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1. Product Information

Chemical formula: C6H15O3P

Molecular weight: 166.16

CAS login number: 122-52-1

EINECS login number: 204-552-5

2. Physical information of triethyl phosphite

Appearance: colorless transparent liquid with special smell

Boiling point (℃): 156.6

Relative density (water = 1): 0.963 (20/4 ℃)

Saturated vapor pressure (kPa): 1.60 / 49 ℃

Flash point (℃): 54

Refractive index: 1.413

Vapor pressure: 3.19mmHg at 25 ° C

Solubility: Insoluble in water, soluble in most organic solvents such as ethanol, ether, benzene, and acetone.

3. Product Technology

1. Using anhydrous ethanol, phosphorus trichloride and liquid ammonia as raw materials to carry out esterification reaction in xylene solvent to generate triethyl phosphite, the crude ester is washed with water to remove ammonium chloride and diethyl phosphite, and distilled off After the solvent, it is rectified to obtain the finished product. Raw material consumption quota: phosphorus trichloride (95%) 950kg / t, absolute ethanol 930kg / t, liquid ammonia 340kg / t.

2. In a 3-liter three-necked flask equipped with a closed stirrer, a high-efficiency reflux condenser, and a 500-mL dropping funnel, put 138 g (175 mL, 3 mol) of absolute ethanol and 1 liter of dry petroleum ether (boiling point 40- At 60 ° C) there was 447 g (477 ml, 3 mol) of freshly distilled solution of diethylaniline. In the dropping funnel, put 400 ml of dry petroleum ether and 137.5 g (87.5 ml, 1 mol) of freshly distilled phosphorus trichloride solution. The flask was cooled in a cold water bath. Under vigorous stirring, add phosphorus trichloride i liquid, dropwise at a rate to gently reflux the mixture. It takes about 30 minutes to finish the drip. After the addition, heating and stirring were continued to reflux gently for 1 hour. The suspension containing a large amount of precipitated diethylaniline hydrochloride was cooled, and the dried amine salt filter cake was suction filtered on a water pump with a glass core funnel, and washed with 5 parts of 100 ml dry petroleum ether (boiling point 40-60 ° C). The filtrate and washing liquid were combined and distilled and concentrated on a water bath with a 75 cm long pine needle fractionating column. The residue was transferred to a pear-shaped flask and distilled with a 75 cm long pine needle-shaped fractionation column under reduced pressure by a water pump. After distilling out a small amount of pre-fraction, the product is collected at 57-58 ° C / 16mm (51-52 ° C / 13mm, 43-44 ° C / 10mm, the yield of colorless product is 138g (83%)

Wooden method can also use dimethylaniline, the generated hydrochloride is easy to filter out, and does not absorb moisture.

Four, use:

1. This product is used as a plastic stabilizer and plasticizer; also used as an intermediate for medicines and pesticides. It is used to produce analgesics phenothiazine, pesticides such as moxibustion, etc .; also used as plasticizers, stabilizers, lubricants and grease additives.

2. Preparation of linolein (Arbuzow reaction). Deoxidizer and desulfurizer. Hydroperoxide, peroxydiarylformyl, epoxide, isocyanate deoxygenation, 1,2-dione deoxygenation to produce alkyne. Reduction of nitrogen-containing functional groups. Desulfurization of episulfide, mercaptan and disulfide. Reduction of α-keto acid to α-hydroxy acid. With α-halogenated aldehyde, ketone to form dialkyl ethylene phosphate (Perkow reaction).

3. Triethyl phosphite has a wide range of uses in organic synthesis and is often used as a reducing agent and nucleophile. The reactions that it directly participates in are named as different names due to their importance.

Triethyl phosphite is used as a reducing agent. In the reaction, the phosphorus atom itself is oxidized from +3 to +5, and it is accompanied by the function of taking oxygen or sulfur atoms from another reactant to generate the corresponding triethyl phosphate. ester. For example, triethyl phosphite can reduce peroxy compounds to alcohols, and under controlled conditions can selectively reduce one of them in the presence of two peroxy groups. 1,3-Dimercaptoketone can undergo coupling reaction in the presence of triethyl phosphite. The corresponding olefin can be obtained by refluxing triethyl phosphite together with aldehyde and 1,3-dimercaptothione. It is reported in the literature that triethyl phosphite can also undergo oxygen exchange reactions with other phosphate esters.

One of the name reactions led by triethyl phosphite is the Arbuzov reaction. Triethyl phosphite and halogenated hydrocarbons first undergo nucleophilic substitution reaction, and at the same time, the halogen ion causes the ethoxy group to cleave to generate a hydrocarbyl substituted diethyl phosphonate derivative. When there is an electron-withdrawing group in the β-position of the halogen atom in the halogenated hydrocarbon, the product forms phosphine ylide under the action of a strong base, and then undergoes a "one-pot" reaction with aldehyde to obtain the product of Horner-Emmons reaction. This reaction plays an important role in the synthesis of complex natural products.

Another name reaction led by triethyl phosphite is the Cadogan reaction, which is an important method for the synthesis of polycyclic nitrogen-containing heterocyclic compounds. The aryl nitro functional group is co-heated with triethyl phosphite to reduce the nitro group to a nitrogen atom. Nitrogen then attacks other olefinic bonds or aromatic rings in the molecule to form polycyclic nitrogen-containing heterocyclic compounds. In the Cadogan reaction, triethyl phosphite generally serves as both a reactant and a solvent. For example: o-vinyl substituted nitrobenzene and triethyl phosphite are co-heated to generate indole derivatives. Carboline derivatives are generated when o-aryl substituted nitrobenzene and triethyl phosphite are co-heated.

V. Export essential documents for triethyl phosphite

Cas number: 122-52-1, UN: 3082

Customs Code HS: 29209012

Tax refund: The current tax refund for triethyl phosphite is 9%.

Raw materials: Absolute ethanol, phosphorus trichloride and liquid chlorine are used as raw materials.

It belongs to several types of dangerous goods: At present, triethyl phosphite belongs to 3 types of dangerous goods.

Packing: Net weight 200KG / galvanized iron barrel (16 tons for a small cabinet), 1000KG / IB barrel (18 tons for a small cabinet)