• 제목/요약/키워드: Benzoin reaction

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4,5-Diphenyl-Imidazolone의 合成 及 螢光效果에 關한 硏究 (Synthesis of 4,5-Diphenyl Imidazolone and Studies on its Fluorescent Effect)

  • 전풍진;김형숙
    • 대한화학회지
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    • 제4권1호
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    • pp.70-77
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    • 1957
  • 4,5-Diphenyl Imidazolone is synthesized from Benzoin, Urea, and Acetic acid catalyser. Nowadays, it is being used as an optical bleaching agent for wool and nylon textiles. Up to now, only one process of synthesis has been known. In order to find out the best conditions governing the yield were examined under various catalysers and conditions. In this experiment, the summary of results were as follows. a. On Acetic acid catalyser. The maximum yield conditions were mol ratio (Benzoin: Urea: Acetic acid) 1 : 2 : 14, Acetic acid concentration 99.9%. Reaction temperature 115$^{\circ}$. Under reaction time of 2 hours, above yield was 96.4%. b. On Mineral acid Catalyser. In using of Sulfonic acid, the color of solution was changed dark purlish black. With other mineral acid catalysers, in spite of increasing of temperature, it was proved that Benzoin floats on the solution, so that this reaction could not be continue. c. On Phosphoric acid catalyser. It was made clear that it can not be used for this reaction. d. On Sodium hydroxide catalyser. As one of Alkali catalyser, Sodium hydroxide was examined but this was unsuitable substance for this reaction. e. On Formic acid catalysers. The maximum yield conditions were mol ratio (Benzoin: Urea: Formic acid) 1: 2: 30. Formic acid concentration 85.%. Reaction temperature 150∼110$^{\circ}$. Under reaction time of 90 minutes, the best yield was 87%. Hereby, it was proved that organic acids such as Acetic acid and Formic acid can be used. When using Acetic acid, the yield was better than Formic acid, but it takes longer reaction time than Formic acid. About the fluorescent effect, the temperature of dye-bath must not be over 904,5-Diphenyl Imidazolone is synthesized from Benzoin, Urea, and Acetic acid catalyser. Nowadays, it is being used as an optical bleaching agent for wool and nylon textiles. Up to now, only one process of synthesis has been known. In order to find out the best conditions governing the yield were examined under various catalysers and conditions. In this experiment, the summary of results were as follows. a. On Acetic acid catalyser. The maximum yield conditions were mol ratio (Benzoin: Urea: Acetic acid) 1 : 2 : 14, Acetic acid concentration 99.9%. Reaction temperature 115$^{\circ}$. Under reaction time of 2 hours, above yield was 96.4%. b. On Mineral acid Catalyser. In using of Sulfonic acid, the color of solution was changed dark purlish black. With other mineral acid catalysers, in spite of increasing of temperature, it was proved that Benzoin floats on the solution, so that this reaction could not be continue. c. On Phosphoric acid catalyser. It was made clear that it can not be used for this reaction. d. On Sodium hydroxide catalyser. As one of Alkali catalyser, Sodium hydroxide was examined but this was unsuitable substance for this reaction. e. On Formic acid catalysers. The maximum yield conditions were mol ratio (Benzoin: Urea: Formic acid) 1: 2: 30. Formic acid concentration 85.%. Reaction temperature 150∼110$^{\circ}$. Under reaction time of 90 minutes, the best yield was 87%. Hereby, it was proved that organic acids such as Acetic acid and Formic acid can be used. When using Acetic acid, the yield was better than Formic acid, but it takes longer reaction time than Formic acid. About the fluorescent effect, the temperature of dye-bath must not be over 90$^{\circ}$. and the ratio of 4,5-Diphenyl Imidazolone and water should be from 1:50000. to 1:10000. It proved that the best effect on textiles, and the best condition were dye-temperature near 704,5-Diphenyl Imidazolone is synthesized from Benzoin, Urea, and Acetic acid catalyser. Nowadays, it is being used as an optical bleaching agent for wool and nylon textiles. Up to now, only one process of synthesis has been known. In order to find out the best conditions governing the yield were examined under various catalysers and conditions. In this experiment, the summary of results were as follows. a. On Acetic acid catalyser. The maximum yield conditions were mol ratio (Benzoin: Urea: Acetic acid) 1 : 2 : 14, Acetic acid concentration 99.9%. Reaction temperature 115$^{\circ}C$. . Under reaction time of 2 hours, above yield was 96.4%. b. On Mineral acid Catalyser. In using of Sulfonic acid, the color of solution was changed dark purlish black. With other mineral acid catalysers, in spite of increasing of temperature, it was proved that Benzoin floats on the solution, so that this reaction could not be continue. c. On Phosphoric acid catalyser. It was made clear that it can not be used for this reaction. d. On Sodium hydroxide catalyser. As one of Alkali catalyser, Sodium hydroxide was examined but this was unsuitable substance for this reaction. e. On Formic acid catalysers. The maximum yield conditions were mol ratio (Benzoin: Urea: Formic acid) 1: 2: 30. Formic acid concentration 85%. Reaction temperature 150∼110$^{\circ}C$. Under reaction time of 90 minutes, the best yield was 87%. Hereby, it was proved that organic acids such as Acetic acid and Formic acid can be used. When using Acetic acid, the yield was better than Formic acid, but it takes longer reaction time than Formic acid. About the fluorescent effect, the temperature of dye-bath must not be over 90$^{\circ}C$. and the ratio of 4,5-Diphenyl Imidazolone and water should be from 1:50000. to 1:10000. It proved that the best effect on textiles, and the best condition were dye-temperature near 70$^{\circ}C$. and dye-time 15 minutes. . and dye-time 15 minutes. . and the ratio of 4,5-Diphenyl Imidazolone and water should be from 1:50000. to 1:10000. It proved that the best effect on textiles, and the best condition were dye-temperature near 70$^{\circ}C$. and dye-time 15 minutes.

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Polymer Supported Cyanide as an Efficient Catalyst in Benzoin Condensation: An Efficient Route to α-Hydroxy Carbonyl Compounds

  • Kiasat, Ali Reza;Badri, Rashid;Sayyahi, Soheil
    • Bulletin of the Korean Chemical Society
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    • 제30권5호
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    • pp.1164-1166
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    • 2009
  • Aromatic aldehydes are efficiently self-condensed into $\alpha$-hydroxy carbonyl compounds by polystyrene-supported ammonium cyanide as an excellent organocatalyst in C-C bond formation. The reaction proceeds in water under mild reaction conditions. The polymeric catalyst can be easily separated by filtration and reused several times without appreciable loss of activity.

Benzoin Condensation Reactions of 5-Membered Heterocyclic Compounds Catalyzed by Thiazolium Salts

  • Chang Kiu Lee;Jin Soon Gong;Sin Kwan Seog;Jong-Gab Jun
    • Bulletin of the Korean Chemical Society
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    • 제14권1호
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    • pp.29-31
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    • 1993
  • Benzoin condensation reactions of furfurals and thiophenecarboxaldehydes in the presence of substituted benzyl and alkyl thiazolium salts were examined in order to improve the yield of the reaction and to examine the effect of the electronic nature of the catalysts. Thiophene derivatives gave thenils as the major products in low yields while furan derivatives gave only furoins in moderate to high yields.

Bezoin in Heterocyle Synthesis: Synthesis and Reactions of 2, 3-Diphenyl-4-cyanopyrrole-5-thione

  • Khalifa, Fathy A.;Zohdi, Hussein F.;Ibrahim, M.K.A.;Ismail, N.A.
    • Archives of Pharmacal Research
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    • 제13권4호
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    • pp.351-354
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    • 1990
  • 2, 3-diphenyl-4-cyano-pyrrole-5-thione (4) was either by the reaction of benzoin (1) and cyanothioacetamide (3) followed by cyclization using AcOH/sodium acetate or by refluxing a mixture of benzoin (1) and cyanothioacethamide in pyridine to afford directly 4. Several new pyrrole and pyrazole derivatives were synthesised using 4 as synthon. The structure of the newly synthesised derivatives were based on celemental and spectral data studies. Methylation of the SH group in 4 afforded 5. Reaction of 4 with ethyl bromo acetate afforded (6). Treatment of (5) and (6) with hydrazine hydrate afforded the same pyrazole derivative (10) through the intermediate (9). Treatment of 6 with aniline and phenylhydrazine afforded the pyrrole derivatives 8a, b respectively. Treatment of 6 while dill HCI gave 2, 3-diphenyl-4-cyano-pyrrole-5-one (7). Treatment of 6 with $NH_3$/EtOH afforded the amidic derivatives (11) with treatment of 6 $NH_3$/ heat then acidification it gave the carboxylic derivatives (12).

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Sulphanilic Acid촉매하에서 벤질/벤조인과 방향족 알데히드로부터 2,4,5-Triarylimidazoles의 간편한 One-pot 합성 (Sulphanilic Acid Catalyzed Facile One-pot Synthesis of 2,4,5-Triarylimidazoles From Benzil/Benzoin and Aromatic Aldehydes)

  • Mohammed, A.F.;kokare, N.D.;Sangshetti, J.N.;Shinde, D.B.
    • 대한화학회지
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    • 제51권5호
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    • pp.418-422
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    • 2007
  • Sulphanilic Acid 촉매를 사용한 벤조인 또는 벤질, 초산암모늄 그리고 방향족 알데히드의 축합반응을 통한 간단하고 높은 수율의 2,4,5-Triarylimidazoles의 One-pot 합성에 대한 보고 값싼 가격의 촉매,높은 수율 그리고 짧은 반응 시간은 제시된 방법의 장점이다.

Photochemical Reductions of Benzil and Benzoin in the Presence of Triethylamine and TiO? Photocatalyst

  • Park, Joon-Woo;Kim, Eun-Kyung;Koh Park, Kwang-Hee
    • Bulletin of the Korean Chemical Society
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    • 제23권9호
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    • pp.1229-1258
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    • 2002
  • This paper reports the photochemical reduction of benzil 1 to benzoin 2 and the reduction of 2 to hydrobenzoin 4 in deoxygenated solvents in the presence of triethylamine (TEA) and/or TiO2. Without TEA or TiO2, the photolysis of 1 resulted in very low yield of 2. The presence of TEA or TiO2 increased the rate of disappearance of 1 and the yield of 2, which were further increased considerably by the presence of water. The photoreduction of 1 to 2 proceeds through an electron transfer to 1 from TEA or hole-scavenged excited TiO2 followed by protonation. In the reaction medium of 88 : 7 : 2 : 3 CH3CN/CH3OH/H2O/TEA with 2.5 $㎎/m{\ell}$ of TiO2, the yield of 2 was as high as 85 % at 50 % conversion of 1. The photolysis of 2 in homogeneous media resulted in photo-cleavage to benzoyl and hydroxybenzyl radicals, which are mostly converted to benzaldehyde. The reduction product 4 is formed in low yield through the dimerization of hydroxybenzyl radicals. The addition of TEA increased the conversion rate of 2 and the yield of 4 significantly. This was attributed to the scavenging effect of TEA for benzoyl radical to produce N,N-diethylbenzamide and the photoreduction of benzaldehyde in the presence of TEA. The ratio of $(\pm)$ and meso isomers of 4 obtained from the photochemical reaction is about 1.1. This ratio is the same as that from the photochemical reduction of benzaldehyde in the presence of TEA. In the TiO2-sensitized photochemical reduction of 2, meso-4 was obtained in moderate yield. The reduction of 2 to 4 proceeds through two consecutive electron/proton transfer processes on the surface of the photocatalyst without involvement of ${\alpha}-cleavage$. The radical 11 initially formed from 2 by one electron/proton process can also combine with hydroxy methyl radical, which is generated after hole trapping of excited TiO2 by methanol, to produce 1,2-diphenylpropenone after dehydration reaction.

스티렌 그라프트 폴리프로필렌 부직포의 제조와 특성 (Preparation and Characteristics of Polypropylene Nonwoven Fabric Grafted by Styrene)

  • 김상률;나춘기
    • 한국의류산업학회지
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    • 제6권3호
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    • pp.377-383
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    • 2004
  • Photografting of styrene (St) on polypropylene (PP) nonwoven fabric using benzoin ethyl ether (BEE) as a photosensitizer was investigated. Inhibition of homopolymerization was achieved by adding various concentrations of $FeSO_4{\cdot}7H_2O$, $CuSO_4{\cdot}5H_2O$ and Mohr's salt. As St concentration was increased, the degree of grafting was increased as to a specific value and then decreased, and the effect of BEE concentration showed the same tendency. It was also found that the degree of grafting increased with reaction time and reaction temperature. Addition of the polyfunctional monomers and $H_2SO_4$ to the grafting system accelerated the photografting. The melting temperature, molecular weight, tensile strength and elongation were decreased with the increase in the degree of grafting.

An Efficient Synthesis of 2,4,5-Triaryl-1H-Imidazole Derivatives Catalyzed by Boric Acid in Aqueous Media Under Ultrasound-Irradiation

  • Shelke, Kiran F.;Sapkal, Suryakant;Sonal, Swapnil;Madje, Balaji R.;Shingate, Bapurao B.;Shingare, Murlidhar S.
    • Bulletin of the Korean Chemical Society
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    • 제30권5호
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    • pp.1057-1060
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    • 2009
  • Boric acid ($BO_3H_3$) is an inexpensive, efficient and mild catalyst for the synthesis of 2,4,5-triaryl-1H-imidazoles in excellent yields from the one-pot three-component condensation of benzil/benzoin, an aldehydes and ammonium acetate in aqueous media under ultrasound at room temperature. The remarkable advantages offered by this method are green catalyst, mild reaction conditions, simple procedures, much faster reactions and excellent yield of products.