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Revision as of 16:19, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 469654491 of page 1,3,5-Trioxane for the Chem/Drugbox validation project (updated: '').		Latest revision as of 11:40, 18 March 2024 edit Project Osprey (talk | contribs)Extended confirmed users9,958 edits →Uses: more stable
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			{{redirect|Trioxin|the fictional chemical|Return of the Living Dead (film series)}}
	{{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
			| Watchedfields = changed
	| verifiedrevid = 443340901		| verifiedrevid = 477204812
	| Name = 1,3,5-Trioxane		| Name = 1,3,5-Trioxane
	| ImageFile = S-Trioxane.svg		| ImageFileL1 = S-Trioxane.svg
			| ImageFileR1 = 1,3,5-Trioxane-3D-balls.png
	| ImageSize = 100px
	| IUPACName = 1,3,5-Trioxane		| ImageAltR1 = Trioxane molecule
			| ImageSizeR1 = 140
	| OtherNames = ''s''-Trioxane		| PIN = 1,3,5-Trioxane
	1,3,5-Trioxacyclohexane
			| OtherNames = ''s''-Trioxane; 1,3,5-Trioxacyclohexane; Trioxymethylene; Metaformaldehyde; Trioxin
	Trioxymethylene
		⚫	|Section1={{Chembox Identifiers
	Metaformaldehye
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
	Trioxin
		⚫	| CASNo = 110-88-3
⚫	| Section1 = {{Chembox Identifiers
			| Beilstein = 102769
⚫	| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| UNII = 46BNU65YNY
⚫	| SMILES = O1COCOC1
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 38043		| ChEBI = 38043
			| ChEMBL = 1495792
	| ChemSpiderID = 7790		| ChemSpiderID = 7790
			| EINECS = 203-812-5
	| InChI = 1/C3H6O3/c1-4-2-6-3-5-1/h1-3H2
			| Gmelin = 2230
	| InChIKey = BGJSXRVXTHVRSN-UHFFFAOYAW
			| PubChem = 8081
		⚫	| RTECS = YK0350000
			| UNNumber = 1325
		⚫	| UNII_Ref = {{fdacite|correct|FDA}}
		⚫	| UNII = 46BNU65YNY
		⚫	| SMILES = O1COCOC1
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C3H6O3/c1-4-2-6-3-5-1/h1-3H2		| StdInChI = 1S/C3H6O3/c1-4-2-6-3-5-1/h1-3H2
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = BGJSXRVXTHVRSN-UHFFFAOYSA-N		| StdInChIKey = BGJSXRVXTHVRSN-UHFFFAOYSA-N
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
⚫	| CASNo = 110-88-3
⚫	| RTECS = YK0350000
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=3 | H=6 | O=3
	| Formula = C<sub>3</sub>H<sub>6</sub>O<sub>3</sub>
		⚫	| Appearance = White crystalline solid
	| MolarMass = 90.08 g/mol
			| Density = 1.17 g/cm{{sup|3}} (65 °C)<ref name=GESTIS>{{GESTIS|ZVG=29710}}</ref>
⚫	| Appearance = white crystalline solid
	| Density = 1.17 g/cm³ (65 °C)		| Solubility = 221 g/L<ref name=GESTIS/>
			| MeltingPtC = 62
	| Solubility = 17.2 g/100 ml (18 °C)
			| MeltingPt_ref = <ref name=GESTIS/>
	| MeltingPt = 64 °C
	| BoilingPt = 114.5 °C		| BoilingPtC = 115
			| BoilingPt_ref = <ref name=GESTIS/>
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt = 45 °C		| FlashPtC = 45<ref name=GESTIS/>
	| NFPA-H = 2		| NFPA-H = 2
	| NFPA-F = 2		| NFPA-F = 2
	| NFPA-R = 0		| NFPA-R = 0
			| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
	| RPhrases = 22
			| GHSSignalWord = Warning
	| SPhrases = 24/25
			| HPhrases = {{H-phrases|228|335|361d}}
			| PPhrases = {{P-phrases|201|202|210|240|241|261|271|280|281|304+340|308+313|312|370+378|403+233|405|501}}
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
			| OtherCompounds = {{unbulleted list|]|]|]|]}}
⚫	| OtherCpds = ]
	]
	]
	}}		}}
	}}		}}
			'''1,3,5-Trioxane''', sometimes also called '''trioxane''' or '''trioxin''', is a ] with ] C{{sub|3}}H{{sub|6}}O{{sub|3}}. It is a white, highly water-soluble solid with a ]-like odor. It is a stable cyclic ] of ], and one of the three ] isomers; its molecular backbone consists of a six-membered ring with three ] atoms alternating with three ] atoms.
			==Production==
			Trioxane can be obtained by the acid-] cyclic trimerization of formaldehyde in concentrated aqueous solution.<ref name=Ullmann/>
			:]
			== Uses ==
			Trioxane can be used interchangeably with formaldehyde and with paraformaldehyde,<ref>{{cite journal |doi=10.15227/orgsyn.075.0189|title=6,7-Dihydrocyclopenta-1,3-Dioxin-5(4H)-One|journal=Organic Syntheses|year=1998|volume=75|pages=189|author=K. Chen|author2=C. S. Brook|author3=A. B. Smith, III}}</ref><ref>{{cite journal |doi=10.15227/orgsyn.052.0016|title=Benzyl Chloromethyl Ether|journal=Organic Syntheses|year=1972|volume=52|pages=16|author=D. S. Connor|author2=G. W. Klein|author3=G. N. Taylor|author4=R. K. Boeckman, Jr|author5=J. B. Medwid}}</ref> however the cyclic structure is more stable and it can require high temperatures in order to react. It is a precursor for the production of ]s, of which about one million tons per year are produced.<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a11_619|title=Formaldehyde|year=2000|last1=Reuss|first1=Günther|last2=Disteldorf|first2=Walter|last3=Gamer|first3=Armin Otto|last4=Hilt|first4=Albrecht|isbn=3527306730}}</ref> Other applications exploit its tendency to release formaldehyde. As such it is used as a binder in textiles, wood products, etc. Trioxane is combined with ] and compressed into solid bars to make ]s, used by the ] and ] as a cooking fuel.
			In the laboratory, trioxane is used as an anhydrous source of formaldehyde.<ref>{{cite journal|doi=10.15227/orgsyn.030.0051|title=Hexahydro-1,3,5-Tripropionyl-s-Triazine|journal=Organic Syntheses|year=1950|volume=30|pages=51|author=W. O. Teeters|author2=M. A. Gradsten}}</ref>
			== See also ==
		⚫	* ]
			* ]
			* ]
			* ]
			== References ==
			{{reflist}}
			{{DEFAULTSORT:Trioxane, 1, 3, 5-}}
			]
			]