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Preparation method for co-production of cyclododecene ether and cyclododecanol

A technology of cyclododecene ether and cyclododecanol is applied in the preparation field of co-production of cyclododecene ether and cyclododecanol, and can solve the problem of increased input cost of basic substances, high peroxide concentration, and oxidizing agent. High cost problem, to achieve the effect of improving technological innovation and process competitiveness, less by-products, and low cost

Pending Publication Date: 2022-03-01
CHINA TIANCHEN ENG +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The industrialization of this process is also limited, and the large amount of waste solids, waste liquid and wastewater produced by neutralization is the key obstacle; at the same time, the input cost of alkaline substances in the neutralization process will inevitably increase the cost, and the lack of economy is also an important limiting factor
[0005] The currently disclosed cyclododecenyl ether and cyclododecanol production processes have the following disadvantages: first, storage risks, epoxy products are mainly realized by hydrogen peroxide and alkyl hydroperoxide, in order to improve the conversion rate and The feed rate of a single reactor requires high-concentration peroxide raw materials in the system, and the storage risk of hydrogen peroxide or alkyl hydrogen peroxide is high; second, there are many side reactions, the concentration of peroxide in the reaction system is high, and disorderly triggers Side reactions; third, in order to increase the reaction rate, the temperature of the reaction system is at 100-150°C, and the high-temperature process is accompanied by the decomposition of hydrogen peroxide and alkyl hydroperoxide, and the cost of the oxidant is relatively high

Method used

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  • Preparation method for co-production of cyclododecene ether and cyclododecanol
  • Preparation method for co-production of cyclododecene ether and cyclododecanol
  • Preparation method for co-production of cyclododecene ether and cyclododecanol

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Embodiment 1

[0032] This embodiment combines figure 1 and figure 2 A preparation method for the co-production of cyclododecenyl ether and cyclododecanol in the present invention is described.

[0033] Add 500 grams of cyclododecene into a 2L autoclave. Add 1.0 g of tert-butyl hydroperoxide initiator; feed air at a flow rate of 1.0 L / min. The reaction temperature is 110°C, the pressure is 0.8MPa, and the residence time is 4h.

[0034] Add 0.1 g of molybdenum acetylacetonate to the mixed solution. The reaction temperature is 150° C., the pressure is 0.3 MPa, and the reaction time is 45 minutes.

[0035] After removing unreacted raw materials and catalysts from the above mixed solution, 129.5 grams of the mixed solution was added to a 500 mL autoclave. Add 10% Ni-SiO to the mixture 2 Catalyst 0.3 g. The reaction temperature is 120° C., the hydrogen pressure is 6 MPa, and the reaction time is 3 h. The finished product is 125.6 grams in total, the ratio of cyclododecenyl ether to cyclo...

Embodiment 2

[0037]Add 500 grams of cyclododecatriene into a 2L autoclave. Add 0.5 g of tert-butyl hydroperoxide initiator; feed air at a flow rate of 2.0 L / min. The reaction temperature is 105° C., the pressure is 1.0 MPa, and the residence time is 3 h.

[0038] Add 1.5 grams of molybdenum naphthenate ketone in the mixed solution. The reaction temperature is 130° C., the pressure is 0.4 MPa, and the reaction time is 35 minutes.

[0039] After removing unreacted raw materials and catalysts from the above mixed solution, 144.6 grams of the mixed solution was added to a 500 mL autoclave. Add 40% Ni-SiO to the mixture 2 Catalyst 0.5 g. The reaction temperature is 110° C., the hydrogen pressure is 7 MPa, and the reaction time is 1 h. The finished product is 132.5 grams in total, the ratio of cyclododecenyl ether to cyclododecanol is 46.2:53.8, and the total yield is 91.6%.

Embodiment 3

[0041] Add 300 grams of cyclododecene into a 1L autoclave. Add 0.35 g of isopropyl hydroperoxide (85%) initiator; feed oxygen and nitrogen mixed gas (volume ratio 3.5:1), flow rate is 2.8 L / min. The reaction temperature is 115°C, the pressure is 1.4MPa, and the residence time is 4h.

[0042] Add 2.5 grams of molybdenum nitrate in the mixed solution. The reaction temperature is 115° C., the pressure is 0.35 MPa, and the reaction time is 25 minutes.

[0043] After removing the raw material and the catalyst from the above mixed solution, 34.5 grams of the mixed solution was added into a 100 mL autoclave. Add 0.2 g of 60% Ni-alumina catalyst to the mixed solution. The reaction temperature is 110° C., the hydrogen pressure is 8 MPa, and the reaction time is 2.0 h. The finished product is 32.09 grams in total, the ratio of cyclododecenyl ether to cyclododecanol is 57.8:42.2, and the total yield is 91.6%.

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Abstract

The invention provides a preparation method for co-producing cyclododecene ether and cyclododecanol, which comprises three continuous processes of oxidation, epoxidation and hydrogenation which are connected in series: in the oxidation process, any one or a mixture of cyclododecene, cyclododecadiene and cyclododecatriene is taken as a raw material, an initiator is added, and mixed gas of nitrogen and oxidizing gas is introduced; an epoxidation process: directly adding an epoxy catalyst into a product obtained by the oxidation process to prepare an epoxy structure product; a hydrogenation process: rectifying and separating out unreacted raw materials and an epoxy catalyst in the epoxidation process, and adding a hydrogenation catalyst into the residual solution to prepare cyclododecene ether and cyclododecanol; the preparation method disclosed by the invention is low in cost and green and environment-friendly, byproducts in the whole reaction process are few, and the product yield is increased.

Description

technical field [0001] The invention belongs to the field of fine chemicals and flavors and fragrances, and in particular relates to a preparation method for the coproduction of cyclododecenyl ether and cyclododecanol. Background technique [0002] Cyclododecenyl ether, liquid, has a strong camphor and musk aroma, and has a patchouli-like fragrance, and is a mixture of cis and trans isomers. Hertz Company of Germany produces cyclododecenyl ether, and its product specification is a mixture with a content >99% (Technical Handbook of Synthetic Fragrances, edited by Liu Shuwen, second edition). [0003] Cyclododecanol can be used to prepare plastics, dicarboxylic acids, synthetic lubricants, plasticizers, intermediates, etc. in industry, and it is also a fine chemical raw material. Cyclododecanol is oxidized with nitric acid to obtain dodecane dibasic acid. It is an important long-chain dibasic acid. It is mainly used in the industry to produce nylon PA612, PA1212, PAPACM12 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D301/19C07D303/04C07C29/17C07C29/132C07C35/205
CPCC07D301/19C07D303/04C07C29/172C07C29/132C07C407/00C07C2601/20C07C35/205C07C409/14
Inventor 冯传密王聪刘新伟杨克俭李荣吴昊史文涛黄冠博靳权黄贺源龙滢李广忠
Owner CHINA TIANCHEN ENG
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