Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation method of 11-cyano undecanoic acid

A technology of undecanoic acid and cyano group, applied in the field of organic chemical industry, can solve the problems of no obvious increase in the yield of 11-cyanoundecanoic acid, obstacles to industrial production, complicated operation, etc., to avoid high-temperature thermal decomposition process, solve The effect of high temperature safety hazard is large and the preparation process is simple

Active Publication Date: 2021-09-07
WANHUA CHEM GRP CO LTD
View PDF8 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The document "Fine Chemical Intermediates" (2004, Vol. 34, No. 5, 31-33 pages) reported an improved PXA thermal decomposition process, using PXA and water vapor mixed feed, and replacing decompression by water vapor partial pressure System to realize the decompression of PXA, the thermal decomposition temperature can be reduced to 370-520 ° C, while the content of by-product caprolactam is controlled to less than 1%, the separation process of caprolactam is omitted, but the recovery of 11-cyanoundecanoic acid The yield did not increase significantly, and the highest yield was 57%
[0007] As can be seen above, using PXA as an intermediate and adopting the self-decomposition method to prepare 11-cyanoundecanoic acid still has shortcomings such as high reaction temperature, complicated operation, low product yield, and many by-products that are difficult to separate. High-temperature pyrolysis also increases the danger of the reaction, which brings obstacles to industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of 11-cyano undecanoic acid
  • A kind of preparation method of 11-cyano undecanoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 98 gram pimelinketone in flask, 136 gram 25wt% ammonia solution and 276 milligrams of salt of wormwood, slowly add 56.7 gram 30%wt hydrogen peroxide therein, react 120min at 20 ℃, through gas phase internal standard method (qualitative and quantitative) and 1 H NMR measurement (auxiliary qualitative) the conversion rate of cyclohexanone is 97.6%, the selectivity of PXA is 99.1%, and the yield of PXA is 96.7%.

[0032] Add 105.5 grams of PXA to the reaction flask, then add 51.2 mg of lutetium sulfate and 230 mg of dimethyl azobisisobutyrate, replace the flask with nitrogen for 3 times, react at 80 °C for 6 h, and then use the gas phase internal standard method and 1 H NMR determined that PXA was completely converted, the selectivity of 11-cyano undecanoic acid was 98%, and the yield of 11-cyano undecanoic acid was 98%.

Embodiment 2

[0034] Add 98 grams of cyclohexanone in the flask, 272 grams of 25wt% ammonia solution and 2.12 grams of sodium carbonate, slowly add 73.7 grams of 30%wt hydrogen peroxide therein, react 10min at 100 ℃, through gas phase internal standard method (qualitative and quantitative) and 1 H NMR measurement (auxiliary qualitative) the conversion rate of cyclohexanone is 98.5%, the selectivity of PXA is 99.3%, and the yield of PXA is 97.8%.

[0035] Add 211 grams of PXA to the reaction flask, then add 650 mg of lanthanum nitrate and 49.6 mg of azobisisoheptanonitrile, replace the flask with nitrogen for 3 times, react at 120 ° C for 3 h, and then use the gas phase internal standard method and 1 As determined by H NMR, PXA was completely converted, the selectivity of 11-cyano undecanoic acid was 97.5%, and the yield of 11-cyano undecanoic acid was 97.5%.

Embodiment 3

[0037] Add 49 grams of cyclohexanone in the flask, 102 grams of 25wt% ammonia solution and 814 milligrams of magnesium nitrate, slowly add 32.9 grams of 30%wt hydrogen peroxide therein, at 60 ℃ of reaction 65min, through gas phase internal standard method (qualitative and quantitative) and 1 H NMR measurement (auxiliary qualitative) the conversion rate of cyclohexanone is 98.8%, the selectivity of PXA is 98.5%, and the yield of PXA is 97.3%.

[0038] Add 211 grams of PXA to the reaction flask, then add 162 mg of samarium diiodide and 97 mg of benzoyl peroxide, replace the flask with nitrogen for 3 times, react at 100 ° C for 4.5 h, and then use the gas phase internal standard method and 1 H NMR determined that PXA was completely converted, the selectivity of 11-cyano undecanoic acid was 96.3%, and the yield of 11-cyano undecanoic acid was 96.3%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention relates to a kind of preparation method of 11-cyanoundecanoic acid, 1,1'-dicyclohexyl peroxide (PXA) undergoes self-decomposition reaction under the action of rare earth metal compound and free radical initiator, and highly selective To obtain 11-cyano undecanoic acid, PXA is generated by ammoxidation of cyclohexanone. The raw materials of the process line are simple and easy to obtain, avoiding the disadvantages of difficult control under high temperature conditions, low reaction selectivity, and difficult separation of products in the existing process, and provide a simple method for the preparation of 11-cyanoundecanoic acid.

Description

technical field [0001] The invention relates to a preparation method of 11-cyanoundecanoic acid, which belongs to the field of organic chemical industry. Background technique [0002] 11-cyanoundecanoic acid is an important chemical intermediate, which can be used to synthesize dodecanoic acid and 12-aminododecanoic acid, which are the raw materials for preparing nylon 1212, nylon 612 and nylon 12. [0003] The preparation of 11-cyanundecanoic acid from cyclohexanone requires two steps of reaction, the first step is the ammoxidation of cyclohexanone to prepare 1,1'-dicyclohexyl peroxide (PXA), which decomposes itself under high temperature conditions Generate 11-cyanoundecanoic acid (CUA) and other products, wherein the self-decomposition reaction of PXA is a key step in this process route. The whole reaction process is as follows: [0004] [0005] Patent GB1198422 reports the thermal decomposition reaction of PXA under 98-2940Pa negative pressure, the pyrolysis temper...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/00C07C255/19B01J23/10B01J27/10B01J27/08B01J27/053B01J27/25
CPCB01J27/053B01J27/08B01J27/10B01J27/25C07C253/00C07C255/19
Inventor 杜旺明陈海波张彦雨李俊平边新建赵文娟张颖宋静黎源
Owner WANHUA CHEM GRP CO LTD