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Cas Database

108-24-7

108-24-7

Identification

  • Product Name:Acetic anhydride

  • CAS Number: 108-24-7

  • EINECS:203-564-8

  • Molecular Weight:102.09

  • Molecular Formula: C4H6O3

  • HS Code:29152400

  • Mol File:108-24-7.mol

Synonyms:Acetanhydride;Acetic acid, anhydride;Acetic oxide;Acetyl acetate;Acetyl anhydride;Acetyl ether;Acetyl oxide;Anhydrid kyseliny octove;Anhydride acetique;Anidride acetica;Octowy bezwodnik;UNII-2E48G1QI9Q;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes: C:Corrosive;

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed H314 Causes severe skin burns and eye damage H332 Harmful if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention . Liquid is volatile and causes little irritation on uncovered skin. However, causes severe burns when clothing is wet with the chemical or if it enters gloves or shoes. Causes skin and eye burns and irritation of respiratory tract. Nausea and vomiting may develop after exposure. (USCG, 1999) Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

  • Fire-fighting measures: Suitable extinguishing media If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. Use water spray to knock-down vapors. Special Hazards of Combustion Products: Irritating vapors are generated when heated. Behavior in Fire: Dangerous when exposed to heat or fire. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Consult an expert! Personal protection: chemical protection suit, face shield and filter respirator for acid gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Do NOT absorb in saw-dust or other combustible absorbents

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from food and feedstuffs and incompatible materials. See Chemical Dangers. Dry.Store in cool, dry, well-ventilated location. Outside or detached storage is preferred. Store away from heat, oxidizers, and sunlight. Exclude moisture from vapor space in storage tanks.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: (15-Min) Ceiling value: 5 ppm (20 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 204 Articles be found

Carbonylation of methyl acetate in the presence of polymeric rhodium-containing catalysts

Kolesnichenko, N. V.,Batov, A. E.,Markova, N. A.,Slivinsky, E. V.

, p. 259 - 262 (2002)

New catalytic systems based on RhCL3 and polymeric nitrogen- and oxygen-containing supports were proposed for the carbonylation of methyl acetate to acetic anhydride. The catalytic systems possess a high activity typical of homogeneous catalysts. The high activity is retained upon the repeated use of the catalyst separated from the reaction products. The nitrogen-containing polymers of the chitosan type serve as cocatalysts. In their presence, the induction period disappears, and the catalytically active species are stabilized, thus enabling the replacement of expensive LiI for cheaper salts of this metal.

Mono- and Polyanhydride Formation by Reaction of 2,2,4,4,6,6-Hexachlorotriazaphosphorine with Carboxylic Acids under Mild Conditions

Gregorio, Francesco Di,Marconi, Walter,Caglioti, Luciano

, p. 4569 - 4570 (1981)

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Concerted General Acid Catalysis in the Reaction of Acetate Ion with Water-soluble Carbodi-imide

Ibrahim, Ibrahim T.,Williams, Andrew

, p. 25 - 27 (1980)

An intermediate, identified as an O-acetylisourea, is observed spectroscopically in the reaction of a water-soluble carbodi-imide with acetate buffers; a stepwise mechanism for intermediate formation as currently accepted is excluded by the observation of general acid catalysis, while acetate ion attack on carbodi-imide is concerted with proton transfer, and monoanions of dicarboxylic acids react with carbodi-imide with intramolecular concerted proton transfer.

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Dacey,Coffin

, p. 315 (1939)

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Adkins,Thompson

, p. 2242 (1949)

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Cade,Gerrard

, p. 2030,2033 (1954)

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Selectivity Behavior in Hydrocarbonylation of Methyl Acetate Using Homogeneous Rh Complex Catalyst

Kelkar, A. A.,Chaudhari, R. V.

, p. 334 - 343 (1995)

Hydrocarbonylation of methyl acetate using various homogeneous transition metal complex catalysts has been studied.It was observed that Rh(CO)Cl(PPh3)2 was the most active and selective catalyst for ethylidene diacetate synthesis.The effect of the catalyst, methyl acetate, and methyl iodide concentrations; temperature; and partial pressures of CO, H2, and various transition metal complexes as co-catalysts on the selectivity behavior has been studied.Palladium complexes were found to enhance the selectivity of ethylidene diacetate substantially.Catalyst concentration, partial pressures of CO and H2, and temperature also influence the selectivity pattern substantially.On the basis of these results, a possible reaction mechanism is discussed.

Degradation of a veterinary pharmaceutical product in water by electro-oxidation using a BDD anode

Espinoza, C.,Contreras, N.,Berros, C.,Salazar, R.

, p. 2507 - 2511 (2014)

The electrochemical oxidation (EO) treatment in water of Fantetra, a veterinary drug widely used in Chile, and its components: oxytetracycline hydrochloride, phtalylsulfathiazole and diphenhydramine, has been carried out at constant current using a BDD/Stainless steel system. First, solutions of each drug were electrolyzed following the decay of the absorbance of each compound and total organic carbon abatement. The mineralization of the Fantetra commercial formulation was also studied. An analysis of the degradation by-products was made by high performance liquid chromatography. Thus, during the degradation of each pharmaceutical by the electrochemical oxidation process, aliphatic carboxylic acids were detected prior to their complete mineralization to CO2 and nitrogen ions, while NO3- and NH4+ remain in the treated solution. This is an essential preliminary step towards the applicability of the EO processes for the treatment of wastewater containing pharmaceutical compounds.

Technological features of the reaction of α-tocopherol acetylation

Bulychev

, p. 331 - 332 (1998)

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Weinshenker,Shen

, p. 3281,3282, 3283 (1972)

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Kremann,Roesler

, p. 359 (1922)

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The atmospheric oxidation of ethyl formate and ethyl acetate over a range of temperatures and oxygen partial pressures

Orlando, John J.,Tyndall, Geoffrey S.

, p. 397 - 413 (2010)

The Cl-atom-initiated oxidation of two esters, ethyl formate [HC(O)OCH 2CH3] and ethyl acetate [CH3C(O)OCH 2CH3], has been studied at pressures close to 1 atm as a function of temperature (249-325 K) and O2 partial pressure (50-700 Torr), using an environmental chamber technique. In both cases, Cl-atom attack at the CH2 group is most important, leading in part to the formation of radicals of the type RC(O)OCH(O?)CH3 [R = H, CH3]. The atmospheric fate of these radicals involves competition between reaction with O2 to produce an anhydride compound, RC(O)OC(O)CH3, and the so-called α-ester rearrangement that produces an organic acid, RC(O)OH, and an acetyl radical, CH3C(O). For both species studied, the α-ester rearrangement is found to dominate in air at 1 atm and 298 K. Barriers to the rearrangement of 7.7 ± 1.5 and 8.4 ± 1.5 kcal/mole are estimated for CH3C(O)OCH(O?)CH3 and HC(O)OCH(O?)CH3, respectively, leading to increased occurrence of the O2 reaction at reduced temperature. The data are combined with those obtained from similar studies of other simple esters to provide a correlation between the rate of occurrence of the α-ester rearrangement and the structure of the reacting radical.

TRIOXABICYCLO PENTANE IH PHOTOSENSITIZED OXYGENATION OF 2-DIAZO-3-BUTANONE

Ando, Wataru,Miyazaki, Hajime,Ito, Kenji,Auchi, Daikan

, p. 555 - 556 (1982)

Photosensitized oxygenation of 2-diazo-3-butanone at -78 deg C in CH2Cl2 gave trioxabicyclo pentane which has a long enough life time to allow chemical and spectroscopic characterization.

Infrared Study of the Surface Reaction of Gaseous Sulphuryl Chloride with Metal Carboxylates

Nakamura, Shigeaki

, p. 1 - 4 (1983)

The surface reaction of metal carboxylates RCO2M (R=H, Me, Et, Prn, and Pri; M=Li, Na, and K) with gaseous sulphuryl chloride has been monitored by i.r. spectroscopy.Reactions (I) and (II) take place. 2RCO2M+SO2Cl2RCOMSO4+RCOCl+MC

Adsorption of ethanoic acid on zeolites NaY and HY

Pope, Christopher G.

, p. 3647 - 3651 (1996)

The enthalpy and entropy of adsorption of ethanoic acid by the zeolite HY do not appear to be strongly influenced by the geometric constraints of the pore system. These results, which were predicted previously, contrast with those on H-ZSM-5. A companion examination of adsorption by NaY was complicated by chemical reactions which produced small amounts of ethanoate ions, water, ethanoic anhydride and methane. These products were not observed on HY. The intensity of FTIR absorption bands in the frequency range 1850-1250 cm-1, which resulted from adsorption of ethanoic acid on NaY, depended strongly on adsorbed molecule concentration and were time dependent. Spectra were simpler, and less intense at the same surface concentration on HY.

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Jeffery,Satchell

, p. 1876 (1962)

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Anderson

, p. 2371 (1952)

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Bawn,Williamson

, p. 721,732 (1951)

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FORMATION OF ACETIC ANHYDRIDE BY CARBONYLATION OF METHYL ACETATE

Mamyan, V. A.,Sominskii, S. D.,Pirozhkov, S. D.,Barsegyan, V. L.,Vardanyan, V. D.,Lapidus, A. L.

, p. 2095 - 2098 (1985)

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ELECTROPHILIC ADDITION REACTIONS TO PHENYLACETYLENE CATALYZED BY HETEROPOLY ACID

Matsuo, Kazuhiro,Urabe, Kazuo,Izumi, Yusuke

, p. 1315 - 1316 (1981)

Heteropoly acid efficiently catalyzed the addition reactions of water and carboxylic acid to phenylacetylene to form acetophenone at 60 deg C in the liquid phase.The higher catalytic activity of heteropoly acid compared with H2SO4 and HClO4 is due to the cooperative action of heteropoly anion.

Mass Spectra and Pyrolyses of Some Vinylene Carbonates

Breitbeil, Fred W.,Skrobot, Angeline A.

, p. 702 - 704 (1982)

The mass spectra of a series of 1,3-dioxol-2-ones were examined for evidence of oxirenes in the fragmentation process.The M-cation radical-CO2 (oxirene or isomers) fragment was observed in six of eight samples.Four major pathways explain the mass spectra: M-cation radical-CO2-CO, M-cation radical-C2O3, M-cation radical-C2O2R and M-cation radical-CO-CO2.Metastable peaks support this.Similar pathways on pyrolysis were sought and observed.At 800 deg C and pressure of 1.5-4 mm, 1,3-dioxol-2-ones 1-3 and 5-7 were pyrolyzed in a stream of helium.The major products were, respectively, ketene (R1=R2=H), propene (R1=R2=CH3), fluorene (R1=R2=C6H5), ethene (R1=H, R2=CH3), stilbene (R1=H, R2=C6H5), and styrene (R1=CH3, R2=C6H5).Apparently the 1,3-dioxol-2-ones lose CO2 and CO successively to produce a carbene which either rearranges or dimerizes.

Kachler, J.

, (1891)

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Fleming,Philippides

, p. 2426 (1970)

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Denham, W. S.

, p. 1235 - 1240 (1909)

Ctc-[Pt(NH3)2(cinnamate)(valproate)Cl2] is a highly potent and low-toxic triple action anticancer prodrug

Li, Yang,Shi, Shan,Zhang, Shurong,Gan, Zongjie,Wang, Xin,Zhao, Xudong,Zhu, Yijian,Cao, Meiting,Wang, Xiaoyue,Li, Wei

, p. 11180 - 11188 (2021)

Pt(iv) prodrugs have gained tremendous attention due to their indisputable advantages compared to cisplatin. Herein, new Pt(iv) derivatives with cinnamic acid at the first axial position, and inhibitor of matrix metalloproteinases-2 and-9, histone deacetylase, cyclooxygenase or pyruvate dehydrogenase at the second axial position are constructed to develop multi-action prodrugs. We demonstrate that Pt(iv) prodrugs are reducible and have superior antiproliferative activity with IC50 values at submicromolar concentrations. Notably, Pt(iv) prodrugs exhibit highly potent anti-tumour activity in an in vivo breast cancer model. Our results support the view that a triple-action Pt(iv) prodrug acts via a synergistic mechanism, which involves the effects of CDDP and the effects of axial moieties, thus jointly leading to the death of tumour cells. These findings provide a practical strategy for the rational design of more effective Pt(iv) prodrugs to efficiently kill tumour cells by enhancing their cellular accumulation and tuning their canonical mechanism.

SYNTHESIS OF ACETIC ANHYDRIDE BY VAPOR PHASE CARBONYLATION OF METHYL ACETATE WITH A NICKEL-ACTIVE CARBON CATALYST

Fujimoto, Kaoru,Shikada, Tsutomu,Miyauchi, Michiharu,Tominaga, Hiro-o

, p. 1157 - 1160 (1983)

Vapor phase carbonylation of methyl acetate on nickel-active carbon catalyst was studied under pressurized conditions in the presence of methyl iodide as a promoter.High pressure was essential for the acetic anhydride formation.A fairly large amount of acetic acid, by-product, was also formed under the water-free reaction condition.

Stromnova, T. A.,Vargaftik, M. N.,Moiseev, I. I.

, (1983)

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Doumaux et al.

, p. 3992 (1969)

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87. Novel aplysinopsin-type alkaloids from scleractinian corals of the family Dendrophylliidae of the Mediterranean and the Philippines. Configurational-assignment criteria, stereospecific synthesis, and photoisomerization

Guella,Mancini,Zibrowius,Pietra

, p. 773 - 782 (1988)

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Carbonylation of methyl acetate in the presence of rhodium catalysts based on pyrrolidinopyridine polymers

Terekkova,Kolesnichenko,Batov,Alieva,Trukhmanova,Slivinskii,Pesin,Plate

, p. 818 - 819 (1999)

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Dicarboxylic Acids Link Proton Transfer Across a Liquid Membrane to the Synthesis of Acyl Phosphates. A Model for P-Type H(+)-ATPases

Colton, Ian J.,Kazlauskas, Romas J.

, p. 3626 - 3635 (1994)

H(+)-ATPases are ion pumps that link proton transfer across cell membranes to the synthesis or hydrolysis of ATP.A current research goal is to understand the molecular-level mechanism of this linking.We present a chemical model that mimics some features of H(+)-ATPases by linking proton transfer across a liquid membrane to the synthesis of acyl phosphates using carboxylic acid anhydride intermediates.Citraconic acid (cis-2-methyl-2-butenedioic acid) accelerated the transfer of protons from a pH 0.3 solution across a chloroform liquid membrane to a pH 10 solution.The mechanism involved spontaneous formation of a small amount of citraconic anhydride (0.6percent) in the pH 0.3 layer.This anhydride partitioned into the chloroform layer and diffused to the pH 10 layer, where it hydrolyzed, generating two protons.When the pH 10 layer contained phosphate (1.0 M), some of the citraconic anhydride reacted with phosphate to form citraconyl phosphate, 5.0percent yield.In separate experiments, we confirmed that citraconyl phosphate had high phosphoryl donor potential by reacting it with morpholine to form a phosphoramidate (11.5percent yield) or with fluoride to form fluorophosphonate (32percent yield).To demonstrate the link between an acyl phosphate and a proton gradient in the reverse direction, we used succinyl phosphate, whose hydrolysis occurs in two steps: formation of succinic anhydride, which consumes protons, followed by hydrolysis of succinic anhydride, which releases protons.We generated a pH gradient by carrying out these two steps in separate solutions.Hydrolysis of succinyl phosphate (3.9 mmol) at pH 6.00 started with a increase in pH to 6.16 (0.59 mmol of H(+) consumed) caused by the formation of succinic anhydride.We extracted this anhydride with dichloromethane and transferred it to a separate solution at pH 6.05.Hydrolysis of the anhydride released protons (0.36 mmol), decreasing the pH to 5.23.Our model suggests that H(+)-ATPases could use acyl phosphates and carboxylic acid anhydride intermediates to link proton transfer to ATP synthesis or hydrolysis.

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Susuki et al.

, p. 2663 (1968)

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Electrophilic Substitution of Polycyclic Fluoranthene Hydrocarbons

Minabe, Masahiro,Cho, Bongsup P.,Harvey, Ronald G.

, p. 3809 - 3812 (1989)

The first systematic study of the sites of electrophilic substitution (acylation and/or bromination) of polycyclic fluoranthene hydrocarbons is described.The hydrocarbons studied include indenopyrene (1), benzaceanthrylene (2), benzacephenanthrylene (3), and indenochrysene (4).Compounds 1-4 all undergo bromination regioselectively in a single site.The latter are determined by conversion of the bromo derivatives to monodeuterio analogues by metal exchange with butyllithium and analysis of their high-resolution 1H and 13C NMR spectra in comparison with those of the parent hydrocarbons.This method is potentially generally applicable to determination of the sites of substitution of other complex polycyclic hydrocarbon ring systems.Acylation of 1 is shown to take place in the same site as bromination, i.e., the 12-position.For 2 and 4, substitution occurs in the 8- and 5-positions, respectively, in good agreement with theoretical prediction by the DEWAR-PI method based on the relative energies of the Wheland intermediates for substitution at various ring positions.However, for 1 and 3 the principal sites of bromination observed experimentally are the 12- and 1-positions, respectively, which do not accord with theoretical prediction of the 3,5- and 8-positions, respectively.In the latter cases, the observed sites of bromination are only slightly less favorable energetically than the theoretically calculated sites and are probably within the limit of accuracy of the calculations.

Diozonides from coozonolyses of suitable O-methyl oximes and ketones

Griesbaum, Karl,Liu, Xuejun,Dong, Yuxiang

, p. 5463 - 5470 (1997)

Ozonolyses of the O-methyl oximes of cyclic ketones 5a - c in the presence of 1,4-cyclohexanedione (6) and ozonolyses of the O-methylated dioxime 8 of 1,4-cyclohexanedione in the presence of cycloketones 7a - c afforded the corresponding diozonides 11. Ozonolysis of the O-methyl oxime of acetone gave diozonide 18 in the presence of 6 and diozonide 21 in the presence of butanedione. Ozonolysis of the O-methyl oxime of cyclohexanone in the presence of butanedione gave diozonide 22. In addition, representatives of the hitherto unknown types of dispiro ozonides 12 having a lactam ring system have been obtained from the ozonolyses of 8 and 7.

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Kirshenbaum et al.

, p. 3141,3143 (1953)

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Detection of Elusive Chloro- and Bromo Substituted Ozonides by Nucleophilic Substitution Reactions

Griesbaum, Karl,Schlindwein, Konrad,Bettinger, Herbert

, p. 307 - 310 (1996)

Ozonolyses of 2,3-dichloro-2-butene (4), 4,5-dichloro-4-octene (9) and 2,3-dibromo-1,4-dichloro-2-butene (12) on polyethylene gave the corresponding ozonides 5,10 and 13a, respectively, which could not be isolated or unequivocally identified. Their identity could be proven, however, via substitution of the chloro- or bromo substituents at the ozonide rings by stabilizing substituents and subsequent isolation of the substituted ozonides 6, 11, 13b and 13c. Ozonolysis of 2,3-diacetoxy-2-butene (14) on polyethylene, in dichloro methane and in pentane gave mixtures of 16 and 17 but not ozonide 6.

Linear-reactor-infrared-matrix and Microwave Spectroscopy of the cis-2-Butene Gas-phase Ozonolysis

Kuehne, Heinz,Forster, Martin,Hulliger, Juerg,Ruprecht, Heidi,Bauder, Alfred,Guenthard, Hans-Heinrich

, p. 1971 - 1999 (1980)

Investigation of the formation of complex products in the gas-phase ozonolysis of cis-2-butene by linear-reactor-infrared-matrix and linear-reactor-microwave spectroscopy is reported.The following species have been unequivocally detected: secondary 2-butene ozonide, acetic acid, peracetic acid, glycolaldehyde, dimethyl ketene, the simple mixed anhydrides of formic and acetic acid, 2,3-epoxy-butane and 2-butanone, besides polyatomic products alredy known.In contrast, the primery ozonide has been detectable neither by LR.-MW. nor by LR.-IR.Observation of both stereoisomeric epoxides and kinetic modelling are used to support the intermediate formation of the O'Neal-Blumstein radical CH3CH(O2)CH(O)CH3 and the existence of a reaction channel in which the two carbon atoms of the C,C double bond of the olefin remain connected.As the dominant reaction path a mechanism with a Criegee type split into methyldioxirane (ethylidene peroxide) and acetaldehyde is considered and subsequently proposed to explain formation of many complex products by either unimolecular or bimolecular processes of the peroxide.For the reactions considered, thermochemical estimates of reaction enthalpies and activation data are included.Kinetic modelling for a partial reaction mechanism involving at least two different paths of decay of the O'Neal-Blumstein biradical into Criegee-type intermediates and the 2,3-epoxy-butanes is discussed.

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Edwards,Henley

, p. 3587 (1953)

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Oxidation of ethyl ether on borate glass: Chemiluminescence, mechanism, and development of a sensitive gas sensor

Hu, Jing,Xu, Kailai,Jia, Yunzhen,Lv, Yi,Li, Yubao,Hou, Xiandeng

, p. 7964 - 7969 (2008)

A gas sensor was developed by using the chemiluminescence (CL) emission from the oxidation of ethyl ether by oxygen in the air on the surface of borate glass. Theoretical calculation, together with experimental investigation, revealed the main CL reactions: ethyl ether is first oxidized to acetaldehyde and then to acetic acid, during which main luminous intermediates such as CH3CO? are generated and emit light with a peak at 493 nm. At a reaction temperature of 245°C, the overall maximal emission was found at around 460 nm, and the linear range of the CL intensity versus the concentration of ethyl ether was 0.12-51.7 μg mL-1 (R = 0.999, n = 7) with a limit of detection (3σ) of 0.04 μg mL-1. Interference from foreign substances including alcohol (methanol, ethanol and isopropanol), acetone, ethyl acetate, n-hexane, cyclohexane, dichloromethane, or ether (n-butyl ether, tetrahydrofuran, propylene oxide, isopropyl ether and methyl tert-butyl ether) was not significant except a minimal signal from n-butyl ether (a simple, sensitive and selective gas sensor for the determination of trace ethyl ether.

Bell,Lukianenko

, p. 1686 (1957)

Atmospheric chemistry of two biodiesel model compounds: Methyl propionate and ethyl acetate

Andersen, Vibeke F.,Berhanu, Tesfaye A.,Nilsson, Elna J. K.,Jorgensen, Solvejg,Nielsen, Ole John,Wallington, Timothy J.,Johnson, Matthew S.

, p. 8906 - 8919 (2011)

The atmospheric chemistry of two C4H8O2 isomers (methyl propionate and ethyl acetate) was investigated. With relative rate techniques in 980 mbar of air at 293 K the following rate constants were determined: k(C2H5C(O)OCH3 + Cl) = (1.57 ± 0.23) × 10-11, k(C2H5C(O) OCH3 + OH) = (9.25 ± 1.27) × 10-13, k(CH 3C(O)OC2H5 + Cl) = (1.76 ± 0.22) × 10-11, and k(CH3C(O)OC2H5 + OH) = (1.54 ± 0.22) × 10-12 cm3 molecule -1 s-1. The chlorine atom initiated oxidation of methyl propionate in 930 mbar of N2/O2 diluent (with, and without, NOx) gave methyl pyruvate, propionic acid, acetaldehyde, formic acid, and formaldehyde as products. In experiments conducted in N 2 diluent the formation of CH3CHClC(O)OCH3 and CH3CCl2C(O)OCH3 was observed. From the observed product yields we conclude that the branching ratios for reaction of chlorine atoms with the CH3-, -CH2-, and -OCH3 groups are 9 ± 2%, respectively. The chlorine atom initiated oxidation of ethyl acetate in N2/O 2 diluent gave acetic acid, acetic acid anhydride, acetic formic anhydride, formaldehyde, and, in the presence of NOx, PAN. From the yield of these products we conclude that at least 41 ± 6% of the reaction of chlorine atoms with ethyl acetate occurs at the -CH2- group. The rate constants and branching ratios for reactions of OH radicals with methyl propionate and ethyl acetate were investigated theoretically using transition state theory. The stationary points along the oxidation pathways were optimized at the CCSD(T)/cc-pVTZ//BHandHLYP/aug-cc-pVTZ level of theory. The reaction of OH radicals with ethyl acetate was computed to occur essentially exclusively (~99%) at the -CH2- group. In contrast, both methyl groups and the -CH2- group contribute appreciably in the reaction of OH with methyl propionate. Decomposition via the α-ester rearrangement (to give C2H5C(O)OH and a HCO radical) and reaction with O 2 (to give CH3CH2C(O)OC(O)H) are competing atmospheric fates of the alkoxy radical CH3CH2C(O)OCH 2O. Chemical activation of CH3CH2C(O)OCH 2O radicals formed in the reaction of the corresponding peroxy radical with NO favors the α-ester rearrangement.

Acyl iodides in organic synthesis: V. Reactions with carboxylic acid esters

Voronkov,Trukhina,Vlasova

, p. 357 - 359 (2004)

Acyl iodides react with alkyl, alkenyl, and aralkyl esters derived from saturated, unsaturated, and aromatic mono- and dicarboxylic acids in the absence of a catalyst. The reaction involves cleavage of the OR bond and formation of organic iodide RI (including CH2=CHI) and one or two symmetric carboxylic acid anhydrides. Phenyl acetate reacts with benzoyl iodide to give acetyl iodide and phenyl benzoate as a result of cleavage of the (O=)C-O bond. The reaction of diethyl fumarate with acetyl iodide is accompanied by cis- trans isomerization to afford maleic anhydride. In the reactions of acetyl iodide with diethyl oxalate and diethyl malonate, CO and CO2 and CO 2 and polyketene are formed, respectively, in addition to ethyl iodide and acetic anhydride. Ethyl esters of strong organic acids, e.g., ethyl trihaloacetates, failed to react with acyl iodides under analogous conditions.

Ozonolyses of acetylenes revisited

Griesbaum, Karl,Dong, Yuxiang

, p. 575 - 577 (1997)

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MECANISME DE CETONISATION DU PHENYLACETYLENE ACIDO-CATALYSEE PAR H2SO4, HSO3CH3 et BF3 (CH3COOH)2. MISE EN EVIDENCE DE L'INTERMEDIARE ACETOXYSTYRENE

Montheard, Jean-Pierre,Camps, Marcel,Benzaid, Ahmed

, p. 523 - 526 (1981)

Acetic acid reacts with phenylacetylene in acid catalysis to give an intermediate product: α-acetoxystyrene, which reacts fastly to give acetophenone.A kinetical study is shown.

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Karrer,Hohl

, p. 1933 (1949)

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PROCESS FOR GENERATING ACID ANHYDRIDES

-

Paragraph 0087-0088; 0089-0092, (2021/11/13)

Provided is a method of producing an anhydride of an organic mono-acid comprising contacting an organic mono-acid and a thermally regenerable anhydride to produce the anhydride of the organic mono-acid, and either a diacid of the regenerable anhydride, a partially hydrolyzed regenerable anhydride, or both. In a particular example, acetic acid and glutaric anhydride can be reacted to form acetic anhydride.

A transesterification-acetalization catalytic tandem process for the functionalization of glycerol: The pivotal role of isopropenyl acetate

Calmanti, Roberto,Perosa, Alvise,Rigo, Davide,Selva, Maurizio

supporting information, p. 5487 - 5496 (2020/09/23)

At 30 °C, in the presence of Amberlyst-15 as a catalyst, a tandem sequence was implemented by which a pool of innocuous reactants (isopropenyl acetate, acetic acid and acetone) allowed upgrading of glycerol through selective acetylation and acetalization processes. The study provided evidence for the occurrence of multiple concomitant reactions. Isopropenyl acetate acted as a transesterification agent to provide glyceryl esters, and it was concurrently subjected to an acidolysis reaction promoted by AcOH. Both these transformations co-generated acetone which converted glycerol into the corresponding acetals, while acidolysis sourced also acetic anhydride that acted as an acetylation reactant. However, tuning of conditions, mostly by changing the reactant molar ratio and optimizing the reaction time, was successful to steer the set of all reactions towards the synthesis of either a 1?:?1 mixture of acetal acetates (97% of which was solketal acetate) and triacetin, or acetal acetates in up to 91% yield, at complete conversion of glycerol. To the best of our knowledge, a one-pot protocol with such a degree of control on the functionalization of glycerol via transesterification and acetalization reactions has not been previously reported. The procedure was also easily reproduced on a gram scale, thereby proving its efficiency for preparative purposes. Finally, the design of experiments with isotopically labelled reagents, particularly d4-acetic acid and d6-acetone, helped to estimate the contribution of different reaction partners (iPAc/AcOH/acetone) to the formation of final products. This journal is

PHTHALAZINE DERIVATIVES, AND PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE THEREOF

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Paragraph 0194; 0261, (2018/11/21)

The present invention provides a compound of formula I, a cis-trans isomer, an enantiomer, a diastereoisomer, a racemate, a solvate, a hydrate, or a pharmaceutical acceptable salt and ester thereof, a preparation method for preparing the same, a pharmaceutical composition comprising the same and a use of the compound as an α5-GABAA receptor regulator, wherein T, Z, A and Y are as defined in the description.

Production of acetic anhydride

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Paragraph 0067-0069, (2017/06/27)

An object is to provide a method for producing a ketene derivative that decreases the consumption quantity of phosphorus compounds, and the discharge quantity of the phosphorus compounds into the environment. A method for producing a ketene derivative includes a step (i) of conducting thermal decomposition reaction of acetic acid in a presence of a phosphorus-containing catalyst in a reactor to produce a thermal decomposition gas containing ketene, a step (ii) of cooling the thermal decomposition gas to be separated into a gaseous component containing ketene, and a condensed liquid containing a phosphorus compound (a), and a step (iii) of causing the ketene to react with a different organic compound to produce a ketene derivative. The step (i) includes conducting the thermal decomposition reaction while supplying, into the reactor, the condensed liquid containing the phosphorus compound (a) or a concentrated liquid of the condensed liquid.

Process route upstream and downstream products

Process route

pyridine
110-86-1

pyridine

dibutyl chlorophosphite
4124-92-9

dibutyl chlorophosphite

acetic acid
64-19-7,77671-22-8

acetic acid

dibutyl hydrogen phosphite
1809-19-4

dibutyl hydrogen phosphite

acetic anhydride
108-24-7

acetic anhydride

Conditions
Conditions Yield
at -10 ℃;
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

aniline hydrochloride
142-04-1,36663-09-9

aniline hydrochloride

acetic anhydride
108-24-7

acetic anhydride

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
disilver(I) terephthalate
29327-92-2,53338-75-3

disilver(I) terephthalate

acetyl chloride
75-36-5

acetyl chloride

terephthalic acid
100-21-0

terephthalic acid

acetic anhydride
108-24-7

acetic anhydride

Conditions
Conditions Yield
acetic acid
64-19-7,77671-22-8

acetic acid

acetic anhydride
108-24-7

acetic anhydride

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With phosgene; benzylidene dichloride;
(Z)-2-Butene
590-18-1

(Z)-2-Butene

dimethylketene
598-26-5

dimethylketene

formic anhydride
1558-67-4

formic anhydride

acetic anhydride
108-24-7

acetic anhydride

butanone
78-93-3

butanone

2,3-cis-epoxybutane
925669-95-0

2,3-cis-epoxybutane

2,3-trans-epoxybutane
21490-63-1

2,3-trans-epoxybutane

Conditions
Conditions Yield
With ozone; Kinetics; Mechanism; gas-phase ozonolysis;
sodium nitrate
7631-99-4

sodium nitrate

acetyl chloride
75-36-5

acetyl chloride

sodium iodide dichloride
35703-63-0

sodium iodide dichloride

acetic anhydride
108-24-7

acetic anhydride

Nitrogen dioxide
10102-44-0

Nitrogen dioxide

Conditions
Conditions Yield
With iodine; In not given; 40 - 50°C; evapn.;
With I2; In not given; 40 - 50°C; evapn.;
N,N,N',N'-tetraacetylethylenediamine
10543-57-4

N,N,N',N'-tetraacetylethylenediamine

acetic acid
64-19-7,77671-22-8

acetic acid

N,Ν,Ν'-triacetylenediamine
137706-80-0

N,Ν,Ν'-triacetylenediamine

acetic anhydride
108-24-7

acetic anhydride

Conditions
Conditions Yield
at 140 ℃; Temperature; Kinetics;
bromoacetic anhydride
13094-51-4

bromoacetic anhydride

acetic anhydride
108-24-7

acetic anhydride

Conditions
Conditions Yield
With sodium acetate; Destillation des entstandenen gemischtes Anhydrids;
2-acetoxy-2-phenylacetic acid
29071-09-8

2-acetoxy-2-phenylacetic acid

benzylidene 1,1-diacetate
581-55-5

benzylidene 1,1-diacetate

acetic anhydride
108-24-7

acetic anhydride

benzaldehyde
100-52-7

benzaldehyde

acetic acid
64-19-7,77671-22-8

acetic acid

Conditions
Conditions Yield
With triethylamine; In acetonitrile; Ambient temperature; electrolysis;
49 % Turnov.
11 % Turnov.
With triethylamine; In acetonitrile; Mechanism; Product distribution; Ambient temperature; electrolysis;
49 % Turnov.
11 % Turnov.
benzylidene dichloride
98-87-3

benzylidene dichloride

acetic acid
64-19-7,77671-22-8

acetic acid

hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

acetic anhydride
108-24-7

acetic anhydride

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
Kinetics;

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