Methods of preparing disaccharide and trisaccharide C6-C12...

Details Methods of preparing disaccharide and trisaccharide C6-C12... Methods of preparing disaccharide and trisaccharide C6-C12...

2001-08-20

2003-12-23

Wilson, James O. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S001110, C536S123130

Reexamination Certificate

active

06667397

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to novel processes for preparing disaccharide or trisaccharide C
6
-C
12
fatty acid esters having high i-content and materials prepared therefrom. The invention also relates to processes for preparing high a-content cellobiose C
6
-C
2
fatty acid esters and materials prepared therefrom.
BACKGROUND OF THE INVENTION
Highly substituted fatty acid esters of disaccharide and trisaccharides are useful materials. These materials can form discotic columnar liquid crystals. They may also serve as thickeners, plasticizers, and rheology modifiers.
Cellobiose alkanoates have unique physical properties. It is known that the &agr;-anomer form of the cellobiose ester generally forms more stable mesophases than does the &bgr;-anomer. Takada and coworkers describe the preparation of high a-content cellobiose octanonanoate (“CBON”). (Takada, A.; Ide, N.; Fukuda, T.; Miyamoto, T.
Liq. Crystals
1995, 19, 441-448). This paper describes in limited detail a method to produce both high alpha content and high beta content cellobiose octanonanoate and other fatty acid esters.
There has not been described an efficient process to prepare cellobiose fatty acid esters having a high a-content. A primary drawback in the prior art methods is the need for extensive processing of the product to obtain sufficiently high purity of the disaccaharide and trisaccharide fatty acid esters directly from the esterification reaction. Those skilled in the art would recognize that further enrichments in the purity of the product (alpha content) can be obtained by additional recrystallization through any number of standard methods. One of skill in the art will recognize that repeated recrystallization can add considerable expense to the production and can greatly reduce the product yield, thus making the process impractical for an industrial scale. Therefore, it would be highly desirable to develop a process to prepare high purity disaccharide and monosaccharide fatty acid esters wherein such materials may be utilized as prepared from an esterification reaction without the need for purification. Moreover, it would be highly desirable to develop processes wherein novel disaccharide and trisaccharide fatty acid esters are prepared.
BRIEF SUMMARY OF THE INVENTION
This invention relates to novel processes for preparing disaccharide or trisaccharide C
6
-C
12
fatty acid esters having a high &agr;-content and materials prepared therefrom. The invention also relates to processes for preparing high &agr;-content cellobiose C
6
-C
12
fatty acid esters and materials prepared therefrom.
Additional advantages of the invention will be set forth in part in the detailed description, which follows, and in part will be obvious from the description, or may be learned by practice of the invention. The advantages of the invention will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory aspects of the invention, and are not restrictive of the invention, as claimed.


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Takada, A. et al “Discotic columnar liquid crystals in oligosaccharide derivatives III. Anomeric effects on the thermomesomorphic properties of cellobiose octa-alkanoates”, Liquid Crystals, 1995, vol. 19, No. 4, pp 441-448.*
Amelung et al., “Determination of Neutral and Acidic Sugars in Soil by Capillary Gas-Liquid Chromatography after Trifluoroacetic Acid Hydrolysis,”Soil Biol. Biochem., 28(12):1631-1639 (1996).
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Collins et al., “Monosaccharides Their Chemistry and Their Roles in Natural Products,” Wiley & Sons, 362-363 (1995).
Debenham et al., “Two New Orthogonal Amine-Protecting Groups That Can be Cleaved under Mild or Neutral Conditons,”J. Am. Chem. Soc., 117:3302-3303 (1995).
Fan et al., “Comparison of Acid Hydrolytic Conditions for Asn-Linked Oligosaccharides,”Anal. Biochem., 219(2):375-378 (1994) (Abstract).
Hamalainen et al., “Fibrous Cellulose Esters by Trifluoroacetic Anhydride Method,”Text. Research Jour., 27:168 (1957).
Hudson et al., “A Comparison of the Optical Rotatory Powers of the Alpha and Beta Forms of Certain Acetylated Derivatives of Glucose,”J. Am. Chem . Soc., 37:1264-1270 (1915).
Morooka et al., “Dielectric Properties of Cellulose Acylates,”J. Appl. Polym. Sci., 29:3981-3990 (1984).
Takada et al., “Discotic Columnar Liquid Crystals in Oligosaccharide Derivatives III. Anomeric Effects on the Thermo-Mesomorphic Properties of Cellobiose Octa-alkanoates,”Liquid Crystals, 19(4): 441-448 (1995).
Takada et al., “Chain-Length Dependence of the Mesomorphic Properties of Fully Decanoated Cellulose and Cellooligosaccharides,”Macromolecules, 27:1651-1653 (1994).
Takada et al., “Columnar Liquid Crystals in Oligosaccharide Derivatives II. Two Types of Discotic Columnar Liquid-Crystalline Phase of Cellobiose Alkanoates,”Liquid Crystals, 12(2):337-345 (1992).
Takada et al., “Columnar Liquid Crystals in Oligosaccharide Derivatives I. Discotic Columnar Liquid Crystals in Cellobiose Octadecanoate and Cellotriose Hendecadecanoate,”Liquid Crystals, 9(2):221-228 (1991).
Takada et al., “Preparation of Cellobiose Octa(n-alkanoate)s and Their Thermal Properties,”Bull. Inst. Chem. Res., 69(2):77-83 (1991).

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