• Bulletin of the Korean Chemical Society
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• v.16 no.4
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• pp.326-331
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• 1995

Poly(enaryloxynitriles) containing Schiff bases were prepared from p-bis(1-chloro-2,2-dicyanovinyl)benzene (2) and various aromatic diols having Schiff base moiety by interfacial polymerization. The chemical structure of the polymers was confirmed through synthesis of their corresponding model compounds. All the polymers were soluble in polar aprotic solvents and their brittle films were cast from DMF solution. They showed a large exotherm around 340 ℃ attributable to the chemical change of dicyanovinyl group. Especially, curing of azomethine group was observed to occur at 390 ℃ by differential scanning calorimetry. According to the thermogravimetric analyses, they exhibited excellent thermal stability with 60-90% residual weight at 500 ℃ in nitrogen.

• 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.

• Journal of the Korean Wood Science and Technology
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• v.29 no.3
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• pp.99-103
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• 2001

Three flavan-3,4-diol derivatives were isolated from the heartwood of Robinia pseudoacacia and characterized by spectroscopic methods including $^1H$ and $^{13}C$ NMR and positive FAB-MS. The structures were identified as 4,4'-dimethoxy-, 4-ethoxy- and 4-ethoxy-4'-methoxy-2,3-trans-3,4-cis-(+)-leucorobinetinidin.

• Natural Product Sciences
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• v.25 no.4
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• pp.348-353
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• 2019

Soluble epoxide hydrolases (sEH) are enzymes present in all living organisms, metabolize epoxy fatty acids to 1,2-diols. sEH in the metabolism of polyunsaturated fatty acids plays a key role in inflammation. In addition, the endogenous lipid mediators in cardiovascular disease are also broken down to diols by the action of sEH that enhanced cardiovascular protection. In this study, sEH inhibitory guided fractionation led to the isolation of five phenolic compounds trans-resveratrol (1), trans-piceatannol (2), sulfuretin (3), (+)-balanophonin (4), and cassigarol E (5) from the ethanol extract of the seeds of Passiflora edulis Sims cultivated in Vietnam. The chemical structures of isolated compounds were determined by the interpretation of NMR spectral data, mass spectra, and comparison with data from the literature. The soluble epoxide hydrolase (sEH) inhibitory activity of isolated compounds was evaluated. Among them, trans-piceatannol (2) showed the most potent inhibitory activity on sEH with an IC₅₀ value of 3.4 μM. This study marks the first time that sulfuretin (3) was isolated from Passiflora edulis as well as (+)-balanophonin (4), and cassigarol E (5) were isolated from Passiflora genus.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.44 no.4
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• pp.363-373
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• 2018

In recent years, parabens used as preservatives in cosmetics have become a problem of human safety. Therefore, in this study, we tried to evaluate the preservative efficacy of 1,3-butylene glycol, 1,2-hexanediol, and 1,2-pentanediol as a preservative system to replace parabens. 1,3-Butylene glycol was added to cosmetic creams at a concentration of between 5 and 25%. The preservative efficacy of 1,3-butylene glycol was determined using a M-3 challenge test, as recommended by the Personal Care Products Council (formally CTFA). The alkane diols, such as 1,2-hexanediol and 1,2-pentanediol, were assessed in a similar manner. An evaluation of the preservative efficacy of 1,3-butylene glycol revealed that it was effective against all tested microbial strains at a concentration of 25%. We also investigated the efficacy of combinations of 0.3% phenoxyethanol and 0.1% ethylhexylglycerin. Finally, we tested the alkane diols, including 1,2-hexanediol and 1,2-pentanediol, as an alternative to the preservative 0.3% phenoxyethanol. Both 1% 1,2-hexanediol and 1% 1,2-pentanediol demonstrated preservative efficacy. Taken together, our study demonstrated that the formulation of 25% 1,3-butylene glycol and 0.1% ethylhexylglycerin, 1% 1,2-hexanediol, and 1% 1,2-pentanediol had the best preservative efficacy of the compositions tested. Thus, this study suggests that the formulation is a possibility of substituting parabens preservatives, which has been used in cosmetics and has become a safety issue.

• KSBB Journal
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• v.9 no.3
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• pp.246-252
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• 1994

Enzyme-catalyzed polycondensatlon reaction of aliphatic polyesters with several repeating units was studied using the biocatalytic activities of lipases from different sources. Porcine pancreatic lipase (PPL) was found to be best in utilizing bls(2,2,2-trichloroethyl) glutarate and 1,4-butanediol as substrafes. The reaction was also catalyzed to some extent by the lipases from Humicola lanuginos and Psudomonas sp. In the series of short-chain diols(C2-C4), bis(2,2,2-trichloroethyl) glutarate was iransesterified fastest with 1,4-butanediol and for the long-chain diols (PEG-300-PEG-1000), the reaction was fastest with PEG-400. With PEGs, only monoesterification product was obtained. PPL functioned well in relatively hydrophilic organic solvents such as tetrahydrofuran(THF), ether and acetonitrile. The reaction rate was accelerated as the reaction temperature was raised from $20^{\circ}C$ to $60^{\circ}C$ while Mn values of the reaction products were not affected by the reaction temperature. End group analysis by NMR showed that Mn values of the polymer were in the range of 1500-4000 daltons.

• 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.

• Journal of the Korean Society of Tobacco Science
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• v.9 no.2
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• pp.77-85
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• 1987

$\alpha$, $\beta$-4.8.13-Duvatriene-1, 3-diols was identified as the major component of diterponoid extracted from Nicotiana Tabacum L. The isolated duvatriendiol was thermolyged at 300'c under a stream of nitrogen. The approximately 20 compounds were separated from the thermolyzates and the 9 compounds of them were identified with GC/MS. However, the thermolyzates identified in this study differed in distribution from the products under the condition of a different temperature or photooxidation.

• Applied Biological Chemistry
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• v.40 no.6
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• pp.588-592
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• 1997

The new type ligand, bisphosphonites, were easily prepared through ligand exchange reaction of bis (diethylamino)phosphine with diols. These bisphosphonites reacted with $(COD)^2Rh^+BF_4\;^-$ to corresponding bisphosphonite-rhodium(I) comlexes, of which X-ray crystallography was for the first time investigated. This organometallic compound was applicated in hydroformylation reaction as catalyst, and proved to be very effective one.

• Bulletin of the Korean Chemical Society
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• v.15 no.12
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• pp.1089-1093
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• 1994

Polyesters containing enaryloxynitriles moiety have been newly prepared from p-bis[1-[4-(3-hydroxypropyl)phenoxy]-2,2-dicyano vinyl]benzene (3) and common diols with terephthaloyl chloride. The copolyesters have a good solubility in common organic solvents as well as polar aprotic solvents. They undergo a curing reaction at around 350 $^{circ}C$ and show a 50-60${\%}$ of residual weight at 500 $^{circ}C$. The enhanced thermal stabilities were due to the intramolecular cyclization or intermolecular cross-linking reaction of the dicyanovinyl group incorporated into polyester by copolymerization.