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Preparation of bicyclohexyl neopentyl glycol single ketal

A technology of pentylene glycol monoketal and neopentyl glycol, which is applied in the fields of chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., and can solve the problem of troublesome operation process, large environmental pollution, Complicated preparation methods, etc.

Active Publication Date: 2009-04-15
HEBEI MAIERSTON ELECTRONICS MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, ethylene glycol monoketal is basically used for protection, which is described in patent US4,910,350 and US5,089,629; in the patent US20040046150, there is neopentyl glycol monoketal in the cyclohexyl bridge, but There is no introduction of bicyclohexyl monoketal; from the current domestic production practice, the conversion rate of ethylene glycol monoketal is generally about 70%; the principle of use is: the double protected compound is insoluble in saturated sodium bisulfite solution In the middle, thereby filtering out the double protection; then one and two carbonyl double bonds can undergo addition reaction with sodium bisulfite, and the generated sodium sulfonate is insoluble in saturated sodium bisulfite solution, thus crystallization Different in sequence, isolated monoketal and dicyclohexyl diketone. In the whole production process, the operation process is troublesome and time-consuming, the labor intensity is high, the reaction conversion rate is low, and the final yield is also low (based on 100Kg of bicyclodiketone , can obtain GC≥98.5% single ketal about 40Kg), in addition, use multiple mixed solvents to be unfavorable for the recycling of solvent, make production cost bigger, environmental pollution is big; Conducive to the subsequent preparation of single crystals such as alkenes
[0010] Therefore, in order to overcome defects such as complex preparation method in the prior art, high production cost and large environmental pollution, this invention is specially proposed

Method used

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  • Preparation of bicyclohexyl neopentyl glycol single ketal
  • Preparation of bicyclohexyl neopentyl glycol single ketal
  • Preparation of bicyclohexyl neopentyl glycol single ketal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] In a 250ml reaction bottle, add 7.76g of dicyclohexyl diketone, 9.95g of neopentyl glycol, that is, the molar ratio of cyclohexyl diketone to neopentyl glycol is 0.7 and 200ml of inert solvent cyclohexane, mix well and add strong 2 g of acidic cation exchange resin was allowed to react at 35° C. for 5.5 h during stirring, and then the resin was removed by filtration to obtain a mixed solution of dicyclohexyl neopentyl glycol monoketal.

[0043] The above-mentioned mixed solution is heated and evaporated until the solvent in the mixed solution is evaporated to dryness, and 500ml of acetone and water mixed solution are added to the obtained solid, and the volume of acetone in the mixed solution of acetone and water accounts for 15% of the total volume. %, the mixed solution was cooled, then filtered, and the filtrate was taken.

[0044] Continue to add 500 mL of water to the above filtrate, then stir for 30 minutes until the solution is uniformly mixed and then filter, an...

Embodiment 2

[0047] In a 2500ml reaction flask, add 98.94g of dicyclohexyl diketone, 59.6g of neopentyl glycol, i.e. the mol ratio of cyclohexyl diketone to neopentyl glycol is 0.9 and 2000ml of inert solvent cyclohexane, mix well and add strong 5.96 g of acidic cation exchange resin was heated to 50° C. for 6 h during stirring, and then the resin was removed by filtration to obtain a mixed solution of dicyclohexyl neopentyl glycol monoketal.

[0048] The above mixed solution was heated and evaporated until the solvent in the mixed solution was evaporated to dryness, and then added to the obtained solid in a mixed solution of 3000ml acetone and water, the volume of acetone in the mixed solution of acetone and water accounted for 20% of the total volume, stirred for 1 hour, then filtered, and the filtrate was taken.

[0049] Continue to add 2000 mL of water to the above filtrate, then stir for 30 minutes until the solution is uniformly mixed and then filter, and recrystallize the obtained s...

Embodiment 3

[0052] In a 250ml reaction bottle, add 11.64g of dicyclohexyl diketone, 6.35g of neopentyl glycol, that is, the molar ratio of cyclohexyl diketone to neopentyl glycol is 1.1 and 200ml of inert solvent cyclohexane, mix well and then add 1.3 g of strongly acidic cation exchange resin was heated to 110° C. during the stirring process, and after reflux and water separation for 3 hours, the resin was removed by filtration to obtain a mixed solution of dicyclohexyl neopentyl glycol monoketal.

[0053] The above-mentioned mixed solution is heated and evaporated until the solvent in the mixed solution is evaporated to dryness, and then added to the obtained solid in a mixed solution of 400ml acetone and water, the volume of acetone in the mixed solution of acetone and water accounts for 1% of the total volume 25%, cooled, and then filtered to get the filtrate.

[0054] Continue to add 300ml of water to the above filtrate, then stir for 30 minutes until the solution is uniformly mixed,...

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Abstract

The invention relates to preparation of an organic compound, in particular to a method for preparing dicyclohexyl pentanediol mono-ketal and belongs to the technical field of organic compound preparation. The method takes dicyclohexyl diketone and neopentyl glycol as the raw materials to carry out the catalytic reaction under the catalyst of inert solvent cyclohexane and strong acid cation exchange resin, the reaction temperature is 0 to 110 DEG C, the dicyclo mono-ketal is prepared, and the conversion rate can reach 80 to 95 percent; simultaneously, dicyclohexyl pentanediol mono-ketal with high yield and high purity is obtained by acetone-water system, and the method is beneficial to later preparation of mono-crystalline, alkene and the like.

Description

technical field [0001] The invention relates to a preparation of organic compounds, in particular to a preparation method of dicyclohexylpentanediol monoketal, which belongs to the technical field of preparation of organic compounds. Background technique [0002] Cyclohexyl diketone monoketal: such as 1,4-cyclohexyl diketone ethylene glycol monoketal and 4,4'-bicyclohexyl diketone ethylene glycol monoketal, used in medicine, pesticides, spices, liquid crystal display materials And synthetic intermediates and other aspects have very important applications. [0003] Courtot, P (Bull.SOC.Chim, Fr 1962.1943-1944) reported that 1,4-cyclohexanedione was refluxed with equimolar ethylene glycol to obtain 1,4-cyclohexanedione, 1,4-cyclohexyl The mixture of diketone monoethyl ketal and 1,4-cyclohexanedione diethyl ketal, the content ratio is 1:1:1; 1,4-cyclohexanedione is soluble in water to remove, and the residue Sodium bisulfate treatment (1,4-cyclohexanedione diethyl ketal does ...

Claims

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Application Information

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IPC IPC(8): C07D407/04B01J31/08
Inventor 仲锡军杜自飞张丽梁建国
Owner HEBEI MAIERSTON ELECTRONICS MATERIAL
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