| Product Name: | Cyanuric chloride | | Synonyms: | 1,3,5-trichloro-2,4,6-triazine;Cyanuric chL;syn-trichlotriazin(czech);Trichloro-s-triazine;Trichloro-1,3,5-triazine;,3,5-Trichloro-2,4,6-triazine;1,3,5-Triazine, 2,4,6-trichloro-;1,3,5-Triazine,2,4,6-trichloro- | | CAS: | 108-77-0 | | MF: | C3Cl3N3 | | MW: | 184.41 | | EINECS: | 203-614-9 | | Product Categories: | Intermediates of Dyes and Pigments;Chlorination;Organics;Halogenation;Synthetic Organic Chemistry;Dyestuff Intermediates;Building Blocks;Chemical Synthesis;C-X Bond Formation (Halogen);Heterocyclic Building Blocks;Synthetic Reagents;Triazines;Halogenated Heterocycles;fine chemicals;108-77-0;K00001 | | Mol File: | 108-77-0.mol |  |
| | Cyanuric chloride Chemical Properties |
| Melting point | 145-147 °C(lit.) | | Boiling point | 190 °C(lit.) | | density | 1.92 | | vapor density | 6.36 (vs air) | | vapor pressure | 0.8 mm Hg ( 62.2 °C) | | Fp | 190°C | | storage temp. | Store below +30°C. | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | -3.26±0.10(Predicted) | | form | Solidified Mass or Fragments | | color | White | | Odor | pungent odor | | Water Solubility | reacts | | Sensitive | Moisture Sensitive | | Merck | 14,2699 | | BRN | 124246 | | Stability: | Stable. Incompatible with strong oxidizing agents, water. | | LogP | 1.73-2.14 at 25℃ | | CAS DataBase Reference | 108-77-0(CAS DataBase Reference) | | NIST Chemistry Reference | Cyanuric chloride(108-77-0) | | EPA Substance Registry System | Cyanuric chloride (108-77-0) |
| | Cyanuric chloride Usage And Synthesis |
| Outline | Cyanuric chloride, white crystals with a strong irritant chlorine odor , is corrosive to the skin, having eye irritation and tearing property. Melting point 145 ℃, boiling point 190 ℃, UVλmax241nm (ethanol).it is Soluble in ethanol, ethyl ether, chloroform, acetic acid and acrylonitrile, insoluble in cold water. cooling of reaction of Cyanuric chloride and water is slow, when it is heated it is rapidly hydrolyzed to cyanuric acid (C3H3O3N3) and hydrochloric acid, the product are relatively soluble in water, so you can use the extraction method of separating. It Reacts With concentrated nitric acid and concentrated sulfuric acid at room temperature to be partial conversion of cyanuric acid, and it reacts with the sodium alkoxide to generate cyanuric acid triester, and it can also react with ammonia, amines, phenols and so on.
In recent years, there is rapid growth in consumption of cyanuric chloride in China, from 1998 to 2004 the average annual growth rate of Apparent consumption was about 32.2% ,in 2005, cyanuric chloride demand reached 50,000 tons, according to forecasts, from 2007 to 2012 cyanuric chloride will continue rapid growth in average rate of 6.0% , the market is very promising. Since cyanuric chloride subsequent products are enormous , the market demand is large, national research institutions and related businesses have continued to develop its downstream products, and open cyanuric chloride applications. Therefore, the new product by the cyanuric chloride derivatives are emerging, the market demand will be further expanded.
Related cyanuric chloride chemical reactions involving:
After 2-amino-4-nitrophenol diazotization, and H acid coupling, and chromium, cobalt complex post-processing,it is first condensed with cyanuric chloride ,then after condensation with ammonia to get Reactive Black K-BR. It is Mainly used for cotton, polyester/cotton printing.
With cyanuric chloride as raw materials, in trichlorethylene solution at 20~30 ℃, with the amine reaction , 2,4-dichloro-6-ethyl-1,3,5-triazine is produced, and then it reacts with ammonia to produce 2-amino-4-chloro-6-ethylamino triazine, and then it reacts with 2-chloro-2-methyl propionitrile , which can generate selective herbicides cyanazine for control annual or perennial narrow leaves or broadleaf weeds in corn field.
| | Chemical Properties | Crystals Having a pungent odor. Soluble in chloroform, carbon tetrachloride, ethanol, hot ether, acetone, dioxane, slightly soluble in water.
| | Uses | cyanuric chloride is an important fine chemical product, with a wide range of uses, it is the intermediate in pesticide industry, and the manufacture of reactive dyes raw material, it can used as all kinds of organic industrial production additives, such as fluorescent brighteners , textiles shrink-proof agents, surface active agents, it is one of the materials used in the manufacture of defense explosives and rubber accelerator and it is also the material for the synthesis of drugs by the pesticide and pharmaceutical industry.
The above information is edited by the chemicalbook of Tian Ye.
| | production method | Cyanuric chloride production process usually consists of two steps : chloride cyanogen polymerization and chloride cyanogen preparation . There are many ways to generate chloride cyanogen, such as the synthesis of methyl thiocyanate and chlorine, hydrocyanic acid is dissolved in chloroform and chlorine gas is put in to synthesize , hydrocyanic acid method, sodium cyanide, urea, hydrocyanic acid direct method of chlorine and cyanuric chloride and the like, the current production of industrial cyanuric chloride generally uses sodium cyanide and hydrocyanic acid as raw materials in two ways. 1. Sodium cyanide method : using sodium cyanide as raw materials after the reaction of chlorine and cyanuric chloride, it is polymerized to form cyanuric chloride, it is quenched,then after crystallization ,the product is obtained. Material consumption fixed: sodium cyanide 1073kg/t, chlorine 1700kg/t. 2. The method of hydrocyanic acid :with hydrocyanic acid as raw materials ,chloride cyanogen is produced by the reaction of chlorine, and then use polymerization to generate cyanuric chloride, quench, crystallize , the product is obtained. Material consumption fixed: hydrocyanic acid 500kg/t, chlorine 1200kg/t.
| | Category | corrosive substances
| | Toxicity grading | Middle toxic
| | Acute toxicity | Oral-rat LD50: 485 mg/kg; Oral-Mouse LD50: 350 mg/kg
| | Irritation data | skin-rabbit 500 mg/24 hours of moderate; Eyes-rabbit 0.05 mg/24 hours of severe
| | Flammability and hazard characteristics | When it contacts with water ,it emits toxic hydrogen chloride gas;when it is thermal it decomposes toxic hydrogen chloride gas
| | Storage Characteristics | Ventilated, low-temperature ,dry storeroom.it is stored separately from oxidants,and alkali.
| | Extinguishing agent | carbon dioxide, dry powder,sandy soil
| | Chemical Properties | White Powder | | Uses | Cyanurchloride is an intermediate to manufacture of agrochemicals (triazine herbicides), dyestuffs, optical brighteners, tanning agents, reactive dyes, UV-absorbing agent, softening agents and pharmaceuticals, as well as block-builders for plastics. Product Data Sheet | | Uses | Cyanurchloride is an intermediate to manufacture of agrochemicals, dyestuffs, optical brighteners, tanning agents, softening agents and pharmaceuticals, as well as block-builders for plastics. | | Uses | Reagent for the conversion of alcohols to chlorides and for the immobilization of microorganisms and enzymes.1 | | Uses | Cyanuric Chloride is extensively used in the preparation of the triazine-class pesticides and herbicides. Cyanuric chloride is also used as a precursor to dyes and crosslinking agents due to the react
ive chlorine atoms towards nucleophilic substitution reactions. Cyanuric chloride derivatives possess a large spectrum of activities as antibacterial and anticancer agents. | | Uses | Intermediate in the synthesis of active dyes, agricultural products, and drug substances. Reagent in organic synthesis. Coupling agent for nucleic acids and proteins; cyanuric chloride-activated paper is used in capillary and electroblotting applications, dot tests, and hybridization protocols. | | Definition | ChEBI: A chloro-1,3,5-triazine in which the triazine ring is substituted on each carbon by chlorine. Its main use is in the preparation of the triazine-class pesticides. | | Production Methods | Cyanuric chloride is obtained by the trimerization of cyanogen
chloride in organic solvents, in the presence of acidic
catalysts, and carried out in a gaseous phase at 200–500C.
Cyanuric chloride is used as a chemical intermediate. It is the
precursor to the herbicide atrazine. | | General Description | A colorless crystalline solid with a pungent odor. Melting point 146°C. Density 1.32 g / cm3. Very slightly soluble in water. Toxic by ingestion and inhalation of vapors. Irritates skin and eyes. Used to make dyes. | | Air & Water Reactions | Reacts exothermically with water, especially if catalyzed or heated, to generate fumes of hydrochloric acid. Very slightly soluble in water. | | Reactivity Profile | Cyanuric chloride reacts rapidly and exothermically with water to generate hydrogen chloride. A mixture with water in an industrial reactor with refrigeration turned off developed pressure that blew gaskets and filled the building with flammable vapors. An explosion occurred when the vapors were ignited [MCA Case History 1869(1972)]. Runaway reactions have occurred with acetone/water; methanol/water, ethoxyethanol/water, allyl alcohol/sodium hydroxide/water, 2-butanone/sodium hydroxide/water, and methanol/sodium bicarbonate [Loss Prev. Bull., 1979, (25), 21]. Reacts with methanol to give gaseous methyl chloride. Reacts rapidly with bicarbonates to generate gaseous carbon dioxide. Reacts vigorously with dimethyl formamide (DMF) to form carbon dioxide after a deceptive induction period [BCISC Quart. Safety Summ., 1960, 35, 24]. Can react with reducing agents to generate heat and products that may be gaseous (causing pressurization of closed containers). The products may themselves be capable of further reactions (such as combustion in the air). | | Health Hazard | TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. | | Fire Hazard | Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Vapors may accumulate in confined areas (basement, tanks, hopper/tank cars etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. | | Flammability and Explosibility | Nonflammable | | Safety Profile | Poison by ingestion,
inhalation, and intravenous routes.
Questionable carcinogen with experimental
tumorigenic data. Experimental
reproductive effects. A corrosive. A skin and
severe eye irritant. An allergen. Has been
reported as causing irritation of mucous
membranes and heart rhythm disturbances
in humans. Violent reaction with water -
(above 30°C), acetone + water, methanol,
methanol + sodium hydrogen carbonate, 2-
ethoxyethanol, dimethyl formamide, 3-
butanone + sodium hydroxide + water, allyl
alcohol + sodium hydroxide + water (at
28℃). When heated to decomposition it
emits toxic fumes of Cland NOx. See also
CHLORIDES. | | Purification Methods | TCT crystallises from CCl4 or pet ether (b 90-100o) and is dried under vacuum. It has also been recrystallised twice from anhydrous *benzene immediately before use [Abuchowski et al. J Biol Chem 252 3582 1977]. [Beilstein 26 III/IV 66.] |
| | Cyanuric chloride Preparation Products And Raw materials |
| Raw materials | Urea-->Chlorine-->Sodium cyanide-->HYDROGEN CYANIDE-->Methyl thiocyanate | | Preparation Products | Simazine-->C.I. Reactive yellow 1-->Reactive Yellow 179-->2-[[4-[[4-[bis(2-hydroxyethyl)amino]-6-chloro-1,3,5-triazin-2-yl]amino]phenyl]azo]-p-cresol-->Reactive Light Yellow M-5G-->ANILAZINE-->fluorescent whitening agent RA-->CIBACRON BRILLIANT YELLOW 3G-P-->Reactive Violet 2-->Direct Blending Brilliant Red D-5BL-->Reactive Yellow 18-->ReactivebrilliantredKE-7B-->C.I. Reactive Blue 1-->REACTIVE ORANGE 14-->Reactive Yellow 84-->tetrasodium 3,3'-[(1,6-dihydro-6-oxo-1,3,5-triazine-2,4-diyl)bis[imino(5-methoxy-2-methyl-4,1-phenylene)azo]]bis(naphthalene-1,5-disulphonate)-->Direct Blend Rubine D-BLL-->Reactive Brilliant Orange K-R-->Reactive Yellow KE-RN-->Reactive Disperse Scarlet G-->Fluorescent Brightener 220-->REACTIVE RED 120-->Cyanuric fluoride-->Reactive Red M-3BE-->REACTIVE RED 195-->Bladex-->Reactive Blue 81-->trisodium 2-[[6-[(4,6-dichloro-1,3,5-triazin-2-yl)methylamino]-1-hydroxy-3-sulphonato-2-naphthyl]azo]naphthalene-1,5-disulphonate-->SSH-108-->hexasodium 4-amino-3,6-bis[[5-[[4-chloro-6-[(3-sulphonatophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphonatophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonate-->Reactive Red Violet X-2R-->Neutral Brilliant Yellow S-5GL-->Altretamine-->trisodium 2-[[6-[(4-amino-6-chloro-1,3,5-triazin-2-yl)methylamino]-1-hydroxy-3-sulphonato-2-naphthyl]azo]naphthalene-1,5-disulphonate |
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