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Preparation method of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde

A technology of cyclohexylcarbaldehyde and cyclohexylmethanol is applied in the field of preparation of trans-4-(trans-4′-alkylcyclohexyl)cyclohexylcarbaldehyde, which can solve the problem of high industrialization danger, large acid chloride pollution and high preparation cost problem, to achieve the effect of convenient industrial production, mild reaction conditions and low preparation cost

Inactive Publication Date: 2010-09-08
吴小会
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Chinese patent CN02103898.8 discloses that trans-4-(trans-4'-alkylcyclohexyl)cyclohexyl formic acid is used as a raw material, and trans-4-(trans-4'-alkyl cyclohexyl rings are prepared through lithium aluminum hydride reduction. Hexyl)cyclohexylmethanol, and then oxidized by chromium trioxide pyridine hydrochloride (PCC) to generate trans-4-(trans-4'-alkylcyclohexyl)cyclohexylcarbaldehyde. The raw materials used in this method are expensive and produce Chromium waste, easy to cause environmental pollution
This method has the following problems: 1. Acyl chloride pollution is large, and the by-products sulfur dioxide and hydrogen chloride gas are large to environmental pollution and pose a great threat to the health of operating workers
2. The palladium carbon catalyst is used in the reduction process, which belongs to the noble metal catalyst, and the cost is high
3. The triethylsilane used in the reduction process is a flammable liquid, which is more dangerous in industrialization and higher in cost
[0008] However, currently commercially available trans-4-(trans-4'-alkylcyclohexyl)cyclohexyl formic acid is composed of trans-4-(trans-4'-alkylcyclohexyl)cyclohexyl formic acid and cis-4-( The mixture of trans-4'-alkylcyclohexyl)cyclohexylcarboxylic acid is obtained by purification after isomerization of cyclohexane, and this step of isomerization reaction needs to be carried out at high temperature, therefore, more energy is consumed and the reaction yield is higher. The rate is relatively low, resulting in the cost price of trans-4-(trans-4'-alkylcyclohexyl)cyclohexylcarboxylic acid being higher than that of trans-4-(trans-4'-alkylcyclohexyl)cyclohexylcarboxylic -Mixtures of (trans-4'-alkylcyclohexyl)cyclohexylcarboxylates are much more expensive
Thereby cause the preparation cost of final product anti-4-(anti-4'-alkylcyclohexyl) cyclohexyl formaldehyde is also higher
This limits the application of liquid crystal materials in conventional fields to a certain extent

Method used

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  • Preparation method of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde
  • Preparation method of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The structural formula is Wherein, R is the preparation of the compound of n-propyl.

[0049] Step (a): make trans-4-(trans-4'-n-propylcyclohexyl)cyclohexyl formic acid (IA), cis-4-(trans-4'-n-propylcyclohexyl)cyclohexyl formic acid ( The mixture of I B) is reduced to generate trans-4-(trans-4'-n-propylcyclohexyl)cyclohexylmethanol (IIA), cis-4-(trans-4'-n-propylcyclohexyl)cyclohexylmethanol (IIB )mixture.

[0050] Add 1 L of tetrahydrofuran into a 5 L three-necked flask, and protect it with nitrogen. After turning on the stirring, 272g (2mol) of zinc chloride and 76g (2mol) of sodium borohydride were quickly added, and cis-4-(trans-4'-n-propylcyclohexyl)cyclohexylcarboxylic acid, trans-4-(trans -4'-n-propylcyclohexyl)cyclohexyl formic acid mixture 252g (1mol), wherein cis-4-(trans-4'-n-propylcyclohexyl)cyclohexyl formic acid content is 45.2% (GC), trans-4 The content of -(trans-4'-n-propylcyclohexyl)cyclohexylcarboxylic acid is 54.4% (GC), and the rest are trace i...

Embodiment 2

[0068] The structural formula is Wherein, R is the preparation of the compound of n-butyl.

[0069] Step (a): Make a mixture of trans-4-(trans-4'-n-butylcyclohexyl)cyclohexyl formic acid (IA) and cis-4-(trans-4'-n-butylcyclohexyl)cyclohexyl formic acid (IB) Reduction produces a mixture of trans-4-(trans-4'-n-butylcyclohexyl)cyclohexylmethanol (IIA), cis-4-(trans-4'-n-butylcyclohexyl)cyclohexylmethanol (IIB).

[0070]Add 1 L of tetrahydrofuran into a 5 L three-necked flask, and protect it with nitrogen. After turning on the stirring, 272g (2mol) of zinc chloride and 76g (2mol) of sodium borohydride were quickly added, and cis-4-(trans-4'-n-butylcyclohexyl)cyclohexylcarboxylic acid, trans-4-(trans-4 '-n-butylcyclohexyl)cyclohexyl formic acid mixture 238g (1mol), wherein, cis-4-(trans-4'-n-butylcyclohexyl)cyclohexyl formic acid content is 97.2% (GC), trans-4-(trans-4 The content of '-n-butylcyclohexyl)cyclohexyl formic acid is 2.4% (GC), and the rest are trace impurities. St...

Embodiment 3

[0082] The structural formula is Wherein, R is the preparation of the compound of n-pentyl.

[0083] Step (a): Make trans-4-(trans-4'-n-pentylcyclohexyl)cyclohexyl formic acid (IA), cis-4-(trans-4'-n-pentylcyclohexyl)cyclohexyl formic acid ( The reduction of the mixture of IB) generates trans-4-(trans-4'-n-pentylcyclohexyl)cyclohexylcarbinol (IIA), cis-4-(trans-4'-n-pentylcyclohexyl)cyclohexylcarbinol (IIB )mixture.

[0084] Add 1 L of tetrahydrofuran into a 5 L three-necked flask, and protect it with nitrogen. After turning on the stirring, 272g (2mol) of zinc chloride and 76g (2mol) of sodium borohydride were quickly added, and cis-4-(trans-4'-n-pentylcyclohexyl)cyclohexylcarboxylic acid, trans-4-(trans -4'-n-pentylcyclohexyl)cyclohexyl formic acid mixture 280g (1mol), wherein, cis-4-(trans-4'-n-pentylcyclohexyl)cyclohexyl formic acid content is 2.2% (GC), trans- The GC content of 4-(trans-4'-n-pentylcyclohexyl)cyclohexylcarboxylic acid is 97.5% (GC), and the rest are t...

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Abstract

The invention discloses a preparation method of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde, comprising the steps of reducing a mixture of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formic acid and cis-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formic acid to generate a mixture of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl methanol and cis-4-(trans-4'-alkyl cyclohexyl)cyclohexyl methanol; making the mixture of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl methanol and the cis-4-(trans-4'-alkyl cyclohexyl)cyclohexyl methanol undergo oxidation reaction so as to generate a mixture of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde and cis-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde; and carrying out cyclonexane isomerization on a mixture of trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde (IIIA) and cis-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde (IIIB) under an acidic condition to obtain trans-4-(trans-4'-alkyl cyclohexyl)cyclohexyl formaldehyde (IIIA). In the invention, the preparation method has low production cost, is environment friendly, and is suitable for mass industrialized production.

Description

technical field [0001] The present invention relates to the preparation method of the compound containing -CHO group, specifically the preparation method of trans-4-(trans-4'-alkylcyclohexyl)cyclohexylcarbaldehyde. Background technique [0002] Trans-4-(trans-4'-alkylcyclohexyl)cyclohexylcarbaldehyde is an important intermediate for the preparation of cyclohexane liquid crystal materials. With the increasingly wide application of liquid crystal display technology, the preparation of cyclohexane liquid crystal materials and their important intermediate trans-4-(trans-4'-alkylcyclohexyl)cyclohexylcarbaldehyde, the advantages and disadvantages of production methods and the cost The level is more and more critical to whether liquid crystal display technology can be widely used. [0003] Chinese patent CN02103898.8 discloses that trans-4-(trans-4'-alkylcyclohexyl)cyclohexyl formic acid is used as a raw material, and trans-4-(trans-4'-alkyl cyclohexyl rings are prepared through l...

Claims

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Application Information

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IPC IPC(8): C07C47/34C07C45/67C07C45/29C07C45/30
Inventor 吴小会
Owner 吴小会