1120-71-4

Basic information

• Product Name: 1,3-Propanesultone
• Synonyms: 3-HYDROXY-1-PROPANESULFONIC ACID GAMMA-SULTONE;3-HYDROXY-1-PROPANESULFONIC ACID SULTONE;3-HYDROXY-1-PROPANE SULFONIC SULTONE;3-HYDROXYPROPANESULFONIC ACID GAMMA-SULTONE;3-HYDROXYPROPANESULFONIC ACID SULTONE;1,2-OXATHIOLANE, 2,2-DIOXIDE;1,3-PROPANESULTONE;PROPANE SULTONE
• CAS NO: 1120-71-4
• Molecular Formula: C₃H₆O₃S
• Molecular Weight: 122.14
• EINECS: 214-317-9
• Product Categories: Industrial/Fine Chemicals;Boron, Nitrile, Thio,& TM-Cpds;Heterocycles;Heterocyclic Compounds;Sulfur & Selenium Compounds;Pharmaceutical intermediates;Halogenated Heterocycles ,Quinuclidines
• Mol File: 1120-71-4.mol

Chemical Properties

• Melting Point: 30-33 °C(lit.)
• Boiling Point: 180 °C30 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear crystals
• Density: 1.392 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00237mmHg at 25°C
• Refractive Index: 1.4332 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Slightly soluble
• Sensitive: Moisture Sensitive
• Stability: Stable, but moisture sensitive. Incompatible with strong oxidizing agents, strong acids, strong bases.
• BRN: 109782
• CAS DataBase Reference: 1,3-Propanesultone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Propanesultone(1120-71-4)
• EPA Substance Registry System: 1,3-Propanesultone(1120-71-4)

Safety Data

• Hazard Codes: T
• Statements: 45-21/22
• Safety Statements: 53-45-99
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: RP5425000
• F: 21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1120-71-4(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C3H6O3S/c4-7(5)3-1-2-6-7/h1-3H2

Synthetic route

3-hydroxypropanesulfonic acid (15909-83-8) → 1,3-propanesultone (1120-71-4)

Conditions	Yield
Stage #1: 3-hydroxypropanesulfonic acid With pyridinium p-toluenesulfonate at 55℃; for 2.5h; Large scale; Stage #2: With calcium oxide for 2h; Temperature; Reflux; Large scale;	99.4%
With VT-6 titanium alloy at 145 - 160℃; under 1 - 3.0002 Torr;	94.8%
With 2-Butoxyethanol

allyl alcohol (107-18-6) → 1,3-propanesultone (1120-71-4)

Conditions	Yield
With tert.-butylhydroperoxide; sodium hydrogensulfite; triethylamine In water at 70℃; for 6h; Reagent/catalyst; Temperature;	89%

1,3-propanesultine (24308-28-9) → 1,3-propanesultone (1120-71-4) + 3-chloro-n-propanesulfonyl chloride (1633-82-5)

Conditions	Yield
With chlorine In water	A 77% B 13%

1,3-propanesultine (24308-28-9) → 1,3-propanesultone (1120-71-4)

Conditions	Yield
With ruthenium trichloride; sodium hypochlorite In dichloromethane; water at 15℃; for 1h; Temperature; Solvent;	70%
With 3-chloro-benzenecarboperoxoic acid In chloroform-d1

3-sulfanylpropanol (19721-22-3) → 1,3-propanesultone (1120-71-4) + 3-chloro-n-propanesulfonyl chloride (1633-82-5)

Conditions	Yield
With chlorine In water at 0℃; for 0.166667h;	A 24% B 24%

3-chloro-propane-1-sulfonic acid (56984-95-3) → 1,3-propanesultone (1120-71-4)

Conditions	Yield
Unter vermindertem Druck;
at 140 - 200℃; under 750.075 Torr;	32 g

3-hydroxy-1-propanesulfonyl chloride (84145-10-8) → 1,3-propanesultone (1120-71-4)

Conditions	Yield
With butan-1-ol In chloroform-d1 Rate constant; Ambient temperature; further reagent and solvent : Et3N, EtOD;

N-nitrosopropanesultam (108214-47-7) → 1,3-propanesultone (1120-71-4) + isothiazolidine 1,1-dioxide (5908-62-3) + 3-hydroxypropanesulfonic acid (15909-83-8)

Conditions	Yield
With sodium carbonate In chloroform Product distribution; Heating; other sultams, var. reagents;	A 5 % Spectr. B 18 % Spectr. C 70 % Spectr.

sodium 3-hydroxy-1-propanesulfinate (113309-32-3) → 1,3-propanesultone (1120-71-4) + 3-hydroxy-1-propanesulfonyl chloride (84145-10-8)

Conditions	Yield
With chlorine In dichloromethane Yield given. Yields of byproduct given;

1,2-oxathiolane (5684-29-7) → 1,3-propanesultone (1120-71-4)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid

1-bromo-3-propanesulfonic acid (73384-82-4) → 1,3-propanesultone (1120-71-4)

Conditions	Yield
at 140 - 200℃; under 750.075 Torr;	8.1 g

1,3-propanesultone (1120-71-4) + diethylamine (109-89-7) → 3-(diethylamino)propane-1-sulfonic acid (1116-85-4)

Conditions	Yield
In dichloromethane at 10℃; for 1h; Product distribution / selectivity;	100%
In dichloromethane Inert atmosphere;	53%

1,3-propanesultone (1120-71-4) + triphenylphosphine (603-35-0) → 3-(triphenylphosphonio)propane-1-sulfonate (116154-22-4)

Conditions	Yield
In toluene for 12h; Reflux;	100%
In tetrahydrofuran at 25℃;	95%
In toluene for 24h; Reflux;	43%

1,3-propanesultone (1120-71-4) + triethylamine (121-44-8) → N-(3-sulfonatopropyl)-N,N,N-triethylammonium (1887-93-0)

Conditions	Yield
In toluene at 90℃; for 12h;	100%
In 1,2-dichloro-ethane at 40℃; for 6h;	98.5%
In ethanol at 20℃; for 12h; Inert atmosphere;	96%

1,3-propanesultone (1120-71-4) + m-Hydroxyaniline (591-27-5) → 3-((3-hydroxyphenyl)amino)propane-1-sulfonic acid (52962-41-1)

Conditions	Yield
In acetonitrile at 20℃;	100%
In butan-1-ol for 0.5h; Heating;	80%
for 0.5h; Reflux;	80%

1,3-propanesultone (1120-71-4) + trimethylamine (75-50-3) → N-(3-sulfonatopropyl)-N,N,N-trimethylammonium (21865-17-8)

Conditions	Yield
In ethanol; acetone at 0 - 20℃; for 24h;	100%
In acetone at 35℃; for 2h;	86%
In benzene

1,3-propanesultone (1120-71-4) + 8-ethyl-4-(4-methyl-2-oxa-1-hexyl)-3,6-dioxa-1-dodecanol (174719-47-2) → 12-ethyl-8-(4-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecanesulfonic acid sodium salt

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1h;	100%

1,3-propanesultone (1120-71-4) + 8-ethyl-4-(5-methyl-2-oxa-1-hexyl)-3,6-dioxa-1-dodecanol (174719-42-7) → 12-ethyl-8-(5-methyl-2-oxa-1-hexyl)-4,7,10-trioxa-1-hexadecanesulfonic acid sodium salt

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1h;	100%

1,3-propanesultone (1120-71-4) + tributyl-amine (102-82-9) → tri-n-butyl(3-sulfopropyl)ammonium betaine

Conditions	Yield
In acetonitrile for 72h; Reflux;	100%
In 1,2-dichloro-ethane at 40℃; for 6h;	98%
With meta-dinitrobenzene In acetonitrile at 75℃; for 7h;	90%

1,3-propanesultone (1120-71-4) + toluene-4-sulfonic acid (104-15-4) + triphenylphosphine (603-35-0) → triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate

Conditions	Yield
Stage #1: 1,3-propanesultone; triphenylphosphine In toluene Heating; Stage #2: toluene-4-sulfonic acid at 70℃; for 24h; Further stages.;	100%
Stage #1: 1,3-propanesultone; triphenylphosphine In toluene for 16h; Reflux; Inert atmosphere; Stage #2: toluene-4-sulfonic acid at 90℃; for 12h;

1,3-propanesultone (1120-71-4) + (R)-1-(4-bromophenyl)ethylamine (24358-62-1, 27298-97-1, 45791-36-4, 64313-06-0) → (R)-(+)-3-[1-(4-bromophenyl)ethylamino]-1-propanesulfonic acid

Conditions	Yield
In acetonitrile at 75℃; for 4.5h;	100%

1,3-propanesultone (1120-71-4) + N,N-dimethylaminomethylferrocene (1271-86-9) → dimethyl-3-sulfopropyl(ferrocenylmethyl)ammonium

Conditions	Yield
In ethyl acetate for 19h;	100%
In benzene a mixt. of N,N-dimethylaminomethylferrocene and 1,3-propanesultone in anhyd. benzene at room temp. for 24 h, then reflux for 1 h; cooling, treating with ether, yellow ppt. is removed by filtration, washed with ether and dried in vac.; elem. anal.;	95%

1,3-propanesultone (1120-71-4) + N,N-dimethyl-1-(4-vinylphenyl)-methanamine (2245-52-5) → 4-vinylbenzyldimethylammonio propanesulfonate (172530-02-8)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol In acetonitrile at 50℃; for 24h;	100%
In acetonitrile at 49.84℃; for 48h; Inert atmosphere;	84%

1,3-propanesultone (1120-71-4) + N,N,N'N'-tetramethyl-1,3-propanediamine (110-95-2) → N,N,N',N'-tetramethyl-N,N'-bis(3-sulfopropyl)-1,3-propandiyldiammonium bis(hydrogensulfate)

Conditions	Yield
Stage #1: 1,3-propanesultone; N,N,N'N'-tetramethyl-1,3-propanediamine In 1,2-dichloro-ethane at 55 - 60℃; for 2.25h; Inert atmosphere; Stage #2: With sulfuric acid In water at 80℃; for 2h;	100%

1,3-propanesultone (1120-71-4) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → N,N,N',N'-tetramethyl-N,N'-bis(3-sulfopropyl)-1,6-hexandiyldiammonium bis(hydrogensulfate)

Conditions	Yield
Stage #1: 1,3-propanesultone; N,N,N',N'-tetramethylhexamethylenediamine In 1,2-dichloro-ethane at 55 - 60℃; for 2.25h; Inert atmosphere; Stage #2: With sulfuric acid In water at 80℃; for 2h;	100%

1,3-propanesultone (1120-71-4) + 4-dimethylamino-butyric acid benzyl ester (768385-35-9) → C16H25NO5S (1349808-78-1)

Conditions	Yield
With 2,6-di-tert-butyl-pyridine In N,N-dimethyl-formamide at 150℃; Inert atmosphere;	100%
With 2,6-di-tert-butyl-pyridine at 150℃; for 1h; Inert atmosphere;

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 1,3-propanesultone (1120-71-4) → N,N'-bis(3-sulfopropyl)triethylenediaminium bis(hydrogensulfate)

Conditions	Yield
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; 1,3-propanesultone In tetrahydrofuran for 24h; Reflux; Stage #2: With sulfuric acid at 170℃; for 20h;	100%

1,3-propanesultone (1120-71-4) + N,N-dimethylaminododecane (112-18-5) → 3-(N,N-dimethyldodecylammonium)propanesulfonic acid hydrogen sulphate (1187184-73-1)

Conditions	Yield
Stage #1: 1,3-propanesultone; N,N-dimethylaminododecane In water at 65 - 70℃; for 1.25h; Inert atmosphere; Stage #2: With sulfuric acid In water at 20 - 80℃; for 2h; Inert atmosphere;	100%
In ethyl acetate at 55℃; for 3h;	96%
With sulfuric acid; water

1,3-propanesultone (1120-71-4) + C24H23F3N2O4 (1567883-58-2) → C27H29F3N2O7S

Conditions	Yield
In acetonitrile at 120℃; for 120h; Schlenk technique; Inert atmosphere;	100%

1,3-propanesultone (1120-71-4) + C27H27F3N2O4 → C30H33F3N2O7S

Conditions	Yield
In acetonitrile at 120℃; for 120h; Schlenk technique; Inert atmosphere;	100%

1,3-propanesultone (1120-71-4) + 1-(2,4,6-trimethylphenyl)-4,5-dihydro-1H-imidazole (717110-52-6) → 1-(2,4,6-trimethylphenyl)-3-(3-sulfonatopropyl)imidazolidinium

Conditions	Yield
In dichloromethane for 12h; Reflux;	100%

1,3-propanesultone (1120-71-4) + tri-n-propylamine (102-69-2) → C12H27NO3S

Conditions	Yield
In acetonitrile for 24h; Reflux;	100%
In 1,2-dichloro-ethane at 30℃; for 6h;	98%

1,3-propanesultone (1120-71-4) + tributylphosphine (998-40-3) → tributylphosponiumpropane sulfonate

Conditions	Yield
In acetonitrile for 72h; Reflux; Inert atmosphere;	100%
In chloroform at 40℃; for 168h; Inert atmosphere;	91%

1,3-propanesultone (1120-71-4) + iminodiacetic acid (142-73-4) → 2,2'-((3-sulfopropyl)azanediyl)diacetic acid

Conditions	Yield
In water at 85℃; for 4h;	100%
In water at 85℃; for 4h;
With water at 85℃; for 4h;

1,3-propanesultone (1120-71-4) + Tri-n-octylamine (1116-76-3) → C28H59NO2S

Conditions	Yield
In toluene for 72h; Reflux;	100%

1,3-propanesultone (1120-71-4) + 4-Iodophenol (540-38-5) → C9H10IO4S(1-)*Na(1+) (1356380-94-3)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane at 20℃; for 4h; Inert atmosphere;	99.9%

1-methyl-1H-imidazole (616-47-7) + 1,3-propanesultone (1120-71-4) → 3-(3-methyl-1H-imidazol-3-ium-1-yl)propane-1-sulfonate

Conditions	Yield
In acetone at 20℃; for 24h;	99%
In neat (no solvent) at 50℃; for 6h;	97%
In neat (no solvent) at 50℃; for 6h;	97%

1,3-propanesultone (1120-71-4) + 2,7-bis(4-pyridyl)-9,9-dipropylfluorene (342889-57-0) → 9,9-dipropyl-2,7-bis(1-sulfopropyl-4-pyridinium)fluorene

Conditions	Yield
In benzonitrile at 140℃; for 0.25h;	99%

1,3-propanesultone (1120-71-4) + Dimethyl-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-undecyl)amine (148171-75-9) → 3-[dimethyl(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)ammonium]propanesulfonate

Conditions	Yield
In acetonitrile for 20h; Heating;	99%

1,3-propanesultone (1120-71-4) + 4,5-dihydro-1-[3-(triethoxysilyl)propyl]imidazole → 3-(1-(3-(trimethoxysilyl)propyl)-4,5-dihydro-1H-imidazol-3-ium-3-yl)propane-1-sulfonate (1210973-96-8)

Conditions	Yield
In acetonitrile at 0 - 80℃; for 8.5h;	99%
at 40℃; for 0.5h;

Upstream product

• 15909-83-8 3-hydroxypropanesulfonic acid 
• 56984-95-3 3-chloro-propane-1-sulfonic acid 
• 24308-28-9 1,3-propanesultine 
• 19721-22-3 3-sulfanylpropanol 
• 84145-10-8 3-hydroxy-1-propanesulfonyl chloride 
• 108214-47-7 N-nitrosopropanesultam 
• 113309-32-3 sodium 3-hydroxy-1-propanesulfinate 
• 5684-29-7 1,2-oxathiolane 
• 73384-82-4 3-bromopropane-1-sulfonic acid 
• 107-18-6 allyl alcohol 

Downstream Products

• 15471-17-7 1-(3-sulfopropyl)pyridine 
• 65287-04-9 Anhydro-2-methyl-5-chlor-3<3'-sulfopropyl>-benzthiazoliumhydroxid 
• 114889-81-5 3-(amino-benzylidenehydrazono-methylsulfanyl)-propane-1-sulfonic acid 
• 99982-53-3 3-p-tolylcarbamimidoylmercapto-propane-1-sulfonic acid 
• 100139-11-5 3-(4-thiazol-2-ylsulfamoyl-anilino)-propane-1-sulfonic acid 
• 7326-20-7 3-phenylsulfanyl-propane-1-sulfonic acid 
• 51652-08-5 propyl nicotinamide sulfonate 
• 52962-42-2 3-(4-hydroxy-anilino)-propane-1-sulfonic acid 
• 70867-46-8 3-benzimidoyloxy-propane-1-sulfonic acid 
• 114554-19-7 3-(4-sulfamoyl-anilino)-propane-1-sulfonic acid 
• 21668-77-9 propane-1,3-disulfonic acid 
• 21668-81-5 3-carbamimidoylmercapto-propane-1-sulfonic acid 
• 72943-20-5 3-(phenylammonio)propane-1-sulfonate 
• 116154-22-4 3-(triphenylphosphonio)propane-1-sulfonate 

Relevant articles and documents

N-Nitroso Sultams: On the Direction of Approach of Nucleophiles to the Sulfonyl Group

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.

1,2-Oxathiolan, a Simple Sultene

Evidence is presented which indicates that pyrolysis of N-(3-hydroxypropylthio)phthalimide gives 1,2-oxathiolan as a volatile product via an intermediate tentatively identified as a cyclic oligomer.

Oxidative Cleavage and Cyclization of Disulfide Carboxylic Acids and Alcohols by Aqueous Iodine: A Facile Route to Five-Membered Ring Sultines

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.

1,3-propane sultone preparation method

The invention relates to a 1,3-propane sultone preparation method, which comprises: S1, completely mixing in a reaction container by using 3-chloropropanol and sodium sulfite as raw materials and using water as a solvent, controlling the temperature at 25-120 DEG C, carrying out a reaction for 4-48 h, carrying out pressure reducing dewatering concentration, adding concentrated hydrochloric acid tothe concentrated liquid, carrying out acidification, controlling the temperature at 0-80 DEG C, stirring for 1-24 h, filtering, and concentrating the filtrate to obtain 3-hydroxypropanesulfonic acid;S2, controlling the temperature of the concentrated liquid obtained in the step S1 at 40-110 DEG C, and carrying out pressure reducing concentrating to carry out dewatering ring closure on the 3-hydroxypropanesulfonic acid in the concentrated liquid to obtain a crude product containing 1,3-propane sultone; and S3, rectifying the crude product containing 1,3-propane sultone to obtain 1,3-propane sultone. According to the present invention, the method has characteristics of short process route, less three-waste and simple post-treatment, wherein the total yield can achieve more than 90%, and the purity of the product can achieve more than 99.9%.

Solvent-free method for preparing 1,3-propane sultone

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%.

Preparation method of 1,3-propane sultone

The invention discloses a preparation method of 1,3-propane sultone. The preparation method of the 1,3-propane sultone comprises the following steps of (1) under the existence of tetraethylammonium bromide, reacting 1,3-dichloropropane and sulfur dioxide in acetonitrile under the action of a constant current so as to obtain 1,3- propane sulfincacid lactone; (2) carrying out oxidation reaction on the prepared 1,3-propane sulfincacid lactone and an oxidizing agent in an organic solvent to obtain the 1,3-propane sultone. The preparation method of the 1,3-propane sultone provided by the inventionhas the advantages of higher yield, high purity, cheap and easy-to-get raw materials, mild reaction conditions, simple preparation process and the like.

Method for preparing 1,3-propane sultone

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%.

A method for preparing 1, 3 - propane lactone (by machine translation)

The invention discloses a 1, 3 - propane lactone of the preparation method, comprises the following steps: first preparing a calcium chloride solution, then adding citric acid mixed solution prepared A, and mixed with the sodium polyacrylate solution preparing mixed solution B, then rapidly added to the sodium carbonate solution precipitation, for preparing porous calcium carbonate, and peroxy benzoic acid in the solution is impregnated to obtain the catalyst; the allyl sodium sulfonate and sulfuric acid solution, adding catalyst to react, adding ethanol solution of sodium hydroxide reaction, and finally adding hydrochloric acid, to obtain 3 - hydroxy propane sulfonic acid; the obtained 3 - hydroxy propane sulfonic acid and hexane mixed in added to the three-mouth flask, stirring the reaction, after the reaction cooled to the room temperature, vacuum distillation, to obtain the target product 1, 3 - propane lactone. The method is simple in operation, low energy consumption, high product yield. (by machine translation)

Preparation method of 1, 3-propane sultone

The invention discloses a preparation method of 1, 3-propane sultone. The preparation method comprises the following steps: (1), in the presence of an amine compound and an initiator, performing a free radical addition reaction on allyl alcohol and bisulfite in water to produce 3-hydroxypropanesulfonate, and acidifying to obtain 3-hydroxypropanesulfonic acid; (2), then performing a cyclization reaction on the 3-hydroxypropanesulfonic acid at the vacuum degree of 0-10mmHg and the temperature of 150-200 DEG C to produce the 1, 3-propane sultone. By the preparation method, the environment pollution can be reduced, so that the environment friendliness is better; in addition, the preparation method has the advantages of simple and safe operation, relatively ideal yield and the like.

Method for preparing 1,3-propane sultone

The invention discloses a method for preparing 1,3-propane sultone. The method includes the steps that (1) 1,3-propanesulfonic acid is prepared: sodium sulfite, sodium bisulfite and allyl alcohol are added into a reactor under the room temperature condition, a pH value is regulated to be 5 to 5.5, infrared radiation induction is adopted, azo diisobutyl nitrile performs catalytic reaction for 2 to 3 hours, concentrated hydrochloric acid is added, the reaction is performed at the temperature of 85 to 90 DEG C for 2 to 3 hours, generated salt is removed through filtration, and n-butyl alcohol is added into filtrate to perform extraction separation so as to obtain the 3-hydroxy-1-propanesulfonic acid; (2) the 1,3-propane sultone is prepared: pyridinium p-toluenesulfonate and zeolites are added, dehydration reaction is performed at the temperature of 50-60 DEG C for 2-3 hours, distillation is performed to obtain 147-149 DEG C of fraction, and calcium oxide is added to perform heating reflux for 1-2 hours to obtain the 1,3-propane sultone. The product prepared by means of the method is high in yield and purity. In addition, the moisture content of the product is mostly above 0.1%, the amplification effect and other problems do not exist, and the method is suitable for industrial production.