Preparation method for catalyst for hydrogenation reduction reaction of 2-alkylene cyclobutanone

A technology of hydrocarbyl cyclobutanone and catalyst, which is applied in catalyst activation/preparation, carbon-based compound preparation, organic compound preparation and other directions, can solve problems such as being easily destroyed, and achieve the effects of easy operation, easy preparation and less solid waste

Active Publication Date: 2017-08-25
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, it is quite challenging to implement this scheme
The main reason is that 2-alkylene cyclobutanone is a kind of highly active substance, if it is hydrogenated under high pressure and high temperature, it will be easily destroyed
Moreover, in addition to the double bond in this molecule, the carbonyl group is more active and easier to be reduced, so there is a challenging problem of selectivity control

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 1. Preparation of catalyst: Under ice-water bath, mix 20 mL of ethanol solution containing sodium borohydride with a concentration of sodium borohydride of 1 mol / L and 20 mmol of selenium powder (the molar dosage is 100% of sodium borohydride) and 0.6 mmol of additives 3-isopropylselenyl-2-alanine (molar dosage is 0.03 times of sodium borohydride) is mixed, and then 6 mmol of p-dibenzyl chloride (molar dosage is 30% of sodium borohydride) is added dropwise, after mixing evenly, The mixture was then heated to 45° C. with stirring for 24 hours of reaction. After the reaction is finished, filter and take the solid phase to obtain the selenium-containing high polymer. The solid was soaked in 0.3 mol / L palladium nitrate aqueous solution for 24 hours, filtered, washed with deionized water, and dried to obtain the catalyst.

[0018] 2. Application: Add 1 mmol 2-benzylidene cyclobutanone and 10 mg catalyst into 10 mL tetrahydrofuran, flow hydrogen at normal temperature and pre...

Embodiment 2

[0020] Other conditions are the same as in Example 1, and the activity of catalysts prepared by ethanol solutions of different concentrations of sodium borohydride is checked, and the experimental results are shown in Table 1.

[0021] Table 1 Test of activity of catalysts prepared with different concentrations of sodium borohydride

[0022] serial number Sodium borohydride concentration (mol / L) Normal temperature and pressure hydrogenation yield 1 0.2 51 2 0.5 72 3 1.0 82 (Example 1) 4 1.5 70 5 2.0 61

[0023] From the above results, it can be seen that when the content of sodium borohydride in the ethanol solution of sodium borohydride is 1.0mol / L, the catalytic hydrogenation yield of the catalyst obtained by the reaction is the highest, reaching 82%.

Embodiment 3

[0025] Other conditions are the same as in Example 1, and the activity of the catalyst prepared by different selenium powder dosages is tested, and the experimental results are shown in Table 2.

[0026] The test of catalyst activity prepared by different selenium powder consumptions of table 2

[0027] Molar amount of selenium powder / Molar amount of sodium borohydride 50% 80% 100% 150% 200% Normal temperature and pressure hydrogenation yield / % 46 76 82 (Example 1) 80 72

[0028] As can be seen from the above results, the catalytic hydrogenation yield of the catalyst obtained when the amount of selenium powder is 100% of the molar weight of sodium borohydride is the highest, reaching 82% (Example 1).

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PUM

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Abstract

The invention discloses a preparation method for a catalyst for hydrogenation reduction reaction of 2-alkylene cyclobutanone and relates to the technical field of production of 2-substituted cyclobutanone. The method comprises the steps of firstly preparing a selenium-containing high polymer through reaction of sodium borohydride, selenium powder, dihalide and 3-isopropenyl-2-amino-propionic acid, and adsorbing palladium, wherein the obtained catalyst has unique reaction activity and is capable of catalyzing the 2-alkylene cyclobutanone at the atmospheric pressure and the room temperature to prepare the 2-substituted cyclobutanone. The used selenium-containing high polymer of the palladium-loaded catalyst is easy to prepare, low in dosage and high in yield and can be recycled for multiple times.

Description

technical field [0001] The invention relates to the technical field of production of 2-substituted cyclobutanones, in particular to the preparation technology of catalysts for preparing 2-substituted cyclobutanones by hydrogenation reaction of 2-alkylene cyclobutanones at normal pressure and room temperature. Background technique [0002] 2-Substituted cyclobutanones are important intermediates in drug synthesis and are widely used in the synthesis of drugs and natural products. For example, in α-Bisabolol, (-)-Debromofiliformin, (-)-Filiformin, (±)-Scirpene, (±)-a-Cuparenone, (±)-Herbertene In the synthesis of all of them, 2-substituted cyclobutanone is used as the key synthon. At present, the methods for synthesizing such compounds generally have long synthetic routes, use complex reagents, and are costly and wasteful. [0003] The inventors have found through research that using calcium hydroxide as a catalyst can catalyze the condensation of cyclobutanone and aldehy...

Claims

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Application Information

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IPC IPC(8): B01J31/28B01J31/12B01J37/02C07C45/62C07C49/657
CPCB01J31/123B01J31/28B01J37/0201C07C45/62C07C49/657
Inventor 俞磊李梦璇张旭
Owner YANGZHOU UNIV
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