| 词条 | Formamide |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443825387 | Name = Formamide | ImageFile = Formamide-2D.png | ImageFile_Ref = {{chemboximage|correct|??}} | ImageName = Structural formula of the formamide molecule | ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1 = Formamide-3D-balls.png | ImageNameL1 = Ball and stick model of formamide | ImageFileR1 = Formamide-3D-vdW.png | ImageNameR1 = Space-filling model of the formamide molecule | PIN = Formamide[1] | SystematicName = Methanamide | OtherNames = Carbamaldehyde |Section1={{Chembox Identifiers | IUPHAR_ligand = 4739 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 693 | PubChem = 713 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C00488 | InChI = 1/CH3NO/c2-1-3/h1H,(H2,2,3) | InChIKey = ZHNUHDYFZUAESO-UHFFFAOYAQ | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 266160 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/CH3NO/c2-1-3/h1H,(H2,2,3) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ZHNUHDYFZUAESO-UHFFFAOYSA-N | CASNo = 75-12-7 | CASNo_Ref = {{cascite|correct|CAS}} | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 48431 | SMILES = O=CN }} |Section2={{Chembox Properties | Formula = CH3NO | MolarMass = 45.04 g/mol | Density = 1.133 g/cm3 | Appearance = Colorless, oily liquid[2] | MeltingPtC = 2 to 3 | BoilingPtC = 210 | VaporPressure = 0.08 mmHg at 20 °C | Solubility = Miscible | MagSus = {{val|-2.19|e=-5|u=cm3/mol}} | pKa = 23.5 (in DMSO)[2] |Section7={{Chembox Hazards | FlashPtC = 154 | FlashPt_notes = (closed cup) | NFPA-F = 1 | NFPA-H = 2 | NFPA-R = 0 | PEL = none[3] | IDLH = N.D.[3] | REL = TWA 10 ppm (15 mg/m3) [skin][3] |Section8={{Chembox Related | OtherCompounds = Carbamic acid Dimethylformamide}} }}Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs, other pharmaceuticals, herbicides, pesticides and the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers.[4] Formamides are compounds of the type RR′NCHO. One important formamide is dimethylformamide, (CH3)2NCHO. ProductionHistorical productionIn the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yields formamide upon heating:[5] HCOOH + NH3 → HCOO−{{chem|NH|4|+}} HCOO−{{chem|NH|4|+}} → HCONH2 + H2O Formamide is also generated by aminolysis of ethyl formate:[6] HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH Modern productionThe current industrial process for the manufacture of formamide involves either the carbonylation of ammonia:[4] CO + NH3 → HCONH2 An alternative two-stage process involves the ammonolysis of methyl formate, which is formed from carbon monoxide and methanol: CO + CH3OH → HCOOCH3 HCO2CH3 + NH3 → HCONH2 + CH3OH ApplicationsFormamide is used in the industrial production of hydrogen cyanide. It is also used as a solvent for processing various polymers such as polyacrylonitrile.[11] ReactionsFormamide decomposes into carbon monoxide and ammonia at 180 °C. HCONH2 → CO + NH3 Traces of hydrogen cyanide (HCN) and water are also observed. In the presence of solid acid catalysts, formamide dehydrates to HCN:[7] HC(O)NH2 → HCN + H2O Niche or laboratory applicationsFormamide is a constituent of cryoprotectant vitrification mixtures used for cryopreservation of tissues and organs. Formamide is also used as an RNA stabiliser in gel electrophoresis by deionizing RNA. In capillary electrophoresis, it is used for stabilizing (single) strands of denatured DNA. Another use is to add it in sol-gel solutions in order to avoid cracking during sintering. Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms.[8] Formamide is used to prepare primary amines directly from ketones via their N-formyl derivatives, using the Leuckart reaction. BiochemistryFormamides are intermediates in the methanogenesis cycle. Prebiotic chemistry{{Main article|Hypothetical types of biochemistry}}Formamide has been proposed as an alternative solvent to water, perhaps with the ability to support life with alternative biochemistries to that currently found on Earth. It forms by the hydrolysis of hydrogen cyanide. With a large dipole moment, its solvation properties are similar to those of water.[10] Formamide has been shown to convert to traces of guanine upon heating in the presence of ultraviolet light.[11] SafetyFormamide is moderately irritating to the eyes, skin and mucous membranes.[12] Inhalation of large amounts of formamide vapor may require medical attention.[13][14] It is also a teratogen.[15] Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption.[16] Formamide should never be handled without proper safety attire including gloves and goggles. References1. ^{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 841 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The traditional name ‘formamide’ is retained for HCO-NH2 and is the preferred IUPAC name.}} {{Molecules detected in outer space}}{{Authority control}}2. ^{{cite journal |author1=F. G. Bordwell |author2=J. E. Bartmess |author3=J. A. Hautala | title = Alkyl effects on equilibrium acidities of carbon acids in protic and dipolar aprotic media and the gas phase | year = 1978 | journal = J. Org. Chem. | volume = 43 | issue = 16 | pages = 3095–3101 | doi = 10.1021/jo00410a001}} 3. ^1 2 3 {{PGCH|0295}} 4. ^1 {{cite book |last1=Hohn |first1=A. |editor1-first= Jacqueline I. |editor1-last= Kroschwitz |title=Kirk-Othmer Concise Encylclopedia of Chemical Technology |edition=4th |year=1999 |publisher= John Wiley & Sons, Inc.|location=New York|isbn=978-0471419617|pages=943–944 |chapter=Formamide}} 5. ^{{cite journal|last1=Lorin|first1=M.|title=Preparation of Formamide by means of Formiates and Oxalates|journal=The Chemical News and Journal of Physical Science|date=1864|volume=IX|page=291|url=https://books.google.com/books?id=7eQEAAAAQAAJ&pg=RA1-PA291&dq=Preparation+of+formamide+by+means+of&hl=en&sa=X&ei=7_ybU82_NcnroASw1ICICA&ved=0CDwQ6AEwAg#v=onepage&q=Preparation%20of%20formamide%20by%20means%20of&f=false|accessdate=14 June 2014}} 6. ^{{cite journal|last1=Phelps|first1=I. K.|last2=Deming|first2=C. D.|title=The Preparation of Formamide from Ethyl Formate and Ammonium Hydroxide|journal=The Chemical News and Journal of Physical Science|date=1908|volume=97|pages=86–87|url=https://books.google.com/books?id=FhlLAAAAYAAJ&pg=PA86&dq=The+Preparation+of+Formamide+from+Ethyl+Formate+and+Ammonium+Hydroxide&hl=en&sa=X&ei=9P6bU_GzJ8H8oAT4toCIDg&ved=0CCoQ6AEwAA#v=onepage&q=The%20Preparation%20of%20Formamide%20from%20Ethyl%20Formate%20and%20Ammonium%20Hydroxide&f=false|accessdate=14 June 2014}} 7. ^1 {{Ullmann|author=Bipp, H.; Kieczka, H.|title=Formamides|year=2012|doi=10.1002/14356007.a12_001.pub2}} 8. ^{{cite journal |author1=Vimal K. Kamineni |author2=Yuri M. Lvov |author3=Tabbetha A. Dobbins | title = Layer-by-Layer Nanoassembly of Polyelectrolytes Using Formamide as the Working Medium | journal = Langmuir | volume = 23 | issue = 14 | pages = 7423–7427 | year = 2007 | doi = 10.1021/la700465n | pmid = 17536845}} 9. ^{{cite journal|author=Thauer, R. K.|title=Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson|journal=Microbiology|year=1998|volume=144|pages=2377–2406|doi=10.1099/00221287-144-9-2377}} 10. ^{{cite book |last1= Committee On The Limits Of Organic Life In Planetary Systems |title=The Limits of Organic Life in Planetary Systems |url= http://www.nap.edu/catalog.php?record_id=11919 |accessdate=2012-08-29 |year=2007 |publisher=The National Academies Press |location= Washington, DC |isbn=0-309-66906-5 |page=74}} 11. ^{{cite web | url = https://www.sciencedaily.com/releases/2010/06/100614101957.htm | title = Origin of Life: Adding UV Light Helps Form 'Missing G' of RNA Building Blocks | publisher = Science Daily | date = June 14, 2010}} 12. ^TOXNet Formamide HSDB: Formamide 13. ^{{cite journal | author=Warheit DB, Kinney LA, Carakostas MC, Ross PE | title=Inhalation toxicity study of formamide in rats | journal=Fundamental and Applied Toxicology | volume=13 | issue=4 | year=1989 | pages=702–713 |id= | pmid=2620791 | doi=10.1093/toxsci/13.4.702}} 14. ^MSDS for formamide, hazard.com 15. ^Lab use of formamide, University of Bath 16. ^ ECHA Formamide 2 : Formamides|Amide solvents |
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