Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (CAS: 6386-38-5), also known as antioxidant BHT-OP or methyl di-t-butyl hydroxyhydrocinnamate, is a high-efficiency sterically hindered phenolic antioxidant. It appears as a white to off-white crystalline solid at room temperature, with a mild characteristic odor. The compound is nearly insoluble in water but soluble in most organic solvents (e.g., methanol, ethanol, toluene, chloroform, and acetone). It is synthesized by esterification of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with methanol, featuring a symmetric molecular structure that endows it with excellent thermal stability and antioxidant activity. As a key intermediate and additive, it is widely used in polymer, lubricant, and plastic industries to inhibit oxidative degradation and extend material service life.
Uses
Polymer Antioxidant: Primary application in polymers such as polyethylene (PE), polypropylene (PP), polystyrene (PS), and ABS resins. It effectively suppresses thermal-oxidative degradation during processing and long-term use, preventing yellowing, brittleness, and mechanical property decline, thus enhancing processing stability and durability of polymer products.
Lubricant & Grease Additive: Widely used in industrial and automotive lubricating oils (engine oil, gear oil) and greases. It improves the thermal stability of lubricants, reduces oxidation and sludge formation, extends oil drain intervals, and protects equipment from wear and corrosion, thereby prolonging the service life of mechanical equipment.
Plastic & Rubber Stabilizer: Applied in plastic products, rubber compounds, and adhesives to resist UV radiation and thermal aging. It maintains the color and mechanical properties of materials under harsh conditions (e.g., high temperature, long-term light exposure), making it suitable for outdoor materials and light-colored products that require high appearance retention.
Intermediate for Antioxidant Synthesis: A critical starting material for preparing other high-performance hindered phenolic antioxidants via transesterification with alcohols (e.g., octadecyl alcohol, pentaerythritol). It serves as a building block for high-molecular-weight antioxidants with low volatility and high compatibility, which are widely used in high-temperature processing materials.
Molecular Formula & Structure
- Molecular Formula: C??H??O?
- Molecular Weight: 292.42 g/mol (292.418 g·mol?1, precise value)
- IUPAC Name: Methyl 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoate
- Synonyms: Methyl di-t-butyl hydroxyhydrocinnamate; BHT-OP; Phenosan methyl ester; 3,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid methyl ester; MFCD00008817; BRN 1915077; PubChem Substance ID: 24868470; EC Number: 228-985-4
- EC Number: 228-985-4
- CAS Number: 6386-38-5
- SMILES Code: COC(=O)CCc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1
- Chemical Structure: The molecule consists of a benzene ring with two tert-butyl groups (-C(CH?)?) at the 3- and 5-positions, a hydroxyl group (-OH) at the 4-position, and a propionate methyl ester group (-CH?CH?COOCH?) at the 1-position. The two sterically hindered tert-butyl groups protect the hydroxyl group from oxidation, while the hydroxyl group acts as the active center to capture free radicals, achieving antioxidant effects. The ester group enhances its compatibility with organic materials such as polymers and lubricants.
Physical & Chemical Properties
- Appearance: White to off-white crystalline solid; odorless or with a mild characteristic odor; no visible impurities.
- Melting Point: 75–79 °C (lit.); Boiling Point: 369.1 °C (at 760 mmHg); Flash Point: 152.4 °C (closed cup); combustible solid, burning produces carbon dioxide and water, no toxic gases.
- Density: 0.987 g/cm3 (25 °C); Refractive Index: n??/D 1.495–1.500 (lit.); Solubility: <0.1 g/L in water (25 °C); soluble in methanol, ethanol, toluene, chloroform, acetone, and mineral oil; slightly soluble in hexane.
- Stability: Excellent thermal stability; decomposes at temperatures above 300 °C; stable under normal storage conditions (cool, dry, sealed). It is resistant to hydrolysis and oxidation, and does not react with common organic solvents or additives. Avoid contact with strong oxidizing agents and strong bases to prevent ester hydrolysis.
- Toxicity: Low toxicity; acute oral toxicity (LD?? > 5000 mg/kg in rats); no skin irritation or eye irritation. It is non-toxic to aquatic organisms and has no obvious environmental impact when used and disposed of properly. GHS labeling: signal word "No Signal Word", hazard statements none; precautionary statements include P261, P264, P270, P301+P312, P330, P501.
Synthesis & Storage
- Synthesis: The main synthetic route is the esterification reaction of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with methanol. The reaction is carried out under acidic catalysis (e.g., sulfuric acid, p-toluenesulfonic acid) at 60–80 °C, with water removed by azeotropy to promote the reaction forward. The crude product is purified by recrystallization (using ethanol or isopropanol as the solvent) to obtain high-purity products with a purity of ≥98.0%.
- Storage: Sealed and stored in a cool, dry, well-ventilated warehouse; recommended storage temperature ≤30 °C. Packed in food-grade polyethylene plastic bags or paper-plastic composite bags, with a net weight of 25 kg per bag. Avoid direct sunlight, high temperature, and moisture; keep away from strong oxidizing agents and strong bases. Store separately from food and beverages. Shelf life: 24 months when unopened and stored properly; use promptly after opening to prevent moisture absorption and caking.
- Safety: Operate in a well-ventilated area; wear nitrile gloves and safety goggles during handling. Avoid skin and eye contact; in case of contact, rinse the affected area with plenty of water. It is non-flammable under normal conditions, but avoid exposure to open flames and high temperatures. Dispose of waste and contaminated containers in accordance with relevant environmental regulations.
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