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	{{DISPLAYTITLE:''tert''-Amyl methyl ether}}		{{DISPLAYTITLE:''tert''-Amyl methyl ether}}
			{{distinguish|tert-Amyl ethyl ether}}
	{{chembox		{{chembox
		⚫	| verifiedrevid = 458038308
	| Watchedfields = changed
		⚫	| Reference = <ref name="chemicalland21">{{cite web |title=tert-AMYL METHYL ETHER (1,1-DIMETHYLPROPYL METHYL ETHER) |work=chemicalland21.com |url=http://chemicalland21.com/industrialchem/solalc/tert-AMYL%20METHYL%20ETHER.htm |access-date=2009-10-20}}</ref><ref name="nicnas">{{cite web |author=National Industrial Chemicals Notification and Assessment Scheme |work=Full Public Reports |title=''t''-Amyl methyl ether (TAME) |year=2001 |url=http://www.nicnas.gov.au/publications/car/new/na/nafullr/na0800fr/na878fr.pdf |access-date=2009-10-20}}</ref>
⚫	| verifiedrevid = 414124658
		⚫	| Name = ''tert''-Amyl methyl ether
⚫	| Reference = <ref name="chemicalland21">{{cite web |title=tert-AMYL METHYL ETHER (1,1-DIMETHYLPROPYL METHYL ETHER) |work=chemicalland21.com |url=http://chemicalland21.com/industrialchem/solalc/tert-AMYL%20METHYL%20ETHER.htm |accessdate=2009-10-20}}</ref><ref name="nicnas">{{cite web |author=National Industrial Chemicals Notification and Assessment Scheme |work=Full Public Reports |title=''t''-Amyl methyl ether (TAME) |year=2001 |url=http://www.nicnas.gov.au/publications/car/new/na/nafullr/na0800fr/na878fr.pdf |accessdate=2009-10-20| format=PDF}}</ref>
			| ImageFileL1 = Tert-amyl_methyl_ether.svg
⚫	| Name = ''tert''-Amyl methyl ether
	| ImageFileL1 = TAME.png		| ImageFileR1 = Amyl methyl ether.png
		⚫	| PIN = 2-Methoxy-2-methylbutane
	| ImageSizeL1 = 120px
	| ImageFileR1 = Amyl methyl ether.png		| OtherNames = ''tertiary''-Amyl methyl ether; TAME; Methoxypentane
		⚫	| Section1 = {{Chembox Identifiers
	| ImageSizeR1 = 120px
		⚫	| Abbreviations = TAME
⚫	| IUPACName = 2-methoxy-2-methylbutane
			| CASNo_Ref = {{cascite|correct|CAS}}
⚫	| Section1 = {{Chembox Identifiers
		⚫	| CASNo = 994-05-8
⚫	| Abbreviations = TAME
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| CASNo = 994-05-8
	| PubChem = 61247		| UNII = 94525J1AP8
	| ChemSpiderID = 55188		| PubChem = 61247
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫	| SMILES = O(C(C)(C)CC)C
			| ChemSpiderID = 55188
⚫	| InChI = 1/C6H14O/c1-5-6(2,3)7-4/h5H2,1-4H3
		⚫	| SMILES = O(C(C)(C)CC)C
⚫	| InChIKey = HVZJRWJGKQPSFL-UHFFFAOYAC
	| StdInChI = 1S/C6H14O/c1-5-6(2,3)7-4/h5H2,1-4H3		| InChI = 1/C6H14O/c1-5-6(2,3)7-4/h5H2,1-4H3
	| StdInChIKey = HVZJRWJGKQPSFL-UHFFFAOYSA-N		| InChIKey = HVZJRWJGKQPSFL-UHFFFAOYAC
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChI = 1S/C6H14O/c1-5-6(2,3)7-4/h5H2,1-4H3
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	| StdInChIKey = HVZJRWJGKQPSFL-UHFFFAOYSA-N
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| C = 6		| C = 6
	| H = 14		| H = 14
	| O = 1		| O = 1
	| Appearance = Clear, colorless liquid		| Appearance = Clear, colorless liquid
	| MeltingPtC = -80		| MeltingPtC = -80
	| BoilingPtC = 86.3		| BoilingPtC = 86.3
	| Solubility = 10.71 g/L at 20 °C		| Solubility = 10.71 g/L at 20 °C
	| Viscosity = Low		| RefractIndex = 1.3896
			| Density = 0.76-0.78 g/mL<ref>{{Cite web | url = https://www.sigmaaldrich.com/catalog/product/aldrich/283096 | publisher = ] | title = tert-Amyl methyl ether }}</ref>
	| RefractIndex = 1.3896
	| Density = 3.52 (vapor)
	}}		}}
	| Section3 = {{Chembox Hazards		| Section3 = {{Chembox Hazards
	| FlashPt = -11 °C		| FlashPtC = -11
	| Autoignition = 430 °C		| AutoignitionPtC = 430
	| ExploLimits = Upper Explosive Limit = 7.1 % Lower Explosive Limit = 1.0		| ExploLimits = 1.0-7.1%
	}}		}}
			| Section4 =
	}}		}}
			'''''tert''-Amyl methyl ether''' ('''TAME''') is an ] used as a fuel oxygenate. TAME derives from C5 distillation fractions of ].<ref name=":0">{{Cite journal|last1=Prat|first1=Denis|last2=Wells|first2=Andy|last3=Hayler|first3=John|last4=Sneddon|first4=Helen|last5=McElroy|first5=C. Robert|last6=Abou-Shehada|first6=Sarah|last7=Dunn|first7=Peter J.|date=2015-12-21|title=CHEM21 selection guide of classical- and less classical-solvents|journal=Green Chem.|language=en|volume=18|issue=1|pages=288–296|doi=10.1039/c5gc01008j|issn=1463-9270|doi-access=free}}</ref> It has an ethereous ].<ref name="chemicalland21" /> Unlike most ethers, it does not require a stabilizer as it does not form ] on storage.<ref>{{Cite book|title=Oxygenates in Gasoline|last1=Diaz|first1=Arthur F.|last2=Drogos|first2=Donna L.|date=2001-11-06|publisher=American Chemical Society|isbn=978-0841237605|series=ACS Symposium Series|volume=799|pages=138–152|doi=10.1021/bk-2002-0799.ch010}}</ref>
	'''''tert''-Amyl methyl ether''' (TAME) is an ] used as a fuel oxygenate. It has an ethereous ].<ref name="chemicalland21" /> Unlike most ethers, does not form peroxides on storage.
			Other names:<ref name=":1">{{Cite web |last=PubChem |title=tert-Amyl methyl ether |url=https://pubchem.ncbi.nlm.nih.gov/compound/61247 |access-date=2023-10-22 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
			* 2-Methoxy-2-methylbutane
			* Butane, 2-methoxy-2-methyl-
			* 1,1-Dimethylpropyl methyl ether
			* Methyl tert-pentyl ether
			* Methyl tert-Amyl ether
			* 2-Methyl-2-methoxybutane
			* Methyl 2-methyl-2-butyl ether
			* tert-Pentyl methyl ether
			* Tertiary amyl methyl ether
			* Methyl 1,1-dimethylpropyl ether
			* 2-Methoxy-2-methylbutane
	==Uses==		==Uses==
	TAME is mostly used as an ] to gasoline. It is added for three reasons: to increase ] enhancement, to replace banned ], and to raise the ] content in ]. It is known that TAME in fuel reduces ] ] of some volatile organic compounds.<ref name="chemicalland21" />		TAME is mostly used as an ] to gasoline. It is added for three reasons: to increase ] enhancement, to replace banned ], and to raise the ] content in ]. It is known that TAME in fuel reduces ] ] of some ].<ref name="chemicalland21" />
			TAME is also used as a solvent in ] as a more environmentally friendly alternative to some of the classic ether solvents.<ref name=":0" /> It is characterized by a high boiling point (86°C) and a low freezing point (&minus;80°C), allowing a wide range of reaction temperatures. TAME can be used as a safe reaction medium (e.g. ]s, ], such as ]s and ]s, as well as metal hydride reductions) and as an extraction solvent to replace ], aromatics, and other ethers.<ref>{{Cite web|url=https://www.ineos.com/businesses/ineos-oligomers/products/ |archive-url=https://web.archive.org/web/20171107020216/https://www.ineos.com/businesses/ineos-oligomers/products/ |archive-date=2017-11-07 |title=INEOS Oligomers Products |website=INEOS |language=en|access-date=2017-10-30}}</ref>{{Failed verification|date=December 2022}}
			A series of experiments were carried out in a batch reactor at the temperature range of 313-343 K to study the synthesis of ''tert''-amyl ethyl ether from ethanol (EtOH) and 2-methyl-1-butene (2M1B) catalyzed by the ]. The suitable reaction pressure was obtained by using the method of the ]. The activity coefficients of each component were accurately calculated using the Wilson method, then, the equilibrium constants was obtained. The effect of catalyst size, stirring rate, temperature and EtOH/2M1B molar ratio was investigated at the chosen pressure, respectively. A kinetic model which considered the variation of each component volume was established. The method of nonlinear least square combined with genetic algorithm (NLS-GA) was proposed to estimate the kinetic constant in the forward direction. Results indicated that simulated kinetics results were agreed well with the experimental data.
	==Toxicity==		==Toxicity==
			{{Expand section|date=July 2015}}
	When exposed to lab rats at 4000 ppm only 25% survived, the rats that died, died of ].<ref>{{cite journal |journal=Toxicology Letters |volume=82-83 |date=December 1995 |pages=719–724 |booktitle=Proceedings of the International Congress of Toxicology - VII |title=Health effects of inhaled tertiary amyl methyl ether and ethyl tertiary butyl ether |first1=Russell D. |pmid=8597132 |last1=White |first2=Wayne C. |last2=Daughtrey |first3=Mike S. |last3=Wells |doi=10.1016/0378-4274(95)03590-7}}</ref>
			TAME was evaluated in 4-week rat inhalation studies sponsored by Amoco Corporation. Target vapor concentrations were 0, 500, 2000, or 4000 ppm for 6 h per day, 5 days per week, for 4 weeks. Exposure at 4000 ppm resulted in 25% mortality, apparently as a consequence of severe ]. Body weight gain was decreased in the TAME high dose male rats. Significant effects on ] (FOB) parameters were only found in the high and mid-dose groups immediately after exposure. All affected FOB parameters were normal by the next day. TAME exposure significantly increased relative liver weights in the high and mid-dose groups. However, no treatment-related histopathologic findings were noted for the compound. Clinical chemistry and hematology findings were minimal with TAME exposure. The results indicate that 500 ppm was a ] for TAME in these studies.<ref>{{cite journal |last1=White |first1=Russell D. |last2=Daughtrey |first2=Wayne C. |last3=Wells |first3=Mike S. |date=December 1995 |title=Health effects of inhaled tertiary amyl methyl ether and ethyl tertiary butyl ether |url=https://pubmed.ncbi.nlm.nih.gov/8597132/ |journal=] |volume=82-83 |pages=719–724 |doi=10.1016/0378-4274(95)03590-7 |pmid=8597132}}</ref>
			== Some other properties<ref name=":1" /> ==
			Relative vapor density (air = 1): 3.6
			Vapor Pressure 75.2
			log Kow = 1.55 at 20 °C
			Henry's Law constant = 1.32X10-3 atm-cu m/mol at 25 °C
			Stability / Shelf Life: Stable under recommended storage conditions.
			Autoignition Temperature: 415 °C
			Decomposition: When heated to decomposition it emits acrid smoke and irritating vapors.
			Odor Threshold: 0.02
			=== ] ===
			Standard non-polar 672.5, 674, 673, 669.3, 666
			Semi-standard non-polar 678, 655, 668.3
			Standard polar 790, 802.9
	==See also==		==See also==
	*]		*]
	*]		*]
			*]
	== References ==		== References ==
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	{{DEFAULTSORT:Amyl Methyl Ether, Tert-}}		{{DEFAULTSORT:Amyl Methyl Ether, Tert-}}
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