Overview
Crotonic acid (2-butenoic acid) is an unsaturated four-carbon carboxylic acid with a trans-configuration. It is industrially synthesized through oxidation of crotonaldehyde or as a byproduct of acetic acid production. As a monomer, it is valued for its ability to copolymerize with vinyl acetate and other compounds. Its IUPAC name is (2E)-2-butenoic acid, reflecting the trans-arrangement of its double bond. The compound is classified as a hazardous substance due to its corrosive nature and requires careful handling in industrial settings.
Physical and Chemical Properties
Crotonic acid forms needle-like crystals with a characteristic acrid odor. Its solubility profile includes 1g/6mL in cold water and complete miscibility with alcohols. The acid exhibits typical carboxylic acid reactivity, forming salts (crotonates) and esters. The double bond makes it susceptible to addition reactions and polymerization. Thermal decomposition occurs above 185°C, releasing corrosive fumes. Its pKa is 4.69, indicating moderate acidity comparable to acetic acid. The crystalline form is stable under recommended storage conditions.
Main Applications
Approximately 60% of crotonic acid production is used in polymer chemistry as a co-monomer for vinyl acetate copolymers, improving flexibility and adhesion in paints/coatings. Pharmaceutical applications include synthesis of antihypertensive intermediates and topical medications. Other uses include: production of plasticizers (crotonate esters), food preservatives (calcium crotonate), and specialty chemicals. Recent research explores its potential in biodegradable polymers. Industrial-grade purity (98-99%) suffices for most applications, while pharmaceutical uses require ≥99.5% purity.
Safety and Storage
Classified as Corrosive (Category 1B) under GHS, crotonic acid requires acid-resistant packaging (HDPE or glass) with airtight seals. Storage areas should maintain temperature below 30°C with relative humidity under 65%. Emergency measures include: acid-resistant PPE (nitrile gloves, face shield), neutralization spills with sodium bicarbonate, and ventilation to prevent vapor accumulation. SDS documentation must accompany shipments, noting UN3261 (Corrosive solid, acidic, organic) for transportation compliance.
B2B Procurement Guide
Industrial buyers should specify: purity grade (technical/pharma), packaging (25kg drums/bulk), and certificates of analysis. Spot prices fluctuate with maleic anhydride market trends (a common feedstock). Reliable Asian suppliers typically offer 98% purity at $20-30/kg for 1-ton quantities, while European producers charge premium prices for pharma-grade. Request stability data for long-term storage. Just-in-time procurement is recommended due to limited shelf life (12-18 months in optimal conditions).
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