Method for synthesis of toluene from 4-methyl-3-cyclohexene-1-carbaldehyde

A cyclohexene formaldehyde, methyl technology, applied in chemical instruments and methods, hydrocarbons, hydrocarbons, etc., can solve the problems of long process route and high energy consumption, and achieve simple reaction procedures, high selectivity, and high reaction efficiency. short route effect

Active Publication Date: 2017-06-23
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the production process of aromatics needs to be obtained under the conditions of catalyst and high temperature and high pressure. The process route is relatively long and the energy consumption is high. The development of short and efficient conversion technology is of great significance to industrial production.

Method used

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  • Method for synthesis of toluene from 4-methyl-3-cyclohexene-1-carbaldehyde
  • Method for synthesis of toluene from 4-methyl-3-cyclohexene-1-carbaldehyde
  • Method for synthesis of toluene from 4-methyl-3-cyclohexene-1-carbaldehyde

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Experimental program
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Embodiment 1

[0030] Preparation of supported catalysts: All supported catalysts were prepared by equal-volume impregnation method, with Pt / Al 2 o 3 As an example, the preparation process is as follows: Weigh 1.59g of chloroplatinic acid solution containing Pt 3.767wt%, add water to dilute to 3.6g, and 5.94g of alumina (ground to 60-80 mesh, specific surface area> 150m 2 / g, pore volume > 0.37m 3 / g, bulk density 710kg / m 3 ) in the solution, baked at 60°C for 4h, at 80°C for 1h, at 120°C for 12h, and calcined at 500°C for 4h in air, and then reduced to room temperature with hydrogen (60ml / min / g) at 300°C. After cooling down to room temperature, O 2 / N 2 Mixed gas (O 2 Volume content 1%) in passivation 4h, obtain 1wt%Pt / Al 2 o 3 .

[0031]According to the above method, Fe, Ru, Ir, Rh, Pd, Ni, etc., which may be supported by activated carbon, alumina, magnesia, silica, zirconia, titania, silica-alumina molecular sieve, phosphorus-aluminum molecular sieve, etc. One or more catalysts, ...

Embodiment 2

[0034] Embodiment 2: (Patent Document 2)

[0035] Add 200 mg of catalyst D (platinum-containing alumina) to a quartz tube with a total length of 300 mm and an inner diameter of 6 mm, heat it to 400 ° C, and circulate nitrogen as a carrier gas from the upper part of the reaction tube at a flow rate of 10 ml / min. 2 To remove moisture for carrier gas purging for 1 hour, the 4-methyl-3-cyclohexene formaldehyde obtained in Example 1 is injected into the vaporization chamber at 1.84g / h, under the flow of nitrogen It was supplied to the catalyst layer, and after reacting for 0.5 h, 767 mg of an organic layer was obtained from the collection vessel at the lower end of the reaction tube. According to GC-MS, the conversion rate of the substrate was 93%, the yield of p-xylene was 41%, and the yield of p-tolualdehyde was 4%. Compared with implementation example 3 (product is mainly toluene), the liquid space velocity of implementation example 2 is 9.2h -1 , the liquid space velocity of ...

Embodiment 3

[0037] 1wt% Pt / Al is filled in the tubular reactor (inner diameter 10mm) 2 o 3 (60-80 mesh) solid catalyst 1.0g, be heated to 400 ℃, with the flow velocity of 20ml / min, circulate as the nitrogen of carrier gas from the top of reaction tube, with N 2 Purging the carrier gas for 1 hour to remove moisture, inject the 4-methyl-3-cyclohexene carboxaldehyde obtained in Example 1 into the vaporization chamber at 1 ml / h, and supply it under the guidance of nitrogen gas To the catalyst layer, after 1 hour of reaction, 724 mg of an organic layer was obtained from the collection vessel at the lower end of the reaction tube. (If the product is completely toluene, only 696 mg in theory). The conversion rate and toluene yield were quantitatively calculated in combination with GC-MS, and the reaction results are listed in Table 1.

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Abstract

The invention relates to a method for selective preparation of toluene from 4-methyl-3-cyclohexene-1-carbaldehyde. Specifically speaking, the method comprises the following steps: dehydrogenation and aromatization reaction as well as decarbonylation reaction of 4-methyl-3-cyclohexene-1-carbaldehyde are carried out under the effects of a supported type metal catalyst at 200-400 DEG C, and toluene is prepared. The method can be carried out in a fixed bed reactor, or a fluidized bed reactor or a moving-bed reactor separately, and reaction raw materials are directly injected into a reaction tube, or the reaction raw materials pass a catalyst bed layer with purging of carrier gas, liquid space velocity can be controlled, and toluene is synthesized. The process has the advantages of simple reaction process, and high selectivity of target product; the substrates can be obtained by Diels-Alder reaction from isoprene and acrolein which are derived from biomass resources and are used as raw materials, and a new route for preparing toluene from biomass is provided.

Description

technical field [0001] The invention relates to a method for selectively preparing toluene from p-methylcyclohexene formaldehyde (also known as: 4-methyl-3-cyclohexene formaldehyde, English name: 4-Methyl-3-cyclohexene-1-carbaldehyde). Specifically, it is a method in which 4-methyl-3-cyclohexene formaldehyde undergoes dehydroaromatization and decarbonylation reactions at 200°C-400°C under the action of a supported transition metal catalyst to generate toluene. The present invention is carried out in a gas-solid phase reactor, and the reaction raw materials are purged by the carrier gas to reach the catalyst bed, and undergo a catalytic reaction to obtain toluene; the reaction raw materials can also be injected into the catalyst bed by a syringe pump to react to obtain toluene. The process has simple reaction procedure, high selectivity of target product, and the substrate can be obtained from isoprene and acrolein through Diels-Alder reaction. However, isoprene and acrolein c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/06C07C1/207B01J23/42B01J23/46B01J23/44B01J23/755B01J29/44B01J23/89
Inventor 张涛代弢李昌志王爱琴丛昱张波李为臻郭海威
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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