• Title/Summary/Keyword: Phthalic acid anhydride

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Synthesis of Quinazoline 4-one Derivatives from 2-Aminobenzamide (III) -Reaction with Acid Anhydrides- (2-Aminobenzamide로부터 Quinazoline 4-one계 유도체의 합성(III) -Acid anhydride와의 반응-)

  • Suh, Myung-Eun
    • YAKHAK HOEJI
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    • v.34 no.2
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    • pp.133-138
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    • 1990
  • The reaction of 2-aminobenzamide with phthalic acid anhydride In dioxane produced a bicyclic product 2,8-dioxoisoindole(1,2,a) quinazoline (I) in addition to hydrolysis product 2(2-Carboxyphenyl)-1,2-2H-quinazoline-4-one (II). The yields were 64% and 30% respectively. On the other hand, the same reaction in DMF afforded compound (I) and 2(2N-dimethyl carbamyl phenyl)-1,4-2H-quinazoline-4-one (III) in 30% and 60% yield respectively. The compound III was also obtained by the reaction of compound II with dimethylamine. However the reaction of 2-aminobenzamide with neat succinic acid anhydride gave only bicyclic product 2,8-oxopyrrolidine (2,1,a)-1,4-2H-quinazoline (IV) in 93%.

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Unexpected Rate Retardation in the Formation of Phthalic Anhydride from N-Methylphthalamic Acid in Acidic H2O-CH3CN Medium

  • Ariffin, Azhar;Khan, M. Niyaz
    • Bulletin of the Korean Chemical Society
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    • v.26 no.7
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    • pp.1037-1043
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    • 2005
  • Kinetic study on the cleavage of N-methylphthalamic acid (NMPA) in mixed acidic aqueous-acetonitrile solvent reveals the formation of both phthalic anhydride (PAn) (through O-cyclization) and N-methylphthalimide (NMPT) (through N-cyclization). The formation of NMPT varies from $\sim$20% to $\sim$3% with the increase in the content of acetonitrile from 2 to 70% v/v. Pseudo first-order rate constants for the formation of PAn are more than 4-fold larger than those for the formation of NMPT at 2% v/v $CH_3CN$ in mixed aqueous solvents. Pseudo first-order rate constants for alkaline hydrolysis of NMPT reveal a nonlinear decrease with increase in the content of $CH_3CN$ in mixed aqueous solvents.

Acylation of Wool Keratin with Dibasic Acid Anhydrides - on reaction mechanism - (2염기산 무수물에 의한 양모섬유의 아실화(I) - 반응메카니즘을 중심으로 -)

  • 신은주;박찬헌;최석철
    • Textile Coloration and Finishing
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    • v.7 no.1
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    • pp.65-71
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    • 1995
  • Wool yarns were treated in dimethylformamide solutions containing various concentrations of three dibasic acid anhydrides : succinic, itaconic, and phthalic anhydrides in various conditions. The structural aspects of these dibasic acid anhydrides are different : the succinic, itaconic, and phthalic acid anhydrides have saturated aliphatic etylene, unsaturated aliphatic vinyl and aromatic phenyl groups, respectively. The reaction mechanism of the acylation of wool keratin and some resction conditions were invastigated. And the results are as follows. 1. The N-acylation and formation of free carboxyl group were dominant rather than the O-acylation cross-linked on the side chain of polypeptide. The acylation of wool keratin is easier than that of silk fibroin. 2. The higher molecular weight, steric hinderance and resonance caused lower acylating reactivity. By the determination of acyl contents for acylated keratin, it was rerealed that the degree of acylation was succinic acid anhydride > itaconic acid anhhydride > phthalic acid anhydride.

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Preparation of 2,3,4,5-Tetrafluorobenzoic Acid (2,3,4,5-Tetrafluorobenzoic Acid의 합성)

  • Li, Hua;Wang, Hongkai;Zhao, Ruiju;Liu, Juan;Zhao, Zhengui;Hu, Guoqin;Liang, Zhengyong
    • Journal of the Korean Chemical Society
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    • v.54 no.6
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    • pp.744-748
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    • 2010
  • 2,3,4,5-Tetrafluorobenzoic acid, an important intermediates of fluoroquinolone antibiotics, was synthesized from tetrachloride phthalic anhydride through imidation, fluorination, hydrolysis and decarboxylation. The effects of phase transfer catalyst on imidation and fluorination reaction and the effects of surfactants on the hydrolysis reaction were studied, respectively. Experimental results showed that the imidation reaction time was greatly reduced in the presence of a phase transfer catalyst, hexadecyltrimethyl, resulting in imidation yield as high as 98.2%. The fluorination yield reached 81.3% when tetrabutylammonium bromide was chosen as a phase transfer catalyst. The hydrolysis reaction time was also decreased by adding hexadecyltrimethyl while increasing the yield to 88.6%. In the post-processing, the sublimation method was used to purify the product, and ideal effect was obtained. In the decarboxylation reaction, tetrafluoride phthalic acid was obtained by decarboxylation in the solvent of tri-n-butyl amine and decarboxylation yield reached 81.6%. Compared with the literature method, the overall reaction time of the improved method decreased from 53 h to 20.5 h and the total yield increased from 47.3% to 57.4%.

Photochemical Ring-Opening of Acid Anhydrides by $TiO_2$ Photocatalyst in Methanol

  • Kim, Sung-Sik;Mah, Yoon-Jung;Lee, Hye-Jong;Park, Sang-Kyu
    • Journal of Photoscience
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    • v.10 no.3
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    • pp.241-243
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    • 2003
  • Photoreactions of some carbonyl compounds with TiO$_2$ were investigated in methanol. Although 1,3-cyclohexanedione and phthalimide afforded 3-methoxy-2-cyclohexen-l-one and 3-methoxy-1-isoindolinone, respectively, acid anhydrides such as succinic, phthalic, and maleic anhydrides gave the monoesters of dicarboxylic acids in good to excellent yields, when they were irradiated on TiO$_2$ in methanol with 300 nm UV light.

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Biodegradation of Phthalic acid by White rot Fungus, Polyporus brumalis (백색부후균 Polyporus brumalis에 의한 프탈산의 분해)

  • Lee, Soo-Min;Park, Ki-Ryung;Lee, Sung-Suk;Kim, Myung-Kil;Choi, In-Gyu
    • Journal of the Korean Wood Science and Technology
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    • v.33 no.1 s.129
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    • pp.48-57
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    • 2005
  • Phthalate esters are known as plasticizers and some of them suspected as endocrine disrupting chemicals. In this study, in order to identify the mechanism of phthalate esters degradation by white rot fungus, phthalic acid, which is major metabolite in the biodegradation of phthalate esters, was used. Phthalic acid 50 ppm was treated in culture medium with Polyporus brumalis. The availability of ABTS oxidation was different from control and phthalic acid treated group after 4 days of incubation. The activity was gradually increased in control group, but not in phthalic acid treated group. Especially, esterase activity of control group was maximized at 10 days of incubation, and then decreased while the activity of phthalic acid treated group was increased. Glucose was used as a carbon source, and the difference of glucose consumption by control and phthalic acid treated group was not significant. However, after 6 days of incubation the residual glucose in culture medium was rapidly decreased. The consumption rate of phthalic acid treated group was lower than control. These results might indicate that the absorption of phthalic acid in culture medium was occurred by mycelium and metabolized through some pathways as that of glucose was. To clearify the chemical modification of phthalic acid in culture medium, phthalic acid was reacted under in vitro condition which mycelium was excluded. The metabolites were analyzed by GC/MS. The results showed that phthalic acid was converted to phthalic acid anhydride by the extracellular enzymes of P. brumalis.

A Study on the Acid Property and the Activity of Xylene Oxidation Catalyst (자일렌 산화반응 촉매의 산특성과 반응성에 관한 연구)

  • Kim, Taek-Joong;Kim, Young-Ho;Lee, Ho-In
    • Applied Chemistry for Engineering
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    • v.2 no.4
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    • pp.330-339
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    • 1991
  • The acid properties of $V_2O_5-TiO_2/SiO_2$ catalysts and the partial oxidation of o-xylene into phthalic anhydride had been investigated in order to relate the acid property of catalyst to the catalytic activity. $V_2O_5$ had both weak (V=O) and strong (V-O-V) acid sites which gave pyridine desorption peaks at $230^{\circ}C$ and $300^{\circ}C$, respectively, and the amount of weak acid sites at $230^{\circ}C$ decreased with the increase of calcination temperature. On the other hand, the amount of weak acid sites increased considerably by increasing the amount of $TiO_2$ to the $V_2O_5-TiO_2/SiO_5$, and the maximum value was shown at 20 and higher mole % of $TiO_2$ with respect to $SiO_2$. In the oxidation of o-xylene, $V_2O_5-TiO_2/SiO_2$ enhandced more the total conversion and the selectivity to phthalic anhydride than $V_2O_5/SiO_2$, and the higher $TiO_2$ ratio to $V_2O_5$ increased the total conversion but could not change the selectivity to phthalic anhydride. Weak acid sites (V=O) led o-xylene to partial oxidation producing phthalic anhydride by adsorbing o-xylene weakly, while acid sites (V-O-V) led it to total oxidation producing CO and $CO_2$ by adsorbing it strongly.

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Preparation and Properties of Polyolefin Graft Polymer available as a Primer for Polyurethane Adhesive (I) Synthesis of polyolefins with cyclic acid anhydride by free radical graft polymerization

  • Ryu, Ki Jung;Kim, Min Jung;Min, Seong Kee;Lee, Won Kee;Park, Chan Young
    • Elastomers and Composites
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    • v.50 no.2
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    • pp.119-125
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    • 2015
  • Because of their low surface free energy and absence of polar groups at the surface, polyolefins are substrates whose wetting and adhesion are very difficult. Free radical grafting of monomers to backbone polymer is one of the most attractive ways for the chemical modification of polymers. Synthesis of graft copolymer through graft polymerizations of PE and/or PP with phthalic anhydride (PhAn) was made and FTIR spectra of the graft polymer were the examined. And also the effects of phthalic anhydride content on the grafting ratio, thermal properties and contact angle of the graft polymer were examined.

Acylation of Wool Keratin with Dibasic Acid Anhydrides(II) ―on properties of acylated wool― (2염기산 무수물에 의한 양모섬유의 아실화(II) -아실화된 양모섬유의 성질을 중심으로-)

  • Shin, Eun Joo;Park, Chan Hun;Choi, Suk Chul
    • Textile Coloration and Finishing
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    • v.8 no.2
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    • pp.64-70
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    • 1996
  • Wool yarns were treated in dimethylformamide solutions containing various concntrations of three dibasic acid anhydrides: succinic, itaconic, and phthalic arthydrides in various conditions. The structurl aspects of these dibasic acid anhydries are different: succinic, itaconic, and phthalic acid arthydrides have saturated aliphatic ethylene, unsaturated aliphatic vinyl and aromatic phenyl one groups, respectively. The properties of acylated wool keratin are as follows: Decreasing amino group and increasing carboxyl group by acylation lowered the hydrophilic property, and then moisture regain, and decreased acid dye uptake and enhanced cationic dye uptake of wool keratin. In the case of phthalic acid anhydries, in spite of lowest acyl content, the minimum of moisture regain was resulted from the bulk benzen ring, occuping much more voids on wool keratin molecules than other reagents. Acid solubility was increased by the decrease of amino group and hydrogen bonding by acylation. Alkali solubility was also increased formation of new amide group on the side chain of keratin, which can be degraded easily by alkali. In the case of phthalic acid anhydride, the relative high solubility was resulted from the much higher molecular weight of dissolved fractions. The surface of wool keratin was not damaged by treatment with any acylating agent.

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Characterization of Colorless and Transparent Polyimide Films Synthesized with Various Amine Monomers (다양한 아민 단량체로 합성한 무색투명 폴리이미드 필름 특성)

  • Choi, Il-Hwan;Chang, Jin-Hae
    • Polymer(Korea)
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    • v.34 no.5
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    • pp.480-484
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    • 2010
  • A series of poly(amic acid)s(PAAs) was prepared by reacting 4,4'-(4,4'-isopropylidenediphenoxy) bis(phthalic anhydride)(BPADA) as the anhydride monomer and 2,2'-bis(trifluoromethyl) benzidine (TFB), bis(3-aminophenyl)sulfone (APS), 4,4'-methylenebis-(2-methylcyclohexylamine) (MMCA), or bis[4-(3-aminophenoxy) phenyl] sulfone (BAPS) as the amine monomer with 5 mol% melamine in N,N-dimethylacetamide (DMAc). Colorless and transparent polyimide (PI) films were obtained by casting the PAAs at various heat treatment temperatures. The thermo-mechanical properties and optical transparency of the PI films were investigated. The thermal properties of the PI films were examined using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and thermomechanical analysis (TMA), and their optical transparency were measured by spectrophotometry. The coefficient of thermal expansion (CTE) and yellow index (YI) values of all samples were in the range of $48.53-64.24ppm/^{\circ}C$ and < 3.0, respectively.