• Title/Summary/Keyword: Reduction of carboxylic acid

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Molecular Analysis of Freeze-Tolerance Enhanced by Treatment of Trinexapac-Ethyl in Kentucky Bluegrass

  • Hwang, Cheol Ho
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.44 no.2
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    • pp.176-179
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    • 1999
  • Trinexapac-ethyl[ 4-(cyclopropyl- $\alpha$ -hydroxy-methylene)-3,5-dioxocyclohexane carboxylic acid ethylester] is a growth-retardant for plants by inhibiting a key step in biosynthesis of GA. A treatment of trinexapacethyl generally induces a reduction in vegetative growth and also inhibits heading. In addition, the trinexapacethyl was known to enhance the freeze-tolerance in annual bluegrass, however, the mechanism is not known yet. One possible reason for the enhanced freeze-tolerance may be the antifreeze protein known to be accumulated in intercellular space of the leaf during cold acclimation. In order to see the possible in-duction of the synthesis of antifreeze proteins by trinexacpacethyl, the apoplastic proteins extracted from Kentucky bluegrass treated with trinexapacethyl were analyzed by SDS-PAGE and the presence of the antifreeze protein was observed. In addition, western analysis showed the identity of the protein induced by both a cold acclimation and a trinexapacethyl treatment. It appears that an enhanced freeze-tolerance of the turf grass by trinexapacethyl is due to the synthesis and/or accumulation of the antifreeze protein similar to the enhanced freeze tolerance induced by cold acclimation.

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Synthesis of High-Performance Polycarboxylate(PC)-Type Superplasticizer, and Its Fluidity and Hydration Behavior in Cement Based-System (폴리카복실레이트계 고성능 유동화제의 합성과 시멘트계 내의 유동 및 수화 반응 거동)

  • Shin, Jin-Yong;Chae, Eun-Jin;Hong, Ji-Sook;Suh, Jeong-Kwon;Hwang, Eui-Hwan
    • Proceedings of the Korea Concrete Institute Conference
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    • 2006.05b
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    • pp.77-80
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    • 2006
  • Graft copolymerized polycarboxylate(PC)-type superplasticizers(PCs) which have carboxylic acid with $\pi$ bond among the molecular structure and polyethyleneglycol methyl ether methacrylate(PMEM) were synthesized by free radical reaction and investigated the chemical structure, polymerization condition, and physical and chemical properties. Also, the effects of PCs in the dispersion, adsorption and hydration of cement were evaluated. As the molecular weight of graft chain decreases, the adsorption amount on cement particles increased. It was advantageous for the flow to reduce molar ratio, the lower the side bone molecular weight, and increase the molar ratio, the larger the side bone molecular weight. The hydration reaction speed was highly delayed at day 1, due to increase in molar ratio and reduction in side bone molecular weight, but it was recovered in the days after.

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Reaction of Diisobutylaluminum Hydride-Dimethyl Sulfide Complex with Selected Organic Compounds Containing Representative Functional Groups. Comparison of the Reducing Characteristics of Diisobutylaluminum Hydride and Its Dimethyl Sulfide Complex

  • Cha, Jin-Soon;Jeong, Min-Kyu;Kwon, Oh-Oun;Lee, Keung-Dong;Lee, Hyung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.15 no.10
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    • pp.873-881
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    • 1994
  • The approximate rate and stoichiometry of the reaction of excess diisobutylaluminum hydride-dimethyl sulfide complex($DIBAH-SMe_2$) with organic compounds containing representative functional group under standardized conditions (toluene, $0{\circ}C$) were examined in order to define the reducing characterstics of the reagent and to compare the reducing power with DIBAH itself. In general, the reducing action of the complex is similar to that of DIBAH. However, the reducing power of the complex is weaker than that of DIBAH. All of the active hydrogen compounds including alcohols, amines, and thiols evolve hydrogen slowly. Aldehydes and ketones are reduced readily and quantitatively to give the corresponding alcohols. However, $DIBAH-SMe_2$ reduces carboxylic acids at a faster rate than DIBAH alone to the corresponding alcohols with a partial evolution of hydrogen. Similarly, acid chlorides, esters, and epoxides are readily reduced to the corresponding alcohols, but the reduction rate is much slower than that of DIBAH alone. Both primary aliphatic and aromatic amides examined evolve 1 equiv of hydrogen rapidly and are reduced slowly to the amines. Tertiary amides readily utilize 2 equiv of hydride for reduction. Nitriles consume 1 equiv of hydride rapidly but further hydride uptake is quite slow. Nitro compounds, azobenzene, and azoxybenzene are reduced moderately. Cyclohexanone oxime liberates ca. 0.8 equiv of hydrogen rapidly and is reduced to the N-hydroxylamine stage. Phenyl isocyanate is rapidly reduced to the imine stage, but further hydride uptake is quite sluggish. Pyridine reacts at a moderate rate with an uptake of one hydride in 48 h, while pyridine N-oxide reacts rapidly with consumption of 2 equiv of hydride for reduction in 6h. Similarly, disulfides and sulfoxide are readily reduced, whereas sulfide, sulfone, and sulfonic acid are inert to this reagent under these reaction conditions.

Studies on the Synthesis of Etodolac Derivatives as Potential Anti-inflammatory Agents (항염증제인 Etodolac 유도체의 합성에 관한 연구)

  • Cho, Hoon;Chung, Yong Seog;Jang, Hang Dong;Ryu, Seong Ryual
    • Applied Chemistry for Engineering
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    • v.10 no.1
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    • pp.135-137
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    • 1999
  • For the synthesis of new anti-inflammatory agents as indol derivatives, we have synthesized ${\alpha}$-benzoyl-1-ethyl-1,3,4,9-tetrahydro-8-ethyl-9-(N-benzoyl)pyrano[3,4-b]indole-1-acetic acid methyl ester. It was a new method for ${\alpha}$-substituted etodolac carboxylic acid. The synthetic process was composed of four steps, and 7-ethylindole and oxalyl chloride were used as starting materials. The third step, cyclization was carried out by addition of borontrifluoride diethyl etherate in 66% yield. The step of reduction and cyclization were simplified successfully. The final product, ${\alpha}$-benzoyl-1-ethyl-1,3,4,9-tetrahydro-8-ethyl-9-(N-benzoyl)pyrano[3,4-b]indole-1-acetic acid methyl ester was obtained in 66% yield by the reaction of methyl 1,8-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetate (etodollic acid methyl ester) and benzoyl chloride.

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Recovery of Gallium from Steelmaking Dust (제강더스트로부터 갈륨의 회수)

  • 양종규;이성식;김종화;황영길
    • Resources Recycling
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    • v.2 no.4
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    • pp.27-32
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    • 1993
  • A process has been studied to recover gallium from steelmaking dust which had several hundreds ppm of gallium. Aqueous solution containing 38 mg/l gallium was obtained by leaching of dust with 2.25 mol/l sulfuric acid. The leach liquor contained iron and zinc about 1,000 times greater than gallium. Gallium was then concentrated by ion exchanger of chelating resin with functional group of amino carboxylic acid after reduction of ferric ion to ferrous ion and pH adjustment. Gallium was concentrated to be 13 g/l in the resulting eluate by double ion exchanges. The liquor was further treated to remove impurities by solvent extraction technique empolying TOMAC as extractant. The galluim with 99% purity was finally obtainable.

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Reaction of Lithium n-Butylborohydride with Selected Organic Compounds Containing Representative Functional Groups

  • Chong-Suh Pyun;Jong-Chan Son;Nung-Min Yoon
    • Bulletin of the Korean Chemical Society
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    • v.4 no.1
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    • pp.3-9
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    • 1983
  • Lithium n-butylborohydride was prepared from borane-dimethylsulfide (BMS) and n-butyllithium, and the approximate rates and stoichiometrics of its reactions with selected organic compounds containing representative functional groups were studied in THF at room temperature. Phenol and benzenetiol liberated hydrogen quickly and quantitatively, and the reactions of primary alcohols, 2,6-di-ter-butylphenol and 1-hexanethiol liberated hydrogen quantitatively within 3 hrs, whereas the reactions of secondary and tertiary alcohols were very slow. Aldehydes and ketones were reduced rapidly and quantitatively to the corresponding alcohols. Cinnamaldehyde utilized 1 equiv. of hydride rapidly, suggesting the reduction to cinnamyl alcohol. Carboxylic acids evolved 1 equiv. of hydrogen rapidly and further reduction was not observed. Anhydrides utilized 2 equiv. of hydride rapidly but further hydride uptake was very slow, showing a half reduction. Acid chlorides were reduced to the alcohol stage very rapidly. All the esters examined were reduced to the corresponding alcohol rapidly. Lactones were also reduced rapidly. Expoxides took up 1 equiv. of hydride at a moderate rate to be reduced to the corresponding alcohols. Nitriles and primary amides were inert to this hydride system, whereas tertiary amide underwent slow reduction. Nitroethane and nitrobenzene were reduced slowly, however azobenzene and azoxybenzene were quite inert. Cyclohexanone oxime evolved 1 equiv. of hydrogen rapidly, but no further reduction was observed. Phenyl isocyanate and pyridine N-oxide were proceeded slowly, showing 1.74 and 1.53 hydride uptake, respectively in 24 hours. Diphenyl disulfide was reduced rapidly, whereas di-n-butyl disulfide, sulfone and sulfonic acids were inert or sluggish. n-Hexyl iodide and benzyl bromide reacted rapidly, but n-octyl bromide, n-octyl chloride, and benzyl chloride reacted very slowly.

Chemical Modification and Functionalisation of Poly(ethylene terephthalate) Fiber (폴리에틸렌테레프탈레이트 섬유의 화학개질 및 기능화)

  • 김인회;김성희
    • Polymer(Korea)
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    • v.26 no.3
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    • pp.389-399
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    • 2002
  • Poly (ethylene terephthalate) (PET) fibers were modified by deep UV irradiation which was produced by a low pressure mercury lamp. FT-IR and XPS analyses were used to elucidate the surface chemical composition of PET fibers treated with UV. Relative $O_{1s}$ intensity increased considerably and it was found that oxygen was incorporated in the form of COO on the fiber surface. FT-IR and XPS analyses proved the existence of carboxylic groups on the surfaces and the adsorption test of cationic compound further supported these results. The concentration of carboxylic acid group on the surface increased remarkably with Increasing irradiation time. XPS analysis and adsorption experiments proved that the surface structure of the UV-irradiated PET fibers were stable for 12 months. Antibacterial property and the deodorization rate of UV-irradiated PET fibers adsorbed with the berberine compound were investigated. Reduction rates of bacteria increased by about 21 to 99% compared to unradiated PET fiber. Deodorization rates of 23% for unradiated PET fiber increased to about 75% for 30 min irradiated samples.s.

Reducing Characteristics of Potassium Tri-sec-butylborohydride

  • Yoon, Nung-Min;Hwang, Young-Soo;Yang, Ho-Seok
    • Bulletin of the Korean Chemical Society
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    • v.10 no.4
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    • pp.382-388
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    • 1989
  • The approximate rates and stoichiometry of the reaction of excess potassium tri-sec-butylborohydride ($K_s-Bu_3BH$) with selected organic compounds containing representative functional groups were determined under the standard conditions (0$^{\circ}C$, THF) in order to define the characteristics of the reagent for selective reductions. Primary alcohols evolve hydrogen in 1 h, but secondary and tertiary alcohols and amines are inert to this reagent. On the other hand, phenols and thiols evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to the corresponding alcohols. Reduction of norcamphor gives 99.3% endo- and 0.7% exo-isomer of norboneols. The reagent rapidly reduces cinnamaldehyde to the cinamyl alcohol stage and shows no further uptake of hydride. p-Benzoquinone takes up one hydride rapidly with 0.32 equiv hydrogen evolution and anthraquinone is cleanly reduced to the 9,10-dihydoxyanthracene stage. Carboxylic acids liberate hydrogen rapidly and quantitatively, however further reduction does not occur. Anhydrides utilize 2 equiv of hydride and acyl chlorides are reduced to the corresponding alcohols rapidly. Lactones are reduced to the diol stage rapidly, whereas esters are reduced moderately (3-6 h). Terminal epoxides are rapidly reduced to the more substituted alcohols, but internal epoxides are reduced slowly. Primary and tertiary amides are inert to this reagent and nitriles are reduced very slowly. 1-Nitropropane evolves hydrogen rapidly without reduction and nitrobenzene is reduced to the azoxybenzene stage, whereas azobenzene and azoxybenzene are inert. Cyclohexanone oxime evolves hydrogen without reduction. Phenyl isocyanate utilizes 1 equiv of hydride to proceed to formanilide stage. Pyridine and quinoline are reduced slowly, however pyridine N-oxide takes up 1.5 equiv of hydride in 1 hr. Disulfides are rapidly reduced to the thiol stage, whereas sulfide, sulfoxide, sulfonic acid and sulfone are practically inert to this reagent. Primary alkyl bromide and iodide are reduced rapidly, but primary alkyl chloride, cyclohexyl bromide and cyclohexyl tosylate are reduced slowly.

General Characteristics of Taurine: A Review (타우린의 일반적 특성에 관한 선행연구 고찰)

  • Yoon, Jin A;Choi, Kyung-Soon;Shin, Kyung-Ok
    • The Korean Journal of Food And Nutrition
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    • v.28 no.3
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    • pp.404-414
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    • 2015
  • Taurine is one of the most abundant free ${\beta}$-amino acids in the human body that accounts for 0.1% of the human body weight. It has a sulfonic acid group in place of the more common carboxylic acid group. Mollusks and meat are the major dietary source of taurine, and mother's milks also include high levels of this amino acid. The leukocytes, heart, muscle, retina, kidney, bone, and brain contain more taurine than other organs. Furthermore, taurine can be synthesized in the brain and liver from cysteine. There are no side effects of excessive taurine intake in humans; however, in case of taurine deficiency, retinal abnormalities, reduced plasma taurine concentration, and other abnormalities may occur. Taurine enters the cell via a cell membrane receptor. It is excreted in the urine (approximately 95%) and feces (approximately 5%). Taurine has a number of features and functions, including conjugation with bile acid, reduction of blood cholesterol and triglyceride levels, promotion of neuron cell differentiation and growth, antioxidant effects, maintenance of cell membrane stability, retinal development, energy generation, depressant effects, regulation of calcium level, muscle contraction and relaxation, bone formation, anti-inflammatory effects, anti-cancer and anti-atherogenic effects, and osmotic pressure control. However, the properties, functions, and effects of taurine require further studies in future.

Reaction of Sodium Tris(diethylamino)aluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups

  • Cha, Jin-Soon;Jeoung, Min-Kyoo;Kim, Jong-Mi;Kwon, Oh-Oun;Lee, Keung-Dong;Kim, Eun-Ju
    • Bulletin of the Korean Chemical Society
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    • v.15 no.10
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    • pp.881-888
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    • 1994
  • The approximate rates and stoichiometry of the reaction of excess sodium tris(diethylamino)aluminum hydride (ST-DEA) with selected organic compounds containing representative functional groups under standardized conditions(tetrahydrofuran, $0{\circ}$) were studied in order to characterize the reducing characteristics of the reagent for selective reductions. The reducing ability of STDEA was also compared with those of the parent sodium aluminum hydride (SAH) and lithium tris(diethylamino)aluminum hydride (LTDEA). The reagent appears to be milder than LTDEA. Nevertheless, the reducing action of STDEA is very similar to that observed previously for LTDEA, as is the case of the corresponding parent sodium and lithium aluminum hydrides. STDEA shows a unique reducing characteristics. Thus, benzyl alcohol, phenol and 1-hexanol evolved hydrogen slowly, whereas 3-hexanol and 3-ethyl-3-pentanol, secondary and tertiary alcohols, were essentially inert to STDEA. Primary amine, such as n-hexylamine, evolved only 1 equivalent of hydrogen slowly. On the other hand, thiols examined were absolutely stable. STDEA reduced aidehydes and ketones rapidly to the corresponding alcohols. The stereoselectivity in the reduction of cyclic ketones by STDEA was similar to that by LTDEA. Quinones, such as p-benzoquinone and anthraquinone, were reduced to the corresponding 1,4-dihydroxycyclohexadienes without evolution of hydrogen. Carboxylic acids and anhydrides were reduced very slowly, whereas acid chlorides were reduced to the corresponding alcohols readily. Esters and epoxides were also reduced readily. Primary carboxamides consumed hydrides for reduction slowly with concurrent hydrogen evolution, but tertiary amides were readily reduced to the corresponding tertiary amines. The rate of reduction of aromatic nitriles was much faster than that of aliphatic nitriles. Nitrogen compounds examined were also reduced slowly. Finally, disulfide, sulfoxide, sulfone, and cyclohexyl tosylate were readily reduced without evolution of hydrogen. In addition to that, the reagent appears to be an excellent partial reducing agent: like LTDEA, STDEA converted ester and primary carboxamides to the corresponding aldehydes in good yields. Furthermore, the reagent reduced aromatic nitriles to the corresponding aldehydes chemoselectively in the presence of aliphatic nitriles. Consequently, STDEA can replace LTDEA effectively, with a higher selectivity, in most organic reductions.