LACTIC ACID ETHYL ESTER

Lactic acid ethyl ester is an environmentally benign solvent with effectiveness comparable to petroleum-based solvents. 
Lactic acid ethyl ester is found naturally in small quantities in a wide variety of foods including wine, chicken, and various fruits. 
Lactic acid ethyl ester is the organic compound with the formula CH3CH(OH)CO2CH2CH3. 

CAS Number: 687-47-8
EC Number: 202-598-0
Molecular Formula: C5H10O3
Molecular Weight (g/mol): 118.13

Lactic acid ethyl ester is found naturally in small quantities in a wide variety of foods including wine, chicken, and various fruits. 
The odor of Lactic acid ethyl ester when dilute is mild, buttery, creamy, with hints of fruit and coconut.

Lactic acid ethyl ester is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.
Lactic acid ethyl ester is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.

Lactic acid ethyl ester, also known as actylol, is the organic compound with the formula CH3CH(OH)CO2CH2CH3. 
Lactic acid ethyl ester is the ethyl ester of lactic acid. 

A colorless liquid, Lactic acid ethyl ester is a chiral ester. 
Being naturally derived, Lactic acid ethyl ester is readily available as a single enantiomer. 

Lactic acid ethyl ester is commonly used as a solvent.
Lactic acid ethyl ester is considered biodegradable and can be used as a water-rinsible degreaser. 

Lactic acid ethyl ester is an environmentally benign solvent with effectiveness comparable to petroleum-based solvents. 
The worldwide solvent market is about 30 million pounds per year, where Lactic acid ethyl ester can have an important share. 

Lactic acid ethyl ester is considered a chemical commodity and has attracted much attention in recent years, since Lactic acid ethyl ester is formed by the esterification reaction of ethanol and lactic acid, which can be generated from biomass raw materials through fermentation. 
In this work, an overview regarding the main properties and applications of Lactic acid ethyl ester, as well as Lactic acid ethyl ester synthesis and production processes, with a particular emphasis on reactive/separation processes, is presented.

Lactic acid ethyl ester, lactic acid ethyl ester or 2-hydroxypropanoic acid ethyl ester is the chemical compound of lactic acid with ethanol in the form of an ester.  
Depending on Lactic acid ethyl ester synthesis, Lactic acid ethyl ester is available as racemate or pure substance.

If Lactic acid ethyl ester is split back into Lactic acid ethyl ester starting materials ethanol and lactic acid (e.g. by a chemical reaction), Lactic acid ethyl ester can be decomposed in nature. 
Esterases, naturally occurring enzymes, can also carry out the split back into the original materials. 

Lactic acid ethyl ester is therefore considered a "green solvent", as Lactic acid ethyl ester does not leave any toxic decomposition products in the ecosystem. 
This provides an advantage over chlorinated solvents or glycols or glycol ethers, which have a higher biological toxicity.

Also known as lactic acid ethyl ester, is a monobasic ester formed from lactic acid and ethanol, commonly used as a solvent hence the name “lactic acid ethyl ester”. 
Lactic acid ethyl ester is considered biodegradable and can be used as a water-risible degreaser. 
Lactic acid ethyl ester is found naturally in small quantities in a wide variety of foods including wine, chicken, and various fruits. 

Lactic acid ethyl ester 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. 
The most biologically sourced Lactic acid ethyl ester is ethyl (−)-L-lactate (ethyl (S)-lactate).

Lactic acid ethyl ester is also produced industrially from petrochemical stocks, and this Lactic acid ethyl ester consists of the racemic mixture of Levo and Dextro forms. 
In some jurisdictions, the natural product is exempt from many restrictions placed upon the use and disposal of solvents. 
Because both enantiomers are found in nature, and because Lactic acid ethyl ester is easily biodegradable, Lactic acid ethyl ester is considered to be a “green solvent.”

Uses of Lactic acid ethyl ester:
Lactic acid ethyl ester is used as a solvent substitute for glycol ethers in photolithography in the semiconductor manufacturing industry.
Lactic acid ethyl ester is used in some nail polish removers.

Lactic acid ethyl ester is used as a solvent for resins, dyes, and coatings; has FDA approval for use as a food flavoring agent
Lactic acid ethyl ester is the active ingredient in many anti-acne preparations.

Uses at industrial sites:
Lactic acid ethyl ester is used in the following products: semiconductors, photo-chemicals, polymers, metal surface treatment products, non-metal-surface treatment products and washing & cleaning products.
Lactic acid ethyl ester is used in the following areas: formulation of mixtures and/or re-packaging.

Lactic acid ethyl ester is used for the manufacture of: electrical, electronic and optical equipment and machinery and vehicles.
Release to the environment of Lactic acid ethyl ester can occur from industrial use: in processing aids at industrial sites.

Industry Uses:
Processing aids, not otherwise listed
Solvent
Solvents (which become part of product formulation or mixture)

Consumer Uses:
Lactic acid ethyl ester is used in the following products: air care products, biocides (e.g. disinfectants, pest control products), perfumes and fragrances, polishes and waxes, washing & cleaning products and cosmetics and personal care products.
Other release to the environment of Lactic acid ethyl ester is likely to occur from: indoor use as processing aid and outdoor use as processing aid.

Widespread uses by professional workers:
Lactic acid ethyl ester is used in the following products: polishes and waxes and washing & cleaning products.
Other release to the environment of Lactic acid ethyl ester is likely to occur from: indoor use as processing aid.

Industrial Processes with risk of exposure:
Semiconductor Manufacturing
Painting (Solvents)
Plastic Composites Manufacturing

Applications of Lactic acid ethyl ester:
Lactic acid ethyl ester is an excellent ingredient for formulating printing inks, coatings, resin cleaners, paint strippers, graffiti removers, ink cleaners, etc. 
Lactic acid ethyl ester alone and is an ideal wipe solvent. 

Lactic acid ethyl ester can be used in industrial coatings applications, primarily in coil, extrusion, wood furniture and fixtures, containers and closures, automotive finishes and machinery. 
Lactic acid ethyl ester is 100% biodegradable, easy and inexpensive to recycle. 

Due to Lactic acid ethyl ester low toxicity, Lactic acid ethyl ester is a popular choice across many different production scenarios. 
Lactic acid ethyl ester is also used as a solvent with various types of polymers. 
In the presence of water, acids and bases the chemical will hydrolyse into ethanol and lactic acid. 

Because both enantiomers are found in nature, and because Lactic acid ethyl ester is easily biodegradable, Lactic acid ethyl ester is considered to be a "green solvent." 
Lactic acid ethyl ester and Lactic acid ethyl ester aqueous solutions are used as sustainable media for organic synthesis.

Due to Lactic acid ethyl ester relatively low toxicity, Lactic acid ethyl ester is used commonly in pharmaceutical preparations, food additives, and fragrances. 
Lactic acid ethyl ester is also used as solvent for nitrocellulose, cellulose acetate, and cellulose ethers.

Production of Lactic acid ethyl ester:
Lactic acid ethyl ester 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 Lactic acid ethyl ester is ethyl (−)-L-lactate (ethyl (S)-lactate). 
Lactic acid ethyl ester is also produced industrially from petrochemical stocks, and this Lactic acid ethyl ester consists of the racemic mixture of levo and dextro forms.

Methods of Manufacturing of Lactic acid ethyl ester:

Derivation: (a) By the esterification of lactic acid with ethanol; (b) by combining acetaldehyde with hydrogen cyanide to form acetaldehyde cyanohydrin, which is converted into Lactic acid ethyl ester by treating with ethanol and an inorganic acid.

d-Lactic acid ethyl ester is obtained from d-lactic acid by azeotropic distillation with ethyl alcohol or benzene in the presence of concentrated H2SO4.
The l-form is prepared in similar fashion starting from l-lactic acid.
The racemic product is prepared by boiling for 24 hours optically inactive lactic acid with ethyl alcohol in carbon tetrachloride, or with an excess of ethyl alcohol in the presence of chlorosulfonic acid, or in the presence of benzenesulfonic acid in benzene solution.

Handling and Storage of Lactic acid ethyl ester:

Nonfire Spill Response:
ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. 
All equipment used when handling Lactic acid ethyl ester must be grounded. 

Do not touch or walk through spilled material. 
Stop leak if you can do Lactic acid ethyl ester without risk. 

Prevent entry into waterways, sewers, basements or confined areas. 
A vapor-suppressing foam may be used to reduce vapors. 

Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. 
Use clean, non-sparking tools to collect absorbed material.

LARGE SPILL: 
Dike far ahead of liquid spill for later disposal. 
Water spray may reduce vapor, but may not prevent ignition in closed spaces.

Reactivity Profile of Lactic acid ethyl ester:

Lactic acid ethyl ester is an ester. 
Esters react with acids to liberate heat along with alcohols and acids. 
Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. 

Heat is also generated by the interaction of esters with caustic solutions. 
Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Fire Fighting of Lactic acid ethyl ester:
The majority of these products have a very low flash point. 
Use of water spray when fighting fire may be inefficient.

SMALL FIRE: 
Dry chemical, CO2, water spray or alcohol-resistant foam. 
Do not use dry chemical extinguishers to control fires involving nitromethane (UN1261) or nitroethane (UN2842).

LARGE FIRE: 
Water spray, fog or alcohol-resistant foam. 
Avoid aiming straight or solid streams directly onto Lactic acid ethyl ester. 
If Lactic acid ethyl ester can be done safely, move undamaged containers away from the area around the fire.

FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: 
Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. 
Cool containers with flooding quantities of water until well after fire is out. 

Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. 
ALWAYS stay away from tanks engulfed in fire. 
For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn.

Accidental Release Measures of Lactic acid ethyl ester:

Isolation and Evacuation:

IMMEDIATE PRECAUTIONARY MEASURE: 
Isolate spill or leak area for at least 50 meters (150 feet) in all directions.

LARGE SPILL: 
Consider initial downwind evacuation for at least 300 meters (1000 feet).

FIRE: 
If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

Cleanup Methods:
Use personal protective equipment. 
Avoid breathing vapors, mist or gas. 

Ensure adquate ventilation. 
Remove all sources of ignition. 

Evacuate personnel to safe areas. 
Beware of vapors accumulating to form explosive concentrations. 
Vopors can accumulate in low areas.

Disposal Methods of Lactic acid ethyl ester:
Recycle any unused portion of the material for Lactic acid ethyl ester approved use or return Lactic acid ethyl ester to the manufacturer or supplier. 

Ultimate disposal of the chemical must consider:
Lactic acid ethyl ester's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. 
If Lactic acid ethyl ester is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Identifiers of Lactic acid ethyl ester:
CAS Number: 
687-47-8 (L-isomer)
97-64-3 (racemate)
7699-00-5 (D-isomer)

ChemSpider: 13837423
ECHA InfoCard: 100.002.363
EC Number: 202-598-0
PubChem CID: 7344
RTECS number: OD5075000
UNII: F3P750VW8I
UN number: 1192
CompTox Dashboard (EPA): DTXSID6029127
InChI: InChI=1S/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3
Key: LZCLXQDLBQLTDK-UHFFFAOYSA-N
InChI=1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3
Key: LZCLXQDLBQLTDK-UHFFFAOYAV
SMILES: CCOC(=O)C(C)O

Synonym(s): (S)-(-)-Lactic acid ethyl ester, L(-)-Lactic acid ethyl ester, (S)-(-)-2-Hydroxypropionic acid ethyl ester
Linear Formula: CH3CH(OH)COOC2H5
CAS Number: 687-47-8
Molecular Weight: 118.13
MDL number: MFCD00004518
EC Index Number: 211-694-1

CAS: 687-47-8
Molecular Formula: C5H10O3
Molecular Weight (g/mol): 118.13
MDL Number: MFCD00004518
InChI Key: LZCLXQDLBQLTDK-BYPYZUCNSA-N
PubChem CID: 92831
ChEBI: CHEBI:78322
IUPAC Name: ethyl (2S)-2-hydroxypropanoate
SMILES: CCOC(=O)C(C)O

Properties of Lactic acid ethyl ester:
Chemical formula: C5H10O3
Molar mass: 118.132 g·mol−1
Appearance: Colorless 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)
Solubility in water: Miscible
Solubility in ethanol
and most alcohols: Miscible
Chiral rotation ([α]D): −11.3°
Magnetic susceptibility (χ): -72.6·10−6 cm3/mol

vapor pressure: 1.6 hPa ( 20 °C)
Quality Level: 200
Assay: ≥99% (GC)
form: liquid
autoignition temp.: 400 °C
potency: >2000 mg/kg LD50, oral (Rat)
expl. lim.: 1.5-16.4 % (v/v)
pH: 4 (20 °C, 50 g/L in H2O)
kinematic viscosity: 2.7 cSt(25 °C)
bp: 154 °C/1013 hPa
mp: -25 °C
transition temp: flash point 53 °C
density: 1.03 g/cm3 at 20 °C
storage temp.: 2-30°C
InChI: 1S/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3/t4-/m0/s1
InChI key: LZCLXQDLBQLTDK-BYPYZUCNSA-N

Molecular Weight: 118.13 g/mol
XLogP3-AA: 0.2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 3
Exact Mass: 
118.062994177 g/mol
Monoisotopic Mass: 
118.062994177 g/mol
Topological Polar Surface Area: 46.5Ų
Heavy Atom Count: 8
Complexity: 79.7
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Lactic acid ethyl ester:
Acidity: 0.1% max. (as lactic acid)
Melting Point: -26.0°C
Density: 1.0340g/mL
Boiling Point: 154.0°C
Flash Point: 46°C
Infrared Spectrum: Authentic
Assay Percent Range: 96% min. (GC)
Packaging: Glass bottle
Linear Formula: CH3CH(OH)CO2C2H5
Refractive Index: 1.4100 to 1.4160
Quantity: 250 mL
Beilstein: 03,264
Fieser: 17,135
Merck Index: 14,3817
Specific Gravity: 1.034
Specific Rotation Condition: − 10.00 (20.00°C neat)
Specific Rotation: − 10.00
Solubility Information: Solubility in water: soluble. Other solubilities: miscible with alcohols,ketones and esters
Formula Weight: 118.13
Percent Purity: 97%
Physical Form: Liquid
Chemical Name or Material: Ethyl L(-)-lactate

Structure of Lactic acid ethyl ester:
Dipole moment: 3.46 D

Related compounds of Lactic acid ethyl ester:
Lactic acid, MLactic acid ethyl ester

Related Products of Lactic acid ethyl ester:
Dimethyl Glutaconate (~10% Cis)
(E,E)-4,6-Dimethyl-2,4-heptadienoic Acid
3,6-Dimethyl-3-heptanol
1,1-Dimethoxybutane
(E)-6,6-Dimethyl-2-hept-1-en-4-yn-1-amine

Names of Lactic acid ethyl ester:

Regulatory process names:
2-Hydroxypropanoic acid ethyl ester
Actylol
Acytol
Ethyl 2-hydroxypropionate
Ethyl alpha-hydroxypropionate
ethyl DL-lactate
Ethyl lactate
ETHYL LACTATE
Ethyl lactate
ethyl lactate
Ethyl lactate (natural)
ethyl lactate ethyl DL-lactate
ethyl lactate; ethyl DL-lactate
Ethylester kyseliny mlecne
Lactate d'ethyle
Lactic acid, ethyl ester
Propanoic acid, 2-hydroxy-, ethyl ester
Solactol

Translated names:
DL-mleczan etylu (pl)
ester etylowy kwasu mlekowego (pl)
Ethyl DL-lactat (de)
ethyl-DL-laktát (cs)
ethyl-laktát (cs)
ethyl-laktát ethyl-DL-laktát (cs)
ethyllacta (da)
ethyllactaat (nl)
Ethyllactat (de)
Ethyllactat Ethyl DL-lactat (de)
etil DL-lactat (ro)
etil DL-laktat (sl)
etil lactat (ro)
etil lactat etil DL-lactat (ro)
etil laktat (sl)
etil laktat etil DL-laktat (sl)
etil-DL-laktat (hr)
etil-DL-laktatas (lt)
etil-DL-laktát (hu)
etil-DL-laktāts (lv)
etil-laktat (hr)
etil-laktát (hu)
etil-laktát etil-DL-laktát (hu)
etillaktatas (lt)
etillaktatas etil-DL-laktatas (lt)
etillaktāts (lv)
etyl-(RS)-laktát (sk)
etyl-laktát (sk)
etyllaktat (no)
etyllaktat (sv)
etyylilaktaatti (fi)
Etüül-DL-laktaat (et)
Etüüllaktaat (et)
lactate d'éthyle; DL-lactate d'éthyle; (fr)
lactato de etilo (es)
lactato de etilo (pt)
lattato di etile (it)
mleczan etylu (pl)
mleczan etylu DL-mleczan etylu ester etylowy kwasu mlekowego (pl)
γαλακτικό αιθυλο (el)
етил DL-лактат (bg)
етил лактат (bg)
етил лактат етил DL-лактат (bg)

IUPAC names:
2-ethoxypropanoic acid
ethyl (2R)-2-hydroxypropanoate
Ethyl (S)-2-hydroxypropanoate
ethyl 2-hydroxypropanoat
ETHYL 2-HYDROXYPROPANOATE
Ethyl 2-hydroxypropanoate
ethyl 2-hydroxypropanoate
Ethyl alpha hydroxypropionate
Ethyl DL Lactate
ethyl DL-lactate
ETHYL LACTATE
Ethyl Lactate
Ethyl lactate
ethyl lactate
ethyl lactate
ethyl lactate;
Ethyllactat
Ethyl 2-hydroxypropanoate

Other names:
Ethyl lactate
Lactic acid ethyl ester
2-Hydroxypropanoic acid ethyl ester
Actylol
Acytol

Other identifiers:
2676-33-7
607-129-00-7
97-64-3

Synonyms of Lactic acid ethyl ester:
ETHYL LACTATE
97-64-3
Ethyl 2-hydroxypropanoate
Solactol
Actylol
Acytol
Lactic acid, ethyl ester
Ethyl 2-hydroxypropionate
Propanoic acid, 2-hydroxy-, ethyl ester
Lactate d'ethyle
2-Hydroxypropanoic acid ethyl ester
Lactic Acid Ethyl Ester
Ethyl alpha-hydroxypropionate
FEMA No. 2440
Eusolvan
Ethyl lactate (natural)
Ethylester kyseliny mlecne
Lactate d'ethyle [French]
NSC 8850
HSDB 412
Ethylester kyseliny mlecne [Czech]
2-Hydroxypropionic Acid Ethyl Ester
EINECS 202-598-0
UN1192
Ethyl ester of lactic acid
BRN 1209448
UNII-F3P750VW8I
AI3-00395
F3P750VW8I
Ethyl .alpha.-hydroxypropionate
DTXSID6029127
CHEBI:78321
NSC-8850
4-03-00-00643 (Beilstein Handbook Reference)
ethyl d-lactate
Ethyl lactate,C5H10O3,97-64-3
EthylL-(-)-Lactate
ethyl-lactate
ethyl DL-lactate
DL-Ethyl Lactate
Milchsaureathylester
Nat. Ethyl Lactate
MFCD00065359
Ethyl racemic-lactate
lactic acid ethylester
(S)-(-)-2-Hydroxypropionic acid ethyl ester
PURASOLV ELS
VERTECBIO EL
Lactic acid-ethyl ester
ELT (CHRIS Code)
Mono-Ethyl mono-lactate
ETHYL LACTATE [MI]
(.+/-.)-Ethyl lactate
Ethyl 2-hydroxypropanoate #
ETHYL LACTATE [FCC]
SCHEMBL22598
ETHYL LACTATE [FHFI]
ETHYL LACTATE [HSDB]
ETHYL LACTATE [INCI]
ETHYL LACTATE [MART.]
DTXCID509127
WLN: QVY1 & O2
ETHYL LACTATE [WHO-DD]
CHEMBL3186323
(+-)-Ethyl 2-hydroxypropanoate
(+-)-Ethyl 2-hydroxypropionate
FEMA 2440
NSC8850
Tox21_200889
2-hydroxy-propionic acid ethyl ester
NA1192
Ethyl lactate, >=98%, FCC, FG
AKOS009157222
LS-2733
UN 1192
(+/-)-LACTIC ACID ETHYL ESTER
CAS-97-64-3
NCGC00248866-01
NCGC00258443-01
(+/-)-ETHYL 2-HYDROXYPROPIONATE
AS-13500
SY030456
A9137
Ethyl lactate [UN1192] [Flammable liquid]
Ethyl lactate, natural, >=98%, FCC, FG
Ethyl lactate, SAJ first grade, >=97.5%
FT-0626259
FT-0627926
FT-0651151
L0003
Ethyl lactate [UN1192] [Flammable liquid]
EN300-115258
A845735
Q415418
J-521263
2-[(4-benzylpiperazin-1-yl)methyl]isoindoline-1,3-dione
(±)-Ethyl 2-hydroxypropanoate
(±)-Ethyl 2-hydroxypropionate
(±)-Ethyl lactate
2-Hydroxypropanoate d'éthyle [French] [ACD/IUPAC Name]
2-Hydroxypropanoic acid ethyl ester
97-64-3 [RN]
Ethyl 2-hydroxypropanoate [ACD/IUPAC Name]
Ethyl ester of lactic acid
Ethyl lactate [ACD/Index Name] [Wiki]
Ethyl α-hydroxypropionate
Ethyl α-hydroxypropionate
Ethyl-2-hydroxypropanoat [German] [ACD/IUPAC Name]
MFCD00065359 [MDL number]
OD5075000
Propanoic acid, 2-hydroxy-, ethyl ester [ACD/Index Name]
QY1&VO2 [WLN]
2-hydroxypropionic acid ethyl ester
4-03-00-00643 [Beilstein]
Actylol
Acytol
DL-Ethyl Lactate
DL-Ethyllactate
DL-LACTIC ACID, ETHYL ESTER
Ethyl 2-hydroxy propanoate
Ethyl lactate,C5H10O3,97-64-3
Ethyl racemic-lactate
Ethylester kyseliny mlecne [Czech]
ethyllactate
Ethyl-lactate
Eusolvan
Lactate d'ethyle [French]
lactic acid ethyl ester
Lactic acid, ethyl ester
Lactic acid-ethyl ester
L-lactic acid ethyl ester
MFCD00077825 [MDL number]
Milchs??ure??thylester
Propanoic acid, 2-hydroxy-, ethyl ester (9CI)
Solactol
UN 1192