Alkylthiol functionalized aromatic carboxylic acid compound and preparation method thereof

A technology of aromatic carboxylic acid and alkyl thiol, which is applied in the field of alkyl thiol-functionalized aromatic carboxylic acid compounds and their preparation, and can solve the problems of difficult modification of compounds, limitation of wide application and the like

Active Publication Date: 2017-11-10
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, the compound is difficult t

Method used

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  • Alkylthiol functionalized aromatic carboxylic acid compound and preparation method thereof
  • Alkylthiol functionalized aromatic carboxylic acid compound and preparation method thereof
  • Alkylthiol functionalized aromatic carboxylic acid compound and preparation method thereof

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[0028] The present invention provides a preparation method of the alkyl mercaptan functionalized aromatic carboxylic acid compound described in the above technical scheme, which comprises the following steps:

[0029] Mix 2-methyl methyl terephthalate, N-bromosuccinimide and benzoyl peroxide, under nitrogen and CCl 4 Reflux reaction in the presence of, and separate the reaction product to obtain 2-bromomethyl methyl terephthalate;

[0030] The 2-bromomethyl methyl terephthalate, sodium hydrosulfide and anhydrous methanol are mixed and reacted, and acidified to obtain an alkyl mercaptan functionalized aromatic carboxylic acid compound.

[0031] The synthetic route of the above preparation method is shown in Reaction Route 1:

[0032] Reaction route 1;

[0033] The present invention mixes 2-methyl methyl terephthalate, N-bromosuccinimide (NBS) and benzoyl peroxide (BPO), and mixes them in nitrogen and CCl 4 The reaction was refluxed in the presence of, and the reaction product was separa...

Embodiment 1

[0049] 1. Synthesis steps of 2-methyl methyl terephthalate (Intermediate 1):

[0050] (1) Weigh the raw material 2-methylterephthalic acid (1801.6mg, 10mmol) into a 100mL dry single-necked round bottom flask and add a magnetic stir bar;

[0051] (2) Measure 20 mL of anhydrous methanol with a graduated cylinder and add it to a single-necked round bottom flask;

[0052] (3) Stir at room temperature and slowly add concentrated sulfuric acid (0.5 mL) dropwise, and then reflux in an oil bath for 48 hours. After the reaction is completed, it is cooled to room temperature, a large amount of distilled water is added to the mixture, a large amount of solid is precipitated, and vacuum filtration is carried out to obtain 1873 mg of a white solid product (ie intermediate 1) with a yield of 90% and a purity of 99%.

[0053] 2. Synthesis steps of 2-bromomethyl methyl terephthalate (Intermediate 2):

[0054] (1) Weigh the first intermediate (1666mg, 8mmol) prepared above, N-bromosuccinimide (1780mg, ...

Embodiment 2

[0073] 1. Synthesis of 2-methyl methyl terephthalate

[0074] Weigh 1g 2-methylterephthalic acid, add 9mL methanol, and add 40 drops of concentrated H dropwise 2 SO 4 (2mol / L) as a catalyst, reflux in an oil bath at 60~75℃ for 24h. Add a large amount of deionized water to precipitate a white solid, dissolve the filtered white solid in ethyl acetate, and add anhydrous MgSO 4 Water was removed, the liquid was filtered off with suction, and the ethyl acetate was removed in vacuo to obtain white solid methyl 2-methyl terephthalate.

[0075] 2. Synthesis of 2-bromomethyl methyl terephthalate

[0076] Weigh 300mg of 2-methyl methyl terephthalate (1.46mmol), add 277.5mg (1.533mmol, 1.05~1.2 times molar amount) of NBS, 0.09~0.11 times molar amount of BPO, 8mLCCl in anhydrous and oxygen-free operation 4 Solvent, reflux in oil bath at 75~85℃ for 6~8h. The insoluble solid was washed with ether, and the filtrate was vacuumed to remove the solvent to obtain 2-bromomethyl methyl terephthalate as ...

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Abstract

The invention provides an alkylthiol functionalized aromatic carboxylic acid compound as well as a preparation method and application thereof. The compound has the structure as shown in formula I in the description. In the compound with the structure as shown in formula I, a mercapto group is separated from a benzene ring by a methylene group, the mercapto group is released, so that the mercapto group can better exert the functionalization effect and is easy to modify, and reactivity is higher; heavy metal ions can be adsorbed; flexibility of the side-chain benzyl mercaptan can be increased. Experimental results show that the compound can adsorb Hg<2+>.

Description

Technical field [0001] The invention relates to the technical field of compound synthesis, in particular to an alkyl mercaptan functionalized aromatic carboxylic acid compound and a preparation method thereof. Background technique [0002] Metal-Organic framework (MOF) has been rapidly developed as an emerging porous framework material. This type of porous material can directionally self-assemble metal-organic materials with preset structures and functions through the design of functional ligands. Frame material. MOF has some exploration in drug carrier. The uio-66 series in MOF has been proved to have very good biocompatibility and biodegradability, and it is suitable for drug carrier. Based on previous research findings, mercapto aromatic carboxylic acid compounds incorporate soft and hard atoms into one (soft and hard acid-base theory), in which the O on the carboxyl group is used as the hard base, and the S on the mercapto group is used as the soft base. Significantly. Whe...

Claims

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Application Information

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IPC IPC(8): C07C323/56C07C67/307C07C69/82C07C319/02C07C319/12B01J20/20
CPCB01J20/20C07C67/307C07C319/02C07C319/12C07C323/56C07C69/82
Inventor 胡湘子何军黄一涛张华堂何永和
Owner GUANGDONG UNIV OF TECH
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