Method of producing n,n-dimethylacetamide

FIELD: chemistry.

SUBSTANCE: invention relates to a novel method for synthesis of N,N-dimethylacetamide, which is widely used as a solvent in different fields, involving reaction of ethyl acetate (EA) and N,N-dimethylamine (DMA) in the presence of polyethylene polyamines (PEPA), having formula NH2[(CH2CH2)NH]n-1CH2CH2NH2, where n = 2-4, as a catalyst, where separate compounds of this group or their mixtures can be used.

EFFECT: high output of the end product (dimethylacetamide) of high quality (more than 99,9% content of basic substance) due to a simpler step for separating the catalyst from the reaction products.

3 cl, 16 ex, 1 tbl

 

The invention relates to the field of synthesis of aprotic solvents that are widely used in various fields of technology, and, in particular, in the production of high-strength polyamide fibers, intended for the reinforcement of concrete products in the construction and bridge building, as well as automobile and aircraft construction.

It is now known [Kirk-Othmer encyclopedia, 3rd ed., v.1, N.Y., 1978, p.167-71], at least about ten different ways to obtain N,N-dimethylacetamide (hereinafter referred to as DMAA), but industrial application have found only two: getting by condensation of acetic acid with N,N-dimethylamine (hereinafter - DMA) and the conduct of aminolysis lower acetic acid esters (methyl acetate and ethyl acetate) using N,N-dimethylamine.

To DMAA used in the production of polyamide fibers, meet strict requirements for quality, the main of which are the reduction of water content and little or no acidity. Thus presents two industrial methods, the preferred method of obtaining DMAA by the interaction of esters of acetic acid with DMA. Getting DMAA by aminolysis lower esters of acetic acid N,N-dimethylamine is carried out, usually in the presence of basic catalysts

A method of obtaining DMAA [U.S. Patent 3342862, NCI 260-561, op. 19.09.1967] by the interaction of acetate on the over - MA) with DMA at a temperature of 6÷30°C in excess gaseous DMA at atmospheric pressure. As the catalyst used hydroxycobalamin compounds (methanol, water). Conversion of MA when carrying out this method is 98%. However, in addition to time consuming process, a significant drawback of this method is the occurrence of side processes, in particular hydrolysis produced DMAA in the presence of water, which greatly complicates the process of selection of the target product and reduces its output.

To intensify the process of aminolysis and increase the rate of reaction the methods of obtaining DMAA from MA and DMA in the presence of strongly alkaline catalysts - alcoholate, amides or hydroxides of alkali metals [U.S. Patent 3538159, NCI 260-561, op].

The known method [WO2006061153, MP CL. SS 231/02, op. 15.06.2006] obtain this product by the continuous interaction of the acetate with dimethylamine in the presence of is 0.0002-0.09 mol of alkaline catalyst per mole of acetate, at a temperature of from 90 to 140°C and a pressure of from 10 to 30 ATM, and the conversion of MA is 81-96%.

In addition to strongly alkaline agents as catalysts in the process of obtaining DMAA from MA and DMA know the use of cobalt salts of carboxylic acids, in particular of cobalt acetate [U.S. Patent 4258200, NCI 231-00, op. 24.03.1981].

It is important to note that all representation is built above patents as source material used solely MA, industrial production which, due to the limitations of its application, does not exist. Therefore, the use of MA for the synthesis of DMAA is appropriate only in those companies where there is the production of MA for this purpose, or it is obtained in other processes as a by-product, such as, for example, by BASF for the production of polytetrahydrofuran [EP 1828102, MP CL. SS 231/02, op. 05.09.2007].

Therefore, great interest is the method of obtaining DMAA from DMA and available and relatively cheap ethyl acetate (EA), which is produced in industry in large quantities.

Known [Prototype Application form China 1807401, op. 26.07.2006] only one such way to obtain in which DMAA get from EA and DMA in the presence of catalysts based trioxide molybdenum and tungsten or metavanadate sodium at a temperature of 80-190°C and a pressure of 8-25 kgf/cm2.

The molar ratio of EA:DMA is 1:0,8÷2,0. These conditions provide a 92%conversion of the EA and the purity of the target product of 99.5%.

The disadvantage of this invention is that the proposed catalysts are solid crystalline substances in the synthesis process because of the need for intensive mixing crushed until finely dispersed state. This greatly complicates the Department produced DMAA from the catalyst and SN is pressed, the yield of the target product at a relatively high conversion EA. The difficulty selection DMAA from the reaction mixture leads to the loss of not only DMAA, but expensive catalyst. In addition, fine catalyst tends to rapid decontamination by-products of synthesis, which significantly reduces its service life.

Before the developers of the present invention had the task of developing a new method of obtaining DMAA-based EA and DMA using available and inexpensive catalyst that helps minimize loss DMAA and get a high quality product with high yield.

The essence of the invention is that a method of obtaining DMAA-based EA and DMA, and the interaction is carried out at a temperature of 80-120°C, using as catalyst polyethylenepolyamines (PEP) formula

NH2[(CH2CH2)NH]n-1CH2CH2NH2where n=2÷4.

The catalyst may be one of the compounds of the formula

NH2[(CH2CH2)NH]n-1CH2CH2NH2where n=2, 3, or 4, or their mixture, and the molar ratio of downloadable components EA:DMA:PEPA is 1:(2÷3):(0,03÷0,1).

Used as catalyst polyethylenepolyamine (AEDs) are characterized by the formula NH2[(CH2CH2)NH]n-1CH2CH2NH2,where n=2÷4, and can be used cicindelinae join this group and mixtures thereof. Such compounds are, for example:

Diethylenetriamine (DETA): NH2(CH2CH2)NH(CH2CH2)NH2;

Triethylenetetramine(THETA): NH2(CH2CH2)NH(CH2CH2)NH(CH2CH2)NH2;

Tetraethylenepentamine (TAP): NH2[(CH2CH2)NH]3(CH2CH2)NH2.

One of the main advantages of the developed method for DMAA is the use of available and relatively inexpensive source EA and catalysts of probes produced on an industrial scale, which allow for a moderate temperature of 60-120°C and a pressure of 1-10 kg/cm2to achieve the conversion of EA more than 90% and get DMAA high quality with the content of the basic substance is not less than 99.9% high yield - up to 85-90%.

The use of probes as catalysts for receiving DMAA is due, firstly, to their high basicity due to the presence of primary and secondary amino groups. However, unlike other strong bases, such as alcoholate of alkali metals, hydroxides of alkali and alkaline earth metals used in the process of aminolysis, these compounds are more selective with respect to DMAA and not catalyze the processes of hydrolysis and decomposition of DMAA. This has a positive effect on quality and yield of the target product. Secondly, the two probes which are high-boiling liquids with a boiling temperature of 200-300°C, well soluble in the source and end products, making it easy to homogenize the reaction mass, and at the end of the process is enough to drive away DMAA, having a boiling point of 165°C. from the reaction mixture, minimizing loss of the target product and catalyst. In the literary and experimental studies of the variety of probes were selected only those polyethylenepolyamine that met the following requirements:

- produced on an industrial scale;

- have a relatively low cost;

for a better separation of the reaction mixture boiling temperature should be not lower than 200°C.

PEPA, meets in full all these requirements, you are DEATH metal, THETA and TAP. These catalysts at the end of life (loss of activity, the resinification of the reaction mixture) can be regenerated by vacuum distillation and returned to the process. The value included in the probe amines is not limited and, as a rule, corresponds to the products produced by the industry, for example, this PEPA grade B (TU 6-02-1099-83).

In the composition of the used catalyst may include any, including equal the ratio of amine DETA, THETA and TAP; or DETA and THETA or TAP; or THETA and TAP.

In all cases achieved the desired results.

EXAMPLE 1 (comparative, the prototype)

In a metal reactor, made of steel 12X18H10T 0.5 DM3equipped with a mixer, siphon, shirt, thermocouple and pressure gauge, load 88 g (1 mol) EA and 6 g (0.03 mole) of tungsten trioxide. The reactor is hermetically closed with a lid include mixing and cooling of the circulating water. At a temperature of 8-10°C in the reactor through the siphon from the tank, installed on the scales, load 90 g (2 mol) DMA. Siphon choke and served in the jacket of the reactor coolant - silicone oil, adjusting the temperature in the reactor to 120°C. due to evaporation DMA at a given temperature the pressure in the reactor increases to 10 kgf/cm2. Given these parameters, the process is carried out for 20 hours. Then the reactor is cooled to a temperature of 20-30°C, equalize the pressure in the reactor to atmospheric and unload the reaction mixture. The mixture is sent to a vacuum distillation. The result DMAA in the amount of 46.5 g (yield 54% of theoretical). Analysis of the reaction mixture and the DMAA is performed on a gas chromatograph NR. The following results are obtained: conversion of EA was 80%, the content of the basic substance - 99,0%.

Example 2

In the reactor of example 1 load 88 g (1 mol) EA and 4.4 g (0,03 mole) of Triethylenetetramine (THETA). The reactor was sealed, cooled and served from a cylinder 135 g (3 mol) DMA. Heat the reactor to pace atory 110°C, the pressure in the reactor increases up to 9 kgf/cm2. Given these parameters, the process is carried out for 10 hours. After discharge of the reaction mixture, separation DMAA and analysis get the following results: conversion of EA was 95%, the content of the basic substance is 99.93%. Output DMAA was 89.6%.

Similarly, conduct other experiments, examples and results are presented in Table 1.

As follows from Table 1, the output DMAA more than 85% conversion EA more than 90% at high product purity of more than 99.9% is achieved by using as catalysts as individual ethylenamine: DEATH metal, THETA, TAP, and mixtures thereof in the range of 0.03 to 0.1 mol per 1 mol of the original EA in 2-3-fold molar excess of DMA in the temperature range of 80-120°C (see Table 1, PP, 3, 7, 11-16). Reduction of the catalyst to less than 0.03 mole and DMA less than 2 moles or more low temperature less than 80°C leads to lower conversion of the EA, and to reduce the output of DMAA (see Table 1, PP, 6, 9). An excess of catalyst is more than 0.1 mole and DMA more than 3.0 moles already has no significant effect on conversion and output DMAA (see Table 1, PP, 8), and the increase in temperature over 120°C leads to a sharp decrease in the conversion and output DMAA due to apparently increase the speed side processes, which affects the quality of the target product (the content basis of the aqueous substances of less than 98%) (see Table 1, p.10).

Differences of the developed method of obtaining DMAA-based EA and DMA from the known method (see Table 1, item 1) is that the proposed new catalysts that can increase output DMAA 5-10% and improve the quality of the target product (the content of the basic substance more than 99.9%). In addition, enhanced, simplified phase separation of the catalyst from the products of interaction.

Thus, the problem facing the authors developed a new and effective way of getting DMAA from cheap and available raw materials, using an inexpensive catalyst that allows to minimize loss DMAA and get a high quality product with high yield.

td align="center"> THETA
Table 1
No. op.Number of downloads on synthesisCatalystThe temperature of the synthesis, °CPressure, kgf/cm2Conversion of EA, % wt.The content of basic substance, % wt.Output DMAA, % wt.
Uh the DMAnamenumber
gmolgmolgmol
12345678910111213
188,01,090,02,0WO36,00,031201080,0to 99.0054,0
288,01,0135,03,0THETA4,4 0,03110995,099,9389,6
388,01,090,02,0THETA4,40,03110991,299.91 per85,0
488,01,067,51,5THETA4,40,03110884,099,9078,0
588,01,0157,53,5THETA5,80,04110895,199,92to 89.5
688,01,0112,52,5THETA2,90,021201084,099,9079,0
788,01,0135,03,0THETA14,60,1080690,099,9385,0
888,01,090,02,0THETAof 21.90,151008to 91.199.91 per86,0
988,01,0135,03,013,10,0970478,498,5070,8
1088,01,0112,02,5THETA11,70,081301282,497,2075,6
1188,01,090,02,0DEATH metal8,20,081201093,299,9288,4
1288,01,0112,02,5TAP9,50,0512010 99,9390,0
1388,01,0135,03,0№2+№11 (1:1)10,0-110893,299.91 perto 89.5
1488,01,0135,03,0№11+№12 (1:1)11,0-110894,399,9289,6
1588,01,0112,02,5№2+№12 (1:1)11,0-110894,499,9289,8
1688,0 1,0112,02,5№2+№11+№12 (1:1:1)to 12.0-110894,099.91 per89,2

1. The method of obtaining N,N-dimethylacetamide by the interaction of ethyl acetate (EA) and N,N-dimethylamine (DMA) in the presence of aminecontaining catalyst, characterized in that the interaction is carried out at a temperature of 80-120°C. using as a catalyst polyethylenepolyamines (PEP) formula NH2[(CH2CH2)NH]n-1CH2CH2NH2where n=2÷4.

2. The method of receiving according to claim 1, characterized in that the catalyst is one of the compounds of the formula NH2[(CH2CH2)NH]n-1CH2CH2NH2where n=2, 3, or 4.

3. The method of receiving according to claim 1, characterized in that the process is carried out at a molar ratio of downloads EA:DMA:PEPA=1:(2÷3):(0,03÷0,1).



 

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