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

A technology of methyl benzaldehyde and methyl benzyl alcohol, which is applied in chemical instruments and methods, separation/purification of carboxylic acid compounds, preparation of carboxylate, etc., can solve low reaction efficiency, loss of methyl benzyl alcohol, reaction time Long-term problems, to achieve the effect of increasing utilization, improving economy, and avoiding side effects

Active Publication Date: 2016-01-13
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
The common post-treatment process of the industrial production method is to adopt rectification to separate the unreacted raw materials and products, which not only consumes a large amount of heat energy, but also in the rectification process, methyl benzaldehyde is easily heated and reacts with the alcohol in the system. Loss, methyl benzyl alcohol is easy to be heated and the acid in the system is esterified and lost, resulting in a large amount of residue in the distillation tower and low product yield, generally not more than 80%

Method used

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

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Experimental program
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Effect test

Embodiment 1

[0065] The catalyst dissolved in fresh p-xylene added to the system is 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) with a total concentration of 600 ppm. When the device is in steady state operation, the flow rate of fresh p-xylene added to the primary oxidation reactor is 15.7mL / h, and the flow rate of the circulating oil phase rich in eight-carbon oxygenates and p-xylene is 125.0mL / h. The total flow rate of the oxidation reactor was 140.7 mL / h. At this time, the average residence time of the primary oxidation reactor in terms of liquid phase substances is 1.6h, and the pressurized pure oxygen is continuously fed into the primary oxidation reactor to maintain the system reaction temperature at 179°C and reaction pressure at 0.6MPa. The flow rate of water added to the secondary oxidation reactor is 46.8mL / h. At this time, the volume ratio of th...

Embodiment 2

[0067] The catalyst that dissolves in the fresh p-xylene that adds in the primary oxidation reactor is cobalt naphthenate and the metal phthalocyanine (R with general formula (IV) structure 1 = H, R 2 =CH 3 CH 2 , M=Co) mixture with a total concentration of 45 ppm. When the device is running in a steady state, the flow rate of freshly reacted p-xylene added to the primary oxidation reactor is 33.8mL / h, and the flow rate of the circulating oil phase rich in eight-carbon oxygenates and p-xylene is 60.1mL / h. The total flow into the primary oxidation reactor was 93.8 mL / h. At this time, the average residence time of the primary oxidation reactor in terms of liquid phase substances is 2.4 hours, and pressurized pure oxygen is continuously fed into the primary oxidation reactor to maintain the system reaction temperature at 185°C and reaction pressure at 2.2MPa. The flow rate of water added to the secondary oxidation reactor is 84.5mL / h. At this time, the volume ratio of the amo...

Embodiment 3

[0069] The catalyst dissolved in fresh p-xylene added to the primary oxidation reactor is Mn(Ac) 2· 4H 2 O, metal phthalocyanine (R) with general formula (IV) structure 1 = NO 2 , R 2 =H, M=Co), the metalloporphyrin (R 1 = R 3 = H, R 2 =CH 3 CH 2 , M=Cu) mixture with a total concentration of 120ppm. When the device is running in a steady state, the flow rate of freshly reacted p-xylene added to the primary oxidation reactor is 43.8mL / h, and the flow rate of the circulating oil phase rich in eight-carbon oxygenates and p-xylene is 106.3mL / h. The total flow into the primary oxidation reactor was 150.1 mL / h. At this time, the average residence time of the primary oxidation reactor in terms of liquid phase substances is 1.5h, and the pressurized pure oxygen is continuously fed into the primary oxidation reactor to maintain the system reaction temperature at 175°C and reaction pressure at 0.7MPa. The flow rate of water added to the secondary oxidation reactor is 42.0mL / h....

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Abstract

The invention discloses a coproduction method of methyl benzoic acid, methyl benzaldehyde, and methyl benzyl alcohol. The method comprises the following steps: (1) primary oxidation: continuously introducing xylene, a catalyst and oxygen-containing gas into a primary oxidation reactor to carry out reactions to obtain a primary oxidation reaction liquid; (2) secondary oxidation: continuously introducing the primary oxidation reaction liquid into a secondary oxidation reactor, and continuously introducing water and oxygen-containing gas into the secondary oxidation reactor to carry out reactions to obtain a secondary oxidation reaction mixture; (3) liquid-liquid layering: introducing the secondary oxidation reaction mixture into a liquid-liquid layering device to carry out layering to obtain an oil phase in the upper layer and a water phase in the lower layer, and returning the oil phase to the primary oxidation reactor; (4) water phase separation: separating and purifying the water phase to obtain methyl benzoic acid, methyl benzaldehyde, and methyl benzyl alcohol. The method has the advantages of high raw material conversion rate, high product yield, good selectivity of target product, and environment-friendliness.

Description

technical field [0001] The invention relates to a method for preparing aromatic compounds, in particular to a method for co-producing methylbenzoic acid, methylbenzaldehyde and methylbenzyl alcohol. Background technique [0002] Toluene benzoic acid can be used as an intermediate of medicine, pesticide, organic pigment and whitening agent, etc. Its preparation methods mainly include xylene nitric acid oxidation method, xylene air oxidation method, toluene carbonylation-oxidation method, etc., which are the most economical and effective The method is the xylene air oxidation method. 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 alcohol and methyl benzoic acid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/50C07C33/22C07C45/36C07C47/54C07C51/235C07C51/48C07C51/487C07C63/06
CPCC07C29/50C07C45/36C07C51/235C07C51/48C07C51/487C07C33/22C07C47/54C07C63/06
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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