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 compound and its preparation, which can solve the problems of difficult compound modification and limited wide application

Active Publication Date: 2019-04-12
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the compound is difficult to modify, which limits its wide application

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 kind of preparation method of alkylthiol functionalized aromatic carboxylic acid compound described in the above technical scheme, comprising the following steps:

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

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

[0031] The synthetic route of above-mentioned preparation method sees reaction scheme 1:

[0032] Reaction Scheme 1;

[0033] The present invention mixes 2-methyl terephthalate methyl ester, N-bromosuccinimide (NBS) and benzoyl peroxide (BPO), under nitrogen and CCl 4 In the presence of reflux reaction, the reaction product was separated...

Embodiment 1

[0049] One, the synthetic steps of 2-methyl terephthalate (intermediate 1):

[0050] (1) Weigh the raw material 2-methyl terephthalic 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 (0.5mL) dropwise, then place in an oil bath to reflux for 48h. After the reaction was complete, it was cooled to room temperature, and a large amount of distilled water was added to the mixture. A large amount of solids were precipitated, and filtered under reduced pressure to obtain 1873 mg of a white solid product (i.e. Intermediate 1), with a yield of 90% and a purity of 99%.

[0053] Two, the synthetic steps of 2-bromomethyl methyl terephthalate (intermediate 2):

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

Embodiment 2

[0073] One, the synthesis of methyl 2-methyl terephthalate

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

[0075] Two, the synthesis of methyl 2-bromomethyl terephthalate

[0076] Weigh 300mg of methyl 2-methyl terephthalate (1.46mmol), add 277.5mg (1.533mmol, 1.05-1.2 times the molar amount) of NBS, 0.09-0.11 times the molar amount of BPO, 8mLCCl in anhydrous and oxygen-free operation 4 Solvent, reflux in an oil bath at 75-85°C for 6-8 hours. The insoluble solid was washed with ether and the filtrate was stripped of the solvent in vacuo to give...

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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 alkylthiol functionalized aromatic carboxylic acid compound and a preparation method thereof. Background technique [0002] Metal-organic frameworks (Metal-Organic framework, MOF) have been rapidly developed as emerging porous framework materials. This kind of porous materials can be designed with functional ligands, and then directional self-assemble into metal-organic materials with preset structures and functions. frame material. MOFs have been explored in drug carriers. The uio-66 series of MOFs have been proven to have very good biocompatibility and biodegradability, and are suitable for drug carriers. Based on previous studies, it was found that mercapto aromatic carboxylic acid compounds combined soft and hard atoms into one (hard and soft acid-base theory), in which O on the carboxyl group is used as a hard base, and S on the mercapto group is used as a sof...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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