General Description
White crystalline solid or a colorless liquid. Melting point 86°F. Releases a foul odor when melting.
Reactivity Profile
PROPANE SULTONE(1120-71-4) 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.
Air & Water Reactions
Soluble in water [Hawley].
Hazard
Possible carcinogen.
Potential Exposure
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.
First aid
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respira-
tion with the aid of a pocket mask equipped with a one-way
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with run-
ning water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
warm and quiet. Effects of exposure (inhalation, ingestion
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. Medical obser-
vation is recommended for 24?48 hours after breathing
overexposure, as pulmonary edema may be delayed.
As first aid for pulmonary edema, a doctor or authorized
paramedic may consider administering a drug or other
inhalation therapy.
Shipping
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.
Incompatibilities
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.
Description
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.
Chemical Properties
1,3-Propane sultone is a white crystalline solid
or a colorless liquid above 30 ? C. It releases a foul odor as
it melts.
Chemical Properties
White To Off-White low melting Solid
Waste Disposal
C 9 H 9 Cl 2 NO; Cl 2 C 6 H 3 NHCOC 2 H5
Application
1,3-Propanesultone(1120-71-4) 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.
Definition
1,3-Propane sultone(1120-71-4) is used as a chemical intermediate. No information is available on the acute (short- term), chronic (long-term), reproductive, developmental, and carcinogenic effects of 1,3-propane sultone in humans. In rodents exposed to 1,3-propane sultone via gavage (experimentally placing the chemical in the stomach) and intravenous injection, tumors of the brain and other central nervous system (CNS) tissues have been observed. Leukemia, and tumors of the ear duct, small intestine, kidneys, lung, mammary gland, uterus, and skin have been reported in rodents exposed via gavage, injection, or dermal contact. The International Agency for Research on Cancer (IARC) has classified 1,3-propane sultone as a Group 2B, possible human carcinogen.
Preparation
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.?
Health Hazard
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
Nonflammable
Synthesis
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%.
Carcinogenicity
1,3-Propane sultone is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
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.
Toxicity evaluation
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.
Toxics Screening Level
The initial threshold screening level (ITSL) for 1,3-propane sultone (CAS # 1120-71-4) is
2 μg/m3 annual averaging time.
References
[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
