beta-Propiolactone

Base Information

• Chemical Name: beta-Propiolactone
• CAS No.: 57-57-8
• Molecular Formula: C3H4O2
• Molecular Weight: 72.0636
• Hs Code.: 29322090
• European Community (EC) Number: 200-340-1
• ICSC Number: 0555
• NSC Number: 758422,21626
• UN Number: 2810
• UNII: 6RC3ZT4HB0
• DSSTox Substance ID: DTXSID8021197
• Nikkaji Number: J2.327B
• Wikipedia: Beta-Propiolactone
• Wikidata: Q420715
• NCI Thesaurus Code: C44339
• Metabolomics Workbench ID: 57193
• ChEMBL ID: CHEMBL1200627
• Mol file: 57-57-8.mol

Synonyms:beta Propiolactone;beta-Propiolactone;Propanolide;Propiolactone

Chemical Property of beta-Propiolactone

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 2.21mmHg at 25°C
• Melting Point: -33 °C(lit.)
• Refractive Index: n20/D 1.412(lit.)
• Boiling Point: 161.999 °C at 760 mmHg
• Flash Point: 35.01 °C
• PSA: 26.30000
• Density: 1.231 g/cm³
• LogP: -0.06670
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with acetone, alcohol, chloroform, and ether (Windholz et al., 1983)
• Water Solubility.: 37 g/100 mL
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 72.021129366
• Heavy Atom Count: 5
• Complexity: 57.9
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

β-Propiolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 45-26-36/38
• Safety Statements: 53-45-99

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Lactones
• Canonical SMILES: C1COC1=O
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C on spraying.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is irritating to the skin and respiratory tract.
• Effects of Long Term Exposure: This substance is probably carcinogenic to humans.
• 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.
• Uses: Reacts with bacteriphage DNA causing inactivation, repair and recombination antiandrogen Versatile intermediate in organic synthesis.

Technology Process of beta-Propiolactone

There total 26 articles about beta-Propiolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

trimethyleneglycol (504-63-2) → β-Propiolactone (57-57-8)

Guidance literature:

With tetrachloromethane; bis(acetylacetonate)oxovanadium; at 100 ℃; for 1h;

DOI:10.1023/A:1021668011691

Reference yield: 94.0%

cyclopropanone (5009-27-8) → β-Propiolactone (57-57-8)

Guidance literature:

With oxygen; benzaldehyde; nickel(II) iodide; Dowex 50W; iron(II); In 1,2-dichloro-ethane; at 20 ℃; for 15h;

Reference yield: 90.0%

3-Bromopropionic acid (590-92-1) → β-Propiolactone (57-57-8)

Guidance literature:

With P(MeNCH₂CH₂)3N; In acetonitrile; at 25 ℃; for 0.0833333h;

DOI:10.1021/jo962310z

upstream raw materials:

Ketene

formaldehyd

diethyl ether

triethyl phosphate

Downstream raw materials:

N,N-Dipropyl-β-alanin

3-acetoxypropionic acid

acide phenylthio-3 propanoique

3-(4-chlorophenoxy)propionic acid

Refernces

• 1、 Molnar, Ferenc,Luinstra, Gerrit A.,Allmendinger, Markus,Rieger, Bernhard. "Multisite catalysis: A mechanistic study of β-lactone synthesis from epoxides and CO - Insights into a difficult case of homogeneous catalysis". . p. 1273 - 1280. Retrieved 2003.
• 2、 -. "PROCESSES FOR PRODUCING BETA-LACTONE AND BETA-LACTONE DERIVATIVES WITH HETEROGENOUS CATALYSTS". Paragraph 0185-0192. . Retrieved 2019/02/24.
• 3、 -. "PROCESS FOR THE PRODUCTION OF ACID ANHYDRIDES FROM EPOXIDES". Page/Page column 50-51. . Retrieved 2013/08/28.