Benzenesulfonic Acid (also known as sulfobenzoic acid) is an aromatic compound characterized by the presence of a sulfonic acid group attached to a benzene ring. In cosmetics, it is valued for its multifunctional properties, including its role as an exfoliant and its ability to protect the skin from ultraviolet (UV) radiation.
This compound is often utilized in formulations aimed at combating intrinsic skin aging, as it helps remove dead skin cells and promotes a smoother complexion. Additionally, benzene sulfonic acid can act as a stabilizer in cosmetic products, preventing degradation under UV exposure. Its versatility makes it a key ingredient in various skincare and sunscreen formulations
CAS Number: 98-11-3
Molecular Formula: C6H6O3S
Synonyms:
- benzenesulfonic acid, calcium salt
- benzenesulfonic acid hexahydrate, zinc salt,
- sodium benzenesulfonate
- benzenesulfonate
+ 6 more…
- benzenesulfonic acid, iron (+3) salt
- benzenesulfonic acid, zinc salt
- benzenesulfonic acid, potassium salt
- benzenesulfonic acid, magnesium salt
- benzenesulfonic acid, sodium salt
- benzenesulfonic acid, ammonium salt
Uses of Benzenesulfonic Acid in Cosmetics
Functional role in cosmetics:
- Benzenesulfonic Acid is used as a cleansing and exfoliating agent in cosmetics.
Cosmetic Products Containing Benzenesulfonic Acid
Recent products using Benzenesulfonic Acid in their cosmetic formulations
- David&David Smoothing Conditioner
Top companies using Benzenesulfonic Acid in their cosmetic products
- David&David
Regulatory Considerations for Using Benzenesulfonic Acid in Cosmetic Formulations
Few regulatory considerations are to be taken into account before using Benzenesulfonic Acid as an ingredient. Given below is the list of those regulations:
REACH Registered Substance: Benzenesulfonic Acid is registered under REACH with active statuses updated on August 31, 2022, and March 23, 2018.
New Zealand EPA Inventory of Chemical Status: Benzenesulphonic acid does not have individual approval but may be used under an appropriate group standard.
The Australian Inventory of Industrial Chemicals: Listed as Benzenesulfonic Acid in the Australian Inventory of Industrial Chemicals.
Alternatives of Benzenesulfonic Acid and Comparative Analysis
Given below is the list of alternative ingredients that can be used in place of Benzenesulfonic Acid in cosmetic formulations:
- Sodium Lauryl Sulfate (SLS)
- Sodium Dodecylbenzenesulfonate
- Sodium Coco-Sulfate
- Sodium Lauryl Sulfoacetate
- Sodium Cocoyl Isethionate
Comparative analysis of Benzenesulfonic Acid alternative ingredients:
| Ingredients | Strengths | Limitations | Efficacy | Cost | Stability | Compatibility | Safety |
| Sodium Lauryl Sulfate (SLS) | Powerful anionic surfactant with excellent cleansing and foaming properties Widely used in shampoos, body washes, and cleansers Effective emulsifier and dispersant | Can be irritating to sensitive skin and eyes May cause dryness with frequent use | High as a surfactant and cleanser | Low | High | Good with most cosmetic ingredients | Potential irritant for sensitive skin |
| Sodium Dodecylbenzenesulfonate | Anionic surfactant derived from benzenesulfonic acid salts Excellent wetting, emulsifying, and dispersing properties Effective in laundry detergents and industrial cleaners | Can be harsh on skin, limited use in personal care products Requires neutralization before use | High as a surfactant and detergent | Low to moderate | High | Good in alkaline and detergent formulations | May cause irritation; use with caution in cosmetics |
| Sodium Coco-Sulfate | Derived from natural coconut oil and benzenesulfonic acid derivatives Good foaming and cleansing properties More biodegradable than some synthetic surfactants | Can still cause irritation in sensitive skin Less mild than non-ionic or amphoteric surfactants | Moderate to high as a surfactant | Moderate | High | Good with other surfactants and cosmetic ingredients | Generally safe but may irritate sensitive skin |
| Sodium Lauryl Sulfoacetate | Mild anionic surfactant with good foaming and cleansing Gentler alternative to traditional sulfates Suitable for sensitive skin and baby products | Less effective in heavy-duty cleaning compared to stronger surfactants Higher cost than common sulfates | Moderate as a mild surfactant | Moderate to high | High | Good with most cosmetic formulations | Generally safe and non-irritating |
| Sodium Cocoyl Isethionate | Mild, sulfate-free surfactant derived from coconut fatty acids Produces creamy foam and gentle cleansing Widely used in sensitive skin and baby care products | More expensive than traditional sulfates May require combination with other surfactants for desired texture | High as a mild surfactant and cleanser | High | High | Excellent with various cosmetic ingredients | Safe and well tolerated |
How Benzenesulfonic Acid Works in Formulations
Benzenesulfonic Acid is typically used as an intermediate in the synthesis of other cosmetic ingredients, rather than as a direct cosmetic ingredient. It plays a critical role in the production of surfactants and emulsifiers, essential for cleansing products.
Ideal Concentration and Benefits in Different Formulations
Use in Surfactant Production
Benzenesulfonic Acid is involved in the production of sulfonate-based surfactants, which are key ingredients in many cleansing products. It contributes to the creation of detergents and emulsifiers, making it essential for formulating cleansing agents
Catalyst and pH Adjuster
Used in small amounts to adjust pH or catalyze reactions during formulation processes. Due to its corrosive nature, it requires controlled handling and proper neutralization before use in final products.
Compatibility with Other Ingredients
Highly acidic and corrosive; requires careful handling and neutralization before use in consumer products. Incompatible with alkaline substances and certain metals. Not intended for direct application onto skin.
Stability and Shelf Life
Stable under normal storage conditions when kept in airtight, corrosion-resistant containers. Shelf life depends on storage conditions; moisture and contaminants can affect stability. Requires protection from heat and light to maintain integrity.
Formulation Challenges and Troubleshooting
Benzenesulfonic Acid presents several formulation and safety challenges due to its chemical properties:
Corrosiveness
Benzenesulfonic Acid is highly corrosive, posing risks to both formulators and packaging materials.
Solution: Use appropriate protective equipment and corrosion-resistant materials (e.g., glass or specialized plastics) for storage and handling.
Environmental Toxicity
It can be toxic to aquatic life if released without proper treatment.
Solution: Implement strict waste management protocols and wastewater treatment to minimize environmental impact.
Compatibility Issues
Incompatible with alkaline compounds and some metals, which can cause degradation or hazardous reactions.
Solution: Avoid contact with incompatible materials and adjust formulation chemistry accordingly.
Regulatory Restrictions
Regulations may limit the use or handling of Benzenesulfonic Acid due to its hazardous nature.
Solution: Comply with local and international regulations for storage, transport, and disposal.
Environmental and Sustainability Impact
Benzenesulfonic Acid is an aromatic sulfonic acid used in cosmetics primarily as an intermediate in the synthesis of other ingredients. Its use raises environmental and safety considerations:
Environmental Impact
- Water Pollution: Benzenesulfonic Acid is water-soluble and can be toxic to aquatic organisms if released in large quantities. Proper waste management is essential to prevent environmental contamination.
- Carbon Footprint: The production of Benzenesulfonic Acid involves sulfonation of benzene, a petrochemical process that contributes to greenhouse gas emissions and energy consumption.
Sustainability
The sustainability of benzenesulfonic acid is limited by its petrochemical origin and energy-intensive manufacturing process.
- Raw Materials: Derived from benzene, a non-renewable petrochemical resource, restricting its sustainability potential.
- Energy Use: Manufacturing requires significant energy input due to high-temperature sulfonation reactions.
- End-of-Life Impact: Benzenesulfonic Acid can biodegrade under aerobic conditions but may persist in anaerobic environments, potentially leading to environmental accumulation.
Biodegradability and Toxicity
Benzenesulfonic acid exhibits moderate biodegradability but can be toxic to aquatic organisms at elevated concentrations.
Ammonia Toxicity: Not applicable. Benzenesulfonic Acid does not release ammonia during degradation.
Eco-Friendly Alternatives
Due to its petrochemical origin and toxicity risks, sustainable alternatives for benzenesulfonic acid or its derivatives include:
- Bio-Based Sulfonates: Sulfonated compounds derived from natural oils or biomass that offer improved biodegradability and lower toxicity.
- Aromatic Sulfonates from Renewable Sources: Renewable aromatic sulfonic acids synthesized via green chemistry routes.
- Non-Sulfonic Acid Intermediates: Alternative compounds used as intermediates in cosmetic ingredient synthesis without sulfonic acid groups.
Benzenesulfonic Acid Side Effects
Benzenesulfonic Acid is known for its corrosive properties, posing significant risks to human health and the environment. It is classified as harmful if swallowed, with an oral LD50 greater than 1,104 mg/kg in rats. The compound causes severe skin burns and eye damage, categorized as a serious eye irritant and skin corrosive.
Inhalation can lead to respiratory irritation, including coughing and inflammation of the mucous membranes. While there is limited data on its carcinogenic potential, it is not classified as a carcinogen by major regulatory bodies. However, its toxicity to aquatic life has been noted, with harmful effects observed in algae and aquatic invertebrates.
Symptoms
- Eye Exposure: May cause redness, pain, and severe deep burns.
- Skin Exposure: May cause redness, burning sensation, pain, and skin burns.
- Ingestion Exposure: May lead to sore throat, burning sensation in the throat and chest, abdominal pain, and shock or collapse.
- Inhalation Exposure: May cause coughing, sore throat, shortness of breath, laboured breathing, burning sensation, headache, and nausea.
Adverse Effects
Benzenesulfonic Acid can cause serious skin burns, classifying it as a dermatoxin. It may also lead to toxic pneumonitis, a condition involving lung inflammation triggered by inhaling harmful metal fumes or toxic gases and vapors.
Exposure Routes
The substance can be absorbed into the body by inhalation and by ingestion.
Human Toxicity Excerpts
Benzenesulfonic Acid is generally not associated with serious systemic or cumulative effects. However, anomalies have been noted between its acid ionization constants and the extent of local tissue damage. Contact with heated vapor or sublimates may cause irritation to the upper respiratory tract, eyes, and skin.
Non-Human Toxicity Excerpts
Benzenesulfonic Acid caused significant eye irritation in rabbits, receiving a rating of 9 out of 10 in ocular tests. This rating was based on the degree of eye injury observed 24 hours after exposure, with special focus on corneal damage. A score of 10 represents the most severe injury possible.
Antidote and Emergency Treatment
There is no specific antidote for Benzenesulfonic Acid exposure, so medical care focuses on supportive measures. If exposure occurs, it is essential to move the individual away from the source and into fresh air. Skin that has come into contact with the substance should be thoroughly washed with soap and water, and eyes should be flushed with plenty of water. Prompt medical evaluation and treatment are strongly recommended.
Properties of Benzenesulfonic Acid
Chemical Identifiers
| EC Number | 202-638-7 |
| UNII | 685928Z18A |
| InChIKey | SRSXLGNVWSONIS-UHFFFAOYSA-N |
| SMILES | C1=CC=C(C=C1)S(=O)(=O)O |
| IUPAC Name | benzenesulfonic acid |
| InChI | InChI=1S/C6H6O3S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H,(H,7,8,9) |
Physical and Chemical Properties
Benzenesulfonic Acid is an organosulfur compound with the molecular formula C6H6O3S and a molar mass of 158.18 g/mol. It appears as colorless deliquescent sheet crystals or a white waxy solid. The melting point of its anhydrous form ranges from 50–51°C, while its hydrated form melts at 43–44°C.
It has a boiling point of 137°C and a density of 1.32 g/cm³. Benzenesulfonic acid is highly soluble in water and ethanol, slightly soluble in benzene, and insoluble in nonpolar solvents like diethyl ether and carbon disulfide. Its aqueous solution is strongly acidic, with a pKa value of 0.699 at 25°C.
| Property | Value |
| LogP | -1.2 |
| Density | Relative density (water = 1): 1.3 (47°C) |
| Color/Form | Fine, deliquescent needles or large plates |
| Solubility | 5 to 10 mg/mL at 72°F |
| Flash Point | 113°C |
| Boiling Point | 190°C |
| Melting Point | 109 to 111°F |
| Vapor Density | Relative vapor density (air = 1): 5.5 |
| Vapor Pressure | 0.0000236 mmHg |
| Collision Cross Section | 127.2 Ų [M-H]- |
| Other Experimental Properties | With 1.5 molecules of water, mp is 43-44 °c |
Structural Properties
Benzenesulfonic acid is a molecule with moderate complexity, consisting of 10 atoms, including a few that play roles in hydrogen bonding. It has a single rotatable bond and is stable in its canonical form. The compound is neutral (no formal charge) and has both hydrogen bond donor and acceptor sites, with three acceptors and one donor.
Its surface area, which interacts with water, is notable. Overall, it’s a relatively simple structure with the ability to form hydrogen bonds, which may influence its solubility and interactions in different environments.
| Property | Value |
| XLogP3 | 0 |
| Complexity | 184 |
| Exact Mass | 158.00376522 g/mol |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Molecular Weight | 158.18 g/mol |
| Monoisotopic Mass | 158.00376522 g/mol |
| Isotope Atom Count | 0 |
| Rotatable Bond Count | 1 |
| Compound Is Canonicalized | Yes |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Covalently-Bonded Unit Count | 1 |
| Topological Polar Surface Area | 62.8 Ų |
| Defined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
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