Process for synthesizing p-tertiary butyl benzaldehyde

A technology of p-tert-butyltoluene and p-tert-butyl, which is applied in the field of selective oxidation of p-tert-butyltoluene to synthesize p-tert-butylbenzaldehyde, can solve the problems of equipment corrosion, many reaction steps and high production costs, and achieves easy separation. , Improve selectivity and avoid the effect of deep oxidation

Active Publication Date: 2009-05-27
格林生物科技股份有限公司
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  • Abstract
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  • Application Information

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Problems solved by technology

The stoichiometric oxidation method is in MnO 2 , concentrated H 2 SO 4 Directly oxidize p-tert-butyltoluene to synthesize p-tert-butylbenzaldehyde under the influence of the action. This process has equipment corrosion and serious pollution, and generates a large amount of MnSO 4 Disadvantages such as difficult recovery, high production cost, and difficult product separation
Although the benzyl chloride hydrolysis process is mature, it has many reaction steps and low yield, and the product contains trace organic chlorine that is not easy to remove, which is carcinogenic, and produces a large amount of sodium chloride or calcium chloride wastewater in the subsequent treatment section , causing serious pollution to the environment
[0004] Chinese patents (CN1944368A,...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 2% Co-HMS preparation: According to Micromeritics ASAP2010 physical adsorption instrument, the pore volume of HMS is 0.95cm 3 / g, the pore volume of 3g pure silicon mesoporous molecular sieve HMS is 2.85cm 3 , it is calculated that the volume of ethanol to be added per 3 g of pure silicon mesoporous molecular sieve HMS is 2.85 mL. Assuming that the cobalt load is 2%, it is calculated that 3g of HMS needs to be added with Co(NO 3 ) 2 ·6H 2 O is 0.3024 g. 0.3024g Co(NO 3 ) 2 ·6H 2O was dissolved in 2.85mL ethanol to obtain impregnating solution A (concentration 7.8%). Add 3g of HMS, stir evenly, make it fully wet, soak at room temperature for 4 hours and then dry at 80°C for 12 hours. The impregnated sample was roasted at 550°C for 4h.

[0028] Oxidation reaction: Add 100mg2% of the above-prepared Co-HMS catalyst, 6ml of acetonitrile, 5mmol of p-tert-butyltoluene, and 0.25mmol of N-hydroxyphthalimide to a 25ml three-necked pear-shaped flask equipped with a reflux c...

Embodiment 2

[0030] 4% Co-HMS preparation: According to the Micromeritics ASAP2010 physical adsorption instrument, the pore volume of HMS is 0.95cm 3 / g, the pore volume of 3g pure silicon mesoporous molecular sieve HMS is 2.85cm 3 , it is calculated that the volume of ethanol to be added per 3 g of pure silicon mesoporous molecular sieve HMS is 2.85 mL. Set the cobalt loading as 4%, it is deduced that Co(NO 3 ) 2 ·6H 2 O is 0.6173g. 0.6173g Co(NO 3 ) 2 ·6H 2 O was dissolved in 2.85mL ethanol to obtain impregnation solution A (concentration 14.7%). Add 3g of HMS, stir evenly, make it fully wet, soak at room temperature for 4 hours and then dry at 80°C for 12 hours. The impregnated sample was roasted at 550°C for 4h.

[0031] Oxidation reaction: add 100mg4% Co-HMS catalyst, 6ml acetonitrile, 5mmol p-tert-butyltoluene, 0.25mmol N-hydroxyphthalimide (p-tert-butyl The mass ratio of toluene to N-hydroxyphthalimide to catalyst to acetonitrile is: 1:0.055:0.135:6.3), magnetically stirred,...

Embodiment 3

[0033] The preparation of 4% Co-HMS is the same as in Example 2.

[0034] Oxidation reaction: add 200mg4%Co-HMS catalyst, 8ml acetonitrile, 5mmol p-tert-butyltoluene, 0.5mmol N-hydroxyphthalimide (p-tert-butyl The mass ratio of methyl toluene and N-hydroxyphthalimide to catalyst and acetonitrile is: 1:0.11:0.27:8.4), magnetically stirred, heated in an oil bath at a constant temperature of 70°C, and introduced O 2 , O 2 The flow rate is 1.5ml / min, stop feeding O after 7h of reaction 2 , the reaction mixture was cooled, separated, and the product was analyzed by GC, and the results are listed in Table 1.

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Abstract

The invention discloses a method for synthesizing p-tert-butylbenzaldehyde. The method comprises the following steps: a normal atmosphere heterogeneous catalytic oxidation method is adopted; p-tert-butyltoluene as a raw material, sufficient oxygen as an oxygen source and n-hydroxyphthalimide as a free radical evocating agent in an acetonitrile solution react for 4 to 7 hours at a temperature between 50 and 70 DEG C under the condition of a catalyst to directly synthesize the p-tert-butylbenzaldehyde; and the catalyst is a cobalt-loaded mesoporous molecular sieve or a cobalt- and manganese-loaded mesoporous molecular sieve. The method use the cobalt-loaded mesoporous molecular sieve or the cobalt- and manganese-loaded mesoporous molecular sieve as the solid-phase catalyst; compared with the prior liquid-phase catalyst, the target product is easier to separate after reaction; a reactant can rapidly contact catalytic activity center; product molecules rapidly escape from a pore canal, thereby avoiding deep oxidation and improving the selectivity of aldehyde; in addition, micro n-hydroxyphthalimide as the free radical evocating agent is added to the system to trigger the chain transmission reaction of free radicals.

Description

(1) Technical field [0001] The invention relates to a method for selectively oxidizing p-tert-butyl toluene to synthesize p-tert-butyl benzaldehyde under mild conditions. (2) Background technology [0002] 4-tert-butylbenzaldehyde is an important intermediate in fine chemical products such as medicines, dyes, flavors and fragrances, and is in great demand in the synthesis of flavors and fragrances lyral. [0003] There are many synthetic methods of p-tert-butylbenzaldehyde, and the traditional synthetic methods include stoichiometric oxidation and benzyl chloride hydrolysis. The stoichiometric oxidation method is in MnO 2 , concentrated H 2 SO 4 Directly oxidize p-tert-butyltoluene to synthesize p-tert-butylbenzaldehyde under the influence of the action. This process has equipment corrosion and serious pollution, and generates a large amount of MnSO 4 Disadvantages such as difficulty in recovery, high production cost, and difficulty in product separation. Although the b...

Claims

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Application Information

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IPC IPC(8): C07C47/542C07C45/33B01J29/03
Inventor 俞卫华陈伟琴周春晖胡建良童东绅
Owner 格林生物科技股份有限公司
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