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Combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid

A technology of benzyl alcohol and benzaldehyde, which is applied in the field of preparation of aromatic compounds, can solve the problems of unsuitable for large-scale production, low production efficiency and high production cost, and achieve the effects of improving utilization rate, saving energy consumption and reducing the probability of production

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

This method is generally aimed at specific aldehydes or alcohols, and is produced through complex organic synthesis methods. The production efficiency is generally low, and a large amount of intermediate organic substances will be used, resulting in a large amount of three wastes. The production cost is high and it is not suitable for large-scale production.

Method used

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  • Combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid
  • Combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid
  • Combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The catalyst dissolved in the fresh material p-chlorotoluene and acetic acid 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), the total concentration is 600ppm, and the mass ratio of solvent to p-chlorotoluene is 0.026. When the device is in steady state operation, the flow rate of fresh material added to the oxidation reactor is 6.2mL / h. At this time, the average residence time of the oxidation reactor in terms of liquid phase substances is 2.4h, and the pressurized pure oxygen is continuously introduced into the oxidation reactor. In the reactor, the reaction temperature of the system is maintained at 165° C., and the reaction pressure is 1.4 MPa. The volume ratio of the amount of water added to the hydrolysis reactor to the oxidation reaction solution entering the hydrolysis reactor is 0.33:1, and oxygen-depleted air...

Embodiment 2

[0062] The catalyst that dissolves in the fresh o-fluorotoluene that adds in the primary oxidation reactor is the metal phthalocyanine (R with general formula (IV) structure 1 = H, R 2 =CH 3 CH 2, M=Co) and a mixture of manganese acetylacetonate, the total concentration is 450ppm. When the device is in steady state operation, the flow rate of fresh o-fluorotoluene added to the oxidation reactor is 10.9mL / h. At this time, the average residence time of the oxidation reactor in terms of liquid phase substances is 2.2h, and the pressurized pure oxygen is continuously passed through into the oxidation reactor to maintain the reaction temperature of the system at 185°C and the reaction pressure at 1.7MPa. The volume ratio of the amount of water added to the hydrolysis reactor to the oxidation reaction liquid entering the hydrolysis reactor is 0.90:1, and the reaction temperature in the hydrolysis reactor is maintained at 144°C, and the reaction pressure is 1.2MPa. At this time, t...

Embodiment 3

[0064] The catalyst dissolved in the fresh material p-bromotoluene and acetic acid 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, the total concentration is 120ppm, and the mass ratio of acetic acid to p-bromotoluene is 0.056. When the device is in steady state operation, the flow rate of fresh material added to the oxidation reactor is 14.5mL / h. At this time, the average residence time of the oxidation reactor in terms of liquid phase material is 1.5h, and the pressurized pure oxygen is continuously introduced into the oxidation reactor. In the reactor, the reaction temperature of the system is maintained at 190° C., and the reaction pressure is 1.8 MPa. The volume ratio of the amount of water added to the hydrolysis reactor to the oxidation reaction solution entering the hydrolysis reactor is 0.28:1, ...

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Abstract

The invention discloses a combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid. The method comprises the following steps: (1) oxidation: a step of continuously introducing substituted toluene, a catalyst and oxygen-contained gas into an oxidation reactor and carrying out reaction so as to obtain oxidation reaction liquid; (2) hydrolyzation: a step of allowing the oxidation reaction liquid to continuously enter a hydrolysis reactor, and continuously adding water into the hydrolysis reactor and carrying out reaction so as to obtain a hydrolysis reaction mixture; (3) liquid-liquid layering: a step of layering the hydrolysis reaction mixture so as to obtain an oil phase and an aqueous phase; and (4) separation of products: a step of subjecting the oil phase to distillation so as to respectively obtain incompletely-reacted substituted toluene, substituted benzyl alcohol and substituted benzaldehyde, and subjecting the aqueous phase to cooling, crystallizing and filtering so as to obtain filtrate and substituted benzoic acid. The combined production method provided by the invention has the advantages of high raw material conversion rate, few by-products, good selectivity of target products, greenness and environmental protection.

Description

technical field [0001] The invention relates to a preparation method of aromatic compounds, in particular to a method for co-producing substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid. Background technique [0002] Benzoic acid, benzyl alcohol and benzaldehyde, which are substituted by different substituents such as halogen, nitro, methyl, cyano, thiamphenyl, hydroxyl, methoxy, etc. on the benzene ring, are important fine chemical products and are widely used in Pharmaceutical, pesticide, veterinary drug, food, dyestuff, organic synthesis and other industries have very considerable market prospects. At present, there are four methods for industrially producing substituted benzyl alcohol, substituted benzaldehyde and substituted benzoic acid: [0003] (1) Halogenated substituted toluene and then hydrolyzed. The product produced by this method has high selectivity, but this method has many production steps and complex process conditions. The ...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07B41/06C07B41/08C07C45/36C07C47/55C07C63/70C07C51/265C07C33/46C07C29/50C07C27/12C07C201/12C07C205/22C07C205/44C07C205/57C07C253/30C07C255/53C07C255/56C07C255/57C07C31/133C07C63/04C07C315/04C07C317/22C07C317/24C07C317/44C07C39/11C07C47/565C07C65/03C07C47/542C07C33/20C07C205/58C07C47/575C07C65/21
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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