Sugar – starch – and carbohydrates – Processes – Carbohydrate manufacture and refining
Reexamination Certificate
2002-12-30
2004-08-10
Brunsman, David (Department: 1755)
Sugar, starch, and carbohydrates
Processes
Carbohydrate manufacture and refining
C127S040000, C536S127000, C536S128000
Reexamination Certificate
active
06773512
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a chromatographic separation method of separating carbohydrates, especially sugars, from a mixture including the same. The mixture to be treated in accordance with the present invention is typically a biomass-derived solution including carbohydrates/sugars. Especially, the invention provides a chromatographic separation method of recovering mannose with high purity from biomass-derived solutions, such as spent sulphite pulping liquors. Mannose can be recovered in a crystalline form or in the form of a solution. The claimed process of recovering mannose is based on the use of a combination of a Ba
2+
form resin and a resin in other than Ba
2+
form as the separation resin, whereafter mannose is crystallized, if desired. In connection with the separation process of the invention, xylose and arabinose products can also be obtained as by-products, depending on the composition of the starting biomass-derived solution.
Mannose is useful e.g. for various pharmaceutical applications. It can be used as a starting material or raw material for various pharmaceutical products. Mannose is also therapeutically useful in the treatment of urine infections and intravenous inflammation conditions. In food technology, mannose is useful e.g. for so-called Positech applications (GMO-testing of food products).
Mannose is also useful as the raw material for the production of mannitol, which has various pharmaceutical applications.
Mannose can be recovered from wood resources, where mannose is present as a mixture with other carbohydrates and lignin components. In wood and other plant-based material, mannose typically occurs in polymeric form, such as hemicellulose, most frequently as a heteropolymer with glucose and/or galactose in glucomannans, galactoglucomannans and galactomannans. Spent liquors obtained from conifer wood-pulping processes are especially rich in mannose. Mannose has also been recovered from vegetable ivory nuts and specific seaweeds.
The recovery of mannose with high purity from plant-based material has presented a problem in the state of the art.
Jones, J. K. N & Wall, R. A. (Canadian Journal of Organic Chemistry 38 (1960), pp. 2290 to 2294) have described a process for the separation of sugars from synthetic sugar mixtures and plant extracts using ion-exchange resins. The process relates to the separation of monosaccharide mixtures, including D-mannose and D-mannitol, using neutral salt forms of sulphonic acid type ion-exchange resins. The resin Dowex 50W X8 in Ba
2+
form has been used as the separation resin.
Larsson, L. I & Samuelsson, O. (Acta Chemica Scandinavica 19 (1965), pp. 1357 to 1364) describe an automatic procedure for the separation of monosaccharides present in wood hydrolysates using ion exchange resins. The separation of 16 monosaccharides, including D-mannose, has been studied by partition chromatography on strongly basic anion exchange resins in the sulphate form using ethanol as the eluant.
Furthermore, the utilization of ion exchangers for the isolation of monosaccharides has been studied with the aim to examine the behaviour of sugars on columns containing a bisulfite saturated resin. For example, an anion exchanger (Amberlite IRA-400) in the bisulphite form has been used to separate fructose, glucose and mannose. As a practical result of this study, an improved method for the determination of reducing sugars in sulphite waste liquor is proposed.
The interactions occurring between aluminium oxide and aqueous solutions of monosaccharides, including D-mannose have also been studied. It is suggested that by proper choice of alumina, separation of sugars can be easily and quickly achieved on a preparative as well as analytical scale.
It is also known to recover mannose from various sources through mannose derivatives. Fujita, T & Sato, T in Bull. Chem. Soc. Japan 33 (1960) 353 disclose the recovery of D-mannose through N-phenyl-D-mannopyranosylamine. It is recited that N-phenyl-D-mannopyranosylamine is so stable and insoluble in water that it was recommended for the isolation of D-mannose even from very impure raw materials.
Herrick, F. W., Casebier, R. L., Hamilton, J. K. & Wilson, J. D. (“Mannose chemicals”, Applied Polymer Symposium No. 28 (1975), pp. 93 to 108) disclose a study relating to the development of an economic process for recovering mannose or its derivatives from wood resources, such as a spent sulphite liquor, where mannose is a major component of mixtures containing other carbohydrates and lignin fragments. The main achievement of this work was the development of processes for recovering sodium mannose bisulphite and methyl mannoside from several raw materials. Processes were developed for recovering mannose from crude mixtures via two routes: (1) formation of the sodium bisulphite adducts of monomeric wood sugar mixtures, crystallization and separation of sodium mannose bisulphite and regeneration of mannose from this intermediate, and (2) anhydrous methanolysis concurrent with glycosidation of crude mixed-sugar polymers or monomers, crystallization and separation of methyl &agr;-D mannoside and regeneration of mannose from this intermediate. These procedures for recovering mannose have the drawback that they are very cumbersome to carry out in practice.
Sinner, M, Simatupang, M. H. & Dietrichs, H. H. (“Automated Quantitative Analysis of Wood Carbohydrates by Borate Complex Ion Exchange Cromatography”, Wood Science and Technology, 1975, pp. 307 to 322) describe a simple automated analytical method for the separation and quantitative determination of sugars from acidic and enzymatic hydrolysates of wood polysaccharides via borate complex ion exchange chromatography. The sugars separated in this way include mannose, fructose, arabinose, galactose, xylose, glucose and disaccharides like xylobiose, cellobiose and sucrose.
GB 1 540 556 (ICI Americas, publ. Feb. 14, 1979) relates to a method of separating mannose from glucose present in aqueous solutions. The starting mixture of glucose and mannose is typically obtained by epimerization of glucose in an aqueous solution. The separation of mannose from glucose is typically carried out using a cation exchange resin in the form of an alkaline earth metal salt, such as in Ca
2+
, Sr
2+
or Ba
2+
form. The cation exchange resin is preferably a strongly acid cation exchange resin, typically a resin based on styrene divinylbenzene.
The separation of sugars from lignosulphonates has been described by Hassi, R., Tikka, P. & Sjöström, E. (“Recovery of Lignosulphonates and Sugars from Spent Sulphite Liquors by Ion Exclusion Chromatography, 1982 International Sulfite Pulping Conference, Sheraton Centre Hotel, Toronto, Ontario, October 20-22, pp. 165 to 170). Ion exclusion chromatography on a strongly acid cation exchange resin has been applied to the fractionation of lignosulphonates and sugars, including mannose, present in a spent sulphite liquor. The resin used in the tests was a strongly acid gel-type polystyrene cation exchange resin (Amberlite IR-120, Ca
2+
form). It is proposed that the sugar fraction might be used as a raw material source for mannitol production.
Finnish Patent 78734 (Suomen Sokeri Oy, publ. Apr. 5, 1987) relates to a multi-step process of separating sugars and lignosulphonates from a spent sulphite pulping liquor. This process comprises introducing a spent sulphite pulping liquor into a chromatographic column including a separation resin in a metal salt form, typically a strongly acid cation exchange resin in a Ca
2+
form, eluting the column with water to recover a fraction rich in lignosulphonates and a fraction rich in sugars, introducing the fraction rich in sugars thus obtained into another chromatographic column including a separation resin in a monovalent metal salt form, typically in Na
+
form. A sugar fraction free from lignosulphonates is obtained.
WO 96/27029 (Xyrofin Oy, publ. Sep. 6, 1996) relates to a method of recovering an organic compound, such as sugars, fro
Ennelin Anu
Heikkilä Heikki
Jumppanen Juho
Kaira Miikka
Nurmi Juha
Brunsman David
Danisco Sweeteners Oy
Scully Scott Murphy & Presser
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