Oleic Acid → CID 521661

HRID 493517

반응식

HRID 493517 반응식
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>ClCCl>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

3

반응물 1

HCID 445639Oleic Acid

생성물 1

HCID 521661CID 521661수율 42%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In the 1990s, it was demonstrated that homogeneous ruthenium-based catalysts were effective in catalyzing olefin metathesis; moreover, these catalysts, in contrast to the tungsten and rhenium catalysts, often tolerate functionally substituted alkenes (Grubbs, R. H., Handbook of Metathesis, Wiley-Vch, Verlag GmbH & Co. KGaA, Weinheim (2003)). Such ruthenium-based catalysts have been used to prepare α,ω-dicarboxylate esters via metathetic routes. For example, a two-step process was reported using Grubbs catalysts to prepare long-chain unsaturated α,ω-dicarboxylate methyl esters (Warwel, S., et al., Polym. Sci. Part A: Polym. Chem., 39: 1601-1609 (2001)). Cross-metathesis of monounsaturated carboxylic acid methyl esters with ethylene in the presence of the first generation catalyst 1 (FIG. 1) in solution initially gave terminally unsaturated monocarboxylate methyl esters. The resulting terminal monounsaturated esters then underwent self-metathesis in the presence of catalyst 1 to give long-chain α,ω-dicarboxylic acid methyl esters with an overall yield between 38-40% (Warwel, S., et al., Polym. Sci. Part A: Polym. Chem., 39: 1601-1609 (2001); Warwel, S., et al., Ind. Crops & Prod., 20: 301-309 (2004); Warwel, S., et al., Macromol. Chem. Phys., 202: 1114-1121 (2001); Warwel, S., et al., Macromol. Chem. Phys., 202: 849-855 (2001); Warwel, S., et al., Chemosphere, 43: 39-48 (2001)). Self-metathesis of methyl oleate in dichloromethane was reported using the second generation Grubbs catalyst 2 (FIG. 1) and gave the long chain α,ω-dicarboxylic methyl ester 5a (FIG. 2, Eq. 1) in ˜45% conversion (Dinger, M. B., and J. C. Mol, et al., Adv. Synth. Catal., 344: 671-677 (2002)). The self-metathesis of oleic acid in the presence of Cl2(PCy3)2Ru=CH—CH═CPh2 in dichloromethane solution was reported to give 1,18-octadec-9-enedioic acid (5b) and octadec-9-ene (4) in 42% yield (U.S. Pat. No. 5,728,917). However, this process gave low conversion (about 50%) of monounsaturated fatty acids and low yields of dicarboxylic acids. In addition, the reaction was performed in a solvent, dichloromethane, which is an environmental concern.

출처 및 근거

ORD 기록
ord-f1597adc717b4ef0bf0157204161c27e
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534917B1

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