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Method for synthesizing 4-(4'-n-alkyl cyclohexyl)cyclohexanone

A synthesis method and the technology of alkyl rings, which are applied in the field of synthesis of important liquid crystal intermediate 4-cyclohexanone, can solve the problems of serious environmental pollution and low yield, and achieve low oxidation cost, low price and simple synthesis process Effect

Active Publication Date: 2009-01-07
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

"Newly Edited Organic Synthetic Chemistry" (written by Huang Xian, Wang Yanguang, etc., p287-289) introduces several main methods of oxidation of secondary alcohols: 1. Chromium oxide oxidation method, this method uses chromium trioxide / sulfuric acid as oxidant, will A large amount of chromium-containing acidic wastewater is produced, causing great pressure on the environment
2. The dimethyl sulfoxide oxidation method uses dimethyl sulfoxide as an oxidant, and after the reaction, waste water containing dimethyl sulfoxide will also be produced, which seriously pollutes the environment
3. Sodium hypochlorite oxidation method, the reaction uses sodium hypochlorite as an oxidant, but the reaction will generate chlorinated by-products, resulting in low yield

Method used

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  • Method for synthesizing 4-(4'-n-alkyl cyclohexyl)cyclohexanone
  • Method for synthesizing 4-(4'-n-alkyl cyclohexyl)cyclohexanone
  • Method for synthesizing 4-(4'-n-alkyl cyclohexyl)cyclohexanone

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Effect test

Embodiment 1

[0013] Add 2.3g (0.007mol) of sodium tungstate dihydrate, 2.0g (0.0007mol) of phosphotungstic acid, and 34g of hydrogen peroxide (30% by mass) into a 250mL three-necked flask with a reflux condenser, and stir for 15 minutes , the solution changed from yellow to pale yellow. Add 22.4 (0.1 mol) g of 4-(4'-n-propylcyclohexyl) cyclohexanol (II) and 144 g of N-methylpyrrolidone to the above reaction system, and heat to keep the system temperature at 90°C. After 5 hours, the reaction was analyzed by gas chromatography, and the heating was turned off. Change the reaction device to a vacuum distillation device, distill N-methylpyrrolidone and cool to room temperature, then extract with petroleum ether, dry over anhydrous sodium sulfate, filter to remove the desiccant, and obtain 4-(4'-n- Propylcyclohexyl)cyclohexanone (I) 20.2g, yield 91.0%.

[0014] IR(KBr)v / cm -1 : 2954, 2919, 2850, 1719, 1464, 1448GC-MS (EI): 222 (M + ), 204, 166

[0015] 13 C NMR, δ C : 215.10, 43.42, 42.81...

Embodiment 2

[0017] Other conditions are the same as in Example 1, and the temperature of the heating system is maintained at 80°C. After 8 hours, the reaction was analyzed by gas chromatography to obtain 20.0 g of 4-(4'-n-propylcyclohexyl)cyclohexanone with a yield of 90.1%.

Embodiment 3

[0019] Other conditions were the same as in Example 1, 23.8 (0.1 mol) g of 4-(4'-n-butylcyclohexyl)cyclohexanol was added to obtain 22.1 g of 4-(4'-n-butylcyclohexyl)cyclohexanone with a yield of 93.6%.

[0020] IR(KBr)v / cm -1 : 2951, 2918, 2855, 1717, 1466, 1450GC-MS (EI): 236 (M + ), 218, 180

[0021] 13 C NMR, δ C : 216.80, 43.54, 32.81, 44.51, 45.11, 33.06, 36.90, 40.77, 40.07, 32.14, 25.83, 16.26

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Abstract

The invention relates to a synthesis method of 4-(4'-n-alkyl cyclohexyl) cyclohexanone, which comprises the following steps: mixing and stirring sodium tungstate dehydrate and phosphotungstic acid; adding hydrogen peroxide to obtain an oxidant; adding reactant 4-(4'-n-alkyl cyclohexyl) chclohexanol and a solvent N-methylpyrrolidinone in the oxidant; and reacting to obtain 4-(4'-n-alkyl cyclohexyl) cyclohexanone. The hydrogen peroxide is an ideal clean oxidant, and the byproduct of the reaction is water. The synthesis method has simple process and high yield. The synthesis method is a green 4-(4'-n-alkyl cyclohexyl) cyclohexanone synthesis method.

Description

technical field [0001] The present invention relates to a kind of synthetic method of important liquid crystal intermediate 4-(4'-n-alkyl cyclohexyl) cyclohexanone, and its structural formula is as shown in (I): [0002] [0003] In the formula, R is a linear alkyl group with 1 to 7 carbon atoms. Background technique [0004] Cyclohexane-based liquid crystals are liquid crystals containing a cyclohexane skeleton, and are favored by people because of their high stability and wide nematic phase temperature range. After replacing the benzene ring with cyclohexane, the π electron system decreases, the charge distribution density decreases, and the polarization is weakened, so the melting point is lower, but its clearing point tends to increase. Another advantage of using cyclohexane instead of benzene ring is the reduction of viscosity, which overcomes the disadvantages of high viscosity and slow response speed of liquid crystals containing benzene ring skeletons that are st...

Claims

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Application Information

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IPC IPC(8): C07C49/427C07C45/39
Inventor 杨永忠刘骞峰高仁孝吴鑫琦李涛余勇徐云侠房发俐
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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