Related Experiment Video
Updated: May 9, 2026
10:18
Extraction of Lignin with High β-O-4 Content by Mild Ethanol Extraction and Its Effect on the Depolymerization Yield
Published on: January 7, 2019
Thermal behavior of pinan-2-ol and linalool
Janne Leiner1, Achim Stolle, Bernd Ondruschka
1Institute for Technical Chemistry and Environmental Chemistry (ITUC), Friedrich-Schiller University Jena, Lessingstr. 12, D-07743 Jena, Germany.
Molecules (Basel, Switzerland)
|July 19, 2013
Summary
This study explores the thermal isomerization of pinan-2-ol to produce linalool, a key fragrance intermediate. Researchers identified specific conditions to enhance linalool yield and selectivity during pyrolysis.
Area of Science:
- Organic Chemistry
- Chemical Engineering
- Process Chemistry
Background:
- Linalool is a vital intermediate in synthesizing isoprenoid fragrance compounds and vitamins A and E.
- Thermal gas-phase isomerization of pinan-2-ol presents a viable production route for linalool.
Purpose of the Study:
- To investigate the thermal gas-phase isomerization of cis- and trans-pinan-2-ol to linalool.
- To understand the effects of various reaction parameters on linalool yield and selectivity.
Main Methods:
- Experiments conducted in a flow-type apparatus.
- Temperature range: 350–600 °C.
- Residence time range: 0.6–0.8 s.
Main Results:
- Pinan-2-ol rearrangement yields linalool, with side products including plinols from consecutive reactions.
- Reaction parameters like temperature, residence time, and surface-to-volume ratio influence yield and selectivity.
- Ene-cyclization of linalool to plinols was also investigated.
Conclusions:
- Optimizing selectivity for linalool production via pinan-2-ol pyrolysis is challenging due to gas-phase reaction dynamics.
- Specific pyrolysis conditions were identified to improve both linalool selectivity and yield.
Related Concept Videos
02:32Physical Properties of Alcohols and Phenols
Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
Alcohols possess a higher boiling point than aliphatic hydrocarbons of similar...
01:57Preparation of Diols and Pinacol Rearrangement
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
01:01Distillation: Vapor–Liquid Equilibria
Distillation is a separation technique that takes advantage of the boiling point properties of disparate elements in a mixture. To perform distillation, we begin by heating a miscible mixture of two liquids with a significant difference in boiling points (at least 20°C). As the solution heats up and reaches the bubble point of the more volatile component, some molecules of the more volatile component transition into the gas phase and travel upward into the condenser, which is a glass tube with...
02:23Structure and Nomenclature of Alcohols and Phenols
Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
02:17Physical Properties of Ethers
Overview
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
Ethers can act as hydrogen bond acceptors, making them more water-soluble than hydrocarbons, but since ethers cannot act as hydrogen bond donors, they are much less soluble in water than alcohols. Ethers are considered...
01:27Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.