Diethyl tartrate, sometimes called 2,3-dihydroxy diethyl succiante, comes from tartaric acid through esterification with ethanol. Chemists often encounter this compound when working with chiral resolution or asymmetric synthesis. Its molecular structure features two ethyl ester groups attached to a central tartrate backbone, giving it both flexibility and stability in a wide range of chemical applications. The chemical formula stands as C8H14O6, and each molecule rests on a molar mass of 206.19 g/mol. In the world of organic chemistry, Diethyl tartrate plays a role as both a building block and a chiral auxiliary, helping to create products with precise stereochemistry, something crucial in fields like pharmaceuticals and specialty chemicals.
This compound shows up most often as a clear, colorless liquid at room temperature. Sometimes, especially at low temperatures or in high purity, crystals begin to form. Anyone who has handled this material knows it carries a faint, sweet odor, hinting at its tartrate origins. It doesn’t dissolve in hydrocarbons, but water, ethanol, and other common polar solvents break it down just fine. Its density comes in around 1.184 g/cm³ at 20°C. Boiling starts at 288°C, and it remains stable in typical laboratory and industrial environments. Diethyl tartrate doesn’t show much volatility, which helps keep handling straightforward and reduces loss through evaporation. The compound may rarely appear in solid, powder, flakes, pearl, or crystal form depending on the storage temperature and process, but liquid is the main commercial offering.
Looking closer, the molecule features two chiral centers at the 2 and 3 positions, making enantiomers and diastereomers possible. The raw materials for its production usually include tartaric acid, a naturally occurring organic acid found in many plants, especially grapes, and ethanol, an alcohol derived from fermentation. Through a controlled esterification process, these feedstocks couple to form the diethyl ester with high purity. Chemists must pay close attention to reaction conditions—too little control causes side products, which can complicate purification. The stereochemistry of the centers can be maintained, giving either the (R,R), (S,S), or racemic forms, with specific uses in different sectors.
Every international shipment needs the right HS Code for customs compliance. Diethyl tartrate generally carries the HS Code 2918.19, which falls under carboxylic acids, derivatives, and their salts and esters. In trade, buyers and suppliers look for material matching standards like minimum purity (usually above 99%), low moisture content, absence of heavy metals, and defined optical rotation. Bulk shipments may come in drum, IBC, or smaller glass bottles, depending on the volume and end-use. Material safety data sheets get reviewed carefully to confirm hazard descriptions, personal protective equipment, and environmental handling requirements.
Diethyl tartrate finds use across several industries thanks to its versatile properties. Perhaps most significant is its role in asymmetric synthesis, where it serves as a chiral starting material or resolving agent. The Sharpless epoxidation reaction—a key method for making enantiomerically pure epoxides in pharmaceuticals—depends heavily on the availability of high-purity diethyl tartrate. It provides both the chiral environment and chemical stability needed for these precise operations. In flavor and fragrance development, the ester’s sweet note sometimes plays a subtle supporting role.
Safety in handling always matters, especially in settings with non-volatile esters like this one. Diethyl tartrate stays classified as a low-toxicity chemical, though swallowing, inhaling, or contacting large amounts can still pose mild harm. Skin and eye irritation can occur, especially with frequent or prolonged exposure. Although combustible, it requires high ignition temperatures, reducing the risk of accidental ignition under regular storage conditions. Material safety data recommend gloves, eye protection, and good ventilation in the workspace. Proper spill management and disposal follow local chemical safety guidelines to protect water systems from contamination. In the event of fire, carbon dioxide, foam, or dry powder extinguishers work best—avoid using water streams, since the material floats and burns on the surface.
Reflecting on the years spent working in labs, the difference a small compound like diethyl tartrate makes becomes clear. Without it, many high-value drug molecules would take longer, cost more, or look quite different due to problems with stereochemistry. The importance isn’t just in the product, but in the efficiency and selectivity it brings to challenging chemical processes. The fact that it can usually be sourced safely, stored for months, and handled without specialized containment makes it a staple in any lab focused on fine chemicals or drug discovery. Pharmaceuticals, agrochemicals, and even specialty polymers owe much to advances made possible by diethyl tartrate and similar building blocks.
Looking at future challenges, reducing the environmental footprint of diethyl tartrate production stands out. More sustainable routes use naturally harvested tartaric acid and greener solvents, while research continues into recycling process streams to capture waste ethanol and byproducts. Advances in purification help deliver purer material while conserving water and energy. Chemical manufacturers can further improve by selecting processes that minimize byproduct toxicity and reduce the need for hazardous reagents. Regulatory trends push for clearer labeling, transparent sourcing of raw materials, and greater oversight of waste handling—all areas where industry participants can step up. Long-term, scaling up production with bio-based feedstocks may offer a way forward, keeping the benefits of diethyl tartrate available while limiting harmful impacts on the planet.
Providing high-quality chemical products and logistics solutions for global trade partners.
