Propane sultone also known as 1,3-propane sultone was first
produced in the United States in 1963. Propane sultone exists
at room temperature as a colorless liquid with a foul odor or as
a white crystalline solid.
1,3-Propane sultone is a white crystalline solid or a colorless liquid above 30°C. It releases a foul odor as it melts. It is readily soluble in water and many organic solvents such as ketones, esters and aromatic hydrocarbons.
1,3-Propane sultone is used as a chemical intermediate to
introduce the sulfopropyl group into molecules and to confer
water solubility and an anionic character to the molecules. It is
used as a chemical intermediate in the production of fungicides,
insecticides, cation-exchange resins, dyes, vulcanization
accelerators, detergents, lathering agents, bacteriostats, and
a variety of other chemicals and as a corrosion inhibitor for
mild (untempered) steel.
1,3-Propanesultone is a cyclic sulfonic ester mainly used to introduce a propane sulfonic functionality into the organic structure. It has been used in preparation of poly[2-ethynyl-N-(propylsulfonate)pyridinium betaine],novel poly(4-vinylpyridine) supported acidic ionic liquid catalyst,novel poly(4-vinylpyridine) supported acidic ionic liquid catalyst.
1,3-Propanesultone can be used to synthesize:
A sulfonic acid functionalized acidic ionic liquid modified silica catalyst that can be used in hydrolysis of cellulose.
Zwitterionic-type molten salts with unique ion conductive properties.
Zwitterionic organofunctional silicones by the quaternization of organic amine functional silicones.
1,3-propane sultone is produced commercially by dehydrating gamma-hydroxy-propanesulfonic acid, which is prepared from sodium hydroxypropanesulfonate. this sodium salt is prepared by addition of sodium bisulfite to allyl alcohol.
1,3-Propane sultone is a sultone. It is used as a chemical intermediate. When heated to decomposition, it emits toxic fumes of sulfur oxides. Humans are potentially exposed to residues of 1,3-propane sultone when using products manufactured from this compound. The primary routes of potential human exposure to 1,3-propane sultone are ingestion and inhalation. Contact with this chemical can cause mild irritation of the eyes and skin. It is reasonably anticipated to be a human carcinogen.
Propanesultone is a synthetic, colorless liquid or white crystalline solid that is readily soluble in water and many organic solvents such as ketones, esters and aromatic hydrocarbons. Melting point 86°F. Releases a foul odor when melting.
Soluble in water [Hawley].
1,3-Propanesultone reacts slowly with water to give 3-hydroxopropanesulfonic acid. This reaction may be accelerated by acid. May react with strong reducing agents to give toxic and flammable hydrogen sulfide.
Propane sultone is a carcinogen
in experimental animals and a suspected human
carcinogen. No human data are available.
It is a carcinogen in rats when given orally,
intravenously, or by prenatal exposure and a
local carcinogen in mice and rats when given
subcutaneously.
Flammability and Explosibility
Non flammable
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, tumorigenic, and
teratogenic data. Poison by subcutaneous
route. Moderately toxic by skin contact and
intraperitoneal routes. Human mutation data
reported. Implicated as a human brain
carcinogen. A slun irritant. When heated to
decomposition it emits toxic fumes of SOx.
Example 6 (2) Preparation of 1,3-propanesulfonolactone: 1.5 kg of pyridinium p-toluenesulfonate and 3 kg of zeolite were added to 110 kg of 3-hydroxy-1-propanesulfonic acid. The dehydration reaction was carried out at 55°C for 2.5 hours. Upon completion of the reaction, the reaction mixture was distilled and the 147-149 °C fraction was collected. To the fraction, 1 kg of calcium oxide was added and heated and refluxed for 2 hours to give a final yield of 95.5 kg of 1,3-propanesulfonic acid lactone. The total yield of this step was 99.4%, the purity of the product was ≥99.99% and the impurity content was <0.02%.
A potential danger to those involved
in use of this chemical intermediate to introduce the sulfo-
propyl group (-CH 2 CH 2 CH 2 SO 3-) into molecules of
other products.
1,3-Propane sultone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Routes and Pathways and Relevant Physicochemical
Properties
Appearance: white crystalline solid or colorless liquid.
Solubilities: readily soluble in ketones, esters, and aromatic
hydrocarbons; insoluble in aliphatic hydrocarbons; and
soluble in water (100 g l-1).
Partition Behavior in Water, Sediment, and Soil
If 1,3-propane sultone is released to soil, it will be expected to
rapidly hydrolyze if the soil is moist, based upon the rapid
hydrolysis observed in aqueous solution. Since it rapidly
hydrolyzes, adsorption to and volatilization from moist soil are
not expected to be significant processes, although no data
specifically regarding the fate of 1,3-propane sultone in soil
were located. If released into water, it will be expected to rapidly hydrolyze. The produce of hydrolysis is 3-hydroxy-
1-propansulfonic acid. Since it rapidly hydrolyzes, bioconcentration,
volatilization, and adsorption to sediment and
suspended solids are not expected to be significant processes.
If released to the atmosphere, it will be susceptible to photooxidation
via vapor-phase reaction with photochemically
produced hydroxyl radicals with a half-life of 8 days estimated
for this process.
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. UN2810 Toxic liquids, organic, n.o.s.,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials,
Technical Name Required.
The reaction of propane sultone with guanosine and DNA at
pH 6–7.5 gave an N7-alkylguanosine as the main product
(>90%). Similar evidence suggested that two of the minor
adducts were N1- and N6-alkyl derivatives, accounting for
approximately 1.6 and 0.5% of the total adducts, respectively.
N7- and N1-alkylguanine were also detected in the DNA reacted
with propane sultone.
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explo-
sions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides.
The initial threshold screening level (ITSL) for 1,3-propane sultone (CAS # 1120-71-4) is
2 μg/m3 annual averaging time.
[1] Patent: CN105348254, 2016, A. Location in patent: Paragraph 0039; 0040; 0042
[2] Russian Journal of Applied Chemistry, 1996, vol. 69, # 1, p. 86 - 88
[3] Bulletin des Societes Chimiques Belges, 1955, vol. 64, p. 747,752, 768
[4] Bulletin des Societes Chimiques Belges, 1955, vol. 64, p. 409,425, 747, 760
[5] Journal of the American Chemical Society, 1953, vol. 75, p. 748
