| Revision as of 10:12, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473089718 of page 2,2-Di-2-furylpropane for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 14:41, 28 October 2022 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Furans; added Category:2-Furyl compounds using HotCat |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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| verifiedrevid = 477343263 |
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| ImageFile = 2,2-Di-2-furylpropane.png |
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| ImageFile = 2,2-Di-2-furylpropane.png |
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| IUPACName = 2,2’-propane-2,2-diyldifuran |
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| PIN = 2,2′-(Propane-2,2-diyl)difuran |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = <!-- blanked - oldvalue: 17920-88-6 --> |
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| PubChem = 595339 |
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| CASNo = 17920-88-6 |
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| ChemSpiderID = 517526 |
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| PubChem = 595339 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = o1c(ccc1)C(c2occc2)(C)C |
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| ChemSpiderID = 517526 |
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| InChI = 1/C11H12O2/c1-11(2,9-5-3-7-12-9)10-6-4-8-13-10/h3-8H,1-2H3 |
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| SMILES = o1c(ccc1)C(c2occc2)(C)C |
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| InChIKey = OFBSTYYRPIFDPM-UHFFFAOYAD |
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| StdInChI = 1S/C11H12O2/c1-11(2,9-5-3-7-12-9)10-6-4-8-13-10/h3-8H,1-2H3 |
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| InChI = 1/C11H12O2/c1-11(2,9-5-3-7-12-9)10-6-4-8-13-10/h3-8H,1-2H3 |
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| StdInChIKey = OFBSTYYRPIFDPM-UHFFFAOYSA-N |
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| InChIKey = OFBSTYYRPIFDPM-UHFFFAOYAD |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C11H12O2/c1-11(2,9-5-3-7-12-9)10-6-4-8-13-10/h3-8H,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = OFBSTYYRPIFDPM-UHFFFAOYSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 11 | H = 12 | O = 2 |
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| C=11 | H=12 | O=2 |
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'''2,2-Di-2-furylpropane''' is a condensation product of ] and ]. It is a relatively high boiling liquid (boiling point: 85−90 °C at 13 torr<ref>{{cite journal |title=The Condensation of Methyl Ketones with Furan| author = R. G. Ackman | journal = J. Org. Chem. | volume = 20 | pages = 1147–1158 | year = 1955 | doi = 10.1021/jo01126a001 | last2 = Brown | first2 = William H. | last3 = Wright | first3 = George F | issue = 9}}</ref>) and is a precursor (via hydrogenation) to the rubber additive bis(tetrahydrofuryl)propane used in the manufacture of high ] content rubber for high performance tires. |
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== Synthesis == |
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Furan and ] react under the action of acidic ] yielding difuryl condensation products, higher ], as well as cyclic furan tetramers (tetraoxaquterenes<ref name = tanaka>{{cite journal | author1 = Sanae Tanaka | author2 = Hidehiko Tomokuni | title = Synthesis of tetraoxaquaterene derivatives | journal = J. Heterocycl. Chem. | volume = 28 | issue = 4 | pages = 991–994 | year = 1991 | doi = 10.1002/jhet.5570280426}}</ref>). If the number of furan moieties in the oligomer is denoted as n, the number of isopropylidene moieties (derived from acetone) is n-1. In the case of aldehydes only linear oligomers are formed.<ref name = tanaka/> The simplest ] of furan and acetone is 2,2-di-2-furylpropane, the title compound. |
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This molecule is typically synthesized employing two equivalents of furan and one equivalent of acetone employing concentrated ] as the catalyst at ambient temperature and pressure. Alternatively, the reaction may be cooled during the addition of reagents and in the early phases.<ref>Rudolf Faust, et al., "Silyl-functional living cationic polymers", US Patent 6,051,657 (2000)</ref> |
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Inasmuch as the two furan moieties in 2,2-di-2-furylpropane may further react, at their respective unsubstituted 5-positions, with additional acetone the formation of oligomers can not be completely suppressed. However, the amount of ] is effected by reaction conditions, including the furan to acetone ratio and the amount of hydrochloric acid catalyst employed. |
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==Purification== |
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2,2-Di-2-furylpropane may be obtained from crude aqueous acidic reaction mixtures (typically biphasic) by allowing phase separation followed by neutralization of the organic layer. Essentially pure product is obtained by ] of the neutralized organic phase. |
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== References == |
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{{Reflist}} |
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{{DEFAULTSORT:Di-2-furylpropane, 2,2-}} |
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] |