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1,5-Pentanediol is a colorless, odorless, and hygroscopic liquid at room temperature.
1,5-Pentanediol is soluble in water and many organic solvents.
This diol is commonly used as a building block in polymer synthesis, especially polyesters and polyurethanes, as well as a humectant, solvent, and plasticizer in cosmetics, personal care products, and industrial applications.
CAS Number:
111-29-5
Synonyms:
Pentane-1,5-diol,1,5-Dihydroxypentane,Pentamethylene glycol,NSC 407102
Introduction
Definition
1,5-Pentanediol (C5H12O2) is a diol (a chemical compound with two hydroxyl groups, -OH).
It is commonly used in industrial applications, primarily in the synthesis of polyesters, polyurethanes, and as a plasticizer in polymers.
It has a five-carbon backbone, with hydroxyl groups at positions 1 and 5 in its structure.
The compound is considered to have excellent solubility properties, making it valuable in various applications like solvents, personal care formulations, and chemical intermediates.
Historical Development
The chemical was first synthesized in the early 20th century but gained widespread importance in the 1950s as an intermediate in the production of plastics and resins.
Over the years, its uses expanded, especially as green chemistry approaches and bio-based production methods began to emerge.
Initially, 1,5-pentanediol was synthesized using petrochemical routes, but more recently, biotechnological and enzymatic methods have been developed, allowing for more sustainable production.
Market Overview
The global demand for 1,5-pentanediol continues to grow, driven by the increasing use of polyesters in the automotive, textile, and electronics industries.
It is also seeing more demand in the cosmetic and pharmaceutical sectors, where it is used in formulations.
As the focus shifts to more sustainable and eco-friendly chemicals, the market for bio-based 1,5-pentanediol is expected to rise.
Chemical Properties
Molecular Structure
1,5-Pentanediol has the molecular formula C5H12O2, with two hydroxyl groups (-OH) attached to the first and fifth carbon atoms in the chain.
The structure can be represented as:
It is a linear diol, with each hydroxyl group located at the ends of the five-carbon chain.
This structure gives it its unique properties, such as the ability to form strong hydrogen bonds, which contributes to its solubility and reactivity.
Physical Properties
Boiling Point: 210°C
Melting Point: 23-26°C
Density: 1.03 g/cm³ at 20°C
Solubility: It is highly soluble in water, alcohol, and acetone, and has moderate solubility in oils and fats.
Viscosity: 5.52 cP at 20°C.
Flash Point: 95°C (closed cup).
Refractive Index: 1.465.
These physical properties make it ideal for use in a variety of applications, from solvents to plasticizers, and ensure its effectiveness in chemical syntheses.
Chemical Behavior
1,5-Pentanediol contains two hydroxyl groups, which make it reactive with various chemicals. It can undergo:
Esterification: Reacts with carboxylic acids to form esters, which are important in polymer production.
Oxidation: Can be oxidized to produce ketones or aldehydes under certain conditions.
Hydrogen Bonding: Due to the hydroxyl groups, it can form strong hydrogen bonds with other molecules, increasing its solubility and stability in certain environments.
Spectroscopic Data
NMR (Nuclear Magnetic Resonance): ^1H-NMR and ^13C-NMR spectra of 1,5-pentanediol confirm its structure. The ^1H-NMR typically shows signals for the protons of the two hydroxyl groups and the -CH2-CH2-CH2- chain.
IR (Infrared) Spectroscopy: The presence of hydroxyl groups is indicated by strong O-H stretch bands around 3300 cm^-1. The CH2 and CH2OH bending and stretching vibrations are also visible.
Production Methods
Raw Materials
The primary raw materials for the industrial synthesis of 1,5-pentanediol are petrochemical-based compounds, such as:
Succinic acid: This is one of the starting materials used in biotechnological and green chemistry routes.
Butadiene: In certain processes, butadiene undergoes hydrogenation to form 1,5-pentanediol.
Renewable sources: In emerging biotechnological methods, glucose or glycerol derived from renewable resources are used.
Synthesis Routes
Hydrogenation of Butadiene: Butadiene is hydrogenated to form 1,5-pentanediol via a catalytic process.
This process is typically carried out under high pressure and temperature in the presence of a metal catalyst, such as palladium or nickel.
Reduction of Succinic Acid: Succinic acid can be reduced to 1,5-pentanediol using hydrogenation or catalytic reduction.
Biotechnological Methods: The fermentative production of 1,5-pentanediol from glucose or glycerol using microorganisms is an emerging field.
This process is considered more sustainable, as it avoids reliance on fossil fuels.
Process Design
Industrial production typically uses continuous flow reactors and pressure vessels for hydrogenation. The process is optimized for high yield and minimal by-product formation.
Energy requirements depend on the feedstock used and the method of synthesis, with biotechnological processes generally being more energy-efficient.
Recent Advances
Green Chemistry: New methods focus on reducing the environmental impact, such as the use of biocatalysts for more selective reactions.
Waste Reduction: Advances in catalyst design and reaction conditions aim to minimize waste products and improve sustainability.
Applications
Polymer Industry
1,5-Pentanediol is used extensively in the production of polyesters and polyurethanes.
In polyesters, it provides flexibility and thermal stability, making it valuable in the automotive and textile industries.
Polyurethanes made from 1,5-pentanediol are used in coatings, foams, and adhesives.
Cosmetics & Personal Care
Humectant: 1,5-Pentanediol is used in creams, lotions, and serums as a humectant that retains moisture, improving skin hydration.
Solvent: It serves as a solvent for active ingredients in cosmetic formulations.
Solvents & Plasticizers
1,5-Pentanediol is used as a solvent in paints, coatings, and inks due to its good solvency and low volatility.
It also acts as a plasticizer in polymers, improving flexibility and reducing brittleness.
Pharmaceuticals
In the pharmaceutical industry, 1,5-pentanediol is used as a solvent or stabilizer in drug formulations, particularly in injectables and topical treatments.
Other Uses
1,5-Pentanediol is used in agriculture as a stabilizer for pesticides and herbicides, and in electronics for making circuit boards and other materials that require a durable, flexible plastic.
SAFETY INFORMATION ABOUT 1,5-PENTANEDIOL
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
