57-57-8 Usage
Description
Beta-propiolactone is a colorless liquid with a strong, slightly
sweet odor. It may occur naturally, but no clear documentation
of its occurrence in nature was found, and it must be synthesized
for commercial purposes. Beta-propiolactone is unstable
at room temperature but stable when stored at 5 C in glass
containers.
Its tendency to be unstable and react with other molecules in
the vicinity is responsible for both its toxicity and its usefulness.
Significant commercial production of beta-propiolactone took
place during the late 1950s through the mid-1970s, when it was
widely used in chemical synthesis in reactions with other
molecules to produce new chemicals. All lactones are characterized
by a ring structure consisting of two or more carbon
atoms – as can be seen from its structure, beta-propiolactone
has three in its ring – and a single oxygen, coupled with an
adjacent ketone. The fewer the carbons in the ring, the more
‘strained’ is the ring structure and the more unstable and reactive
its characteristics. When the ring bonds break, the betapropiolactone
molecules attach to other nearby molecules.
Chemical Properties
Different sources of media describe the Chemical Properties of 57-57-8 differently. You can refer to the following data:
1. β-Propiolactone is a colorless liquid which
slowly hydrolyzes to hydracrylic acid and must be cooled
to remain stable.
2. Colorless to light yellow liqui
Uses
Different sources of media describe the Uses of 57-57-8 differently. You can refer to the following data:
1. Reacts with bacteriphage DNA causing inactivation, repair and recombination
2. antiandrogen
3. Versatile intermediate in organic synthesis.
Brand name
Betaprone (Forest).
General Description
A colorless liquid with a slightly sweetish, pungent odor. Used as an intermediate in organic synthesis; disinfectant, sterilant for blood plasma, tissue grafts, vaccines, enzymes and surgical instruments.
Air & Water Reactions
Slow reaction with water to form beta- hydroxypropionic acid.
Reactivity Profile
2-Oxetanone is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. 2-Oxetanone may be incompatible with alkalis.
Hazard
Strong skin and upper respiratory tract irri-
tant, skin cancer. Possible carcinogen. Worker expo-
sure should be minimized.
Health Hazard
The toxicity potential of 2-Oxetanone via inhalation or ingestion is high; may cause death or permanent injury after very short exposures to small quantities. It is a carcinogen.
Fire Hazard
Containers may explode. When heated to decomposition, 2-Oxetanone emits acrid smoke and fumes. Stable when stored at 41F. Avoid storing in areas of exposure to the direct rays of the sun and in areas of high fire hazard. Tends to polymerize on storage. Avoid elevated temperatures.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplastigenic, and tumorigenic data. Poison
by inhalation. Moderately toxic by
intraperitoneal route. An initiator. Human mutation data reported. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Potential Exposure
β-Propiolactone is used as a chemical
intermediate in synthesis of acrylic acid and esters, acrylate
plastics; as a vapor sterilizing agent; phase disinfectant;
and a viricidal agent.
Carcinogenicity
β-Propiolactone is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental fate
Chemical/Physical. Slowly hydrolyzes to hydracrylic acid (Windholz et al., 1983). In a reactor
heated to 250 °C and a pressure of 12 mmHg, β-propiolactone decomposed to give equal amounts
of ethylene and carbon dioxide (James and Wellington, 1969).
Shipping
UN3382 Toxic by inhalation liquid, n.o.s. with
an LC 50 ≤1000 mL/m 3 and saturated vapor concentration
≥10 LC 50 , Hazard class: 6.1; Labels: 6.1 Technical
Name Required, Inhalation Hazard Zone B. UN2810 Toxic
liquids, organic, n.o.s., Hazard Class: 6.1; Labels:
6.1-Poisonous materials, Technical Name Required.
Purification Methods
Fractionally distil the lactone from sodium under reduced pressure. It gives an acidic solution in H2O. It irritates the skin and is a possib
Toxicity evaluation
It is soluble in water (370 g l1 at 25°C) and miscible in other
common organic solvents including acetone, chloroform,
diethyl ether, and ethanol (Log Kow 0.462). Hydrolysis occurs
in water where the half-life in aqueous media at 25°C is
approximately 3.5 h. If released to soil, relatively rapid
hydrolysis can be expected to occur in the presence of moisture.
Significant evaporation may occur from dry surfaces. With
a vapor pressure of 3.4 mm Hg at 25°C, it can also vaporize
into the air as temperature rises. If released to the atmosphere,
beta-propiolactone is expected to exist in the gas phase, where
it may be relatively more persistent in the absence of moisture
than it is in aqueous media. The half-life for the reaction with
photochemically produced hydroxyl radicals was estimated to
be a relatively slow rate of 45 days in the atmosphere.
Incompatibilities
Reacts with water, causing decomposi-
tion and forming 3-hydroxypropionic acid (CAS: 503-66-
3), an irritant. 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. Incompatible with acet-
ates, halogens, thiocyanates, thiosulfates, strong oxidizers;
strong bases. Forms explosive mixture with air above 75℃.
May polymerize upon storage or due to warming. Stable if
kept under refrigeration @ 5 to 10 ℃/40 to 50 ℃.
Check Digit Verification of cas no
The CAS Registry Mumber 57-57-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 57-57:
(4*5)+(3*7)+(2*5)+(1*7)=58
58 % 10 = 8
So 57-57-8 is a valid CAS Registry Number.
InChI:InChI=1/C3H4O2/c4-3-1-2-5-3/h1-2H2
57-57-8Relevant articles and documents
-
Stille,Divakaruni
, p. 1303 (1978)
-
Acrylonitrile Derivatives from Epoxide and Carbon Monoxide Reagents
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Paragraph 0194; 0196, (2019/01/15)
The present invention is directed to reactor systems and processes for producing acrylonitrile and acrylonitrile derivatives. In preferred embodiments of the present invention, the processes comprise the following steps: introducing an epoxide reagent and carbon monoxide reagent to at least one reaction vessel through at least one feed stream inlet; contacting the epoxide reagent and carbon monoxide reagent with a carbonylation catalyst to produce a beta-lactone intermediate; polymerizing the beta-lactone intermediate with an initiator in the presence of a metal cation to produce a polylactone product; heating the polylactone product under thermolysis conditions to produce an organic acid product; optionally esterifying the organic acid product to produce one or more ester products; and reacting the organic acid product and/or ester product with an ammonia reagent under ammoxidation conditions to produce an acrylonitrile product.
PROCESSES FOR PRODUCING BETA-LACTONE AND BETA-LACTONE DERIVATIVES WITH HETEROGENOUS CATALYSTS
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Paragraph 0185-0192, (2019/02/24)
The present invention is directed to processes from producing beta-lactone and beta-lactone derivatives using heterogenous catalysts. In preferred embodiments of the present invention, the processes comprise the steps: passing a feed stream comprising an epoxide reagent and a carbon monoxide reagent to a reaction zone; contacting the epoxide reagent and the carbon monoxide reagent with a heterogenous catalyst to produce a beta-lactone product in the reaction zone; and removing the beta-lactone product from the reaction zone. In preferred embodiments, the heterogenous catalyst comprises a solid support containing a cationic Lewis acid functional group and a metal carbonyl compound comprising at least one of anionic metal carbonyl compound or a neutral metal carbonyl compound. In certain preferred embodiments, the epoxide reagent and carbon monoxide reagent have a biobased content.
PROCESS FOR THE PRODUCTION OF ACID ANHYDRIDES FROM EPOXIDES
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Page/Page column 50-51, (2013/08/28)
A method of making acid anhydrides from epoxide and carbon monoxide feedstocks is presented. In various aspects, the method includes steps of reacting the contents of a feed stream comprising an epoxide, a solvent, a carbonylation catalyst and carbon monoxide to produce a first carbonylation product stream comprising a beta-lactone, then reacting the contents of the first carbonylation product stream with additional carbon monoxide to produce a second carbonylation product stream comprising an acid anhydride, and separating at least a portion of the acid anhydride from the second carbonylation product stream to produce: i) an acid anhydride product stream comprising the separated portion of acid anhydride; and ii) a recycling stream comprising the carbonylation catalyst, and finally adding the recycling stream to the feed stream.