Norbomene dicarboxylic anhydride

Sulfonation was carried out by heating the asphalt with sulfur trioxide-trimethyl amine complex or sulfur trioxide-pyridine complex at temperatures near 135°C. Sulfamic acid treatment was also included in this series. Many other reagents were evaluated such as methyl methacrylate, 2-acrylamido-2-methylpropanesulfonic acid, 2-dimethyl-aminoethyl methacrylate, 2-vinylpyridine, 4-vinylpyridine, tetrahydro-phthalic anhydride, norbomene dicarboxylic anhydride, and phthalic anhydride. 

Keywords large scale, gas-solid reaction, catalytic hydrogenation, norbomene dicarboxylic anhydride, stereospecific... 

Cycloaddition of bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic anhydride 81 with cyclopentadiene was also studied by Bartlett et al., who found exclusive top addition, the top-endo/top-exo ratio being 3 2 [147]. The endolexo ratio is significantly different from that of 80 (60-70 1). The observed top selectivity in norbornadiene (80) and norbomene (81) derivatives is consistent with the inherent top reactivity of norbomanone 25 and norbomene 57. Orbital unsymmetrization of the dienophile... 

Norbomene end-capped polyimide oligomers (trade name LARC) are obtained by including 5-norbomene-2,3-dicarboxylic anhydride (nadic anhydride) (XLVII) in the polymerization reaction between a dianhydride and diamine [de Abajo, 1988 Hergenrother, 1987]. Heating the oligomer at 270-320°C results in a thermoset product. The main reaction... 

Poly(ethylene-co-norbomene-2,3-dicarboxylic acid anhydride) was prepared by co-polymerizing the respective monomers with the transition metal catalyst, di(3-t-butyl-2-hydroxy-l-(A-phenyhmino)benzene) titanium(IV). The polymerization was conducted at ambient temperature using methylaluminoxane as co-catalyst. After a 10 minute polymerization reaction scoping period 0.02 mol% of norbornene-2,3-dicarboxylic acid anhydride was incorporated into the co-polymer. 

In a subsequent investigation by the author poly(ethylene-co-norbornene dicar-boxylic acid anhydride) containing 0.03 mol% norbomene-2,3-dicarboxylic acid anhydride was prepared using the Step 2 vanadium analogue, (I). 

Some thermosets are made with maleic anhydride only, or with other unsaturated 1,2-dicarboxylic acids or anhydrides such as itaconic acid or methylenesuccinic acid [7], chlorendic acid or 1,4.5,6,7,7-hexachloro-5-norbornene-2,3-dicarboxylic acid (or anhydride), 1,4.5,6,7-pentachloro-5-norbornene-2,3-dicarboxylic acid anhydride or 1,4.5,6-tetrachloro-5-norbornene-2,3-dicarboxylic acid anhydride. These norbomene derivatives can be obtained from the Diels-Alder condensation of the chlorinated cyclopenta-1,3-dienes and maleic anhydride, as shown in the following reaction ... 

Figure 2 shows the dramatic increase in viscosity that results when maleic anhydride is added to asphalt. This increase occurs even in the absence of any added catalyst or peroxide initiator. Other anhydrides such as phthalic anhydride and 5-norbomene-2,3-dicarboxylic anhydride were not as effective. Note that there is no noticeable change in the viscosity of the unmodified asphalt. 

Chlorendic anhydride (l,4,5,6,7,7-hexachloro-5-norbomene-2,3-dicarboxylic anhydride) [115-27-5] M 370.9, m 234-236". 235-237", 238". Steam distil the anhydride or reciystallise it from H2O to yield pure diacid. The pure diacid yields the anhydride with AC2O. Am Chem Soc 69 62 1947]... 

Hexachloro-5-norbomene-2,3-dicarboxylic anhydride. See Chlorendic anhydride... 

Exo-oxabicylo-[2.2.1] hept-5-ene-2,3-dicarboxylic anhydride was prepared following the reported process [13]. 3-(4-carboxyphenylcarbamoyl)-7-oxabicyclo[2.2. l]hept-5-ene-2-carboxylic acid was prepared by using 1 equivalent of 4-aminobenzoic acid and 5.1 equivalent of acetic anhydride in presence of 0.29 equivalent of sodium acetate in dimethyl formamide solvent. Product was confirmed by H NMR and IR spectroscopy. The signal at 5 13.1 (bs, IH) ppm and 5 176 ppm was responsible for carboxylic acid group (Figs. 5 and 6) 5 8.0-8.2 (m, 2H) and 7.4-7.5 (m, 2H) ppm were responsible for aromatic protons, while 5 6.6 (s, 2H), 5.34 (s, 2H) and 3.1 (s, 2H) ppm peaks were for oxo-norbomene protons. Broad stretching frequency at 3244 cm was attributed to free carboxylic acid as shown in (Fig. 7a). 

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