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Revision as of 08:28, 18 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 472241937 of page Methyl_formate for the Chem/Drugbox validation project (updated: 'ChEMBL').		Latest revision as of 17:26, 23 December 2024 edit Nyxion303 (talk | contribs)Extended confirmed users8,383 edits Rescuing 2 sources and tagging 0 as dead.) #IABot (v2.0.9.5Tag: IABotManagementConsole [1.3]
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 472240624
			| Watchedfields = changed
	| Name = '''Methyl formate'''
			| verifiedrevid = 477501961
	| ImageFileL1 = Methyl formate.svg
			| Name = Methyl formate
	| ImageSizeL1 = 100px
	| ImageNameL1 = Structural formula of methyl formate		| ImageFileL1 = Methyl formate.png
			| ImageSizeL1 = 150
	| ImageFileR1 = Methyl-formate-3D-balls.png
			| ImageNameL1 = Structural formula of methyl formate
	| ImageSizeR1 = 100px
			| ImageFileR1 = Methyl-formate-3D-balls.png
	| ImageNameR1 = Ball-and-stick model of the methyl formate molecule
			| ImageSizeR1 = 150
	| IUPACName = methyl methanoate
			| ImageNameR1 = Ball-and-stick model of the methyl formate molecule
	| Section1 = {{Chembox Identifiers
			| ImageFile2 = Commercial methyl formate.jpg
	| CASNo_Ref = {{cascite|correct|CAS}}
			| PIN = Methyl formate
			| SystematicName = Methyl methanoate
			| OtherNames = R-611
			|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 107-31-3		| CASNo = 107-31-3
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 295026
	| PubChem = 7865		| ChEBI = 77699
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| SMILES = O=COC
			| ChEMBL = 295026
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 7577		| ChemSpiderID = 7577
			| EC_number = 209-282-1
	| InChI = 1/C2H4O2/c1-4-2-3/h2H,1H3
			| PubChem = 7865
	| InChIKey = TZIHFWKZFHZASV-UHFFFAOYAI
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 1MPH591FTG
			| SMILES = O=COC
			| InChI = 1/C2H4O2/c1-4-2-3/h2H,1H3
			| InChIKey = TZIHFWKZFHZASV-UHFFFAOYAI
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C2H4O2/c1-4-2-3/h2H,1H3		| StdInChI = 1S/C2H4O2/c1-4-2-3/h2H,1H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = TZIHFWKZFHZASV-UHFFFAOYSA-N		| StdInChIKey = TZIHFWKZFHZASV-UHFFFAOYSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=2|H=4|O=2		| C=2 | H=4 | O=2
	| Density = 0.98 g/cm³		| Density = 0.98 g/cm<sup>3</sup>
			| Appearance = Colorless liquid
	| MeltingPtC = -100
			| Odor = pleasant<ref name=PGCH/>
	| BoilingPtC = 32
			| MeltingPtC = -100
			| BoilingPtC = 32
			| Solubility = 30% (20°C)<ref name=PGCH/>
			| VaporPressure = 634 hPa (476 mmHg) (20°C)<ref name=PGCH/>
			| MagSus = -32.0·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
			| GHS_ref=<ref>{{cite web |title=Methyl formate |url=https://pubchem.ncbi.nlm.nih.gov/compound/7865#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=19 December 2021 |language=en |archive-date=19 December 2021 |archive-url=https://web.archive.org/web/20211219231403/https://pubchem.ncbi.nlm.nih.gov/compound/7865#section=Safety-and-Hazards |url-status=live }}</ref>
	| EUClass = Highly flammable (F+); Harmful (Xn)}}
			| GHSPictograms = {{GHS02}}{{GHS07}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|224|302|319|332|335}}
			| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+312|303+361+353|304+312|304+340|305+351+338|312|330|337+313|370+378|403+233|403+235|405|501}}
			| IDLH = 4500 ppm<ref name=PGCH>{{PGCH|0417}}</ref>
			| REL = TWA 100 ppm (250 mg/m<sup>3</sup>) ST 150 ppm (375 mg/m<sup>3</sup>)<ref name=PGCH/>
			| PEL = TWA 100 ppm (250 mg/m<sup>3</sup>)<ref name=PGCH/>
			| LD50 = 1622 mg/kg (oral, rabbit)<ref name=IDLH>{{IDLH|107313|Methyl formate}}</ref>
			| NFPA-H = 2
			| NFPA-F = 4
			| NFPA-R = 0
			| NFPA-S =
			| FlashPtF = -2
			| FlashPt_ref = <ref name=PGCH/>
			| ExploLimits = 4.5%-23%<ref name=PGCH/>
			| LCLo = 50,000 ppm (guinea pig, 20 min)<ref name=IDLH/>
			}}
	}}		}}
			'''Methyl formate''', also called '''methyl methanoate''', is the methyl ] of ]. The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, high ], and low ]. It is a precursor to many other compounds of commercial interest.<ref name=Ullmann_2009>Werner Reutemann and Heinz Kieczka "Formic Acid" in ''Ullmann's Encyclopedia of Industrial Chemistry'' 2002, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a12_013}}</ref>
			==Production==
			In the laboratory, methyl formate can be produced by the ] of ] and ], as follows:
			:HCOOH + CH<sub>3</sub>OH → HCOOCH<sub>3</sub> + H<sub>2</sub>O
			Industrial methyl formate, however, is usually produced by the combination of ] and ] (]) in the presence of a strong base, such as ]:<ref name=Ullmann_2009/>
			]
			This process, practiced commercially by BASF among other companies gives 96% selectivity toward methyl formate. The ] for this process is sensitive to water, which can be present in the ] feedstock, which is commonly derived from ]. Very dry ] is, therefore, essential.<ref>W. Couteau, J. Ramioulle, US Patent US4216339</ref>
			==Uses==
			Methyl formate is used primarily to manufacture ], ], and ]. These compounds are precursors or building blocks for many useful derivatives.
			Because of its high ], it is used for quick-drying finishes and as a ] for some ] applications (for example Ecomate'''®''' manufactured by Foam Supplies Inc.)<ref>{{cite web |title=Ecomate |url=https://ecomatetechnology.com/ |website=Ecomate |publisher=Foam Supplies, Inc. |access-date=2023-06-14 |archive-date=2023-05-05 |archive-url=https://web.archive.org/web/20230505060732/https://ecomatetechnology.com/ |url-status=live }}</ref> and as a replacement for ]s, ]s, and ]s. Methyl formate has near zero ] and zero ] and a short atmospheric life of 3 days.<ref name="FoamAndBlow_Excerpt">{{cite book |last1=Wypych |first1=George |title=Handbook of foaming and blowing agents |date=2017 |publisher=ChemTec Publishing |location=Toronto |isbn=9781895198997 |pages=3-28 |chapter=2. Chemical Origin of Blowing Agents |quote=ECOLOGICAL IMPACT Atmospheric life, days: 3 Kyoto compliant: yes Montreal compliant: yes Global warming potential: <1.5 Ozone depletion potential: 0 |doi=10.1016/B978-1-895198-99-7.50004-0}}</ref>
			It is also used as an ].{{citation needed|date=December 2024}}
			A historical use of methyl formate, which sometimes brings it attention, was in refrigeration. Before the introduction of less-toxic refrigerants, methyl formate was used as an alternative to ] in domestic refrigerators, such as some models of the famous GE Monitor Top.
			==References==
			{{reflist}}
			==External links==
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			{{Molecules detected in outer space}}
			{{Esters}}
			{{Authority control}}
			{{DEFAULTSORT:Methyl Formate}}
			]
			]