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Sodium diethyldithiocarbamate abbreviated as DDTC, is an organic salt with the molecular formula C5H10NS2Na. Presented as a white to light yellow solid, pure DDTC crystals are colorless and transparent. Easy to dissolve in water, as well as organic solvents such as alcohol, chloroform, and ether. However, its solubility in ethyl acetate and benzene is relatively low. Has a high hardness, with a Mohs hardness of approximately 2.5. In addition, it also has good wear resistance, but is not resistant to impact. It is a strong alkaline weak acid salt with high alkalinity and chemical reactivity. It can undergo hydrolysis reactions in aqueous solutions, generating sodium hydroxide and corresponding acids. In addition, it can also form complexes with certain metal ions. It can be used to synthesize complex materials with special properties. For example, through the reaction of DDTC with certain metal ions, complex materials with optical, electrical, magnetic and other characteristics can be prepared. These materials have broad application prospects in sensors, catalysts, optoelectronic materials, and other fields.
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Chemical Formula |
C5H10NNaS2 |
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Exact Mass |
171.02 |
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Molecular Weight |
171.25 |
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m/z |
171.02 (100.0%), 172.02 (5.4%), 173.01 (4.5%), 173.01 (4.5%), 172.01 (1.6%) |
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Elemental Analysis |
C, 35.07; H, 5.89; N, 8.18; Na, 13.42; S, 37.44 |
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1. Oxidation to disulfide: the oxidation of sodium diethyldithiocarbamate produces disulfide, namely thiuram disulfide:
2 NaS2CNEt2+ I2→ Et2NC(S)S-SC(S)NEt2+ 2 NaI
This disulfide is sold under the names of antause and disulfiram as an anti alcoholism drug. Chlorination of the disulfide can provide aminothiocarbonyl chloride.
2. As a ligand: diethyldithiocarbamate can chelate with many "soft" metal ions through two sulfur atoms. Other more complex bonding modes are also known, such as the use of one of the two sulfur atoms as a monodentate ligand or a bridging ligand. It is sometimes called copper reagent because it can form a planar square complex with copper ions, and the gray green complex can be extracted by carbon tetrachloride.
3. Spin trapping of nitric oxide free radicals: diethyldithiocarbamate iron complex is one of the few methods that can provide research on the formation of nitric oxide (no) free radicals in biomaterials. Although the tissue half-life of no is so short that it cannot be detected by itself, no is easy to bind to this complex. The mononitrosyl iron complex (UK: mnic) formed is stable and can be detected in the spectrum by electron spin resonance (EPR).
Sodium diethyldithiocarbamate is an important organic compound that can be used to synthesize various drugs and pesticides. The following are the detailed steps for preparing product:
1. Prepare reagents and equipment
Carbon disulfide: Add carbon disulfide to a dry flask and stir with a mechanical stirrer for subsequent reactions.
Diethylamine: Add diethylamine to another dry flask and stir with a mechanical stirrer for subsequent reactions.
Sodium hydroxide: Add sodium hydroxide to water to prepare a certain concentration of sodium hydroxide solution for subsequent reactions.
Desiccants: such as anhydrous calcium sulfate or magnesium perchlorate, used to dry reactants and products.
Separation equipment: such as separation funnels, filtration devices, etc., used to separate reactants and products.
2. Preparation of sodium diethyldithiocarbamat
2.1 Mixing carbon disulfide and diethylamine: Add carbon disulfide to diethylamine and stir evenly to facilitate subsequent reactions.
2.2 Neutralization with sodium hydroxide: Add the sodium hydroxide solution to the above mixture and stir evenly to facilitate subsequent reactions.
2.3 Heating reaction: Heat the mixture to a certain temperature (e.g. 60 ° C) and maintain it for a certain time (e.g. 30 minutes) to facilitate the reaction.
2.4 Separation of products: Pour the reacted mixture into a separating funnel, wash the product with an appropriate amount of water, and add an appropriate amount of desiccant for subsequent separation.
2.5 Drying product: Put the product into a vacuum dryer and dry it at a certain temperature for a certain time (such as 24 hours) to obtain the final product.
3. Chemical equation
(CH3CH2)2N-S-S-N(CH3CH2)2 + 2NaOH → (CH3CH2)2N-S-S-N(CH3CH2)2 + 2NaOH → (CH3CH2) 2N-S-S-N(CH3CH2)2 + 2NaOH
On the left is a mixture of carbon disulfide and diethylamine, in the middle is an intermediate in the reaction process, and on the right is the final product. The function of sodium hydroxide is to neutralize the acid produced during the reaction process, in order to redirect the reaction towards the direction of generating the final product.
Sodium Diethyl Dithiocarbamate (DDTC), as an organic sulfur compound, has shown wide application value in industries, agriculture, medicine, analytical chemistry, and materials science due to its unique chemical structure and reactivity.
1. Nobs
DDTC is a classic accelerator for synthetic rubber such as natural rubber, styrene butadiene rubber, and nitrile rubber. When used in combination with zinc oxide, stearic acid, etc., it can significantly shorten the vulcanization time and improve the vulcanization efficiency. Its mechanism of action is to form a cross-linked structure between sulfur atoms and rubber molecular chains, endowing rubber products with excellent physical properties such as strength and elasticity. Typical applications include the production of latex products, self sulfurizing adhesives, impregnated products, and thin films. The recommended dosage in latex is 0.5-1.5 parts, which can achieve a balance between vulcanization speed and product quality.
2. Metal sulfide ore flotation collector
In the mineral processing industry, DDTC serves as a special collector for sulfide minerals such as copper, lead, and antimony. By forming stable complexes with metal ions through sulfur atoms in its molecules, it achieves efficient separation of minerals and gangue. Experiments have shown that the complex formed between DDTC and Cu ² ⁺ can enhance the copper displacement precipitation rate and significantly optimize the mineral processing recovery rate. In addition, its aqueous solution is alkaline and easily decomposable, making it both environmentally friendly and economical in the flotation process.
3. Metal ion precipitation and solvent extraction
DDTC can form insoluble chelates with soft metal ions such as copper, zinc, cobalt, platinum, palladium, etc., and is widely used in heavy metal wastewater treatment and precious metal recovery. For example, in the treatment of electroplating wastewater, DDTC can efficiently remove copper ions and reduce wastewater toxicity through precipitation; In the field of precious metal extraction, its strong chelating ability with platinum group metals provides technical support for the resource utilization of low-grade ores.
Agricultural field: Green plant protection and crop growth regulation
1. Low toxicity fungicide
DDTC has significant inhibitory activity against plant pathogenic fungi such as Fusarium and anthrax, and its mechanism of action includes disrupting fungal cell membrane structure and inhibiting spore germination. Compared with traditional fungicides, DDTC has advantages such as biodegradability, no residue, and environmental friendliness, which meet the needs of sustainable development in modern agriculture. For example, spraying DDTC solution in sheep grass planting can significantly inhibit heading rate and enhance nutritional value, providing high-quality forage for animal husbandry.
2. Plant hormone balance regulator
Research has shown that DDTC can affect crop growth and development by regulating the synthesis and transport of endogenous hormones such as auxin and gibberellin. In wheat experiments, a suitable concentration of DDTC solution can promote an increase in tiller number, but excessive use may lead to a decrease in self fertilization rate, indicating that its application should strictly follow the concentration effect relationship.
Medical field: Exploration of immune regulation and disease treatment
1. Chronic infection and immune enhancers
DDTC is used as an adjuvant treatment for chronic infections (such as tuberculosis and HIV infection) by enhancing the function of T lymphocytes and cellular immune activity. The clinically recommended dose is 5mg/kg, which can significantly improve the patient's immune response level. In addition, its synergy with antiretroviral drugs (such as zidovudine) provides a new strategy for AIDS treatment.
2. Research on cancer adjuvant therapy
DDTC inhibits the activity of metalloproteinases and blocks the pathway of cancer cell metastasis by chelating zinc ions; Meanwhile, as a superoxide dismutase (SOD) inhibitor, it can weaken the antioxidant defense system of tumor cells. Animal experiments show that DDTC can reduce the nephrotoxicity of cisplatin chemotherapy without affecting the anti-tumor effect, and prolong the survival period of AIDS model mice, suggesting its potential value in the comprehensive treatment of cancer.
3. Neuroprotective and anti-inflammatory applications
DDTC can exert neuroprotective effects by inhibiting the induction of macrophage nitric oxide synthase (iNOS) and reducing the release of inflammatory factors. In the model of cerebral ischemia-reperfusion injury, DDTC pretreatment can significantly reduce the infarct area and improve neurological deficits.
Analytical Chemistry: Metal Detection and Quantitative Analysis
1. Copper reagent and photometric determination
DDTC is a specific color reagent for copper ions, and its gray green complex formed with Cu ² ⁺ can be extracted by carbon tetrachloride. The sensitive detection of copper can be achieved by colorimetric method (with a detection limit of ppb level). In addition, this reaction system can be extended to the determination of metal ions such as zinc, cobalt, and nickel, and is widely used in environmental monitoring, food analysis, and geological exploration fields.
2. Separation and Enrichment of Heavy Metals
In the pretreatment of atomic absorption spectroscopy (AAS) and inductively coupled plasma mass spectrometry (ICP-MS), DDTC achieves the separation and enrichment of heavy metals by forming insoluble chelates. For example, in the sodium chloride DDTC propanol system, the extraction rate of copper can reach over 99%, significantly improving the analytical sensitivity.
3. Free radical detection probe
The complex formed by DDTC and iron ions can be used as a spin trap in electron spin resonance (EPR) technology for quantitative detection of nitric oxide (NO) free radicals in living organisms. This method breaks through the limitation of short half-life of NO and provides an important tool for the study of cardiovascular disease and inflammatory response mechanisms.
Materials Science: Synthesis and Performance Optimization of Functional Materials
1. Precursor of vulcanization accelerator
DDTC is a key intermediate for the synthesis of overspeed promoters such as tellurium diethyldithiocarbamate (TDEC) and selenium diethyldithiocarbamate (SE). This type of accelerator has the characteristics of fast vulcanization speed and high tensile strength, and is widely used in the production of low-temperature vulcanized rubber products (such as cable insulation layers and seals).
2. Nanomaterial synthesis template
Metal sulfide nanoparticles (such as CuS and ZnS) can be prepared by utilizing the strong chelating effect between DDTC and metal ions. By adjusting reaction conditions such as pH and temperature, precise control of nanoparticle morphology (spherical, sheet-like) and size (5-50nm) can be achieved, providing high-performance materials for photocatalysis, sensors, and biological imaging fields.
3. Corrosion inhibitors and anti-corrosion coatings
The combination of DDTC and thiourea can significantly inhibit the corrosion rate of AZ91D magnesium alloy in 3.5% NaCl solution, and its mechanism of action includes the formation of a protective complex film on the metal surface and the inhibition of chloride ion penetration. This technology provides an economical and efficient solution for the anti-corrosion treatment of marine engineering equipment.
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