Phthalic dialdehyde

50 in H2O, soluble in methanol, ethanol, ethylene glycol, tetrahydrofuran 

Theis and Leder (1993) demonstrated in aerobic biofilm experiments with an oil field isolate of aerobic bacteria, containing predominantly Pseudomonas species, that OPA is more effective than formaldehyde (FA, 2.1a.) or glutaraldehyde (GA, 2.5.) in killing or inhibiting the growth of sessile microorganisms (see Table 16). OPA is effective without activation and is able to inactivate GA-restistant strains of Mycobacterium chelonae. On the other hand OPA unlike GA acts not sporicidal at its in-use concentration of 0.5% (w/v) and normal pH (6.5.). 

With regard to a proposed mechanism of action of OPA Simons et al. (2000) interpret the observation that OPA is a less potent crosslinking agent than GA as an influence of steric restrictions of the aromatic dialdehyde in contrast to GA which is composed of a flexible aliphatic chain. In addition the two carbonyl groups of OPA are part of a resonance stabilized system and consequently are less reactive than aliphatic aldehydes such as GA or FA in nucleophilic addition reactions. The fact that OPA in contrast to other aldehydes reacts only with 

It is recommended to use OPA for controlling biofouling caused by sessile and planctonic micro-organisms in industrial water systems, e.g. for pulp and paper manufacture and for oil field water flooding. Normal addition rates move between 10 to 250 ppm. A synergistic slime control effect is achieved, if a combination of bis [tetra-kis(hydroxymethyl)phosphonium] sulfate (3.6) and OPA is introduced into white water. 

Formaldehyde as such is often too volatile and too reactive to be used as a microbicide for the protection of materials or in disinfectants. It additionally produces unwelcome side-effects, and has an insufficient balanced range of activity. One therefore has looked for formaldehyde releasing compounds which do not exhibit the disadvantageous formaldehyde effects but maintain or even improve the antimicrobial action of formaldehyde. 

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The transformation of isoquinoline has been studied both under photochemical conditions with hydrogen peroxide, and in the dark with hydroxyl radicals (Beitz et al. 1998). The former resulted in fission of the pyridine ring with the formation of phthalic dialdehyde and phthalimide, whereas the major product from the latter reaction involved oxidation of the benzene ring with formation of the isoquinoline-5,8-quinone and a hydroxylated quinone. 

I.3.3 Miscellaneous reactions. Double aldol condensation of phthalic dialdehyde with thieno azepinedione 114 results in a 60% yield of naphtho derivative 115 (Scheme 23 (1999PHA645)). 

MAA Methacrylic acid, EGDMA Ethylenglycoldimethacrylate, DAM Diethylaminoethylaminoethylmethacrylate, VPY4-Vinylpiridine DVB Divinylbenzene, CMMC 7-Carboxymethoxy-4-methylcoumarin, AA Allylamine, 4MU 4-Methylumbelliferone, OP A o-Phthalic dialdehyde + beta-mercaptoethanol, APBA 3-Aminophenylboronic acid, TBA 3-Thiopheneboronic acid, DTAF 5-[(4,6-Dichlorotriazin-2-yl)amino]fluorescein, FITC Fluorescein isothiocyanate... 

Fig. 6.3 Interaction between phthalic dialdehyde, mercaptan group (OPA reagents) and primary amine (I) thioacetal formation (II) formation of fluorescent complex between hemithioacetal and primary amine (III).120 Reproduced with permission...

As ammonium ions give a reduction wave in tetra-alkyl-ammonium hydroxide solutions, a method for the determination of nitrogen was devised. The method consists of mineralization by the conventional Kjeldahl method used in the semimicro or micro modification. Because waves at very negative potentials (e.g. of ammonium ions) are usually less reproducible than waves at more positive potentials, the accuracy of this method is somewhat lower than that for ordinary polarographic analysis. Other types of polarographic determinations of ammonium ions could be applied, e.g. using the anodic waves corresponding to the formation of salts with mercury or the condensation with phthalic dialdehyde (p. 142). 

An interesting extrapolation of this synthesis deals with the preparation of the bispyridinium salt 62 from 1,2-phthalic dicarboxaldehyde and its subsequent reaction with primary amines (92BSB509).Tlie expected diimines 63 readily cyclize so that 2-aryl-l-arylimino-2,3-dihydro-l//-isoindoles 64 can be isolated in excellent yields (90-95%). Contrary to the reactions performed by employing the dialdehyde and amines directly, the syntheses involving the azinium salts do not produce those typical dark-colored complex mixtures of products (77JOC4217 85JHC449) (Scheme 20). 

Merz and Oldeweme [37] described a selective ion chromatographic procedure coupled with fluorescence detection for the determination of ammonia in which ammonia is separated from amines and alkaline metals and reacted with o-phthalic acid dialdehyde on a separate column. 

With some dibasic acids, the yields of the corresponding dialdehydes were unsatisfactory. For example, the reduction of succinyl dichloride267 and phthaloyl dichlo-ride268,269 gave, respectively, y-butyrolactone and phthalide as major products. With m- and / -phthalic dichlorides, however, the corresponding dialdehydes were obtained in 83 and 81% yields, respectively. 

When aldehydes, with or without a hydrogen, are treated with aluminum ethox-ide, one molecule is oxidized and another reduced, as in 19-81, but here they are found as the ester. The process is called the Tishchenko reaction. Crossed-Tishchenko reactions are also possible. With more strongly basic alkoxides, such as magnesium or sodium alkoxides, aldehydes with an a hydrogen give the aldol reaction. Treatment of a dialdehyde, such as phthalic dicarboxaldehyde (phthalaldehyde) with CaO, leads to a lactone.Like 19-81, this reaction has a mechanism that... 

Three compounds also have two carboxyl groups the dicarboxylic acids. 1,2-Benzenedioc acid (phthalic acid, 35) has two carboxyl groups with an ortho relationship. In 1,3-benzenedioc acid (isophthalic acid), the carboxyl groups are meta, and in 1,4-benzenedioc acid (terephthalic acid) the carboxyl groups have a para relationship The dialdehyde compounds have related names 1,2-ben-zenedial (phthalaldehyde 36 also phthalic dicarboxaldehyde), 1,3-benzenedial (isophthalaldehyde also isophthalic dicarboxaldehyde), and 1,4-benzenedial (terephthalaldehyde also terephthalic dicarboxaldehyde). 

The resulting dialdehyde was converted to derivatives. The reaction between phthalic anhydride and TNT is reported to form a phthalide derivative as shown in figure 8-58. However the reaction could not be duplicated. When TNT couples with diazonium... 

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