The method of producing formamide

 

(57) Abstract:

Usage: mainly organic synthesis. The inventive product - formamid. Reagent 1 : HCOOH. Reagent 2: NH3. Reaction conditions: interaction of lead with 30-110oIn the presence of water at a mass ratio of water : acid 1:1-20, with subsequent decomposition of obrazuyushcheisya salt at 150-180oIn the presence of NH3when the molar ratio of HCOOH : NH31:0.1 to 1.0. table 2.

The invention relates to the field of organic synthesis, more specifically a process for the production of formamide.

Known [1] a method of producing wavelengths from carbon monoxide and ammonia at a temperature of 80 100oC and a pressure of 30 to 100 MPa in the environment of an organic solvent. The catalyst of alkali metals in the form of a salt or alcoholate. The yield reaches 96%

The disadvantage of this method is the necessity of the implementation process at high pressure.

A known method of producing wavelengths of methylformate and ammonia [2]

The process is carried out in a reaction column in the environment of the boiling methylformate. The resulting formamide displays the bottom of the column for subsequent separation and purification from impurities.

The failure of obtaining substituted formamides, such as dimethylformamide (DMF), by reacting formic acid with gaseous dimethylamine in two stages: at first obtaining a salt of formate, dimethylamine, the second decomposition of this salt in DMF, with each stage of the process is carried out in two stages. As presented in the description of the example in the first stage the first stage gaseous dimethylamine is passed at a temperature of 60 70oWith over loaded in the reactor formic acid taken in the quantity of 50% of design. After complete bonding acid dimethylamine (analysis on methyl red) is transferred to the second stage first stage: in the reaction solution obtained in the first stage, and through which continue to barbthroat dimethylamine, gradually add the second half of the calculated quantity of formic acid. The result of the reaction solution of the first stage formate, dimethylamine. In the second stage of the process decomposition of formate in DMF also carried out in two stages. The first stage is used as raw material 50% from those obtained in the first stage of formate, which is placed in a reactor equipped with a distant column, and in which when the temperature of the top of column 100oWith distilled water mixed with dimethylamine in the volume is erha column to 125 130oC, and the temperature in the reactor to 145 150oWith and begin to drive away, in the form of condensable vapors, dimethylformamide, water and dimethylamine, at the same time in the reactor gradually begin to dispense the second half of the solution of dimethylamine formate obtained in the first stage of the process. The output of dimethylformamide, according to the authors, is 90 to 95% formic acid.

The disadvantage of this method is the complexity and multiple proposed technology requiring more details concerning operations, proportions, etc. in Addition, this method applies only to the synthesis of dimethylformamide and does not describe the receipt of formamide.

Closest to the technical nature of the solution is the method of obtaining formamide in two stages by reacting formic acid with ammonia, the latter is used to implement the process in the bound form in the form of urea [4] the Process is carried out at elevated temperature in two stages: the first stage uses excess acid to increase the speed and completeness of linking the input in the form of urea, ammonia, and in the second stage, formed by decomposition of ammonium formate, the synthesis is carried out at theoi acid (corresponding to a molar ratio of acid ammonia, equal to 1 1,01 - 1,03). The yield of the target product is 65%

The disadvantage of the prototype is the low yield of the desired wavelengths; the use of expensive raw materials; the process is technically imperfect, because the original urea difficult to dose in the reaction zone due to the fact that it is solid. The process is environmentally imperfect: in the synthesis of large amount of gases to 5 tons per 1 ton of the target product.

To the above review ways of formamide formic acid and ammonia should be added to information from sources, for example, [5] or [6] which in General describes a method of producing amides from acids and ammonia or primary or secondary amines in the presence of an excess of the original acid. But in these sources in any form not to mention obtaining in this way of formamide formic acid and ammonia.

This is due to the peculiarity inherent only formic acid: during storage, especially when heated (boiling, distillation) formic acid decomposes to CO2and H2[7] As well as for carrying out the amidation process it is necessary to maintain the elevated temperature, it will always be a decomposition of the acid results in this case: the interaction of the acid with ammonia as an intermediate connection of ammonium formate and then decomposing it into formamid. The yield of the desired product by the method prototype 65%

It should also be noted that the implementation of the process of obtaining of formamide formic acid and ammonia through the ammonium formate is not as obvious and simple as it is described for use with high molecular weight acids [5,6] the fact that the target formamide formed by the following reaction equation:

< / BR>
may undergo further transformations of the scheme:

< / BR>
forming a strong poison prussic acid [6] the Ability of formamide to undergo these transformations formed the basis of industrial technology of the synthesis of hydrocyanic acid, for example [8] or the next member of the homologous series of acetonitrile [9] For more effective implementation of these transformations, carried out in the presence of dehydrating catalysts.

This cause the formation of hydrocyanic acid, pushed up to the present time, research on the safe synthesis of formamide acid and ammonia, while offering a safer synthesis of methylformate and ammonia [2]

The purpose of the present invention increase the efficiency of the process and increase the yield of the target wavelengths.

To achieve these goals the acid with ammonia at elevated temperature with the formation of the intermediate ammonium formate and subsequent decomposition to formamide, thus the distinguishing feature of the proposed method is that the interaction of formic acid with ammonia propose to perform in the presence of water, taken in a weight ratio to the acid water acid), equal to 1 1-20 and at a temperature of 30 110oC, and the decomposition of ammonium formate in formamid carried out at a temperature of 150 160oIn the presence of ammonia, taken in a molar ratio of the initial formic acid ammonia equal to 1 0,1 1,0.

In accordance with the proposed solution process is as follows (see also the description of the example). Source formic acid is mixed with water in a mass ratio of water to acid in the range of from 1 1 to 1 to 20 and the resulting solution was dosed ammonia, maintaining the temperature of the reaction mixture 30 110oC. Stabilization of the temperature of the reaction mixture reached through the use of forced cooling (water "shirt" on the reactor vessel and the built-in coil) and "know-how" of the proposed method the supply of liquid ammonia in the acid solution. The heat of the exothermic reaction between the acid and the ammonia is removed endothermic effect evaporation of liquid ammonia (boiling point of liquid ammonia 39oC).

The resulting warm solution at a temperature of 150 180oWith the passing through it of gaseous ammonia in a molar ratio of the original acid ammonia 1 0,1 1,0, waving at the top of the column and water accumulating in the cube reactor target formamid.

Received in Cuba reactor formamid without additional purification used in the production of vitamin b1.

Application at the stage of obtaining ammonium formate water additives can improve the yield of the desired wavelengths to 96.3% of the original acid by reducing the degree of decomposition of the acid CO2and H2; to reduce the loss of ammonia lost by binding to its eye-catching Co2in carbamino acid. In addition, the use of water additives allows to simplify the technology.

The simplification of the process is due to the fact that the formed intermediate ammonium formate in anhydrous conditions for synthesis of the crystalline substance with a melting point 116o"Scores" of the reaction space. Thus formed ammonium formate enters into wsimages solubility of ammonium formate in the reaction solution.

In the proposed by the present invention method, the ammonium formate is dissolved in the formation in the reaction solution containing the water.

Obtained at this stage is the end product of a solution of ammonium formate in water, can be easily transported in the decomposition reactor. If the process is carried out in one apparatus, and in this case reach the positive effect of further improving the yield of the target product are achieved by a uniform supply of heat to the fluid, while the heating of the solid ammonium formate leads to local overheating and loss of raw materials from degradation products and resinification.

The invention, in the opinion of the applicants meet the conditions of patentability. It is new, because applicants are not aware of any sources that provide data on the use of water additives in the synthesis of formamide from acid and ammonia.

It has an inventive level, because not obvious from the prior art. First of all, because in the literature there are no data on the positive influence of addition of water to the reaction for the synthesis of amides from acids and amines.

The obviousness of the proposed solution Tamarasheni acid.

The present invention is industrially applicable, because its implementation does not require any special equipment or inaccessible and expensive raw materials.

The method is illustrated by the following examples, the main results are also listed in the summary table.2.

In examples 1 to 4 presents the results obtained according to the invention in the claimed range. In examples 1 and 2 presents the results of, respectively, the lower and upper bounds of the claimed parameters. The deviation of process parameters for the claimed range (examples 5 to 9) does not give a positive effect (increasing output formamide). Example 9 to obtain formamide water without additives.

Example 1.

The feedstock formic acid in the amount of 122 grams and has a feature: basic substance content of 99.5 wt.%. impurities up to 100% t Kip. 100,8oC, d2401.22 g/cm3placed in the reactor, representing a three-neck flask equipped with a bubbler, a thermometer, a reflux condenser, placed in a water bath. Charged to the reactor distilled water in the amount of 6.1 g, which is the ratio of water to acid is 1 to 20. Then in the traditional mass is placed in a reactor dehydration, representing a three-neck flask equipped with a thermometer, a bubbler, a Packed column ( d= 25 mm, h= 500 mm, nozzle stainless spiral with a diameter of 3 mm) with straight-through refrigerator, placed in an oil bath.

The reaction mixture obtained in the first stage, heat at a temperature of 180oWith, barbotine through her ammonia in the amount of 45.0 g (the molar ratio of acid ammonia 1 1,0)

Top of the Packed column select water with dissolved ammonia; dissolved in water ammonia catch 50% aqueous solution of sulfuric acid.

Within 2 hours in the receiver gather of 64.5 g of an aqueous ammonia solution containing 15.9 g of dissolved ammonia. The amount of ammonia absorbed 50% acid solution, determined by weight and is, 33,46

The balance of the experiment is shown in table.1.

Analysis of the reaction products by the methods of gas-liquid chromatography and non-aqueous potentiometric titration showed that the conversion of the acid is 98,9% (including ammonium formate as not turned acid), and the selectivity of the conversion of formic acid in formamide (output) is 90.5% of theoretical.

The information in example 1 and other examples are given in the summary that is as in example 1 was loaded into the reactor and carry out the synthesis as described in example 1, except that the quantity of water added is 122 g (the ratio of water to acid is 1 1), the saturation temperature of the acid with ammonia 30oC, the reaction mixture obtained in the first stage heat at a temperature of 150oWith, the supply of ammonia to the second stage 4.5 g, which is the molar ratio of acid ammonia equal to 1 by 0.1.

Analysis of the reaction products showed that the conversion of the acid is 95,1% with the selectivity of the process 93,8% of theoretical.

Example 3.

The synthesis is carried out in the conditions described in example 1, except that the amount of added water is 24.4 g (the ratio of water to acid is 1 to 5), the temperature of the saturated acid 100oC, the temperature of the second stage 160oWith, the supply of ammonia 13.5 g (the molar ratio of acid ammonia 1 0,3).

Analysis of the reaction products showed that the conversion of the acid is 98.5% Yield of formamide to 96.3% of theoretical.

Example 4.

The synthesis is carried out in the conditions described in example 1, except that the amount of added water is 61 g (the ratio of water to acid is 1 to 2), the saturation temperature of the acid with ammonia 40oWith the temperature of decomposition of the formate and the>/P>Analysis of the product showed that the conversion of acid 98.6% of output wavelengths for 96.1% of theoretical.

Example 5.

The synthesis is carried out as in example 4, except that the temperature of the saturated acid with ammonia 20oC. Conversion of the acid to 96.8% yield of formamide 88.2% of theoretical.

Example 6.

The synthesis is carried out as in example 4, except that the temperature of the saturated acid with ammonia 120oC. Conversion of acid 99.8% of the Output of formamide 80.7% of theoretical.

Example 7.

The synthesis is carried out as in example 4, except that the decomposition of ammonium formate in the second stage is conducted without addition of ammonia. Conversion of acid 56.5% of Output wavelengths to 82.1% of theoretical.

Example 8.

The synthesis is carried out as in example 4, except that the decomposition of ammonium formate in the second stage is carried out in the presence of ammonia, taken in an amount of 49.5 g (the molar ratio of acid ammonia 1 to 1.1). Conversion of acid 98.6% of the Output wavelengths of 96.2% of theoretical.

Example 9.

Synthesis is carried out as in example 4, except that the saturation of the acid with ammonia hold water without additives. Conversion of the acid to 95.7% You the acid with ammonia at elevated temperature and subsequent decomposition of the resulting salt in a stream of ammonia at a temperature of 150-180°C, characterized in that the interaction of formic acid with ammonia is carried out at a temperature 30-110°C in the presence of additives water, taken in the mass ratio of water: acid = 1:1-20, and decomposition of the salt is carried out in the presence of ammonia at a molar ratio of acid: ammonia = 1:0.1 to 1.0.

 

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