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Synthesis method of spiro-compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane

A technology of spiro compound and dioxaspiro, applied in the field of synthesis of spiro compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane, Achieve the effect of simple and convenient synthesis method, solve the problem of poor mechanical properties and easy operation

Inactive Publication Date: 2013-10-23
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, the expansion monomers that have been found are also limited to compounds with structures such as Bicyclic Ortho Ester, Spiro Ortho Ester and Spiro Ortho Carbonate.

Method used

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  • Synthesis method of spiro-compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane
  • Synthesis method of spiro-compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane
  • Synthesis method of spiro-compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A spiro compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane, its molecular formula is C 9 h 8 o 6 , the structural formula is

[0037] The synthesis method of the spiro compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane, the specific steps are as follows:

[0038] (1) Preparation of 1,3-magnesium dibromide-2,2-bis(magnesium bromide methyl)propane

[0039] According to the molar ratio of 1:6, weigh 1,3-dibromo-2,2-bis(bromomethyl)propane and magnesium chips; 0.5wt% of the total mass of propane takes by weighing initiator, and initiator is the mixture of iodine and ethyl bromide, and the weight ratio of the two is 1:1; Measure solvent tetrahydrofuran according to 5 times of reactant volume, standby; All reactant All need to be dewatered, and the water content should be controlled below 500ppm;

[0040]In a dry four-necked flask with a nitrogen inlet, a condenser tube (the outlet is connected to a calcium chloride drying tube), a thermometer, and a ...

Embodiment 2

[0046] A kind of synthetic method of spiro compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane, the specific steps are as follows:

[0047] (1) Preparation of 1,3-magnesium dibromide-2,2-bis(magnesium bromide methyl)propane

[0048] Except that the molar ratio is 1:5, weigh 1,3-dibromo-2,2-bis(bromomethyl)propane and magnesium chips; ) 0.8wt% of the total mass of propane takes by weighing initiator, and initiator is the mixture of iodine and ethyl bromide; Measures solvent tetrahydrofuran according to 4 times of reactant volume, all the other carry out experiment identically with (1) among the embodiment 1;

[0049] Except that the microwave reaction time is 0.7h, the microwave reaction temperature is 45°C, and the microwave power is 800W, the experiment is the same as in Example 1 to obtain 1,3-dibromide-2,2-di(magnesium bromide base) propane.

[0050] (2) Preparation of 1,3-dicarboxy-2,2-di(acetoxy)propane

[0051] In the THF solution of above-mentioned gained 1,3...

Embodiment 3

[0055] A kind of synthetic method of spiro compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane, the specific steps are as follows:

[0056] (1) Preparation of 1,3-magnesium dibromide-2,2-bis(magnesium bromide methyl)propane

[0057] In addition to weighing 1,3-dibromo-2,2-bis(bromomethyl)propane and magnesium chips according to the molar ratio of 1:7; 1.0wt% of the total mass of propane takes by weighing the initiator, which is a mixture of iodine and ethyl bromide; except that the solvent tetrahydrofuran is measured according to 6 times of the volume of the reactant, all the others are carried out the same experiment as (1) in Example 1 ;

[0058] Except that the microwave reaction time is 0.6h, the microwave reaction temperature is 44°C, and the microwave power is 700W, the experiment is the same as in Example 1 to obtain 1,3-dibromide-2,2-bis(magnesium bromide base) propane.

[0059] (2) Preparation of 1,3-dicarboxy-2,2-di(acetoxy)propane

[0060] In the THF sol...

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Abstract

The invention relates to a synthesis method of a spiro-compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane. The synthetic route is 1,3-dibromo-2,2-di(bromomethyl)propane, 1,3-magnesium dibromide-2,2-di(magnesium bromide methyl)propane, 1,3-dicarboxyl-2,2-di(acetoxy)propane, and 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane. The 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane can be used as a novel expansion curing agent for an epoxy resin to reduce the volume shrinkage of the system to 0-1%, thereby overcoming the defect of poor mechanical properties of the epoxy resin cured by aliphatic acid anhydride, and improving the problem of volume shrinkage of the material. The invention is mainly used in the fields of epoxy resin casting and composite materials thereof.

Description

technical field [0001] The invention relates to a spiro compound 2,4,8,10-tetracarbonyl-3,9-dioxaspiro[5,5]undecane and a synthesis method thereof. Background technique [0002] Thermosetting epoxy resin will shrink in volume during the curing process (volume shrinkage rate of 2 to 5%), which is a fatal defect for epoxy resin and its composite materials, which will cause the strength of the material to decrease, and even lead to microcracks in the material Or defects such as cracking, dimensional instability or degumming of glued joints. In practical applications, the residual stress of epoxy resin potting materials used as stress-sensitive electronic components will cause the performance of electronic components to deteriorate and the parameters to drift. Residual stress can also make adhesive joints or resin and fiber interfaces vulnerable to environmental factors such as oxygen and water, thereby greatly reducing the service life of the material. Therefore, the research...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C08G59/42
Inventor 彭永利赖小莹罗灿万春杰熊丽君
Owner WUHAN INSTITUTE OF TECHNOLOGY
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