3-Hydroxypropionitrile CAS No. 109-78-4

Uses and Applications

3-HPN is a highly versatile bifunctional chemical intermediate whose value lies in its conversion to numerous important downstream products.

• Polymer & Material Precursors:

  • Acrylamide & Polyacrylamide: Dehydration of 3-HPN yields acrylonitrile, which is hydrated to acrylamide and then polymerized. Polyacrylamide is a crucial water-soluble polymer used in water treatment, petroleum recovery, papermaking, and textiles.

  • 1,3-Propanediol (PDO): Complete hydrogenation of the nitrile group produces 1,3-Propanediol, a key monomer for the high-performance polyester Polytrimethylene Terephthalate (PTT) used in fibers and engineering plastics.

  • Acrylic Acid & Esters: Via hydrolysis and esterification, 3-HPN serves as a precursor to acrylic acid and its esters, used in paints, adhesives, and acrylic resins.

  • Specialty Monomers: It is used in the synthesis of functional monomers for specialty polymers.

• Pharmaceutical & Agrochemical Intermediates:

  • 3-Aminopropanol: Catalytic hydrogenation of the nitrile group yields 3-aminopropanol, an essential building block for pharmaceuticals (e.g., vitamin B1/B6, cyclophosphamide, propranolol) and dyes.

  • It acts as a synthetic precursor for various active pharmaceutical ingredients (APIs) and agrochemicals.

• Fine Chemicals & Functional Materials:

  • 3-Hydroxypropionic Acid (3-HP): Enzymatic or chemical hydrolysis of the nitrile produces 3-HP, an important platform chemical for synthesizing biodegradable polymers, cosmetics, and personal care products (e.g., moisturizers).

  • Epoxy Curing Agents & Additives: Used as a component in low-temperature curing systems for epoxy resins and as an additive in textile, leather, and paper industries for dyeing, wetting, and cross-linking.

• Solvent & Research Applications:

  • Serves as a solvent and extraction agent due to its dual hydrophilic/hydrophobic character.

  • Used as a reagent in organic synthesis research and reaction mechanism studies.

  • Featured in physicochemical studies, such as investigating surfactant (e.g., lecithin, DOPC) behavior and critical aggregation concentrations.

Chemical and Physical Properties

• Basic Identification:

  • Chemical Names: 3-Hydroxypropionitrile, 3-Hydroxypropanenitrile, Ethylene Cyanohydrin, β-Hydroxypropionitrile.

  • Molecular Formula: C₃H₅NO

  • Structure: HO–CH₂–CH₂–C≡N

  • CAS Registry Numbers: 109-78-4 (primary), 5068-24-0.

  • Molar Mass: 71.08 g/mol

  • Appearance: Colorless to pale yellow transparent oily liquid with a mild, characteristic or irritating odor.

• Physical Properties:

  • Melting Point: ≈ -46 °C

  • Boiling Point: Decomposes near 228 °C at atmospheric pressure; typically distilled under reduced pressure.

  • Density: ≈ 1.040 g/cm³ at 25°C

  • Refractive Index: ≈ 1.424 at 25°C

  • Flash Point: > 110 °C

  • Solubility: Miscible with water, ethanol, acetone, and chloroform. Slightly soluble in diethyl ether. Insoluble in non-polar solvents like benzene and petroleum ether.

• Chemical Properties:

  • Key Feature: A bifunctional molecule containing a hydrophilic hydroxyl group (-OH) and a lipophilic nitrile group (-CN).

  • Reactivity: The nitrile group can undergo hydrolysis (to amide/acid), reduction (to amine), and alcoholysis. The hydroxyl group can be esterified or oxidized.

  • Stability: Can be unstable at room temperature, prone to polymerization or decomposition, especially under acidic or alkaline conditions.

Safety and Handling

• Hazards:

  • Toxicity: Moderately to highly toxic. Primary hazard stems from the nitrile group, which can metabolically release cyanide ions. It is toxic if swallowed, inhaled, or absorbed through the skin.

  • Irritancy: Causes skin irritation and serious eye damage.

  • Decomposition: Upon heating, contact with strong acids, or under fire conditions, it can decompose to release highly toxic fumes including hydrogen cyanide (HCN) and nitrogen oxides.

  • Flammability: Combustible at high temperatures.

• Precautions & Storage:

  • Personal Protection: Always use in a well-ventilated area or fume hood. Wear appropriate PPE: chemical safety goggles, protective gloves (nitrile/butyl rubber), and protective clothing.

  • Storage: Store in a tightly closed container in a cool, dry, well-ventilated place away from heat, sparks, and open flame. Keep separate from strong oxidizers, acids, and bases.

  • Spill Response: Contain spill with inert absorbent material (e.g., sand, vermiculite). Collect and dispose of as hazardous chemical waste. Avoid using water jets.

  • Fire Fighting: Use dry chemical powder, carbon dioxide, or alcohol-resistant foam. Do not use water jet or acid/base extinguishers.

Product Documents

• Safety Data Sheet (SDS)
• Certificate of Analysis
• Product Brochure
• Technical Data Sheet