Glycolonitrile

Glycolonitrile, also known as hydroxyacetonitrile or cyanohydrin, is a simple organic compound with the chemical formula HOCH2CN. It is a colorless liquid that is soluble in water and possesses a slightly sweet odor. Glycolonitrile is an important intermediate in organic synthesis and has applications in the pharmaceutical and agricultural industries. However, it is also a toxic substance and requires careful handling.

Properties and Structure

Glycolonitrile has a molecular weight of 57.05 g/mol and boils at approximately 82 °C at 760 mmHg. Its structure consists of a hydroxyl group (-OH) attached to a methylene group (CH2) that is in turn bonded to a nitrile group (-CN). This structure is responsible for its reactivity and solubility in water.

Synthesis

Glycolonitrile can be synthesized through several methods. One common approach is the hydration of acrylonitrile, which involves the addition of water across the carbon-nitrogen triple bond in the presence of a catalyst. Another method is the reaction of formaldehyde with hydrogen cyanide, facilitated by base catalysts.

Applications

In the pharmaceutical industry, glycolonitrile is used as a precursor to synthesize a variety of compounds, including amino acids, vitamins, and pharmaceutical drugs. In agriculture, it serves as an intermediate in the production of pesticides and herbicides.

Toxicity and Safety

Glycolonitrile is toxic and can be absorbed through the skin, ingested, or inhaled. Exposure to glycolonitrile can lead to symptoms such as headache, dizziness, nausea, and in severe cases, respiratory failure and death. Safety measures include the use of personal protective equipment (PPE), adequate ventilation, and adherence to handling and storage guidelines as per material safety data sheets (MSDS).

Environmental Impact

The environmental impact of glycolonitrile is a concern due to its toxicity. It is important to prevent releases into the environment and to treat spills with caution. Biodegradation and photodegradation are potential pathways for the environmental breakdown of glycolonitrile, but the rates and products of these processes depend on specific conditions.

Regulation

Glycolonitrile is subject to regulation in many countries, with guidelines covering its production, storage, transportation, and disposal. These regulations are designed to protect human health and the environment from the potential hazards posed by glycolonitrile.

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  Glycolonitrile 2D skeletal structure