• Title/Summary/Keyword: 2-diol

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Synthesis of Long-Chain Unsaturated Acetates (장직쇄상(長直鎖狀) 불포화(不飽和) 초산화합물(醋酸化合物)의 합성(合成)에 관(關)한 연구(硏究))

  • Oh, Sung-Ki
    • Applied Biological Chemistry
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    • v.19 no.1
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    • pp.1-23
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    • 1976
  • The female moths of Lepidoptera comprising over 1,000,000 described species possess long-chain unsaturated alcohols or esters as the typical structure of potential sex attractants. In this experiment, various stereoisomers of $C_{16}-unsaturated$ acetates were synthesized for potential sex attractants; e.g., $CH_3(CH_2)_mCH=CH(CH_2)_nOR$ (m=0-12, n=1-13, R=H and $-COCH_3$). Seventeen acetates were spectrometrically examined so that the data would provide a ready catalog of gas chromatography and mass spectrometric data for comparison with natural insect sex attractants. Exclusively cis and trans isomers were obtained by the catalytic and chemical reduction methods, respectively. Commercially available $CH_3(CH_2)_mBr,\;CH_3(CH_2)_mC{\equiv}CH,\;HC{\equiv}C(CH_2)_nOH\;and\;HO(CH_2)_n\;OH$ were used for the synthetic starting material. 1-Alkynes, $CH_3(CH_2)_m\;C{\equiv}CH$ exceeding nine methylene groups did not condense with alkyl dihalides. The yield of coupling products was gradually decreased with increasing the molecular weight of diols. In the coupling reaction of $BrCH_2CH_2$ OTHP with acetylene gas, the tetrahydropyranyl ether of bromohydrin produced undesirable elimination product. In this experiment, it seems that p-toluenesulfonic acid is greatly favoured hydrolyzing agent over dilute sulfuric acid in the hydrolysis of the tetrahydropyranyl ether of long-chain alkynols.

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Preparation and Properties of Eco-friendly Waterborne Polyurethane-urea Primer for Thermoplastic Polypropylene Applied to Automobile Interiors (자동차 내장재용 열가소성 폴리프로필렌에 적용되는 선처리제용 친환경 수분산 폴리우레탄-우레아의 제조 및 성질)

  • Shin, Jong Sub;Park, Jin Myeong;Lee, Young Hee;Kim, Han Do
    • Clean Technology
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    • v.20 no.3
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    • pp.232-240
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    • 2014
  • The significance of thermoplastic polyolefin polypropylene (PP) lies in its potential to replace polyvinyl chloride (PVC), the most widely used material for automobile interiors (door trim, dash board), which discharges harmful compounds in certain conditions. Another benefit of PP (0.855 amorphous - 0.946 crystalline $g/cm^3$) is its low density compared to that of PVC ($1.1-1.45g/cm^3$), which reduces vehicle weight. Market demand for eco-friendly water-based adhesive/coating material is rising significantly as a substitute for solvent-based adhesive/coating material which emits VOC and causes harmful working conditions. Under such context, in this study, a series of eco-friendly waterborne polyurethane-urea primer (a paint product that allows finishing paint to adhere much better than if it were used alone) for hydrophobic PP were prepared from different mix of DMPA content, NCO/OH molar ratio, various wt% of silicone diol and various soft segment content, among which DMPA of 21 mole %, NCO/OH molar ratio of 1.2, modified silicone diol of 5 wt% and soft segment content of 73 wt% led to good adhesion strength. Additionally, the incorporation of optimum content of additives (0.5 wt% dispersing agent, 0.5 wt% levelling agent, 1.5 wt% antifoaming agent, 3.0 wt% matting agent) into the optimum waterborne polyurethane-urea also enabled good stability, levelling, antifoaming and non-glossy.

Synthesis of Melamine Phosphate-Polyurethane Composite Foam Blown by Water and Characterization of Its Thermal Properties (H2O로 발포된 멜라민포스페이트-폴리우레탄폼 복합체 합성과 열적 특성 분석)

  • Park, Kyeong-Kyu;Lee, Sang-Ho
    • Polymer(Korea)
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    • v.38 no.4
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    • pp.441-448
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    • 2014
  • Polyurethane/melamine phosphate composite foam (MP-PUF) was prepared from poly(adipate)diol/melamine phosphate composite (f=2), polyether-polyol (f=4.6), and PMDI (f=2.5). The thermal properties of MP-PUF such as morphology, closed-cell content, thermal conductivity, and thermal stabilities were characterized. Water was used as a blowing agent, and the composition of melamine phosphate (MP) was maintained at $1.43{\pm}0.3wt%$ of MP-PUF. As the content of water increased, the thermal conductivity of pure polyurethane foam (PUF) decreased, whereas the thermal conductivity of MP-PUF increased. The thermal stabilities of the PUF and the MP-PUF were maximized at 5 php $H_2O$, and then decreased at the higher $H_2O$ contents. The thermal stabilities of MP-PUF were greatly enhanced due to the synergetic effect of MP and urea, which was generated during the blowing process. The temperature of 50% residual mass of MP-PUF increased to $370{\sim}450^{\circ}C$ and the temperature of 30% residual mass exceeded over $700^{\circ}C$. Compared to the PUF, the temperature of 50% residual mass and 30% residual mass were higher than 25 and $70^{\circ}C$, respectively.

Low Formaldehyde Release D.P. Finish on Cotton Fabrics (면직물의 저$\cdot$Formaldehyde D.P. 가공)

  • Kim Sung Reon;Ryu Hyo Seon;Noh Hyung Eun
    • Journal of the Korean Society of Clothing and Textiles
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    • v.10 no.3
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    • pp.71-81
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    • 1986
  • In order to control the formaldehyde release from D.P. finished fabric, cotton fabric was padded in DMDHEU resin bath containing either $Zn(NO_3)_2$ or $MgCl_2$ catalyst and a form-aldehyde scavenger like Glycerol, Sorbitol, Formamide, Polyvinyl alcohol (PVA, n= 2000) or diols, then dried and cured. The results are as follows : 1. When Lewis acid catalyst like $Zn(NO_3)_2$ or $MgCl_2$ was added in pad bath, the fabric finished with $Zn(NO_3)_2$ catalyst released the lower formaldehyde than with $MgCl_2$. 2. When the effect of pad bath pH was examined with varying the kinds of catalyst and the scavenger, it was found that the pad bath pH influenced on the amount of formaldehyde release and the optimum pad bath pH is at 4.3. Especially, in case of finishing at pad bath pH 4.3 with adding Formamide, the amount of formaldehyde release was decreased by about $45\~$35\%$ with $Zn(NO_3)_2$, while by about $20\~$45\%$ with $MgCl_2$ catalyst. In case of varying the concentration of a scavenger (Formamide), $1\%$ concentration of a scavenger was found to be the optimum level ana the higher the curing temperature up to $180^{\circ}C$, the lesser the amount of formaldehyde release were observed. 3. When the diol was used as scavenger, the amount of formaldehyde release was decreased by about $40\~$50\%$, but the longer the intramolecular length between OH groups, the lessor the amount of decrease of formaldehyde release were observed. 4. When the mixture of scavengers (Formamide and Glycerol) was added in the pad bath, .synergistic effect on formaldehyde release between the two scavengers wasn't observed. 5. The tensile strength of the resin finished fabric was reduced with increasing the pad lath pH and was influenced by the kind of scavengers, and the tensile strength was severely reduced when scavengers, especially Formamide, was added. The wrinkle recovery property is generally improved by resin finish on cotton fabric. When Formamide was added, the wrinkle recovery property is slightly decreased compared with that of the fabrics resin finished without a scavenger, and when polyol was added, the wrinkle recovery property showed almost no change.

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Isolation of Ginsenoside${-Rh}_1$ and ${-Rh}_2$ by High Performance Liquid Chromatography (고속액체(高速液體) 크로마토그래피에 의(依)한 Ginsenoside ${-Rh}_1$${-Rh}_2$ 의 분리(分離))

  • Choi, Jin-Ho;Kim, Woo-Jung;Hong, Soon-Keun;Oh, Sung-Ki;Oura, Hikokichi
    • Korean Journal of Food Science and Technology
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    • v.13 no.1
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    • pp.57-66
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    • 1981
  • An effective method for isolation of the major components of ginseng saponin such as $ginsenoside-Rb_{1},\;-Rb_2,$ -Rc, -Rd, -Re and $-Rg_1$, and the minor components such as ginsenoside-Rf, $-Rg_2,\;and-Rh_1$, was developed and reported in previous papers (J. Korean Agr. Chem. Soc., 23(4), 199 and 206(1980) The conditions and procedures used for isolation and identification for ginsenosides described in the previous papers were not sufficient enough for clean separation of minor components, $ginsenoside-Rh_1,\;and-Rh_2$. In this work, modifications in extraction method and in mobile phase for HPLC were attempted. It was found that application of ethyl acetate extraction at $60^{\circ}C$ for 3 hr on crude saponin resulted in a removal of diol group saponin from crude saponin which made it possible for using higher portion of acetonitrile in mobile phase. The mixed solvents of acetonitrile : water (92 : 8 and 94 : 6) gave excellent resolution of $ginsenoside-Rh_1\;and\;-Rh_2$.

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Development and Application of Enzyme Immunoassay for Endosulfan Residue Analysis (Endosulfan 과 그 분해산물의 Enzyme Immunoassay에 의한 분석법의 개발과 응용)

  • Suh, Yong-Tack;Shim, Jae-Han;Lee, Kang-Bong
    • Korean Journal of Environmental Agriculture
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    • v.11 no.1
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    • pp.59-66
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    • 1992
  • An enzyme immunoassay(EIA) was developed for the analysis of insecticide endosulfan and its degradation products. The sensitivity and specificity of the antibody produced were examined. Optimal conditions in the ELISA system for residue analysis were also discussed. A mixed suspension of endosulfan-hemocyanin conjugate(ES-KLH) 1.1 mg/ml and Freund's adjuvant was injected subcutaneously to white rabbits and then collected antisera were tested for titers by indirect ELISA(1/24,000). Because of difficulties in the synthesis of endosulfan peroxidase conjugate, amine derivative of endosulfan-diol was synthesized and it showed 40% of conjugate yields(2mg/ml of conjugate). the highest sensitivity obtained enzyme-conjugate was a concentration of 200ng/ml. The detection limit of endosulfan in ELISA system was 5 ppb on the standard curve. In application of ELISA for residue analysis, the recoveries were really 100% both in the spiked soil and apple sample regardless of endosulfan concentration treated. On the other hand, chlorinated hydrocarbons of similar structure with endosulfan showed low cross-reactivity$(2.2%{\sim}29.2%).$

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Inhibition of Side Reactions Forming Dimers of Diols in the Selective Hydrogenation of Methacryl Aldehyde (메타아크릴 알데히드의 선택적 수소화에서 2가 알코올의 이합체 형성 부반응 억제효과)

  • Kook-Seung Shin;Mi-Sun Cha;Kyoung-Ku Kang;Chang-Soo Lee
    • Clean Technology
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    • v.29 no.2
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    • pp.79-86
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    • 2023
  • The homogeneous catalyst, Ru-MACHO-BH, selectively performs hydrogenation reactions only on the carbonyl group of α, β-unsaturated aldehyde compounds with extremely high reactivity and selectivity. However, the hydrogenation of α, β-unsaturated aldehydes involves a heterogeneous Diels-Alder reaction, resulting in the formation of significant amounts of byproducts, such as dimers. In this study, we used the Ru-MACHO-BH catalyst (Carbonyl hydrido (tetrahydroborato) [bis (2-diphenyl phosphino ethyl) amino] ruthenium(II)) to selectively hydrogenate the carbonyl group of a specific type of α, β-unsaturated aldehyde called methacryl aldehyde, leading to the synthesis of methallyl alcohol. Simultaneously, we applied diols to inhibit the formation of byproducts. The results demonstrate that monoethylene glycol can significantly reduce the formation of diols. Based on these results, we effectively suppressed the formation of dimers containing vinyl groups in methacryl aldehyde by using hydroquinone, which can efficiently inhibit the chemical interaction of vinyl groups. Consequently, the conversion rate of methacryl aldehyde was increased. Ultimately, by reducing the amount of the expensive homogeneous catalyst Ru-MACHO-BH to 1/10, we achieved a selectivity of over 90% and a yield of over 80% for the desired product, methallyl alcohol. These results provide a method to minimize yield reduction while reducing the usage of expensive catalysts, thereby improving cost-effectiveness. We expect that the reaction could be applied to various kinds of selective hydrogenation and has been successfully run on an industrial scale.

Human Acyl-CoA: Cholesterol Acyltransferase (hACAT) Inhibitory Activities of Triterpenoids from Roots of Glycine max (L.) Merr

  • Lee, Jin-Hwan;Ryu, Young-Bae;Lee, Byong-Won;Kim, Jin-Hyo;Lee, Woo-Song;Park, Yong-Dae;Jeong, Tae-Sook;Park, Ki-Hun
    • Bulletin of the Korean Chemical Society
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    • v.29 no.3
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    • pp.615-619
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    • 2008
  • Eight triterpenoids, six lanostanes 1-6, one lupenane 7, and one oleanane 8, were isolated by bioactivity-guided fractionation of the ethylacetate extract from roots of Glycine max (L.) Merr. All isolated compounds were examined for their inhibitory activities against human ACAT-1 (hACAT-1) and human ACAT-2 (hACAT-2). Among them, three triterpenoids showed potent hACAT inhibitory activities, (24R)-ethylcholest-5-ene-3,7-diol (1) and 3b -hydroxylup-20(29)-en-28-oic acid (7) exhibited more potent inhibitory activity against hACAT-1 (1: IC50 = 25.0 1.2 and 7: IC50 = 11.5 0.4 m M) than hACAT-2 (1: IC50 = 102.0 5.4 and 7: IC50 = 33.9 3.7 m M), respectively. Interestingly, 5a ,8a -epidioxy-24(R)-methylcholesta-6,22-diene-3b -ol (4) has proven to be a specific inhibitor against hACAT-1 (IC50 = 38.7 0.8 m M) compared to hACAT-2 (IC50 >200). In conclusion, this is the first study to demonstrate that triterpenoids of G. max have potent inhibitory activities against hACAT-1 and hACAT-2.

Mesoporous Silica-Carbon Composite Membranes for Simultaneous Hydrolysis and Separation of Chiral Epoxide (카본/메조세공 실리카 복합 막을 응용한 키랄 에폭사이드의 가수분해반응과 동시 분리)

  • Choi, Seong Dae;Jeon, Sang Kwon;Park, Geun Woo;Yang, Jin Young;Kim, Geon-Joong
    • Applied Chemistry for Engineering
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    • v.25 no.5
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    • pp.503-509
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    • 2014
  • The carbon/porous silica composite membrane was fabricated in a simple manner, which could be successfully for the simultaneous separation and production of chiral epoxides and 1,2-diols, based on their differences in hydrophilic/hydrophobic natures. The chiral Co(III)-$BF_3$ salen catalyst adopted in the membrane reactor system has given the very high enantioselectivity and recyclability in hydrolysis of terminal epoxides such as ECH, 1,2-EB, and SO. The optically pure epoxide and the chiral catalyst were collected in the organic phase after hydrolysis reaction. The hydrophilic water-soluble 1,2-diol product hydrolyzed by chiral salen diffused into the aqueous phase through the SBA-16 or NaY/SBA-16 silica composite layer during the reaction. The water acted simultaneously as a reactant and a solvent in the membrane system. One optical isomer was obtained with high purity and yield, and furthermore the catalysts could be recycled without observable loss in their activity in the continuous flow-type membrane reactor.

Ruthenium Complex Catalyzed Reaction of Diols or Triol with Amines (루테늄 착물 촉매를 이용한 디올 및 트리올과 아민과의 반응)

  • Sang Chul Shim;Young Zoo Youn;Jae Wook Lee;Dong Yeob Lee;Jae Goo Shim;Ju Hee Kim;Keun Tae Huh
    • Journal of the Korean Chemical Society
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    • v.37 no.11
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    • pp.967-973
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    • 1993
  • ${\alpha},{\omega}$-Diols such as 1,6-hexanediol and 1,7-heptanediol react with secondary amines in the presence of catalytic amount of ruthenium complex at 180$^{\circ}$C for 24 hrs to give the corresponding diamino compounds in good yields. The yield of diamino compound was affected by the molar ratio of ${\alpha},{\omega}$-diol to secondary amine. The reaction was also affected by the nature of the phosphorus ligands employed. On the other hand, aromatic primary amines react with 1,2,6-hexanetriol in the presence of RuCl_3{\cdot}H_2O-3PPh_3$ at 180$^{\circ}$C for 3 hours under argon atmosphere to give selectively 1-substituted aryl-3-hydroxyperhydroazepines in good yields. Selective synthesis of these products show that two primary hydroxy groups (1,6-positions) oxidize predominantly than secondary hydroxy group (2-position) by ruthenium-phosphorus complex. The yields were decreased according to the order of para-, meta- and ortho-substituent.

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