ChemicalBook > CAS DataBase List > 2-Oxetanone

2-Oxetanone

Product Name
2-Oxetanone
CAS No.
57-57-8
Chemical Name
2-Oxetanone
Synonyms
Oxetan-2-one;β-Propiolactone;β-Propiolactone;BETA-PROPIOLACTONE;Oxetanone;Betaprone;B-PROPIOLACTONE;1,3-Propiolactone;NSC-21626;Propanlide
CBNumber
CB0275433
Molecular Formula
C3H4O2
Formula Weight
72.06
MOL File
57-57-8.mol
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2-Oxetanone Property

Melting point:
-33 °C (lit.)
Boiling point:
162 °C (lit.)
Density 
1.146 g/mL at 25 °C (lit.)
vapor pressure 
3 at 25 °C (NIOSH, 1997)
refractive index 
n20/D 1.412(lit.)
Flash point:
158 °F
storage temp. 
-20°C
solubility 
Miscible with acetone, alcohol, chloroform, and ether (Windholz et al., 1983)
form 
Liquid
color 
Colorless liquid with a sweet but irritating odor
Odor
pungent odor
Water Solubility 
37 g/100 mL
Sensitive 
Moisture Sensitive
Merck 
14,7820
Henry's Law Constant
7.6 at 25 °C (approximate - calculated from water solubility and vapor pressure)
Stability:
Moisture Sensitive, Very Hygroscopic
InChIKey
VEZXCJBBBCKRPI-UHFFFAOYSA-N
CAS DataBase Reference
57-57-8(CAS DataBase Reference)
IARC
2B (Vol. 4, Sup 7, 71) 1999
NIST Chemistry Reference
«beta»-Propiolactone(57-57-8)
EPA Substance Registry System
beta-Propiolactone (57-57-8)
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Safety

Hazard Codes 
T+
Risk Statements 
45-26-36/38
Safety Statements 
53-45-99
RIDADR 
UN 3382 6.1/PG 1
WGK Germany 
3
RTECS 
RQ7350000
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
I
HS Code 
29322090
Hazardous Substances Data
57-57-8(Hazardous Substances Data)
Toxicity
LC50 (inhalation) for rats 25 ppm/6-h (quoted, RTECS, 1985).
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H330Fatal if inhaled

H350May cause cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P5648
Product name
β-Propiolactone
Purity
Grade II, ≥90%
Packaging
1ml
Price
$106
Updated
2024/03/01
Sigma-Aldrich
Product number
P5648
Product name
β-Propiolactone
Purity
Grade II, ≥90%
Packaging
25mL
Price
$582
Updated
2024/03/01
Alfa Aesar
Product number
B23197
Product name
beta-Propiolactone, 97%
Packaging
1g
Price
$77.1
Updated
2024/03/01
Alfa Aesar
Product number
B23197
Product name
beta-Propiolactone, 97%
Packaging
5g
Price
$187
Updated
2024/03/01
Alfa Aesar
Product number
B23197
Product name
beta-Propiolactone, 97%
Packaging
25g
Price
$522
Updated
2024/03/01
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2-Oxetanone Chemical Properties,Usage,Production

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 ℃ 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

β-Propiolactone is a colorless liquid which slowly hydrolyzes to hydracrylic acid and must be cooled to remain stable. It reacts with alcohols, acid chlorides, ammonia, and water to yield β-substituted propionic acid derivatives. The most important characteristic of the substance is its ability to polymerize. This highly exothermic process occurs simply by warming, although it is also catalyzed by both acid and base.

Physical properties

β-Propiolactone is a colorless, highly reactive liquid,thatis solublein water, alcohol, acetone, and chloroform (solubilityinwaterat 25℃, 37 vol %).

Uses

As late as 1974, b-propiolactone was used in the United States in the preparation of acrylic acid and acrylate esters. Today, its principal significance is as a reactive intermediate in organic syntheses; a small amount is treated with ammonia to provide balanine. b-Propiolactone was also used as a disinfectant. It appeared to be an attractive replacement for formaldehyde due to its 25-fold greater disinfecting power, but it has since been abandoned because of its carcinogenic properties.

Uses

Reacts with bacteriphage DNA causing inactivation, repair and recombination

Uses

Versatile intermediate in organic synthesis.

Preparation

β-Propiolactone is synthesized by passing equimolar amounts of ketene and formaldehyde into either acetone or b-propiolactone itself. The reaction is carried out at low temperature (<20℃) with a yield of ca. 90 %. Both aluminum chloride and zinc chloride have been employed as catalysts, and the use of methyl borate has also been suggested.

Definition

ChEBI: Beta-propiolactone is a propan-3-olide. It is functionally related to a 3-hydroxypropionic acid. It derives from a hydride of an oxetane.

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 ℃.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinera- tor equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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2-Oxetanone Suppliers

Shanghai Jizhi Biochemical Technology Co. Ltd.
Tel
400-400-400-9004166 18117592386
Email
3007522982@qq.com
Country
China
ProdList
52712
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Lanzhou Zhongchuan Xuentian Tech.Co. LTD
Tel
186 6172 2072 18661722072
Email
sales@xuentian.cn
Country
China
ProdList
176
Advantage
58
Cato Research Chemicals Inc.
Tel
18813968010
Email
Xiang.Liang@cato-chem.com
Country
China
ProdList
904
Advantage
58
Guangzhou Kaitu Chemical Co., Ltd
Tel
18802095185
Email
kang.sun@cato-chem.com
Country
China
ProdList
259
Advantage
58
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
Advantage
69
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30132
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
Advantage
81
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057 18501085097
Fax
010-89508210
Email
sales3.gd@hwrkchemical.com
Country
China
ProdList
7508
Advantage
55
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View Lastest Price from 2-Oxetanone manufacturers

Hebei Yibangte Import and Export Co. , Ltd.
Product
2-Oxetanone 57-57-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99.5%
Supply Ability
5000kg
Release date
2023-12-04
Hebei Mojin Biotechnology Co., Ltd
Product
2-Oxetanone 57-57-8
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-06-26
Hebei Guanlang Biotechnology Co., Ltd.
Product
2-Oxetanone 57-57-8
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100 mt
Release date
2021-09-28

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