1120-71-4 Usage
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. It is readily soluble in water and many organic solvents such as ketones, esters and aromatic hydrocarbons.
Uses
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.
Application
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.
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.
Definition
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.
General Description
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.
Air & Water Reactions
Soluble in water [Hawley].
Reactivity Profile
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.
Hazard
Possible carcinogen.
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
Safety Profile
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.
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.
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.
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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 1120-71-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,2 and 0 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1120-71:
(6*1)+(5*1)+(4*2)+(3*0)+(2*7)+(1*1)=34
34 % 10 = 4
So 1120-71-4 is a valid CAS Registry Number.
InChI:InChI=1/C3H6O3S/c4-7(5)3-1-2-6-7/h1-3H2
1120-71-4Relevant articles and documents
N-Nitroso Sultams: On the Direction of Approach of Nucleophiles to the Sulfonyl Group
White, Emil H.,Lim, Hyung M.
, p. 2162 - 2166 (1987)
The N-nitroso derivatives of propanesultam, butanesultam, and pentanesultam were synthesized along with N-nitropropanesultam and N-nitro-N-methylmethanesulfonamide.The decompositions of the N-nitroso sultams, wich increase in rate with increasing ring size, yield the corresponding sultones and also varying amounts of regenerated sultams.These reactions are discussed in terms of higher energy pathway involving approach of the nucleophile in a direction between of sulfonyl oxygens (on the O, O, N face) and a lower energy pathway involving the conformer which permits approach of the nucleophile trans to and colinear with one of the coordinate covalent oxygen atoms (on R, O, N face). The mechanisms of the decomposition of the N-nitro sulfonamides and the tosyloxy diimide N-oxides are also discussed.N-nitrosopropanesultam (and the butyl analoque) are potent inhibitors of proteinase α-chymotrypsin.
Oxidative Cleavage and Cyclization of Disulfide Carboxylic Acids and Alcohols by Aqueous Iodine: A Facile Route to Five-Membered Ring Sultines
Doi, Joyce Takahashi,Luehr, Gary W.,Musker, W. Kenneth
, p. 5716 - 5719 (1985)
The kinetics and mechanism of the oxidative cleavage by aqueous iodine of disulfide carboxylic acids and alcohols are presented.There is evidence for intramolecular interaction of the oxygen nucleophiles.The sole product of the iodine oxidation of 3,3'-dithiodipropanol is the sultine 1,2-oxathiolane 2-oxide, which is formed after the rate-determining step, apparently via rapid cyclization of the sulfenyl iodide.The anchimeric assistance provided by the neighboring carboxylate group in the reaction of 3,3'-dithiodipropanoic acid is responsible for the pH profile of the rate of oxidative cleavage.At a given pH, the rate law for the reaction is -d/dt = kI3->(0.0905->-1 + 0.0019->-2).The inverse second term in iodide ion not has been observed previously in kinetic studies of disulfide reactions and is interpreted as evidence for a disulfide-iodonium complex.
Solvent-free method for preparing 1,3-propane sultone
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Paragraph 0010; 0023-0028, (2019/12/02)
The invention discloses a solvent-free method for preparing 11,3-propane sultone. According to the method, propenol and ammonium sulfite are used as reaction raw materials; and deionized water is adopted as medium. The preparation method comprises the following steps: stirring ammonium sulfate and deionized water; at 20-50 DEG C, preparing a mixed solution from acrolein, an initiator and deionizedwater, dropwise adding the mixed solution into a beaker, and carrying out catalytic reaction to generate an aqueous solution of 3-hydroxypropylammonium sulfonate; adding calcium hydroxide to carry out alkalization reaction, after alkalization is completed, adding concentrated sulfuric acid for acidification treatment to obtain 3-hydroxypropanesulfonic acid and solid calcium sulfate, and performing filtration to obtain an aqueous solution of the 3-hydroxypropanesulfonic acid; carrying out concentration and reduced pressure rectification to obtain a target product; adding a certain amount of calcium hydroxide and water into kettle residues, performing hydrolysis to obtain an aqueous solution of calcium 3-hydroxypropanesulfonate, adding concentrated sulfuric acid for acidification treatment,performing filtration to obtain an aqueous solution of 3-hydroxypropanesulfonic acid, and carrying out concentration and reduced pressure rectification to obtain the target product. The method has the advantages of simple process, simple raw materials, no solvent and no waste, and the yield can reach 95%.
Method for preparing 1,3-propane sultone
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Paragraph 0026; 0031; 0034; 0042, (2018/07/30)
The invention discloses a method for preparing 1,3-propane sultone. The method comprises the following steps: 1) mixing 1,3-dihalopropane and a sulfonating agent and a solvent, and performing a sulfonation reaction under certain temperature to obtain 1-halogenated-3-sodium 1-propanesulfonate; 2) adding the 1-halogenated-3-sodium 1-propanesulfonate in water, adding strong acid for adjusting a pH value to 1-3, performing acidifying treatment, performing concentration, filtering the material to remove inorganic salt, and performing concentration to a dry state to obtain 1-halogenated-3-moropholino ethanesulfonic acid; and 3) heating the 1-halogenated-3-moropholino ethanesulfonic acid under vacuum condition, and performing a lactonization reaction to obtain the 1,3-propane sultone. The methodhas the advantages that 1) the toxicity of an used raw material 1,3-dihalopropane is smaller, the 1,3-dihalopropane is safer, is easily available, and is recoverable and repeatedly used, and is convenient for storage, so that raw material and operation cost of the raw material can be greatly reduced; and 2) three-waste output in the method is less, environment pollution is reduced, environment pollution is reduced, the purity of the produced product is high and can reach more than 99%, and the water content of the product is lower than 0.1%.
