Ethyl lactate

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Ethyl lactate
Ethyl lactate.png
Names
IUPAC name
Ethyl 2-hydroxypropanoate
Other names
Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.363 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-598-0
PubChem CID
RTECS number
  • OD5075000
UNII
UN number 1192
  • InChI=1S/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3 Yes check.svgY
    Key: LZCLXQDLBQLTDK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3
    Key: LZCLXQDLBQLTDK-UHFFFAOYAV
  • CCOC(=O)C(C)O
Properties
C5H10O3
Molar mass 118.132 g·mol−1
AppearanceColorless liquid
Density 1.03 g/cm3
Melting point −26 °C (−15 °F; 247 K)
Boiling point 151 to 155 °C (304 to 311 °F; 424 to 428 K)
Miscible
Solubility in ethanol
and most alcohols
Miscible
−11.3°
-72.6·10−6 cm3/mol
Structure
3.46 D [1]
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H226, H318, H335
P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
3
2
0
Flash point 46 °C (115 °F; 319 K)
Related compounds
Related compounds
Lactic acid, Methyl lactate
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 lactate, also known as lactic acid ethyl ester, is the organic compound with the formula CH3CH(OH)CO2CH2CH3. It is the ethyl ester of lactic acid. A colorless liquid, it is a chiral ester. Being naturally derived, it is readily available as a single enantiomer. It is commonly used as a solvent. [4] This compound is considered biodegradable and can be used as a water-rinsible degreaser. Ethyl lactate is found naturally in small quantities in a wide variety of foods including wine, chicken, and various fruits. The odor of ethyl lactate when dilute is mild, buttery, creamy, with hints of fruit and coconut. [5]

Production

Ethyl lactate is produced from biological sources, and can be either the levo (S) form or dextro (R) form, depending on the organism that is the source of the lactic acid. Most biologically sourced ethyl lactate is ethyl (−)-L-lactate (ethyl (S)-lactate). Ethyl lactate is also produced industrially from petrochemical stocks, and this ethyl lactate consists of the racemic mixture of levo and dextro forms.

Applications

Because both enantiomers are found in nature, and because ethyl lactate is easily biodegradable, it is considered to be a "green solvent." Ethyl lactate and its aqueous solutions are used as sustainable media for organic synthesis. [6] Due to its relatively low toxicity, ethyl lactate is used commonly in pharmaceutical preparations, food additives, [7] and fragrances. Ethyl lactate is also used as solvent for nitrocellulose, cellulose acetate, and cellulose ethers. [8]

Further reading

Related Research Articles

<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. By some authors, organyl derivatives of acidic hydrogen of other acids are called esters as well, but those compounds do not belong to the category of esters proper, according to the IUPAC. By some authors, if instead of organyl group is some other group, such compounds are called esters as well.

<span class="mw-page-title-main">Lactic acid</span> Group of stereoisomers

Lactic acid is an organic acid. It has a molecular formula CH3CH(OH)COOH. It is white in the solid state and it is miscible with water. When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as natural sources. Lactic acid is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group. It is used as a synthetic intermediate in many organic synthesis industries and in various biochemical industries. The conjugate base of lactic acid is called lactate. The name of the derived acyl group is lactoyl.

<span class="mw-page-title-main">Thioester</span> Organosulfur compounds of the form R–SC(=O)–R’

In organic chemistry, thioesters are organosulfur compounds with the molecular structure R−C(=O)−S−R’. They are analogous to carboxylate esters with the sulfur in the thioester replacing oxygen in the carboxylate ester, as implied by the thio- prefix. They are the product of esterification of a carboxylic acid with a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA. The R and R' represent organyl groups, or H in the case of R.

<span class="mw-page-title-main">Malonic acid</span> Carboxylic acid with chemical formula CH2(COOH)2

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

Green chemistry, also called sustainable chemistry, is an area of chemistry and chemical engineering focused on the design of products and processes that minimize or eliminate the use and generation of hazardous substances. While environmental chemistry focuses on the effects of polluting chemicals on nature, green chemistry focuses on the environmental impact of chemistry, including lowering consumption of nonrenewable resources and technological approaches for preventing pollution.

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

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">Valeric acid</span> Carboxylic acid – CH3(CH2)3COOH

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

<span class="mw-page-title-main">Sulfonic acid</span> Organic compounds with the structure R−S(=O)2−OH

In organic chemistry, sulfonic acid refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

<span class="mw-page-title-main">Xanthate</span> Salt that is a metal-thioate/O-esters of dithiocarbonate

Xanthate usually refers to a salt of xanthic acid. The formula of the salt of xanthic acid is [R−O−CS2]M+ ,. Xanthate also refers to the anion [R−O−CS2]. Xanthate also may refer to an ester of xanthic acid. The formula of xanthic acid is R−O−C(=S)−S−H, while the formula of the esters of xanthic acid is R−O−C(=S)−S−R', where R and R' are organyl groups. The salts of xanthates are also called O-organyl dithioates. The esters of xanthic acid are also called O,S-diorganyl esters of dithiocarbonic acid. The name xanthate is derived from Ancient Greek ξανθός xanthos, meaning “yellowish, golden”, and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and for extraction of certain ores. They are also versatile intermediates in organic synthesis.

<span class="mw-page-title-main">Polylactic acid</span> Biodegradable polymer

Polylactic acid, also known as poly(lactic acid) poly, lactic, acid or polylactide (PLA), is a thermoplastic polyester with backbone formula (C
3
H
4
O
2
)
n
or [–C(CH
3
)HC(=O)O–]
n
, formally obtained by condensation of lactic acid C(CH
3
)(OH)HCOOH
with loss of water. It can also be prepared by ring-opening polymerization of lactide [–C(CH
3
)HC(=O)O–]
2
, the cyclic dimer of the basic repeating unit.

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

Levulinic acid, or 4-oxopentanoic acid, is an organic compound with the formula CH3C(O)CH2CH2CO2H. It is classified as a keto acid. This white crystalline solid is soluble in water and polar organic solvents. It is derived from degradation of cellulose and is a potential precursor to biofuels, such as ethyl levulinate.

<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the US. Dimethyl carbonate is often considered to be a green reagent.

<span class="mw-page-title-main">Ethylene carbonate</span> Chemical compound

Ethylene carbonate (sometimes abbreviated EC) is the organic compound with the formula (CH2O)2CO. It is classified as the cyclic carbonate ester of ethylene glycol and carbonic acid. At room temperature (25 °C) ethylene carbonate is a transparent crystalline solid, practically odorless and colorless, and somewhat soluble in water. In the liquid state (m.p. 34-37 °C) it is a colorless odorless liquid.

<span class="mw-page-title-main">Cellulose acetate phthalate</span> Chemical compound

Cellulose acetate phthalate (CAP), also known as cellacefate (INN) and cellulosi acetas phthalas, is a commonly used polymer phthalate in the formulation of pharmaceuticals, such as the enteric coating of tablets or capsules and for controlled release formulations. It is a cellulose polymer where about half of the hydroxyls are esterified with acetyls, a quarter are esterified with one or two carboxyls of a phthalic acid, and the remainder are unchanged. It is a hygroscopic white to off-white free-flowing powder, granules, or flakes. It is tasteless and odorless, though may have a weak odor of acetic acid. Its main use in pharmaceutics is with enteric formulations. It can be used together with other coating agents, e.g. ethyl cellulose. Cellulose acetate phthalate is commonly plasticized with diethyl phthalate, a hydrophobic compound, or triethyl citrate, a hydrophilic compound; other compatible plasticizers are various phthalates, triacetin, dibutyl tartrate, glycerol, propylene glycol, tripropionin, triacetin citrate, acetylated monoglycerides, etc.

Performic acid (PFA) is an organic compound with the formula CH2O3. It is an unstable colorless liquid which can be produced by mixing formic acid with hydrogen peroxide. Owing to its oxidizing and disinfecting action, it is used in the chemical, medical and food industries.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

Lactonitrile is the organic compound with the formula CH3CH(OH)CN. It is an intermediate in the industrial production of ethyl lactate and lactic acid. It is the cyanohydrin of acetaldehyde. It is a colorless liquid, although degraded samples can appear yellow.

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

Methyl lactate, also known as lactic acid methyl ester, is the organic compound with the formula CH3CH(OH)CO2CH3. It is the methyl ester of lactic acid. A colorless liquid, it is the simplest chiral ester. Being naturally derived, it is readily available as a single enantiomer.

11-Aminoundecanoic acid is an organic compound with the formula H2N(CH2)10CO2H. This white solid is classified as an amine and a fatty acid. 11-Aminoundecanoic acid is a precursor to Nylon-11.

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

Dihydrolevoglucosenone (Cyrene) is a bicyclic, chiral, seven-membered heterocyclic cycloalkanone which is a waste derived and fully biodegradable aprotic dipolar solvent. It is a environmentally friendly alternative to dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP).

References

  1. Aparicio, Santiago; Alcalde, Rafael (2009). "The green solvent ethyl lactate: an experimental and theoretical characterization". Green Chemistry. 11 (1): 65–78. doi:10.1039/b811909k.
  2. "Ethyl lactate".
  3. "ETHYL LACTATE | CAMEO Chemicals | NOAA".
  4. Stoye, Dieter (2000). "Solvents". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437.
  5. Pereira, Carla S. M.; Silva, Viviana M. T. M.; Rodrigues, Alírio E. (2011). "Ethyl lactate as a solvent: Properties, applications and production processes – a review". Green Chemistry. 13 (10): 2658. doi:10.1039/C1GC15523G.
  6. Dolzhenko, Anton V. (2020). "Ethyl lactate and its aqueous solutions as sustainable media for organic synthesis". Sustainable Chemistry and Pharmacy. 18: 100322. doi:10.1016/j.scp.2020.100322. S2CID   224957198.
  7. U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition Archived 7 January 2009 at the Wayback Machine
  8. "Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. ISBN   0-8155-1413-1, ISBN   978-0-8155-1413-8