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Introduction
3-Propoxypropylamine is an organic compound belonging to the class of aliphatic amines with an ether functional group.
It is characterized by a propylamine moiety linked through an ether bond to another propyl group, making it a versatile molecule with both nucleophilic amine and hydrophobic ether characteristics.
The presence of a primary amine (-NH2) imparts basicity and reactivity toward electrophiles, making it valuable in multiple industrial and chemical synthesis processes.
Chemical Identification and Nomenclature
IUPAC Name: 3-Propoxypropylamine
CAS Number: 928-55-0
Molecular Formula: C6H15NO
Molecular Weight: 117.19 g/mol
Synonyms and Trade Names
3-Propoxypropylamine is known by several synonyms depending on the supplier or industrial application:
3-(Propoxy)propylamine
1-Aminopropan-3-yloxypropane
3-Aminopropyl propyl ether
PPA (abbreviation used in epoxy chemistry)
N-propyl-3-aminopropyl ether
These synonyms are important to recognize when sourcing or researching the compound in chemical databases and literature.
Historical Development
The compound’s initial synthesis and use date back to mid-20th century advances in epoxy resin chemistry, where amine curing agents were developed to optimize polymer properties such as flexibility, adhesion, and chemical resistance.
The inclusion of an ether linkage in 3-Propoxypropylamine improved compatibility with epoxy networks, fostering its adoption in coatings, adhesives, and sealants.
Chemical Structure and Properties
Molecular Structure
3-Propoxypropylamine’s molecular structure can be described as:
A primary amine group (-NH2) attached at one end of a three-carbon chain (propyl group).
The other end of the molecule contains an ether linkage (-O-) connecting the propylamine chain to another propyl group.
The structure can be represented as:
CH3–CH2–CH2–O–CH2–CH2–CH2–NH2
This gives the molecule both a nucleophilic amine site and an ether oxygen that influences polarity and solubility.
Physical Properties
Property Value Notes
Appearance Colorless to pale yellow liquid Varies by purity
Molecular Weight 117.19 g/mol Calculated
Boiling Point 177–180 °C at 760 mmHg Depends on purity
Melting Point < 0 °C Usually liquid at room temp
Density 0.86 g/mL at 25 °C Less dense than water
Refractive Index ~1.420 Typical for ethers
Solubility Miscible with water, alcohols Due to amine and ether groups
Vapor Pressure Low at room temp Limits volatility
Flash Point ~70 °C (closed cup) Flammable liquid
Chemical Properties
Basicity: The primary amine has a pKa of approximately 9.6, making it a moderately strong base among aliphatic amines.
It readily accepts protons in aqueous solutions.
Nucleophilicity: The lone pair on nitrogen allows the molecule to react with electrophiles such as alkyl halides, isocyanates, and epoxides.
Stability: The ether linkage is generally stable under neutral to mildly basic conditions but can be cleaved under strongly acidic or oxidative environments.
Reactivity: Primary amines are prone to oxidation and can form imines or amides upon reaction with aldehydes or acid derivatives.
Synthesis
Overview of Synthetic Routes
The synthesis of 3-Propoxypropylamine involves introducing an amine group onto a propoxy-functionalized propyl chain.
The typical strategy uses ether formation followed by amination or direct epoxide ring opening with an amine nucleophile.
Method 1: Etherification Followed by Amination
Step 1: Etherification
1,3-Propanediol is reacted with 1-bromopropane (or propyl chloride) under basic conditions (using KOH or NaH) to form 3-propoxy-1-propanol.
This Williamson ether synthesis involves nucleophilic substitution of the alkoxide on the alkyl halide.
Step 2: Conversion to Amine
The hydroxyl group in 3-propoxy-1-propanol is converted to a leaving group (e.g., tosylate or mesylate) and then displaced by ammonia or another amine source, yielding 3-propoxypropylamine.
Reaction summary:
HO–CH2–CH2–CH2–O–CH2–CH2–CH3 → HO–CH2–CH2–CH2–O–CH2–CH2–CH3 (etherification) → NH2–CH2–CH2–CH2–O–CH2–CH2–CH3 (amination)
Method 2: Epoxide Ring Opening
Propylene oxide (an epoxide) can be ring-opened by propylamine under acidic or neutral catalysis to produce 3-Propoxypropylamine in one step.
The nucleophilic attack of the amine on the less hindered carbon of the epoxide ring leads to selective formation.
Industrial Considerations
Purity control is critical, as unreacted epoxides or alkyl halides can affect product quality.
Reaction temperature and solvent choice impact yield and side product formation.
Post-reaction purification often involves distillation under reduced pressure.
Spectroscopic Characterization
Infrared (IR) Spectroscopy
Key absorbance bands for 3-Propoxypropylamine include:
~3300 cm⁻¹: N–H stretching vibrations (primary amine)
~2800–3000 cm⁻¹: C–H stretching of alkyl groups
~1100 cm⁻¹: C–O–C ether stretching
~1600 cm⁻¹: N–H bending vibrations
These bands confirm the presence of both amine and ether functional groups.
Nuclear Magnetic Resonance (NMR) Spectroscopy
¹H NMR:
Triplets and multiplets around 0.9–1.5 ppm correspond to methyl and methylene protons on the propyl chains.
Signals around 2.5–3.3 ppm correspond to methylene groups adjacent to the nitrogen (CH2–NH2) and oxygen (CH2–O).
Broad singlet near 1.5–2.0 ppm indicates exchangeable protons of the amine.
¹³C NMR:
Signals at 10–40 ppm correspond to alkyl carbons.
Signals around 60 ppm indicate carbons adjacent to oxygen.
Mass Spectrometry (MS)
Molecular ion peak at m/z 117 confirms the molecular weight.
Fragmentation patterns include loss of alkyl groups and amine-related fragments.
Reactivity and Stability
General Chemical Reactivity
The primary amine group allows 3-Propoxypropylamine to undergo:
Nucleophilic substitution: With alkyl halides to form secondary and tertiary amines.
Condensation reactions: With aldehydes and ketones forming imines and Schiff bases.
Addition to epoxides: Leading to β-hydroxyamines important in polymer synthesis.
Reaction with isocyanates: Producing urea linkages for polyurethane chemistry.
The ether linkage provides some steric and electronic influence, reducing volatility and modifying hydrophobicity.
Stability
3-Propoxypropylamine is:
Stable under normal storage conditions, protected from moisture and strong oxidizers.
Sensitive to acids, which can hydrolyze the ether bond.
Easily oxidized in presence of oxygen to form nitroso or nitro derivatives (rare in commercial conditions).
SAFETY INFORMATION ABOUT 3-PROPOXYPROPYLAMINE
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
