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Method for synthesizing disulfide compounds with s-s bonds by catalyzing molecular oxygen oxidation with phenylphenolic acid in aqueous phase
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A technology of disulfide compound and phenylphenolic acid, which is applied in the field of organic sulfur-sulfur bond synthesis, can solve the problems of increasing the difficulty and steps of post-treatment purification, difficult to avoid salt-containing wastewater, etc., and achieves strong industrial application prospects and environmental friendliness. , the effect of simple synthesis process
Active Publication Date: 2020-07-03
ZHENGZHOU UNIV
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[0006] The above self-coupling reactions and cross-coupling reactions oxidized with molecular oxygen (oxygen or air) are either carried out in organic solvents or use heterogeneous catalysts, which increase the difficulty and steps of product post-treatment purification, and it is difficult to avoid containing Production of saline wastewater, thus limiting the use of these methods
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Embodiment 1
[0033] Synthesis of disulfide compounds containing sulfur-sulfur bonds in an oxygen atmosphere:
[0034] In a 100mL reactor, put 3g of p-aminothiophenol, 4.5mg of gentisic acid, 6mg of cobalt sulfate, 8mg of manganese sulfate, 8mg of cobalt chloride, 0.5g of KOH and 45mL of water; Enter oxygen, keep the pressure in the reactor at 0.2MPa, stop the reaction after 12 hours of reaction, cool, filter, wash the filter cake with 10mL water, dry to obtain 2.88g of yellow solid, and the product is determined by methods such as NMR (see accompanying drawing), MS, etc. The structure is di-p-aminophenyl disulfide, the yield is 96%, and the purity of the product analyzed by liquid chromatography is 98%.
Embodiment 2
[0036] Synthesis of disulfide compounds containing sulfur-sulfur bonds in air:
[0037] In a 100mL reactor, add 5g 2-mercaptopyridine, 50mg salicylic acid, 50mg 2,4,6-trihydroxybenzoic acid, 75mg copper carbonate, 45mg iron acetate, 1g NaOH and 60mL water; heat up to 70°C, press air in, keep the pressure in the reactor at 0.1MPa, stop the reaction after 8 hours of reaction, cool, filter, wash with 10mL of water, and dry to obtain 4.9g of di-(2-pyridine) disulfide. The yield is 98%, and the purity of the product analyzed by liquid chromatography is 100%.
Embodiment 3
[0039] Synthesis of disulfide compounds containing sulfur-sulfur bonds in an oxygen-enriched air atmosphere:
[0040] In a 100mL reactor, put 10g p-nitrothiophenol, 10mg 2,3,4-trihydroxybenzoic acid, 20mg 5-dihydroxy-3,6-dioxo-1,4-cyclohexadiene -1-carboxylic acid, 10mg 2,4-dihydroxybenzoic acid, 10mg manganese carbonate, 2.3gK 2 CO 3and 20mL of water; heat up to 80°C under stirring, press in oxygen-enriched air [oxygen:air (wt:wt)=2:1], keep the pressure in the reactor at 0.4MPa, stop the reaction after 18 hours of reaction, cool, Filter, wash with water, and dry to obtain 9.6 g of di-p-aminophenyl disulfide with a yield of 96%. The purity of the product analyzed by liquid chromatography is 98%.
[0041] The organic compound containing sulfur-sulfur bond was synthesized by the same method as in Example 1, and its various reaction conditions and reaction results are shown in Table 1.
[0042] Table 1 Synthesis of various organic compounds containing sulfur-sulfur bonds unde...
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Abstract
The invention provides a method for synthesizing a disulfide compound having an S-S bond by catalysis of oxidation of molecular oxygen by phenylphenolic acid in an aqueous phase. In oxygen, phenylphenolic acid is used as a catalyst, the metal salt is used as a cocatalyst, so that a mercapto compound is reacted in the aqueous phase at a pressure of 0.01 to 1.00 MPa, a temperature of 40 to 120 DEG C, and a base equivalent of 0.1 to 20 for 1 to 30 hours, and the disulfide compound having the S-S bond is prepared. The method is applicable to synthesis of symmetrical disulfide compounds and asymmetric disulfide compounds. The reaction is carried out in an aqueous phase, and oxygen is used as a single oxidant; the catalyst has high catalytic activity, mild reaction condition and high efficiency;the synthesis process is simple, the product selectivity is high, the by-products are few, the product after the reaction is easy to be separated, the post-treatment is simple, the waste is small, the environmental protection is realized, and the method has strong industrial application prospect.
Description
technical field [0001] The invention relates to the technical field of organic sulfur-sulfur bond synthesis, in particular to a method for catalyzing molecular oxygen oxidation with phenylphenolic acid in water phase to generate disulfide compounds with S-S bonds. Background technique [0002] Organic S-S bond is an important structural unit in natural products, drugs and biomacromolecules, and its unique structural properties have always attracted much attention in organic synthesis. Disulfide compounds containing S-S bonds are important fine chemical intermediates and are widely used in natural products, organic synthesis, medicine, nanomaterials and chemical industries [Bablee Mandal, Basudeb Basu, RSC Adv., 2014, 4, 13854-13881]. The most commonly used method for constructing S-S bonds is the oxidative coupling of mercapto compounds [Dariusz Witt, Synthesis.2008, (16), 2491–2509]. Commonly used oxidants for oxidative coupling reactions include: halogens (such as iodine)...
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