CYCLOHEXANONE

Cyclohexanone is a colorless, flammable liquid with a sweet odor, often used as an industrial solvent. 
Cyclohexanone is a key intermediate in the production of nylon and other synthetic fibers. 
Cyclohexanone can also be used in paint removers, lacquers, and coatings due to its solvent properties.
 
Cas Number
108-94-1

Synonyms
2-Cyclohexen-1-one,Cyclohexanon,Hexan-2-one,1-Cyclohexen-2-one,2-Oxo-cyclohexane
 
Introduction
Definition and Overview of Cyclohexanone:
Cyclohexanone (C₆H₁₀O) is a cyclic ketone with a six-membered ring structure containing a single carbonyl group. 
It is commonly used as an industrial solvent and a precursor to various chemical products.
It is an important intermediate in the manufacture of nylon, specifically Nylon 6, and is utilized in the synthesis of many other chemicals and products.
 
Historical Background and Discovery:
Cyclohexanone was first synthesized in 1867 by the German chemist August Wilhelm von Hofmann by the oxidation of cyclohexane, a compound found in oil and petroleum products.
The commercial-scale production of Cyclohexanone began in the early 20th century and has grown significantly, especially with its role in nylon production post-World War II.
 
Significance in Industry and Research:
Cyclohexanone plays a vital role in the chemical industry due to its reactivity and versatility, serving as a solvent, intermediate, and reactant in various reactions, including the synthesis of polyamides, fragrances, and pharmaceuticals.
 
Chemical Properties
Chemical Structure and Molecular Formula:
The molecular formula of Cyclohexanone is C₆H₁₀O, and it has a structure consisting of a six-membered carbon chain with one oxygen atom double-bonded to a carbon atom (carbonyl group).
 
The carbonyl group imparts reactivity to Cyclohexanone, making it a suitable compound for nucleophilic attacks and other organic reactions.
 
Physical Properties:
Boiling Point: 155.6°C (312.1°F)
Melting Point: -31.3°C (-24.3°F)
Density: 0.947 g/cm³ (at 20°C)
Solubility: Soluble in water (though limited), soluble in many organic solvents like ethanol, acetone, and ether.
Appearance: Colorless liquid with a sweet, slightly fruity odor. It is volatile and has a low vapor pressure.
 
Chemical Reactivity and Stability:
Cyclohexanone is stable under normal conditions but can undergo oxidation to form cyclohexanol and other byproducts in the presence of oxidizing agents.
It can also undergo nucleophilic additions, such as in aldol condensations, due to the electrophilic nature of the carbonyl carbon.
Functional Groups and Bonding Characteristics:
The carbonyl group (C=O) in Cyclohexanone is the primary functional group, making it reactive towards nucleophilic addition reactions.
The structure allows it to act as a donor in hydrogen bonding with other polar molecules.
 
Production Methods
Methods of Industrial Production:
Oxidation of Cyclohexane: Cyclohexanone is primarily produced by the oxidation of cyclohexane, a reaction typically carried out using oxygen and a catalyst such as cobalt or manganese-based compounds.
Dehydrogenation of Cyclohexanol: Another method involves the dehydrogenation of cyclohexanol in the presence of a catalyst like copper or zinc.
 
Raw Materials Used in Production:
The main raw material is cyclohexane, which is derived from petroleum or natural gas.
Other feedstocks include hydrogen and oxygen, which participate in oxidation and dehydrogenation reactions.
 
Key Processes:
In the oxidation process, cyclohexane is reacted with air or oxygen under high pressure and temperature, often using a catalyst.
The dehydrogenation process involves heating cyclohexanol to induce the removal of hydrogen atoms, forming cyclohexanone.
 
Technological Advancements in Production:
Recent advancements have focused on improving the selectivity of catalysts to increase the yield of cyclohexanone and minimize the formation of unwanted byproducts.
Biotechnological methods are being explored to produce cyclohexanone using engineered microorganisms for greener and more sustainable production.
 
Applications
Use in Nylon Production:
Cyclohexanone is a crucial intermediate in the production of Nylon 6, a widely used synthetic polymer.
 It is converted to caprolactam, the monomer for Nylon 6, through a series of chemical reactions.
 
Role as a Solvent:
Cyclohexanone is widely used as a solvent in industrial coatings, paints, varnishes, and adhesives. 
Its ability to dissolve a variety of resins and polymers makes it valuable in these industries.
Involvement in Coatings, Adhesives, and Paints:
It is often used in formulations for surface coatings, as it enhances the application properties and drying times of paint and lacquer formulations.
 
Applications in Organic Synthesis:
 
Cyclohexanone is used as a building block in organic synthesis, including the preparation of various chemicals such as pharmaceuticals, agrochemicals, and fragrances.
 
Environmental and Pharmaceutical Applications:
 
Cyclohexanone is used in small quantities for specific pharmaceutical applications and in the production of chemicals with significant environmental benefits, such as biodegradable solvents.
 
Mechanism of Reactions Involving Cyclohexanone
Reactions with Nucleophiles and Electrophiles:
Cyclohexanone undergoes nucleophilic addition reactions due to the electrophilic nature of the carbonyl carbon.
 Examples include reactions with Grignard reagents, alcohols, and amines to form various adducts.
It can also react with electrophiles like halogens in certain conditions.
Role in Aldol Condensation Reactions:
 
Cyclohexanone is a common reactant in aldol condensation reactions, where it reacts with aldehydes or ketones in the presence of a base to form β-hydroxy ketones or α,β-unsaturated carbonyl compounds.
 
Reduction Reactions and Their Significance:
Cyclohexanone is easily reduced to cyclohexanol by reducing agents such as sodium borohydride or hydrogen in the presence of a catalyst.
This reduction process is important in the production of polyols, which have applications in synthetic polymers and surfactants.
 
Advancements and Innovations
Research on New Catalytic Processes:
Researchers are focusing on developing more efficient catalysts for the production of Cyclohexanone, aiming for reduced energy consumption and waste production.
 
Green Chemistry Initiatives:
The shift toward more sustainable production methods includes using renewable raw materials and reducing the environmental impact of chemical processes.
 
Biotechnology and Biocatalysis in Cyclohexanone Synthesis:
The use of genetically engineered microorganisms for the biosynthesis of Cyclohexanone represents a growing field, offering a more sustainable production route.
 
Alternative Methods and Substitutes
Comparison with Other Solvents:
Cyclohexanone is compared to other solvents like toluene, acetone, and methyl ethyl ketone in terms of efficacy, safety, and environmental impact.
 
Research into Bio-Based Substitutes:
Studies into bio-based alternatives to Cyclohexanone include the exploration of renewable feedstocks like biomass-derived chemicals and bioprocesses for synthesis.
 
Challenges and Benefits of Alternatives:
While bio-based substitutes offer environmental benefits, challenges such as scalability and cost remain in their widespread adoption.
 
Conclusion
Summary of Cyclohexanone's Significance:
Cyclohexanone is a versatile compound with crucial roles in the chemical and industrial sectors, particularly in the production of nylon and as a solvent.
 
Its Future Prospects in Industry and Research:
Continued innovation in production methods, environmental impact mitigation, and applications in green chemistry will ensure Cyclohexanone remains a key compound in various industries.
 
Recommendations for Sustainable Usage and Production:
The adoption of more efficient, sustainable production processes and better waste management practices will help reduce Cyclohexanone’s environmental footprint while maintaining its industrial importance.

SAFETY INFORMATION ABOUT CYCLOHEXANONE
 
 
 
 
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