Propane-1,3-sultone

Structural formula
General
Surname	Propane-1,3-sultone
other names	1,2-oxathiolane-2,2-dioxide ( IUPAC ) ; 1,3-propane sultone; Propio-1,3-sultone; 3-hydroxypropane-1-sulfonic acid-γ-sultone; Propane-1-sulfonic acid-3-hydroxysultone;
Molecular formula	C 3 H 6 O 3 S
Brief description	colorless, crystalline mass
External identifiers / databases
EC number	214-317-9
ECHA InfoCard	100.013.017
PubChem	14264
ChemSpider	13626
Wikidata	Q1933902
properties
Molar mass	122.14 g mol −1
Physical state	firmly
density	1.392 g cm −3 (40 ° C); 1.39 g cm −3 (40 ° C);
Melting point	31 ° C
boiling point	96 ° C (1.3 hPa)
Vapor pressure	0.48 Pa (20 ° C)
solubility	very low in water (0.025 mol% at 25 ° C, slow hydrolysis ); easily soluble in alcohols, ketones and aromatic hydrocarbons; sparingly soluble in aliphatic solvents;
safety instructions
H and P phrases	H: 301-311-332-315-318-341-350
	P: 201-260-280-303 + 361 + 353-305 + 351 + 338 + 310-308 + 313
Authorization procedure under REACH	particularly worrying : carcinogenic ( CMR )
Toxicological data	100 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Propane-1,3-sultone is a chemical compound from the substance group of sultones . It can be seen as an inner, cyclic ester of γ-hydroxypropanesulfonic acid .

Presentation and extraction

The compound is synthesized in two steps. In the first step, a radical addition of sodium hydrogen sulfite to allyl alcohol in the presence of atmospheric oxygen or peroxides as initiators produces sodium 3-hydroxypropanesulfonate. The target compound is obtained in the second step by acidic dehydration of the intermediate compound. Another synthesis starts with a Reed reaction with n- propyl chloride , chlorine and sulfur dioxide . The resulting γ-chloropropanesulfonic acid chloride is hydrolyzed to the free acid and then cyclized with the release of hydrogen chloride .

properties

Propane-1,3-sulton is a colorless, crystalline mass that melts at 31 ° C. The compound can only be vaporized under reduced pressure. The substance decomposes in the heat.

Boiling temperatures under reduced pressure
pressure	in mbar	1.33	6.67	13.32	40
Boiling temperature	in ° C	100	134	150	180

The compound is only slightly soluble in water. At 25 ° C 0.025 mol% and at 70 ° C 0.062 mol% dissolve in water. Conversely, at 25 ° C., 0.75 mol% and at 70 ° C. 0.475 mol% of water dissolve in propane-1,3-sultone. A slow hydrolysis takes place in water, which accelerates with increasing temperature. The product of the reaction with water is 3-hydroxypropanesulfonic acid.

If there is an excess of water, the hydrolysis reaction can be seen as a first-order reaction , the half -lives of which have been determined in relation to the propane-1,3-sultone concentration.

Hydrolysis rate
temperature	in ° C	20th	30th	40	70
Half-life	in h	14.8	4.8	1.6	0.11

The reaction of the compound with alcohols or alcoholates gives the corresponding 3-alkoxypropanesulfonic acids. Propane-1,3-sultone acts as an alkylating agent against many substances. The O- or S-alkylated products are formed with urea or thiourea . 3-sulfopropyl esters result with carboxylic acids . In the presence of aluminum chloride , the Friedel-Crafts alkylation of aromatics is successful .

use

The compound can be used for the production of polyether sulfones and special, zwitterionic polymers. It is also a component of battery electrolytes and photographic materials. In organic chemistry, it is used as the starting compound for the synthesis of sultaines , sulfobetaines , heterocycles and other sulfonyl-functionalized compounds.

Health hazards

Propane-1,3-sultone is classified as a particularly dangerous carcinogenic substance according to REACH and may only be manufactured or used in closed plants.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on propane-1,3-sultone. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
↑ ^a ^b ^c ^d ^e ^f Entry on 1,3-propane sultone in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Fischer, RF: Propanesultone . In: Ind. Eng. Chem. 56 (1964) 41-45, doi : 10.1021 / ie50651a008 .
↑ Entry on 1,3-propanesultone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Data sheet 1,3-propane sultone from Sigma-Aldrich , accessed on January 25, 2020 ( PDF ).
↑ ^a ^b Entry in the SVHC list of the European Chemicals Agency , accessed on August 19, 2016.
↑ ^a ^b Bordwell, FG; Osborne, E .; Chapman, D .: The Hydrolysis of Sultones. The Effect of Methyl Groups on the Rates of Ring-opening Solvolyses in J. Am. Chem. Soc. 81 (1959) 2698-2705, doi : 10.1021 / ja01520a029 .

[Römpp-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on propane-1,3-sultone. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f Entry on 1,3-propane sultone in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[Fischer-3] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m Fischer, RF: Propanesultone . In: Ind. Eng. Chem. 56 (1964) 41-45, doi : 10.1021 / ie50651a008 .

[CLP_100.013.017-4] Entry on 1,3-propanesultone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[sigma-5] Data sheet 1,3-propane sultone from Sigma-Aldrich , accessed on January 25, 2020 ( PDF ).

[SVHC-6] Entry in the SVHC list of the European Chemicals Agency , accessed on August 19, 2016.

[Bordwell-7] Bordwell, FG; Osborne, E .; Chapman, D .: The Hydrolysis of Sultones. The Effect of Methyl Groups on the Rates of Ring-opening Solvolyses in J. Am. Chem. Soc. 81 (1959) 2698-2705, doi : 10.1021 / ja01520a029 .