Methyl formate
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477501961
| Name = Methyl formate
| ImageFileL1 = Methyl formate.png
| ImageSizeL1 = 150
| ImageNameL1 = Structural formula of methyl formate
| ImageFileR1 = Methyl-formate-3D-balls.png
| ImageSizeR1 = 150
| ImageNameR1 = Ball-and-stick model of the methyl formate molecule
| ImageFile2 = Commercial methyl formate.jpg
| PIN = Methyl formate
| SystematicName = Methyl methanoate
| OtherNames = R-611
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 107-31-3
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 77699
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 295026
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7577
| EC_number = 209-282-1
| PubChem = 7865
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TZIHFWKZFHZASV-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=2 | H=4 | O=2
| Density = 0.98 g/cm3
| Appearance = Colorless liquid
| MeltingPtC = -100
| BoilingPtC = 32
| VaporPressure = 634 hPa (476 mmHg) (20°C)
| MagSus = −32.0·10−6 cm3/mol
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://msds.chem.ox.ac.uk/ME/methyl_formate.html Oxford MSDS]
| 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{{PGCH|0417}}
| REL = TWA 100 ppm (250 mg/m3) ST 150 ppm (375 mg/m3)
| PEL = TWA 100 ppm (250 mg/m3)
| LD50 = 1622 mg/kg (oral, rabbit){{IDLH|107313|Methyl formate}}
| NFPA-H = 2
| NFPA-F = 4
| NFPA-R = 0
| NFPA-S =
| FlashPtF = -2
| LCLo = 50,000 ppm (guinea pig, 20 min)
}}
}}
Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.Werner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a12_013}}
Production
In the laboratory, methyl formate can be produced by the condensation reaction of methanol and formic acid, as follows:
:HCOOH + CH3OH → HCOOCH3 + H2O
Industrial methyl formate, however, is usually produced by the combination of methanol and carbon monoxide (carbonylation) in the presence of a strong base, such as sodium methoxide:
File:Industrial synthesis of methyl formate.svg
This process, practiced commercially by BASF among other companies gives 96% selectivity toward methyl formate. The catalyst for this process is sensitive to water, which can be present in the carbon monoxide feedstock, which is commonly derived from synthesis gas. Very dry carbon monoxide is, therefore, essential.W. Couteau, J. Ramioulle, US Patent US4216339
Uses
Methyl formate is used primarily to manufacture formamide, dimethylformamide, and formic acid. These compounds are precursors or building blocks for many useful derivatives.
Because of its high vapor pressure, it is used for quick-drying finishes and as a blowing agent for some polyurethane foam applications (for example Ecomate® manufactured by Foam Supplies Inc.){{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 }} and as a replacement for CFCs, HCFCs, and HFCs. Methyl formate has near zero ozone depletion potential and zero global warming potential and a short atmospheric life of 3 days.{{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}}
It is also used as an insecticide.{{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 sulfur dioxide in domestic refrigerators, such as some models of the famous GE Monitor Top.
References
{{reflist}}
External links
- [http://webbook.nist.gov/cgi/cbook.cgi?ID=107-31-3&Units=SI&cMS=on NIST Chemistry WebBook: Methyl formate]
- [https://archive.today/20130119004650/http://www.chemicalland21.com/arokorhi/industrialchem/organic/METHYL%20FORMATE.htm ChemicalLand21.com entry on METHYL FORMATE]
- [https://www.cdc.gov/niosh/npg/npgd0417.html CDC - NIOSH Pocket Guide to Chemical Hazards]
{{Molecules detected in outer space}}
{{Esters}}
{{Authority control}}
{{DEFAULTSORT:Methyl Formate}}