• Title/Summary/Keyword: Succinic acid anhydride

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Practical Synthesis of N-Hydroxysuccinimide Using Lewis Acid Catalyst (Lewis Acid 촉매를 이용한 N-Hydroxysuccinimide의 실용적 합성법 연구)

  • Kim, Dong Nyeon;Kim, Seok Chan
    • Applied Chemistry for Engineering
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    • v.30 no.3
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    • pp.313-315
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    • 2019
  • A new synthetic method for N-hydroxysuccinimide (NHS), which is widely used in fine chemical and cosmetic industries, was developed. In a conventional synthesis, NHS is obtained by reacting $NH_2OH$ with succinic anhydride in a yield of about 70% using strong acid as a catalyst, which has an advantage of obtaining NHS relatively easily. However, it is expensive because of using a high cost succinic anhydride. In order to overcome this issue, we developed a new synthetic method for NHS with a moderate yield of 80% using a low cost succinic acid instead of succinic anhydride, alongside a stable Lewis acid catalyst, Zn acetate. As a result of the economic evaluation, it was confirmed that the cost reduction effect was about 15%.

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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Application Study on Skin Beauty Culture, Green Laver Culture and Synthesis of ${\alpha},{\beta}$-Dichloro Substituted Chitosan Succinic Acid Derivatives (${\alpha},{\beta}$-Dichloro 치환기를 갖는 Chitosan Succinic Acid 유도체 합성과 피부미용 및 해태 김 양식 응용에 관한 연구)

  • Ryu, Soung-Ryual
    • Journal of the Korean Applied Science and Technology
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    • v.29 no.3
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    • pp.503-515
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    • 2012
  • ${\alpha},{\beta}$-Dichlorosuccinic acid was synthesized through the reaction of maleic anhydride with $Cl_2$(g) and ultra violet(200~300nm) wavelength in the presence of $CCl_4$. The second reaction of N-(${\alpha},{\beta}$-dichloro)succinic acid contained glucosamine derivatives(I) was accomplished by a modification of the general acylation using excess ${\alpha},{\beta}$-dichlorosuccinic anhydride in the presence of 2% acetic acid with methanol as a solvent at elevated temperature($70^{\circ}C$). We considered organic acid derivatives were useful especially of treatment for the cultivating porphyra and skin beauty culture.

Synthesis of Succinic Acid from Hydrogenation of Maleic Anhydride (무수말레인산의 수소화 반응에 의한 호박산 합성)

  • Kim, Ji Sun;Baek, Jae Ho;Kim, Myung Hwan;Hong, Seong-Soo;Lee, Man Sig
    • Applied Chemistry for Engineering
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    • v.24 no.6
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    • pp.650-655
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    • 2013
  • In this study, the synthesis of succinic acid from hydrogenation of maleic anhydride over Pd/C were performed in aqueous solution at various reaction conditions. We confirmed that the distribution of product was different according to process parameters. When increasing the reaction pressure and agitation speed, the by-product decreased and the purity of succinic acid increased. From the result, we may conclude that the reaction pressure and agitation speed are important factors for promoting the mass transfer rate of gas-liquid interface by increasing gas-liquid solubility in liquid hydrogenation. When the reaction pressure increased from 5 bar to 10 bar, the reaction rate increased 2.14 times. When the agitation speed increased from 300 rpm to 700 rpm, the reaction rate increased 2.75 times.

Application Study of Skin Beauty Culture, Green Laver Culture and Synthesis of ${\alpha}$-Chloro Substituted Chitosan Succinic Acid Derivatives (${\alpha}$-Chloro 치환기를 갖는 Chitosan Succinic Acid 유도체 합성 및 피부미용과 해태 김 양식 응용 연구)

  • Ryu, Soung-Ryual
    • Journal of Integrative Natural Science
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    • v.4 no.4
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    • pp.323-331
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    • 2011
  • In this study, ${\alpha}$-chlorosuccinic acid was synthesized through the reaction of maleic anhydride with HCl(g), (UV)250 nm~300 nm wavelength in presence of $CCl_4$. For the second reaction of N-(monochloro)succinic acid contained glucosamine derivatives(I) was accomplished by a modification of the general acylation using excess ${\alpha}$-chlorosuccinic anhydride in the presence of 2% acetic acid with methanol condition as a solvent at elevated temperature($70^{\circ}C$). We considered organic acid derivatives were useful especially for treatment for the cultivating porphyra.

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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Chemical Transformation of Succinic Acid by Using Amberlite IR-120 and the Reusability of Catalyst (Amberlite IR-120를 사용한 숙신산의 화학적 전환과 촉매의 재 사용성)

  • Lee, Byong-Wook;Kim, Hwang-Min;Kim, Young-Wun;Kim, Yeong-Joon
    • Journal of the Korean Chemical Society
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    • v.55 no.6
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    • pp.1007-1011
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    • 2011
  • Dioctyl succinates and succinic anhydride were synthesized from succinic acid in the presence of a cation exchange resin, Amberlite IR-120. The synthesis of dioctyl succinate from succinic acid and octanol was perfomed in 18 h reflux condition with Amberlite IR-120 and the isolated yield of product was over 90%. For the synthesis of succinic anhydride, succinic acid was refluxed in isopropenyl acetate for 18 h with Amberlite IR-120 as a catalyst. The long reaction time was significantly reduced to less than 10 min under microwave irradiation. The catalyst was reusable at least 4 times with keeping product yield of higher than 80%.

Synthesis and Lubricant Additive Properties of Succinimidyl-type Compounds (숙신이미드계 화합물의 합성 및 그의 윤활특성)

  • Park, Chan-gu;Kang, Hocheol;Park, Jong-mok;Lee, Byung Min;Kim, Dong-Pyo
    • Applied Chemistry for Engineering
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    • v.17 no.5
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    • pp.498-503
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    • 2006
  • i-(2',5'-Diketotetrahydrofuranyl)octadecenyl acid (OSA), an intermediate for the lubricating oil additive, was prepared by the ene-reaction of oleic acid with maleic anhydride. The reaction progress was monitored by gas chromatography by analyzing the amount of OSA. The series of succinimidyl compounds were synthesized by the reaction of alkyl amines and OSA. As a kind of lubricant additives, demulsibility, anti-wear, and anti-corrosion properties of these succinimidyl compounds were measured. The derivative of octadecylamine which has relatively long-chained alkyl group has showed good properties.

Studies on the Separation of Maleic Anhydride Adducts of Soybean Oil (大豆油의 말레酸化生成物의 分別에 關한 硏究)

  • Suh Ho Park
    • Journal of the Korean Chemical Society
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    • v.21 no.1
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    • pp.67-72
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    • 1977
  • Author studied on the isolation technique and properties of the products obtained by the reaction of soybean oil with maleic anhydride. Before studying above purpose, oleic acid and linoleic acid contained in soybean oil were reacted with maleic anhydride. Thin-layer chromatography using silica coated plate and solvent system consisting of petroleum ether-diethyl ether = 7:3∼5:5 (v/v) resulted in good effects on the isolation of maleic anhydride adducts. Four fractions were separated and fraction No. 2 were analyzed by IR & UV spectrophotometer, obtaining the following conclusions. In the case of oleic acid adduct and linoleic acid adduct, it were conjectured that the succinic acid type adduct was formed. In the case of conjugated $C_{18}$ fatty acid adduct, cyclohexene type adduct was formed which differed from oleic acid and linoleic acid adduct.

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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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