57-57-8

Basic information

• Product Name: 2-Oxetanone
• Synonyms: Beta-propiolactone, 98%, pure;Propiolactone research grade;β-Propiolactone ,98%;BETA-PROPIOLACTONERESEARCH GRADE;β-Propiolactone,3-Hydroxypropionic acid lactone, Hydracrylic acid β-lactone;b-Propiolactone, Reagent;beta-Hydroxypropionic Acid Lactone 2-Oxetanone beta-Propionolactone;BETA-HYDROXYPROPIONIC ACID LACTONE
• CAS NO: 57-57-8
• Molecular Formula: C₃H₄O₂
• Molecular Weight: 72.06
• EINECS: 200-340-1
• Product Categories: Heterocycles;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactones;Organic Building Blocks;Intermediates & Fine Chemicals;Miscellaneous Reagents;Pharmaceuticals
• Mol File: 57-57-8.mol

Chemical Properties

• Melting Point: −33 °C(lit.)
• Boiling Point: 162 °C(lit.)
• Flash Point: 158 °F
• Appearance: /Liquid
• Density: 1.146 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.21mmHg at 25°C
• Refractive Index: n20/D 1.412(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with acetone, alcohol, chloroform, and ether (Windholz et al., 1983)
• Water Solubility: 37 g/100 mL
• Sensitive: Moisture Sensitive
• Stability: Moisture Sensitive, Very Hygroscopic
• Merck: 14,7820
• CAS DataBase Reference: 2-Oxetanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxetanone(57-57-8)
• EPA Substance Registry System: 2-Oxetanone(57-57-8)

Safety Data

• Hazard Codes: T+
• 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
• Hazardous Substances Data: 57-57-8(Hazardous Substances Data)

Usage

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 ℃.

InChI:InChI=1/C3H4O2/c4-3-1-2-5-3/h1-2H2

Synthetic route

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

Conditions	Yield
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) → β-Propiolactone (57-57-8)

Conditions	Yield
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) + carbon monoxide (201230-82-2) → β-Propiolactone (57-57-8) + acetaldehyde (75-07-0)

Conditions	Yield
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) → β-Propiolactone (57-57-8)

Conditions	Yield
With P(MeNCH2CH2)3N In acetonitrile at 25℃; for 0.0833333h;	90%

oxirane (75-21-8) + carbon monoxide (201230-82-2) → succinic acid anhydride (108-30-5) + β-Propiolactone (57-57-8)

Conditions	Yield
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) + formaldehyd (50-00-0) → β-Propiolactone (57-57-8)

Conditions	Yield
With aluminium trichloride; zinc(II) chloride In acetone	75%
With acetone; zinc(II) chloride
With β-Propiolactone

oxirane (75-21-8) + carbon monoxide (201230-82-2) → β-Propiolactone (57-57-8)

Conditions	Yield
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) + formaldehyd (50-00-0) + diethyl ether (60-29-7) → β-Propiolactone (57-57-8)

Conditions	Yield
in Gegenwart verschiedener Katalysatoren;

Ketene (463-51-4) + formaldehyd (50-00-0) + triethyl phosphate (78-40-0) → β-Propiolactone (57-57-8)

Ketene (463-51-4) + formaldehyd (50-00-0) + trifluoroborane diethyl ether (109-63-7) → β-Propiolactone (57-57-8)

2-chloropropionate anion → β-Propiolactone (57-57-8)

Conditions	Yield
With base In water; dimethyl sulfoxide at 34℃;
In water; dimethyl sulfoxide at 34℃; Rate constant; Mechanism;

β-iodo-propionate sodium → β-Propiolactone (57-57-8)

Conditions	Yield
With silver nitrate

Ketene (463-51-4) + formaldehyd (50-00-0) + HgCl2 → β-Propiolactone (57-57-8)

Ketene (463-51-4) + formaldehyd (50-00-0) + liquid propiolactone → β-Propiolactone (57-57-8)

Conditions	Yield
in Gegenwart verschiedener Katalysatoren;

Ketene (463-51-4) + formaldehyd (50-00-0) + Al2O3 + SiO2 → β-Propiolactone (57-57-8)

Ketene (463-51-4) + formaldehyd (50-00-0) + aluminium trichloride (7446-70-0) + ZnCl2 → β-Propiolactone (57-57-8)

Ketene (463-51-4) + formaldehyd (50-00-0) + diethyl ether (60-29-7) + ZnCl2 → β-Propiolactone (57-57-8)

Ketene (463-51-4) + formaldehyd (50-00-0) + aluminium trichloride (7446-70-0) + diethyl ether (60-29-7) + ZnCl2 → β-Propiolactone (57-57-8)

Ketene (463-51-4) + formaldehyd (50-00-0) + Zn(ClO4)2 → β-Propiolactone (57-57-8)

water (7732-18-5) + sodium-3-iodopropionate (77545-96-1) + silver nitrate → β-Propiolactone (57-57-8)

3-amino propanoic acid (107-95-9) → β-Propiolactone (57-57-8)

Conditions	Yield
With sodium dihydrogenphosphate; sodium perchlorate; sodium nitrite at 24.84℃; pH=3.00; Kinetics;

L-glutamic acid (56-86-0) → maleiimide (541-59-3) + Succinimide (123-56-8) + pyrrole (109-97-7) + β-Propiolactone (57-57-8) + 3-Methylpyridine (108-99-6) + ethanol (64-17-5) + acetic acid (64-19-7) + acrylonitrile (107-13-1) + 7-deazahypoxanthine (3680-71-5) + acetonitrile (75-05-8) + propiononitrile (107-12-0)

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

...Expand

oxirane (75-21-8) + carbon monoxide (201230-82-2) → succinic acid anhydride (108-30-5) + β-Propiolactone (57-57-8) + acetaldehyde (75-07-0)

Conditions	Yield
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) + β-Propiolactone (57-57-8) → methyl ester (3-hydroxy) propionic acid (6149-41-3)

Conditions	Yield
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) + acetic acid (64-19-7) → 3-acetoxypropionic acid (4272-12-2)

Conditions	Yield
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) → 3-hydroxypropionamide (2651-43-6)

Conditions	Yield
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) + sodium methylate (124-41-4) → methyl ester (3-hydroxy) propionic acid (6149-41-3)

Conditions	Yield
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) + 1-amino-2-propene (107-11-9) → C6H11NO2 (1021495-88-4)

Conditions	Yield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;	100%

β-Propiolactone (57-57-8) → 3-hydroxypropanoic acid sodium salt (6487-38-3)

Conditions	Yield
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) + 12-methoxydodecylmagnesium bromide → 15-methoxypentadecanoic acid (78350-13-7)

Conditions	Yield
With copper(l) iodide; dimethylsulfide In tetrahydrofuran at 0℃; for 3h;	99%

β-Propiolactone (57-57-8) → propionic acid (802294-64-0)

Conditions	Yield
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) → 2-chloropropionyl chloride (625-36-5)

Conditions	Yield
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) + potassium tert-butylate (865-47-4) → tert-Butyl acrylate (1663-39-4)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.25h;	96%

β-Propiolactone (57-57-8) + butyl magnesium bromide (693-04-9) → oenanthic acid (111-14-8)

Conditions	Yield
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) + Triethylammonium-3-methyl-3-phenyl-tiolcarbazat → 3-(3-Methyl-3-phenyl-carbazoylthio)-propionsaeure

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

methylthioglycollate + β-Propiolactone (57-57-8) → 3-(2-methoxy-2-oxoethylsulfanyl)-propanoic acid (93274-67-0)

Conditions	Yield
	94%

(E)-N-(naphthalen-1-yl)-1-phenylmethanimine (78569-36-5) + β-Propiolactone (57-57-8) → 1-(1-naphthyl)-5-ethyl-2-pyrrolidinone

Conditions	Yield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;	93%

dimethyl(2,2'-bipyridine)platinum(II) (52594-52-2) + β-Propiolactone (57-57-8) → {(methyl)2(CH2CH2C(O)O)(2,2'-bipyridine)platinum}

Conditions	Yield
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) + 5’-deoxy-5’-(benzylthio)adenosine (5135-39-7) → (benzyl)(5’-deoxyadenosyl)-(3-propionate)sulfonium salt

Conditions	Yield
With formic acid at 20℃; for 2h; Inert atmosphere;	93%

n-butyl magnesium bromide (693-03-8) + β-Propiolactone (57-57-8) → oenanthic acid (111-14-8)

Conditions	Yield
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) + bromopentene (1119-51-3) → oct-7-enoic acid (18719-24-9)

Conditions	Yield
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) + benzyl alcohol (100-51-6) → 3-(benzyloxy)propanoic acid (27912-85-2)

Conditions	Yield
at 75℃; for 24h;	91%

β-Propiolactone (57-57-8) + potassium methanolate (865-33-8) → acrylic acid methyl ester (292638-85-8)

Conditions	Yield
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) + C10H20ClMgO(1-)*Cl(1-)*Mg(2+) → 13-hydroxytridecanoic acid (7735-38-8)

Conditions	Yield
dilithium tetrachlorocuprate In tetrahydrofuran at -10℃; for 1h;	90%

β-Propiolactone (57-57-8) + N-benzylidene ethylamine (27845-47-2) → 1-ethyl-5-phenyl-2-pyrrolidinone

Conditions	Yield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;	90%

β-Propiolactone (57-57-8) + butanone (78-93-3) → 5-ethyl-5-methyl-dihydro-furan-2-one (2865-82-9)

Conditions	Yield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;	90%

methanol (67-56-1) + β-Propiolactone (57-57-8) + sodium methylate (124-41-4) → methyl ester (3-hydroxy) propionic acid (6149-41-3)

Conditions	Yield
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) + 4-Fluoro-3-hydroxy-benzoic acid methyl ester (214822-96-5) → 3-(2-carboxy-ethoxy)-4-fluoro-benzoic acid methyl ester (909407-23-4)

Conditions	Yield
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) + n-Dodecylamine (124-22-1) → 3-(dodecylamino)propanoic acid (1462-54-0)

Conditions	Yield
In acetonitrile	89%
With acetonitrile

Upstream product

• 463-51-4 Ketene 
• 50-00-0 formaldehyd 
• 60-29-7 diethyl ether 
• 78-40-0 triethyl phosphate 
• 109-63-7 trifluoroborane diethyl ether 
• 590-92-1 3-Bromopropionic acid 
• 7446-70-0 aluminium trichloride 
• 7732-18-5 water 
• 77545-96-1 sodium-3-iodopropionate 
• 5009-27-8 cyclopropanone 
• 75-21-8 oxirane 
• 201230-82-2 carbon monoxide 
• 107-95-9 3-amino propanoic acid 
• 504-63-2 trimethyleneglycol 

Downstream Products

• 26371-07-3 1-piperidinepropionic acid 
• 104-58-5 3-piperidinopropan-1-ol 
• 4497-04-5 3-morpholin-4-ylpropionic acid 
• 110359-84-7 3-(2-ethyl-phenylsulfanyl)-propionic acid 
• 130234-70-7 RM₄₈₅₇ 
• 5439-15-6 3-(2-amino-pyridinium)-propionate 
• 5439-15-6 3-(2-imino-2H-[1]pyridyl)-propionic acid 
• 5439-14-5 3,4-dihydro-pyrido[1,2-a]pyrimidin-2-one 
• 830-96-6 Indole-3-propionic acid 
• 5724-76-5 3-succinimidopropionic acid 
• 1136-87-4 3-(2-methyl-1H-indol-3-yl)propanoic acid 
• 292638-85-8 acrylic acid methyl ester 
• 3852-09-3 methyl 3-methoxypropionate 
• 6001-87-2 methyl 3-chloropropionate 

Relevant articles and documents

Multisite catalysis: A mechanistic study of β-lactone synthesis from epoxides and CO - Insights into a difficult case of homogeneous catalysis

Carbonylation of epoxides with a combination of Lewis acids and cobalt carbonyls was studied by both theoretical and experimental methods. Only multisite catalysis opens a low-energy pathway for trans opening of oxirane rings. This ring-opening reaction is not easily achieved with a single-site metal catalyst due to structural and thermodynamic constraints. The overall reaction pathway includes epoxide ring opening, which requires both a Lewis acid and a tetracarbonylcobaltate nucleophile, yielding a cobalt alkyl - alkoxy-Lewis acid moiety. After CO insertion into the Co-Calkyl bond, lactone formation results from a nucleophilic attack of the alkoxy Lewis acid entity on the acylium carbon atom. A theoretical study indicates a marked influence of the Lewis acid on both ring-opening and lactone-formation steps, but not on carbonylation. Strong Lewis acids induce fast ring opening, but slow lactone formation, and visa versa: a good balance of Lewis acidity would give the fastest catalytic cycle as all steps have low barriers. Experimentally, carbonylation of propylene oxide to β-butyrolactone was monitored by online ATR-IR techniques with a mixture of tetracarbonylcobaltate and Lewis acids, namely BF3, Me3Al, Et2Al+ · diglyme, and a combination of Me3Al/dicobaltoctacarbonyl. We found that the last two mixtures are extremely active in lactone formation.

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

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.

Acrylonitrile Derivatives from Epoxide and Carbon Monoxide Reagents

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

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

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.

ACRYLIC ACID PRODUCTION METHODS

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.

Molecular products from the thermal degradation of glutamic acid

The thermal behavior of glutamic acid was investigated in N2 and 4% O2 in N2 under flow reactor conditions at a constant residence time of 0.2 s, within a total pyrolysis time of 3 min at 1 atm. The identification of the main pyrolysis products has been reported. Accordingly, the principal products for pyrolysis in order of decreasing abundance were succinimide, pyrrole, acetonitrile, and 2-pyrrolidone. For oxidative pyrolysis, the main products were succinimide, propiolactone, ethanol, and hydrogen cyanide. Whereas benzene, toluene, and a few low molecular weight hydrocarbons (propene, propane, 1-butene, and 2-butene) were detected during pyrolysis, no polycyclic aromatic hydrocarbons (PAHs) were detected. Oxidative pyrolysis yielded low molecular weight hydrocarbon products in trace amounts. The mechanistic channels describing the formation of the major product succinimide have been explored. The detection of succinimide (major product) and maleimide (minor product) from the thermal decomposition of glutamic acid has been reported for the first time in this study. Toxicological implications of some reaction products (HCN, acetonitrile, and acyrolnitrile), which are believed to form during heat treatment of food, tobacco burning, and drug processing, have been discussed in relation to the thermal degradation of glutamic acid.

PROCESS FOR BETA-LACTONE PRODUCTION

The present application provides a method for producing an beta-lactone product. The method includes the steps of: reacting an epoxide, a solvent with a carbonylation catalyst and carbon monoxide to produce a reaction stream comprising a beta-lactone then separating a portion of the beta-lactone in the reaction stream from the solvent and carbonylation catalyst to produce: i) a beta-lactone stream with the beta-lactone, and ii) a catalyst recycling stream including the carbonylation catalyst and the high boiling solvent; and adding the catalyst recycling stream to the feed stream.

CARBONYLATION OF EPOXIDES

The present invention pertains to a process for the carbonylation of an epoxide by reacting it with carbon monoxide in the presence of a catalyst system containing two components, wherein the first component is a source of one or more metals selected from the group consisting of cobalt, ruthenium and rhodium, and the second component is a coordination complex of a tetrapyrrole compound with one or more of the metals belonging to the group consisting of groups IIIA and IIIB of the periodic system, lanthanides and actinides. The present invention also pertains a process for the preparation of catalyst system, and to the use of such catalyst system for the carbonylation of epoxides.

Generation of alkyl hypochlorites in oxidation of alcohols with carbon tetrachloride catalyzed by vanadium and manganese compounds

Primary alcohols and diols with various structures were subjected to transformations into esters, aldehydes, ketones, and lactones under the action of carbon tetrachloride in the presence of manganese compounds (MnCl 2, MnO2, Mn(OAc)2, Mn(acac)3) and vanadium compounds (VCl5, V2O5, VO(acac) 2) as catalysts. These transformation proceeded with the involvement of alkyl hypochlorites, which were generated in the course of oxidation of alcohols with carbon tetrachloride catalyzed by manganese or vanadium compounds. The optimum molar ratios between the catalyst and reagents were determined, and the reaction conditions for the highly selective synthesis of esters, aldehydes, ketones, and lactones from alcohols were found.