Alkenylsuccinic anhydride

Alkenylsuccinic anhydrides made from several linear alpha olefins are used in paper sizing, detergents, and other uses. Sulfosuccinic acid esters serve as surface active agents. Alkyd resins (qv) are used as surface coatings. Chlorendric anhydride [115-27-5] is used as a flame resistant component (see Flame retardants). Tetrahydrophthalic acid [88-98-2] and hexahydrophthalic anhydride [85-42-7] have specialty resin appHcations. Gas barrier films made by grafting maleic anhydride to polypropylene [25085-53-4] film are used in food packaging (qv). Poly(maleic anhydride) [24937-72-2] is used as a scale preventer and corrosion inhibitor (see Corrosion and corrosion control). Maleic anhydride forms copolymers with ethylene glycol methyl vinyl ethers which are partially esterified for biomedical and pharmaceutical uses (189) (see Pharmaceuticals). 

Other Uses. A small but growing oudet for C and higher linear olefins is the production of alkenylsuccinic anhydride (ASA) for the paper iadustry. ASA is an effective alkaline sizing agent and competes with alkylketene dimer (AKD) ia this appHcatioa. 

Internal Sizing. The most widely used internal sizes are alkyl ketene dimers (AKD), alkenylsuccinic anhydrides (ASA), and rosin-based sizes that are used with papermaker s alum (aluminum sulfate with 14 waters of hydration), polyaluminum chloride (PAG), or polyaluminum siUcosulfate (PAS) (61). The rosin-based sizes are used under acidic conditions. Since the mid 1980 s there has been a steady conversion from acid to alkaline paper production, resulting in static to declining demand for the rosin-based sizing systems. Rosin is a complex mixture of compounds and consists primarily of monocarboxyhc acids with alkylated hydrophenan threne stmctures (62). A main constituent of wood rosin, gum rosin and taH-oil rosin is abietic acid. 

Alkenylbenzene by-products, 23 335 Alkenylborates, 13 653 Alkenyl coupling, 13 653 Alkenyl halides, 12 167 Alkenylpyridine derivatives, physical properties of, 21 94t Alkenylsuccinic anhydride (ASA),... 

See also Alkenylsuccinic anhydrides production of, 17 726 Alkenylsuccinic anhydrides, 15 490 Alkoxidation, higher aliphatic alcohols, 2 5 Alkoxide catalysts, 10 683 Alkoxide-derived silica gels, structure of, 23 73... 

A particular type of cellulose esters are those formed with paper sizing agents such as alkylketene dimers (AKD) or alkenylsuccinic anhydride (ASA) [47], The reaction of cellulose with alkylketene dimers generates p-ketoesters ... 

Esterification with poly(carboxylic anhydrides) can be controlled to minimize diesterification and crosslinking to produce carboxylated cellulosic esters. Eastman Kodak in a recent patent claimed the succinylation of cellulose to different degrees 1 per 3 anhydroglucose rings [182] and 1 per 2 rings [183]. Henkel [184] also has a patent for a surfactant by the esterification of cellulose with alkenylsuccinic anhydride, presumably substitution degree governs the hydrophile-hydrophobe balance of the product and its surfactant properties. 

Lube oil additives have increased in importance since better engine performances are required to meet air pollution standards and increased fuel efficiency. End reaction products of MA with olefins, e.g., polyisobutylenesuc-cinic anhydride, other alkenylsuccinic anhydrides, etc. are used as viscosity index improvers and also as ashless dispersants in the fuels. (See Chapter 5.)... 

Generality of the reaction has been well documented. Some of the works leading to various alkenylsuccinic anhydrides (ASA) have been summarized (Table 5.1). It appears that yields improve to some extent with internal and 2-alkyl-1-olefins. This has been taken advantage of in a number of commercial products, where mixtures of olefins such as polyisobutylene oligomers and olefins produced from cracked hydrocarbon have been reacted with MA. Unusual properties of these type of products are thus made reasonably available. The reactivities for the open-chain olefins are ... 

Suzuki has reported that the olefin function of the alkenylsuccinic anhydride 76 can be rearranged in the presence of a palladium catalyst and a soluble base, such as trialkylamine or dialkylaniline, to give alkylmaleic anhydride 77. Better than 40% conversion was obtained. Ruthenium catalysts... 

In addition, the alkenylsuccinic anhydrides may be converted to esters, amides, imides, etc., and each is capable of modification for a suitable application.Such materials have been suggested as, for example, ashless synthetic lubricants and corrosion inhibitors. 

Alfrey-Price Q and e-values, 304, 307, 309, 310, 314, 334, 337, 342, 352, 353, 389, 393-395, 400, 416, 419, 424 MA monomer, 247, 272 Alkali cyanide, addition to fumarates, 64 Alkenyl benzyl ethers, MA copolymerization, 532 Alkenylsuccinic anhydride applications, 147, 175 double bond migration, 174 hydrolysis, 175 isomerization catalysts, 174 MA polymerization, 342 MA-olefin adducts, 147-151, 163-165, 172, 173 Alkoxysuccinic acids, preparation, 46 Alkyd resins, MA applications, 44, 479, 499 Alkyl acetoacetates... 

Alkylidene lactones, MA in synthesis, 231 Alkylmagnesium bromide dialkyl fumarate adducts, 234 dialkyl maleate adducts, 234 Alkylmaleic anhydride, synthesis from alkenylsuccinic anhydride, 175 Alkyl malonates... 

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