Lignyl acetate

• CAS: 128-51-8
• Catalog Number: ACM128518
• Category: Main Products
• Molecular Weight: 208.3
• Molecular Formula: C₁₃H₂₀O₂
• Synonyms: 2-NORPINENE-2-ETHANOL,6,6-DIMETHYL:ACETATE;LIGNYL ACETATE;NOPYL ACETATE;2-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl acetate;2-Pinene-10-methyl acetate;2-pinene-10-methylacetate;6,6-dimethyl-2-norpinene-2-ethanoacetate;6,6-Dimethyl-2-norpinene-2-ethanol, acetate
• IUPAC Name: 2-(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethyl acetate
• Boiling Point: 253°C(lit.)
• Flash Point: >230°F
• Density: 0.98g/mL at 25°C(lit.)
• Appearance: colorless transparent liquid
• Exact Mass: 208.14600

Case Study

Synthesis of Nopyl Acetate by Homogeneous Catalytic Esterification of Nopol with Acetic Acid

Hurtado-Burbano, et al. Revista Facultad de Ingeniería Universidad de Antioquia, 2018, 89, 16-25.

Nopyl acetate has a pleasant sweet fruity aroma and is used as a low-cost alternative to linalyl acetate in various perfumes and household products. The production of nopol acetate by esterification of nopol with acetic acid using sulfuric acid as a homogeneous catalyst under different experimental conditions was studied. The results showed that the acetic acid conversion rate was as high as 96% when the temperature was 80 °C, the sulfuric acid concentration was 0.0275 M, and the molar ratio of acetic acid to nopol was 1:3.
Esterification of Nopyl Acetate
· The esterification reactions were conducted in a 25 mL round-bottom flask heated by an oil bath on a hot plate with magnetic stirring and temperature control. The experiment was performed at different temperatures (50, 60, 71, and 80°C) using a 1:1 molar ratio of acetic acid to nopol, and also at 80°C with various molar ratios of acetic acid to nopol (1:1, 1:2, 1:3, 1:4) while keeping the nopol concentration and catalyst concentrations constant (0.0184, 0.0275, 0.0367, 0.0480 mol L-1) with a 1:1 molar ratio of acetic acid to nopol.
· A 0.3 M solution of nopol in toluene (20 mL) was added to the reactor, followed by heating to the desired temperature. Once the temperature was reached, acetic acid and sulfuric acid were added. Samples of 0.160 mL were taken periodically and the acetic acid concentration was determined by titration in Dosimat 775 with 0.1 N NaOH standard solution and phenolphthalein indicator.

Liquid-Liquid Equilibrium of a Quaternary System Including Nopyl Acetate

González, Juan M., et al. Journal of Chemical & Engineering Data, 2015, 60(8), 2280-2284.

Nopyl acetate is a woody compound used in household fragrances. It can be obtained by esterification of β-pinene with formaldehyde to give nopol. The mixture obtained by the heterogeneous catalytic esterification of nopol mainly consists of nopyl acetate, water, and unreacted acetic acid and nopol. Therefore, it is necessary to determine the phase equilibrium of the quaternary system of water + acetic acid + nopyl acetate + nopol. The liquid-liquid equilibrium (LLE) data of this quaternary system were measured at different temperatures and 85.8 kPa atmospheric pressure. The binary interaction parameters at each temperature were obtained and reported in this work.
Experimental methods and procedures
· The quaternary mixture was separated into three pseudoternary subsystems with varying nopol:nopyl acetate molar ratios of 1:3 (M1), 1:1 (M2), and 3:1 (M3) for analysis. The simulation involved minimizing a root-mean-square deviation function using activity coefficients derived from experimental data and thermodynamic models.
· LLE measurements for the ternary systems were conducted by preparing 8 mL mixtures with different nopol:nopyl acetate ratios (1:3, 1:1, and 3:1) in the two-phase region, which were then placed in 10 mL sealed vials. The mixtures were stirred for 8 hours and allowed to settle for another 8 hours at constant temperatures (298.15, 323.15, and 348.15 K) using an IKA KS 4000I shaker with precise temperature control (±0.1 K). Subsequently, samples of both organic and aqueous phases were quickly extracted using syringes and analyzed using gas chromatography.

Custom Reviews

August 09, 2023

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An adde essence
Lignyl acetate has a good fragrance, which can replace orange blossom, cologne and other essences and be added to daily chemicals.

Custom Q&A

What is the molecular formula of lignyl acetate?

The molecular formula of lignyl acetate is C13H20O2.

What are the synonyms of lignyl acetate?

The synonyms of lignyl acetate are Nopyl acetate, Nopol acetate, Citroviol, 2-Pinene-10-methyl acetate, Bicyclo[3.1.1]hept-2-ene-2-ethanol, 6,6-dimethyl-, acetate, 6,6-Dimethyl-2-norpinene-2-ethanol, acetate, and more.

What is the IUPAC name of lignyl acetate?

The IUPAC name of lignyl acetate is 2-(6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl)ethyl acetate.

What is the InChI of lignyl acetate?

The InChI of lignyl acetate is InChI=1S/C13H20O2/c1-9(14)15-7-6-10-4-5-11-8-12(10)13(11,2)3/h4,11-12H,5-8H2,1-3H3.

What is the InChIKey of lignyl acetate?

The InChIKey of lignyl acetate is AWNOGHRWORTNEI-UHFFFAOYSA-N.

What is the molecular weight of lignyl acetate?

The molecular weight of lignyl acetate is 208.30 g/mol.

How many hydrogen bond donor counts are there in lignyl acetate?

There are 0 hydrogen bond donor counts in lignyl acetate.

How many hydrogen bond acceptor counts are there in lignyl acetate?

There are 2 hydrogen bond acceptor counts in lignyl acetate.

How many rotatable bond counts are there in lignyl acetate?

There are 4 rotatable bond counts in lignyl acetate.

What is the topological polar surface area of lignyl acetate?

The topological polar surface area of lignyl acetate is 26.3 Ų.