2-Methyl-2,4-pentanediol is a colorless liquid with a mild, slightly sweet odor.
2-Methyl-2,4-pentanediol is often used as a solvent in paints, coatings, and cleaning products, and it also serves as an intermediate in the production of chemicals like plasticizers and surfactants.
CAS Number: 5332-73-0
Synonyms:,2-Methylpentane-2,4-diol,2-Methyl-1,3-propanediol,2,4-Pentanediol, 2-methyl-
Introduction
Overview of 2-Methyl-2,4-pentanediol
Definition: 2-Methyl-2,4-pentanediol is a colorless, water-soluble organic compound used primarily as a solvent, plasticizer, and intermediate in the production of various chemicals.
Structure: This diol features a hydroxyl group attached to a pentane backbone with a methyl group at the 2-position, making it a branched-chain alcohol.
Common names: 2-Methylpentanediol, MPD, Methylpentanediol.
Historical Development
Discovery and early applications: Initially recognized in chemical research, MPD has been used for over a century as a solvent and in formulations where its low freezing point and high boiling point are advantageous.
Development of industrial production methods: The chemical has become more widespread in industrial applications following advances in synthesis methods.
Significance in Industry and Research
MPD’s versatility in various industries like pharmaceuticals, cosmetics, paints, coatings, and chemical manufacturing.
Chemical Properties
Molecular Structure
The chemical formula: C6H14O2
The structure consists of a pentane backbone (C5) with hydroxyl groups (-OH) at positions 2 and 4.
Chemical Formula
C6H14O2: Two hydroxyl groups attached to a carbon chain.
Physical Properties
Boiling point: Approximately 191–192°C.
Melting point: -55°C (indicating its liquid state at room temperature).
Density: 0.912 g/cm³ at 25°C.
Refractive index: 1.434.
Flash point: 89°C (relatively high for an alcohol, making it safer to handle).
Solubility: Miscible with water, ethanol, acetone, and many other organic solvents.
Chemical Behavior and Reactivity
MPD is a relatively stable compound and does not readily undergo reactions at ambient conditions.
It can react with strong oxidizing agents, acids, or alkalis, but it is stable under normal storage conditions.
MPD can undergo esterification reactions due to the presence of hydroxyl groups.
Solubility and pH Characteristics
Water-soluble due to the hydroxyl groups.
Neutral pH in its pure form, but its solubility can be affected by the presence of acids or bases.
Synthesis and Production
Methods of Production
Hydroformylation of 2-Methyl-1-butene: A major synthetic route where a hydroformylation reaction is used to convert 2-methyl-1-butene into 2-methylpentanal, which can then be hydrogenated to form MPD.
Hydrogenation of 2,4-Pentanedione: Another process involves the reduction of diketones (such as 2,4-pentanedione) with hydrogen in the presence of a catalyst.
Direct alkylation: A less common method involves the alkylation of alcohols or other compounds.
Raw Materials and Catalysts Used
Raw materials such as 2-methyl-1-butene, hydrogen gas, or other organic intermediates.
Common catalysts: rhodium, cobalt, or other metal-based catalysts in the case of hydroformylation and hydrogenation reactions.
Process Flow Diagrams
Hydroformylation Process: Overview of the process steps including olefin preparation, reaction with CO and H2, and purification stages.
Hydrogenation Process: Process from diketone to final product MPD with intermediates and purification.
Applications
Industrial Uses
Solvent: MPD is widely used as a solvent in industrial applications, including in paints, coatings, and cleaning formulations.
Its excellent solvent properties make it ideal for high-viscosity applications.
Plasticizer: Used in the formulation of plastics and resins, particularly where low volatility is important.
Intermediate in Chemical Manufacturing: MPD is often used as an intermediate for synthesizing other chemicals like esters and other alcohol derivatives.
Biotechnological Applications
Protein crystallization: MPD is used in crystallography studies, particularly in protein crystallization, as it helps in the formation of stable protein crystals.
Cell culture medium: MPD is used in some cell culture mediums for its stabilizing properties.
Other Practical Uses
Antifreeze: Due to its low freezing point, MPD can be used in antifreeze formulations.
Cosmetics and Personal Care Products: As a humectant and solvent in cosmetics, MPD is used in products like lotions, shampoos, and deodorants.
Benefits and Drawbacks
Advantages
Low Volatility: MPD has low vapor pressure, making it safer and more stable for handling than many other alcohols.
Good Solvent Properties: It dissolves a wide range of substances, making it highly versatile.
Low Freezing Point: Its ability to remain liquid in colder environments makes it useful in a variety of applications.
Biodegradability: MPD is biodegradable, making it less harmful to the environment compared to non-biodegradable solvents.
Limitations
Flammability: Though it has a relatively high flash point, MPD is still flammable and requires careful handling.
Limited Chemical Reactivity: While this can be an advantage in some applications, it can limit its use in certain reactions where more reactive solvents are required.
Cost: The production of MPD, particularly through specialized synthesis methods, can be costly, which may limit its use in some industries.
Alternative Compounds
Comparison to Similar Compounds
Propylene Glycol: MPD is often compared to propylene glycol, which is another versatile solvent. MPD offers better solvency power and lower toxicity than propylene glycol in certain applications.
Butylene Glycol: Another alternative often used in cosmetics and industrial formulations, but MPD tends to perform better in high-temperature environments.
Pros and Cons Relative to Alternatives
MPD vs. Isopropyl Alcohol: MPD has a higher boiling point and is less volatile, making it safer for certain uses, but isopropyl alcohol is more widely available and less expensive.
MPD vs. Ethylene Glycol: MPD is less toxic than ethylene glycol, which is a common component in antifreeze and other industrial products.
Future Prospects
Trends in Research and Innovation
There is ongoing research into more sustainable production methods for MPD, with an emphasis on greener catalysts and feedstocks.
Potential future uses in new formulations, especially in biotechnology and the pharmaceutical industries.
Emerging Applications
Growing demand for low-toxicity solvents and plasticizers could drive MPD’s use in environmentally conscious products.
Development of new drug formulations and cosmetic products may further expand MPD's application base.
Regulatory and Market Considerations
Changes in environmental regulations may impact the demand for safer, biodegradable solvents like MPD.
MPD’s market growth is expected to continue as industries focus on sustainability and reducing the use of harmful chemicals.
SAFETY INFORMATION ABOUT 2-METHYL-2,4-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