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Preparation of organic carboxylic ether

A technology of organic carboxylate and its manufacturing method, which is applied in the field of producing α-hydroxycarboxylate from α-hydroxycarboxylic acid amide, and can solve the problems of high cost, high reaction temperature and long reaction time, etc.

Active Publication Date: 2009-05-20
CHINA PETROCHEM DEVMENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

U.S. Patent No. 4,055,590 discloses a method for producing an organic carboxylate with an organic carboxylic acid amide and methanol using a metal carboxylate compound as a catalyst and high temperature. The disadvantage is that the reaction temperature is high and the reaction time is as long as 6 hours; Japanese patent 53-141216 discloses a kind of organic carboxylic acid amide and alcohols in the presence of metal compounds and additives with chelating properties such as oxygen and nitrogen as catalysts, and a method for producing organic carboxylic acid esters under high temperature and high pressure conditions. In addition to the low conversion efficiency, the method needs to add additional expensive additives; Japanese patent 58-55444 discloses a kind of organic carboxylic acid amides and formic acid esters in B group metal compounds and oxygen, nitrogen and other additives with chelating properties as Catalyst and use a special alloy-HC as a reactor to manufacture organic carboxylic acid esters under high temperature and high pressure conditions. The conversion efficiency of this method is not high, and an additional cocatalyst needs to be added; US Patent 4613684 discloses an organic carboxylic acid A method for producing organic carboxylic acid esters under conditions of high temperature and high pressure in the presence of metal carbonyl compounds and tertiary amine compounds as catalysts for amides and formic esters or alcohol compounds. The catalyst system used in this patent is highly toxic and expensive and difficult to synthesize; U.S. Patent 4973739 discloses a kind of organic carboxylic acid amides and formic esters in solid acid as catalyst, the method for manufacturing organic carboxylate under high temperature condition; U.S. Patent 4983757 discloses a kind of organic carboxylic acid amides and formic esters or alcohol A kind of alkaline earth metal oxide is used as catalyst, the method for producing organic carboxylate under high temperature, high pressure condition; U.S. Patent 4990651 discloses a kind of organic carboxamide and formic acid esters or alcohols in sodium methylate as catalyst, at high temperature, The method for producing organic carboxylate under high pressure conditions, the activity of this method is not good, it takes a long time to reach equilibrium, and when utilizing other esters (such as ethyl formate) to carry out the reaction, in addition to needing methanol to be replaced by ethanol, also Sodium methylate needs to be replaced with sodium ethylate to avoid the generation of methyl ester compound and increase the problem of product separation; U.S. Patent 5,194,668 discloses a kind of organic carboxylic acid amide and formic acid esters or alcohols in alkali metal hydroxide as catalyzer, in A method of producing organic carboxylate under high temperature and high pressure conditions. In addition to the need to react under high pressure, the method must first dehydrate the reactant before the reaction, otherwise there will be organic carboxylic acid and ammonium carboxylate in the reaction. Compound generation; U.S. Patent 6310236 discloses a kind of organic carboxylic acid amides and alcohols in precious metal compound as catalyst, the method for manufacturing organic carboxylate under high temperature, high pressure condition, the shortcoming of this method is that catalyst preparation difficulty is high, and production cost is high , and the reaction must be carried out at a higher temperature

Method used

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  • Preparation of organic carboxylic ether
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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Place 8.07 g (0.078 mol) of α-hydroxyisobutyramide, 8.08 g (0.108 mol) of methyl acetate, 1.5351 g (0.039 mol) of sodium amide, and 22.62 g (0.707 mol) of methanol in a 130 mL stainless steel high-pressure in the reactor. The reactor is pressurized with carbon monoxide to 20kg / cm 2 Afterwards, the temperature of the reaction system was raised to 120° C. and the stirrer was turned on. The reaction time was 2 hours;

[0025] Table 1

[0026]

[0027] The experimental results in Table 1 show that using metal amides as amine transesterification catalysts can obtain good catalytic effect in the reaction.

Embodiment 2-5

[0029] Repeat the steps of Example 1, change the reaction temperature, cool the reaction solution after the reaction is over, and analyze the product with a gas chromatograph, the results are shown in Table 2.

[0030] Table 2

[0031]

Example

Reaction temperature (°C)

α-Hydroxyisobutyramide

Conversion rates(%) Methyl α-Hydroxyisobutyrate

Selectivity (%)

[0032] 2 60 31.09 90.23 3 80 51.68 79.08 4 100 52.70 79.29 1 120 51.08 88.10 5 150 48.63 86.15

[0033] The experimental results in Table 2 show that increasing the temperature increases the reaction conversion rate, but too high reaction temperature will increase the reaction rate of the reverse reaction and reduce the reaction conversion rate.

Embodiment 6-9

[0035] Repeat the steps of Example 1, change the pressure of carbon monoxide in the reactor, cool the reaction solution after the reaction is over, and analyze the product with a gas chromatograph, the results are shown in Table 3.

[0036] table 3

[0037]

[0038] The experimental results in Table 3 show that increasing the reaction pressure can increase the conversion rate and simultaneously increase the selectivity of the product, but too high a reaction pressure may induce the occurrence of side reactions and reduce the reaction selectivity.

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Abstract

The invention discloses a production method of organic carboxylic ether, which includes a method that amine-ester exchange reaction is carried out to organic carboxylic acid amide and an ester or alcohol compound in the presence of a catalyst and under the conditions of specific temperature and carbon monoxide pressure for the production of the organic carboxylic ether.

Description

technical field [0001] The present invention relates to the manufacture method of organic carboxylic acid ester, more specifically, relate to organic carboxylic acid amide and ester class or alcohol compound carry out amine transesterification reaction under the condition of specific temperature and carbon monoxide pressure in the presence of catalyst to produce organic carboxylic acid A method for esters, particularly a method for producing α-hydroxycarboxylic acid esters from α-hydroxycarboxylic acid amides. Background technique [0002] Organic carboxylic acid esters are important chemical raw materials in the petrochemical industry. They can be used in fiber, synthetic rubber, industrial coatings, medicine, pesticides and organic solvents, etc., and have a wide range of uses. Most organic carboxylates are produced by the reaction of organic carboxylic acids and alcohols, but in some specific petrochemical production processes, organic carboxylates are obtained by alcohol...

Claims

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Application Information

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IPC IPC(8): C07C67/20C07C69/675B01J27/24
Inventor 李进义蔡嘉荣
Owner CHINA PETROCHEM DEVMENT
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