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Method for catalytic synthesis of disulfide compounds by using alkaline zeolite molecular sieve

A technology of thiol compounds and compounds, which is applied in the field of green organic fine catalytic synthesis, can solve the problems of increased processing costs, unfriendly environment, and difficult separation, and achieve the effect of simple synthesis method, low toxicity environment, and high tolerance

Pending Publication Date: 2022-03-22
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But during the reaction, harmful liquid waste will be produced, which contains a large amount of salt and nitrogen oxides, so the cost of disposal increases, and it is not friendly to the environment
Therefore, other catalysts using oxygen as the oxidizing agent are also correspondingly produced, such as the metal salt K 3 PO 4 (Tetrahedron Lett.2005,46,3583), CsF (Tetrahedron Lett.2003,44,6789), metal oxide CeO 2 (Chem.Sci.2012,3,398), transition metals (Green Chem.,2017,19,2491–2495), organic ligand catalysts (AsianJ.Org.Chem.,2017,6,265–268), enzymes (Green Chem. ,2013,15,1490–1495), etc., but when these catalysts are used to catalyze mercaptans for asymmetric coupling reactions, not only the yield is low, but also it is not easy to separate, and it is easy to affect the subsequent process

Method used

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  • Method for catalytic synthesis of disulfide compounds by using alkaline zeolite molecular sieve
  • Method for catalytic synthesis of disulfide compounds by using alkaline zeolite molecular sieve
  • Method for catalytic synthesis of disulfide compounds by using alkaline zeolite molecular sieve

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Weigh 30 mg of ETS-10 catalyst into the reaction tube, then add 0.2 mmol of benzyl mercaptan and 1 mL of cyclohexane. Under a nitrogen atmosphere, react in a heater at 120° C. for 5 h, and centrifuge after the end of the experiment. After rotary evaporation, the obtained liquid phase product was separated by flash column chromatography (the volume ratio of eluent petroleum ether and ethyl acetate was 10:1), and a yellow oily substance was obtained. The product yield can reach 95%, and the characterization data of the product are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.25–7.12 (m, 10H), 3.50 (s, 4H).

Embodiment 2

[0033]

[0034] Weigh 30 mg of ETS-10 catalyst into the reaction tube, then add 0.2 mmol of o-aminothiophenol and 1 mL of cyclohexane. Under a nitrogen atmosphere, react in a heater at 120° C. for 5 h, and centrifuge after the end of the experiment. The obtained solid-phase product was subjected to flash column chromatography (the volume ratio of eluent petroleum ether and ethyl acetate was 4:1) to separate the obtained solid phase product by rotary evaporation to obtain a yellow solid. The product yield can reach 90%, and the characterization data of the product are as follows: 1 H NMR (500MHz, Chloroform-d) δ7.09(ddd, J=7.6,6.1,1.8Hz,4H),6.66–6.62(m,2H),6.54–6.49(m,2H),4.26(s,4H ).

Embodiment 3

[0036]

[0037] Weigh 30 mg of ETS-10 catalyst into the reaction tube, then add 0.2 mmol of p-methylthiophenol and 1 mL of cyclohexane. Under a nitrogen atmosphere, react in a heater at 120° C. for 5 h, and centrifuge after the end of the experiment. The obtained solid-phase product was subjected to flash column chromatography (the volume ratio of eluent petroleum ether and ethyl acetate was 50:1) for separation by rotary evaporation to obtain a white solid. Product yield can reach 84%, and the characterization data of product are as follows: 1 H NMR (500MHz, Chloroform-d) δ 7.30 (d, J = 8.2Hz, 5H), 7.02 (d, J = 7.9Hz, 5H), 2.23 (s, 6H).

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Abstract

The invention discloses a method for catalytic synthesis of disulfide compounds by using an alkaline zeolite molecular sieve, and belongs to the field of green organic fine catalytic synthesis. According to the method for synthesizing the disulfide-containing compound by using a thiol compound as a substrate, aromatic thiol, aliphatic thiol and heterocyclic thiol are subjected to self-coupling reaction in a nitrogen atmosphere under the condition of no oxidant and metal through ETS-10 zeolite molecular sieve solid base catalysis and sulfur hydrogen bond activation. Finally, a series of disulfide compounds are obtained. The method is simple in step, high in product yield and easy to separate and purify.

Description

technical field [0001] The invention belongs to the field of green organic fine catalytic synthesis, and specifically relates to a method for synthesizing disulfide compounds by catalyzing mercaptan compounds with ETS-10 zeolite molecular sieves. Background technique [0002] As a valuable and abundant functional group in natural compounds, biological reagents and pharmaceuticals, sulfur-sulfur bond exhibits excellent biological activity and reactivity. Due to the biocompatibility of disulfide compounds, pharmaceutical researchers use them as important intermediates for the synthesis of new drugs, as well as precursors for drug delivery. Moreover, disulfide compounds play an important role in functional materials such as biomaterials, biochemical sensors, rechargeable batteries, and rubber vulcanization accelerators. [0003] The general synthesis methods of disulfide compounds include thiolysis method, reductive dimerization method of thiohydrogen salt, sulfur or polysulfi...

Claims

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Application Information

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IPC IPC(8): C07C319/24C07C321/10C07C323/33C07C323/20C07C323/09C07C321/22C07C323/52C07C323/07C07D333/34C07D213/71
CPCC07C319/24C07D333/34C07D213/71C07C321/10C07C323/33C07C323/20C07C323/09C07C321/22C07C323/52C07C323/07
Inventor 唐天地孟从玮朱超杰刘会丽傅雯倩
Owner CHANGZHOU UNIV
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