A kind of preparation method of isobornyl acrylate of biological origin

A technology of isobornyl acrylate and methacrylic acid, which is applied in the field of photocatalytic organic synthesis, and can solve problems such as uneven heating, low efficiency, and long reaction time

Active Publication Date: 2021-07-06
SOUTH CHINA AGRI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the currently developed method for synthesizing isobornyl (meth)acrylate, a strong acid catalyst is generally used to synthesize under heating conditions, and there are problems such as long reaction time, low efficiency, and uneven heating.

Method used

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  • A kind of preparation method of isobornyl acrylate of biological origin
  • A kind of preparation method of isobornyl acrylate of biological origin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 136g camphene (1.0mol) in 129g methacrylic acid (1.5mol), dissolve, stir well, add 26.5g (10%) phosphotungstic acid / silica gel catalyst (HPW / SiO 2 ) and 0.129g (0.1%) inhibitor hydroquinone, stir evenly, place light under a 100W UV light source, react while stirring at a speed of 100r / min, stop after reacting for 10min, and obtain The pure and transparent isobornyl methacrylate has a measured yield of 91.2%.

[0031] The molecular weight of the synthesized product was measured with an Agilent 7250GC / Q-TOF GC / MS system from Agilent Corporation of the United States, and the relative molecular mass of the product was measured to be 222, which was the same as the theoretical relative molecular mass of isobornyl methacrylate.

[0032] Test sample with American Nicolet company Thermo-Nicolet iS10 type Fourier transform infrared spectrometer, the infrared spectrum of the synthesized isobornyl methacrylate is as follows: figure 1 shown. 2880~2966cm -1 C-H stretching vibr...

Embodiment 2

[0034] Add 136g camphene (1.0mol) in 72g acrylic acid (1.0mol), dissolve, stir well, add 2.22g (1%) catalyst cationic photoinitiator triarylsulfonium salt (UVI 6976 of Dow Chemical Company) and 0.172 g (0.2%) polymerization inhibitor p-hydroxyanisole, stir evenly, place it under a 200W UV light source, react while stirring at a speed of 200r / min, stop after 20min, and obtain pure and transparent by rotary evaporation under reduced pressure The isobornyl acrylate is recorded as 92.4% in yield.

[0035] The molecular weight of the synthesized product was measured with an Agilent 7250GC / Q-TOF GC / MS system from Agilent Corporation of the United States, and the relative molecular mass of the product was measured to be 208, which was the same as the theoretical relative molecular mass of isobornyl acrylate.

[0036] The sample was tested with a Thermo-Nicolet iS10 Fourier transform infrared spectrometer from Nicolet Company of the United States, and the characteristic peaks on the t...

Embodiment 3

[0038]Add 136g camphene (1.0mol) in 43g methacrylic acid (0.5mol), dissolve, stir well, add 8.95g (5%) catalyst acidic ionic liquid N-(4-sulfonic acid group) butyl trimethylamine hydrogen sulfate Salt and 0.129g (0.3%) inhibitor phenothiazine, stir evenly, place light under the UV light source of 300W, react while stirring with the rotating speed of 300r / min, stop after reacting for 30min, decompression rotary evaporation promptly obtains pure The yield of transparent isobornyl methacrylate was measured to be 90.8%.

[0039] The molecular weight of the synthesized product was measured with an Agilent 7250GC / Q-TOF GC / MS system from Agilent Corporation of the United States, and the relative molecular mass of the product was measured to be 222, which was the same as the theoretical relative molecular mass of isobornyl methacrylate.

[0040] The sample was tested with a Thermo-Nicolet iS10 Fourier transform infrared spectrometer from Nicolet Company of the United States, and the c...

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Abstract

The invention belongs to the technical field of photocatalytic organic synthesis, and discloses a preparation method of isobornyl (meth)acrylate from biological sources. The method comprises the following steps: adding camphene, (meth)acrylic acid, a polymerization inhibitor and a catalyst into a transparent reactor, mixing them uniformly, placing them under the irradiation of UV light, stirring and reacting, and carrying out rotary evaporation under reduced pressure after the reaction is finished, namely Isobornyl acrylate and isobornyl methacrylate are obtained. The present invention adopts the photocatalytic method to prepare isobornyl (meth)acrylate, the reaction conditions are mild, the reaction time is short, there is no side reaction and by-product, no high temperature and high pressure and other conditions are required, the separation and purification are simple and easy to operate, and (methyl)acrylate can be obtained. Isobornyl Acrylate. The invention adopts the natural renewable resource camphene to prepare isobornyl (meth)acrylate, opens up a new application direction for the natural renewable resource vegetable oil, improves its economic value, and has a good popularization effect on the development of agriculture and forestry economy.

Description

technical field [0001] The invention belongs to the technical field of photocatalytic organic synthesis, and in particular relates to a preparation method of biologically derived isobornyl (meth)acrylate. Background technique [0002] Isobornyl (meth)acrylate is an important acrylate monomer, which has a unique bridging ring structure, so it has low viscosity, high boiling point, low surface tension, low shrinkage, high glass transition temperature, low color High degree, high refractive index, good hydrophobicity, good compatibility with various resins, solvents, pigments and fillers, and special physical and chemical properties such as low toxicity and non-flammability. At present, isobornyl (meth)acrylate is mainly used as a reactive diluent in radiation-cured coatings, inks and adhesives. Its special feature is that while increasing the hardness of the film-forming material, it can also maintain and increase its elasticity, and It can improve the gloss, vividness, adhes...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/04C07C67/62C07C69/54
CPCC07C67/04C07C67/62C07C2602/42C07C69/54
Inventor 袁腾刘影灵肖亚亮李小平杨卓鸿
Owner SOUTH CHINA AGRI UNIV
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