Sulfydryl functionalized organic aromatic carboxylic acid ligand and preparation method and application thereof

A technology of aromatic carboxylic acid and functionalization, which is applied in the fields of mercaptan preparation, thioether preparation, organic chemistry, etc., can solve the problem of insufficient mercapto group content, and achieve the effect of simple preparation method, good performance and less preparation steps

Inactive Publication Date: 2020-06-05
GUANGDONG UNIV OF TECH
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention provides a mercapto-functionalized organic aromatic carboxylic acid ligand and its preparation method and application, which solves the problem of insufficient thiol content in the mercapto-functionalized organic aromatic carboxylic acid ligand

Method used

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  • Sulfydryl functionalized organic aromatic carboxylic acid ligand and preparation method and application thereof
  • Sulfydryl functionalized organic aromatic carboxylic acid ligand and preparation method and application thereof
  • Sulfydryl functionalized organic aromatic carboxylic acid ligand and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0047] This example is the preparation of the precursor of sulfur-based functionalized organic aromatic carboxylic acid ligands

[0048] 1) in N 2 Under protection, the raw material methyl tetrafluoroterebenzoate M1 (2.7 g) was weighed and added into a 250 mL two-neck round bottom flask. Weigh benzyl mercaptan (27.2g) and potassium carbonate (50g) into a 250mL two-necked round bottom flask respectively. The round bottom flask was attached to the Schlenk line. Transfer 90 mL of degassed anhydrous N,N-dimethylformamide solution to a flask, and then stir the reaction at 25° C. for 48 h.

[0049] 3) Stirring was stopped, then the reaction mixture was poured into water (150 mL), the aqueous solution was extracted (3 x 80 mL) with ethyl acetate, and the ethyl acetate was combined. The extracted ethyl acetate was washed with water (3×100 mL), followed by anhydrous MgSO 4 The ethyl acetate was dried and then removed with a rotary evaporator. The crude product was obtained as a pa...

Embodiment 2

[0056] This example is the preparation of thiol-functionalized organic aromatic carboxylic acid ligands

[0057] 1) in N 2 Under protection, weigh 300mg of M2 and add it to a 50mL reaction bottle. Connect the reaction eggplant bottle to the gas line conduit, then evacuate it and fill it with N2, repeat three times, then freeze the reaction eggplant bottle with liquid nitrogen, slowly add 600mg of aluminum trichloride under the protection of nitrogen, and then raise the temperature to room temperature (25°C) , Stir the reaction for 12h.

[0058] 2) After stopping the reaction, ice-bath the reaction system, and under the protection of nitrogen, add ice cubes into the reaction eggplant bottle, a large amount of solids precipitate out, and vigorously stir for 30 minutes. Filter under reduced pressure, wash the filter residue with a large amount of water, wash the residual by-products, dry in the air, and vacuum-dry to obtain tetramercaptoterephthalic acid, which is recorded as M...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a sulfydryl functionalized organic aromatic carboxylic acid ligand and a preparation method and application thereof.The invention discloses a precursor of the sulfydryl functionalized organic aromatic carboxylic acid ligand, which has a structure as shown in a formula (I), contains rich benzyl mercaptan side chains and can be used for preparing the sulfydryl functionalized organic aromatic carboxylic acid ligand. Due to the fact that the ligand contains rich sulfydryl functional groups, the sulfydryl functionalized organic aromatic carboxylic acid ligand is applied to synthesis of MOF materials, and excellent performances can be provided for the MOF materials.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a mercapto-functionalized organic aromatic carboxylic acid ligand and its preparation method and application. Background technique [0002] In the past 30 years, metal-organic framework materials (MOF) have been developed rapidly. As the most diverse and flexible part of metal-organic framework materials, a large number of organic ligands have been synthesized by researchers, including elements such as nitrogen, carboxylic acid and phosphoric acid. or functional organic ligands, among which organic aromatic carboxylic acid ligands are the most widely used. Due to the rich valence of sulfur, it has been incorporated into organic aromatic carboxylic acid ligands by researchers, for example, there are already some mercapto-functionalized organic aromatic carboxylic acid ligands (structures shown below), And for the synthesis of thiol-functionalized MOF materials, these M...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/62C07C319/14C07C319/06C08G83/00
CPCC07C319/06C07C319/14C07C323/62C08G83/008
Inventor 何军胡洁颖钟苑辉何永和周华群冼万如
Owner GUANGDONG UNIV OF TECH
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