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A method for co-producing methyl benzyl alcohol, methyl benzaldehyde and methyl benzoic acid

A technology of methyl benzaldehyde and methyl benzoic acid, applied in chemical instruments and methods, carboxylate preparation, carbon-based compound preparation, etc., can solve the problems of many by-products, difficult separation, long reaction time, etc., and achieve activity high effect

Active Publication Date: 2017-05-31
山东友道化学有限公司
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  • Summary
  • 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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  • A method for co-producing methyl benzyl alcohol, methyl benzaldehyde and methyl benzoic acid
  • A method for co-producing methyl benzyl alcohol, methyl benzaldehyde and methyl benzoic acid
  • A method for co-producing methyl benzyl alcohol, methyl benzaldehyde and methyl benzoic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Add 550g o-xylene into a 1L batch oxidation reactor, and add 600ppm (concentration in o-xylene) of HfO 2 , N-hydroxy sulfonyl benzamide, metal phthalocyanine with general formula (IV) structure (R 1 =H, R 2 =F, M=Fe) and metalloporphyrin (R) with the structure of general formula (I) 1 =R 3 =OH, R 2 =H, M=Ru) is the catalyst, 27.5g of o-carboxybenzaldehyde and o-phthalaldehyde is the mixture of co-oxidant, and then 1.2MPa of air is continuously introduced, and the tail oxygen concentration is controlled by controlling the amount of air. Not more than 5%, keep the pressure in the reactor at 0.8 MPa and the temperature at 145° C. to continuously stir the reactants, stop the reaction after 1.6 hours, quickly cool the reactants and take samples for analysis. The analysis result of liquid chromatography showed that the conversion rate of o-xylene was 8.8%, the total selectivity of alkyd in the final oxidation product was 98.5%, and the total selectivity of aldol was 88.2%. The ...

Embodiment 2

[0060] In a 1L batch oxidation reactor, add 550g of o-xylene, and add 660ppm (concentration in o-xylene) of N-hydroxy-4-nitrophthalimide, with the general formula ( IV) Metal phthalocyanine of structure (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) is a catalyst, 16.6g o-methylbenzaldehyde is a co-oxidant, and then 2.0MPa of air is continuously introduced. By controlling the amount of air introduced, the tail oxygen concentration is controlled not to exceed 5%, and the pressure in the reactor is maintained at The reactant was continuously stirred under the conditions of 1.6 MPa and the temperature of 130° C., the reaction was stopped after 1.4 hours, and the reactant was quickly cooled and sampled for analysis. The analysis result of liquid chromatography showed that the conversion rate of o-xylene was 6.8%, the total selectivity of aldol in the final oxidation product was 98.8%, and the total selectivity of aldol was 90.9%. The sel...

Embodiment 3

[0062] In a 1L batch oxidation reactor, add 550g of p-xylene, and add 800ppm (concentration in p-xylene) of cobalt naphthenate, metal phthalocyanine with general formula (IV) structure (R 1 =CH 3 CH 2 , R 2 =H, M = Mn), metal porphyrin (R 1 =R 2 =H, R 3 =CH 3 , M=Cu) is a catalyst, 99.0g of p-carboxybenzyl alcohol, p-methylbenzaldehyde and p-methylbenzyl alcohol is a mixture of co-oxidant, and then 1.0MPa of air is continuously introduced by controlling the air inflow The volume control tail oxygen concentration does not exceed 5%, and the reactant is continuously stirred under the conditions of maintaining the pressure in the reactor at 0.5 MPa and the temperature at 130°C. The reaction is stopped after 5.0 hours, and the reactant is quickly cooled and sampled for analysis. The analysis result of liquid chromatography showed that the conversion rate of p-xylene was 11.9%, the total selectivity of aldol in the final oxidation product was 98.0%, and the total selectivity of aldol ...

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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 methylbenzyl alcohol, methylbenzaldehyde and methylbenzoic acid by oxidation of xylene. Background technique [0002] Methylbenzyl alcohol, methylbenzaldehyde and methylbenzoic acid are all important organic chemical intermediates, which are generally produced by the reaction of xylene under high temperature and high pressure. Since the two methyl groups on the benzene ring can be oxidized step by step, there are many deep oxidation products, and product separation is difficult. So far, the industrial products of xylene can only be obtained by air oxidation of phthalic acid or methyl benzoic acid. There is no industrial report on the oxidation of xylene to methyl benzyl alcohol or methyl benzaldehyde. Chinese patent CN1333200A discloses a method for catalyzing air oxidation of xylene into methylbenzaldehyde, methylbenzyl alcohol and methylbenzoic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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