Isophthaloyl chloride, preparation

The procedure described is a modification of the general procedure of Angyal2 for the preparation of aldehydes from benzylamines by the Sommelet reaction. Isophthalaldehyde has been prepared from w-xylene by preparation of the tetrachloro derivative and hydrolysis,3 from isophthaloyl chloride by the Rosenmund reaction,4 from a,a -dibromo-m-xylene by the Sommelet reaction,5 and from isophthaloyl chloride by reduction with lithium tri-Cbutoxyaluminumhydride.6... 

DSC 7g = 194°C, Tm = 260°C. A series of polyarylates can be prepared following die same procedure at various terephthaloyl chloride-isophthaloyl chloride ratios.434... 

This polymer can be synthesized from m-phenylenediamine and isophthaloyl chloride. It can be prepared by interfacial polymerization or solution polymerization.4,7 9 14... 

Fig. 7. Reaction of isophthaloyl chloride with 1 to prepare the bisketone-bisbenzocyclobutene monomer 14...

A poly(arylene ether phenylquinoxaline) of structure 14 was prepared by the aluminum chloride catalyzed reaction of 6,6 -bis[2-(4-phenoxyphenyl)-3-phenylquinoxaline] and isophthaloyl chloride in 1,2-dichloroethane [51]. The polymer had an inherent viscosity of 1.29 dL/g and a Tg of 224 °C. A polymer of the same chemical structure was prepared from the reaction of 3,3, 4,4 -tetraaminobiphenyl with l,3-bis(phenylglyoxalyl-4-phenoxy-4 -benzoyl)-benzene that gave a Tg of 239 °C [16], significantly higher than that prepared by the electrophilic route. In addition, a polymer of the same chemical structure (third polymer in Table 3) prepared via nucleophilic substitution exhibited a Tg of 240 °C. 

The polyamide-hydrazide 7 was prepared by solution polymerization in anhydrous dimethylacetamide from terephthaloyl chloride and p-amino-benzhydrazide at ca. 10 °C. The polyamide 8 resulted from the polycondensation of m-phenylenediamine with isophthaloyl chloride at —20 °C, whereas 9 was prepared by the reaction of terephthaloyl chloride with the complex diamine l,3-bis(3-aminobenzamide)benzene at —20 °C. The water flux and salt rejection through these membranes were summarized in Table 5. The polyamide-hydrazide (7) membranes were prepared from polymer solutions containing 6 7% polymer (Mv 3 34,000) by casting on glass plates. The material was placed in an oven for 30 60 min and coagulated in deionized... 

The polyamide used was obtained from a 1 1 mixture of m-and p-phenylenediamine and isophthaloyl chloride. All members were prepared under identical conditions (0.1 % aqueous solution, 50 kg/cm2)... 

Kraus et al.75 78) in Israel fabricated new aromatic phosphoric amide-carboxamide copolymers, which gave membranes high thermal stability, flame resistance, and salt rejection. Thus a copolymer was prepared from N,N -bis(3-aminophenyl)-N"-phenylphosphoric triamide 25, m-phenylenediamine and isophthaloyl chloride in... 

Another copolyamide containing carboxyl groups was prepared from 3,3 -methy-lenebis (anthranilic acid) 32, m-phenylenediamine, isophthaloyl chloride and terephth-aloyl chloride 89 K The reverse osmosis membrane from this copolyamide was made by treatment with transition metals (such as NiS04), Al, or Pb and shaping. 

Reverse osmosis membranes were also prepared from polyamides with pendant carboxamide groups 90). For example, 4,4 -diaminodiphenylmethane-3,3 -dicarbox-amide-isophthaloyl chloride copolymer 33 was dissolved in DMF containing LiCl, cast to 250 p thickness, dried at 100 °C for 15 min, and gelled in ice water to give a membrane with the water flux permeability of 900 1/m2 day and salt rejection of 80% (0.5% NaCl aqueous solution, 30 kg/cm2). After heating the membrane in... 

Heat-resistant polyamide membranes containing pendant sulfonamide groups were also fabricated 91 93). Thus the membrane prepared from 2,2 -disulfonamide-4,4 -diaminodiphenyl ether-isophthaloyl chloride copolymer 34 gave the water permeation rate of 1700 1/m2 day and salt rejection of 65 %. The film with 50 p... 

The poly(ether/amide) thin film composite membrane (PA-100) was developed by Riley et al., and is similar to the NS-101 membranes in structure and fabrication method 101 102). The membrane was prepared by depositing a thin layer of an aqueous solution of the adduct of polyepichlorohydrin with ethylenediamine, in place of an aqueous polyethyleneimine solution on the finely porous surface of a polysulfone support membrane and subsequently contacting the poly(ether/amide) layer with a water immiscible solution of isophthaloyl chloride. Water fluxes of 1400 16001/m2 xday and salt rejection greater than 98% have been attained with a 0.5% sodium chloride feed at an applied pressure of 28 kg/cm2. Limitations of this membrane include its poor chemical stability, temperature limitations, and associated flux decline due to compaction. 

Kawaguchi et al.105) in Teijin Ltd. prepared a similar polyamide composite membrane from piperazine, trimesoyl chloride, and isophthaloyl chloride on a polysulfone support. The membrane exhibited high chlorine-resistance and excellent pressure-resistance. When used for reverse osmosis of an aqueous solution of 0.5% NaCl and NaOCl (available Cl 4 5 ppm) at pH 6.5 7.0, 25 °C, and 42,5 kg/cm2, the water permeation was 1400 and 13301/m2 - day and desalination was 93.4% and 95.7% after 2 and 100 hr, respectively. 

Poly-1,3,4-oxadiazoles have a high thermal stability and have been used in film materials. Heat-resistant polymers have been prepared by incorporating 1,3,4-oxadiazole units into polymers (70MI42300) and heat-resistant polyamides have been synthesized from 3,5-bis(4-aminophenyl)-l,3,4-oxadiazole and isophthaloyl chloride (73MI42301). 

Two types of reactions involved in the preparation of NS-100 membranes are illustrated in Figure 2. The structural representation of polyethylenimine (PEI) is simplified to show only the reactive primary and secondary amine groups. In the first step the amine groups react rapidly with isophthaloyl chloride at the interface to produce a polyamide surface skin, while amine groups below... 

One approach used by Kawaguchi et al for preparation of the amphoteric membrane was the use of polyethylenimine having part of the amine groups neutralized with hydrochloric acid. The interfacial reactants were trimesoyl chloride (TMC), 3-chlorosulfonyl isophthaloyl chloride (SPC) and pyromellitlc acid chloride (PMC). 

V- 6-[2-(7-methyl[l, 8]naphthyridin-2-yl)ethyl]pyridine-2-yl acetamide 356 was prepared by the reaction of 2,7-dimethyl-l,8-naphthyridines 357 with n-butyllithi-um and 2-/V-acetylamino-6-bromomethylpyridine 358. Another carrier, viz., N-(l-methyl[l,8]naphthyridin-2-yl)-7V -(6-methylpyridin-2-yl)isophtalamide 359, was synthesized from 2-amino-7-methyl-l,8-naphthyridine 360, 2-amino-6-methylpyridine 226a and isophthaloyl chloride 361 in dry dichloromethane in the presence of tri-ethylamine. N,N -bis(l-mcl y [, 8]naphthyridin-2-yl)isophthalamide 362 was prepared from naphthyridines 360 and chloride 361 under analogous conditions. Isophthalamides 359 and 362 were used for the determination of L-( + )tartaric acid as complexes (1 1) soluble in chloroform (1999JIC661, 2001T4987). 

In the first two columns of Table III are given the equilibrium values for water uptake for the copolyoxamides prepared from isophthaloyl chloride and N,N -bis (uj-aminoalkyl)-oxamides of varying methylene chain length. The amount of absorbed water decreases with increasing aliphatic chain length, as expected, but not strictly monotonically the percent water uptake is plotted as a function of the number of methylene carbon atoms in the alkyl group in Figure 3. 

This membrane is highly sensitive to chemical attack by hypochlorite ion and hypochlorous acid in chlorinated feedwaters. Wrasidlo prepared a variation of the NS-100 membrane in which the primary amine groups of polyethylenimine were cyanoethylated before reaction with isophthaloyl chloride.27 This membrane was claimed to be chlorine-resistant, but was probably not so. 

Kurihara and coworkers at Toray Industries prepared several aminated derivatives of polyepichlorohydrin, then formed composite polyamide membranes by interfacial reaction with isophthaloyl chloride.38 Polyepichlorohydrin was converted to polyepiiodohydrin, then reacted with either4-(aminomethyl)piperidine, 3-(methylamino)hexahydroazepine, or 3-(amino)hexahydroazepine. Also, poly-epiaminohydrin was prepared by reduction of the azide derivative of polyepiiodohydrin. Best salt rejections were obtained if the polymeric amine formulation contained a substantial proportion of the monomeric amines as coreactants in the interfacial reaction. In tests on 3.5% sodium chloride at 800 psi and 25 C, salt rejections of 99.5% at fluxes of 8 to 9 gfd were characteristic. A three-zone barrier layer was produced, consisting of a heat-crosslinked polyamine gel (as in NS-100), a polyamide layer incorporating both the polymeric... 

A variety of engineering polymers and copolymers can be prepared by reacting an aromatic ether dithiol (HS—C6H4OC6H4SH) which has just been stannylated [by reaction with bis(tri- -butyltin)oxide] with isophthaloyl chloride in dry chloroform. The polymer is precipitated from methanol and the infrared spectrum is consistent with the structure of the polymer [16a] as... 

Aromatic polyamide fibers, better known as aramid fibers, have been defined as a long chain synthetic polyamide in which at least 85% of the amide linkages are attached directly to two aromatic rings [42] The first significant material of this type was introduced in 1961 by Du Pont as Nomex. It is poly(m-phenyleneisophthalamide), prepared from m-phenylenediamine and isophthaloyl chloride by interfacial polycondensation. 

Liquid crystalline poly(aryl ether ketone) polyesters are then prepared by copolymerization of the ester group containing poly(aryl ether ketone) with a liquid crystalline polyester. The crystalline polyester is synthesized from phenylhydroquinone ferf-butylhydroquinone, 2-chloroterephthaloyl chloride and isophthaloyl chloride. ... 

Polymers prepared from diphenyl ether and terephthaloyl chloride or mixtures of terephthaloyl and isophthaloyl chlorides contain xanthydrol end groups, which tend to make the polymer melt unstable. The addition of an appropriate comonomer, such as diphenoxybenzene, suppresses the xanthydrol end group content somewhat and improves the melt stabihty. Thus, higher diphenoxybenzene contents increase the thermal stability. 

The polymer can be prepared in dimethylacetamide from isophthaloyl chloride and m-phenylene-diamine in the presence of an acid scavenger at room temperature ... 

Very similar, wholly aromatic polyamides, with very regular structures, which reportedly result in better flexibility and higher temperature resistance, were reported. Preparation of these ordered copolyamides can be illustrated as follows. V,V-m-phenylene-bis(m-aminobenzamide) is formed first and then reacted with isophthaloyl chloride by interfacial condensation techniques to yield a product that melts at about 410 C ... 

Polymers prepared from diphenyl ether and terephthaloyl chloride or mixtures of terephthaloyl and isophthaloyl chlorides contain xanthydrol end groups, which tend to make the polymer melt unstable. The... 

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