Alkyl phosphonate preparing method

A technology of hydrocarbyl phosphonate and hydrocarbyl phosphate, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve the problem of limited reaction substrates, large steric hindrance, carbon-halogen bond Low polarizability and other issues, achieve high reaction efficiency and conversion rate, and expand the effect of selection range

Active Publication Date: 2017-09-15
ASYMCHEM LIFE SCI TIANJIN
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Problems solved by technology

[0007] The main purpose of the present invention is to provide a kind of preparation method of hydrocarbyl phosphonate, when utilizing Arbuzov reaction to prep...

Method used

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preparation example Construction

[0024] In order to solve this problem, the present invention provides a kind of preparation method of hydrocarbyl phosphonate, it comprises the following steps: compound A and compound B are carried out Arbuzov reaction in continuous reaction equipment, and in reaction process, react The product is continuously discharged from the continuous reaction equipment to obtain hydrocarbyl phosphonate; wherein compound A is shown in structure I, and compound B is shown in structure II:

[0025]

[0026] Wherein, in structure I, X is a halogen atom, R 1 Is an alkyl or substituted alkyl, wherein the substituent of the substituted alkyl is aryl, ester, epoxy, alkenyl or acyl; in structure II, R is methyl, ethyl or phenyl; and during the reaction The reaction temperature is T1, the boiling point of compound A and compound B with the lower boiling point under standard atmospheric pressure is T2, T1 is 10-40°C higher than T2, and the reaction pressure during the reaction is 0.5-2.0MPa. ...

Embodiment 1

[0041]

[0042] Heat the dry and clean 500mL coil to 170°C, take 1000g (0.7eq.8.16mol) of compound 1 (boiling point at standard atmospheric pressure 142-145°C) into the feeding bottle A, add 4000g of toluene to dilute, and take the phosphorous acid 1937g (1.0eq.11.66mol) of triethyl ester (boiling point at standard atmospheric pressure is 156.6°C) is placed in the feeding bottle B, and 3063g of toluene is added for dilution. solution): 16.7 g / min, pump B (triethyl phosphite in toluene): 16.7 g / min. The residence time is 15min, and the reaction pressure is 0.5-2.0Mpa. The discharge port is directly connected to the thin film evaporation device, and the control pressure is 4~10×10 2 Pa, temperature 105-115 DEG C, finally obtain product 2 (boiling point 129-131 DEG C, 800 Pa) 1701g, yield 93%.

[0043] 1 H NMR (400MHz, CDCl 3 ):δ4.14–4.21(m,4H),3.86–4.01(m,2H),3.00(d,2H),1.35(t,J=6.8Hz,3H),1.22(t,J=6.8Hz, 3H).

Embodiment 2

[0045]

[0046] Heat the dry and clean 500mL coil to 155°C, take 1000g of compound 1 (0.7eq.8.16mol, the boiling point at standard atmospheric pressure is 142-145°C) into the bottle A, add 4000g of toluene to dilute; take phosphorous acid 1937g (1.0eq.11.66mol) of triethyl ester was placed in the feeding bottle B, and 3063g of toluene was added to dilute it. After the temperature of the coil was stable, the feeding was started. Pump A (toluene solution of compound 1): 16.7g / min, pump B (toluene solution of triethyl phosphite): 16.7 g / min. The residence time is 15min, and the reaction pressure is 2Mpa. The discharge port is directly connected to the thin film evaporation device, and the control pressure is 4~10×10 2 Pa, the temperature is 140-145° C., and finally 1683 g of product 2 is obtained with a yield of 92%.

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Abstract

The invention provides an alkyl phosphonate preparing method. The method comprises: performing an Arbuzov reaction on compound A and compound B in a continuous reaction apparatus, and continuously discharging the product obtained from the reaction from the continuous reaction apparatus during the reaction procedure, to obtain alkyl phosphonate. The reaction temperature in the reaction procedure is T1; either of compound A and compound B having a lower boiling point has a boiling point at a standard atmosphere pressure to be T2; T1 is higher than T2 by 10-40 DEG C; and the reaction pressure in the reaction procedure is 0.5-2.0 MPa. The preparing method in the invention may use halohydrocarbon having large steric hindrance and lower polarizability of carbon-halogen bond as compound A, thereby effectively expanding a selection range of substrate, and correspondingly expanding the types of alkyl phosphonate prepared by using the Arbuzov reaction.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of hydrocarbyl phosphonate. Background technique [0002] The Arbuzov reaction, also known as the Arbuzov rearrangement reaction, is one of the most widely used reactions in organophosphorus chemistry. Organophosphorus compounds are an important class of chemical substances that exhibit many excellent properties and are widely used in agriculture (Heteroatom Chem.2000,11(4),261-266), medicine (Tetrahedron Lett.2006,47,7719-7721 .;Org.Lett.2006,8(19),4243-4246.;J.Am.Chem.Soc.1982,104,3107-3114), industry (J.Electro-analytical Chem.2001,507,157-169) etc. The construction of phosphorus-carbon bonds by Arbuzov reaction is an effective way to prepare compounds such as hydrocarbyl phosphonates, phosphinates and phosphine oxides. [0003] The Arbuzov reaction was first discovered by Michaelis in 1898, and later developed by Arbuzov (Org. Process Researc...

Claims

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Application Information

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IPC IPC(8): C07F9/40C07F9/655
CPCC07F9/4003C07F9/4006C07F9/4015C07F9/4056C07F9/65505
Inventor 洪浩詹姆斯·盖吉卢江平李超张恩选
Owner ASYMCHEM LIFE SCI TIANJIN
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