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2,2'-Dithiobis(benzothiazole) is a chemical substance with the molecular formula of C14H8N2S4 and CAS 120-78-5, which precipitates light yellow needle-like crystals from benzene. It is insoluble in water, ethyl acetate, gasoline and lye. The solubility (g/100ml) of the following substances at 25 ℃ is: ethanol<0.2, acetone<0.5, benzene<0.5, carbon tetrachloride<0.2, and ether<0.2. Slightly bitter, odorless. Slightly soluble in benzene, toluene, carbon tetrachloride, dichloromethane, acetone, ethanol, ether, etc. at room temperature, with low toxicity. It can burn in case of open fire. Danger of explosion in dust. As a general accelerator for natural rubber, synthetic rubber and reclaimed rubber, it is mainly used for manufacturing tyres, inner tubes, rubber tapes, rubber shoes and general industrial products. High purity DM (medical grade) is an important pharmaceutical intermediate for manufacturing cephalosporin anti-inflammatory drugs.
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Chemical Formula |
C14H8N2S4 |
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Exact Mass |
332 |
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Molecular Weight |
332 |
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m/z |
332 (100.0%), 334 (18.1%), 333 (15.1%), 333 (3.2%), 335 (2.1%), 336 (1.2%), 334 (1.1%) |
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Elemental Analysis |
C, 50.58; H, 2.43; N, 8.43; S, 38.57 |
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Dibenzothiazole disulfide, as a multifunctional chemical intermediate, has applications in various industries including rubber industry, pharmaceutical synthesis, special materials, and environmental protection technology.
As a representative of thiazole based vulcanization accelerators, dibenzothiazole disulfide (DM) plays a crucial role in rubber vulcanization systems. Its core function is to accelerate the cross-linking process of rubber molecular chains by reducing the activation energy of vulcanization reaction, thereby improving the physical properties and processing efficiency of the product.
1. Universal vulcanization accelerator
Scope of application: vulcanization promotion of natural rubber, synthetic rubber (such as styrene butadiene rubber, butadiene rubber) and recycled rubber, widely used in non food grade rubber products such as tires, inner tubes, tapes, rubber hoses, rubber shoes, waterproof fabrics, etc.
Performance advantages:
High critical temperature for vulcanization (130 ℃): Compared with accelerator M (critical temperature for vulcanization is about 100 ℃), DM is more stable under high temperature vulcanization conditions, which can avoid early burning and improve operational safety.
Significant post effect: Moderate vulcanization speed, flat vulcanization curve, excellent aging resistance of vulcanized rubber, suitable for thick products and long process processing.
Good dispersibility: When added in the form of pre dispersed masterbatch particles (such as MBTS-75), it can be uniformly dispersed in the rubber matrix, reducing dust pollution and improving mixing efficiency.
Application case:
Tire manufacturing: In all steel radial tires, the combination of DM and thiuram type accelerators (such as TT) can shorten the vulcanization time by 20% -30% and reduce the compression set rate.
Rubber hose production: used for vulcanization of the inner layer rubber of high-pressure rubber hoses, significantly improving the medium resistance and flexural flexibility.
2. Special rubber activator
Unsaturated polyurethane rubber vulcanization: DM, as an active agent for sulfur vulcanization, can improve the vulcanization uniformity of polyurethane rubber and enhance the oil resistance and wear resistance of products.
Anti scorching agent for chloroprene rubber: In G-type chloroprene rubber, the combination of DM and guanidine based accelerators (such as DOTG) can effectively prevent scorching and extend storage life.
High purity DM (pharmaceutical grade) is an important raw material for the synthesis of cephalosporin antibiotics, and its chemical structure is closely related to the construction of the thiazole ring and β - lactam ring.
1. Synthesis of cephalosporin side chains
7-Aminocephalosporanic acid (7-ACA) derivatization: DM undergoes an oxidative ring opening reaction to generate 2-mercaptobenzothiazole carboxylic acid, which is further condensed with 7-ACA to synthesize first generation cephalosporins such as cefazolin and cefradine.
Cephalosporin modification: In the synthesis of third-generation cephalosporins such as cefuroxime and ceftriaxone, DM is used as a side chain precursor to introduce thiazole groups through acylation reactions, enhancing the antibacterial activity and stability of the drugs.
2. Other antibiotic intermediates
Penicillins: Derivatives of DM (such as 2-mercaptobenzothiazoleacetic acid) can be used for the synthesis of penicillin V potassium, improving the oral absorption rate of drugs.
Carbapenems: In the synthesis of imipenem, DM serves as a key intermediate involved in the construction of the β - lactam ring, endowing the drug with broad-spectrum antibacterial properties.
The molecular structure of DM contains active sulfur atoms and conjugated double bonds, which can be chemically modified to endow the material with special properties.
1. Polymer crosslinking agent
Polyurethane elastomer: DM, as a chain extender, can introduce thiazole groups to enhance the heat resistance and chemical corrosion resistance of polyurethane, making it suitable for high-end applications such as seals and coatings.
Epoxy resin curing agent: When used in combination with amine curing agents, DM can adjust the curing speed, reduce internal stress, and improve the mechanical properties of epoxy resin.
2. Metal protective additives
Corrosion inhibitor: The sulfur atoms of DM can form a chemical adsorption film with the metal surface, inhibiting the corrosion of corrosive media (such as H ₂ S, Cl ⁻), and widely used in oil and gas pipelines, ship coatings, and other fields.
Lubricating oil extreme pressure additive: Under high temperature and high pressure conditions, sulfides generated by DM decomposition can react with metal surfaces to form a low shear strength lubricating film, enhancing the extreme pressure and anti-wear performance of gear oil.
With the increasingly strict environmental regulations, the green synthesis and recycling technology of DM has become a research hotspot.
1. Clean production process
Electrochemical synthesis: The indirect electro oxidation coupling process developed by Professor Luo Guangsheng's team uses KI NaI as the electrolyte to electrolyze 2-mercaptobenzothiazole (M) to generate DM, achieving full reuse of mother liquor and zero wastewater discharge, with an atomic utilization rate of 100%.
Hydrogen peroxide oxidation method: Using H ₂ O ₂ as the oxidant and carbonate as the buffer, M is oxidized to form DM under mild conditions (60-80 ℃), avoiding the use of toxic oxidants (such as NaNO ₂/H ₂ SO ₄), significantly reducing environmental risks.
2. Recycling of waste resources
Rubber recycling: DM extracted from waste tires can be reused for rubber regeneration through refining processes, reducing production costs.
Medical waste disposal: DM from cephalosporin antibiotic production waste can be recovered through solvent extraction and crystallization technology, achieving resource recycling.
In order to prepare high-quality medical intermediate 2,2'-dithiobis(benzothiazole) (DM), the environmental friendly oxidant H2O2 and organic solvent were used to oxidize the dimercaptobenzothiazole (M) in one step to obtain DM. Through the investigation of reaction time, reaction temperature, material ratio and other factors, the best process conditions were finally obtained: temperature 40 ℃, feeding time 1 h, reaction time 3 h, sodium carbonate 5% (based on the weight of M), n (M):, n (H2O2)=2:1.1, Three times the organic solvent (based on the weight of M). Under this condition, the melting point of DM can reach 185 ℃, and the purity can reach 99%. With a small amount of surfactant, the final yield can reach 96%.
The invention relates to a synthetic method of medical intermediate, in particular to a synthetic method of 2,2'-dithiobis(benzothiazole). The synthesis method comprises the following steps:
(1) Add 2-mercaptobenzothiazole into the mixed solvent of methanol and water, and dissolve at elevated temperature;
(2) After dissolving and cleaning, add activated carbon for decolorization and filtration. After the filtrate is acidified by strong acid, under the protection of nitrogen, introduce ozone for oxidation and crystallization;
(3) After crystallization, after heat preservation and filtration, the solid product obtained is washed with methanol and dried in vacuum to obtain dibenzothiazole disulfide. This method uses ozone as oxidant, which has good oxidation effect and is green, environmental friendly and pollution-free. The product yield is more than 99%, and the purity of the product is higher than 99%. In the product, the content of 2-mercaptobenzothiazole (M) is less than 0.1%, the other impurities are less than 0.5%, and the melting point is greater than 182 ℃. It can be directly used in the pharmaceutical industry. The solvent can be recycled, reducing production costs.
The purpose of the utility model is to solve the shortcomings of the existing technology, and to propose a production device of dibenzothiazole disulfide. The utility model adopts the following technical scheme:
A production device of dibenzothiazole disulfide is designed, which includes a box body. The bottom side of the box body is provided with a discharge port. The bottom of the box body is fixedly connected with a number of bases. The top of the box body is rotationally connected with a top cover. The central position of the box body is rotationally connected with a rotating shaft through a drive motor. The drive motor is fixedly connected at the bottom of the box body. A number of filter plates are axially connected on the rotating shaft inside the box body, The side of the shaft close to the drive motor is fixedly connected with an annular seat on the same axis, and the outer wall of the shaft is provided with a number of chutes along the axial direction, the filter plate is slidably connected in the chute, the bottom of the chute is above the annular seat, and the outer wall of the end of the shaft close to the top cover is provided with a thread, and the end of the shaft close to the top cover is threaded with a positioning seat, and the bottom of the positioning seat is opposite to the filter plate, The end of the rotating shaft close to the top cover is connected with the top cover through a bearing seat.
The utility model proposes a dibenzothiazole disulfide production device, which has the beneficial effect that: the filter plate set in the utility model can effectively stir and mix the raw materials well, and the filter plate set in the utility model can be detachable with the cooperation of the chute and the slide block, which can be used to disassemble and replace the filter plate through the sliding of the slide block. When replacing, the positioning seat can be removed from the rotating shaft, The filter plate can be pulled out. After the replacement and installation, the positioning seat can be threaded onto the top of the rotating shaft. The operation is simple and practical.
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