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Sodium p-toluenesulfonate is a white powdery crystal with the molecular formula C7H9NaO3S and CAS 657-84-1. It is easily soluble in water, soluble in methanol, and slightly soluble in most organic solvents. The pH of the 20g/L solution is 8-10. Generally prepared by sulfonation of toluene and neutralization with alkali. When added to the bath gel as a water cosolvent of synthetic detergent, the water content can be increased, which has good effects on fluidity, hand feel and anti caking. Mainly used as a conditioning agent and co solvent for synthetic detergents, as well as an intermediate for drug synthesis. A slurry conditioner used in the chemical industry and synthetic detergents.
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Chemical Formula |
C7H7NaO3S |
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Exact Mass |
194 |
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Molecular Weight |
194 |
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m/z |
194 (100.0%), 195 (7.6%), 196 (4.5%) |
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Elemental Analysis |
C, 43.30; H, 3.63; Na, 11.84; O, 24.72; S, 16.51 |
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Sodium p-toluenesulfinate (CAS number 657-84-1), as an important organic sulfonate compound, has become an indispensable chemical raw material in modern industry due to its unique chemical properties and wide range of applications. Its molecular formula is C ₇ H ₇ NaO ∝ S, with a molecular weight of 194.18, in the form of white crystalline powder, easily soluble in water (with a solubility of 818g/L at 20 ℃), and a melting point higher than 300 ℃. The synergistic effect of sulfonic acid groups and methyl benzene rings endows it with excellent surface activity, chemical stability, and high temperature resistance.
1. The core function of slurry conditioner
In the production of synthetic laundry detergent, sodium p-toluenesulfonate is used as a key conditioner to significantly optimize the powder spraying process by reducing the viscosity of the slurry and improving its flowability. Its addition amount is usually 2-3% (weight ratio), which can achieve four major technical effects:
Viscosity control: The viscosity of the slurry is reduced from 1500mPa · s to below 800mPa · s, and the energy consumption of the powder spraying tower is reduced by 18% -22%;
Moisture content increase: The moisture content of laundry detergent increases by 2-4 percentage points, and the cost per ton decreases by about 30 yuan;
Enhanced anti caking ability: promotes the hydration of pentasodium (sodium tripolyphosphate), increasing the anti caking index of the product from 65% to 82%;
Reduction in fine powder loss: The fine powder content in the tail gas of the powder spraying tower has been reduced from 8% to below 3%, resulting in an annual reduction of over 20 tons of dust emissions.
2. Solubilization and transparency control of liquid detergents
In liquid detergent formulations, sodium p-toluenesulfonat is used as a solubilizer to reduce system viscosity (from 2000mPa · s to 800mPa · s) and cloud point (from 45 ℃ to 38 ℃), while inhibiting the precipitation of inorganic salts. The salt content should be strictly controlled within ≤ 5%, otherwise it will cause the liquid transparency to decrease to a turbid state, affecting the product's market competitiveness.
3. Development of environmentally friendly detergents
Based on its biodegradability (96 hour degradation rate>90%) and low toxicity (LD50>2000mg/kg), sodium p-toluenesulfonat is widely used in concentrated, low phosphorus/phosphate free detergents. For example, replacing traditional AES (fatty alcohol polyoxyethylene ether sulfate sodium) in a certain brand of concentrated laundry detergent can increase the active ingredient content from 15% to 25%, while meeting the EU REACH regulation's requirements for the ecological toxicity of surfactants.
Pharmaceutical synthesis: catalysis and construction of key intermediates
1. Intermediate preparation of antibiotics
Sodium p-toluenesulfonat plays a core catalytic role in the synthesis of β - lactam antibiotics:
Amoxicillin: As a sulfonating agent for hydroxyphenylglycine methyl ester, it improves the reaction selectivity to 92% and reduces the generation of by-products;
Cefotaxil: In the side chain modification of 7-ACA (7-aminocephalosporanic acid), the activation of reaction sites by sulfonic acid groups increases the yield from 65% to 85%;
Doxycycline: As a phase transfer catalyst in the C4 methylation reaction of oxytetracycline, it shortens the reaction time from 12 hours to 4 hours.
2. Synthesis of cardiovascular drugs
In the production of Panshengding (dipyridamole), sodium p-toluenesulfonat was used to construct the key intermediate 2,6-dichloro-4- (3,3-dimethyl-1-triazene) phenol through sulfonic acid esterification reaction, which increased the overall yield from 58% to 75% while reducing the amount of heavy metal catalyst by 60%.
3. Synthesis of nonsteroidal anti-inflammatory drugs
In the synthesis of naproxen, sodium p-toluenesulfonat is used as a methylation reagent to achieve selective methylation of the alpha position of the naphthalene ring under alkaline conditions. The reaction conditions are optimized from high temperature and high pressure (180 ℃, 5MPa) to atmospheric pressure of 120 ℃, reducing energy consumption by 40%.
Dye Industry: Intermediate Synthesis and Performance Optimization
1. Reactive dye intermediates
Sodium p-toluenesulfonat is a key raw material for the synthesis of H acid (1-amino-8-naphthol-3,6-disulfonic acid), which introduces sulfonic acid groups into the naphthalene ring through sulfonation reaction to improve the water solubility and compatibility of dyes. In the production of a certain brand of active black KN-B, its use can increase the dye strength by 15% and the fixation rate from 82% to 88%.
2. Dispersive dye additives
In the synthesis of Disperse Red 3B, sodium p-toluenesulfonat is used as a dispersant to prevent dye particle aggregation through steric hindrance effect, reducing the particle size of the dispersion system from 5 μ m to below 2 μ m and improving the printing clarity by two levels.
3. Cotton fabric bleaching and color enhancement
In the hydrogen peroxide bleaching process, adding 0.5% sodium p-toluenesulfonate can accelerate the bleaching reaction rate by 30%, while reducing fabric strength damage by chelating metal ions, and increasing whiteness by 5-8 CIE units.
1. Ammonium bicarbonate anti caking agent
In the production of ammonium bicarbonate, adding 0.3-0.5% sodium p-toluenesulfonat can inhibit agglomeration through the following mechanism:
Crystal habit regulation: Transforming needle shaped crystals into short columnar shapes, reducing the contact area between particles;
Reduced moisture absorption: The equilibrium moisture absorption rate decreased from 8.2% to 5.5%;
Static elimination: The surface charge density decreased from -15 μ C/g to -5 μ C/g.
Practical application shows that the agglomeration rate has decreased from 35% to below 8%, and the storage period has been extended to 6 months.
2. Compound fertilizer granulation additive
In the production of NPK compound fertilizer, sodium p-toluenesulfonat can be used as a binder to increase particle strength from 15N to 25N, while reducing granulation moisture content by 2-3 percentage points and reducing drying energy consumption by 15%.
Paper and Leather Processing: Functional Material Modification
1. Paper enhancer
In the papermaking process, adding 1% sodium p-toluenesulfonat can improve paper properties through the following ways:
Formation of hydrogen bonds between fibers: increases tensile strength from 35kN/m to 42kN/m;
Improvement in adhesive application: Cobb value decreased from 45g/m ² to 35g/m ²;
The retention rate of fillers has increased from 78% to 85%.
2. Leather dehydration and softening
In the chrome tanning process, sodium p-toluenesulfonat is used as a penetrant, which can shorten the penetration time of the tanning agent from 4 hours to 2 hours. At the same time, the chelation of calcium and magnesium ions can reduce leather hard spots, and the softness score can be increased from 70 points to 85 points (on a 100 point scale).
1. BHT production wastewater recycling
For the production wastewater of antioxidant BHT (2,6-di-tert-butyl-p-cresol) (COD>10000mg/L), the sodium p-toluenesulfonat neutralization evaporation crystallization process is adopted:
PH adjustment: Adjust the pH of the wastewater from 2 to 6-7 using NaOH;
Activated carbon decolorization: COD removal rate reaches 85%;
Evaporation concentration: Crystallize at 120-125 ℃, with a product purity of ≥ 78%;
Economy: With an annual output of 30000 tons, it can reduce COD emissions by over 200 tons, lower energy consumption by 18%, and shorten the environmental cost recovery cycle to 2.3 years.
2. Modification of lignin composite materials
Sodium p-toluenesulfonat can selectively break the ether bonds in lignin carbohydrate complexes (LCC) in acidic hydrothermal systems, promoting lignin directed migration. Compound with lignosulfonate (0.5% addition) can make the composite material:
Durability index: increased from 72 to 84.4;
Mold lifespan: extended by 30%;
Flame retardancy: The synergistic flame retardant increases the oxygen index from 22% to 28%;
Corrosion resistance: The corrosion rate of copper is reduced to 0.002mm/a (in accordance with GB/T 34719-2017 standard).
Preparation of sodium p-toluenesulfonate:
Report I
The environmental protection production method for preparing product from waste sulfuric acid includes the following steps:
(1) In a 500ml three-necked bottle equipped with a thermometer, azeotropic distillation condenser tube and a drip funnel, 217.8 parts of waste sulfuric acid produced after dehydration of hydrochloric acid with 45% content to prepare hydrogen chloride gas are added, and the content is concentrated to 75%, with about 131 parts remaining; Add 117 parts of 99% toluene under stirring at 110 ℃ for 1.5 hours; After dripping, keep reflux at 110 ℃ and separate water from the drain of the oil-water separator at the same time, and the toluene will flow back into the three-mouth bottle; When the volume of water fraction reaches 45 ml, the reaction is completed and the reaction time is 6 hours; Continue heating, distill and recover excessive toluene, and stop collecting toluene when the temperature in the reactor reaches 140 ℃; The weight of collected toluene is 24.4g, and the content is 95.9%;
(2) After the reaction system is cooled to below 70 ℃, slowly drip 30% sodium hydroxide aqueous solution into the reactor under stirring for neutralization reaction, until PH=8, and the dosage of sodium hydroxide aqueous solution is 148 grams; During neutralization, keep the temperature at 70-90 ℃, and continue to stir for 15 minutes after adding sodium hydroxide solution;
(3) Add 2g of powdered activated carbon, stir at 85-90 ℃ for 30 minutes, heat to boiling, and evaporate 45g of water; Then filter while it is hot, and the filter cake is activated carbon and by-product sodium sulfate and a small amount of it; The filtrate is transferred into a beaker, cooled, crystallized, filtered, washed and dried with 15 grams of ice water, and 193.5 grams of it with 79.5% active substance content is obtained, with a yield of 79.3%; The mother liquor is 68.5 g, the active substance content is 41.5%, the conversion yield is 14.7%, and the total yield is 94%.
Report II
A BHT production neutralization wastewater, in which the content of sodium p-toluenesulfonate is 19.8%, and the content of alkali neutralizer (alkali containing sodium ion) is 3.7%. The specific steps of producing product from the neutralized wastewater include: adding an appropriate amount of pH regulator (p-toluenesulfonic acid) into the pH regulating kettle to adjust the pH value of the neutralized wastewater to 6~7, and then pumping it into the decolorizing kettle, adding activated carbon into the decolorizing kettle and heating it to 80~90 ℃, stirring for 1 hour to decolorize, pumping it into the filter press, filtering the activated carbon, and entering the evaporation concentration kettle, heating and evaporating it to 120~125 ℃ at atmospheric pressure, The product is obtained by cooling the slice in the slicer, and the evaporated water vapor is condensed and recycled for the preparation of water for alkali neutralizer. The appearance of the product is white flaky solid. After sampling and analysis, the content of sit is 89.4%, which can meet the refined standard and meet the market quality requirements.
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