Maleic acid Phenol

Benzoquinone Chemical species Chemical species Maleic acid Phenol... 

Mild acid converts it to the product and ethanol. With the higher temperatures required of the cyano compound [1003-52-7] (15), the intermediate cycloadduct is converted direcdy to the product by elimination of waste hydrogen cyanide. Often the reactions are mn with neat Hquid reagents having an excess of alkene as solvent. Polar solvents such as sulfolane and /V-m ethyl -pyrrol i don e are claimed to be superior for reactions of the ethoxy compound with butenediol (53). Organic acids, phenols, maleic acid derivatives, and inorganic bases are suggested as catalysts (51,52,54,59,61,62) (Fig. 6). 

The methylated maleic acid adduct of phthalic anhydride, known as methyl nadic anhydride VI, is somewhat more useful. Heat distortion temperatures as high as 202°C have been quoted whilst cured systems, with bis-phenol epoxides, have very good heat stability as measured by weight loss over a period of time at elevated temperatures. The other advantage of this hardener is that it is a liquid easily incorporated into the resin. About 80 phr are used but curing cycles are rather long. A typical schedule is 16 hours at 120°C and 1 hour at 180°C. 

Aliphatic acids (fumaric acid, maleic acid) are rapidly oxidized at the Sn02 anode, whereas they are practically electrochemically inactive at the Pt anode. The process at the Sn02 is able to completely oxidize phenol, which is quite unique for a low temperature process. 

Most industrially desirahle oxidation processes target products of partial, not total oxidation. Well-investigated examples are the oxidation of propane or propene to acrolein, hutane to maleic acid anhydride, benzene to phenol, or the ammoxidation of propene to acrylonitrile. The mechanism of many reactions of this type is adequately described in terms of the Mars and van Krevelen modeE A molecule is chemisorbed at the surface of the oxide and reacts with one or more oxygen ions, lowering the electrochemical oxidation state of the metal ions in the process. After desorption of the product, the oxide reacts with O2, re-oxidizing the metal ions to their original oxidation state. The selectivity of the process is determined by the relative chances of... 

Uses Manufacture of ethylbenzene (preparation of styrene monomer), dodecylbenzene (for detergents), cyclohexane (for nylon), nitrobenzene, aniline, maleic anhydride, biphenyl, benzene hexachloride, benzene sulfonic acid, phenol, dichlorobenzenes, insecticides, pesticides, fumigants, explosives, aviation fuel, flavors, perfume, medicine, dyes, and many other organic chemicals paints, coatings, plastics and resins food processing photographic chemicals nylon intermediates paint removers rubber cement antiknock gasoline solvent for fats, waxes, resins, inks, oils, paints, plastics, and rubber. 

Ozonization of phenol in water resulted in the formation of many oxidation products. The identified products in the order of degradation are catechol, hydroquinone, o-quinone, cis,ds-muconic acid, maleic (or fumaric) and oxalic acids (Eisenhauer, 1968). In addition, glyoxylic, formic, and acetic acids also were reported as ozonization products prior to oxidation to carbon dioxide (Kuo et al, 1977). Ozonation of an aqueous solution of phenol subjected to UV light (120-W low pressure mercury lamp) gave glyoxal, glyoxylic, oxalic, and formic acids as major products. Minor products included catechol, hydroquinone, muconic, fumaric, and maleic acids (Takahashi, 1990). Wet oxidation of phenol at 320 °C yielded formic and acetic acids (Randall and Knopp, 1980). 

Eevulinic acid, see Aniline Malaoxon, see Malathion Malathion diacid, see Malathion Malathion dicarboxylic acid, see Malathion Malathion monoacid, see Malathion Malathion a-monoacid, see Malathion Malathion p-monoacid, see Malathion 2-Nitrophenol p-Malathion monoacid, see Malathion Malathion monocarboxylic acid, see Malathion Maleic acid, see 2-Chlorophenol, Maleic anhydride. Maleic hvdrazide. 4-Nitrophenol, Phenol Malonic acid, see Cyclohexene, 1,4-Dioxane Malonic acid semialdehyde, see irans-1,3-Dichloropropylene... 

Both fumaric and maleic acid give rise to coumarins on reaction with phenols. Initially, this route was considered different from the Pechmann reaction, but experimental evidence has been accumulated which suggests that it is simply a variant (73AJC899). Under the acidic conditions, the unsaturated acid could well produce some malic acid, which would then lose carbon monoxide and water as usual. Generally yields in the two approaches to coumarins are much the same. 

Catalytic oxidation is the most important technology for the conversion of hydrocarbon feedstocks (olefins, aromatics and alkanes) to a variety of bulk industrial chemicals.1 In general, two types of processes are used heterogeneous, gas phase oxidation and homogeneous liquid phase oxidation. The former tend to involve supported metal or metal oxide catalysts e.g. in tne manufacture of ethylene oxide, acrylonitrile and maleic anhydride whilst the latter generally employ dissolved metal salts, e.g. in the production of terephthalic acid, benzoic acid, acetic acid, phenol and propylene oxide. 

Maleic acid is a linear four-carbon molecule with carboxylate groups on either end, similar to succinic acid, but with a double bond between the central carbon atoms. The anhydride of maleic acid is a cyclic molecule containing five atoms in its ring. Although the reactivity of maleic anhydride is similar other such reagents like succinic anhydride, the products of maleylation are much more unstable toward hydrolysis, and the site of unsaturation lends itself to additional side reactions. Acylation products of amino groups with maleic anhydride are stable at neutral pH and above, but they readily hydrolyze at acid pH values (around pH 3.5) (Butler etal., 1967). Maleylation of sulfhydryls and the phenolate of tyrosine are even more sensitive to hydrolysis. 

Assuming that these are the only products (plus water), and that the initial number of moles of phenol is nPh, write the mass balance that describes at any time the change in number of moles of phenol, (nPh - Ph) as a function of the number of moles of benzoquinone (nBQ), maleic acid ( MA) and carbon dioxide (nco) produced up to that moment as follows ... 

The following substances are recommended starting materials for unsaturated polyesters fumaric acid, maleic acid, methacrylic acid, adipic acid, phthalic acid, resi-nic acid, isophthalic acid, terephthalic acid, hydrated or halogenated phthalic acids, aliphatic and substituted aliphatic single and multi-functional alcohols up to C)8, alkoxylated and hydrated phenols and bisphenols, styrene, vinyltoluene, acrylic acid and methacrylic acid esters of the Ci-C4 alcohols, and tricyclodecane dimethanol. 

Poly(vinyl alcohol) is utilized as a component of starch-based adhesives.11121114 Other patents report the use of partially oxidized starch,1115 dextrins,1116 dextrins and urea,1117 borax,1118 boric acid,1119 and vinyl methyl ether-maleic acid copolymers.1120 Other patents indicate the use of poly (vinyl alcohol) with partially hydrolyzed poly(vinyl acetate),1121 nonhy-drolyzed poly(vinyl acetate),1122 and poly(vinyl chloride).1123 A few patents have reported such poly acrylic additives as poly (acrylic acid)1124 and its salts,1125 poly(acrylamide),1126 1127 A-methylacrylamide or poly(A-acryl-amide),1128 and polyethyleneimine.1129 Polystyrene has also been used,1130 as well as more complex copolymers such as a maleic acid monobutyl ester-methyl vinyl ether copolymer, together with dextrin and polyacrylamide),1131 carboxylated ethyl acrylate-styrene zinc salt copolymer,1132 ethylene-methyl acrylate-vinyl acetate copolymer,1133 vinyl acetate-vinyl pyr-rolidone copolymer,1134 and ethylene-vinyl acetate copolymer.1135 Some adhesives are compounded with SBR latex1136 1138 and phenol-formaldehyde resins.1139... 

Figure 2 Creep-recovery tests of chemically treated woods. U, untreated wood Fs, vapor phase formalization F, liquid phase formalization A, acetylation PO, etherification with propylene oxide MG, treatment with maleic acid and glycerol PFl, impregnation with low molecular weight phenol-formaldehyde resin PEG-ICP, impregnation with polyethylene glycol (PEG-IOOO) WPC, formation of a wood- polymer composite (PMMA) WIC, formation of a wood-inorganic material composite.

Additionally to phenolic intermediates, upon the aromatic ring opening, a series of carboxylic acids can be formed. Maleic acid, for instance, has been detected in the oxidation of byphenyls (Bouquet-Somrani et al., 1996), 1,2,4-THB (Li et al., 1991a), 1,2-dimethoxybenzene (Pichat, 1997), and acid orange 7 (Stylidi et al., 2003). Similarly, muconic acid has been reported as an intermediate of byphenyls oxidation (Bouquet-Sormani et al., 1996), while succinic and malonic acids were identified in polycarboxylic benzoic acid oxidation (Assabane et al., 2000). It is therefore expected that these or similar acids be formed during phenol oxidation. 

The oxidation of phenol on a platinum anode was studied by the same author [34]. At a current density of 50mA/cm, 70°C, and a pH of 3, the initial phenol concentration of 21 mmol/dm completely disappeared in 2 h. Apart from CO2, other organic intermediates such as hydroquinone, benzoquinone, maleic acid, fumaric acid, and oxalic acid were identified. An analysis of the reaction intermediates and a carbon balance showed that the destruction reaction occurred by two parallel pathways chemical oxidation with electrogenerated hydroxyl radicals, and direct oxidation of phenol and/or its aromatic intermediates to CO2. 

Organotin derivatives of maleic acid may have an additional stabilizer function with the Diels-Alder reaction (Figure 3.3.3) by scavenging function. Their performance is good in all types of vinyl chloride polymerization, i.e. suspension, emulsion, and bulk. Optimum results are obtained when they are combined with small amounts of phenolic antioxidants particularly in plasticized PVC, impact-modified PVC, and PVC copolymers. 

Alkyl phenol ethoxylates can also react with P4O10 yielding alkyl phenol etherphosphates as a mixture of mono-/diesters or with maleic anhydride to yield maleic acid monoesters, which then react with NaHS03 to yield sulphosuccinate monoesters. Alkylphenolpolyglycolether sulphates, phosphates or sulphosuccinates are mainly used as primary anionic emulsifiers for the manufacturing of acrylic, styrene/acrylic or vinyl acetate co-polymer dispersions. Another type of non-ionic emulsifier is block copolymers of ethylene oxide with propylene oxide. 

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