Cyclohexanol or C6H11OH is a colorless, oily liquid with a mild odor. It is commonly used as a solvent and in the production of nylon and other chemicals.
| IUPAC Name | Cyclohexanol |
| Molecular Formula | C6H12O or C6H11OH |
| CAS Number | 108-93-0 |
| Synonyms | Hexahydrophenol; Hydrophenol; Cyclohexyl alcohol; Hexalin; Cyclohexanolol |
| Chemical Structure | InChI=1S/C6H12O/c7-6-4-2-1-3-5-6/h6-7H,1-5H2 |
Cyclohexanol Structure
Cyclohexanol has a six-membered carbon ring with a hydroxyl group (-OH) attached to one of the carbon atoms. The molecular formula of cyclohexanol is C6H12O. The cyclohexane ring has a chair conformation with the hydroxyl group located in the axial position. The structure of cyclohexanol is important as it determines its physical and chemical properties.
Cyclohexanol Formula
The chemical formula of cyclohexanol is C6H12O. This represents the number and types of atoms in a molecule of cyclohexanol. The formula is important as it is used to calculate the amount of cyclohexanol needed in a reaction. Additionally, it is used to determine the stoichiometry of a reaction.
Cyclohexanol IR Spectrum
The IR spectrum of cyclohexanol shows a broad, strong peak at around 3400 cm-1 due to the presence of the hydroxyl group (-OH). This peak is indicative of the presence of an alcohol. In addition, the spectrum shows several peaks in the 1000-1300 cm-1 range due to the presence of the cyclohexane ring. The IR spectrum of cyclohexanol is important as it can be used to identify and characterize the substance.
Cyclohexanol Molar Mass
Summing the atomic masses of all atoms in a molecule of cyclohexanol calculates its molar mass, which is 100.16 g/mol. The molar mass plays a crucial role in determining the amount of cyclohexanol required in a reaction and converting between grams and moles in stoichiometric calculations.
Cyclohexanol Boiling Point
The boiling point of cyclohexanol is 161.5°C (322.7°F). This is the temperature at which the liquid phase of cyclohexanol changes to a gaseous phase. The boiling point is an important physical property as it is used to purify and separate cyclohexanol from other substances in a mixture. The relatively high boiling point of cyclohexanol makes it useful as a solvent in reactions that require high temperatures.
C6H11OH Melting Point
C6H11OH has a melting point of 25.93°C (78.67°F). This is the temperature at which the solid phase of C6H11OH changes to a liquid phase. The melting point is an important physical property as it is used to identify and characterize C6H11OH. It is also used to determine the purity of C6H11OH.
C6H11OH Density g/mL
C6H11OH has a density of 0.962 g/mL at 25°C (77°F). This is the mass of C6H11OH per unit volume of the substance. The density is an important physical property as it is used to determine the mass of C6H11OH needed in a reaction. Additionally, it is used to calculate the concentration of C6H11OH in a solution.
C6H11OH Molecular Weight
C6H11OH has a molecular weight of 100.16 g/mol. This is the sum of the atomic weights of all atoms in a molecule of C6H11OH. The molecular weight is an important property as it is used to calculate the amount of C6H11OH needed in a reaction. Additionally, it is used to convert between grams and moles in stoichiometric calculations.
| Appearance | Colorless liquid |
| Specific Gravity | 0.962 g/mL |
| Color | Colorless |
| Odor | Mild odor |
| Molar Mass | 100.16 g/mol |
| Density | 0.962 g/mL |
| Melting Point | 25.93°C (78.67°F) |
| Boiling Point | 161.5°C (322.7°F) |
| Flash Point | 70°C (158°F) |
| Water Solubility | Miscible |
| Solubility | Soluble in many organic solvents |
| Vapor Pressure | 0.14 kPa (at 25°C) |
| Vapor Density | 3.5 (air = 1) |
| pKa | 16.1 |
| pH | 6 to 8 |
Note: The values presented in this table are approximate and may vary depending on the source of information.
Cyclohexanol Safety and Hazards
C6H11OH should be handled with caution as it poses certain safety risks and hazards. Exposure to this chemical can cause irritation of the skin, eyes, and respiratory system. It may also cause headache, dizziness, and nausea if inhaled. Ingestion of C6H11OH can lead to abdominal pain, vomiting, and diarrhea. This chemical is flammable and can ignite when exposed to heat or flames. It is important to store and handle it in a cool, dry place away from heat and sources of ignition. Protective equipment such as gloves, goggles, and respiratory masks should be used when handling C6H11OH. In case of exposure, seek medical attention immediately.
| Hazard Symbols | Xi |
| Safety Description | S26 – In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.<br> S36/37/39 – Wear suitable protective clothing, gloves and eye/face protection.<br>S45 – In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). |
| UN Ids | UN1986 |
| HS Code | 2907.13.00 |
| Hazard Class | 3 |
| Packing Group | III |
| Toxicity | Low to moderate toxicity |
Cyclohexanol Synthesis methods
C6H11OH can be synthesized through several methods.
- A common method to produce C6H11OH is through the catalytic hydrogenation of phenol in the presence of a metal catalyst such as nickel or platinum. This method involves reducing the aromatic ring of phenol to form C6H11OH.
- Another method involves the oxidation of cyclohexane using air or oxygen in the presence of a catalyst such as copper or cobalt. This process produces C6H11OH as an intermediate product that can be further oxidized to form cyclohexanone.
- C6H11OH can also be obtained through the hydrolysis of cyclohexyl acetate using an acid or base catalyst. This method involves cleaving the ester bond in cyclohexyl acetate to form C6H11OH and acetic acid.
- The Beckmann rearrangement of cyclohexanone oxime using sulfuric acid as a catalyst is another method to synthesize C6H11OH. This process involves rearranging the oxime group in cyclohexanone oxime to form an amide intermediate, which can be hydrolyzed to produce C6H11OH.
Overall, conducting the synthesis of C6H11OH requires individuals to perform various chemical processes and utilize appropriate safety precautions and equipment.
Cyclohexanol Uses
C6H11OH has a variety of applications in different industries.
- Industries use C6H11OH as a solvent to produce lacquers, varnishes, and resins, and also as a solvent to prepare medications in the pharmaceutical industry.
- C6H11OH serves as a significant intermediate in the production of adipic acid, which is a necessary component in making nylon. It also acts as a starting material for the synthesis of various chemicals, including bisphenol A, cyclohexanone, and caprolactam.
- The petroleum industry adds C6H11OH as a corrosion inhibitor to crude oil to prevent corrosion in pipelines and storage tanks.
- Manufacturers use C6H11OH to produce plasticizers that enhance the flexibility and durability of plastics. It is also a common ingredient in perfumes and cosmetics.
- C6H11OH serves as a heat transfer fluid, a lubricant, and a pesticide. Additionally, it serves as a reagent in organic synthesis and laboratory experiments.
Overall, C6H11OH has a diverse range of applications in various industries and its versatile properties make it an important chemical in many industrial processes.
Questions:
Is cyclohexanol soluble in water?
Cyclohexanol is moderately soluble in water, but its solubility decreases as the temperature increases. It is more soluble in organic solvents such as ethanol, diethyl ether, and acetone. The solubility of C6H11OH in water is due to the formation of hydrogen bonds between the hydroxyl group of C6H11OH and water molecules. However, the hydrophobic cyclohexane ring in C6H11OH reduces its overall polarity, making it less soluble in water than other more polar alcohols such as methanol and ethanol. The solubility of C6H11OH in water is an important consideration in its use as a solvent and in industrial processes that involve water as a medium.
Which of the following series of reactions would convert cyclohexanol to 1,2-epoxycyclohexane?
To convert cyclohexanol to 1,2-epoxycyclohexane, the following series of reactions can be carried out:
- Cyclohexanol is first treated with a strong acid catalyst such as sulfuric acid to form cyclohexene through dehydration.
- The resulting cyclohexene is then reacted with a peracid such as m-chloroperbenzoic acid (MCPBA) to form an epoxide, specifically 1,2-epoxycyclohexane.
Therefore, the correct series of reactions to convert cyclohexanol to 1,2-epoxycyclohexane involves dehydration of cyclohexanol to form cyclohexene followed by epoxidation of cyclohexene to form 1,2-epoxycyclohexane using a peracid.
Why does cyclohexanol not need a numerical prefix?
Cyclohexanol does not need a numerical prefix in its name because it is a single isomer of cyclohexanol. Isomers are molecules with the same molecular formula but with different structural arrangements of atoms. Cyclohexanol has a single hydroxyl (-OH) functional group attached to a cyclohexane ring, and its molecular formula is C6H12O. Since there is only one possible arrangement of the atoms in cyclohexanol, it does not require a numerical prefix to specify its position or number of functional groups. In contrast, other compounds such as cyclohexanone and cyclohexanedione have multiple isomers with different positions and numbers of carbonyl groups and thus require numerical prefixes to specify the location of the functional groups.