П-Толуолсульфонамид

Description

p-Toluenesulfonamide (4-methylbenzenesulfonamide, tosylamide) - p-toluenesulfonic acid amide, white crystalline powder. Its industrial significance is determined by two directions: plasticization of polymers and condensation with formaldehyde into toluenesulfonamide-formaldehyde resins, which serve as film formers for nail polishes. Hence the trade names Plasticizer 15, Uniplex 173, Topcizer 1S. The third direction is an intermediate product in the synthesis of sweeteners, dyes and pharmaceutical substances.

Basic Attributes

• CAS No.: 70-55-3
• Chemical formula: C7H9NO2S
• Molecular Weight: 171.217
• Exact weight: 171.22
• EU number: 200-741-1
• UNII: I8266RI90M
• ICSC number: 1557
• NSC Number: 9908
• DSSTox ID: DTXSID8029105
• HS code: 2935009090
• PSA Specifications: 68.54
• XLogP3: 0.8
• RTECS number: XT5075000

Physico-chemical indicators

• Appearance: dry powder
• Color and shape: monoclinic plates (dihydrate), white flakes
• Density: 1.271 g/cm³
• Melting point: 138.5 °C
• Boiling point: 214 °C at 9.98 Torr
• Flash point: 202 °C
• Refractive index: 1.564
• Solubility in water: 0.316 g/100 ml at 25 °C
• Steam pressure at 25 °C: negligible
• Henry's law constant: 4.70 × 10⁻⁷ atm m³/mol at 25 °C (calculation)
• Dissociation constant: pKa 10.17 at 20 °C
• Rate constant for reaction with hydroxyl radicals: 1.2 × 10⁻¹² cm³/molecule s at 25 °C (calculation)
• Compatibility: with polyvinyl butyral

The pKa value of 10.17 shows that sulfonamide hydrogen is noticeably more acidic than that of carboxamides: the substance forms salts with alkalis, which is used in isolation and purification. Low solubility in water (0.316 g per 100 ml) and low vapor pressure determine its behavior in products - migration occurs slowly and mainly upon contact with water.

Applications

• plasticizer for thermoplastics and polyamides, compatible with polyvinyl butyral
• raw material for toluenesulfonamide formaldehyde resins - the basic film former for nail polishes
• indirect food additive: according to FDA requirements, o- and p-toluenesulfonamide are approved as a component of adhesives
• intermediate product in the synthesis of dyes, sweeteners, pharmaceutical substances

Safety Information

• Hazard Statements: H319 - Causes serious eye irritation
• GHS classification: signal word “Danger”, H315 (skin irritation) assigned by 14.68% of notifiers; set of measures P260, P264, P271, P280, P284, P302 + P352, P304 + P340, P305 + P351 + P338, P310, P320, P321, P332 + P313, P337 + P313, P362, P403 + P233, P405, P501. Information is aggregated from 11 notifications from 216 companies in the ECHA C&L Register; one notification may apply to several companies
• Labeling Precautions: P305 + P351 + P338
• Tags: Xi; hazard class code: R36; Safety instructions: S26
• WGK Germany: 1; packaging level: III
• Transport codes: NONH for all modes of transport
• Hazardous reactivity: incompatible with strong oxidizing agents and strong bases
• Fire Hazard: Highly flammable, releases irritating or toxic fumes and gases in case of fire

Personal protective equipment

• Eye and face protection: NIOSH (US) or EN 166 (EU) tested.
• Skin protection: work with gloves
• Body protection: selected according to the type, concentration and amount of the substance and the conditions of the workplace
• Respiratory organs: particulate respirator type P95 (USA) or P1 (EN 143); at high levels of exposure - OV/AG/P99 (USA) or ABEK-P2 (EN 143) cartridges

Handling, Spills, Fire Fighting

Dust formation is excluded: further processing of solid material can produce flammable dust, so exhaust ventilation is installed in places where it forms - local suction at the emission source is more economical and reliable than general ventilation. Hands are washed before breaks and at the end of the shift. Spills are collected using a dust-free method: if necessary, moisten, sweep, and pour into closed containers for disposal; When working, use a respirator with a particulate filter, selected according to the concentration of the substance in the air. The product is not discharged into the sewer. Extinguishing media: water spray, alcohol-resistant foam, dry chemical, carbon dioxide; If necessary, firefighters use self-contained breathing apparatus. Inhalation Hazard: When particles disperse, airborne concentrations reach irritant levels quickly. The consequences of short-term exposure are mechanical irritation of the eyes. Prevention: no open flame, ventilation, protective gloves and glasses.

Storage and disposal

Keep the container tightly closed in a dry, well-ventilated place, away from strong oxidizing agents, acids and bases. Unused material, as recommended by SRP, is sent for approved use or returned to the manufacturer or supplier. Final disposal takes into account the impact on air quality, migration in air, soil and water, effects on animals, aquatic and terrestrial flora and fauna, as well as the requirements of environmental and sanitary legislation; If possible, use a less dangerous alternative. Waste that cannot be recycled is transferred to a licensed organization; Contaminated packaging is disposed of as unused product.

Behavior in the environment

The substance is registered in wastewater from industrial enterprises. In wastewater from non-ferrous metallurgy, 22 ng/µl of the extract was found, in wastewater from printing industries - 19 and 841 ng/µl. The compound was identified, but not quantified, in purified water in Pomona, California (24.9/74). In samples of runoff from 6 agricultural fields irrigated with treated wastewater, the concentrations were less than 650 ng/l, in wastewater treatment plant effluents 115–184 ng/l, in stream water dominated by wastewater - less than 630 ng/l. Monitoring of benzenesulfonamides at wastewater treatment plants in Athens for seven days showed the presence of ortho- and para-isomers in 100% of samples with a para-isomer content of up to 1.4 μg/l; benzenesulfonamide was found in all tributaries and 43% of wastewater. Removal efficiencies varied: benzenesulfonamide and the para-isomer were removed at different rates, while the ortho-isomer, on the contrary, was formed during purification. The daily discharge into the Saronikos Gulf amounted to 0.48 kg of ortho isomer and 0.47 kg of para isomer.

Migration from materials

The leaching behavior of a one-component 1C-PU polyurethane coating for hydraulic structures was investigated by non-targeted LC-QTOF-MS analysis. The coating was kept in water for 6 hours, 24 hours, 3 days and 14 days with three curing periods (0 hour, 24 hours, 14 days) and in two water environments - ultrapure and river water, with sequential renewal of water. Organics were washed out under all conditions; The shorter the cure and longer the leaching, the more substances passed into the water; the effect of water type was found to be negligible. Based on the MS2 spectra, 30 substances of five chemical groups were tentatively identified: derivatives of N-(tosyl)carbamate, p-toluenesulfonamide, 4,4'-methylenediphenyl diisocyanate, toluene diisocyanate and oligoethylene [C2H4O]n, as well as p-toluenesulfonic acid. For seven substances, identification was confirmed by reference standards, all of which showed increased bacterial toxicity to Aliivibrio fischeri. In the German Teltowkanal, p-toluenesulfonic acid was present in concentrations of up to 11 µg/l.

The water-soluble fraction of dried nail polish was studied separately. Thin layers of varnish were applied to glass plates, dried for 3 days and extracted with water. The water-soluble components turned out to be para- and ortho-toluenesulfonamide, dibutyl phthalate and 3 components of toluenesulfonamide-formaldehyde resin - the main film-forming material of almost all nail polishes on the world market. 12 patients with a confirmed allergy to varnish were tested with 21 components of the composition, including isolated fractions. Two fractions containing monomer and dimer of resin condensation turned out to be positive; their structure has been established. The third compound, trimer, was negative with one exception.