• Title/Summary/Keyword: cyclohexene oxide

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Copolymerization and Oligomerization of Isobutylene Oxide (Isobutylene Oxide의 공중합 및 올리고머 반응)

  • 이윤배;김선길
    • Polymer(Korea)
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    • v.24 no.1
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    • pp.124-127
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    • 2000
  • To improve various physical properties of poly(isobutylene oxide) copolymers of isobutylene oxide and cyclohexene oxide have been synthesized with triisobutylaluminum as catalyst. The molecular weights of the copolymers are rather lower than that of poly(isobutylene oxide) prepared with diethylzinc catalyst. The glass transition temperatures of the copolymers are between those of two homopolymers. The copolymers of isobutylene oxide and vinyl cyclohexene oxide showed better thermal stability. Oligomer of isobutylene oxide has been synthesized for polyol and lubricant application. Acid catalyzed oligomerization gave vary complex mixture. But base catalyzed reaction afforded the pentamer and hexamer rich oligomer mixtures.

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Synthesis of the Terpolymers of Propylene Oxide, Cyclohexene Oxide, and Carbon dioxide (Propylene Oxide와 Cyclohexene Oxide와 CO2의 삼원 공중합체의 합성)

  • Lee, Yoon-Bae;Sung, Un-Gyung;Park, Hee-Kyong
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.12 no.2
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    • pp.1027-1031
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    • 2011
  • In order to use carbon dioxide, one of the green house gases, terpolymers have been synthesized from propylene oxide, cyclohexene oxide, and carbon dioxide with zinc glutarate as catalyst. The polymers have been investigated with FT-IR, $^1H$-NMR, DSC. The glass transition temperatures of terpolymers are dependendent upon mass ratio of the poly(alkylene carbonate by Fox equation.

Synthesis of Biodegradable Polymers with Carbon Dioixde (이산화탄소를 이용한 생분해성 고분자의 합성)

  • Shin Sang Chul;Shin Jae Shik;Lee Yoon Rae
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.5 no.6
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    • pp.521-525
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    • 2004
  • Biodegradation of poly(ethylene carbonate) (PEC) and their terpolymers has been investigated in vitro. PEC has been synthesized with ethylene oxide (EO) and carbon dioxide, which is one of the greenhouse gases using Zinc glutarate has been used as catalyst Carbonate terpolymers have been prepared by the use of EO, cyclohexene oxide(CHO), and carbon dioxide. High biodegradability of PEC and terpolymers with EO. has been observed. Very low biodegradation of poly(propylene carbonate) (PPC) and poly(cyclohexene carbonate) (PCHC) has been shown. The weight loss, FT-IR and SEM have been employed to characterize biodegradability.

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Effect of Lithium Chloride on the Borane Reduction of Organic Compound (보란-염화리튬에 의한 유기화합물의 환원반응)

  • Nung Min Yun;Jin Soon Cha
    • Journal of the Korean Chemical Society
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    • v.22 no.1
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    • pp.37-44
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    • 1978
  • The effect of lithium chloride on the borane reduction of organic compounds was studied for three ketones, seven acid derivatives, three epoxides and cyclohexene in tetrahydrofuran at $0^{\circ}$. When compared with borane itself, borane-lithium chloride system enhanced the rates of reductions markedly of 2-heptanone, acetophenone, benzoyl chloride, phthalic anhydride, and three epoxides, whereas the reductions of benzophenone, four esters and cyclohexene showed little or no effect. $BH_3$-LiCl (1 : 0.1) reduced styrene oxide in 2 hr at $0^{\circ}$ to give 94.2 % yield of alcohols, 1-to 2-phenylethanol ratio being 60.8 to 39.2. And in the reduction of cyclohexene oxide, $BH_3$-LiCl (1 : 0.1) gave a quantitative yield of cyclohexanol in 2 hr at $0{\circ}$, however $BH_3$-LiCl (1 : 1) gave 58 % cyclohexanol and 42 % 2-chlorocyclohexanol. In the reduction of cyclohexene oxide, lithium nitrate showed no rate enhancement even when the salt was added in large excess. A formation of lithium chloroborohydride in the$BH_3$-LiCl system is suggested.

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Microwave Synthesis of a Porous Metal-Organic Framework, Nickel(II) Dihydroxyterephthalate and its Catalytic Properties in Oxidation of Cyclohexene

  • Lee, Ji-Sun;Halligudi, Shiva B.;Jang, Nak-Han;Hwang, Dong-Won;Chang, Jong-San;Hwang, Young-Kyu
    • Bulletin of the Korean Chemical Society
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    • v.31 no.6
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    • pp.1489-1495
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    • 2010
  • A porous coordination solid of nickel(II) dihydroxyterephthalate has been synthesized by the microwave-assisted (MW) method. The synthesized nickel(II) dihyroxylterephthalate was designated by the general formula of [$Ni_2$(dhtp) $(H_2O)_2]{\cdot}8H_2O$ (where, dhtp = 2,5-dihydroxyterephthalate, denoted by Ni-DHTP). The effect of microwave-irradiation temperature and time of irradiation on the porosity and morphological changes in the solids have also been investigated. The catalytic performance of Ni-DHTP synthesized by MW method has been studied in the oxidation of cyclohexene with aqueous $H_2O_2$, which gave cyclohexene oxide as the primary product and 2-cyclohexene-1-ol as a major product.

Ring-Opening Polymerization of $\varepsilon$-Caprolactone and Cyclohexene Oxide Initiated by Aluminum $\beta$-Ketoamino Complexes: Steric and Electronic Effect of 3-Position Substituents of the Ligands

  • Liu, Binyuan;Li, Haiqing;Ha, Chang-Sik;Kim, Il;Yan, Weidong
    • Macromolecular Research
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    • v.16 no.5
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    • pp.441-445
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    • 2008
  • A series of aluminum complexes supported by $\beta$-ketoamino, ligand-bearing, 3-position substituents $LAlEt_2$ ($L=CH_3C(O)C(Cl)=C(CH_3)NAr\;(L_1)$, $L=CH_3C(O)C(H)=C(CH_3)NAr\;(L_2)$, $L=CH_3C(O)C(Ph)=C(CH_3)NAr\;(L_3)$, and $L=CH_3C(O)C(Me)=C(CH_3)NAr\;(L_4)$, $Ar=2,6-^iPr_2C6H_3$) were synthesized in situ and employed in the ring-opening polymerization (ROP) of $\varepsilon$-caprolactone ($\varepsilon$-CL) and cyclohexene oxide (CHO). The 3-position substituents on the $\beta$-ketoamino ligand backbone of the aluminum complexes influenced the catalyst activity remarkably for both ROP of $\varepsilon$-CL and CHO. Aluminum $\beta$-ketoamino complexes displayed different catalytic behavior in ROP of $\varepsilon$-CL and CHO. The order of the catalytic activity of $LAlEt_2$ was $L_1AlEt_2$>$L_2AlEt_2$>$L_3AlEt_2$>$L_4AlEt_2$ for ROP of $\varepsilon$-CL, being opposite to the electron-donating ability of the 3-position substituents on the $\beta$-ketoamino ligand, while the order of the catalytic activity for ROP of CHO was $L_1AlEt_2$>$L_3AlEt_2$>$L_4AlEt_2$>$L_2AlEt_2$. The effects of reaction temperature and time on the ROP were also investigated for both $\varepsilon$-CL and CHO.

Novel Syntheses of Isomers of Damascenone from Ethyl 2,6,6-Trimethyl-4-oxo-2-cyclohexene-1-carboxylate

  • Lee, Woo-Young;Jang, Se-Young;Lee, Jun-Gu;Chae, Woo-Ki
    • Bulletin of the Korean Chemical Society
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    • v.12 no.1
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    • pp.31-35
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    • 1991
  • Three isomers of damascenone, odorous terpenic ketones, have been synthesized conveniently from a same starting material, ethyl 2,6,6-trimethyl-4-oxo-2-cyclohexene-1-carboxylate(1), which was easily available by the acid-catalyzed condensation of mesityl oxide or acetone with ethyl acetoacetate. ${\alpha}$-Damascenone(7) was prepared by converting the enone ester 1 into the corresponding tosylhydrazone(4), followed by treating with 4 molar equiv of allyllithium. ${\beta}$-Damascenone(12) was synthesized by chemoselective reduction of 1 with sodium borohydride/cerium chloride to give corresponding allylic alcohol 8, conversion of 8 into acetate 9, and thermal decomposition of 9 with DBU to afford ethyl ${\beta}$-safranate(10), followed by reaction with an excess amount of allyllithium. ${\gamma}$-Damascenone(15) was obtained by dehydration of 8 with boric acid to furnish ${\gamma}$-safranate(13), followed by treatment with 2 molar equiv of allyllithium.