1,3-二氧五環

1,3-二氧五環
	IUPAC名; 1,3-Dioxolane
	系統名; 1,3-Dioxacyclopentane
別名	二氧五環; 5-冠-2; 1,3-二氧戊環; 二氧戊環
識別
CAS號	646-06-0
PubChem	12586
ChemSpider	12066
SMILES	O1CCOC1;
InChI	1/C3H6O2/c1-2-4-5-3-1/h1-3H2;
InChIKey	SNQXJPARXFUULZ-UHFFFAOYAS
EINECS	211-463-5
ChEBI	87597
性質
化學式	C3H6O2
摩爾質量	74.08 g·mol⁻¹
外觀	揮發性的無色液體
密度	1.06 g/cm3
熔點	-95 °C（178 K）（）
沸點	74 °C（347 K）（）
溶解性（水）	混溶
溶解性	可溶於乙醇、乙醚和丙酮
相關物質
相關化學品	1,2-二氧五環
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

1,3-二氧五環是一種有機化合物，化學式 C
3H
6O
2。

製備

1,3-二氧五環可以由乙二醇和甲醛在酸催化下而成：^[4]

它也可以由環氧乙烷和甲醛在四氯化錫或四乙基溴化銨催化下反應而成。^[5]

性質

物理性質

1,3-二氧五環是一種揮發性的無色液體，沸點 74 °C。^[2]在−97 °C下，1,3-二氧五環會凝固，熔化熱6.57 kJ·mol⁻¹。^[6]^[7]1,3-二氧五環有兩種同質異形體，其中II型在−131 °C以下產生，轉變成I型時會放出2.68 kJ·mol⁻¹的能量。^[7]它混溶於水、乙醚、丙酮和四氫呋喃。^[3]^[5]

化學性質

1,3-二氧五環傾向形成過氧化物。^[3]在酸存在下，1,3-二氧五環容易水解成乙二醇和甲醛，在鹼中則比較穩定。當1,3-二氧五環被加熱到470 °C 至500 °C時，它會分解成甲酸和乙烯。^[5]它和乙酰溴反應，生成2-(溴甲氧基)乙酸乙酯。^[8]

用處

1,3-二氧五環是生產聚甲醛的共聚物。^[3]

參考資料

^ Front Matter. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 145. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.
^ ^2.0 ^2.1 ^2.2 ^2.3 ^2.4 Record of CAS RN 646-06-0 in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）
^ ^3.0 ^3.1 ^3.2 ^3.3 ^3.4 Entry on 1,3-Dioxolan. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.
^ von Karl-Heinz Lautetnschläger, Werner Schröter, Andrea Wanninger. Taschenbuch der Chemie – Karl-Heinz Lautenschläger, Werner Schröter, Andrea Wanninger. Harri Deutsch Verlag. 2005: 451. ISBN 978-3-81711760-4.
^ ^5.0 ^5.1 ^5.2 Vishnu Ji Ram; Arun Sethi; Mahendra Nath; Ramendra Pratap: The Chemistry of Heterocycles – Nomenclature and Chemistry of Three-to-Five Membered Heterocycles, Elsevier 2017, ISBN 978-0-08-101033-4.
^ E. S. Domalski, E. D. Hearing: Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III. in : J. Phys. Chem. Ref. Data 25 (1996) 1–525, doi:10.1063/1.555985.
^ ^7.0 ^7.1 Clegg, G.A.; Melia, T.P.: Thermodynamics of polymerization of heterocyclic compounds. Part V. The heat capacity, entropy, enthalpy and free energy of 1,3-dioxolan and poly-1,3-dioxolan in Polymer 10 (1969) 912–922.
^ Silvia Vertuani, Anna Baldisserotto, Katia Varani, Pier Andrea Borea, Bonache De Marcos Maria Cruz, Luca Ferraro, Stefano Manfredini, Alessandro Dalpiaz. Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives. European Journal of Medicinal Chemistry. 2012-08, 54: 202–209 [2021-08-11]. doi:10.1016/j.ejmech.2012.04.045. （原始內容存檔於2018-07-03）（英語）.

[1] Front Matter. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014: 145. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001.

[GESTIS-2] 2.0 ^2.1 ^2.2 ^2.3 ^2.4 Record of CAS RN 646-06-0 in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）

[römpp-3] 3.0 ^3.1 ^3.2 ^3.3 ^3.4 Entry on 1,3-Dioxolan. at: Römpp Online. Georg Thieme Verlag, retrieved {{{Datum}}}.

[von_Karl-Heinz_Lautenschläger,_Werner_Schröter,_Andrea_Wanninger-4] von Karl-Heinz Lautetnschläger, Werner Schröter, Andrea Wanninger. Taschenbuch der Chemie – Karl-Heinz Lautenschläger, Werner Schröter, Andrea Wanninger. Harri Deutsch Verlag. 2005: 451. ISBN 978-3-81711760-4.

[Ram-5] 5.0 ^5.1 ^5.2 Vishnu Ji Ram; Arun Sethi; Mahendra Nath; Ramendra Pratap: The Chemistry of Heterocycles – Nomenclature and Chemistry of Three-to-Five Membered Heterocycles, Elsevier 2017, ISBN 978-0-08-101033-4.

[Domalski-6] E. S. Domalski, E. D. Hearing: Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III. in : J. Phys. Chem. Ref. Data 25 (1996) 1–525, doi:10.1063/1.555985.

[Clegg-7] 7.0 ^7.1 Clegg, G.A.; Melia, T.P.: Thermodynamics of polymerization of heterocyclic compounds. Part V. The heat capacity, entropy, enthalpy and free energy of 1,3-dioxolan and poly-1,3-dioxolan in Polymer 10 (1969) 912–922.

[8] Silvia Vertuani, Anna Baldisserotto, Katia Varani, Pier Andrea Borea, Bonache De Marcos Maria Cruz, Luca Ferraro, Stefano Manfredini, Alessandro Dalpiaz. Synthesis and in vitro stability of nucleoside 5′-phosphonate derivatives. European Journal of Medicinal Chemistry. 2012-08, 54: 202–209 [2021-08-11]. doi:10.1016/j.ejmech.2012.04.045. （原始內容存檔於2018-07-03）（英語）.

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