Cyclopentanone is a cyclic organic compound with the molecular formula C5H8O. It is commonly used as a solvent and as a precursor in the synthesis of various chemicals.
| IUPAC Name | Cyclopentanone |
| Molecular Formula | C5H8O |
| CAS Number | 120-92-3 |
| Synonyms | Ketocyclopentane, CPK, Adipic ketone, Cyclopentanon, Ketopentamethylene, 1-Oxocyclopentane |
| InChI | InChI=1S/C5H8O/c6-5-3-1-2-4-5/h1-4H2 |
Cyclopentanone molar mass
Cyclopentanone has a molar mass of approximately 84.13 g/mol. This value can be calculated by adding up the atomic weights of all the atoms in a single molecule of the compound. In this case, there are five carbon atoms with an atomic weight of 12.01 g/mol each, eight hydrogen atoms with an atomic weight of 1.01 g/mol each, and one oxygen atom with an atomic weight of 16.00 g/mol. Therefore, the total molar mass of cyclopentanone is 5 x 12.01 + 8 x 1.01 + 16.00 = 84.13 g/mol.
Cyclopentanone boiling point
Cyclopentanone has a boiling point of approximately 130-132°C at standard atmospheric pressure (1 atm). The boiling point of a compound is the temperature at which it changes from a liquid to a gas at standard atmospheric pressure. Cyclopentanone has a relatively low boiling point due to its small size and relatively weak intermolecular forces. It is a volatile compound that can easily evaporate at room temperature.
Cyclopentanone melting point
Cyclopentanone has a melting point of approximately -47°C. The melting point of a compound is the temperature at which it changes from a solid to a liquid. Cyclopentanone is a colorless liquid at room temperature and atmospheric pressure, so its melting point is not often relevant. However, it can solidify at low temperatures, and its melting point is useful for determining its purity.
Cyclopentanone density g/ml
Cyclopentanone has a density of approximately 0.96 g/mL at room temperature and standard atmospheric pressure. The density of a compound is the mass of the substance per unit volume. Cyclopentanone has a relatively low density compared to water (1 g/mL) and many other organic solvents. This low density makes it a useful solvent for some applications where a less dense solvent is needed.
Cyclopentanone molecular weight
The molecular weight of cyclopentanone is 84.13 g/mol. Molecular weight is the sum of the atomic weights of all atoms in a molecule. In the case of cyclopentanone, the molecule contains 5 carbon atoms, 8 hydrogen atoms, and 1 oxygen atom. The molecular weight is often used in chemical calculations to determine the amount of a substance needed or produced in a reaction.
Cyclopentanone Structure
Cyclopentanon has a cyclic structure with a five-membered ring of carbon atoms and an oxygen atom. The oxygen atom is part of a carbonyl group (C=O) that gives the compound its characteristic reactivity. The cyclic structure of cyclopentanon makes it a useful starting material for the synthesis of many other organic compounds.
Cyclopentanon formula
The molecular formula of cyclopentanon is C5H8O. This formula indicates the number of atoms of each element in a molecule of the compound. In this case, the formula indicates that there are 5 carbon atoms, 8 hydrogen atoms, and 1 oxygen atom in each molecule of cyclopentanon. The formula is useful for calculating the molecular weight of the compound and for understanding its chemical properties.
| Appearance | Colorless liquid |
| Specific Gravity | 0.960 g/mL at 20°C |
| Color | Colorless |
| Odor | Camphor-like odor |
| Molar Mass | 84.13 g/mol |
| Density | 0.960 g/mL at 20°C |
| Melting Point | -47°C |
| Boiling Point | 130-132°C |
| Flash Point | 38°C (closed cup) |
| Water Solubility | Miscible |
| Solubility | Miscible with most organic solvents |
| Vapor Pressure | 3.3 mmHg at 25°C |
| Vapor Density | 3.0 (air = 1) |
| pKa | 16.7 |
| pH | Not applicable |
Cyclopentanon Safety and Hazards
Cyclopentanon can pose several safety hazards if not handled properly. It is a flammable liquid and can ignite if exposed to a heat source or flame. It can also cause irritation and burns if it comes into contact with the skin or eyes. Inhaling its vapors can cause headache, dizziness, and nausea. It is important to use proper protective equipment such as gloves, goggles, and a lab coat when handling cyclopentanon. It should be stored in a cool, dry place away from heat sources and incompatible materials. Spills should be cleaned up immediately and the area should be well ventilated.
| Hazard Symbols | F, Xi |
| Safety Description | Keep away from sources of ignition – No smoking. Avoid contact with skin and eyes. Wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). |
| UN IDs | UN 2245 |
| HS Code | 291429 |
| Hazard Class | 3 |
| Packing Group | III |
| Toxicity | Cyclopentanon is considered to be a low toxicity substance. However, it can cause irritation to the skin, eyes, and respiratory system. Long-term exposure may cause liver and kidney damage. It is important to handle cyclopentanon with care and follow proper safety protocols. |
Cyclopentanone Synthesis Methods
Cyclopentanon can be synthesized through a variety of methods. One common method is the hydrogenation of phenol, which involves the reaction of phenol with hydrogen gas over a metal catalyst such as palladium. Another method involves the oxidation of cyclopentene using potassium permanganate or ozone gas. This reaction produces cyclopentanon as well as other byproducts such as carboxylic acids.
To synthesize cyclopentanon, one can perform a Diels-Alder reaction between cyclopentadiene and maleic anhydride to form a cyclic intermediate, which can be further hydrolyzed to yield cyclopentanon. Another approach is to subject adipic acid to a decarboxylation reaction in the presence of a dehydrating agent like phosphorus pentoxide. This method also produces cyclopentanon.
Other methods for the synthesis of cyclopentanon include the reaction of cyclopentylmagnesium bromide with carbon dioxide, and the reaction of cyclopentene with carbon monoxide in the presence of a metal catalyst such as cobalt carbonyl.
The choice of synthesis method for cyclopentanon will depend on various factors such as the availability of starting materials, the desired purity of the product, and the desired reaction conditions. It is important to use proper safety protocols and equipment when handling these chemicals.
Cyclopentanone Uses
Cyclopentanon finds use in various applications, making it a versatile chemical.
- It serves as a solvent in the production of chemicals such as fragrances, pesticides, and pharmaceuticals.
- It acts as a precursor in the synthesis of other chemicals, including adipic acid, cyclopentylamine, and cyclopentanol.
- The pharmaceutical industry utilizes cyclopentanon as an intermediate in the production of drugs such as anti-inflammatory agents, antihistamines, and muscle relaxants.
- The food industry uses it as a flavoring agent due to its camphor-like odor.
- Cyclopentanon is also used in the production of polymers like polyester, nylon, and polyurethane, where it imparts properties like durability, flexibility, and resistance to heat and chemicals.
- Organic chemistry reactions like the formation of carbon-carbon bonds and preparation of cyclic compounds use cyclopentanon as a reagent.
- Agricultural chemicals such as insecticides and herbicides utilize cyclopentanon in their manufacture.
In conclusion, cyclopentanon’s versatility makes it a vital chemical in various industries, ranging from pharmaceuticals to agriculture to polymers.
Questions:
Q: What does the IR spectrum of cyclopentanone look like?
A: The IR spectrum of cyclopentanone typically shows a strong carbonyl (C=O) absorption band at around 1715-1740 cm^-1, as well as C-H stretching and bending bands in the range of 2850-3000 cm^-1.
Q: Will cyclohexylamine react with cyclopentanone to form an enamine?
A: Yes, cyclohexylamine can react with cyclopentanone to form an enamine. The reaction involves the protonation of the amine nitrogen by an acid catalyst, followed by the nucleophilic addition of the nitrogen lone pair to the carbonyl group of the cyclopentanone. The resulting product is an enamine, which contains a carbon-carbon double bond between the nitrogen and the alpha-carbon of the cyclopentanone.
Q: How is cyclopentanone industrially produced?
A: Cyclopentanone can be industrially produced through various methods, including the hydrogenation of phenol using a metal catalyst such as palladium, and the oxidation of cyclopentene using potassium permanganate or ozone gas. The choice of method will depend on various factors such as the availability of starting materials, desired purity of the product, and desired reaction conditions. It is important to use proper safety protocols and equipment when handling these chemicals.