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Send EmailBenzoic Acid, Benzyl Acid, Phenylformic Acid, Benzene Carboxylic Acid, E210, 65-85-0
Benzoic Acid
1. Product Identity
| Property | Details |
|---|---|
| Product Name | Benzoic Acid |
| CAS Number | 65-85-0 |
| EINECS Number | 200-618-2 |
| Molecular Formula | C₇H₆O₂ (C₆H₅COOH) |
| Molecular Weight | 122.12 g/mol |
| Chemical Name | Benzenecarboxylic acid |
| E Number | E210 |
| MeSH ID | D019817 |
2. Synonyms and Other Names
Common Names
-
Benzoic acid
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Benzenecarboxylic acid
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Phenylcarboxylic acid
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Phenylformic acid
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Benzeneformic acid
Chemical Names
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Carboxybenzene
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Benzenemethanoic acid
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Dracylic acid
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Orthanisic acid
Trade and Technical Names
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Retarder BA
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Retardex
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Tenn-Plas
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Salvo liquid
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Solvo powder
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Purox B
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VevoVitall
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HA 1
-
MENNO-Florades
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NSC 149
Derivative Names
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Benzoate (general name for salts and esters)
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Sodium benzoate (E211)
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Potassium benzoate (E212)
-
Calcium benzoate (E213)
3. Product Description
Benzoic acid is the simplest aromatic carboxylic acid. Structurally, it consists of a benzene ring attached to a carboxyl group (-COOH). It is found in nature in free form as well as in ester form in plants and animals. It is used as a starting material in the production of many important organic compounds.
Key Characteristics:
-
Simplest aromatic carboxylic acid
-
Occurs in nature in free and ester forms
-
Its salts and esters are called "benzoates"
-
Widely used as a food preservative (E210)
4. Physical and Chemical Properties
| Property | Value |
|---|---|
| Appearance | White crystalline solid, needle-like or leaf-shaped crystals |
| Odor | Almost odorless or faint aromatic odor similar to benzaldehyde |
| Taste | Bitter taste |
| Density | 1.3 g/cm³ |
| Melting Point | 122.4 °C |
| Boiling Point | 249 °C |
| pH | Acidic |
| Solubility in Water | At 20°C: 0.29 g/100 mL; At 25°C: 3.44 g/L; At 100°C: 56.31 g/L |
| Solubility in Organic Solvents | Highly soluble in ethyl alcohol, methyl alcohol, and acetone; high solubility in chloroform (CHCl₃) and carbon tetrachloride (CCl₄) |
| Solubility in Acetone | 54.2 g/100 g at 20°C |
| Log P (Partition Coefficient) | 1.87 (lipophilic character) |
| Stability | Highly stable compound |
| Spectroscopy Data | Characteristic carboxyl group vibrations can be identified by IR spectrum |
5. Chemical Structure and Identifiers
| Identifier | Value |
|---|---|
| IUPAC Name | Benzoic acid |
| Molecular Formula | C₇H₆O₂ |
| SMILES | C1=CC=C(C=C1)C(=O)O |
| InChI | InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9) |
| InChI Key | WPYMKLBDIGXBTP-UHFFFAOYSA-N |
| Canonical SMILES | O=C(O)c1ccccc1 |
6. Production Method
Toluene is used as the starting material in benzoic acid production.
Main Production Method: Toluene Oxidation
| Parameter | Details |
|---|---|
| Starting Material | Toluene (C₇H₈) |
| Catalyst | Manganese or cobalt naphthenates |
| Reaction Type | Partial oxidation |
| Reaction | C₇H₈ + O₂ → C₇H₆O₂ + H₂O |
| Conditions | High temperature and pressure |
Alternative Synthesis Methods
| Method | Description |
|---|---|
| Friedel-Crafts Acetylation | Benzene is reacted with acetyl chloride using AlCl₃ catalyst; the resulting acetophenone is oxidized to benzoic acid |
| Tollen Reaction | Methanolic solution of aniline salt is oxidized with potassium permanganate (KMnO₄) or nitric acid |
| Oxidation Method | Toluene is converted to benzoic acid using oxidants such as KMnO₄ or K₂Cr₂O₇ |
7. Natural Sources
Benzoic acid is widely found in nature:
| Source | Description |
|---|---|
| Fruits | Cranberries, blueberries, pineapple |
| Spices | Cloves, cinnamon |
| Mushrooms | Various mushroom species |
| Dairy Products | Can occur naturally in some dairy products |
| Resins | Gum benzoin (benzoin resin) |
8. Applications and Uses
Benzoic acid is a versatile chemical with a wide range of applications.
8.1. Food Industry (As Preservative)
| Application | Function | Description |
|---|---|---|
| General Food Preservative | Antimicrobial | Prevents bacterial, yeast, and mold growth; extends shelf life |
| Beverages | Preservative | Especially in acidic beverages (carbonated drinks, fruit juices) |
| Fruit Juices | Preservative | Prevents black rot in pineapple and other fruit juices |
| Tomato Paste and Ketchup | Preservative | Prevents microbial spoilage |
| Jam and Marmalade | Preservative | Reduces bacterial growth in high-sugar products |
| Cheese | Preservative | Prevents mold formation |
| Canned Foods | Preservative | Maintains freshness, prevents fermentation |
Important Note: In foods, benzoic acid is often used in the form of its sodium salt (sodium benzoate, E211) because the sodium salt has higher solubility. To increase solubility before use, it should be mixed with some ethyl alcohol and hot water.
8.2. Chemical Industry
| Application | Function |
|---|---|
| Phenol Production | Starting material |
| Caprolactam Production | Starting material |
| Sodium Benzoate Production | Intermediate |
| Potassium Benzoate Production | Intermediate |
| Benzoic Anhydride Synthesis | Reactive intermediate |
| Benzyl Alcohol Production | Intermediate |
8.3. Plastics and Polymer Industry
| Application | Function |
|---|---|
| Polymerization Activator | Polymerization initiator in rubber production |
| Polymerization Retarder | Controls reaction rate |
| Rubber Additive | Provides cut resistance and abrasion resistance |
| UV Light Absorber | As ultraviolet light absorber in plastics |
8.4. Cosmetics and Personal Care
| Application | Function |
|---|---|
| Wet Wipes | As preservative, modified with sorbic acid or its salts |
| Cosmetic Products | Antimicrobial preservative |
| Oral Care Products | Preservative and flavoring agent |
8.5. Pharmaceutical and Medical Applications
| Application | Function |
|---|---|
| Antifungal Products | In treatment of ringworm |
| Athlete's Foot Treatment | Antifungal effect |
| Inhalants | As a component |
| Expectorants | As a component |
| Analgesic Decongestants | As a component |
| Metabolism | Conjugated with glycine in the liver to form hippuric acid, excreted through kidneys |
8.6. Agriculture and Animal Husbandry
| Application | Function |
|---|---|
| Plant Protection | Protection against fungal, viral, and bacterial attacks |
| Feed Additive | Antimicrobial additive in products like VevoVitall |
| Weaned Piglets | Regulates intestinal microflora |
8.7. Industrial Applications
| Application | Function |
|---|---|
| Cooling Fluids | T-butyl form as corrosion inhibitor in vehicle engines |
| Underground Drilling Operations | To create temporary blockage |
| Foot Care | Used with salicylic acid to prevent athlete's foot |
| Textile Industry | As bleaching powder |
| Insecticides | In pesticide formulations |
9. Derivatives and Their Applications
| Derivative | Formula | Application Area |
|---|---|---|
| Sodium Benzoate (E211) | C₆H₅COONa | Food preservative, antimicrobial |
| Potassium Benzoate (E212) | C₆H₅COOK | Food preservative |
| Calcium Benzoate (E213) | (C₆H₅COO)₂Ca | Food preservative |
| Benzyl Benzoate | C₆H₅COOCH₂C₆H₅ | Effective against ticks, in pharmaceutical products |
| Benzoyl Peroxide | (C₆H₅CO)₂O₂ | Acne treatment, additive in plastic production |
| Benzoic Anhydride | (C₆H₅CO)₂O | Reactive intermediate in chemical industry |
| Hippuric Acid | C₆H₅CONHCH₂COOH | Metabolic product excreted in urine |
10. Metabolism and Behavior in the Body
| Stage | Process | Description |
|---|---|---|
| Absorption | Intestine | Broken down by intestinal microflora, absorbed through intestinal mucosa |
| Metabolism | Liver | Conjugated with glycine to form hippuric acid (benzoylglycine) |
| Detoxification | Liver | Converted to harmless compound, solubility increases |
| Excretion | Kidneys | Hippuric acid eliminated from the body through urine |
11. Toxicology and Safety
| Parameter | Details |
|---|---|
| Toxicity | Generally low toxicity, may be harmful in high doses |
| Acute Toxicity | Allergic reactions, asthma in high doses |
| Food Safety | Considered safe at low concentrations (E210) |
| Environmental Impact | Biodegradable |
| Allergy | May cause allergic reactions in sensitive individuals |
Animal Studies:
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Negative effects on intestinal microflora in weaned piglets at high doses
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Oxidative disturbances and inflammatory responses observed
12. Anti-inflammatory and Anti-stress Properties
| Property | Mechanism |
|---|---|
| Nrf2 Signaling Pathway Activation | Protective effect in LPS-induced stress conditions |
| TLR4/NF-κB/MAPK Modulation | Contribution to anti-inflammatory mechanisms |
| Antioxidant Effect | Reduction of oxidative stress |
13. Solubility and Distribution
| Solvent | Temperature | Solubility |
|---|---|---|
| Water | 20°C | 0.29 g/100 mL |
| Water | 25°C | 3.44 g/L |
| Water | 100°C | 56.31 g/L |
| Acetone | 20°C | 54.2 g/100 g |
| Ethanol | 20°C | High solubility |
| Methanol | 20°C | High solubility |
| Chloroform | 20°C | High solubility |
| Carbon Tetrachloride | 20°C | High solubility |
Log P Value: 1.87 (lipophilic character, soluble in both water and organic solvents)
14. Frequently Asked Questions (FAQ)
Question 1: What are the uses of benzoic acid?
Answer: Benzoic acid is used as a food preservative, as well as in cosmetics, dyes, plastics, and insecticides. It also serves as an intermediate in the production of phenol, caprolactam, sodium benzoate, and potassium benzoate.
Question 2: What are the potential harms and side effects of benzoic acid?
Answer: While considered acceptable as a food preservative at low concentrations, it can be harmful in high doses and may cause allergic reactions or asthma. It may cause skin irritation in sensitive individuals.
Question 3: What are other names or synonyms for benzoic acid?
Answer: Benzenecarboxylic acid, phenylcarboxylic acid, phenylformic acid, benzeneformic acid, carboxybenzene, dracylic acid, orthanisic acid. Its salts and esters are called "benzoates".
Question 4: What is the chemical formula of benzoic acid?
Answer: The chemical formula of benzoic acid is C₇H₆O₂ or C₆H₅COOH.
Question 5: How does the reaction between benzoic acid and sodium hydroxide occur?
Answer: When benzoic acid reacts with sodium hydroxide, it forms sodium benzoate and water: C₆H₅COOH + NaOH → C₆H₅COONa + H₂O
Question 6: In which natural sources can benzoic acid be found?
Answer: Benzoic acid is naturally found in cranberries, blueberries, pineapple, mushrooms, cloves, and cinnamon. It can also occur naturally in some dairy products, and gum benzoin (benzoin resin) is an important source.
Question 7: What is the E number of benzoic acid?
Answer: The E number for benzoic acid as a food additive is E210. Its sodium salt has code E211, potassium salt E212, and calcium salt E213.
Question 8: How is benzoic acid metabolized in the body?
Answer: Benzoic acid is conjugated with glycine in the liver to form hippuric acid (benzoylglycine) and excreted through the kidneys in urine.
15. Summary
Benzoic Acid (C₇H₆O₂, CAS: 65-85-0, E210) is the simplest aromatic carboxylic acid. It is a white crystalline solid with a faint aromatic odor and bitter taste. It melts at 122.4°C and boils at 249°C. It is slightly soluble in water but highly soluble in organic solvents (ethanol, methanol, acetone, chloroform).
Key Properties:
-
Simplest aromatic carboxylic acid
-
Occurs in nature in free and ester forms
-
Its salts and esters are called "benzoates"
-
Antimicrobial and antifungal properties
-
Stable structure
Main Application Areas:
-
Food Industry: Preservative (E210), especially in beverages, fruit juices, tomato paste, jam, cheese
-
Chemical Industry: Intermediate in production of phenol, caprolactam, sodium benzoate, potassium benzoate
-
Plastics and Rubber: Polymerization activator, UV absorber, rubber additive
-
Cosmetics: Preservative in wet wipes, cosmetic products
-
Pharmaceutical: Antifungal products, inhalants, expectorants
-
Agriculture: Plant protection, feed additive
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Industrial: Cooling fluids, underground drilling, textiles
Derivatives: Sodium benzoate (E211), potassium benzoate (E212), calcium benzoate (E213), benzyl benzoate, benzoyl peroxide, benzoic anhydride, hippuric acid
Metabolism: Conjugated with glycine in the liver to form hippuric acid and excreted through the kidneys
Safety: Considered safe at low concentrations, may cause allergic reactions at high doses. Due to its widespread use as a food preservative, it poses no risk when used within safe limits for human consumption.
