Epoxy dicarboxylate

Fig. 6. Structures of common cutin and suberin monomers, and ranges of typical composition values. Non-substituted fatty acids are not represented. There are overlaps in some classes of monomers (e.g. some monomers are epoxy hydroxy-fatty acids, of epoxy dicarboxylic acids).

It has been shown that chirality does not necessarily need to be located on a tetrahedral carbon atom, as in the case of the fran -epoxy dicarboxylates (Scheme 2.33) [238]. For example, the axial chirality of the racemic iron-tricarbonyl complex [239] and of the allenic carboxylic ester shown below [240], was well recognized by PLE. 

Imidazole-4,5-dicarboxylic acids, coupling, 5, 403 decarboxylation, 5, 434 1-substituted synthesis, 5, 468 synthesis, 5, 362, 402, 484 Imidazole-4,5-dione, l-alkyl-2-phenyl-synthesis, 5, 129, 479 Imidazole-2,4-diones tautomerism, 5, 370 Imidazole-4,5-diones tautomerism, 5, 370 Imidazole-2,4-dithione, 5,5-diphenyl-tautomerism, 5, 370 Imidazole-2,4-dithiones tautomerism, 5, 370 Imidazolepropanol synthesis, 5, 486 Imidazoles accelerators epoxy resins, 1, 407... 

For this use, the preferred powders are based on acrylic, epoxy or polyester and epoxy resins. For best colour, epoxy resins are crosslinked with anhydrides of dicarboxylic acids in the straight epoxy coatings, or with saturated polyesters of high acid content in the epoxy-polyester type. Acrylics contain epoxide rings via, for example, glycidyl methacrylate (CH2=C(CH3) —CO—O—CHj—CH —CH2), and these groups crosslink... 

Epoxy-18-oxo C18 Dicarboxylic acids Malus pumila young fruit ... 

In addition to triterpenoids in the bark of Betula spp., suberin (a biopolyester comprising primarily hydroxy, epoxy and dicarboxylic acids) is also present, as... 

The complexes Ru(pydic)(tpy), Ru(pydic)(pybox-R ) (pydic=pyridine-2,6-dicarboxylate, pybox-Rj=chiral bis(oxazolinyl)pyridines with R=PP, Ph (Fig. 1.37) [105] epoxidised trani-stilbene (as complex/PhlO, Ph OAc), TBHP or OJ CHjClj). Asymmetric oxidations of trani-stilbene were similarly achieved in toluene, benzene and CH Cl with e.e. values from 40-80% cf mech. Ch. 1) [53, 54, 81,97]. Asynunetric epoxidations of rranx-stilbene, styrene, tranx-fl-methylsty-rene and 1-hexene were catalysed by [RuCl(SOMePh)(bpy)j] /TBHP or Ph(IOAc)y CHjCy40°C e.e. values of 33-94% were obtained of the (R. R) forms of the epoxides of tra i-stilbene, tranx-P-methylstyrene [52]. The system Ru(CO)(TPP)/ (CljpyNO)/HBr/C H epoxidised fullerene (C ) to 1,2-epoxy[60]fullerene with 1,2 3,4 di-epoxy and 1,2 3,4 9,10 h- 1,2 3,4 11,12 tri-epoxy species [106]. 

Eoreon and Suzuki18 8 carried out the hydration of ezo-1,2-epoxy l.icydo 2.2.1]oct ne aro-4,C dicarboxylic add, and isolated a lactone i unloved to bo thoskoletal rearrangement product depicted in Eq. (636b). 

In reactions of the enol acetate, 2-(l-acetoxyvinyl)furan Id with DMAD, both of the alternative diene systems reacted with the dienophile, and a mixture of dimethyl 7-acetoxybenzofuran-4,5-dicarboxylate 4d and dimethyl 3-(l-acetoxyvinyl)-3,6-epoxy-3,6-dihydrophthalate 2d was obtained (73AJC1059). 

Horold, S. and Kleiner, H. J., (Clariant GmbH), Phosphorus-containing dicarboxylic reaction product of epoxy resins and phosphorus acid (anhydride) with hardener, U.S. Patent, 1999 5 959 043. 

The commercial flexibilizing reactive diluents are predominantly glycidyl derivatives of glycols, dimerized acids, or reaction products of dicarboxylic acids with epoxy resins. The properties of certain polyepoxy diluents are summarized in Table 8.3. Some of, but not all, these materials provide good reactivity with aliphatic primary amines at room temperature. 

Numbered peaks refer to the carbon chain length of (no prefix) dicarboxylic acids, (T prefix) tricarboxylic acids and (0 prefix) oxirane acids. X identifies 1,2-epoxy-1,1,2,3-propanetetracarboxylic acid. 

SYNS AQUATHOL 3,6-ENDOOXOHEXAHYDRO-PHTHALIC ACID ENDOTHALL ENDOTHAL TECHNICAL 3,6-ENDOXOHEXAHYDROPHTHALIC ACID 3,6-endo-EPOXY-l,2-CYCLOHEXANEDI-CARBOXYLIC ACID HEXAHYDRO-3,6-endo-OXYPHTHALIC ACID HYDOUT HYDROTHAD47 7-OXABICYCLO(2.2,l)HEPTANE-2,3-DICARBOXYLIC ACID RCRA WASTE NUMBER P088 TRI-ENDOTHAL... 

Antipova and coworkers [193] increased the hydrolytic stability and adhesive strength of EPR by adding an epoxy resin, dicarboxylic acid anhydride and dialkyl tin dicarboxylate. The dialkyl tin dicarboxylate does not react with the double bonds in keto allyl groups but at radical sites, thus the replacement of labile hydrogen atoms by the two electronegative groups of organo tin ompounds results in an increase in EPR stability. 

The most important applications of peroxyacetic acid are the epoxi-dation [250, 251, 252, 254, 257, 258] and anti hydroxylation of double bonds [241, 252, the Dakin reaction of aldehydes [259, the Baeyer-Villiger reaction of ketones [148, 254, 258, 260, 261, 262] the oxidation of primary amines to nitroso [iJi] or nitrocompounds [253], of tertiary amines to amine oxides [i58, 263], of sulfides to sulfoxides and sulfones [264, 265], and of iodo compounds to iodoso or iodoxy compounds [266, 267] the degradation of alkynes [268] and diketones [269, 270, 271] to carboxylic acids and the oxidative opening of aromatic rings to aromatic dicarboxylic acids [256, 272, 271, 272,273, 274]. Occasionally, peroxyacetic acid is used for the dehydrogenation [275] and oxidation of aromatic compounds to quinones [249], of alcohols to ketones [276], of aldehyde acetals to carboxylic acids [277], and of lactams to imides [225,255]. The last two reactions are carried out in the presence of manganese salts. The oxidation of alcohols to ketones is catalyzed by chromium trioxide, and the role of peroxyacetic acid is to reoxidize the trivalent chromium [276]. 

Cpierenone, U5P. Eplcrenone. 9,lla-epoxy-l7a-hy-droxy-3-oxopregn-4-enc-7a.2l-dicarboxylic acid, y-lac-tone. methyl ester (Inspra). is a new aldosterone antagonist that was approved by the FDA in 2002 for the treatment of hypertension. 

The reactivity of epoxy groups towards nucleophilic and electrophilic species can be explained through the release of ring strain in the three member oxirane group. Nucleophilic curatives such as amines or mercaptans attack the secondary ring carbon while electrophilic curatives behave as Lewis or Bronsted acids. The epoxy ring can be opened by hydroxyl or other epoxy group aided by tertiary amines, Lewis acids or coreactants such as primary amines, mercaptans and dicarboxylic acids ... 

There is an alternative method of making functional derivatives for polymerization. Durene can be condensed with formaldehyde in the presence of hydrochloric acid and zinc chloride to give the bis-chloromethyl durene(75). This can be converted into a number of derivatives from which polymers can be made, e.g. durene-1,4-dicarboxylic acid for polyamides(76), the diacetic acid for polyesters(77,78) or for polyamides(79), the diisocyanatomethyl derivative for polyureas and polyurethanes(80,81), the dimethanol derivative for polyurethanes(82) and for epoxies(83), while the bis chloromethyl derivative has also been proposed for making polyethers (with bisphenol A)(84). In each case, the attraction from the durene derivative has been the introduction of higher melting points and inproved softening properties. None of these polymers have been commercialized, possibly in part because of the difficulty of obtaining durene at suitable-prices. 

This co-unsaturated ester is an excellent substrate for a number of important polymers It can be converted into a Cn-dicarboxylic acid, which can be utilized for the manufadure of polyesters, or into 10-aminodecanoic add, which leads to nylon 10. The epoxidation of the terminal double bond provides 9,10-epoxydecanoic acid, which can be used for the production of epoxy resins. 

Oxidation of unsaturated oleochemicals can proceed in different ways, and yields numerous products. Typical oxidations of fatty acids are, for instance, ketoniza-tions yielding keto acids [72, 73], hydroxylations to bishydroxy acids [74], epoxida-tions to epoxy acids [75-78] and oxidative splitting reactions [72, 74] yielding mixtures of mono- and dicarboxylic acids. However, not only the double bond but also the functional group of the fatty compound, can be oxidized. One example is the ruthenium-catalyzed oxidation of fatty alcohols to fatty aldehydes or fatty acids... 

According to a recent report, however, the carbonyl ylides formed under these conditions may isomerize and lead to adducts different from those normally expected87. Thus, (5)-l-acetyl-2-(diazoacetyl)pyrrolidine (8). derived from /V-acetyl-i.-proline, upon treatment with dimethyl butynedioate in the presence of a catalytic amount of rhodium(II) acetate dimer at 25 °C affords only 10% of the expected adduct dimethyl 5,8-epoxy-2,3,5,8,9,9a-hexahydro-5-methyl-9-oxo-lH-pyrrolo[l, 2-o]azepine-6,7-dicarboxylate (9). Instead, dimethyl 1,2,8,9-tetrahydro-5-methyl-l-oxo-3a//,7//-furo[3,2-g]pyrrolizine-3a,4-dicarboxylate (10) is obtained in 87% yield. The formation of this product is explained via an isomeric ylide87 and thus occurs with complete loss of chiral information. 

Carboxylic acid and anhydride curing agents are used to a lesser extent in aerospace applications as compared to the amines which have mechanical properties and cure conditions that can be tailored to a wider variety of specific applications. Anhydrides tend to be somewhat brittle but offer useful service as high as 250 °C with novolac-type epoxy resins. In addition, the aliphatic dicarboxylic acid anhydrides give tough and sometimes flexible properties which are useful in encapsulation applications. 

Irradiation of a solution of 51 in benzene causes an interesting isomerization to 4-phenyl-4-oxazolin-2-one (56), via an epoxy isocyanate141 lEq. (33)1. In the presence of 1,1-dimethoxyethylene, a 2 + 2 cycloaddition occurs in competition with a-cleavage to give 57. Compound 51 is also reported to react with dimethylacetylene dicarboxylate... 

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