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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

57-57-8 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (B23197)  beta-Propiolactone, 97%   

  • 57-57-8

  • 1g

  • 249.0CNY

  • Detail
  • Alfa Aesar

  • (B23197)  beta-Propiolactone, 97%   

  • 57-57-8

  • 5g

  • 1049.0CNY

  • Detail
  • Alfa Aesar

  • (B23197)  beta-Propiolactone, 97%   

  • 57-57-8

  • 25g

  • 2930.0CNY

  • Detail

57-57-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name β-propiolactone

1.2 Other means of identification

Product number -
Other names β-Propiolactone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. beta-Propiolactone is used for vaccines, tissue grafts, surgical instruments, and enzymes, as a sterilant of blood plasma, water, milk, and nutrient broth, and as a vapor-phase disinfectant in enclosed spaces. Its sporicidal action is used against vegetative bacteria, pathologic fungi, and viruses. beta-Propiolactone is also used as a chemical intermediate.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57-57-8 SDS

57-57-8Synthetic route

trimethyleneglycol
504-63-2

trimethyleneglycol

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
With tetrachloromethane; bis(acetylacetonate)oxovanadium at 100℃; for 1h;98%
With [RuCl2(PPh3)2(2-PyCH21,3,5-triaza-7-phosphadamantane)].Br; potassium hydroxide In water for 48h; Reagent/catalyst; Schlenk technique; Reflux; Inert atmosphere; Green chemistry;95%
cyclopropanone
5009-27-8

cyclopropanone

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
With oxygen; benzaldehyde; nickel(II) iodide; Dowex 50W; iron(II) In 1,2-dichloro-ethane at 20℃; for 15h; Baeyer-Villiger oxidation;94%
oxirane
75-21-8

oxirane

carbon monoxide
201230-82-2

carbon monoxide

A

β-Propiolactone
57-57-8

β-Propiolactone

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 10343.2 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;A 92%
B 5%
[(C1TPP)Al][Co(CO)4] In sulfolane at -78 - 80℃; under 31029.7 Torr; Product distribution / selectivity; Inert atmosphere;A 46.8%
B 7.9%
With Hexamethylbenzene; [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)][tetracarbonylcobaltate] In tetrahydrofuran at 60℃; under 10343.2 Torr; for 3h; Catalytic behavior; Pressure; Reagent/catalyst; Solvent; Temperature; Glovebox; Inert atmosphere;A 92 %Spectr.
B 5 %Spectr.
3-Bromopropionic acid
590-92-1

3-Bromopropionic acid

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In acetonitrile at 25℃; for 0.0833333h;90%
oxirane
75-21-8

oxirane

carbon monoxide
201230-82-2

carbon monoxide

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;A 8%
B 88%
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 60℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;A 13%
B 81%
With Hexamethylbenzene; [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)][tetracarbonylcobaltate] In tetrahydrofuran at 60℃; under 31029.7 Torr; for 3h; Glovebox; Inert atmosphere;A 8 %Spectr.
B 88 %Spectr.
Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
With aluminium trichloride; zinc(II) chloride In acetone75%
With acetone; zinc(II) chloride
With β-Propiolactone
oxirane
75-21-8

oxirane

carbon monoxide
201230-82-2

carbon monoxide

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; [bis(triphenylphospine)nitrogen(1+)][Co(CO)4] In N,N-dimethyl-formamide at 80℃; under 46544.6 Torr; for 24h;44%
Hexamethylbenzene; [(C1TPP)Al][Co(CO)4] In tetrahydrofuran at -78 - 30℃; under 31029.7 Torr; for 3h; Product distribution / selectivity; Molecular sieve; Inert atmosphere;44%
With trimethylaluminum; dicobalt octacarbonyl In diethylene glycol dimethyl ether; toluene at 75℃; under 45004.5 Torr; for 5h;
Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

diethyl ether
60-29-7

diethyl ether

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
in Gegenwart verschiedener Katalysatoren;
Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

triethyl phosphate
78-40-0

triethyl phosphate

β-Propiolactone
57-57-8

β-Propiolactone

Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

trifluoroborane diethyl ether
109-63-7

trifluoroborane diethyl ether

β-Propiolactone
57-57-8

β-Propiolactone

2-chloropropionate anion

2-chloropropionate anion

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
With base In water; dimethyl sulfoxide at 34℃;
In water; dimethyl sulfoxide at 34℃; Rate constant; Mechanism;
β-iodo-propionate sodium

β-iodo-propionate sodium

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
With silver nitrate
Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

HgCl2

HgCl2

β-Propiolactone
57-57-8

β-Propiolactone

Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

liquid propiolactone

liquid propiolactone

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
in Gegenwart verschiedener Katalysatoren;
Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

Al2O3

Al2O3

SiO2

SiO2

β-Propiolactone
57-57-8

β-Propiolactone

Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

aluminium trichloride
7446-70-0

aluminium trichloride

ZnCl2

ZnCl2

β-Propiolactone
57-57-8

β-Propiolactone

Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

diethyl ether
60-29-7

diethyl ether

ZnCl2

ZnCl2

β-Propiolactone
57-57-8

β-Propiolactone

Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

aluminium trichloride
7446-70-0

aluminium trichloride

diethyl ether
60-29-7

diethyl ether

ZnCl2

ZnCl2

β-Propiolactone
57-57-8

β-Propiolactone

Ketene
463-51-4

Ketene

formaldehyd
50-00-0

formaldehyd

Zn(ClO4)2

Zn(ClO4)2

β-Propiolactone
57-57-8

β-Propiolactone

water
7732-18-5

water

sodium-3-iodopropionate
77545-96-1

sodium-3-iodopropionate

silver nitrate

silver nitrate

β-Propiolactone
57-57-8

β-Propiolactone

3-amino propanoic acid
107-95-9

3-amino propanoic acid

β-Propiolactone
57-57-8

β-Propiolactone

Conditions
ConditionsYield
With sodium dihydrogenphosphate; sodium perchlorate; sodium nitrite at 24.84℃; pH=3.00; Kinetics;
L-glutamic acid
56-86-0

L-glutamic acid

A

maleiimide
541-59-3

maleiimide

B

Succinimide
123-56-8

Succinimide

C

pyrrole
109-97-7

pyrrole

D

β-Propiolactone
57-57-8

β-Propiolactone

E

3-Methylpyridine
108-99-6

3-Methylpyridine

F

ethanol
64-17-5

ethanol

G

acetic acid
64-19-7

acetic acid

H

acrylonitrile
107-13-1

acrylonitrile

I

7-deazahypoxanthine
3680-71-5

7-deazahypoxanthine

J

acetonitrile
75-05-8

acetonitrile

K

propiononitrile
107-12-0

propiononitrile

Conditions
ConditionsYield
With oxygen at 400℃; under 760.051 Torr; for 5.55556E-05h; Temperature; Inert atmosphere; Pyrolysis; Gas phase; Flow reactor;
oxirane
75-21-8

oxirane

carbon monoxide
201230-82-2

carbon monoxide

A

succinic acid anhydride
108-30-5

succinic acid anhydride

B

β-Propiolactone
57-57-8

β-Propiolactone

C

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With [(tetra(4-chlorophenyl)porphyrinato)aluminium(III)bis(tetrahydrofuran)][tetracarbonylcobaltate] at 80℃; under 31029.7 Torr; for 4h; Catalytic behavior; Glovebox; Inert atmosphere;A 50.8 %Spectr.
B 23.6 %Spectr.
C 5.5 %Spectr.
methanol
67-56-1

methanol

β-Propiolactone
57-57-8

β-Propiolactone

methyl ester (3-hydroxy) propionic acid
6149-41-3

methyl ester (3-hydroxy) propionic acid

Conditions
ConditionsYield
With sodium methylate at 50℃; for 1h;100%
With sulfuric acid at 0℃; for 18h;97%
With sodium methylate In methanol at 50℃; for 1.5h;90%
β-Propiolactone
57-57-8

β-Propiolactone

acetic acid
64-19-7

acetic acid

3-acetoxypropionic acid
4272-12-2

3-acetoxypropionic acid

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 4h;100%
With sulfuric acid at 20℃; for 4h;98.2%
With sulfuric acid for 2h; Ambient temperature;60%
With sulfuric acid
β-Propiolactone
57-57-8

β-Propiolactone

3-hydroxypropionamide
2651-43-6

3-hydroxypropionamide

Conditions
ConditionsYield
With ammonia In water at 0 - 20℃;100%
With ammonia at 100℃; unter Druck;
With ammonia; water
With ammonia In methanol at 20℃;
With ammonia In tetrahydrofuran at -78 - 3℃; for 2.58h; Sealed tube; regioselective reaction;66 %Spectr.
β-Propiolactone
57-57-8

β-Propiolactone

sodium methylate
124-41-4

sodium methylate

methyl ester (3-hydroxy) propionic acid
6149-41-3

methyl ester (3-hydroxy) propionic acid

Conditions
ConditionsYield
In methanol at 50℃; for 4h;100%
In methanol at 50℃; for 1h;69%
In methanol at 50℃; for 1h; Inert atmosphere;39%
β-Propiolactone
57-57-8

β-Propiolactone

1-amino-2-propene
107-11-9

1-amino-2-propene

C6H11NO2
1021495-88-4

C6H11NO2

Conditions
ConditionsYield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;100%
β-Propiolactone
57-57-8

β-Propiolactone

3-hydroxypropanoic acid sodium salt
6487-38-3

3-hydroxypropanoic acid sodium salt

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; Inert atmosphere;100%
With sodium hydroxide In water at 20℃;
Stage #1: β-Propiolactone With water
Stage #2: With sodium hydroxide pH=9.33;
With water; sodium hydroxide at 20℃; Inert atmosphere;1 g
β-Propiolactone
57-57-8

β-Propiolactone

12-methoxydodecylmagnesium bromide

12-methoxydodecylmagnesium bromide

15-methoxypentadecanoic acid
78350-13-7

15-methoxypentadecanoic acid

Conditions
ConditionsYield
With copper(l) iodide; dimethylsulfide In tetrahydrofuran at 0℃; for 3h;99%
β-Propiolactone
57-57-8

β-Propiolactone

propionic acid
802294-64-0

propionic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; W(OTf)6; hydrogen at 135℃; under 760.051 Torr; for 12h;99%
With palladium on activated carbon; W(OTf)6; hydrogen In neat (no solvent) at 135℃; under 760.051 Torr; for 12h; Reagent/catalyst;90 %Chromat.
β-Propiolactone
57-57-8

β-Propiolactone

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

Conditions
ConditionsYield
With bis(trichloromethyl) carbonate; N,N-dimethylpiperidine-4-carboxamide hydrochloride at 25℃; for 10h; Reagent/catalyst; Large scale;98%
With phosphorus pentachloride In benzene at 20℃; for 10h; Chlorination;87%
With tetrachloromethane; sulfuryl dichloride
With tetrachloromethane; phosphorus pentachloride
With thionyl chloride
β-Propiolactone
57-57-8

β-Propiolactone

potassium tert-butylate
865-47-4

potassium tert-butylate

tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.25h;96%
β-Propiolactone
57-57-8

β-Propiolactone

butyl magnesium bromide
693-04-9

butyl magnesium bromide

oenanthic acid
111-14-8

oenanthic acid

Conditions
ConditionsYield
With copper(l) chloride In tetrahydrofuran at -10℃;95%
With copper(I) bromide at -5℃; for 1h; Mechanism; Product distribution; other solvents, Grignard reagents, catalyst and temperature;
β-Propiolactone
57-57-8

β-Propiolactone

Triethylammonium-3-methyl-3-phenyl-tiolcarbazat

Triethylammonium-3-methyl-3-phenyl-tiolcarbazat

3-(3-Methyl-3-phenyl-carbazoylthio)-propionsaeure

3-(3-Methyl-3-phenyl-carbazoylthio)-propionsaeure

Conditions
ConditionsYield
In water at 20℃; for 1h;95%
methylthioglycollate

methylthioglycollate

β-Propiolactone
57-57-8

β-Propiolactone

3-(2-methoxy-2-oxoethylsulfanyl)-propanoic acid
93274-67-0

3-(2-methoxy-2-oxoethylsulfanyl)-propanoic acid

Conditions
ConditionsYield
94%
(E)-N-(naphthalen-1-yl)-1-phenylmethanimine
78569-36-5

(E)-N-(naphthalen-1-yl)-1-phenylmethanimine

β-Propiolactone
57-57-8

β-Propiolactone

1-(1-naphthyl)-5-ethyl-2-pyrrolidinone

1-(1-naphthyl)-5-ethyl-2-pyrrolidinone

Conditions
ConditionsYield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;93%
dimethyl(2,2'-bipyridine)platinum(II)
52594-52-2

dimethyl(2,2'-bipyridine)platinum(II)

β-Propiolactone
57-57-8

β-Propiolactone

{(methyl)2(CH2CH2C(O)O)(2,2'-bipyridine)platinum}

{(methyl)2(CH2CH2C(O)O)(2,2'-bipyridine)platinum}

Conditions
ConditionsYield
In acetone React. at room temp. for 4 h.; Elem. anal.;93%
In dichloromethane Kinetics; React. at 25°C.; Rate consts. given.;
In isopropyl alcohol Kinetics; React. at 25°C.; Rate consts. given.;
β-Propiolactone
57-57-8

β-Propiolactone

5’-deoxy-5’-(benzylthio)adenosine
5135-39-7

5’-deoxy-5’-(benzylthio)adenosine

(benzyl)(5’-deoxyadenosyl)-(3-propionate)sulfonium salt

(benzyl)(5’-deoxyadenosyl)-(3-propionate)sulfonium salt

Conditions
ConditionsYield
With formic acid at 20℃; for 2h; Inert atmosphere;93%
n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

β-Propiolactone
57-57-8

β-Propiolactone

oenanthic acid
111-14-8

oenanthic acid

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran at -30 - 0℃; for 0.0333333h; Product distribution; Mechanism; further reagents, solvents, temperatures, times, further β-propiolactones and Grignard reagents;92%
copper(l) chloride In tetrahydrofuran Product distribution; other solvents, catalysts;90%
copper(l) chloride at 0℃; for 0.25h;90%
With copper(l) iodide; dimethylsulfide 1) THF, -30 deg C, 30 min; 2) -30 deg C, 1 h, 0 deg C, 1 h; Yield given. Multistep reaction;
β-Propiolactone
57-57-8

β-Propiolactone

bromopentene
1119-51-3

bromopentene

oct-7-enoic acid
18719-24-9

oct-7-enoic acid

Conditions
ConditionsYield
Stage #1: bromopentene With magnesium In tetrahydrofuran for 2h; Heating;
Stage #2: β-Propiolactone With copper(l) chloride In tetrahydrofuran at 20℃; for 1h;
92%
β-Propiolactone
57-57-8

β-Propiolactone

benzyl alcohol
100-51-6

benzyl alcohol

3-(benzyloxy)propanoic acid
27912-85-2

3-(benzyloxy)propanoic acid

Conditions
ConditionsYield
at 75℃; for 24h;91%
β-Propiolactone
57-57-8

β-Propiolactone

potassium methanolate
865-33-8

potassium methanolate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.25h; Product distribution; other solvent, addition of 18-crown-6, other substrates;90%
In tetrahydrofuran at 20℃; for 0.25h;90%
β-Propiolactone
57-57-8

β-Propiolactone

C10H20ClMgO(1-)*Cl(1-)*Mg(2+)

C10H20ClMgO(1-)*Cl(1-)*Mg(2+)

13-hydroxytridecanoic acid
7735-38-8

13-hydroxytridecanoic acid

Conditions
ConditionsYield
dilithium tetrachlorocuprate In tetrahydrofuran at -10℃; for 1h;90%
β-Propiolactone
57-57-8

β-Propiolactone

N-benzylidene ethylamine
27845-47-2

N-benzylidene ethylamine

1-ethyl-5-phenyl-2-pyrrolidinone

1-ethyl-5-phenyl-2-pyrrolidinone

Conditions
ConditionsYield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;90%
β-Propiolactone
57-57-8

β-Propiolactone

butanone
78-93-3

butanone

5-ethyl-5-methyl-dihydro-furan-2-one
2865-82-9

5-ethyl-5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;90%
methanol
67-56-1

methanol

β-Propiolactone
57-57-8

β-Propiolactone

sodium methylate
124-41-4

sodium methylate

methyl ester (3-hydroxy) propionic acid
6149-41-3

methyl ester (3-hydroxy) propionic acid

Conditions
ConditionsYield
at 50℃; for 2h; Inert atmosphere;90%
Stage #1: methanol; β-Propiolactone; sodium methylate at -78℃;
Stage #2: With hydrogenchloride; methanol
β-Propiolactone
57-57-8

β-Propiolactone

4-Fluoro-3-hydroxy-benzoic acid methyl ester
214822-96-5

4-Fluoro-3-hydroxy-benzoic acid methyl ester

3-(2-carboxy-ethoxy)-4-fluoro-benzoic acid methyl ester
909407-23-4

3-(2-carboxy-ethoxy)-4-fluoro-benzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 4-Fluoro-3-hydroxy-benzoic acid methyl ester With potassium tert-butylate In tetrahydrofuran at 0 - 5℃; for 0.166667h;
Stage #2: β-Propiolactone In tetrahydrofuran at 0 - 50℃; for 4h;
Stage #3: With hydrogenchloride; water pH=0 - 2;
90%
β-Propiolactone
57-57-8

β-Propiolactone

n-Dodecylamine
124-22-1

n-Dodecylamine

3-(dodecylamino)propanoic acid
1462-54-0

3-(dodecylamino)propanoic acid

Conditions
ConditionsYield
In acetonitrile89%
With acetonitrile

57-57-8Relevant articles and documents

-

Stille,Divakaruni

, p. 1303 (1978)

-

Ruthenium-Promoted Acceptorless and Oxidant-Free Lactone Synthesis in Aqueous Medium

Bhatia, Anita,Kannan, Muthukumar,Muthaiah, Senthilkumar

supporting information, p. 721 - 725 (2019/03/26)

Ruthenium-catalyzed formation of lactones from diols in aqueous medium has been demonstrated. 1,3,5-Triazaphosphaadamantane (PTA) included water-soluble ruthenium complexes [RuCl 2 (PPh 3)(2,6-Py-(CH 2 -PTA) 2 ]·2Br and [RuCl 2 (PPh 3) 2 (2-PyCH 2 PTA)]·Br in the presence of KOH were found to be efficient for the synthesis of lactones from diols. The reported synthetic protocol is green as it uses water as solvent, avoids the use of any hydrogen acceptor/oxidant, and produces hydrogen as the only side product. Mechanistic studies revealed that lactone formation involved aldehyde intermediate and followed dehydrogenative pathway.

PROCESSES FOR PRODUCING BETA-LACTONE AND BETA-LACTONE DERIVATIVES WITH HETEROGENOUS CATALYSTS

-

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.

ACRYLIC ACID PRODUCTION METHODS

-

Page/Page column 12; 13; 14, (2013/09/12)

In one aspect, the present invention encompasses safe and efficient methods for providing highly pure acrylic acid. In certain embodiments, the inventive methods include the step of producing polypropiolactone from ethylene oxide at a first location, transporting the polymer to a second location and pyrolyzing the polypropiolactone to provide glacial acrylic acid. In certain embodiments, the step of pyrolyzing the polymer is performed continuously in conjunction with a polymerization process to make SAPs.

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