Ethan acid anhydride

The selective oxidation of C—H bonds in alkanes under mild conditions continues to attract interest from researchers. A new procedure based upon mild generation of perfluoroalkyl radicals from their corresponding anhydrides with either H2O2, m-CPBA, AIBN, or PbEt4 has been described. Oxidation of ethane under the reported conditions furnishes propionic acid and other fluorinated products.79 While some previously reported methods have involved metal-mediated functionalization of alkanes using trifluoroacetic acid/anhydride as solvent, these latter results indicate that the solvent itself without metal catalysis can react as an oxidant. As a consequence, results of these metal-mediated reactions should be treated with caution. The absolute rate constants for H-abstraction from BU3 SnH by perfluorinated w-alkyl radicals have been measured and the trends were found to be qualitatively similar to that of their addition reactions to alkenes.80 a,a-Difluorinated radicals were found to have enhanced reactivities and this was explained as being due to their pyramidal nature while multifluorinated radicals were more reactive still, owing to their electrophilic nature.80... 

Studies of the polymerisation of alanine A-carboxylic acid anhydride with diethylzinc or triisobutylaluminium as the catalyst have revealed the relatively fast deprotonation of the monomer NH group by the metal alkyl as the first reaction step. This reaction (easily detectable by evolution of the ethane or isobutane) produces A-metallated initiating species (substituted metal carbamates) which, however, are not monomeric but undergo association via metal-heteroatom coordination bonds [75,175]. 

Interestingly, unlike ethane, neither methane nor propane is able to participate in this reaction sequence, the former because the C-H bond of methane is too strong to undergo significant hydrogen-atom abstraction by the Rf. radical and the latter because only primary alkyl radicals are sufficiently reactive to attack (R C0)20. Thus, Sen s observation of Pd(II)-catalyzed conversion of methane to methanol derivative by H202 in trifluoroacetic acid/anhydride mixture was not complicated by the above reaction [26,29]. 

Its chief importance is as a source of cinnamic acid by condensation with sodium ethan-oate and ethanoic anhydride and as a source of triphenylmethane dyestuffs by condensation with pyrogallol, dimethylaniline, etc. It is also used in the manufacture of perfumes. 

Butane is primarily used as a fuel gas within the LPG mixture. Like ethane and propane, the main chemical use of butane is as feedstock for steam cracking units for olefin production. Dehydrogenation of n-butane to butenes and to butadiene is an important route for the production of synthetic rubber. n-Butane is also a starting material for acetic acid and maleic anhydride production (Chapter 6). 

Aminotrimethanephosphonic acid is formed from formamide, acetamide, urea, or alkanenitriles with phosphorous acid [296]. By reaction of monoalkyl phosphite or P406 with glacial acetic acid or the corresponding anhydride ethane-1 -hydroxy-1,1-diphosphonic acid is formed after hydrolysis [297,298]. P406 can be obtained from P4 and 02 in a high yield of 85-90% [299]. 

There are many methods for the preparation of ethane-1-hydroxy-1,1-diphosphonic acid including reacting phosphorus trichloride and acetic acid in the presence of tributylamine [106], phosphorus with acetic acid and oxygen [108], acetic anhydride with phosphorous acid and acetyl chloride [80,84-86,109,110], and acetic anhydride with phosphoric acid and acetic acid [111]. By another method ketene and phosphorous acid can be used [112], as shown in Eq. (68) ... 

The diacetylated ethane-1-hydrox-1,1-diphosphonic acid is prepared by dissolving the diphosphonic acid in acetic acid and adding acetic anhydride [114]. The sodium salt can be directly converted to the free acid form by passing it through an hydrogen cation exchanger. The bicyclic dimer is prepared by basic hydrolysis of diacetylated cyclic dimer, as shown in Eq. (70) ... 

Figure 12.12 THM GC/MS curves of a Winsor Newton lemon alkyd paint (a) and of an alkyd sample taken from Fontana s work Concetto spaziale (1961) (b). Peak assignments 1, 1,3 dimethoxy 2 propanol 2, 1,2,3 trimethoxy propane 3, 3 methoxy 1,2 propandiol 4, 4 chloro benzenamine 5, 3 methoxy 2,2 bis(methoxymethyl) 1 propanol 6, 3 chloro N methyl benzenamine 7, 3 methoxy 2 methoxymethyl 1 propanol 8, 4 chloro N methyl benzenamine 9, phthalic anhydride 10, 3 chloro 4 methoxy benzenamine 11, suberic acid dimethyl ester 12, dimethyl phthalate 13, azelaic acid dimethyl ester 14, sebacic acid dimethyl ester 15, palmitic acid methyl ester 16, oleic acid methyl ester 17, stearic acid methyl ester 18, 12 hydroxy stearic acid methyl ester 19, 12 methoxy stearic acid methyl ester 20, styrene 21, 2 (2 methoxyethoxy) ethanol 22, 1,1 oxybis(2 methoxy ethane) 23, benzoic acid methyl ester 24, adipic acid dimethyl ester 25, hexadecenoic acid methyl ester 26, dihydroisopimaric acid methyl ester 27, dehydroabietic acid methyl ester 28, 4 epidehydroabietol...

The anhydride of ethane- 1,2-disulfinic acid has structure [31b] (Mueller and Dines, 1969). In this instance the strain associated with the four-membered ring in [31a], which is absent in the five-membered sulfinic anhydride, is sufficient to ... 

Ethanal is only used as an intermediate to acetic acid and its derivatives and in the near future production of ethanal will be replaced by other routes based on methanol and syn-gas to give acetic acid and acetic anhydride. Vinyl acetate can also be made via syn-gas routes, but the major producer in Europe employs a direct Wacker route with a heterogeneous palladium catalyst (former Hoechst ethene, acetic acid -from syn-gas-, and oxygen). 

In a similar manner to the preparation of 1,3,2-dioxathiolane 2-oxide from 1,2-dihydroxyethane and thionyl chloride, 1,2,3-oxadithiolane 2-oxide was prepared from 2-mercaptoethanol and thionyl choride <75ACS(A)414>. 1,2,5-Oxadithiolane 2,5-dioxide (66), the cyclic anhydride of ethane-1,2-disulfinic acid, was obtained by controlled hydrolysis of ethanebis(disulfinyl) chloride <76CRV747>. The corresponding 2,2,5,5-tetroxide (67) was obtained by treatment of ethane-1,2-disulfonic acid with thionyl chloride <(66HC(2l-i)l>. 

Ethane-tetracarboxylic Acid Dianhydride, [3,7-Dioxa-2,4,6,8 tetra-oxo-bicyclo(3,3,0)-octane], mw 170.1, OB to COg —66%, cryst, dec over 150°. It was first prepd in 1920 by heating the acid in a six-fold excess of acetic anhydride at 70—75°, then in 1923 by treating the acid with AcCl and heat, or by treating with oxalyl chloride, the acid or the tetra-silver salt of the acid (Ref 6)... 

Added CO2 allows the synthesis of substituted maleic anhydrides. According to a novel aminomethylation, ethane or propane is reacted with /V./V-di alkyl methyl-amine A-oxides in the presence of trifluoroacetic acid and a catalytic amount of Cu(OAc)2 to afford A,A-dialkylaminomethylated alkanes in good yields 321 337 338... 

NMO NMP Nu PPA PCC PDC phen Phth PPE PPTS Red-Al SEM Sia2BH TAS TBAF TBDMS TBDMS-C1 TBHP TCE TCNE TES Tf TFA TFAA THF THP TIPBS-C1 TIPS-C1 TMEDA TMS TMS-C1 TMS-CN Tol TosMIC TPP Tr Ts TTFA TTN N-methylmorpholine N-oxide jV-methyl-2-pyrrolidone nucleophile polyphosphoric acid pyridinium chlorochromate pyridinium dichromate 1,10-phenanthroline phthaloyl polyphosphate ester pyridinium p-toluenesulfonate sodium bis(methoxyethoxy)aluminum dihydride (3-trimethylsilylethoxy methyl disiamylborane tris(diethylamino)sulfonium tetra-n-butylammonium fluoride f-butyldimethylsilyl f-butyldimethylsilyl chloride f-butyl hydroperoxide 2,2,2-trichloroethanol tetracyanoethylene triethylsilyl triflyl (trifluoromethanesulfonyl) trifluoroacetic acid trifluoroacetic anhydride tetrahydrofuran tetrahydropyranyl 2,4,6-triisopropylbenzenesulfonyl chloride 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane tetramethylethylenediamine [ 1,2-bis(dimethylamino)ethane] trimethylsilyl trimethylsilyl chloride trimethylsilyl cyanide tolyl tosylmethyl isocyanide meso-tetraphenylporphyrin trityl (triphenylmethyl) tosyl (p-toluenesulfonyl) thallium trifluoroacetate thallium(III) nitrate... 

Ethanal. See Acetaldehyde A14-L Ethanaloxime. See Acetaldoxime A16-L Ethanamide. See Acetamide A16-R Ethaneamidine or Ethenylamidine. See u-Amino-o-imidoethane A223-L Ethanoic Acid. See Acetic Acid A25-L Ethanoic Anhydride. See Acetic Anhydride A29-R... 

The synthesis of intermediates and monomers from alkanes by means of oxidative processes, in part replacing alkenes and aromatics as the traditional building blocks for the chemical industry [2]. Besides the well-known oxidation of n-butane to maleic anhydride, examples of processes implemented at the industrial level are (i) the direct oxidation of ethane to acetic acid, developed by Sabic (ii) the ammoxidation of propane to acrylonitrile, developed by INEOS (former BP) and by Mitsubishi, and recently announced by Asahi to soon become commercial (iii) the partial oxidation of methane to syngas (a demonstration unit is being built by ENI). Many other reactions are currently being investigated, for example, (i) the... 

Synonyms ethanal, acetic aldehyde Formula CH3CHO MW 44.05 CAS [75-07-0] used in the production of acetic acid, acetic anhydride, and many synthetic derivatives found in water stored in plastic containers colorless mobil liquid fruity odor when diluted boils at 20.8°C solidifies at -121°C highly volatile vapor pressure 740 torr at 20°C density 0.78 g/mL at 20°C soluble in water, alcohol, acetone, ether, and benzene highly flammable... 

T ransparent heat resistant coatings were formed by heating of a mixture of BPA/DC, l,l,l-tris(4-cyanatophenyl)ethane, nonylphenol and Zn naphthenate [21]. The cross-linked polymer from BPA/DC, maleic anhydride, p-toluenesulfonic acid, Zn acetate and DABCO has high Tg [22]. BPA/DC monomer can be replaced by the corresponding prepolymer with p-toluenesulfonic acid monohydrate and Zn acetate. The composition obtained is processed as a molding compound [23],... 

Being the cyclic anhydride of ethane-1,2-disulfinic acid, 1,2,5-oxadithiolane 2,5-dioxide (99) hydrolyzed to the parent acid in an almost quantitative fashion on boiling for 1 minute in water (76CRV747). In an analogous manner, 1,2,5-oxadithiolane 2,2,5,5-tetroxide (100) and its benzo-, naphtho- and thieno-fused derivatives were hydrolyzed by water or, more rapidly, by hot alkali to the corresponding 1,2-disulfonic acids or their salts, respectively (66HC(21-l)l). 

An impartial decision has not yet been given as to whether the ethane production depends upon a direct union of the anions or upon the oxidation of an intermediate product, like acetic acid, acetic anhydride, or acetyl superoxide. 

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