Atrazine

White crystalline solid. Melting point 173-175°C. Sinks in water. A selective herbicide used for season-long weed control in a variety of crops.

Preparation of cyanuric chloride cyanuric chloride is an important intermediate for the synthesis of benzotriazine herbicides. Its synthesis includes two steps of chlorination and polymerization, the reaction formula is as follows. HCN+Cl2→CNCl+HCl3CNCl[Catalyst]→(CNCl)3 The production process of cyanuric chloride of DuPont Company of the United States is as follows: chlorine gas and hydrocyanic acid are entered in the lower half of the reaction tower according to a certain ratio (excess chlorine), the bottom of the tower Introduce low-pressure steam, enter the low-temperature water at the top of the tower according to the regulations, chlorine gas and hydrocyanic acid generate cyanogen and hydrogen chloride in the tower, get cyanogen from the tower item, and continuously discharge dilute hydrochloric acid from the bottom of the tower, with a content of about 4%, and send it to the factory wastewater Station processing. The top cyanogen chloride and excess chlorine gas are dried by calcium chloride and molecular sieve (water content <10mg/L) and sent to the polymerization reactor. The reactor is a vertical fixed bed, and the catalyst may be activated carbon (structure, catalyst, reaction conditions are patents) The life span is generally 3 months, but it is changed once a month according to production regulations. The spent catalyst is sent to an incinerator for burning. It is said that it is very convenient to change the catalyst method. The cyanuric chloride obtained after the polymerization is sent to the next washing tower, washed with a solvent (may be a heavy aromatic hydrocarbon, which requires low volatility), and then stored in a storage tank for the synthesis of mesotriazine herbicides. After absorption, part of the exhaust gas is evacuated according to the analysis, and most of it is recycled to the previous step cyanogen cyanide reaction tower. The exhausted exhaust gas goes to the exhaust gas washing tower and is washed with lye and sodium hypochlorite. The chlorination reaction tower is a φ1m×20m high nickel steel reactor, the trimerization reactor is a φ2m×6m high nickel steel reactor, and the tail gas treatment tower is a φ2m×20m packed tower. The synthesis of atrazine uses water-chlorobenzene as the solvent. After mixing cyanuric chloride with the solvent, the temperature is reduced to 15°C, and the metered ethylamine is added dropwise. The temperature rises by itself. Add 50% of the amount of liquid alkali. Reaction at ～20℃ for 30min; then add the metered isopropylamine and the rest of the liquid alkali and react at 30～40℃ for 2h. Chlorobenzene and water are distilled off by water vapor distillation, and chlorobenzene is recovered by separation and drying. The materials in the kettle are cooled, centrifugally separated, washed with water, and dried, which is the raw material. CA110: 212860 reported that the production method of atrazine is as follows: in the presence of surfactants, cyanuric chloride (C3N3Cl3), ethylamine, isopropylamine and sodium hydroxide in hydrolysate or in an aqueous solution containing alkali metal chloride The specific operation is: a mixture of 30g of cyanuric chloride and 250mL of water is reacted with 0.1mL Slovanik T 610 (ethylene oxide/propylene oxide copolymer) at 5°C, and then with 50mL of 20.0% isopropylamine for 30min After reaction with 55mL 10% aqueous sodium hydroxide solution, the reaction temperature is 5 ~ 10 ℃, 50min reaction with 21.5mL 39% ethylamine aqueous solution, after more than 40 minutes with 50mL 10.1% aqueous sodium hydroxide solution. After 50min, the product was filtered, washed and dried to obtain 33.1g of product. Atrazine 97.1%, simazine 1.6%, and putazone 0.9%.

Selective herbicide.Atrazine is used as a selective herbicide to control broadleaf and grassy weeds for agriculture and other land not used for crops. In agriculture, atrazine is used on corn, sugarcane, and pineapple and for orchards, sod, tree plantations, and rangeland. Atrazine is moderately persistent in the environment because of its low solubility. It can be detected in the water table and in the upper layers of the soil profile in many areas (Huang and Frink, 1989). The Environmental Protection Agency (EPA) reported that atrazine was one of the two most commonly used agricultural herbicides in 2007 (EPA, 2011). It is an active ingredient in many brands, including Actinite PK, Atranex, Atrasine, Atrataf, Atrazin, Chromozin, Cyazin, Primatol A, Primase, AAtre, Griffex, and Weedex.

Molecular Weight:215.68
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:215.0937732
Monoisotopic Mass:215.0937732
Topological Polar Surface Area:62.7
Heavy Atom Count:14
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes