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Process for preparing trans-1,2-naphthenic diol

A technology of cycloalkyl dihydric alcohol and epoxycycloalkane, which is applied in the field of synthesis of organic chemical products, can solve problems such as difficult separation of catalysts, and achieve the effects of improving effective utilization, reducing production costs, and fast reaction speed

Inactive Publication Date: 2014-07-16
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a method for producing trans 1,2-cycloalkyl diols in one step from epoxy cycloalkane and water in view of the problems of solvent use and catalyst separation difficulties in the existing production technology. craft

Method used

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  • Process for preparing trans-1,2-naphthenic diol

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Get 9.8g epoxycyclohexane and 9.0g water (epoxycyclohexane and water are 1:5 in molar ratio), place in reaction tank, airtight, be placed in oil bath, react at the temperature of 120 ℃ 6 hours. After cooling to 60°C, the reaction solution was decompressed to -0.098 MPa using a rotary evaporator and concentrated to dryness to obtain 10.6 g of trans-1,2-cyclohexanediol as a solid product. Product purity was determined by gas chromatography (GC-3420A of Beijing Analytical Instrument Factory, chromatographic column is PEG20000), the conversion rate of epoxycyclohexane was 100%, and the yield of cyclohexanediol was 100%. Following embodiment tests, analysis method is the same.

[0021] figure 1 The FT-IR spectrogram (KBr tablet, 400-4000cm -1 range content scan), by figure 1 Visible, 3385cm -1 The characteristic absorption peak of -OH is at -OH, and the reason for the large shift of the absorption peak of hydroxyl to low wave number is the hydrogen bond association in t...

Embodiment 2

[0023] The steps are the same as in Example 1, except that the present example takes 36g of water, and the molar ratio of epoxycyclohexane and water is 1:20. As a result of the reaction, the yield of cyclohexanediol was 100%.

Embodiment 3

[0025] The steps are the same as in Example 1, except that the reaction time of this example is 2 hours, and the reaction result is that the yield of cyclohexanediol is 80.1%. The crude product of trans 1,2-cycloalkyl diol obtained above was extracted with dichloroethane as solvent, recrystallized and suction filtered. The filter cake is washed with a small amount of dichloroethane and dried at about 60°C to obtain the pure trans-1,2-cyclohexanediol product.

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Abstract

The invention provides a process for preparing trans-1,2-naphthenic diol through direct synthesis of epoxy cycloalkane and water. The method comprises the following steps: putting epoxy cycloalkane and water in a reaction tank according to a mol ratio of epoxy cycloalkane to water of 1: 4-20, closing the reaction tank, heating an obtained mixture to a temperature of 100 to 140 DEG C under stirring and subjecting the mixture to a reaction for 2 to 10 h; drying liquid through vacuum concentration and evaporation so as to obtain the product of trans-1,2-naphthenic diol. According to the invention, a reaction speed is fast, no other catalyst is needed, and selectivity and yield of the product is high, higher than 99%; the reaction can be carried out in one reactor, and it is not needed to separate a catalyst, thereby simplifying and facilitating operation; a resultant polymer is oligomer which undergoes quick hydrolysis under the catalysis of high-temperature water to produce trans-1,2-naphthenic diol.

Description

technical field [0001] The invention relates to the synthesis of organic chemical products, in particular to a method for directly synthesizing trans 1,2-cycloalkyl diols from epoxy cycloalkane and water. technical background [0002] Cycloalkyl glycol is an extremely important organic chemical raw material. For example, cyclopentanediol can be used not only as a raw material for the preparation of polyester fibers, polyester resins, and organic medicines, but also for the preparation of plasticizers, surfactants, and emulsifiers. Another example is that 1,2-cyclohexanediol can be dehydroaromatized to generate catechol, produce 1,2-cyclohexanediol diglycidyl ether, synthesize crown ether, cleanly catalyze the synthesis of adipic acid, and esterify Cyclohexanediol diacrylate, polymerized to synthesize polyadipate 1,2-cyclohexanediol, oxidized to synthesize adipaldehyde, used to prepare various organic intermediates, mainly used in medicine, pesticides, advanced coatings, sur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/10C07C35/06C07C35/14C07C35/20C07C35/205
Inventor 王延吉杨雪杨秋生王海鸥张东升程庆彦薛伟
Owner HEBEI UNIV OF TECH
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