the treatment method disclosed by the invention, the cost of TGIC can be effectively reduced, an important organic chemical raw material ECH is co-produced, and the method is low-carbon and environment-friendly.