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Coproduction method of methyl benzyl alcohol, methyl benzaldehyde, and methyl benzoic acid

A technology of methyl benzaldehyde and methyl benzoic acid is applied in chemical instruments and methods, carboxylate preparation, carbon-based compound preparation, etc., and can solve the problems of many by-products, low product selectivity, difficult separation and the like, achieve high activity

Active Publication Date: 2016-01-13
山东友道化学有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] (1) The reaction time is too long, which needs 8-12h, which leads to low reaction efficiency, high equipment investment and actual operation cost of industrial production;
[0004] (2) The total selectivity of p-toluene alcohol and p-tolualdehyde is low, and the content of p-toluic acid with relatively low added value is relatively high in the product
This is also the reason why the product selectivity is not high, the final by-products are many, and the separation is difficult when the selective oxidation of xylene is used in industry to produce methyl benzyl alcohol, methyl benzaldehyde, and methyl benzoic acid.

Method used

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  • Coproduction method of methyl benzyl alcohol, methyl benzaldehyde, and methyl benzoic acid
  • Coproduction method of methyl benzyl alcohol, methyl benzaldehyde, and methyl benzoic acid
  • Coproduction method of methyl benzyl alcohol, methyl benzaldehyde, and methyl benzoic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] In a 1L batch oxidation reactor, add 550g of o-xylene, and add 600ppm (concentration in o-xylene) by HfO 2 , N-hydroxyl o-sulfonyl benzamide, metal phthalocyanine (R) with general formula (IV) structure 1 = H, R 2 =F, M=Fe) and metalloporphyrins (R 1 = R 3 =OH,R 2 =H, M=Ru) the mixture that forms is catalyst, and the mixture that 27.5g o-carboxybenzaldehyde and o-phthalaldehyde forms is the air that feeds 1.2MPa continuously after the co-oxidant, controls tail oxygen concentration by controlling the intake of air No more than 5%, the reactants were continuously stirred under the conditions of maintaining the pressure in the reactor at 0.8MPa and the temperature at 145°C, and the reaction was stopped after 1.6 hours, and the reactants were rapidly cooled and then sampled for analysis. The analysis results of liquid chromatography showed that the conversion rate of o-xylene was 8.8%, the total selectivity of alkyd acid in the final oxidation product was 98.5%, and the...

Embodiment 2

[0059] In a 1L batch oxidation reactor, add 550g of o-xylene, and add 660ppm (concentration in o-xylene) of N-hydroxyl-4-nitrophthalimide, having the general formula ( IV) metal phthalocyanine (R 1 =NH 2 , R 2 =H, M=Cu) and the metalloporphyrin (R 1 = R 3 = H, R 2 =CH 3 ,M 1 = M 2 =Cr) The mixture that forms is catalyzer, and 16.6g o-methylbenzaldehyde is the air that feeds 2.0MPa continuously after the co-oxidant, by controlling the intake of air, the tail oxygen concentration is controlled to be no more than 5%, and the pressure in the reactor is maintained to be The reactant was continuously stirred under the conditions of 1.6MPa and 130°C, and the reaction was stopped after 1.4 hours. The reactant was rapidly cooled and then sampled for analysis. The analysis results of liquid chromatography showed that the conversion rate of o-xylene was 6.8%, the total selectivity of alkyd acid in the final oxidation product was 98.8%, and the total selectivity of aldol was 90.9%...

Embodiment 3

[0061] In a 1L batch oxidation reactor, add 550g of p-xylene, and add 800ppm (concentration in p-xylene) of cobalt naphthenate, metal phthalocyanine (R) with general formula (IV) structure 1 =CH 3 CH 2 , R 2 =H, M=Mn), the metalloporphyrin (R 1 = R 2 = H, R 3 =CH 3 , M=Cu) the mixture that forms is catalyzer, the mixture that 99.0g p-carboxybenzyl alcohol, p-tolualdehyde and p-methyl benzyl alcohol form is the air that feeds 1.0MPa continuously after the co-oxidant, by controlling the feeding of air Quantitatively control the tail oxygen concentration to not exceed 5%, keep the reactor internal pressure at 0.5MPa, and continuously stir the reactants at a temperature of 130°C, stop the reaction after 5.0 hours, quickly cool the reactants and take samples for analysis. The analysis results of liquid chromatography showed that the conversion rate of p-xylene was 11.9%, the total selectivity of alkyd acid in the final oxidation product was 98.0%, and the total selectivity of...

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Abstract

The invention discloses a coproduction method of methyl benzyl alcohol, methyl benzaldehyde, and methyl benzoic acid. The coproduction method comprises the following steps: mixing xylene, a co-oxidization agent (a C8 oxygen-containing compound), and a catalyst, and continuously introducing oxygen-containing gas to carry out reactions. By controlling the amount of the added oxygen-containing gas, the content of oxygen gas in tail gas is not more than 5%. The mass ratio of the co-oxidization agent (a C8 oxygen-containing compound) to xylene is 0.003-0.2:1, and the using amount of the catalyst is 10-10000 ppm of the weight of the xylene. The reaction temperature is 105 to 200 DEG C, the reaction pressure is 0.2 to 2.5 MPa, the reaction time is 0.4 to 5 hours, and the xylene is oxidized into a mixture of methyl benzyl alcohol, methyl benzaldehyde, and methyl benzoic acid in one step. The method has the advantages of mild reaction conditions, high product yield, good selectivity, green, and environment-friendliness.

Description

technical field [0001] The invention relates to a preparation method of aromatic compounds, in particular to a method for co-producing methyl benzyl alcohol, methyl benzaldehyde and methyl benzoic acid through the oxidation of xylene. Background technique [0002] Methyl benzyl alcohol, methyl benzaldehyde and methyl benzoic acid are all important organic chemical intermediates, generally formed by the reaction of xylene under high temperature and pressure. Because the two methyl groups on the benzene ring can be oxidized step by step, resulting in more deeply oxidized products and difficult product separation. So far, industrially, xylene can only be oxidized by air to obtain the industrial product phthalic acid or methylbenzoic acid, and there is no industrial report on the oxidation of xylene to produce methyl benzyl alcohol or methyl benzaldehyde. Chinese patent CN1333200A discloses a method for catalytic air oxidation of xylene into methyl benzaldehyde, methyl benzyl a...

Claims

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Application Information

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IPC IPC(8): C07C29/50C07C33/22C07C45/36C07C47/54C07C51/235C07C63/06
CPCC07C29/50C07C45/36C07C51/235C07C33/22C07C47/54C07C63/06
Inventor 王勤波熊振华陈楚雄
Owner 山东友道化学有限公司
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