1025-15-6

Usage

Chemical Properties

colourless viscous liquid or white powder

Uses

Different sources of media describe the Uses of 1025-15-6 differently. You can refer to the following data:
1. crosslinking accelerator agent for peroxide
2. The Progress in Development of Dental Restorative Materials

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 4931, 1994 DOI: 10.1021/jo00096a041

General Description

White crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Isocyanates and thioisocyanates, such as 1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].

Fire Hazard

1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione is probably combustible.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H15N3O3/c1-4-7-13-10(16)14(8-5-2)12(18)15(9-6-3)11(13)17/h4-6H,1-3,7-9H2

Synthetic route

cyanuric acid (108-80-5) + allyl alcohol (107-18-6) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 95℃; for 22h; Reagent/catalyst; Inert atmosphere;	98.6%

allylisocyanate (1476-23-9) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene at 20℃; for 1h;	98%
With tetraethylammonium 2-(carbamoyl)benzoate at 50℃; for 6h; Neat (no solvent);	95%
With 1,3-dimethyl-4,5-diphenyl-2-(propan-2-ylidene)-2,3-dihydro-1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 48h; Inert atmosphere; Glovebox;	89%

allyl bromide (106-95-6) + isocyanuric acid (108-80-5) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
Stage #1: isocyanuric acid With tetrabutylammomium bromide; triethylamine; copper(l) chloride In 1,2-dichloro-ethane at 80℃; Large scale; Stage #2: allyl bromide In 1,2-dichloro-ethane at 80℃; for 6.5h; Temperature; Large scale;	93.2%

allyl tosylate (4873-09-0) + sodium isocyanate (917-61-3) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20 - 60℃; for 4.17h; Solvent; Reagent/catalyst; Green chemistry;	93%

triallyl cyanurate (101-37-1) → allyl chloroacetate (2916-14-5) + 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione (6294-79-7) + triallyl isocyanurate (1025-15-6)

Conditions	Yield
With chloroacetic acid In toluene for 2h; Heating; Yields of byproduct given;	A n/a B 91.5% C n/a
With chloroacetic acid In toluene for 2h; Heating; Yield given. Yields of byproduct given;

E/Z-1,3-Dichloropropene (542-75-6) + sodium isocyanate (917-61-3) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With calcium chloride; potassium bromide In N,N-dimethyl-formamide at 120℃;	91%
With calcium chloride; potassium bromide In N,N-dimethyl-formamide at 120℃; Product distribution / selectivity;

triallyl cyanurate (101-37-1) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
copper(II) chloride hydrate In xylene at 120℃; for 2h;	90%
With copper(II) choride dihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 65 - 75℃; Inert atmosphere;	90%
copper dichloride In toluene at 113 - 140℃; under 1.50015 - 2.25023 Torr; Product distribution / selectivity;

triallyl cyanurate (101-37-1) → Allyl acetate (591-87-7) + 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione (6294-79-7) + triallyl isocyanurate (1025-15-6)

Conditions	Yield
With acetic acid In toluene for 2h; Heating; Yields of byproduct given;	A n/a B 85% C n/a
With acetic acid In toluene for 2h; Heating; Yield given. Yields of byproduct given;

triallyl cyanurate (101-37-1) → Allyl ether (557-40-4) + 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione (6294-79-7) + triallyl isocyanurate (1025-15-6)

Conditions	Yield
With allyl alcohol In toluene for 2h; Heating; Yields of byproduct given;	A n/a B 81.5% C n/a
With allyl alcohol In toluene for 2h; Heating; Yield given. Yields of byproduct given;

1,3,5-Triallyl-[1,3,5]triazinane-2,4,6-triylidenetriamine → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With hydrogenchloride In water for 5h; Heating;	77%

cyanuric acid (108-80-5) + allyl alcohol (107-18-6) → 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione (6294-79-7) + triallyl isocyanurate (1025-15-6)

Conditions	Yield
With triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 95℃; for 8h; Time; Reagent/catalyst; Solvent; Inert atmosphere;	A 13% B 68.1%

cyanuric acid (108-80-5) + allyl mesylate (6728-21-8) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With sodium carbonate; potassium bromide In dimethyl sulfoxide at 65℃; for 1.5h;	68%

triallyl cyanurate (101-37-1) + 2,4,6-tris(methallyloxy)-1,3,5-triazine (16715-84-7) → triallyl isocyanurate (1025-15-6) + 1-(allyl)-3,5-bis(2-methylprop2-en-1-yl)isocyanurate (118361-38-9) + 1-(2-methylprop-2-en-1-yl)-3,5-bis(3-propenyl)isocyanurate (73669-73-5) + tris-2-methylprop-2-en-1-ylisocyanurate (6291-95-8)

Conditions	Yield
With CuCl2.2H2O In toluene for 4h; Heating;	A 18.5% B 31.7% C 40.4% D 9.4%
at 190 - 200℃; for 5h;	A 23.3% B 31.6% C 24% D 21.1%
at 190 - 200℃; for 5h;	A 23.3% B 31.6% C 24% D 21.1%

potassium cyanate (590-28-3) + 3-chloroprop-1-ene (107-05-1) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With acetonitrile at 150℃;

potassium cyanate (590-28-3) + 3-chloroprop-1-ene (107-05-1) + acetonitrile (75-05-8) → 1,3-diallylurea (1801-72-5) + triallyl isocyanurate (1025-15-6)

Conditions	Yield
at 150℃;

cyanuric acid (108-80-5) + 3-chloroprop-1-ene (107-05-1) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With sodium hydride 1.) HMPA, 100 deg C, 3 h, 2.) HMPA, 100 deg C, 3 h; Yield given. Multistep reaction;

1,3,5-Triallyl-[1,3,5]triazinane-2,4-dione → 1,3,5-triallyl-6-hydroperoxy-[1,3,5]triazinane-2,4-dione + triallyl isocyanurate (1025-15-6)

Conditions	Yield
With oxygen In chlorobenzene at 70℃;

cyanuric acid (108-80-5) + allyl bromide (106-95-6) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20 - 80℃;
With magnesium sulfate; potassium carbonate In dimethyl sulfoxide; ethyl acetate

sodium isocyanate (917-61-3) + 3-chloroprop-1-ene (107-05-1) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
With sodium hydrogen sulfate In dimethyl sulfoxide at 95℃; Temperature;

sodium cyanurate (3047-33-4) + allyl bromide (106-95-6) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
In N,N-dimethyl-formamide at 120 - 125℃; for 6h;	154.6 g

3-(trimethoxysilyl)-1-propanethiol (4420-74-0) + triallyl isocyanurate (1025-15-6) → 1,3,5-tris [3-[[3-(trimethoxysilyl)propyl]thio]propyl]isocyanurate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 110℃; for 5h;	100%

triallyl isocyanurate (1025-15-6) → 1,3,5-tris(β,γ-dibromopropyl)-2,4,6-trioxo-1,3,5-triazine (52434-90-9)

Conditions	Yield
With tetraethylammonium bromide; bromine In dichloromethane at 60℃; for 20h; Reagent/catalyst; Solvent; Temperature;	99.5%

triallyl isocyanurate (1025-15-6) + 2-hydroxyethanethiol (60-24-2) → 1,3,5-tris[3-(2-hydroxyethylsulfanyl)propyl]-1,3,5-triazinane-2,4,6-trione

Conditions	Yield
With bis(1-methyl-1-phenylethyl)peroxide at 105℃; for 8h; Temperature; Reagent/catalyst; Inert atmosphere; Schlenk technique;	97%

1,4-Butanedithiol (1191-08-8) + triallyl isocyanurate (1025-15-6) → 1,3,5-tris[3-(4-mercaptobutylsulfanyl)propyl]isocyanurate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70℃; for 4h;	96%

Triethoxysilane (998-30-1) + triallyl isocyanurate (1025-15-6) → C18H31N3O6Si

Conditions	Yield
With platinum-containing olefin organic polymer catalyst at 25℃; for 24h;	95%

triallyl isocyanurate (1025-15-6) + silver perchlorate → [Ag(triallyl isocyanurate)(ClO4)]n

Conditions	Yield
In acetone	90.4%

triallyl isocyanurate (1025-15-6) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C48H42N3O9P3

Conditions	Yield
With dibenzoyl peroxide In 1,4-dioxane at 110℃; under 7500.75 Torr; for 12h; Pressure; Temperature; Solvent; Autoclave; Large scale;	88.5%
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 10h; Solvent; Temperature;

3-(trimethoxysilyl)-1-propanethiol (4420-74-0) + triallyl isocyanurate (1025-15-6) → C18H31N3O6SSi

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Cooling with ice;	76%

2-mercaptoethyl-3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate (240494-25-1) + triallyl isocyanurate (1025-15-6) → C33H57N3O15S3 (1228999-35-6)

Conditions	Yield
With 2,2-bis(hydroxymethyl)propionic acid In methanol at 20℃; Inert atmosphere; UV-irradiation;	71%

triallyl isocyanurate (1025-15-6) + thioacetic acid (507-09-5) → 1,3,5-tris(3-acetylmercaptopropyl)-1,3,5-triazine-2,4,6-trione (76486-41-4)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In tetrahydrofuran at 65℃; for 16.5h; Inert atmosphere;	67%
With 2,2'-azobis(isobutyronitrile) In methanol; water

triallyl isocyanurate (1025-15-6) + copper(I) bromide (7787-70-4) → [(triallyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione)2hexabromohexacopper(I)](n)

Conditions	Yield
In ethanol heated for 3 d at 80-90°C in a sealed tube;	50%

triallyl isocyanurate (1025-15-6) + copper(I) bromide (7787-70-4) → [(triallyl-1,3,5-triazine-2,4,6-(1H,3H,5H)-trione)2tetrabromotetracopper(I)](n)

Conditions	Yield
In methanol heated for 3 d at 50-60°C in a sealed tube;	40%

triallyl isocyanurate (1025-15-6) + silver nitrate → [Ag(triallyl isocyanurate)(NO3)]n

Conditions	Yield
In water	34%

triallyl isocyanurate (1025-15-6) → allylisocyanate (1476-23-9)

Conditions	Yield
With hydrogenchloride; toluene dann Erhitzen bis auf 220grad oder beim Behandeln mit Chlorwasserstoff bei 130grad;

Upstream product

• 590-28-3 potassium cyanate 
• 107-05-1 3-chloroprop-1-ene 
• 75-05-8 acetonitrile 
• 108-80-5 cyanuric acid 
• 101-37-1 triallyl cyanurate 
• 16715-84-7 2,4,6-tris(methallyloxy)-1,3,5-triazine 
• 1476-23-9 allylisocyanate 
• 542-75-6 E/Z-1,3-Dichloropropene 
• 917-61-3 sodium isocyanate 
• 106-95-6 allyl bromide 
• 108-80-5 isocyanuric acid 
• 4873-09-0 allyl tosylate 
• 107-18-6 allyl alcohol 
• 3047-33-4 sodium cyanurate 

Downstream Products

• 1476-23-9 allylisocyanate 
• 20395-16-8 1,3-diallyl-5-glycidyl isocyanurate 
• 52434-90-9 1,3,5-tris(β,γ-dibromopropyl)-2,4,6-trioxo-1,3,5-triazine 
• 26947-14-8 C₁₈H₃₅N₃O₉Si₂ 
• 26115-70-8 tris-[3-(trimethoxysilyl)propyl]isocyanurate 
• 76486-41-4 1,3,5-tris(3-acetylmercaptopropyl)-1,3,5-triazine-2,4,6-trione 
• 2451-62-9 teroxirone 
• 69731-45-9 1-allyl-3,5-diglycidyl isocyanurate 

Relevant academic research and scientific papers

Selective and Efficient Syntheses of Perhydro-1,3,5-triazine-2,4,6-triones and Carbodiimides from Isocyanates Using ZP(MeNCH2CH2)3N Catalysts

With concentrations as low as 0.0033 mol percent ZP(MeNCH2CH2)3N (Z = lone pair, 1) isocyanates are catalytically trimerized to perhydro-1,3,5-triazine-2,4,6-triones (isocyanurates) at room temperature.This reaction proceeds readily in the presence or absence of solvent, and the catalyst can be recycled at least six times without detectable degradation.Though not as potent a catalyst as 1, the molecule in which Z = NPh (3) also facilitates this reaction, and evidence is adduced that the catalytically active species is the adduct 3*ArNCO (6).In contrast, Ch=P(MeNCH2CH2)3N (Ch = O, 4; Ch = S, 5) selectively catalyze the transformation of isocyanates to carbodiimides and do so more efficiently than their acyclic analogues O=P(NMe2)3 and (MeO)2P(S)Ph, respectively.The crystal structure of 4 is reported for the first time, and details of the crystal structure of I reported earlier by us in preliminary form are presented.Both structures support the hypothesis that P-Nax transannulation plays a lead role in the catalytic activities of 1 and 3 - 5.

Organocatalytic, rapid and facile cyclotrimerization of isocyanates using tetrabutylammonium phthalimide-N-oxyl and tetraethylammonium 2-(carbamoyl)benzoate under solvent-free conditions

Tetrabutylammonium phthalimide-N-oxyl and tetraethylammonium 2-(carbamoyl)benzoate were found to be effective and easily accessible organocatalysts for selective cylotrimerization of aryl and alkyl isocyanates under mild reaction conditions. The reaction proceeds smoothly using very low catalyst loadings of these metal-free organocatalysts (0.025 and 0.25 mol%, respectively) under solvent-free conditions at room temperature within a very short reaction time.

Amine-linked N-heterocyclic carbenes: The importance of an pendant free-amine auxiliary in assisting the catalytic reaction

We have successfully expanded the library of amino-NHCs with varying substituents on the amine group, leading to insight about the instability of NHCs arising from the intermolecular interaction of the dangling amine side-arm. However, the pendant amine plays an important role with respect to the catalytic process, resuscitating the catalytic activity of unsaturated NHC's through a synergistic effect invoked by the secondary amine. This proof of concept allows us to expand the spectrum of catalysis to C-C, as well as C-B bond formation. Copyright

Preparation process of triallyl isocyanurate (by machine translation)

The preparation process is characterized in that allyl alcohol is used as a raw material, allyl alcohol and p-toluenesulfonyl chloride are prepared into allyl tosylate through an acid binding agent; and the prepared allyl tosylate is reacted with sodium cyanate, a phase transfer catalyst and a polar solvent to obtain triallyl isocyanurate. To the preparation method, allyl alcohol is adopted as the raw material, atmospheric pollution is reduced, the reaction rate is higher, the yield of triallyl isocyanurate is improved, the environment is protected, and the energy-saving and consumption-reducing effect is remarkable. (by machine translation)

Highly efficient cyclotrimerization of isocyanates using N-heterocyclic olefins under bulk conditions

With a catalyst loading as low as 0.005%, high to excellent yields of isocyanurates could be achieved from N-heterocyclic olefin mediated organocatalytic cyclotrimerization of a wide range of isocyanates under bulk conditions. Experimental details coupled with structural characterization of the key intermediates led to comprehensive mechanistic studies of cyclotrimerization.

Aluminium-catalysed isocyanate trimerization, enhanced by exploiting a dynamic coordination sphere

Main-group metals are inherently labile, hindering their use in catalysis. We exploit this lability in the synthesis of isocyanurates. For the first time we report a highly active catalyst that trimerizes alkyl, allyl and aryl isocyanates, and di-isocyanates, with low catalyst loadings under mild conditions, using a hemi-labile aluminium-pyridyl-bis(iminophenolate) complex.

Method for synthesizing highly pure cross-linking agent triallyl isocyanurate

The invention discloses a method for synthesizing highly pure cross-linking agent triallyl isocyanurate. The highly pure triallyl isocyanurate is synthesized from bromopropene, cyanuric acid, a phasetransfer catalyst and a composite catalyst in a polar organic solvent, produced tail gas hydrogen bromide is fully absorbed by circulating water of asecondary graphite parallel flow falling film absorption tower, and is used into prepare certain-concentration hydrobromic acid for sale; the above synthesis reaction is carried out in the organic medium instead of a strong alkaline aqueous solution,so generation of a large amount of wastewater containing organic matters and salts is avoided, and treatment and processing of high-concentration wastewater and waste residues are avoided; and the finally obtained reaction solution is desolvated to obtain the highly pure TAIC with a content of 99.0% or above.

Production of [...]

A method for producing alkenyl isocyanurate by reacting cyanuric acid or isocyanuric acid with an unsaturated alcohol while in the presence of a palladium-loaded-activated-carbon catalyst. (Unsaturated alcohol example) R1-5: H, C1-20 alkyl, C6-20 aryl, C6-20 heterocyclic hydrocarbon; n: 1-4 (2-propen-1-ol, 3-buten-1-ol, 4-penten-1-ol, 5-hexen-1-ol, 2-buten-1-ol, 3-penten-2-ol, 2-methyl-2-propen-1-ol, and the like). (Example of palladium-loaded-activated-carbon catalyst) A zero-valent metal palladium, a bivalent palladium compound, or a catalyst obtained by loading activated carbon with these mixtures.

Photosensitive resin composition for color filter and uses thereof

The present invention relates to a photosensitive resin composition for a color filter and uses thereof. The photosensitive resin composition includes an alkali-soluble resin (A), a compound (B) containing an ethylenically unsaturated group, a photoinitiator (C), a pigment (D) and an organic solvent (E). The photosensitive resin composition according to the present invention can improve linearity of pattern with high finesse and developing-resistance of the color filter.

MANUFACTURING METHOD OF ISOCYANURATE COMPOUND

PROBLEM TO BE SOLVED: To provide a method using a raw material with low toxicity, capable of easily controlling a reaction even with mass production equipment, and manufacturing an isocyanurate compound selectively at high yield while maintaining safety. SOLUTION: By heating a triisocyanurate compound, a carboxylic acid compound, a metallic salt and a solvent with oxygen concentration of a reaction tank inner gas phase of less than 0.4 vol.%, a raw material with low toxicity is used and a reaction even with mass production equipment can be easily controlled and an isocyanurate compound can be manufactured selectively at high yield while maintaining safety. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT