123-62-6 Usage
Chemical Description
Propionic anhydride is another carboxylic acid anhydride that is used in organic synthesis.
Description
Propionic anhydride, with the molecular formula (CH3CH2CO)2O, is a colorless acid anhydride that is widely used as a reagent in organic synthesis. It is a colorless liquid with a strong, pungent, and unpleasant odor. It is soluble in methanol, ethanol, ether, chloroform, and alkali, but decomposes in water.
Uses
Used in Perfumery and Flavor Industry:
Propionic anhydride is used as an esterifying agent for certain perfume oils, fats, and oils, particularly cellulose, to enhance their properties and characteristics.
Used in Organic Synthesis:
Propionic anhydride is used as a reagent in organic synthesis, enabling the production of various chemical compounds and intermediates.
Used in Alkyd Resin Production:
Propionic anhydride is used in the production of alkyd resins, which are important in the manufacturing of coatings, paints, and other related products.
Used in Dye and Drug Manufacturing:
Propionic anhydride is utilized in the production of dyestuffs and drugs, contributing to the development of various colorants and pharmaceuticals.
Used as a Dehydrating Agent:
Propionic anhydride has been used as a dehydrating agent in some sulfonations and nitrations, playing a crucial role in these chemical processes.
Used in the Preparation of Propionyl Derivatives:
Propionic anhydride was previously used in the preparation of α and β-1-propionyl derivatives of glucopyranose tetra-acetate, which are important in the synthesis of various organic compounds.
Air & Water Reactions
Decomposes exothermically in water to form a corrosive solution of propionic acid [Merck, 11th ed. 1989].
Reactivity Profile
Propionic anhydride reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases.
Hazard
Strong irritant to tissue.
Health Hazard
Inhalation causes irritation of eyes and respiratory tract. Contact with liquid causes burns of eyes and skin. Ingestion causes burns of mouth and stomach.
Fire Hazard
Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Flammability and Explosibility
Nonflammable
Safety Profile
Moderately toxic by
ingestion. Mildly toxic by skin contact. A
corrosive irritant to skin, eyes, and mucous
membranes. Combustible when exposed to
heat or flame; can react with oxidizing
materials. To fight fire, use CO2, dry
chemical. When heated to decomposition it
emits acrid smoke and irritating fumes. Used
as an esterifyng agent and dehydrating
agent. See also ANHYDRIDES.
Safety
Propanoic anhydride is strong smelling and corrosive, and will cause burns on contact with skin. Vapour can burn eyes and lungs.
Synthesis
Propanoic anhydride has been prepared by dehydration of propanoic acid using ketene : 2 CH3CH2CO2H + CH2= C= O → (CH3CH2CO)2O + CH3CO2H.
Potential Exposure
Used in the manufacture of perfumes,
flavorings, alkyd resins; dyestuffs, pharmaceuticals; as an
esterifying agent for fats, oils, and cellulose; dehydrating
medium for nitrations and sulfonations.
Shipping
UN2496 Propionic anhydride, Hazard class: 8;
Labels: 8-Corrosive material.
Purification Methods
Shake the anhydride with P2O5 for several minutes, then distil. [Beilstein 2 IV 722.]
Incompatibilities
Vapors may form explosive mixture with
air. Incompatible with oxidizers (chlorates, nitrates, perox-
ides, permanganates, perchlorates, chlorine, bromine, fluo-
rine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids,
oxoacids, epoxides, reducing agents; alcohols and metals.
Contact with water forms heat 1 flammable propionic acid.
Compounds of the carboxyl group react with all bases, both
inorganic and organic (i.e., amines) releasing substantial
heat, water and a salt that may be harmful. Incompatible
with arsenic compounds (releases hydrogen cyanide gas),
diazo compounds, dithiocarbamates, isocyanates, mercap-
tans, nitrides, and sulfides (releasing heat, toxic and possibly
flammable gases), thiosulfates and dithionites (releasing
hydrogen sulfate and oxides of sulfur).
Waste Disposal
Use a licensed professional
waste disposal service to dispose of this material. Dissolve
or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner
and scrubber. All federal, state, and local environmental
regulations must be observed.
Check Digit Verification of cas no
The CAS Registry Mumber 123-62-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 123-62:
(5*1)+(4*2)+(3*3)+(2*6)+(1*2)=36
36 % 10 = 6
So 123-62-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O3/c1-3-5(7)9-6(8)4-2/h3-4H2,1-2H3
123-62-6Relevant articles and documents
Diastereoselective synthesis of a lilac aldehyde isomer and its electrophysiological detection by a moth
Schneider, Marc-Andre,Doetterl, Stefan,Seifert, Karlheinz
, p. 1252 - 1259 (2013)
The monoterpene lilac aldehyde (=2-(5-ethenyl-5-methyloxolan-2-yl)propanal) is a widespread flower scent. Lilac aldehyde is emitted in high amounts from nocturnal plant species, and it is highly attractive to nocturnal moth pollinators, such as Hadena bicruris, the pollinating seed predator of Silene latifolia. Lilac aldehyde possesses three stereogenic centers and can occur in eight stereoisomers which induce different antennal responses in H. bicruris. The distribution pattern of stereoisomers differs among plant species, and if H. bicruris has different receptors for detecting different isomers, it may use these differences to discriminate flowers of S. latifolia hosts from flowers of non-host plants. To investigate the question whether the moths have in their antennae one olfactory receptor or several different receptors for the detection of the single lilac aldehyde isomers, (2S,2′S,5′S)-lilac aldehyde was diastereoselectively synthesized. (2S,2′S,5′S)-Lilac aldehyde and its isomeric mixture were tested electrophysiologically on antennae of H. bicruris. The results displayed antennal responses, which are characteristic for a single receptor that detects the different lilac aldehyde isomers. Copyright
A facile method for Rh-catalyzed decarbonylativeortho-C-H alkylation of (hetero)arenes with alkyl carboxylic acids
Tian, Yiqiang,Liu, Xiaojie,He, Bangyue,Ren, Yuxi,Su, Weiping
, p. 19827 - 19831 (2021)
A facile and effective method for Rh-catalyzed directortho-alkylation of C-H bonds in (hetero)arenes with commercially available carboxylic acids has been developed. This strategy was initiated byin situconversion of carboxylic acids to anhydrides which, without isolation, underwent Rh-catalyzed direct decarbonylative cross-coupling of aryl carboxamides containing 8-aminoquinoline. The reaction proceeds with high regioselectivity and exhibits a broad substrate scope as well as functional group tolerance.
Generation of basic centers in high-silica zeolites and their application in gas-phase upgrading of bio-oil
Keller, Tobias C.,Rodrigues, Elodie G.,Perez-Ramirez, Javier
, p. 1729 - 1738 (2014)
High-silica zeolites have been reported recently as efficient catalysts for liquid- and gas-phase condensation reactions because of the presence of a complementary source of basicity compared to Al-rich basic zeolites. Herein, we describe the controlled generation of these active sites on silica-rich FAU, BEA, and MFI zeolites. Through the application of a mild base treatment in aqueous Na2CO3, alkali-metal-coordinating defects are generated within the zeolite whereas the porous properties are fully preserved. The resulting catalysts were applied in the gas-phase condensation of propanal at 673 K as a model reaction for the catalytic upgrading of pyrolysis oil, for which an up to 20-fold increased activity compared to the unmodified zeolites was attained. The moderate basicity of these new sites leads to a coke resistance superior to traditional base catalysts such as CsX and MgO, and comparable activity and excellent selectivity is achieved for the condensation pathways. Through strategic acid and base treatments and the use of magic-angle spinning NMR spectroscopy, the nature of the active sites was investigated, which supports the theory of siloxy sites as basic centers. This contribution represents a key step in the understanding and design of high-silica base catalysts for the intermediate deoxygenation of crude bio-oil prior to the hydrotreating step for the production of second-generation biofuels. Creating new basic sites: Through activation treatments in alkaline media, basic sites with high activity, stability, and selectivity are generated in high-silica FAU, BEA, and MFI zeolites, which enable the efficient deoxygenation of pyrolysis oil by condensation reactions. Intermediate bio-oil upgrading is key for the sustainable and profitable production of advanced biofuels.
Isothiourea-Catalyzed Atroposelective N-Acylation of Sulfonamides
Ong, Jun-Yang,Ng, Xiao Qian,Lu, Shenci,Zhao, Yu
supporting information, p. 6447 - 6451 (2020/09/02)
We report herein an atroposelective N-acylation of sulfonamides using a commercially available isothiourea catalyst, (S)-HBTM, with a simple procedure. The N-sulfonyl anilide products can be obtained in good to high enantiopurity, which represents a new axially chiral scaffold. The application of the product as a chiral iodine catalyst is also demonstrated for the asymmetric α-oxytosylation of propiophenone.
Anhydrides from aldehydes or alcohols via oxidative cross-coupling
Gaspa, Silvia,Amura, Ida,Porcheddu, Andrea,De Luca, Lidia
supporting information, p. 931 - 939 (2017/02/10)
A novel type of metal-free oxidative cross-coupling for the synthesis of symmetrical and mixed anhydrides from aldehydes or benzylic alcohols has been developed. The aldehydes or alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with an array of carboxylic acids. The methodology has a general applicability, and was successfully employed to prepare either aromatic or aliphatic symmetrical anhydrides and mixed anhydrides, which are very unstable compounds.