Ethyl lactate: Difference between revisions

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Revision as of 20:54, 20 November 2011 editRifleman 82 (talk \| contribs)Extended confirmed users32,436 edits →References: * {{cite journal \| doi = 10.1039/C1GC15523G }}← Previous edit		Latest revision as of 06:56, 20 June 2024 edit undoFranciolus (talk \| contribs)1 edit Changed flashpoint, flashpoint measurements according to ISO2719 shows that the flashpoint of ethyl lactate is 58 °C and not 46 °C
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		⚫	{{Use dmy dates\|date=January 2021}}
	{{chembox		{{chembox
	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = ~~402114675~~		\| verifiedrevid = 417919604
	\| Name = Ethyl ~~(-)-<small>L</small>-~~lactate		\| Name = Ethyl lactate
	\| ImageFile = Ethyl L-lactate.png		\| ImageFile = Ethyl lactate.png
	\| ImageSize = 200px		\| ImageSize = 200px
	\| ~~ImageName~~ = Ethyl ~~<small>L</small>~~-~~lactate~~		\| IUPACName = Ethyl 2-hydroxypropanoate
		⚫	\| OtherNames = Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
	\| IUPACName = Ethyl (''R'')-2-hydroxypropanoate
		⚫	\|Section1={{Chembox Identifiers
⚫	\| OtherNames = Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| Section1 = {{Chembox Identifiers
⚫	\| SMILES = CCOC(=O)C(C)O
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 13837423		\| ChemSpiderID = 13837423
		⚫	\| CASNo = 687-47-8
		⚫	\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = F3P750VW8I
		⚫	\| CASNo_Comment = (<small>L</small>-isomer)
			\| CASNo1_Ref = {{cascite\|correct\|??}}
		⚫	\| CASNo1 = 97-64-3
		⚫	\| CASNo1_Comment = (racemate)
			\| CASNo2_Ref = {{cascite\|correct\|??}}
		⚫	\| CASNo2 = 7699-00-5
		⚫	\| CASNo2_Comment = (<small>D</small>-isomer)
			\| EC_number = 202-598-0
		⚫	\| PubChem = 7344
		⚫	\| RTECS = OD5075000
			\| UNNumber = 1192
		⚫	\| SMILES = CCOC(=O)C(C)O
	\| InChI = 1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3		\| InChI = 1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3
	\| InChIKey = LZCLXQDLBQLTDK-UHFFFAOYAV		\| InChIKey = LZCLXQDLBQLTDK-UHFFFAOYAV
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	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = LZCLXQDLBQLTDK-UHFFFAOYSA-N		\| StdInChIKey = LZCLXQDLBQLTDK-UHFFFAOYSA-N
⚫	\| CASNo = 687-47-8
⚫	\| CASNo_Comment = (<small>L</small>-isomer)
⚫	\| CASNo_Ref = {{cascite\|correct\|CAS}}
⚫	\| CASNo1 = 97-64-3
⚫	\| ~~CASNo_Comment~~ = (racemate)
⚫	\| CASNo2 = 7699-00-5
⚫	\| ~~CASNo_Comment~~ = (<small>D</small>-isomer)
⚫	\| PubChem = 7344
⚫	\| RTECS = OD5075000
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| C=5\|H=10\|O=3		\| C=5\|H=10\|O=3
	\| Appearance = ~~Clear to slightly yellow~~ liquid		\| Appearance = Colorless liquid
	\| Density = 1.03 g/cm<sup>3</sup>		\| Density = 1.03 g/cm<sup>3</sup>
	\| Solubility = Miscible		\| Solubility = Miscible
	\| Solvent = ]<br /> and most ]s		\| Solvent = ]<br /> and most ]s
	\| SolubleOther = Miscible		\| SolubleOther = Miscible
	\| MeltingPtC = -26		\| MeltingPtC = -26
	\| ~~BoilingPtCL~~ = 151		\| BoilingPtC = 151 to 155
		⚫	\| SpecRotation = −11.3°
	\| BoilingPtCH = 155
			\| MagSus = -72.6·10<sup>−6</sup> cm<sup>3</sup>/mol
⚫	\| SpecRotation = −11.3°
	}}		}}
	\| ~~Section7~~ = {{Chembox ~~Hazards~~		\|Section3={{Chembox Structure
			\| Dipole = 3.46 ]<ref>{{Cite journal \| doi = 10.1039/b811909k \| title = The green solvent ethyl lactate: an experimental and theoretical characterization \| year = 2009 \| last1 = Aparicio \| first1 = Santiago \| last2 = Alcalde \| first2 = Rafael \| journal = Green Chemistry \| volume = 11 \| issue = 1 \| pages = 65–78}}</ref>
	\| ExternalMSDS =
	\| MainHazards = Irritant (Xi)
⚫	\| NFPA-H = 1
⚫	\| NFPA-F = 1
⚫	\| NFPA-R = 0
	\| RPhrases = {{R10}} {{R37}} {{R41}}
	\| SPhrases = {{S2}} {{S24}} {{S26}} {{S39}}
	\| FlashPt = 46 °C
	}}		}}
	\| ~~Section8~~ = {{Chembox ~~Related~~		\|Section7={{Chembox Hazards
			\| ExternalSDS =
	\| OtherCpds = ]
		⚫	\| NFPA-H = 3
		⚫	\| NFPA-F = 2
		⚫	\| NFPA-R = 0
			\| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}
			\| GHSSignalWord = Danger
			\| HPhrases = {{H-phrases\|226\|318\|335}}
			\| PPhrases = {{P-phrases\|210\|233\|240\|241\|242\|243\|261\|271\|280\|303+361+353\|304+340\|305+351+338\|310\|312\|370+378\|403+233\|403+235\|405\|501}}
			\| FlashPtC = 58
			}}<ref>{{cite web \| url=https://pubchem.ncbi.nlm.nih.gov/compound/Ethyl-lactate#datasheet=LCSS \| title=Ethyl lactate }}</ref><ref>{{cite web \| url=https://cameochemicals.noaa.gov/chemical/700 \| title=ETHYL LACTATE \| CAMEO Chemicals \| NOAA }}</ref>
			\|Section8={{Chembox Related
			\| OtherCompounds = ], ]
	}}		}}
	}}		}}

	'''Ethyl lactate''', also known as lactic acid ethyl ester, is a ~~monobasic~~ ] ~~formed~~ ~~from~~ ] ~~and~~ ], commonly used as a ]. This compound is considered ] and can be used as a water-rinsible degreaser. Ethyl lactate is found naturally in small quantities in a wide variety of foods including ], ], and various ]s. The odor of ethyl lactate when dilute is mild, ]y, ]y, with hints of fruit and ].		'''Ethyl lactate''', also known as lactic acid ethyl ], is the organic compound with the formula CH<sub>3</sub>CH(OH)CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>. It is the ethyl ester of ]. 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 ].<ref>{{Ullmann \|doi=10.1002/14356007.a24_437\|title=Solvents\|year=2000\|last1=Stoye\|first1=Dieter\|isbn=3527306730}}</ref> This compound is considered ] and can be used as a water-rinsible degreaser. Ethyl lactate is found naturally in small quantities in a wide variety of foods including ], ], and various ]s. The odor of ethyl lactate when dilute is mild, ]y, ]y, with hints of fruit and ].<ref>{{cite journal \| doi = 10.1039/C1GC15523G \| title = Ethyl lactate as a solvent: Properties, applications and production processes – a review \| year = 2011 \| last1 = Pereira \| first1 = Carla S. M. \| last2 = Silva \| first2 = Viviana M. T. M. \| last3 = Rodrigues \| first3 = Alírio E. \| journal = Green Chemistry \| volume = 13 \| issue = 10 \| pages = 2658 }}</ref>

			==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 ]. Most biologically sourced ethyl lactate is ethyl (-)-<small>L</small>-lactate. Ethyl lactate is also produced industrially from petrochemical stocks, and this ethyl lactate consists of the racemic mixture of levo and dextro forms. In some jurisdictions, the ''natural'' product is exempt from many restrictions placed upon use and disposal of solvents. Because both enantiomers are found in nature, and because ethyl lactate is easily biodegradable, it is considered to be a ''green'' solvent.		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 ]. Most biologically sourced ethyl lactate is ethyl (−)-<small>L</small>-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 ==
	Due to its relatively low toxicity, ethyl lactate is used commonly in pharmaceutical preparations, ]s,<ref>{{Dead link\|date=December 2010}} ], Center for Food Safety and Applied Nutrition</ref> and ]. Ethyl lactate is also used as solvent for ], ] ], and cellulose ]s.<ref>"Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. ISBN 0815514131, 9780815514138</ref>
			Because both enantiomers are found in nature, and because ethyl lactate is easily biodegradable, it is considered to be a "]." Ethyl lactate and its aqueous solutions are used as sustainable media for ].<ref>{{Cite journal\|last=Dolzhenko\|first=Anton V.\|date=2020\|title=Ethyl lactate and its aqueous solutions as sustainable media for organic synthesis\|url=http://www.sciencedirect.com/science/article/pii/S2352554120305611\|journal=Sustainable Chemistry and Pharmacy\|language=en\|volume=18\|pages=100322\|doi=10.1016/j.scp.2020.100322\|s2cid=224957198}}</ref> Due to its relatively low toxicity, ethyl lactate is used commonly in pharmaceutical preparations, ]s,<ref> ], Center for Food Safety and Applied Nutrition {{webarchive \|url=https://web.archive.org/web/20090107200132/http://www.foodsafety.gov/~dms/eafus.html \|date=7 January 2009 }}</ref> and ]. Ethyl lactate is also used as solvent for ], ] ], and cellulose ]s.<ref>"Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. {{ISBN\|0-8155-1413-1}}, {{ISBN\|978-0-8155-1413-8}}</ref>

		⚫	==Further reading==
	Ethyl lactate ] in the presence of ] and ]s or ] into ] and ].
		⚫	* {{cite journal \|author1=Jacqueline S. Bennett \|author2=Kaitlyn L. Charles \|author3=Matthew R. Miner \|author4=Caitlin F. Heuberger \|author5=Elijah J. Spina \|author6=Michael F. Bartels \|author7=Taylor Foreman \| title = Ethyl lactate as a tunable solvent for the synthesis of aryl aldimines \| journal = Green Chem. \| year = 2009 \| volume = 11 \| issue = 2 \| pages = 166–168 \| doi = 10.1039/b817379f}}

⚫	~~Ethyl~~ ~~lactate can be used as a cosolvent to produce suitable conditions for the formation of aryl aldimines.<ref>~~{{cite journal \| ~~author~~ = Jacqueline S. Bennett, Kaitlyn L. Charles, Matthew R. Miner, Caitlin F. Heuberger, Elijah J. Spina, Michael F. Bartels ~~and~~ Taylor Foreman \| title = Ethyl lactate as a tunable solvent for the synthesis of aryl aldimines \| journal = Green Chem. \| year = 2009 \| volume = 11 \| issue = 2 \| pages = 166–168 \| doi = 10.1039/b817379f}}~~</ref>~~

	==References==		==References==
	{{reflist}}		{{reflist}}
⚫	{{Use dmy dates\|date=~~December~~ ~~2010~~}}

⚫	==Further reading==
	* {{cite journal \| doi = 10.1039/C1GC15523G }}

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Latest revision as of 06:56, 20 June 2024

Ethyl lactate
Names

IUPAC name Ethyl 2-hydroxypropanoate
Other names Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
Identifiers
CAS Number	687-47-8 (L-isomer) 97-64-3 (racemate) 7699-00-5 (D-isomer)
3D model (JSmol)	Interactive image
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,3H2,1-2H3Key: LZCLXQDLBQLTDK-UHFFFAOYSA-N InChI=1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3Key: LZCLXQDLBQLTDK-UHFFFAOYAV
SMILES CCOC(=O)C(C)O
Properties
Chemical formula	C₅H₁₀O₃
Molar mass	118.132 g·mol
Appearance	Colorless liquid
Density	1.03 g/cm
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 (_D)	−11.3°
Magnetic susceptibility (χ)	-72.6·10 cm/mol
Structure
Dipole moment	3.46 D
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H318, H335
Precautionary statements	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	58 °C (136 °F; 331 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 , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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. 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.

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

References

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.
"Ethyl lactate".
"ETHYL LACTATE | CAMEO Chemicals | NOAA".
Stoye, Dieter (2000). "Solvents". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a24_437. ISBN 3527306730.
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.
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.
U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition Archived 7 January 2009 at the Wayback Machine
"Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. ISBN 0-8155-1413-1, ISBN 978-0-8155-1413-8

Categories:

Latest revision as of 06:56, 20 June 2024

Production

Applications

Further reading

References