Preparations and reactions of alkyl ethers of some aldohexoses

Urata, Kouichi; Yano, Shinji; Takaishi, Naotake

doi:10.1007/bf02635782

Cited by 5 publications

(4 citation statements)

References 9 publications

(3 reference statements)

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“…The thus-obtained O-alkylated cyclic and linear monosaccharides, which both contained di-O-isopropylidene groups, were changed to corresponding O-alkyl ether compounds by acidic hydrolysis. These O-alkylated cyclic or linear monosaccharides were useful as nonionic surfactants derived from natural resources (63,64).…”

Section: Present State and Future Potential Of Ptc In Oleochemistrymentioning

confidence: 99%

Applications of phase‐transfer catalytic reactions to fatty acids and their derivatives: Present state and future potential

Urata

Takaishi

1996

J Americ Oil Chem Soc

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Phase-transfer catalysts (PTC), which accelerate reactions between liquid(organic)-Iiquid(water) and liquidsolid heterogeneous states, have been investigated and developed. Several processes with PTC have succeeded in industrial processes involving fatty acids and their derivatives. For example, preparation of fatty alkyl glycidyl ethers, from which fatty alkyl glyceryl ethers and their derivatives can be obtained, has been carried out with PTC. However, some problems remain to be solved. For example, preparation of the fatty alkyl glycidyl ether by a PTC reaction was considered, but typical problems to be solved included: (i) how to reuse or recover the catalysts; (ii) how to control the heterogeneous reaction without obstacles to produce useful chemical materials; (iii) how to satisfy the environmental requirements for the catalysts; and (iv) are there more effective catalysts? We address these problems based on our own experiences with phase-transfer catalytic Williamson ether syntheses of fatty alkyl glycidyl ethers. Moreover, we describe recent developments in phase-transfer catalytic reactions related to oleochemistry, such as transition metal-catalyzed reactions of long-chain olefins in liquid(organic)-Iiquid(water) or liquid-solid heterogeneous states. Based on these results, we have considered the potential of PTC as a synthetic tool in oleochemistry. JAOCS 73, 831-839 (1996). KEY WORDS:Fatty acid derivatives, fatty alkyl glycidyl ether, phase-transfer catalyst, quarts, quaternary ammonium salts, two-phase reaction, Williamson ether synthesis.

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Section: Present State and Future Potential Of Ptc In Oleochemistrymentioning

confidence: 99%

Applications of phase‐transfer catalytic reactions to fatty acids and their derivatives: Present state and future potential

Urata

Takaishi

1996

J Americ Oil Chem Soc

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“…In such cases, it is possible to remove one of the O-isopropylidene groups selectively. Selective removal of only one protective group has been reported for the reactions of some aldohexoses, such as D-glucose (13,14) and D-mannitol (14). After selective removal of the protective group, residual OH groups can undergo acylation, alkylation, amination, oxidation.…”

Section: Types Of Protecting Groups and Related Reactionsmentioning

confidence: 98%

“…After selective removal of the protective group, residual OH groups can undergo acylation, alkylation, amination, oxidation. This method is useful for introducing different kinds of alkyl/acyl chains into a carbohydrate skeleton (13).…”

Section: Types Of Protecting Groups and Related Reactionsmentioning

confidence: 99%

Applications of protecting groups in the synthesis of surfactants, lipids, and related compounds

Urata

Takaishi

1998

J Surfact & Detergents

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Several types of alkyl ether lipids were prepared in high yield and high purity using protecting groups such as 1,3-dioxolane compounds or allyl ethers. We also succeeded in the industrial production of alkyl glyceryl ethers using the reaction of alkyl glycidyl ethers with acetone to give 1,3-dioxolane compounds, from which the desired alkyl glyceryl ethers were obtained in high quantities. 1,3-Dioxolane (ketal) compounds based on acetone were used in the enzymatic preparation of monoglyceride on an industrial scale. On the basis of these protecting groups, we extended our studies concerning both the preparations and properties of novel polyol ether compounds, beginning with alkyl glycidyl ethers. Another typical property of surfactants containing 1,3-dioxolane units and acetal is degradability under acidic conditions. Several types of destructible/cleavable surfactants based on polyols, such as carbohydrates and polyethyleneglycol, were prepared. As for natural products containing polyol skeletons, much attention has been paid to their molecular design, in which protecting groups such as 1,3-dioxolane compounds or allyl ether have contributed to synthetic strategies. JSD 1, 73-82 (1998).

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“…However, concentrations and yields are still too low to make this process attractive for industrial scale‐up. For instance, butyl glucoside has been obtained with a yield less than 40% and a concentration less than 10 g/L (9, 11), while on industrial scales, the yield obtained by the chemical way can exceed 90% with a concentration of more than 90 g/L (12 − 14). It is therefore necessary to improve the performance of the enzymatic process to suggest its use at industrial scales.…”

Section: Introductionmentioning

confidence: 99%

Optimization of the Enzymatic Synthesis of Butyl Glucoside Using Response Surface Methodology

1998

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Enzymatic synthesis of butyl glucoside by beta-glucosidase from bitter almonds was optimized using response surface methodology (RSM). Empirical models were developed to describe relationships between the operating variables (temperature, water/butanol volume ratio, glucose concentration, enzyme concentration) and responses (butyl glucoside concentration, conversion yield). Statistical analysis indicated that the four factors had significant effects on the butyl glucoside synthesis. Optimal concentration (41.6 g/L) was reached when the operating conditions were temperature (44.7 degreesC), water/butanol volume ratio (17.6%), glucose concentration (199.2 g/L), and enzyme concentration (2.5 g/L). Good agreement between predicted and measured data at the predicted optimal conditions confirmed the usefulness of the model. Synthesis at a laboratory pilot scale was successful.

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Preparations and reactions of alkyl ethers of some aldohexoses

Cited by 5 publications

References 9 publications

Applications of phase‐transfer catalytic reactions to fatty acids and their derivatives: Present state and future potential

Applications of phase‐transfer catalytic reactions to fatty acids and their derivatives: Present state and future potential

Applications of protecting groups in the synthesis of surfactants, lipids, and related compounds

Optimization of the Enzymatic Synthesis of Butyl Glucoside Using Response Surface Methodology

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