1,3-dioxan-2-one

Structural formula
General
Surname	1,3-dioxan-2-one
other names	Trimethylene carbonate
Molecular formula	C 4 H 6 O 3
Brief description	colorless solid
External identifiers / databases
CAS number 2453-03-4 EC number 607-395-4 ECHA InfoCard 100.114.239 PubChem 123834 ChemSpider 110377 Wikidata Q161506
properties
Molar mass	102.09 g mol −1
Physical state	firmly
density	1.23 g cm −3 (50 ° C)
Melting point	47 ° C
boiling point	83-85 ° C (13 Pa)
Refractive index	1.4409
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302-319 P: 305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

1,3-Dioxan-2-one is a chemical compound from the group of saturated oxygen-containing heterocycles . It consists of a six-membered ring, the 1- and 3-positions of which are formed by oxygen atoms. There is a keto group in the 2-position . The compound can also be viewed as a cyclic carbonate .

presentation

1,3-Dioxan-2-one is prepared via the cyclization of organic carbonates such as di-tert-butyl dicarbonate in the presence of the base DMAP or diethyl carbonate in the presence of sodium methoxide at an elevated temperature with 1,3-propanediol .

It can also be obtained in very good yield from oxetane under high carbon dioxide pressure over an antimony catalyst.

properties

1,3-Dioxan-2-one is a colorless solid at room temperature that melts at 47 ° C.

use

1,3-Dioxan-2-one is a starting material for the production of polytrimethylene carbonate . This can be obtained by ring opening by means of a Lewis acid . Only catalytic amounts of the Lewis acid are required. For example, complexes of scandium can be used for this purpose. Also copolymers with ethylene glycol can in this way with zinc are obtained catalysts.

Thietane can be produced by the reaction between 1,3-dioxan-2-one and potassium thiocyanate at 140 ° C. Potassium cyanate and carbon dioxide are produced as by-products .

${\displaystyle \mathrm {C_{4}H_{6}O_{3}+\ KSCN\longrightarrow \ C_{3}H_{6}S+\ KOCN+\ CO_{2}} }$

Individual evidence

1. ↑ ^{a b c} K. Sommer: On the representation of cyclic arsenites and thioarsenites , in: Z. anorg. allg. Chem. , 1969 , 370 , pp. 227-234.
2. ^ ^{A b} J. W. Hill, WH Carothers: Studies of Polymerization and Ring Formation. XX. Many-Membered Cyclic Esters , in: J. Am. Chem. Soc. , 1933 , 55 , pp. 5031-5039.
3. ↑ ^{a b} data sheet 1,3-DIOXAN-2-ONE from Sigma-Aldrich , accessed on May 5, 2011 ( PDF ).
4. ^ Y. Basel, A. Hassner: Di-tert-butyl Dicarbonate and 4- (Dimethylamino) pyridine Revisited. Their Reactions with Amines and Alcohols , in: J. Org. Chem. , 2000 , 65 , pp. 6368-6380.
5. ↑ A. Klys, W. Czardybon, J. Warkentin, NH Werstiuk: Synthesis and thermolysis of a spiro-fused oxadiazoline - Evidence for sequential formation of carbene and oxirane intermediates, and for oxirane dimerization. In: Canadian Journal of Chemistry . 82 (12), 2004, pp. 1769-1773, doi : 10.1139 / v04-158 .
6. ↑ A. Baba, H. Kashiwagi, H. Matsuda: Cycloaddition of oxetane and carbon dioxide catalyzed by tetraphenylstibonium iodide , in: Tetrahedron Lett. , 1985 , 26 , pp. 1323-1324.
7. ↑ J. Ling, W. Zhu, Z. Shen: Controlling Ring-Opening Copolymerization of -Caprolactone with Trimethylene Carbonate by Scandium Tris (2,6-di-tert-butyl-4-methylphenolate) , in: Macromolecules , 2004 , 37 , Pp. 758-763.
8. Jump up ↑ L. Zhou, Y. Yao, Y. Zhang, M. Xue, J. Chen, Q. Shen: Synthesis and Characterization of Homoleptic Lanthanide Guanidinate Complexes and Their Catalytic Activity for the Ring-Opening Polymerization of Trimethylene Carbonate , in: Eur J. Inorg. Chem. , 2004 , 10 , pp. 2167-2172.
9. ↑ F. Meng, C. Hiemstra, GHM Engbers, J. Feijen: Biodegradable Polymersomes , in: Macromolecules , 2003 , 36 , pp. 3004-3006.
10. ↑ S. Searles, EF Lutz in: A new synthesis of small ring cyclic sulfides , in: J. Am. Chem. Soc. , 1958 , 80 , p. 3168.