3-Amino-1-propanol
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Product Description
3-Aminopropanol is a colorless, hygroscopic, viscous liquid that combines a primary amino group and a terminal hydroxyl group on a three-carbon chain, giving it dual alcohol/amine reactivity; it is miscible with water and polar solvents, boils at 187–188 °C, is corrosive and combustible, and is manufactured industrially by Raney-Ni-catalysed hydrogenation of β-hydroxypropionitrile. This C3 building block serves as a key intermediate for pharmaceuticals (cyclophosphamide, beta-blockers, chloroquine), the vitamin B5 precursor DL-panthenol, agrochemicals, surfactants, dyes, epoxy/PU curing agents and polyamide modifiers, and must be stored under nitrogen away from oxidants and moisture.
3-Amino-1-propanol is classified as an important fine chemical intermediate. Academic research provides detailed insights into its role in molecular interactions within binary liquid systems (relevant for industrial gas absorption and CO2 capture) and its utility in novel chemical recycling processes, such as the depolymerization of plastics. Its fundamental value lies in serving as a C3 structural unit that bridges amine and alcohol chemistry.
Synthesis and Production
The predominant industrial synthesis method is the catalytic hydrogenation of β-hydroxypropionitrile (hydroxypropionitrile). The process typically involves reacting hydroxypropionitrile with hydrogen under pressure (e.g., ~3 MPa) in the presence of a catalyst like Raney nickel and ammonia, at elevated temperatures (100–120 °C). Following the reaction, the mixture undergoes filtration to recover the catalyst, followed by distillation (often under reduced pressure, e.g., 90–92 °C/2 kPa) to obtain the purified product with a typical yield around 70% and purity ≥95%. Further purification steps, including the removal of water, ammonia, and by-products, are required to achieve high-purity grades (e.g., ≥99% for cosmetic applications).
Uses and Applications
3-Amino-1-propanol is a versatile bifunctional intermediate with applications across several key industries due to its dual reactivity.
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Pharmaceuticals: It is a crucial building block for synthesizing various active pharmaceutical ingredients (APIs), including anticancer drugs (e.g., cyclophosphamide), cardiovascular agents (e.g., beta-blockers like propranolol analogues, prenylamine), antimalarials (e.g., chloroquine), local anesthetics, and antidepressants.
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Cosmetics and Personal Care: It serves as a key raw material for the synthesis of DL-panthenol (provitamin B5) and its derivatives, which are widely used in skincare and haircare products for their moisturizing and reparative properties.
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Polymer and Materials Industry: It is used as a monomer or modifier in the production of polyamides, polyurethanes, and epoxy curing agents, where it can improve flexibility, adhesion, and chemical stability. It also acts as a precursor for synthesizing morpholine derivatives.
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Surfactants and Specialty Chemicals: Its structure is utilized to produce amphoteric surfactants, quaternary ammonium compounds, emulsifiers, and corrosion inhibitors for use in detergents, textiles, and metal treatment.
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Chemical Synthesis and Research: It functions as a solvent, catalyst, or general-purpose building block in organic synthesis for dyes, rubber additives, and chelating agents (e.g., EDTA analogues). Recent research also explores its role in chemical processes like the depolymerization of PET plastics and in CO2 capture mechanisms.
Chemical and Physical Properties
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Physical Form: Colorless to pale yellow, viscous, hygroscopic liquid with a mild amine-like odor.
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Molecular Data: Chemical formula C₃H₉NO, MW ~75.11 g/mol, CAS No. 156-87-6. Common synonyms include 3-aminopropanol and γ-aminopropyl alcohol.
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Key Physical Constants: Melting point ~ -15 to 12 °C; Boiling point ~ 187-190 °C; Density ~ 0.982-1.01 g/cm³; Refractive index ~1.4617; Flash point ~79 °C.
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Solubility: Miscible with water, alcohols (ethanol), and other polar solvents like acetone, ether, and chloroform.
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Chemical Properties: It contains both a primary amine (-NH₂) and a primary alcohol (-OH) group, making it a bifunctional molecule. The amino group confers basicity (pKa ~9.7), allowing salt formation with acids. It can undergo typical reactions of both amines (alkylation, acylation, amide formation) and alcohols (esterification, etherification). Its physicochemical behavior in mixtures, such as viscosity and volume changes, is influenced by molecular interactions and hydrogen bonding.
Safety and Handling
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Hazards: It is corrosive and causes severe skin burns and eye damage. It is also harmful if swallowed or inhaled and is irritating to the respiratory tract. It is a flammable liquid.
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Precautions: Handling requires adequate ventilation, chemical-resistant gloves, safety goggles, and protective clothing. Avoid contact with skin, eyes, and clothing.
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Storage and Transport: Store in a tightly sealed container under a nitrogen atmosphere in a cool, dry, well-ventilated place away from heat and ignition sources. Keep separated from strong oxidizers and strong acids. Transport classification is typically UN 2735 (corrosive liquids, n.o.s., Class 8).
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Environmental: May be harmful to aquatic life. Spills should be contained and disposed of in accordance with local regulations.