Alkyl succinic anhydride

Figure 1. Postulated sizing reactions of (a) alkyl ketene dimers and (b) alkyl succinic anhydrides. R. and R are short alkyl chains. Cell-OH represents cellulose.

Felix and Gatenholm (10) characterized the effects of compatibilizer molecular weight on the mechanical response of interphase design of cellulose fiber-rein-forced polypropylene composites. The cellulose fiber surface was treated with three different compatibilizers having a range of molecular weights alkyl succinic anhydride, Epolene 43, and Hercoprime G. The latter two compatibilizers are MA-g-PP. 

Friedel-Grafts Reactions. In the presence of Friedel-Crafts catalysts, succinic anhydride reacts with alkyl benzenes to form alkylben2oylpropionic acids (103), eg, the reaction with iadane gives a 97% yield of 4-oxo-(4,5-iQdanyl)butyric acid (eq. 6). 

Friedel-Crafts acylation of unsaturated fatty acids can be carried out with succinic anhydride ia the presence of alkyl aluminium haUde (104). 

V-Alkyl or A/-aryl succinimides can be prepared from the corresponding amines (107) or from succinic anhydride, ammonia, and the corresponding alcohol (108). Succinimides are also obtained by vapor-phase hydrogenation of the corresponding maleimides ia the presence of a catalyst (109). 

Alkyl-substituted succiiiimides are prepared by reaction of alkyleneamines such as TETA or TEPA with the corresponding alkyl substituted succinic anhydride (43). 

It is an Intelcsting fact, not yet fully explained, that the alkyl succinic acids give anhydrides more readily than succinic acid, and the greater the number of alkyl groups, the more readily is the anhychidc produced. Ihus the anhydride of tetramethyl succinic acid is so stable that it is not decomposed by water. 

An amine-terminated polyoxyalkylene having an average molecular weight from about 600 to about 10,000 can be acylated with a succinic acylating agent (e.g., hexadecenyl succinic anhydride or a Diels-Alder diacid) obtained from an unsaturated fatty acid [628,629] similarly, alkyl-aryl sulfonate salts [1319] can be used in lubrication. 

The trend towards increased calcium carbonate usage and therefore neutral pH paper making has meant that there has been a steady decline in the use of rosin and alum and a concomitant increase in the use of sizes which are effective at higher pH. Commercially the most important in this group are the alkenyl succinic anhydrides (ASA) and the alkyl ketene dimers (AKD). These are able to esterify fibre surfaces directly and are more effective at neutral to high pH. 

Similarly, a variety of 2-alkyl and 2-aryl succinic anhydrides (58b-g) were resolved with good to excellent enantioselectivities (66-98% ee) (Table 11) [216],... 

Miscellaneous Compounds. A saturated spirocychc pyrrohdine serves as the nucleus for a diamine that has been described as a hypohpemic agent. Treatment of the carbanion of the substituted cylcohexane carboxyhc ester (20-1) with methyl bromoacetate leads to the alkylation and formation of the diester (20-2). Saponification of the ester groups followed by reaction with acetic anhydride leads to ring closure of the succinic anhydride (20-3). Condensation with ammonia leads to the succinimide (20-4). The side chain is then added by alkylation of the anion on nitrogen with l-bromo-4-dimethylaminobutane (20-5). Reaction of this last intermediate with lithium aluminum hydride leads to the reduction of the carbonyl groups to methylene. This affords the pyrrolidine (20-6) atiprimod [22]. 

Sodium toluene dispersion of, 55, 65 Sodium p-toluenesulfinate, 57, 103 Spiro[4 n] alkenones, 58, 62 Spiro[cyclopentane-l,l -indene] 55, 94 Squalene, 56, 116 Squalene, 2,3-epoxy, 56, 116 Stannic chloride, 56, 97 Steroids synthesis, 58, 85 E Stilbene, 55, 115,58, 73 z-Stilbene, 58, 133 Styrene, 56, 35,58, 43 Styrene glycol, 55, 116 Styrene glycol dimesylate, 55, 116 Succinic acid, 58, 85 Succinic anhydride, 58, 85 Sucunimide, 56, 50, 58, 126 Succimmide, Vbromo, 55, 28, 56, 49 SULFIDE CONTRACTION, 55, 127 Sulfide, dimethyl-, 56, 37 SULFIDE SYNTHESIS, 58, 143,58, 138 SULFIDE SYNTHESIS ALKYL ARYL SULFIDES, 58, 143 SULFIDE SYNTHFSIS DIALKYL SULFIDES, 58, 143 SULFIDE SYNTHESIS UNSYMMETRI-CAL DIALKYL DISULFIDES, 58, 147 SULFONYL CYANIDES, 57, 88 Sulfur tetrafluoride, 57, 51... 

The procedure usually is unsuitable for tertiary alcohols since the reaction with phthalic anhydride or succinic anhydride either fails or results in dehydration of the alcohol. A few tertiary alkyl phthalates, however, have been prepared and resolved by first converting the alcohols to sodium or potassium salts and allowing these to react79 80 with phthalic anhydride. This modification has been applied successfully to dUa- and /S-santalols81 and cB-linalool.81 As already mentioned, glycols cannot be resolved by this procedure because they form polymeric esters when heated with phthalic or succinic anhydride. Phenols also usually form phthaleins or other condensation products instead of simple acid esters. 

Source Based on P. J. Darcy, R. J. Hart, and H. G. Heller, overcrowded molecules. Part 14. Photochromic systems involving (Z)-1 -methylpropylidene (diphenylmethylene)-succinic and (E)-3,5-dimethoxybenzylidene (alkyl- substituted methylene) succinic anhydrides, J. Chem. Soc., Perkin Trans. 1, 1978, 571-576. 

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