Ethyl benzoate

Last updated
Ethyl benzoate
Ethyl benzoate.svg
Ethyl benzoate 3D ball.png
Names
Preferred IUPAC name
Ethyl benzoate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.078 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-284-3
PubChem CID
UNII
  • InChI=1S/C9H10O2/c1-2-11-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3 Yes check.svgY
    Key: MTZQAGJQAFMTAQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C9H10O2/c1-2-11-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3
    Key: MTZQAGJQAFMTAQ-UHFFFAOYAI
  • O=C(OCC)c1ccccc1
Properties
C9H10O2
Molar mass 150.177 g·mol−1
Appearancecolorless liquid
Density 1.050 g/cm3
Melting point −34 °C (−29 °F; 239 K)
Boiling point 211–213 °C (412–415 °F; 484–486 K)
0.72 mg/mL
log P 2.64
−93.32×10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H315, H319, H411
P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, P501
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Ethyl benzoate, C9H10O2, is an ester formed by the condensation of benzoic acid and ethanol. It is a colorless liquid that is almost insoluble in water, but miscible with most organic solvents.

Contents

As with many volatile esters, ethyl benzoate has a pleasant odor described as sweet, wintergreen, fruity, medicinal, cherry and grape. [1] It is a component of some fragrances and artificial fruit flavors.

Preparation

A simple and commonly used method for the preparation of ethyl benzoate in the laboratory is the acidic esterification of benzoic acid with ethanol and sulfuric acid as catalyst: [2]

Ethyl benzoate esterification.svg

Related Research Articles

<span class="mw-page-title-main">Benzoic acid</span> Organic compound (C6H5COOH)

Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Fischer–Speier esterification</span>

Fischer esterification or Fischer–Speier esterification is a special type of esterification by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. The reaction was first described by Emil Fischer and Arthur Speier in 1895. Most carboxylic acids are suitable for the reaction, but the alcohol should generally be primary or secondary. Tertiary alcohols are prone to elimination. Contrary to common misconception found in organic chemistry textbooks, phenols can also be esterified to give good to near quantitative yield of products. Commonly used catalysts for a Fischer esterification include sulfuric acid, p-toluenesulfonic acid, and Lewis acids such as scandium(III) triflate. For more valuable or sensitive substrates other, milder procedures such as Steglich esterification are used. The reaction is often carried out without a solvent or in a non-polar solvent to facilitate the Dean-Stark method. Typical reaction times vary from 1–10 hours at temperatures of 60-110 °C.

<span class="mw-page-title-main">Sodium benzoate</span> Chemical compound

Sodium benzoate also known as benzoate of soda is the sodium salt of benzoic acid, widely used as a food preservative (with an E number of E211) and a pickling agent. It appears as a white crystalline chemical with the formula C6H5COONa.

<span class="mw-page-title-main">Cinnamic acid</span> Chemical compound

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

<span class="mw-page-title-main">Ethyl oleate</span> Chemical compound

Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless oil although degraded samples can appear yellow.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Hippuric acid</span> Chemical compound

Hippuric acid is a carboxylic acid and organic compound. It is found in urine and is formed from the combination of benzoic acid and glycine. Levels of hippuric acid rise with the consumption of phenolic compounds. The phenols are first converted to benzoic acid, and then to hippuric acid and excreted in urine.

<span class="mw-page-title-main">Ethyl nitrate</span> Chemical compound

Ethyl nitrate is the ethyl ester of nitric acid and has the chemical formula C2H5NO3. It is a colourless, volatile, explosive, and extremely flammable liquid. It is used in organic synthesis and as an intermediate in the preparation of some drugs, dyes, and perfumes.

The Bouveault–Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal. It was first reported by Louis Bouveault and Gustave Louis Blanc in 1903. Bouveault and Blanc demonstrated the reduction of ethyl oleate and n-butyl oleate to oleyl alcohol. Modified versions of which were subsequently refined and published in Organic Syntheses.

<span class="mw-page-title-main">Ethyl acetoacetate</span> Chemical compound

The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a colorless liquid. It is widely used as a chemical intermediate in the production of a wide variety of compounds. It is used as a flavoring for food.

<span class="mw-page-title-main">Methyl benzoate</span> Chemical compound

Methyl benzoate is an organic compound. It is an ester with the chemical formula C6H5CO2CH3. It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents. Methyl benzoate has a pleasant smell, strongly reminiscent of the fruit of the feijoa tree, and it is used in perfumery. It also finds use as a solvent and as a pesticide used to attract insects such as orchid bees.

<span class="mw-page-title-main">Benzyl benzoate</span> Chemical compound

Benzyl benzoate is an organic compound which is used as a medication and insect repellent. As a medication it is used to treat scabies and lice. For scabies either permethrin or malathion is typically preferred. It is applied to the skin as a lotion. Typically two to three applications are needed. It is also present in Balsam of Peru, Tolu balsam, and in a number of flowers.

<span class="mw-page-title-main">Triethyl orthoformate</span> Chemical compound

Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3. This colorless volatile liquid, the orthoester of formic acid, is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol.

<span class="mw-page-title-main">Benzoyl group</span> Chemical group (–C(=O)C₆H₅)

In organic chemistry, benzoyl is the functional group with the formula −COC6H5 and structure −C(=O)−C6H5. It can be viewed as benzaldehyde missing one hydrogen. The benzoyl group has a mass of 105 amu.

In organic chemistry, the Hammett equation describes a linear free-energy relationship relating reaction rates and equilibrium constants for many reactions involving benzoic acid derivatives with meta- and para-substituents to each other with just two parameters: a substituent constant and a reaction constant. This equation was developed and published by Louis Plack Hammett in 1937 as a follow-up to qualitative observations in his 1935 publication.

The Prévost reaction is chemical reaction in which an alkene is converted by iodine and the silver salt of benzoic acid to a vicinal diol with anti stereochemistry. The reaction was discovered by the French chemist Charles Prévost (1899–1983).

<span class="mw-page-title-main">Benzoic anhydride</span> Chemical compound

Benzoic anhydride is the organic compound with the formula (C6H5CO)2O. It is the acid anhydride of benzoic acid and the simplest symmetrical aromatic acid anhydride. It is a white solid.

<span class="mw-page-title-main">PRL-8-53</span> Chemical compound

PRL-8-53 is a nootropic substituted phenethylamine that has been shown to act as a hypermnesic drug in humans; it was first synthesized by medical chemistry professor Nikolaus Hansl at Creighton University in the 1970s as part of his work on amino ethyl meta benzoic acid esters.

Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and ethanol. A colorless liquid at room temperature, it has the semi-developed formula of CH3(CH2)6COOCH2CH3, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers. It is used in the creation of synthetic fruity scents.

References

  1. Ethyl benzoate, thegoodscentscompany.com
  2. Arthur Israel Vogel. Rev. by Brian S. Furniss: Vogel’s textbook of practical organic chemistry. 5. Auflage. Longman, Harlow 1989, ISBN   0-582-46236-3, S. 1076