Allyl alcohol (C3H6O) is a colorless liquid with a pungent odor. It is used in the production of resins, plasticizers, and pharmaceuticals. It can cause irritation to the skin and eyes.
| IUPAC Name | Prop-2-en-1-ol |
| Molecular Formula | C3H6O |
| CAS Number | 107-18-6 |
| Synonyms | 2-Propen-1-ol; Vinylcarbinol; 2-Propenol; Propyleneol |
| InChI | InChI=1S/C3H6O/c1-2-3-4/h2,4H,1,3H2 |
Allyl Alcohol Properties
Allyl Alcohol Formula
The formula of allyl alcohol is C3H6O. It consists of three carbon atoms (C3), six hydrogen atoms (H6), and one oxygen atom (O). This chemical formula represents the composition and arrangement of atoms in a molecule of allyl alcohol.
Allyl Alcohol Molar Mass
The molar mass of vinylcarbinol is calculated by adding up the atomic masses of its constituent elements. Carbon has an atomic mass of approximately 12.01 g/mol, hydrogen has an atomic mass of around 1.01 g/mol, and oxygen has an atomic mass of about 16.00 g/mol. Adding these values together gives the molar mass of vinylcarbinol as approximately 58.08 g/mol.
Allyl Alcohol Boiling Point
Vinylcarbinol has a boiling point of around 97.2 degrees Celsius (207 degrees Fahrenheit). This is the temperature at which the liquid form of vinylcarbinol changes into a gaseous state. The boiling point is influenced by intermolecular forces and molecular structure.
Allyl Alcohol Melting Point
The melting point of vinylcarbinol is approximately -129 degrees Celsius (-200 degrees Fahrenheit). This is the temperature at which the solid form of vinylcarbinol transforms into a liquid state. The melting point is determined by the strength of intermolecular forces and the arrangement of molecules.
Allyl Alcohol Density g/mL
The density of vinylcarbinol is typically around 0.854 g/mL at 20 degrees Celsius (68 degrees Fahrenheit). Density is the measure of mass per unit volume, indicating how tightly packed the molecules are within a substance.
Allyl Alcohol Molecular Weight
The molecular weight of vinylcarbinol is approximately 58.08 grams per mole (g/mol). It is calculated by summing up the atomic weights of all the atoms in the molecule based on its chemical formula.
Allyl Alcohol Structure
Vinylcarbinol has a molecular structure consisting of a three-carbon chain (propene) with a hydroxyl (-OH) group attached to one of the carbon atoms. This arrangement gives vinylcarbinol its unique chemical properties and reactivity.
Allyl Alcohol Solubility
Vinylcarbinol is soluble in water to some extent. It forms hydrogen bonds with water molecules due to the presence of the hydroxyl group. However, its solubility decreases as the temperature rises. Vinylcarbinol is more soluble in polar solvents and organic solvents such as ethanol and acetone.
| Appearance | Colorless liquid |
| Specific Gravity | 0.854 g/mL |
| Color | N/A |
| Odor | Pungent |
| Molar Mass | 58.08 g/mol |
| Density | 0.854 g/mL |
| Melting Point | -129°C (-200°F) |
| Boiling Point | 97.2°C (207°F) |
| Flash Point | 27.8°C (82°F) |
| Water Solubility | Miscible |
| Solubility | Soluble in polar solvents |
| Vapor Pressure | 22 mmHg at 20°C |
| Vapor Density | 2.0 (air = 1) |
| pKa | 15.4 |
| pH | 6.5-8.5 |
Allyl Alcohol Safety and Hazards
Vinylcarbinol poses certain safety hazards and should be handled with caution. It can cause irritation to the skin, eyes, and respiratory system upon direct contact or inhalation. Prolonged or repeated exposure may lead to dermatitis. Ingestion of vinylcarbinol can result in nausea, vomiting, and abdominal pain. It is flammable and can form explosive mixtures with air. Therefore, proper ventilation and fire safety measures are essential during its storage and handling. Personal protective equipment, such as gloves and goggles, should be used when working with vinylcarbinol to minimize the risk of exposure.
| Hazard Symbols | Corrosive, Flammable |
| Safety Description | – Causes severe skin burns and eye damage – Highly flammable liquid and vapor |
| UN IDs | UN 1098 |
| HS Code | 2905.13.00 |
| Hazard Class | Class 6.1 (Toxic substances) <br> Class 3 (Flammable liquids) |
| Packing Group | PG II |
| Toxicity | Toxic if swallowed, inhaled, or absorbed through the skin. Can cause serious health effects. |
Allyl Alcohol Synthesis Methods
Vinylcarbinol synthesis involves several methods. One commonly used approach is the catalytic hydration of propylene, where propylene reacts with water in the presence of sulfuric acid or phosphoric acid catalysts. Controlled temperature and pressure conditions facilitate the formation of vinylcarbinol.
Another method entails the hydrolysis of allyl chloride or allyl acetate. Treating allyl chloride with water and a base like sodium hydroxide or potassium hydroxide yields vinylcarbinol and the corresponding chloride salt. Similarly, hydrolyzing allyl acetate with water and a strong base result in the production of vinylcarbinol and acetic acid.
Dehydrogenation of glycerol, a byproduct of biodiesel production, is another route to obtain vinylcarbinol. Glycerol undergoes catalytic dehydrogenation at elevated temperatures, producing vinylcarbinol.
Furthermore, the Reppe synthesis involves the reaction of formaldehyde with acetylene. Metal catalysts such as palladium or platinum are necessary for this reaction. The formaldehyde and acetylene react to generate vinylcarbinol.
These synthesis methods offer various pathways for the industrial-scale production of vinylcarbinol to meet diverse application requirements.
Allyl Alcohol Uses
- Manufacturers utilize vinylcarbinol to produce resins, which have wide applications in the manufacturing of coatings, adhesives, and sealants.
- Pharmaceutical compounds, including medicines and drugs, undergo synthesis with vinylcarbinol serving as a precursor.
- Vinylcarbinol acts as a key component in the production of plasticizers, which enhance the flexibility and durability of plastics.
- Manufacturers use vinylcarbinol as a building block to produce allyl ethers, which function as solvents and intermediates in organic synthesis.
- Vinylcarbinol contributes to the production of synthetic flavors and fragrances, which add unique characteristics to food, beverages, and personal care products.
- Polymer formulations benefit from the incorporation of vinylcarbinol as a crosslinking agent, resulting in improved mechanical strength and heat resistance.
- Manufacturers produce allyl resins, which exhibit excellent chemical resistance, for use in the production of adhesives, coatings, and sealants.
- Vinylcarbinol serves as a starting material for the synthesis of allyl esters, which find application in the preparation of various cosmetic and personal care products.
- Organic chemistry reactions utilize vinylcarbinol as a reagent to facilitate the synthesis of diverse compounds.
- Vinylcarbinol plays a crucial role in the production of specialty chemicals and intermediates for various industries, including the pharmaceutical, agricultural, and chemical sectors.
Questions:
Q: What type of reaction can be used to prepare allyl alcohol from allyl bromide?
A: Vinylcarbinol can be prepared from allyl bromide through a nucleophilic substitution reaction using a strong base, such as sodium hydroxide or potassium hydroxide.
Q: What is unusual about allylic carbon atoms?
A: Allylic carbon atoms are adjacent to a carbon-carbon double bond, which gives them unique reactivity and stability compared to other carbon atoms in the molecule.
Q: What is allylic alcohol?
A: Allylic alcohol is an alcohol compound where the hydroxyl (-OH) group is attached to an allylic carbon atom, which is adjacent to a carbon-carbon double bond.
Q: Which of the following is an allylic alcohol?
A: 2-Buten-1-ol is an example of an allylic alcohol.
Q: How to form allylic alcohol?
A: Allylic alcohols can be formed by attaching a hydroxyl group to an allylic carbon atom through suitable chemical reactions, such as nucleophilic substitution or addition reactions.
Q: What are secondary allylic alcohols?
A: Secondary allylic alcohols are allylic alcohols where the allylic carbon atom is bonded to two other carbon atoms, and the hydroxyl group is attached to one of these carbon atoms.
Q: How to make allylic alcohol?
A: Allylic alcohols can be synthesized by introducing a hydroxyl group to an allylic carbon atom through appropriate chemical reactions, such as using nucleophiles or adding water to allylic halides or olefins.
Q: Can alcohols be allylic?
A: Yes, alcohols can be allylic if the hydroxyl group is attached to an allylic carbon atom adjacent to a carbon-carbon double bond.
Q: Is allyl alcohol a primary alcohol?
A: No, allyl alcohol is not a primary alcohol. It is classified as a secondary alcohol since the hydroxyl group is attached to a carbon atom bonded to two other carbon atoms.