Para Toluene Sulfonamide, Tosylamide, Para Methyl Benzene Sulfon Amide, p-Toluenesulfonamide, p-Tosylamide, PTSA, 70-55-3

PARA TOLUENE SULFONAMIDE (PTSA)

Para Toluene Sulfonamide / p-Toluenesulfonamide / p-Tosylamide / 4-Methylbenzenesulfonamide / Tosylamide
CAS Number: 70-55-3
EC Number: 200-741-1

1. PRODUCT IDENTIFICATION AND CHEMICAL IDENTITY

Para Toluene Sulfonamide (p-Toluenesulfonamide) is an important aromatic sulfonamide compound that serves as a key building block in organic synthesis. It is a derivative of benzenesulfonamide with a methyl group (-CH₃) at the 4-position of the benzene ring. This compound appears as white crystalline powder or flakes, is odorless, and has low solubility in water (0.32 g/100 mL at 25°C) but is soluble in alcohol, DMSO, and other organic solvents. It is chemically stable under normal conditions and maintains its stability in neutral, acidic, and basic environments. p-Toluenesulfonamide is known as the major degradation product of Chloramine-T and is also used as an intermediate in saccharin production.

2. PHYSICAL AND CHEMICAL PROPERTIES

p-Toluenesulfonamide is a white crystalline solid in the form of flakes or powder, and is odorless. The melting point ranges from 134-140°C, with the anhydrous form melting at 138.5°C and the hydrated form at 105°C. The boiling point is 221°C at 10 mmHg pressure. The flash point is 202°C, indicating its combustible nature. Water solubility at 25°C is 0.32 g/100 mL, making it sparingly soluble in water, but it is readily soluble in alcohol and DMSO. The LogP value of 0.82 indicates moderate hydrophobic character. The pKa value of 10.17 indicates weak acidic properties.

3. CHEMICAL PROPERTIES AND REACTIONS

p-Toluenesulfonamide is an organic compound containing a sulfonamide group (-SO₂NH₂), which enables various chemical reactions.

Acid-Base Properties:

The sulfonamide group exhibits weak acidic character (pKa 10.17). It can react with strong bases to form salts.

Nucleophilic Reactions:

The sulfonamide group undergoes alkylation and acylation reactions due to the nucleophilic nature of the amine group. This property is utilized in the synthesis of N-tosyl imines and other sulfonamide derivatives.

Thermal Decomposition:

When heated (above 105°C), it decomposes releasing nitrogen gas. This property enables its use as a blowing agent. Gas evolution is approximately 130 mL/g.

Combustion:

Burning produces toxic and irritating gases (nitrogen oxides and sulfur oxides).

Reactivity:

Reacts violently with strong acids, bases, and oxidizing agents.

4. PRODUCTION METHODS

p-Toluenesulfonamide is produced industrially by various methods:

5. APPLICATIONS AND INDUSTRIAL USES

p-Toluenesulfonamide has a wide range of industrial applications due to its versatile chemical properties.

5.1. Plasticizer and Polymer Additive

5.2. Electroplating (Nickel Brightener)

5.3. Organic Synthesis and Chemical Intermediate

5.4. Other Applications

6. SAFETY AND TOXICOLOGY

6.1. Toxicological Data

6.2. Health Effects

NTP Toxicity Studies Summary:

In 14-week feeding studies conducted by the National Toxicology Program (NTP):

• F344/NTac Rats: The most sensitive parameters were increased relative kidney weight in male rats (LOEL: 2,500 ppm; 200 mg/kg) and decreased body weight in female rats (LOEL: 10,000 ppm; 780 mg/kg).

• B6C3F1/N Mice: Increased relative lung weight in male mice (LOEL: 10,000 ppm; 1,760 mg/kg) and increased absolute and relative liver and kidney weights in female mice (LOEL: 10,000 ppm; 1,890 mg/kg) were observed.

• Genetic Toxicology: p-Toluenesulfonamide was not mutagenic in Salmonella typhimurium (TA98, TA100, TA102) with or without metabolic activation. No increase in micronuclei was observed in mouse or rat peripheral blood in in vivo studies.

7. FIRST AID MEASURES

8. SAFETY INFORMATION (GHS CLASSIFICATION)

Signal Word: WARNING

Hazard Statements (H-Codes):

Precautionary Statements (P-Codes):

9. FIREFIGHTING MEASURES

10. ACCIDENTAL RELEASE MEASURES

11. STORAGE AND HANDLING

12. TRANSPORT INFORMATION

13. REGULATORY INFORMATION

Regulatory Status:

14. OTHER NAMES AND SYNONYMS

Database Identifiers:

15. ENVIRONMENTAL INFORMATION

16. RAW MATERIALS AND DERIVATIVE PRODUCTS

16.1. Raw Materials (Upstream)

16.2. Derivative Products (Downstream)

17. APPLICATION SUMMARY TABLE

18. OTHER INDUSTRIAL APPLICATIONS

19. QUALITY CONTROL PARAMETERS

20. SUMMARY AND CRITICAL WARNINGS

SUMMARY:

p-Toluenesulfonamide (C₇H₉NO₂S, CAS 70-55-3) is an important aromatic sulfonamide compound serving as a key building block in organic synthesis. It appears as a white crystalline powder or flakes, is odorless, and has low solubility in water (0.32 g/100 mL at 25°C) but is soluble in alcohol and DMSO. The melting point is 134-140°C, boiling point is 221°C (at 10 mmHg), and flash point is 202°C. It is the major degradation product of Chloramine-T and is used as an intermediate in saccharin production. It is used as a solid plasticizer for thermoset plastics (phenolic, melamine, urea-formaldehyde, polyamide), as a primary brightener in nickel plating (0.2-0.3 g/L), as a precursor for N-tosyl imines, and as a nitrogen source in sulfonamide synthesis. It is also used as a fungicide, mildewcide, disinfectant, and blowing agent. It is FDA approved for use in food packaging adhesives. Toxicologically, it has low toxicity; it may cause skin, eye, and respiratory irritation. NTP studies have shown it is not mutagenic. It is combustible and burning produces toxic nitrogen and sulfur oxides. It should be stored below 30°C in cool, dry, well-ventilated areas.

Key Properties:

Major Application Areas:

Key Safety Points:

• IRRITANT: Causes skin, eye, and respiratory irritation (H315, H319, H335)

• COMBUSTIBLE: Flash point 202°C; burning produces toxic fumes

• REACTIVE: Reacts with strong acids, bases, and oxidizing agents

• STORAGE: Store below 30°C in cool, dry, well-ventilated area

• PPE REQUIRED: Dust mask, safety goggles, protective gloves (for powder handling)

• FDA APPROVED: Approved for use in food packaging adhesives (limited)

CRITICAL WARNINGS:

Use as Plasticizer: p-Toluenesulfonamide is an excellent solid plasticizer for phenolic, melamine, urea-formaldehyde, and polyamide resins. It improves processability, ensures homogeneous solidification, and provides good gloss. When used in thermoset plastics, it enhances mechanical properties and surface quality.

Electroplating Application: As a primary brightener in nickel plating baths, p-toluenesulfonamide is typically used at 0.2-0.3 g/L concentration. It adsorbs on the electrode to improve coating structure and provide brightening effect. It is used in multi-layer nickel plating for uniform bright deposits.

Saccharin Production: p-Toluenesulfonamide is an important intermediate in the production of the artificial sweetener saccharin. This application represents one of the compound's most significant chemical intermediate roles.

N-Tosyl Imine Synthesis: In organic synthesis, p-toluenesulfonamide is used as a precursor for the synthesis of N-tosyl imines (aldimines). These compounds are valuable intermediates in the synthesis of various heterocyclic compounds and pharmaceutical intermediates.

Safety and Toxicology: NTP studies have shown p-toluenesulfonamide has a low toxicity profile. No treatment-related lesions were observed in F344/NTac rats or B6C3F1/N mice in 14-week feeding studies. It was not mutagenic in Salmonella typhimurium (Ames test negative). No increase in micronuclei was observed in mouse or rat peripheral blood in in vivo studies.

Fungicide and Mildewcide: Used as a fungicide and mildewcide in paints, coatings, and wood treatment products. This property particularly enhances product durability in outdoor applications and high-humidity environments by providing antifungal properties to coatings.

Blowing Agent: Upon heating (above 105°C), it releases nitrogen gas for foam formation. Gas evolution is approximately 130 mL/g. This property is used in polymer foam production and fine cell foam formation. The nitrogen gas released during thermal decomposition creates a homogeneous, fine-celled foam structure.

Cosmetic Applications: Used as a plasticizer and skin care additive in cosmetic products. Under EU regulations, its use in cosmetic products as a plasticizer and skin care additive is approved.

FDA Approval: p-Toluenesulfonamide is FDA approved for use in food packaging adhesives (limited). This approval ensures safe use in food contact materials. Use in food packaging adhesives is subject to specific migration limits.

Thermal Stability: p-Toluenesulfonamide decomposes above 105°C releasing nitrogen gas. This property enables its use as a blowing agent. Thermal decomposition gas evolution is approximately 130 mL/g. Processing temperatures should be maintained below this value.

Reactivity Warnings: Reacts violently with strong acids, bases, and oxidizing agents. Contact with these substances should be avoided. It may decompose in acidic or basic environments releasing toxic gases.

Environmental Considerations: Environmental persistence is limited and toxicity is low. LogP value of 0.82 indicates low bioaccumulation potential. Low water solubility limits mobility in aquatic environments.

Transport and Storage: Not classified as a dangerous good, but should be stored carefully due to its combustible nature. Should be kept in cool, dry, well-ventilated areas away from ignition sources. Packaging: 25 kg bags, drums, or FIBCs.

Important Disclaimer: This Technical Data Sheet (TDS) is for informational purposes only. The information provided is based on available data and is believed to be accurate. However, the user is solely responsible for determining the suitability of the product for their specific application and for complying with all applicable regulations and safety requirements. For complete safety, handling, storage, and regulatory compliance information, always refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Users are responsible for testing the product in their own processes and applications. All local, national, and international regulations must be followed when working with p-toluenesulfonamide.