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	{{chembox		{{chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 393201977		| verifiedrevid = 421482767
	|ImageFile=Triethoxymethane.svg		| ImageFile = Triethoxymethane.svg
	|ImageSize=180px		| ImageSize = 180px
			| ImageAlt = Structural formula
	|IUPACName=Diethoxymethoxyethane
			| ImageFile1 = Triethyl-orthoformate-3D-balls.png
⚫	|OtherNames=Triethoxymethane; Ethyl orthoformate
			| ImageSize1 = 180
			| ImageAlt1 = Ball-and-stick model
			| PIN=(Diethoxymethoxy)ethane
		⚫	| OtherNames=Triethoxymethane; Ethyl orthoformate
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=122-51-0		| CASNo=122-51-0
	| PubChem=31214		| PubChem=31214
			| EC_number = 204-550-4
⚫	| SMILES=CCOC(OCC)OCC
			| UNNumber = 2524
			| UNII = 355LRR361Q
			| ChEMBL = 1476236
		⚫	| SMILES=CCOC(OCC)OCC
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 28955
			| InChI = 1/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3
			| InChIKey = GKASDNZWUGIAMG-UHFFFAOYAW
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = GKASDNZWUGIAMG-UHFFFAOYSA-N
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| C = 7 | H = 16 | O = 3		| C=7 | H=16 | O=3
	| Appearance=		| Appearance=
	| Density=0.891 g/mL		| Density=0.891 g/mL
	| MeltingPtC= -76		| MeltingPtC= -76
	| BoilingPtC= 146		| BoilingPtC= 146
	| Solubility=		| Solubility=
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
			| GHSPictograms = {{GHS02}}{{GHS07}}
⚫	| ExternalMSDS =
			| GHSSignalWord = Warning
⚫	| FlashPt=
			| HPhrases = {{H-phrases|226|315|319|335}}
	| Autoignition=
			| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|280|302+352|303+361+353|304+340|305+351+338|312|321|332+313|337+313|362|370+378|403+233|403+235|405|501}}
		⚫	| ExternalSDS =
		⚫	| FlashPt=
			| AutoignitionPt =
	}}		}}
	}}		}}
	'''Triethyl orthoformate''' is an ] of ]. It is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol<ref>Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288</ref>.		'''Triethyl orthoformate''' is an ] with the formula HC(OC<sub>2</sub>H<sub>5</sub>)<sub>3</sub>. This colorless volatile liquid, the ] of ], is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol.<ref>Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288</ref>
	It may also be prepared from the reaction of ] and ]:<ref>{{OrgSynth | title = Ethyl orthoformate | author = W. E. Kaufmann and E. E. Dreger | prep = CV1P0258 | collvol =1 | collvolpages = 258 | year = 1941}}</ref>		It may also be prepared from the reaction of ], formed ] from ] and absolute ], and ]:<ref>{{OrgSynth | title = Ethyl orthoformate | author = W. E. Kaufmann and E. E. Dreger | prep = CV1P0258 | collvol =1 | collvolpages = 258 | year = 1941}}</ref>
	: CHCl<sub>3</sub> + 3 Na + 3 EtOH &rarr; HC(OEt)<sub>3</sub> + <sup>3</sup>/<sub>2</sub> H<sub>2</sub> + 3 NaCl		: CHCl<sub>3</sub> + 3 Na + 3 EtOH → HC(OEt)<sub>3</sub> + {{frac|3|2}} H<sub>2</sub> + 3 NaCl
	Triethyl orthoformate participates in the ], for example:<ref>{{OrgSynth | title = ''n''-Hexaldehyde | author = G. Bryant Bachman | collvol = 2 | collvolpages = 323 | year = 1943 | prep = CV2P0323}}</ref>		Triethyl orthoformate is used in the ], for example:<ref name=synth>{{OrgSynth | title = ''n''-Hexaldehyde | author = G. Bryant Bachman | collvol = 2 | collvolpages = 323 | year = 1943 | prep = CV2P0323}}</ref>
			: RMgBr + HC(OC<sub>2</sub>H<sub>5</sub>)<sub>3</sub> → RC(H)(OC<sub>2</sub>H<sub>5</sub>)<sub>2</sub> + MgBr(OC<sub>2</sub>H<sub>5</sub>)
			: RC(H)(OC<sub>2</sub>H<sub>5</sub>)<sub>2</sub> + H2O → RCHO + 2 C<sub>2</sub>H<sub>5</sub>OH
			In ], it is used to convert ]es to the corresponding ethanol complexes:<ref>Willem L. Driessen, Jan Reedijk "Solid Solvates: The Use of Weak Ligands in Coordination Chemistry" Inorg. Synth., 1992, Vol. 29,111–118. {{doi|10.1002/9780470132609.ch27}}</ref>
	:]
			:(BF<sub>4</sub>)<sub>2</sub> + 6 HC(OC<sub>2</sub>H<sub>5</sub>)<sub>3</sub> → (BF<sub>4</sub>)<sub>2</sub> + 6 HC(O)(OC<sub>2</sub>H<sub>5</sub>) + 6 HOC<sub>2</sub>H<sub>5</sub>
			Triethyl orthoformate (TEOF) is an excellent reagent for converting compatible carboxylic acids to ethyl esters. Such carboxylic acids, refluxed neat in excess TEOF until low-boilers cease evolution, are quantitatively converted to the ethyl esters, without need for extraneous catalysis.<ref>{{Cite journal|last=Paine|first=John B.|date=July 2008|title=Esters of Pyromellitic Acid. Part I. Esters of Achiral Alcohols: Regioselective Synthesis of Partial and Mixed Pyromellitate Esters, Mechanism of Transesterification in the Quantitative Esterification of the Pyromellitate System Using Orthoformate Esters, and a Facile Synthesis of the Ortho Pyromellitate Diester Substitution Pattern|url=http://dx.doi.org/10.1021/jo800543w|journal=The Journal of Organic Chemistry|volume=73|issue=13|pages=4929–4938|doi=10.1021/jo800543w|pmid=18522420 |issn=0022-3263}}</ref> Alternatively, added to ordinary esterifications using catalytic acid and ethanol, TEOF helps drive esterification to completion by converting the byproduct water formed to ethanol and ethyl formate.
	==See also==		==See also==
	* ]		*]
	* ]
	==References==		==References==
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