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	{{chembox		{{chembox
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 402114675		| verifiedrevid = 417919604
			| Name = Cyclopentyl methyl ether
	| Name = Ethyl (-)-<small>L</small>-lactate
	| ImageFile = Ethyl L-lactate.png		| ImageFile = CPME.svg
	| ImageSize = 200px		| ImageSize = 150px
			| ImageName = Chemical structure of cyclopentyl methyl ether
	| ImageName = Ethyl <small>L</small>-lactate
			| PIN = Methoxycyclopentane
	| IUPACName = Ethyl (''R'')-2-hydroxypropanoate
			| OtherNames = CPME
	| OtherNames = Ethyl lactate; Lactic acid ethyl ester; 2-Hydroxypropanoic acid ethyl ester; Actylol; Acytol
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| SMILES = CCOC(=O)C(C)O		| SMILES = COC1CCCC1
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 13837423		| ChemSpiderID = 122157
	| InChI = 1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3		| InChI = 1S/C6H12O/c1-7-6-4-2-3-5-6/h6H,2-5H2,1H3
	| InChIKey = LZCLXQDLBQLTDK-UHFFFAOYAV		| InChIKey = SKTCDJAMAYNROS-UHFFFAOYSA-N
			| CASNo = 5614-37-9
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
	| StdInChI = 1S/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 4067E5GBKB
	| StdInChIKey = LZCLXQDLBQLTDK-UHFFFAOYSA-N
	| CASNo = 687-47-8		| PubChem = 138539
			| EINECS = 445-090-6
	| 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=6|H=12|O=1
	| Appearance = Clear to slightly yellow liquid		| Appearance = Colorless clear liquid
			| Density = 0.8630 g/cm<sup>3</sup> (20 °C) <ref name="Baird2019">{{cite journal |last1=Baird |first1=Zachariah Steven |last2=Uusi-Kyyny |first2=Petri |last3=Pokki |first3=Juha-Pekka |last4=Pedegert |first4=Emilie |last5=Alopaeus |first5=Ville |title=Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds |journal=International Journal of Thermophysics |date=6 Nov 2019 |volume=40 |issue=11 |page=102 |doi=10.1007/s10765-019-2570-9|bibcode=2019IJT....40..102B |doi-access=free }}</ref>
	| Density = 1.03 g/cm<sup>3</sup>
	| Solubility = Miscible		| Solubility = 0.011 g/g
		⚫	| MeltingPtC = -140
	| Solvent = ]<br /> and most ]s
			| BoilingPtC = 106
	| SolubleOther = Miscible
			| BoilingPt_ref = <ref name="Baird2019" />
⚫	| MeltingPtC = -26
		⚫	}}
	| BoilingPtCL = 151
		⚫	|Section7={{Chembox Hazards
	| BoilingPtCH = 155
			| ExternalSDS =
	| SpecRotation = −11.3°
			| GHSPictograms = {{GHS02}}{{GHS07}}
⚫	}}
			| GHSSignalWord = Danger
⚫	| Section7 = {{Chembox Hazards
			| HPhrases = {{H-phrases|225|302|312|315|319}}
	| ExternalMSDS =
			| PPhrases = {{P-phrases|210|233|240|241|242|243|264|270|280|301+312|302+352|303+361+353|305+351+338|312|321|322|330|332+313|337+313|362|363|370+378|403+235|501}}
	| MainHazards = Irritant (Xi)
	| NFPA-H = 1		| NFPA-H = 2
	| NFPA-F = 1		| NFPA-F = 3
	| NFPA-R = 0		| NFPA-R = 0
			| FlashPtC = -1
	| RPhrases = {{R10}} {{R37}} {{R41}}
	| SPhrases = {{S2}} {{S24}} {{S26}} {{S39}}
	| FlashPt = 46 °C
	}}
	| Section8 = {{Chembox Related
	| OtherCpds = ]
	}}		}}
	}}		}}
			'''Cyclopentyl methyl ether''' ('''CPME'''), also known as '''methoxycyclopentane''', is a ] ether solvent. A high boiling point of {{convert|106|C|F}} and preferable characteristics such as low formation of ], relative stability under acidic and basic conditions, formation of azeotropes with water coupled with a narrow explosion range render CPME an attractive alternative to other ethereal solvents such as ] (THF), ] (2-MeTHF), ], and ] (DME).<ref>{{cite journal|date=February 24, 2007|title=Cyclopentyl Methyl Ether as a New and Alternative Process Solvent|journal=Org. Process Res. Dev.|pages=251–258| doi = 10.1021/op0680136|volume=11|issue=2|last1=Watanabe|first1=Kiyoshi|last2=Yamagiwa|first2=Noriyuki|last3=Torisawa|first3=Yasuhiro}}</ref>
	'''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 ].
			== Synthesis ==
	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.
			The synthesis of this compound can be done in two different ways:
			(1) by ] of the ].
	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>
			: ]
	Ethyl lactate ] in the presence of ] and ]s or ] into ] and ].
			(2) by the addition of ] to the ]. This second method is better from the point of view of sustainable chemistry as it does not produce by-products.
	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>
			: ]
			== Applications ==
			Cyclopentyl methyl ether is used in organic synthesis, mainly as a solvent. However it is also useful in ], ], ] and ].
			Some examples of reactions where it acts as a solvent are:
			*Reactions involving alkali agents: nucleophilic substitutions of heteroatoms (alcohols and amines) <ref>Ether compounds and polymerizable compounds and manufacturing methods. By: Kiriki, Satoshi.Aug 3, 2015.JP 2015140302</ref>
			*Lewis acids-mediated reactions: Beckmann Reaction, Friedel-Crafts Reaction etc.<ref>{{cite journal|last1=Torisawa|first1=Yasuhiro|title=Conversion of indanone oximes into isocarbostyrils|journal=Bioorganic & Medicinal Chemistry Letters|date=15 January 2007|volume=17|issue=2|pages=453–455|doi=10.1016/j.bmcl.2006.10.022|pmid=17064893}}</ref>
			*Reactions using Organometallic reagents or basic agents: Claisen condensation, formation of enolates or Grignard reaction.<ref>{{cite journal|last1=Okabayashi|first1=Tomohito|last2=Iida|first2=Akira|last3=Takai|first3=Kenta|last4=Misaki|first4=Tomonori|last5=Tanabe|first5=Yoo|title=Practical and Robust Method for Regio- and Stereoselective Preparation of (E)-Ketene tert-Butyl TMS Acetals and β-Ketoester-derived tert-Butyl (1Z,3E)-1,3-Bis(TMS)dienol Ethers|journal=The Journal of Organic Chemistry|date=September 18, 2007|volume=72|issue=21|pages=8142–8145|doi=10.1021/jo701456t|pmid=17877405}}</ref>
			*Reduction and oxidation.<ref>{{cite journal|last1=Shimada|first1=Toyoshi|last2=Suda|first2=Masahiko|last3=Nagano|first3=Toyohiro|last4=Kakiuchi|first4=Kiyomi|title=Facile Preparation of a New BINAP-Based Building Block, 5,5'-DiiodoBINAP, and Its Synthetic Application|journal=The Journal of Organic Chemistry|date=October 22, 2005|volume=70|issue=24|pages=10178–10181|doi=10.1021/jo0517186|pmid=16292868}}</ref>
			*Reactions with transition metal catalysts.<ref>{{cite journal|last1=Molander|first1=Gary A.|last2=Elia|first2=Maxwell D.|title=Suzuki−Miyaura Cross-Coupling Reactions of Benzyl Halides with Potassium Aryltrifluoroborates|journal=The Journal of Organic Chemistry|date=November 3, 2006|volume=71|issue=24|pages=9198–9202|doi=10.1021/jo061699f|url= |pmid=17109547|pmc=2515367}}</ref>
			*Reactions with azeotropical removal of water: acetalization, etc.<ref>{{cite journal|last1=Azzena|first1=Ugo|last2=Carraro|first2=Massimo|last3=Mamuye|first3=Ashenafi Damtew|last4=Murgia|first4=Irene|last5=Pisano|first5=Luisa|last6=Zedde|first6=Giuseppe|title=Cyclopentyl methyl ether – NH4X: a novel solvent/ catalyst system for low impact acetalization reactions|journal=Green Chemistry|date=17 April 2015|volume=17|issue=6|pages=3281–3284|doi=10.1039/c5gc00465a}}</ref>
			Cyclopentyl methyl ether possesses characteristics that make it a potential alternate for other ethers. According to an evaluation of three chemistry journals from 2020, ethereal solvents have a share of 22–25% of all solvents employed.<ref>{{citation|author=A. Jordan, C.G.J. Hall, L.R. Thorp, H.F. Sneddon|date=2022|doi=10.1021/acs.chemrev.1c00672|pages=6749–6794|periodical=]|title=Replacement of less-preferred dipolar aprotic and ethereal solvents in synthetic organic chemistry with more sustainable alternatives|volume=122|pmc=9098182}}<!-- auto-translated by Module:CS1 translator --></ref>
			In contrast to water-soluble ethers like tetrahydrofuran and 1,4-dioxane, cyclopentyl methyl ether (CPME) - being hydrophobic - acts suitably as an ]. In aqueous phases, only trace amounts of CPME remain due to its low solubility. CPME also exhibits stability at both low and high pH levels, even under elevated temperatures and extended contact times. It can form an ] with water in a ratio of 83.7% CPME to 16.3% water at an azeotropic end temperature of 83 °C.<ref name="Zeon">{{cite web|access-date=2022-10-20|date=June 2018|format=PDF|publisher=Zeon Corporation|title=Novel hydrophobic ether solvent – Cyclopentyl methyl ether – CPME – Technical Data|url=https://www.zeon.co.jp/en/business/enterprise/special/solvent-cpme/pdf/000084448.pdf}}<!-- auto-translated by Module:CS1 translator --></ref> These properties enable CPME to function effectively as an entrainer during ] processes<ref>{{citation|author=D. Rigo, G. Firani, A. Perosa, M. Selva|date=2019|doi=10.1021/acssuschemeng.9b03359|issue=23|pages=18810–18818|periodical=]|title=Acid-Catalyzed Reactions of Isopropenyl Esters and Renewable Diols: A 100% Carbon Efficient Transesterification/Acetalization Tandem Sequence, from Batch to Continuous Flow|volume=7}}<!-- auto-translated by Module:CS1 translator --></ref> and acetalizations.<ref>{{citation|author=U. Azzena, M. Carraro, A.D. Mamuye, I. Murgia, L. Pisano, G. Zedde|date=2015|doi=10.1039/C5GC00465A|issue=6|pages=3281–3284|periodical=]|title=Cyclopentyl methyl ether–NH4X: a novel solvent/catalyst system for low impact acetalization reactions|volume=17}}<!-- auto-translated by Module:CS1 translator --></ref> The solvent also displays low solubility for water in CPME, reported to be 0.3 g / 100 g.<ref>{{Cite web |title=Zeon Corporation |url=https://www.zeon.co.jp/business_e/enterprise/spechemi/cpme_tec_sup_e_200906.pdf |url-status=dead |archive-url=https://web.archive.org/web/20110722102229/http://www.zeon.co.jp/business_e/enterprise/spechemi/cpme_tec_sup_e_200906.pdf |archive-date=2011-07-22 |access-date=2024-08-05 |website=}}</ref>
			Recently, investigations into the use of cyclopentyl methyl ether as an eco-friendly solvent in a wide range of chemical reactions, such as ], ]s, and ]s, have been conducted.<ref>{{cite web|access-date=2022-10-20|date=September 2018|format=PDF|language=en|publisher=Zeon Corporation|title=Synthetic Applications with Cyclopentyl methyl ether (CPME), Ver. 2.0|url=https://www.zeon.co.jp/en/business/enterprise/special/solvent-cpme/pdf/000204797.pdf}}<!-- auto-translated by Module:CS1 translator --></ref><ref>{{citation|author=U. Azzena, M. Carraro, L. Pisano, S. Monticelli, R. Bartolotta, V. Pace|date=2019|doi=10.1002/cssc.201801768|issue=1|pages=40–70|periodical=]|title=Cyclopentyl Methyl Ether: An Elective Ecofriendly Ethereal Solvent in Classical and Modern Organic Chemistry|volume=12|doi-access=free|pmc=6391966}}<!-- auto-translated by Module:CS1 translator --></ref>
			At present, however, the production of cyclopentyl methyl ether, which in multiple respects fulfills the criteria of a "green" chemical, still depends on cyclopentene derived from non-renewable, fossil-fuel sources. The ] ] can yield ] in high yields through ] using a ] contact<ref>{{citation|author=N. Pino, G. Hincapié, D. López|date=2018|doi=10.1021/acs.energyfuels.7b03256|issue=1|pages=561–573|periodical=]|title=Selective Catalytic Route for the Synthesis of High-Density Biofuel Using Biomass-Derived Compounds|volume=32}}<!-- auto-translated by Module:CS1 translator --></ref> or a ]] contact.<ref>{{citation|author=Q. Guo, X. Hou, W. Xiu, J. Liu|date=2022|doi=10.1039/D2RA00016D|pages=11843–11852|periodical=]|title=Efficient conversion of furfural to cyclopentanol over lignin activated carbon supported Ni–Co catalyst|volume=12|doi-access=free|pmc=9016743}}<!-- auto-translated by Module:CS1 translator --></ref> The resulting cyclopentanol can then be easily ] to cyclopentene.
	==References==		==References==
	{{reflist}}		{{reflist}}
	{{Use dmy dates|date=December 2010}}
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