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A kind of synthetic method of allyl acrylate

A technology of allyl acrylate and a synthesis method, applied in the field of light curing, to achieve the effects of easy purification and easy distillation under reduced pressure

Inactive Publication Date: 2018-11-09
YANTAI DARBOND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] (3) The presence of organochlorine will have a negative impact on organic silicon, which is especially fatal in the field of electronic materials.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1.1 Synthesis of acryloyloxytrimethylsilane:

[0033] Add 216 g of acrylic acid, 326 g of trimethylchlorosilane, and 5.2 g of p-hydroxyanisole (MEHQ) into a 1L three-necked flask equipped with a constant pressure funnel, a magnetic stirring bar, a thermometer, a distillation device, and an acid gas absorption bottle, and heat up to 70°C, stirred and refluxed for 4 hours under nitrogen protection, stopped heating, cooled the system to room temperature, added 5.8g of sodium acrylate and stirred for half an hour, then filtered. The filtrate was distilled under reduced pressure to obtain 380g colorless and transparent acryloxytrimethylsilane, with a yield of 87.9%.

[0034] The reaction is shown in formula (6)

[0035] (6)

[0036] 1.2 Synthesis of Diphenyl Diallyloxysilane:

[0037] Add 506 g diphenyldichlorosilane, 232 g allyl alcohol, 6 g MEHQ, 250 g n-hexane to the 2L three-necked flask equipped with a constant pressure funnel, a magnetic stirring bar, a thermomet...

Embodiment 2

[0043] 2.1 Synthesis of phenyltriallyloxysilane

[0044]Add 422g phenyltrichlorosilane, 174g allyl alcohol, 10g MEHQ, 300g n-hexane to a 2L three-necked flask equipped with a constant pressure funnel, a magnetic stirring bar, a thermometer, a distillation device, and an acid gas absorption bottle, and heat up to 70 ℃, stirred and refluxed for 4 hours to remove hydrogen chloride, added 9g of sodium allyl alkoxide, and stirred for half an hour, the system was weakly alkaline as measured by pH test paper, filtered to remove salt, and distilled off n-hexane under reduced pressure to obtain 502 g of The yellow liquid is phenyltriallyloxysilane, and the yield is 90.9%. The reaction is shown in formula (9)

[0045] (9)

[0046] 2.2 Synthesis of allyl acrylate

[0047] Add 303 g (2.1 mole) of acryloyloxytrimethylsilane and 210 g (0.76 mole) of triallyloxyphenylsilane into a 1L three-necked flask equipped with a constant pressure funnel, a magnetic stirring bar, a thermometer, and...

Embodiment 3

[0050] 3.1 Synthesis of methylphenyl diallyloxysilane:

[0051] Add 382g of methylphenyldichlorosilane and 116g of allyl alcohol into the reaction flask, add 2.5g of p-hydroxyanisole MEHQ, and 250g of n-hexane, heat up to 70°C, stir and reflux for 3 hours to remove hydrogen chloride, Add 5g of sodium allyl alcohol, stir for half an hour, use pH test paper to determine that the system is weakly alkaline, filter to remove salt, and distill off n-hexane under reduced pressure to obtain 404g of light yellow liquid, which is methyl phenyl diallyl oxide Silane. Yield is 86.3%. The reaction is shown in formula (11).

[0052] (11)

[0053] 3.2 Synthesis of allyl acrylate

[0054] Add 289 g (2.0 mole) acryloyloxytrimethylsilane, 246 g (1.05 mole) methylphenyldiallyloxy to a 1L three-necked flask equipped with a constant pressure funnel, magnetic stirring bar, thermometer, and distillation device Silane, 5.9 gMEHQ, 0.55g ammonium trifluoromethanesulfonate, stirred and reacted at ...

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Abstract

The invention discloses a new synthetic method of allyl acrylate. According to the method, an organic silicon monomer with functional groups is used, and the allyl acrylate is prepared under the soft reaction condition. The synthetic method of the allyl acrylate includes three steps that (1) acryloxytrimethylsilane is synthesized; (2) allyloxy silane is synthesized; and (3) the acryloxytrimethylsilane and the allyloxy silane are mixed. According to the raw materials used in a reaction, chlorine elements are fully converted into inorganic salt, low-boiling-point chloride like phosphorus trichloride is not used, and it is guaranteed that the chlorine elements are not contained in a prepared product; reaction conditions are soft, and the requirement for the equipment is not high; purification is easy, boiling points of all components are large in difference, and reduced pressure distillation separation is easy; water washing is not needed, and amplification is easy; and trifluoromethanesulfonic acid serves as a catalyst, the high acidity is achieved, and double bonds cannot be damaged.

Description

technical field [0001] The invention relates to a method for synthesizing monomeric substances in the field of photocuring, in particular to a method for synthesizing a special acrylate—allyl acrylate. Background technique [0002] Acrylates generally refer to ester compounds formed by the dehydration condensation of acrylic acid and alcohols (see Equation 1). This type of compound has acryloyloxy groups, so it can be used as a photocuring active monomer and is widely used in the field of photocuring. [0003] (1) [0004] The reaction is catalyzed by a strong acid. Higher alcohols react with acrylic acid in organic solvents, such as benzene, toluene, cyclohexane, n-heptane, etc., and water and organic solvents can form azeotropes to continuously remove water from the system. Excluded, so that the reaction continues to the right, the advantage is that the raw materials are easy to get, the device is simple, and can be easily scaled up, the disadvantage is that the use of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/02C07C69/54
CPCC07C67/02C07F7/1804C07F7/188C07F7/1896C07C69/54
Inventor 张京科陈维
Owner YANTAI DARBOND TECH
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