Carboxylates succinic anhydride

A further example is given below illustrating the use of a dibasic anhydride (succinic anhydride) the succinoylation reaction is a valuable one since it leads to aroyl carboxylic acids and ultimately to polynuclear hydrocarbons. This general scheme of synthesis of substituted hydrocarbons through the use of succinic anhydride is sometimes called the Haworth reaction. Thus a-tetralone (see below) may be reduced by the Clemmensen method to tetralin (tetrahydronaphthalene) and the latter converted into naphthalene either catal3d.ically or by means of sulphur or selenium (compare Section, VI,33). 

ATBN - amine terminated nitrile rubber X - Flory Huggins interaction parameter CPE - carboxylated polyethylene d - width at half height of the copolymer profile given by Kuhn statistical segment length DMAE - dimethyl amino ethanol r - interfacial tension reduction d - particle size reduction DSC - differential scanning calorimetry EMA - ethylene methyl acrylate copolymer ENR - epoxidized natural rubber EOR - ethylene olefin rubber EPDM - ethylene propylene diene monomer EPM - ethylene propylene monomer rubber EPR - ethylene propylene rubber EPR-g-SA - succinic anhydride grafted ethylene propylene rubber... 

Reactions with anhydrides afford interesting compounds having a carboxylic acid function (Table 26, entries 5 and 7 and Figure 40). It is notable that in the case of succinic anhydride, if the reaction is carried out at 25 °C, only one substitution occurs on the nitrogen atom, if the temperature is increased to 180 °C, there is a second substitution giving rise to a heterocyclic substituent (Table 26, entries 5-8). 

A variety of reagents could be used to carry out such a conversion (18,19). We chose to react the alkoxide ion with succinic anhydride (SA), because the alkoxide ion could be converted quantitatively to the carboxylate ion when excess of SA is used, and also because no side reactions are reported (19). The carboxylate anion, 3, thus formed was used to polymerize PVL giving the masked poly(oxyethylene)-b-po y(pivalolactone) co-polymeric salt, 4. The salt, 4, was converted to the teiechelomer, 5, by acid hydrolysis.. ... 

Almost every major structural class discussed to date has featured at least one nonsteroidal antiinflammatory carboxylic acid. It is thus perhaps not surprising to find a dibenzoheterocycle serving as the nucleus for one of these agents, furobufen (34). Straightforward Friedel-Crafts acylation of dibenzo-furan (33) with succinic anhydride affords a mixture of 2- and 3-acylated products, with the latter predominating. The mixture is esterified with methanol, and the methyl ester of the 3-isomer is separated by fractional crystallization. Hydrolysis back to the... 

Polymerization of oxiranes with succinic anhydride proceeded in the presence of PPL at 60 °C or 80 °C [63]. The ring-opening of the oxirane might proceed by a carboxylic acid catalyst, which is formed by the reaction of succinic anhydride with serine residue of the lipase catalyst. 

PLLA-fr-PCL) multiblock copolymers were prepared from the coupling reaction between the bischloroformates of carboxylated PLLA with diol-terminated PCL in the presence of pyridine [140]. LLA was polymerized with SnOCt2 and 1,6-hexanediol followed by the reaction with succinic anhydride to provide the dicarboxylated PLLA. The carboxyl end groups were subsequently transformed to acid chloride groups by the reaction with thionyl chloride (Scheme 65). As expected, the molecular weight distributions were broad for all samples (1.84 < Mw/Mn < 3.17). 

Figure 1.81 Succinic anhydride reacts with primary amine groups in a ring-opening process, creating an amide bond and forming a terminal carboxylate.

Succinic anhydride also is a convenient extender for creating spacer arms on chromatography supports. Supports derivatized with amine-terminal spacers may be succinylated to totally block the amine functionalities and form terminal carboxylic acid linkers for coupling amine-containing affinity ligands (Cuatrecasas, 1970). 

Molecules modified with succinic anhydride to create terminal carboxylate functionalities may be further conjugated to amine-containing molecules by use of amide bond forming reagents such as carbodiimides (Chapter 3, Section 1). 

Figure 7.12 Amine-containing dendrimers can be modified using a number of common reactive modification agents. Excess amine groups can be blocked using acetic anhydride, glycidol, or an NHS-mPEG compound. Amines also can be converted into carboxylates using succinic anhydride.

Figure 25.2 mPEG may be derivatized with succinic anhydride to produce a carboxylate end. A reactive NHS ester can be formed from this derivative by use of a carbodiimide-mediated reaction under nonaqueous conditions. The succinimidyl succinate-mPEG is highly reactive toward amine nucleophiles. 

Amine-terminated, G3 (PAMAM) dendrimer, (0.316 g 45.7 moles) was dissolved in anhydrous methyl sulfoxide (5 ml) in a 100 ml round-bottom flask flushed with dry nitrogen. After dendrimer had completely dissolved, succinic anhydride (Aldrich) (0.363 g 3.6 mmol) was added to the reaction mixture with vigorous stirring, and the mixture was allowed to react for 24 h at room temperature. The product solution was diluted with deionized water, transferred to 3500 MWCO dialysis tubing (Spectrum) and dialyzed against deionized water (18 Mil) for 3 d. The retentate solution was clarified by filtration through Whatman No. 1 filter paper, concentrated with a rotary evaporator, and lyophilized to yield a colorless powder (0.435 g, 94%). The product was analyzed by 13C-NMR, FT-IR, SEC and MALDI-MS. The analytical data were consistent with the expected carboxylic acid-terminated product. 

Reactions of wood with cyclic anhydrides do not yield a by-product, leaving the modified wood polymers with a covalently bonded carboxylic group an example is reaction with succinic anhydride (SA) (Figure4.1a). With reactions above 100°C there is some formation of diester observed (Figure 4.1b), resulting in cross-linking within the cell wall matrix (Matsuda, 1987). 

Suitable cyclic carboxylic anhydrides for this process are for example cz5-l,2-cyclohexane-dicarboxylic anhydride (HHPA), cz5-l,2-cyclohex-4-ene-dicarbo-xylic anhydride (THPA), phthalic anhydride (PA), succinic anhydride (SA), 1-oct-2-ene-succinic anhydride (OSA), and glutaric anhydride (GA) - see Fig. 9. 

Block (cap) residual lysine residues with a carboxylic acid by acylation using succinic anhydride prepared in l-methyl-2-pyrrolidinone,... 

Potassium carboxylate groups introduced onto the surface of carbon fibers initiated anionic polymerization of epoxides (e.g., styrene oxide, epichlorohydrin, and glycidyl phenyl ethers) and cyclic acid anhydrides (e.g., maleic anhydride, succinic anhydride, and phthalic anhydride) in the presence of 18-crown-6 [41]. 

On the other hand, polymeric carriers can also be modified to introduce reactive groups. Polysaccharides such as dextran and inulin may be activated [149] by periodate oxidation to create aldehyde groups, by succinic anhydride activation to create carboxylic groups, or by p-nitrophenyl chloroformate activation to create reactive ester groups. 

Chain Extension of -U-Polystyrene Hiols. A two-stage chain extension of the. -kJ -polystyrene diols was accomplished by carboxylation of the diols with succinic anhydride followed by chain extension with a diepoxide. The succinic anhydride reaction was carried out 120-130°C under nitrogen. The reaction was monitored bj changes in the carbonyl bands at 1715 and 1740 cm in the infrared spectra of the reaction mixtures. The resulting dicarboxylic acid polymers were chain-extended in bulk at 130°C for 9 hours with Sow s HER diepoxide, equivalent weight =171, using bis( 3,5-diisopropylsalicylato)Cr (III) as the catalyst. 

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