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Polyacetylenic compound and preparation method thereof

A technology of compound and polyalkyne amine, which is applied in the field of polyalkyne amine compounds and the preparation of the polyalkyne amine compounds by reacting alkyne halides and sulfonamides, achieving the effects of good application value, simple preparation method and mild reaction conditions

Active Publication Date: 2017-05-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the coupling polymerization reaction of acetylenic amines has not been studied and reported in the organic field, so it can be predicted that the development of simple and efficient synthesis routes of polyalkynyl amines will have important scientific significance and application value

Method used

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  • Polyacetylenic compound and preparation method thereof
  • Polyacetylenic compound and preparation method thereof
  • Polyacetylenic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of polyalkyne amine compound P1, its structural formula is as follows:

[0037]

[0038] The polyalkyne amine compound is prepared by reacting an alkyne halide with a sulfonamide monomer, and its specific reaction equation is as formula (1):

[0039]

[0040] (1) The synthesis method of monomer M1 is: at 0°C, add 9.0mmol (3.29g) of sulfonyl chloride into a 250mL two-necked bottle, vacuumize and replace N 2 After adding 150mL of dichloromethane and 36.9mmol (4.03mL) benzylamine, the reaction system was stirred at room temperature for 2 hours, extracted three times with dichloromethane and water, spin-dried, and the crude product was separated and purified by silica gel chromatography Vacuum drying at 40°C gave 7.7 mmol (3.90 g) of product (monomer M1) with a yield of 85%; figure 1 8.20 of the M1 monomer in the NMR diagram is -NH peak, and 4.04 is -CH 2 Peak, wherein, 3.32 is water peak, and 2.50 is DMSO-d6 peak; image 3 There is a -NH peak in monomer M1;...

Embodiment 2

[0048] In this example, the reaction time in Example 1 was changed to 80° C., and other preparation conditions were the same as in Example 1 to obtain 0.13 g of polymer with a yield of 90% and a molecular weight of 17000 g / mol.

Embodiment 3

[0050] In this embodiment, the CuSO in embodiment 1 4 ·5H 2 O feed intake is changed into 0.04mmol (0.007g), 1,10-phenanthroline feed intake is changed into 0.08mmol (0.02g), K 2 CO 3 The feeding amount was changed to 0.80 mmol (0.11 g), and the other preparation conditions were the same as in Example 1 to obtain 0.12 g of polymer with a yield of 81% and a molecular weight of 18000 g / mol.

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Abstract

The invention belongs to the technical field of organic chemistry, and discloses a polyacetylenic compound and a preparation method thereof. The method comprises the following steps: (1) under the protection of an inert gas, mixing a diacetylene halide compound and a binary sulphonamide compound in a catalytic system and an organic solvent, reacting, and cooling to obtain a reaction mother liquid; (2) adding the reaction mother liquid into a precipitator for precipitating, collecting a precipitated, and drying to constant weight to obtain a polyacetylenic compound. The preparation method disclosed by the invention is simple; the reaction is efficient; the group tolerance is high; a plurality of functional groups can be intruded into monomers; the prepared polyacetylenic compound contains a carbon-carbon triple bond, and has important application to serving as an intermediate in a further reaction; moreover, the compound is easy to hydrolyze, and has a very promising prospect in the aspects of environmentally friendly chemistry, green chemistry and the like, such as a degradable material.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and relates to the synthesis of polyalkyne amine compounds, in particular to a polyalkyne amine compound and a method for preparing the polyalkyne amine compound by reacting an alkyne halide and a sulfonamide. Background technique [0002] The development of new polymerization reactions is of great importance to polymer materials science. Alkynes are one of the chemical raw materials that are easy to obtain or synthesize. The use of alkynes to construct functional polymers has important academic and technical significance, and has attracted widespread attention from scientists. The coupling polymerization of alkyne amines has the characteristics of mild reaction conditions, high reaction efficiency, and atom economy. It meets the definition of green chemical reactions and is a new type of polymerization reaction. At present, small molecules based on alkyne amines have been widely report...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02C08G73/00
CPCC08G73/00C08G73/0253
Inventor 唐本忠伍秀英胡蓉蓉秦安军赵祖金
Owner SOUTH CHINA UNIV OF TECH
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