Polycondensation of sugars in presence of water using microreactors

Abstract

The invention relates to a polysaccharide and a method for preparing a polysaccharide. In particular, the present invention relates to polysaccharides having at least the desired physical properties in food and beverage products. In particular, the present invention relates to a method of preparing polysaccharides having at least physical properties required in food and beverage products.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of European Application No. 22190222.4 filed on August 12, 2022, which is incorporated herein by reference in its entirety. Technical Field

[0003] The present invention relates to polysaccharides and methods of preparing polysaccharides. In particular, the present invention relates to polysaccharides having physical properties that are at least desirable in food and beverage products. In particular, the present invention relates to methods of preparing polysaccharides having physical properties that are at least desirable in food and beverage products. Background Art

[0004] Carbohydrates are present in a range of food and beverage products, such as processed cereals, soft drinks, bread, beans, potatoes, corn and pasta. The carbohydrates present in food and beverage products have various forms, of which sugar, fiber and starch are the most common. The fiber found in food products is commonly referred to as dietary fiber, which is present in, but not limited to, vegetables, fruits, whole grains and beans. Dietary fiber is the indigestible part of food and beverage derived from plants, and usually passes through the digestive system relatively intact and leaves the body of the consumer.

[0005] Dietary fiber can be divided into two forms: soluble dietary fiber and insoluble dietary fiber. Most food and beverage products (especially those derived from plants) contain different amounts of soluble dietary fiber and insoluble dietary fiber. Soluble dietary fiber dissolves in water and can form a gelatinous material. Examples of fruits, cereals and vegetables containing soluble dietary fiber include but are not limited to oats, peas, beans, apples, citrus fruits, carrots and barley. Insoluble dietary fiber is traditionally used in food and beverage products to provide desired characteristics, such as nutrition, texture and / or mouthfeel. Insoluble dietary fiber promotes the movement of materials in the digestive system of consumers and increases stool volume. Examples of food and beverage products containing insoluble dietary fiber include but are not limited to whole wheat flour, wheat bran, nuts, beans and vegetables, such as broccoli, mung beans and potatoes.

[0006] There is interest in developing ingredients suitable for food products, wherein the ingredients increase the dietary fiber content or reduce the caloric content of food. These ingredients can also have some health benefits, particularly in view of the worldwide obesity epidemic. Obesity is an important risk factor for diseases (such as type 2 diabetes and cardiovascular disease), and they have been the main cause of death in many countries. Therefore, it is necessary to increase the dietary fiber content or reduce the caloric content of food. Soluble dietary fiber can be used to change the texture, thickness, mouthfeel, body or other physical properties of food or beverage products. The example of soluble dietary fiber includes polysaccharides, such as polydextrose and resistant dextrin.

[0007] Typically, polydextrose is formed by the polymerization of sugar monomers. The resulting polydextrose contains highly branched polymers that are difficult to digest by human enzymes: polydextrose is only partially metabolized by the microbial community in the human intestinal tract. Therefore, polydextrose is not digestible by the human body, or is only digestible by the human body to a limited extent. Since polydextrose is not digested in the digestive system, polydextrose in products used in food and beverage products is interesting.

[0008] Typically, resistant dextrins are formed by polymerization of sugar monomers. Resistant dextrins are short-chain glucose polymers that are usually obtained by high-temperature acidification of starch. In addition to the α-1,4 and α-1,6 glycosidic bonds present in starch, the resulting resistant dextrins also contain α-1,2 and α-1,3 glycosidic bonds. Resistant dextrins also contain reducing ends that may contain β-1,6 glycosidic bonds. Since α-1,2, α-1,3 and α-1,6 glycosidic bonds cannot be broken down by various digestive enzymes in the human body, they cannot be digested and absorbed by the small intestine after entering the human digestive tract. Therefore, resistant dextrins cannot be digested by the human body, or are only digested by the human body to a limited extent. Since resistant dextrins are not digested in the digestive system, resistant fibers used in products in food and beverage products are of interest. Examples of resistant dextrins used in food and beverage products are described in WO2013015890A1, US10988550B2 and EP3409693B1.

[0009] One reason why soluble dietary fiber is paid attention to by food and beverage industry is that they can be used for increasing dietary fiber content and / or reducing sugar and caloric content of food or beverage. These changes are very important for the health benefits derived from the obtained food or beverage products. For example, because soluble dietary fiber is not absorbed by the small intestine, soluble dietary fiber can enter the large intestine and be used as a nutrient by various probiotics to realize the various physiological functions of dietary fiber. The second example is that because soluble dietary fiber is not absorbed, soluble dietary fiber can also be used for producing satiety, so soluble dietary fiber can be used as a good matrix material in obese people's food products. The third example is that soluble dietary fiber can also be used for replacing products with higher caloric content in food and beverage products, such as food and beverage products containing high levels of sugar (such as sucrose).

[0010] There is a continuing need for improved polysaccharides that can be used in food and / or beverage products.

[0011] Traditionally, polysaccharides, such as polydextrose or resistant dextrins, are produced by the polycondensation of glucose in a continuous stirred tank reactor (CSTR). Typically, glucose is provided in an aqueous form. A disadvantage of the conventional method is that before the actual polycondensation occurs, most of the water needs to be removed by vacuum distillation, which occurs at a temperature of 110°C to 130°C, preferably 120°C. This step alone can take one to two hours to complete at 120°C before the polycondensation can be initiated by adding a catalyst. Together with the catalyst addition, the temperature is raised to a temperature of 145°C or above. Therefore, there is great interest in improving the method for producing polysaccharides.

[0012] One way to improve the process of producing polysaccharides is to use a microreactor, as described in WO2011091962A1. The method requires the following steps:

[0013] 1. Provide a dry blend of sugars such as glucose or dextrose (in the production of polydextrose, sorbitol and citric acid are also provided);

[0014] 2. Mix the dry blend from step 1 with water at 80°C to obtain a solution with a solid content of 80 wt.%;

[0015] 3. The mixture from step 2 was pumped through the first microreactor at a rate of 20 ml / min, wherein the mixture reached a temperature of 200° C.;

[0016] 4. Spraying the product from the first microreactor into a collection chamber for drying by flash evaporation;

[0017] 5. The product from step 4 was pumped through a second microreactor at a rate of 20 ml / min, wherein the mixture was brought to a temperature of 200° C.; and

[0018] 6. The product from step 5 was diluted with water to 50 wt% solids content, wherein the product contained 80 wt% polymeric product.

[0019] The conventionally used microreactors are usually stacks of machined or etched metal foils, which are fused into a block by diffusion welding. The foils contain parallel channels that are either straight or curved. The shape of the channels can be square, rectangular, circular, elliptical or semi-elliptical. Depending on the design of the foils, a lateral or countercurrent flow of the medium within the microreactor can be achieved.

[0020] There is a continuing need for improved methods for producing polysaccharides that can be used in food and / or beverage products. Summary of the invention

[0021] The present invention relates to polysaccharides and methods of preparing polysaccharides. In particular, the present invention relates to polysaccharides having physical properties that are at least desirable in food and beverage products. In particular, the present invention relates to methods of preparing polysaccharides having physical properties that are at least desirable in food and beverage products.

[0022] Representative features of the invention are listed in the following clauses, which may exist alone or in any combination with one or more features disclosed in the text of this specification.

[0023] The present invention is described in the following clauses:

[0024] 1. A polysaccharide, comprising:

[0025] 5 to 35% by weight of 1,2-glycosidic bonds and 1,3-glycosidic bonds,

[0026] 25 to 35 wt. % of 1,4-glycosidic bonds, and

[0027] 35 to 45% by weight of 1,6-glycosidic bonds,

[0028] wherein the polysaccharide has a DP1 and DP2 content, wherein DP1 and DP2 are present in a combined weight % of greater than 15 wt % to 25 wt %.

[0029] 2. The polysaccharide according to clause 1, wherein DP1 and DP2 are present in a combined weight % of greater than 15 wt% to 25 wt%, or greater than 17.5 wt% to 22.5 wt%, or at 20 wt%, wherein the weight % are measured on a dry basis.

[0030] 3. The polysaccharide according to clause 1 or clause 2, wherein the polysaccharide has a DP1+ content of 90 wt% to 99 wt%, or 92 wt% to 96 wt%, or 93.6 wt%, wherein the wt% are measured on a dry basis.

[0031] 4. The polysaccharide according to any one of clauses 1 to 3, wherein the polysaccharide has a DP1 content of 2 wt% to 5 wt%, or 3 wt% to 4 wt%, or 3.5 wt%, wherein the wt% are measured on a dry basis.

[0032] 5. The polysaccharide of any one of clauses 1 to 4, wherein the polysaccharide comprises 1 wt% to 4 wt%, or 2 wt% to 3 wt%, or 2.4 wt% 1,6-anhydrodextrose, wherein the wt% are measured on a dry basis.

[0033] 6. The polysaccharide according to any one of clauses 1 to 5, wherein the polysaccharide has a DPn content, wherein n is equal to 8 or more, wherein DPn is present at 55 wt% or less, or 50 wt% or less, wherein the wt% is measured on a dry basis.

[0034] 7. The polysaccharide according to any one of clauses 1 to 6, wherein the polysaccharide has a DP3 to DP7 content, wherein the DP3 to DP7 are present in a combined weight % of 28 wt% to 45 wt%, or 29 wt% to 35 wt%.

[0035] 8. The polysaccharide according to any one of clauses 1 to 7, wherein the polysaccharide comprises or consists of glucose monomers.

[0036] 9. The polysaccharide according to claim 8, wherein the polysaccharide comprises 50 to 100 wt% glucose monomers, or 60 to 100 wt% glucose monomers, or 70 to 100 wt% glucose monomers, or 80 to 100 wt% glucose monomers, or 90 to 100 wt% glucose monomers, or 100 wt% glucose monomers.

[0037] 10. The polysaccharide of any one of clauses 1 to 9, wherein the polysaccharide has a fiber content of 70% to 85% by weight, or 75% to 80% by weight, or 77% by weight.

[0038] 11. The polysaccharide of any one of clauses 1 to 10, wherein the polysaccharide has a 5-hydroxymethylfurfural (HMF) content of less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2.5 ppm, or 2 ppm.

[0039] 12. The polysaccharide of any one of clauses 1 to 11, wherein the polysaccharide has a furfural content of less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2.5 ppm, or 2 ppm.

[0040] 13. The polysaccharide of any one of clauses 1 to 12, wherein the polysaccharide has a Gardner color value of less than 2, or less than 1.5, or less than 1.25, or less than 1.1, or less than 1.05, or less than 1.0, or less than 0.9, or preferably 0.8.

[0041] 14. The polysaccharide according to any one of clauses 1 to 13, wherein the polysaccharide has a pH of from 4 to 6, or from 4.5 to 5.5, or 5.1.

[0042] 15. The polysaccharide according to any one of clauses 1 to 14, wherein the polysaccharide is polydextrose and / or resistant dextrin.

[0043] 16. A composition comprising:

[0044] The polysaccharide according to any one of clauses 1 to 15; and

[0045] water.

[0046] 17. A composition according to clause 16, wherein the composition comprises 40% to 90% or 45% to 80% dry solids by weight.

[0047] 18. A composition according to clause 17, wherein the dry solid comprises or consists of the polysaccharide.

[0048] 19. A method for preparing a polysaccharide according to any one of clauses 1 to 15, the method comprising:

[0049] (a) providing a sugar feed comprising glucose monomers and / or glucose oligomers;

[0050] (b) providing at least one acid catalyst;

[0051] (c) providing a microreactor comprising one or more flow guiding elements; and

[0052] (d) passing the sugar feed through the microreactor in the presence of the acid catalyst until at least 80 wt % of the glucose monomers and / or glucose oligomers in the sugar feed have reacted to form polysaccharides having a DPn content, wherein n is at least 3.

[0053] 20. The method according to clause 19, wherein the sugar feed comprises a dry matter content of less than 80 wt%, or less than 70 wt%, or less than 60 wt%.

[0054] 21. A process according to clause 20, wherein the remainder wt% of the sugar feed is water.

[0055] 22. A method according to clause 20 or clause 21, wherein the dry matter content comprises at least 50 wt%, or at least 55 wt%, or at least 60 wt% of the glucose monomers and / or glucose oligomers.

[0056] 23. The method according to any one of clauses 20 to 22, wherein the dry matter content comprises:

[0057] Up to 50% by weight, or

[0058] Up to 45%, or up to 40%, by weight, of monosaccharides, disaccharides and oligosaccharides; and

[0060] The monosaccharides, disaccharides and oligosaccharides do not include glucose monomers and / or glucose oligomers.

[0061] 24. A method according to any one of clauses 19 to 23, wherein at least 85 wt%, or at least 90 wt%, or at least 95 wt% of the glucose monomers and / or glucose oligomers in the sugar feed are reacted to form polysaccharides having a DPn content, wherein n is at least 3.

[0062] 25. A method according to any one of clauses 19 to 24, wherein the microreactor is operated at a temperature of 180°C to 250°C, or 190°C to 245°C, or 200°C to 240°C, or 220°C to 235°C, or 220°C.

[0063] 26. A method according to any one of clauses 19 to 25, wherein the microreactor is operated at a pressure of 2 to 25 bar, or 2 to 20 bar, or 2 to 15 bar, or 2 to 10 bar, or 2 to 5 bar, or 2 to 3 bar.

[0064] 27. A method according to any one of clauses 19 to 26, wherein the residence time of the sugar feed in the microreactor is 180 seconds or less, or 120 seconds or less, or 100 seconds or less, or 90 seconds or less, or 80 seconds or less, or 70 seconds or less, or 60 seconds or less, or 50 seconds or less, or at least 5 seconds, or at least 10 seconds, or at least 15 seconds.

[0065] 28. The method according to any one of clauses 19 to 27, wherein the glucose monomers and / or glucose oligomers have a DPn content, wherein n has an average value of 3 to 10.

[0066] 29. The method according to any one of clauses 19 to 28, wherein the glucose monomers and / or glucose oligomers are derived from glucose syrup or maltodextrin.

[0067] 30. The method of clause 29, wherein the glucose syrup has a dextrose equivalent (DE) of 20 or greater.

[0068] 31. The method according to clause 29, wherein the maltodextrin has a dextrose equivalent (DE) of 3 to 20.

[0069] 32. A process according to any one of clauses 19 to 31 wherein the sugar feed comprises a polyol.

[0070] 33. The method according to clause 32, wherein the polyol is any one of glycerol, erythritol, threitol, arabitol, xylitol, ribitol, allitol, altritol, gulitol, dulcitol, mannitol, sorbitol, talitol, maltitol, isomalt, isomalt, lactitol, or a combination thereof.

[0071] 34. The method according to any one of clauses 19 to 33, wherein the acid catalyst is any one of phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof.

[0072] 35. A process according to any one of clauses 32 to 34 wherein the polyol is sorbitol and the acid catalyst is any one of phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof.

[0073] 36. The method according to any one of clauses 32 to 35, wherein the sugar feed comprises the glucose monomers and / or glucose oligomers, the polyol and the acid catalyst in a weight ratio of 85:15:1 to 95:5:1, respectively.

[0074] 37. The method according to any one of clauses 32 to 35, wherein the sugar feed comprises the glucose monomers and / or glucose oligomers, the polyol and the acid catalyst in a weight ratio of 90:10:1 respectively.

[0075] 38. A method according to any one of clauses 19 to 37, wherein the microreactor comprises a plurality of flow-conducting elements; optionally, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49 or 50 flow-conducting elements or more, depending on the size of each flow-conducting element.

[0076] 39. The method according to clause 38, wherein the plurality of flow-guiding elements are arranged as follows: in series; or, in parallel; or, a portion of the plurality is in a first series, a portion of the plurality is in a second series, and the first series and the second series are in parallel.

[0077] 40. A method according to any one of clauses 19 to 39, wherein:

[0078] The flow-guiding element is a device for achieving a defined guidance of a certain volume of fluid flow through a channel-shaped element;

[0079] wherein in the channel-shaped element, the microchannel structure flow-guiding element is arranged to divide the volume flow and to guide the generated fluid flow division;

[0080] The construction is arranged in such a way that the partial flows are guided so that they come into contact alternately with the inner wall of the channel-shaped element and with other partial flows.

[0081] 41. The method according to clause 40, wherein the cross section of the channel-shaped element is designed to be circular, annular, elliptical or rectangular.

[0082] 42. A method according to clause 40 or clause 41, wherein the flow guide element comprises a catalytically active material; optionally,

[0083] Wherein the microchannel structure flow guiding element further comprises a carrier material, and the catalytically active material is supported on the carrier material; optionally,

[0084] The support material is carbon or silicon dioxide.

[0085] 43. A method according to clause 42, wherein the catalytically active material is an acid.

[0086] 44. The method according to clause 43, wherein the acid is any one of phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof.

[0087] 45. The method according to any one of clauses 40 to 44, wherein the microchannel structure guide element comprises a catalytically active material, an anti-corrosion material, an anti-fouling layer or a combination thereof; optionally,

[0088] Wherein the microchannel structure guide element further comprises a carrier material, and the catalytically active material, the anti-corrosion material, the anti-fouling layer or a combination thereof is loaded on the carrier material; optionally,

[0089] The support material is carbon or silicon dioxide.

[0090] 46. ​​The method according to any one of clauses 19 to 45, wherein the method does not comprise a flash drying step.

[0091] 47. A method according to any one of clauses 19 to 46, wherein the method does not comprise a water reduction step.

[0092] 48. The method according to any one of clauses 19 to 47, wherein the method comprises passing the sugar feed through the microreactor once.

[0093] 49. A method according to any one of clauses 19 to 48, wherein the method further comprises one or more of the following steps: chromatography, hydrogenation, filtration (by ultrafiltration or membrane filtration), activated carbon treatment, decolorization, electrolysis, ion exchange resins or a combination thereof.

[0094] 50. A food or beverage product comprising the polysaccharide according to any one of clauses 1 to 15.

[0095] 51. A food or beverage product according to clause 50, wherein the food product is a dairy product; optionally,

[0096] wherein the dairy product is a milk-based beverage; or

[0097] Wherein the food product is a confectionery food product; optionally, wherein the confectionery food product is a gummy candy, a jelly candy, a gelatin candy, a chewing gum or a jelly bean. DETAILED DESCRIPTION

[0098] Embodiments of the present invention are described below with reference to the accompanying drawings. The accompanying drawings illustrate various embodiments of systems, methods, and embodiments of various other aspects of the present disclosure. However, the embodiments of the claims may be embodied in many different forms and should not be construed as limited to the embodiments described herein.

[0099] The words "comprise," "have," "contain," and "include," and other forms thereof, are intended to be equivalent in meaning and to be open ended, in that one or more items following any of these words are not meant to be an exhaustive list of such one or more items, or to be limited to the listed one or more items. It must also be noted that, as used herein and in the appended claims, the singular forms "a / kind," and "the / said" include plural references unless the context clearly indicates otherwise. Although any systems and methods similar or equivalent to the systems and methods described herein can be used in the practice or testing of embodiments of the present disclosure, the preferred systems and methods are now described.

[0100] Listed below are some terms used to describe the present invention:

[0101] "Degree of polymerization" (DP) refers to the number of monomer units in an oligomer. For example,

[0102] DP1 contains one monomer unit, examples of which include but are not limited to fructose or glucose. For another example, DP2 contains two monomer units, examples of which include but are not limited to maltose (which is a glucose polymer of two glucose units).

[0103] "Dextrin" refers to low molecular weight carbohydrates produced by the hydrolysis of starch or glycogen. Low molecular weight carbohydrates are typically a mixture of polymers of D-glucose units linked by α-1,4 or α-1,6 glycosidic bonds. Examples of methods by which dextrins can be produced from starch include, but are not limited to, (a) enzymatic digestion using an enzyme such as amylase; or (b) heating under acidic conditions. Examples of dextrins include, but are not limited to, pyrodextrins, dextrin oligomers, maltodextrins, and cyclodextrins.

[0104] "Dextrose equivalent" refers to the amount of reducing sugars present in a sugar product expressed as a dry basis percentage relative to dextrose.

[0105] "Disaccharide" refers to any substance composed of two monosaccharide molecules (i.e., monosaccharides) linked to each other. Examples of disaccharides include, but are not limited to, sucrose, lactose, and maltose.

[0106] "Fiber" refers to the stringy structures that combine to form animal or plant tissue. Fiber is a type of carbohydrate that cannot be digested by the human body.

[0107] "Flow-guiding element" refers to a thin-walled component installed in a flow channel, for example in a pipe in a tubular heat exchanger. The purpose of the flow-guiding element is to guide the flow in the channel in such a way that the fluid flow is divided into sub-flows and these sub-flows are alternately directed to the walls of the flow channel. By alternately directing, heat exchange processes can take place with the channel walls and / or between the sub-flows. Due to the temperature difference between the fluid and the wall of the flow channel, heat exchange takes place, resulting in heat being transferred through the fluid layer.

[0108] "Food matrix" refers to a physical domain that contains and / or interacts with specific components of a food (e.g., nutrients) to provide functions and behaviors that are different from those exhibited by these components in an isolated or free state.

[0109] "Gardner Colorimetric" refers to a color system designed to provide a yellowness value for a sample. The color system ranges from 0 to 18. For example, 1 is light yellow and 18 is dark brown.

[0110] "Microreactor" refers to a miniaturized reaction vessel manufactured at least in part by a method of microtechnology and precision engineering. The size of the internal structure of the fluid channel (referred to herein as microchannel) of a microreactor can vary significantly, but generally ranges from micrometer to millimeter range, as defined in ISO 10991. Microreactors are most common but not necessarily designed to have a microchannel structure, and are generally manufactured by methods including but not limited to micromachining, precision engineering and 3D printing. These structures contain many channels, and each microchannel is used to convert a small amount of material. It is also possible that a free microstructure shape that does not form a dedicated channel can be manufactured. A free microstructure shape can be manufactured by using 3D printing. Several materials such as silicon, ceramics, glass, metal and polymers can be used to build a microreactor.

[0111] "Monosaccharide" refers to a single sugar consisting of three to seven carbons in a straight chain or cyclic molecule. Examples of monosaccharides include, but are not limited to, glucose, galactose, and fructose.

[0112] "Particle form" refers to a combination of one or more particles having a D10 in the range of 1 μm to 100 μm, a D50 in the range of 1 μm to 150 μm, and a D90 in the range of 1 μm to 300 μm. The particle form may be completely uniform. Alternatively, the particle form is not necessarily completely uniform.

[0113] "Polysaccharide" refers to a polysaccharide comprising at least 5 to 35 wt% 1,2-glycosidic bonds and 1,3-glycosidic bonds, 25 to 35 wt% 1,4-glycosidic bonds, and 35 to 45 wt% 1,6-glycosidic bonds, wherein the polysaccharide has a DP1 and DP2 content, wherein DP1 and DP2 are present in a combined weight % of greater than 15 to 25 wt%.

[0114] "Polydextrose" refers to a carbohydrate comprising a highly branched polymer of dextrose monomeric units. Polydextrose is only partially metabolized by enzymes present in the human digestive system.

[0115] "Repeat length" refers to the distance corresponding to the contact section of the channel wall when the partial flow is directed away from the channel wall of the flow-guiding element after contact. The repeat length corresponds to the section of the channel wall in which the partial flow is in contact with the channel wall. Other examples of repeat lengths are included in EP3334993B1, the disclosure of which is hereby incorporated by reference.

[0116] "Resistant dextrin" refers to dextrins that are resistant or partially resistant to the digestive enzymes present in the small intestine. Resistant dextrins contain α-1,2 and α-1,3 glycosidic bonds in addition to the α-1,4 and α-1,6 glycosidic bonds present in starch, for example. Resistant dextrins also contain β-1,6 glycosidic bonds. α-1,3, α-1,2 and α-1,6 glycosidic bonds cannot be broken down by various digestive enzymes in the human body, thus contributing to enzyme resistance.

[0117] "Weight %" refers to the weight percentage of a component of a composition in grams per 100 grams of the composition. For example, if the resistant dextrin contains 10 weight % DP1, there are 10 g DP1 per 100 g resistant dextrin.

[0118] "Viscosity" refers to the resistance of a fluid (such as a liquid or gas) to change shape.

[0119] Polysaccharides

[0120] The polysaccharides formed according to the presently described methods possess various desirable properties which provide improved polysaccharides for use in food and / or beverage products.

[0121] The polysaccharide comprises 5 to 35 wt% of 1,2-glycosidic bonds and 1,3-glycosidic bonds, 25 to 35 wt% of 1,4-glycosidic bonds and 35 to 45 wt% of 1,6-glycosidic bonds, wherein the wt% is measured on a dry basis. Preferably, the polysaccharide comprises 30 wt% of 1,2-glycosidic bonds and 1,3-glycosidic bonds, 30 wt% of 1,4-glycosidic bonds and 40 wt% of 1,6-glycosidic bonds, wherein the wt% is measured on a dry basis.

[0122] The polysaccharide may have a DP1 and DP2 content, wherein DP1 and DP2 are present in a combined weight % of greater than 15 wt % to 25 wt %, wherein the weight % is measured on a dry basis. More preferably, DP1 and DP2 are present in a combined weight % of greater than 15 wt % to 25 wt %, or greater than 17.5 wt % to 22.5 wt %, or at 20 wt %, wherein the weight % is measured on a dry basis.

[0123] The polysaccharide may have a DP1+ content of 90 wt% to 99 wt%, or 92 wt% to 96 wt%, or 93.6 wt%, wherein the wt% are measured on a dry basis.

[0124] The polysaccharide may have a DP1 content of 2 wt% to 5 wt%, or 3 wt% to 4 wt%, or 3.5 wt%, wherein the wt% are measured on a dry basis.

[0125] The polysaccharide may comprise 1 wt% to 4 wt%, or 2 wt% to 3 wt%, or 2.4 wt% 1,6-anhydrodextrose, wherein the wt% is measured on a dry basis.

[0126] The polysaccharide may have a DPn content, wherein n is equal to 8 or more, wherein the DPn is present at 55 wt% or less, or 50 wt% or less, wherein the wt% is measured on a dry basis.

[0127] The polysaccharide may have a DP3 to DP7 content, wherein the DP3 to DP7 is present in a combined wt % of 28 wt % to 45 wt %, or 29 wt % to 35 wt %, wherein the wt % is measured on a dry basis.

[0128] The polysaccharide comprises glucose monomers or is composed of glucose monomers. Preferably, the polysaccharide comprises 50% to 100% by weight glucose monomers, or 60% to 100% by weight glucose monomers, or 70% to 100% by weight glucose monomers, or 80% to 100% by weight glucose monomers, or 90% to 100% by weight glucose monomers, or 92% to 100% by weight glucose monomers, or 94% to 100% by weight glucose monomers, or 90% to 99.9% by weight glucose monomers, or 90% to 99.8% by weight glucose monomers, or 100% by weight glucose monomers, wherein the % by weight is measured on a dry basis.

[0129] The polysaccharide preferably has a fiber content of 70 to 85 wt%, or 75 to 80 wt%, or 77 wt%.The fiber content is measured using the well-known method AOAC 2009.01.

[0130] The polysaccharide preferably has a 5-hydroxymethylfurfural (HMF) content of less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2.5 ppm, or 2 ppm. The polysaccharide preferably has a furfural content of less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2.5 ppm, or 2 ppm. The 5-hydroxymethylfurfural (HMF) and furfural contents are measured using HPLC equipped with a UV detector.

[0131] The polysaccharide preferably has a Gardner color value of less than 2, or less than 1.5, or less than 1.25, or less than 1.1, or less than 1.05, or less than 1.0, or less than 0.9, or preferably 0.8. Optionally, the Gardner colorimetric value is measured on a UV / VIS spectrophotometer. A dual-beam Zenon fast spectrometer (e.g., 3nh YS6080 desktop spectrometer) can be used to measure the Gardner colorimetric value. The spectrometer measures the percent transmittance of the product and automatically calculates the Gardner colorimetric parameters.

[0132] The polysaccharide preferably has a pH of from 4 to 6, or from 4.5 to 5.5, or 5.1.

[0133] The polysaccharide is preferably polydextrose and / or resistant dextrin.

[0134] Compositions containing polysaccharides

[0135] Another aspect of the invention relates to the polysaccharide in the composition.

[0136] The composition may comprise a polysaccharide and water. Preferably, the composition comprises a polysaccharide as described above. Alternatively, the composition may also be a dry composition of the polysaccharide, comprising less than 10% by weight of water, preferably less than 8% by weight of water, more preferably less than 5% by weight of water.

[0137] The composition may have a dry solids content of 40% to 90% by weight, or 45% to 80% by weight. Preferably, the dry solids content comprises or consists of a polysaccharide as described above under the heading "polysaccharide". Preferably, the dry solids content comprises or consists of a polysaccharide, sorbitol and glucose as described above under the heading "polysaccharide", wherein the sorbitol is present at less than 2% by weight and the glucose is present at less than 4% by weight. Alternatively, the dry solids content comprises or consists of a polysaccharide, glucose and anhydrous glucose as described above under the heading "polysaccharide", wherein the glucose is present at less than 5% by weight and the anhydrous glucose is present at less than 4% by weight.

[0138] Method for producing polysaccharides

[0139] Another aspect of the present invention relates to a method for preparing a polysaccharide. The method for preparing a polysaccharide comprises the following steps:

[0140] (a) providing a sugar feed comprising glucose monomers and / or glucose oligomers;

[0141] (b) providing at least one acid catalyst;

[0142] (c) providing a microreactor comprising one or more flow guiding elements; and

[0143] (d) passing the sugar feed through the microreactor in the presence of an acid catalyst until at least 80 wt % of the glucose monomers and / or glucose oligomers in the sugar feed have reacted to form polysaccharides having a DPn content, wherein n is at least 3.

[0144] The sugar feed may comprise a dry matter content of less than 80 wt%, or less than 70 wt%, or less than 60 wt%.The remaining wt% of the sugar feed is solvent, such as but not limited to water.

[0145] The dry matter content of the sugar feed may comprise less than 50 wt. % of other monosaccharides and oligomers together with glucose and glucose oligomers, such as fructose and / or fructose oligomers.

[0146] The dry matter content of the sugar feed may comprise at least 50 wt%, or at least 55 wt%, or at least 60 wt% glucose and / or glucose oligomers.

[0147] The dry matter of the sugar feed may comprise up to 50 wt%, or up to 45 wt%, or up to 40 wt% of monosaccharides, disaccharides and oligosaccharides, wherein the monosaccharides, disaccharides and oligosaccharides exclude glucose monomers and / or glucose oligomers.

[0148] Glucose monomers are herein understood to mean glucose oligomers having a DPn content, wherein the average value of n is from 3 to 10.

[0149] Glucose monomers and / or glucose oligomers may be derived from glucose syrup. Preferably, glucose syrup has a DE of 20 or greater. Alternatively, glucose monomers and / or glucose oligomers may be derived from maltodextrin. Preferably, maltodextrin has a dextrose equivalent (DE) of 3 to 20.

[0150] Preferably, at least 85 wt%, or at least 90 wt%, or at least 95 wt% of the glucose monomers and / or glucose oligomers in the sugar feed are reacted to form polysaccharides having a DPn content, wherein n is at least 3.

[0151] Preferably, the microreactor is operated at a temperature of 180°C to 250°C, or 190°C to 245°C, or 200°C to 240°C, or 220°C to 235°C, or 220°C.

[0152] Preferably, the microreactor is operated at a pressure of 2 to 25 bar, or 2 to 20 bar, or 2 to 15 bar, or 2 to 10 bar, or 2 to 5 bar, or 2 to 3 bar.

[0153] Preferably, the residence time of the sugar feed in the microreactor is 180 seconds or less, or 120 seconds or less, or 100 seconds or less, or 90 seconds or less, or 80 seconds or less, or 70 seconds or less, or 60 seconds or less, or 50 seconds or less, or at least 5 seconds, or at least 10 seconds, or at least 15 seconds.

[0154] Preferably, the microreactor is operated at a temperature of 220°C, a pressure of 2 to 3 bar and a sugar feed, and the residence time in the microreactor is 70 seconds or less.

[0155] The sugar feed may also include a polyol. Preferably, the polyol is any one of glycerol, erythritol, threitol, arabitol, xylitol, ribitol, allitol, altritol, gulitol, galactitol, mannitol, sorbitol, talitol, maltitol, isomalt, isomalt, lactitol, or a combination thereof. More preferably, the polyol is sorbitol.

[0156] Preferably, the acid catalyst is phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof. Preferably, the acid catalyst is citric acid.

[0157] Preferably, the polyol is sorbitol and the acid is phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof. For the preparation of polydextrose, the polyol is sorbitol and the acid is phosphoric acid and / or citric acid.

[0158] Sugar feed may include glucose monomers and / or glucose oligomers, polyols and acid catalysts. Preferably, sugar feed includes glucose and / or glucose oligomers, polyols and acid catalysts in a weight ratio of 85:15:1 to 95:5:1. Preferably, sugar feed includes glucose and / or glucose oligomers, polyols and acid catalysts in a weight ratio of 90:10:1, respectively.

[0159] Preferably, the microreactor comprises a plurality of flow guiding elements; optionally, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49 or 50 flow guiding elements or more flow guiding elements, depending on the size of each flow guiding element. The flow guiding element may have a repeat length of 6 mm to 10 mm. The number of shunts may be 3, 4 or 5. The microchannel may span 30°, 45° or 60°. Preferably, the plurality of flow-guiding elements are arranged as follows: in series; or, in parallel; or, a portion of the plurality of flow-guiding elements is in a first series, a portion of the plurality of flow-guiding elements is in a second series, and the first series and the second series are in parallel.

[0160] The microreactor can be a microheat exchanger. The microheat exchanger is a cross-flow microheat exchanger, a counter-flow microheat exchanger, a parallel flow microheat exchanger or an electric parallel flow microheat exchanger and / or a microreactor suitable for polycondensation. A cross-flow microheat exchanger is a miniaturized plate heat exchanger in which a single fluid stream is transported in a lateral manner, as disclosed in EP1046867B1. A counter-flow microheat exchanger is a miniaturized plate heat exchanger in which a single fluid stream is transported in such a manner that the inlets and outlets of the two fluids are in opposite directions to each other, and therefore the fluid streams flow relative to each other, which is also described in EP1046867B1. A parallel flow microheat exchanger is a miniaturized plate heat exchanger in which a single fluid stream is transported in such a manner that the inlets and outlets of the two fluids are in the same directions of the device, and therefore the fluid streams flow in parallel, which is described in EP1046867B1. An electrodynamic parallel flow micro heat exchanger is a miniaturized heat exchanger in which the heating or cooling energy is provided by electrical elements (resistance heater cartridges, Peltier elements), such as described in EP1046867B1, EP1402589B1, EP1402589B1, the disclosures of which are hereby incorporated by reference.

[0161] Methods and examples of use of microreactors are further described in WO2011091962 and WO2011098240, the disclosures of which are incorporated herein by reference.

[0162] There are many advantages to using microreactors to prepare resistant dextrins. Compared with large-scale methods, the advantages of microreactors include but are not limited to: large-scale batch methods can be replaced by continuous flow methods, smaller equipment requires less space, requires less material and less energy, shorter response time and enhanced system performance. Therefore, microreactors significantly enhance heat transfer, mass transfer and diffusion flux per unit volume or unit area.

[0163] The flow-guiding element of the microreactor can be produced using 3D printing.Preferably, the flow-guiding element of the microreactor is made of metal, ceramic, plastic, other inorganic materials or a combination thereof.

[0164] The flow-guiding element may comprise a catalytically active material; optionally, wherein the microchannel structure flow-guiding element further comprises a carrier material, the catalytically active material, the anti-corrosion material, the anti-fouling layer or a combination thereof being loaded on the carrier material; optionally, wherein the carrier material is carbon or silicon dioxide. Preferably, the catalytic material is an acid, such as any one of phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof. The flow-guiding element may be one or more devices for realizing the limited guidance of a certain volume of fluid flow through a channel-shaped element, wherein in the channel-shaped element, the microchannel structure flow-guiding element is arranged to divide the volume flow and is used to guide the generated fluid shunt, and wherein the arrangement of the structure is such that the shunt is guided so that they are alternately contacted with the inner wall of the channel-shaped element and other shunts. Preferably, the cross-section of the channel-shaped element is designed to be circular, annular, elliptical or rectangular. Preferably, the flow guide element comprises or consists of a catalytically active material; optionally, the microchannel structure flow guide element further comprises a carrier material, the catalytically active material is supported on the carrier material, optionally, the carrier material is carbon or silicon dioxide. Preferably, the catalytic material is an acid, such as any one of phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof.

[0165] The microchannel structure guide element may comprise a catalytically active material, an anticorrosive material, an antifouling layer or a combination thereof or may be composed of a catalytically active material, an anticorrosive material, an antifouling layer or a combination thereof. Examples of anticorrosive materials include, but are not limited to, zinc layers. Examples of antifouling layers include, but are not limited to, antifouling coatings. Optionally, the microchannel structure guide element further comprises a carrier material loaded with a catalytically active material, an anticorrosive material, an antifouling layer or a combination thereof, and optionally, the carrier material is carbon or silicon dioxide.

[0166] The flow-conducting elements of the microreactor can be fixedly mounted: this ensures permanent contact with the channel walls or other flow dividers at a defined surface.

[0167] Methods of use and examples of fluid directing elements for use with microreactors are further described in EP3334993B1 and EP1525426B1, the disclosures of which are incorporated herein by reference.

[0168] Preferably, the process does not comprise a flash drying step, more preferably, the process does not comprise a water reduction step.

[0169] Preferably, the method comprises passing the sugar feed through the microreactor once.

[0170] Preferably, the process comprises passing the sugar feed through the microreactor once and does not comprise a drying step.

[0171] Preferably, the method further comprises one or more of the following steps: chromatography, hydrogenation, filtration (by ultrafiltration or membrane filtration), activated carbon treatment, decolorization, electrolysis, ion exchange resins or a combination thereof.

[0172] Advantageously, the method for producing polysaccharides can form polysaccharides in which at least 80% by weight of glucose and / or glucose oligomers have reacted by passing the sugar feed through a microreactor once, without the need to include a drying step in the method. Therefore, the method advantageously allows for a more compact reactor design, requiring less equipment (e.g., no reactor or cross-flow thermal separator, cyclone separator, pump and / or second microreactor is required). Costs are therefore reduced.

[0173] Method for producing a composition comprising a polysaccharide

[0174] Another aspect of the present invention relates to a method for preparing a polysaccharide in a composition. The method for preparing a polysaccharide in a composition comprises the following steps:

[0175] (a) providing polysaccharides;

[0176] (b) combining the polysaccharide with water to form a composition.

[0177] Water may be added to the polysaccharide until the composition comprises 1 wt% to 70 wt%, or 3 wt% to 60 wt%, or 5 wt% to 50 wt% polysaccharide.

[0178] Preferably, the composition comprises 40% to 90% by weight, or 45% to 80% by weight dry solids.

[0179] Preferably, at least 80 wt%, or at least 85 wt%, or at least 90 wt%, or at least 95 wt% of the polysaccharide has been polymerized.

[0180] Polysaccharides and / or compositions in food or beverage products

[0181] Another aspect of the present invention relates to polysaccharides in food or beverage products and / or compositions comprising the polysaccharides.

[0182] The polysaccharide and / or the composition comprising the polysaccharide can be used in a food or beverage product. Optionally, the food or beverage product also comprises a filler, such as a sugar alcohol or maltodextrin; a sweetener, such as sucrose, HFC, fructose and / or a high intensity sweetener.

[0183] The polysaccharide and / or composition can be used as a tenderizer or texturizer (e.g., to increase the crispness of the product), a humectant (e.g., to extend the shelf life of the product and / or produce a soft or moist texture), an agent for reducing water activity, an agent for replacing egg liquid, an agent for improving the gloss of the product, an agent for replacing fat in the product, an agent for changing the gelatinization temperature of flour starch, an agent for changing the texture of the product and / or an agent for enhancing the browning of the product in food or beverage products.

[0184] This polysaccharide and / or composition can be present in food or beverage product, or be present in the phase of food or beverage product, and the phase of this food or beverage product or food or beverage product comprises at least 10 % by weight or at least 20 % by weight or at least 30 % by weight or at least 50 % by weight of water.This polysaccharide and / or composition can also be present in food or beverage product, or be present in the phase of food or beverage product, and the phase of this food or beverage product or this food or beverage product is the dry mixture adding liquid (such as water) thereto.The example of dry mixture includes but is not limited to the powder for fruit beverage, protein beverage, meal replacement, milk, milk modifier, batter, pudding, soup, gravy and sauce.

[0185] The polysaccharide and / or composition can be incorporated into a confectionery food product, including but not limited to chocolate. Examples of chocolates into which the resistant dextrin can be incorporated include but are not limited to milk chocolate, bittersweet chocolate, dark chocolate, and white chocolate. Other ingredients present in chocolate include but are not limited to sweeteners (such as sugar and non-sugar sweeteners), cocoa liquor, cocoa butter, dairy ingredients, vegetable fats, and / or emulsifiers.

[0186] The polysaccharide and / or the composition can be incorporated into a candy coating food product. Other ingredients present in the candy coating food product include, but are not limited to, sweeteners, cocoa butter cocoa powder or cocoa butter equivalents, vegetable fats, emulsifiers and / or flavoring agents, such as, but not limited to, yogurt, strawberry, vanilla extract, white chocolate, mint, peanut butter and / or raspberry. The candy coating food product can be used for, but is not limited to, baked goods.

[0187] The polysaccharide and / or composition can be incorporated into a chocolate filling food product. Examples of chocolate filling food products include chocolate fillings placed in a chocolate shell, and / or chocolate fillings in baked goods such as cakes, brownies, cookie crisps, muffins, bread, sweet dough, pastries, muffins and / or cookies.

[0188] The polysaccharide and / or composition can be incorporated into a fat spread food product. Examples of fat spread food products include, but are not limited to, nut-based spreads such as peanut butter, almond butter and cashew butter, sweetened nut butters (such as sweetened hazelnut butter), dairy-based spreads and / or chocolate-based spreads.

[0189] The polysaccharide and / or composition may be incorporated into sweetened food products such as candies and / or confectionery bars, including but not limited to energy bars, snack bars, breakfast bars, and / or protein bars.

[0190] The polysaccharide and / or composition may be incorporated into the sugar crystals in an amorphous state. The sugar crystals may be used, but are not limited to, for adhering to the baked good and / or for forming a film or coating that enhances the appearance of the baked good.

[0191] The polysaccharide and / or composition may be incorporated into a fermented beverage. The fermented beverage may contain ethanol, preferably no more than 50 wt%, or no more than 15 wt%, or no more than 10 wt%, or no more than 8 wt% ethanol. The fermented beverage may be, but is not limited to, beer, such as ale or lager, cider, mead, wine, rice wine, sake, kombucha drink or sauerkraut juice.

[0192] The polysaccharide and / or composition can be incorporated into a dairy product including, but not limited to, dairy beverages, cheese, butter, yogurt, cottage cheese, custard, cottage cheese, cream cheese, curd, frozen dairy products such as frozen custard, frozen yogurt and ice cream, gelato, milk powder, sweetened condensed milk, sour cream, yogurt, whey, whey protein or whipped cream.

[0193] Other possible food and / or beverage products that may be incorporated into the polysaccharide and / or composition include, but are not limited to, frozen desserts, chewing gum, filled candies, mediated candies, lozenges, tablets, soft candies, mints, standard mints, powdered mints, chewy candies, hard candies, high temperature cooked candies, breath and oral care films or strips, candy canes, lollipops, soft candies, jellies, wine gums, soft candies, caramels, hard and soft icing foods, fruit snacks, taffy, toffee, liquorice candies, gelatin candies, jelly candies, jelly beans, nougat, fondant, meat analogs, breads, cakes, cookies, crackers, extruded snacks, soups, fried foods, pasta products, potato products, rice products, corn products, wheat products, dairy products, breakfast cereals, anhydrous coatings (e.g., ice cream compound coatings and chocolates), syrups, jams and jellies, beverages, plain waters, ready-to-drink beverages, protein drinks, toasted panini sandwiches, donuts, fillings, extruded and sheeted snacks, gelatin desserts, cheese, cheese sauces, liquid and dry coffee creamers, low milk solids cheese, low fat cheese, low calorie cheese, milk substitutes (such as but not limited to nut-based milk substitutes and oat-based milk substitutes), smoothies, ice cream, milkshakes, cottage cheese, cottage cheese sauce, dairy desserts, edible and water-soluble films, dressings, creamers, pastries, frostings, glazes, dry and wet pet foods, tortillas, puffed snacks, corn flakes, meat, fish, dried fruit, infant food, batters and / or breadings (such as batters and breadings for meat).

[0194] Advantageously, polysaccharide and / or composition are added to food and / or beverage product to provide a soluble fiber source. Polysaccharide and / or composition can advantageously increase the fiber content of food and / or beverage product without damaging the local flavor, mouthfeel or texture of the resulting food and / or beverage product. Polysaccharide and / or composition can optionally be added to product and / or beverage together with oligofructose, polydextrose, inulin, maltodextrin, resistant starch, starch, sucrose and / or conventional corn syrup solids. Polysaccharide and / or composition can be used as a substitute for the fiber of 0 % by weight to 100 % by weight in food and / or beverage product. Therefore, the resulting food or beverage product contains 0% to 100% less sugar.

[0195] Advantageously, polysaccharide and / or composition are added to food and / or beverage products to serve as sweetener.Polysaccharide and / or composition are suitable for replacing wholly or partially with other sweeteners, such as high fructose corn syrup, fructose, dextrose, regular corn syrup, corn syrup solids, sweet potato (such as Brazzein and / or Thaumatin), tapioca syrup, oat syrup, rice syrup and / or pea syrup.After replacing sweetener with polysaccharide and / or composition, sugar level reduces, but mouthfeel and local flavor remain the same or substantially the same.Polysaccharide and / or composition can be used as the substitute of the sweetener of 0 % by weight to 100 % by weight in food and / or beverage products.

[0196] Advantageously, polysaccharide and / or composition are added to food and / or beverage products to serve as fillers. Polysaccharide and / or composition are suitable for replacing with other fillers completely or in part, therefore alternative fat, flour, sugar alcohol, maltodextrin and / or other fillers present. After replacing fillers with polysaccharide and / or composition, caloric level is reduced, the nutritional properties of product are improved, and mouthfeel and local flavor remain the same or substantially the same. Polysaccharide and / or composition are used as substitutes for fillers of 0 % by weight to 100 % by weight in food and / or beverage products.

[0197] Advantageously, polysaccharides and / or compositions are added to food and / or beverage products to control or improve blood sugar concentrations in humans and animals suffering from diabetes. When humans or animals digest food and / or beverages containing polysaccharides and / or compositions, the polysaccharides and / or compositions can cause a more moderate relative blood sugar response in the bloodstream.

[0198] Method for producing polysaccharides and / or compositions comprising the same in food or beverage products

[0199] Another aspect of the present invention relates to a method for preparing a polysaccharide present in a food or beverage product and / or a composition comprising the polysaccharide. The method for preparing a food or beverage product comprises the following steps:

[0200] (a) providing a polysaccharide and / or a composition comprising the polysaccharide; and

[0201] (b) combining the polysaccharide and / or a composition comprising the polysaccharide with at least one food or beverage product.

[0202] Example

[0203] The following is a non-limiting example discussing the advantages of the present invention with reference to a table.The embodiments set forth herein are merely examples of many possible embodiments.

[0204] Example 1: Preparation of polysaccharides

[0205] In this non-limiting example of the present invention, a polysaccharide according to the present invention was prepared.

[0206] In this example, a sugar feed was prepared by mixing glucose monomers and glucose oligomers with water. Glucose monomers and glucose oligomers were combined with sorbitol (C*Sorbidex P16656) and citric acid in a weight ratio of 90:10:1, respectively. The dry mix was then mixed with water at 95°C to obtain a sugar feed containing 80% by weight solids, the remainder being water.

[0207] The sugar feed is then pumped into a microreactor containing three flow-guiding elements at a rate of 20 ml / min. The microreactor is operated at a temperature of 220° C. to 235° C. and a pressure of 2 bar to 5 bar. The residence time of the sugar feed in the microreactor is 70 seconds or less.

[0208] At the same time in the microreactor, 80% by weight of the glucose monomers and glucose oligomers react to form polysaccharides having a DPn content, wherein n is at least 3.

[0209] Example 2: Preparation of polysaccharides with lower weight % initial dry solids

[0210] In this non-limiting example of the present invention, a polysaccharide according to the present invention was prepared.

[0211] In this example, a sugar feed was prepared by mixing glucose monomers and glucose oligomers with water. Glucose monomers and glucose oligomers were combined with sorbitol (C*Sorbidex P16656) and citric acid in a weight ratio of 90:10:1, respectively. The dry mix was then mixed with water at 95°C to obtain a sugar feed containing 60% by weight solids, the remainder being water.

[0212] The sugar feed is then pumped into a microreactor containing three flow-guiding elements at a rate of 20 ml / min. The microreactor is operated at a temperature of 220° C. to 235° C. and a pressure of 2 bar to 5 bar. The residence time of the sugar feed in the microreactor is 70 seconds or less.

[0213] At the same time in the microreactor, 60% by weight of the glucose monomers and glucose oligomers react to form polysaccharides having a DPn content, wherein n is at least 3.

[0214] Example 3: Measurement of DP content of polysaccharides

[0215] In this non-limiting example of the present invention, the degree of polymerization (DP) content of the polysaccharide according to the present invention was measured.

[0216] In this embodiment, a first sugar feed is prepared by combining with sorbitol (C*Sorbidex P16656) and citric acid in a weight ratio of 90:10:1, respectively. The dry blend is then mixed with water at 95°C to obtain a first sugar feed containing 71.3% by weight solid content, the remainder being water. The first sugar feed is then pumped to a microreactor comprising three flow-guiding elements at a rate of 20 ml / min. The microreactor is operated at a temperature of 220°C to 235°C and a pressure of 2 bar to 5 bar. The residence time of the first sugar feed in the microreactor is 70 seconds or less. At the same time in the microreactor, 71.3% by weight of glucose monomers and glucose oligomers react to form a polysaccharide (referred to as polysaccharide A) having a DPn content.

[0217] In this embodiment, a second sugar feed is prepared by combining glucose monomers and glucose oligomers with sorbitol (C*Sorbidex P16656) and citric acid in a weight ratio of 90:10:1, respectively. The dry blend is then mixed with water at 95°C to obtain a second sugar feed containing 71.3% by weight solid content, the remainder being water. The second sugar feed is then pumped to a microreactor comprising three flow-guiding elements at a rate of 20 ml / min. The microreactor is operated at a temperature of 220°C to 235°C and a pressure of 2 bar to 5 bar. The residence time of the first sugar feed in the microreactor is 70 seconds or less. At the same time in the microreactor, 71.3% by weight of glucose monomers and glucose oligomers react to form a polysaccharide (referred to as polysaccharide B) having a DPn content.

[0218] The DPn content of polysaccharide A and polysaccharide B was then analyzed using an Ultimate 3000 three-channel pump HPLC coupled to a Q-exactive Focus mass spectrometer from ThermoFisher.

[0219] The Ultimate 3000 three-channel pump HPLC included peek tubing and was used with a mobile phase formed from 0.5 mM ammonium formate in a 50:50 volume ratio of MilliQ water / acetonitrile.

[0220] The temperature of the column was not controlled. The gradient used was isocratic. Prior to data collection, the column was washed with 0.5 mM ammonium formate in 50:50 volume ratio MilliQ water / acetonitrile.

[0221] Water was added to each polysaccharide to form two separate compositions comprising 71.3 wt% of either polysaccharide A or polysaccharide B, with the remainder being water.

[0222] The compositions were then added to an Ultimate 3000 three-channel pump HPLC with an autosampler and analyzed individually. The temperature of the autosampler was 10°C. The autosampler provided a 5 μl injection volume of the composition to the Ultimate 3000 three-channel pump HPLC. Inside the Ultimate 3000 three-channel pump HPLC, the composition had a flow rate of 0.3 ml / min. The Ultimate 3000 three-channel pump HPLC scanned the composition with negative polarity. The run time in the Ultimate 3000 three-channel pump HPLC was 0.5 minutes.

[0223] The Q-exactive Focus mass spectrometer analyzed the composition in groups of three. The Q-exactive Focus mass spectrometer was operated in MS scan mode with a MS scan of 100 uma-2500 uma and a peak width of 0.2 min.

[0224] Comparative samples were analyzed and labeled as comparative polysaccharides in Table 1.

[0225] The comparative sample was a polysaccharide from Example 3 in WO2011091962A1, the disclosure of which is hereby incorporated by reference. The comparative sample was mixed with water at 80°C to form a composition comprising 72 wt% polysaccharide, the remainder being water.

[0226] The DP content of the comparative polysaccharide was measured using the same method used to determine the DP content of polysaccharide A and polysaccharide B.

[0227] The experimental results are listed in Table 1.

[0228] Table 1: DPn content of polysaccharides according to the present invention and comparative examples .

[0229]

[0230] The "Other" content in the table above relates to any dextrose and other unknown impurities present in the sample.

[0231] Advantageously, the polysaccharide according to the invention has a higher distribution of small molecules present. This advantageously reduces the viscosity of the polysaccharide, resulting in a polysaccharide that is easier to process.

[0232] Example 4: Measurement of the fiber content of polysaccharides and compositions

[0233] In this non-limiting example of the present invention, the fiber content of the polysaccharide was measured.

[0234] The polysaccharide was prepared by the method outlined in Example 1. The dietary fiber content of the polysaccharide was then measured using the well-known method AOAC 2009.01.

[0235] A composition was then prepared, the composition comprising the polysaccharide prepared by the method outlined in Example 1. The composition comprised 49.7% by weight of the polysaccharide, the remainder being water.

[0236] The dietary fiber content of the composition was then measured using the well known method AOAC 2009.01.

[0237] Analysis of comparative samples.The comparative sample was a polysaccharide from Example 3 in WO2011091962A1 , the disclosure of which is hereby incorporated by reference.The fiber content of the polysaccharide was then measured using the well-known method AOAC 2009.01.

[0238] The results of dietary fiber analysis are listed in Table 2.

[0239] Table 2: Dietary fiber content of polysaccharides and compositions according to the invention .

[0240] Material Dietary fiber content (weight %) Polysaccharides (according to the invention) 77 Composition (comprising the polysaccharide according to the present invention) 38.1 Polysaccharide (according to Example 3 in WO2011091962A1) 86

[0241] As described in Example 3 of WO2011091962A1 (the disclosure of which is hereby incorporated by reference), in order to produce a polysaccharide similar to the polysaccharide according to the present invention, the process requires at least 80 wt% dry solids in the starting product. The obtained polysaccharide had a fiber content of 86 wt%.

[0242] However, the present invention advantageously does not require a starting product containing at least 80% by weight dry solids in the starting product. The starting product may contain a much lower dry solids content. The resulting polysaccharide has a fiber content of 77% by weight. Advantageously, the fiber content of the polysaccharide formed by the present invention does not depend on the dry solids content of the starting material.

[0243] Another advantage of the present invention is that polysaccharides with high fiber content similar to the two-step process described in WO2011091962A1 (the disclosure of which is hereby incorporated by reference) can be obtained by a simpler one-step process, resulting in a more efficient and economical process.

[0244] Example 5: Composition according to the invention

[0245] In this non-limiting example, a polysaccharide composition comprising a polysaccharide according to the invention was prepared.

[0246] In this example, a polysaccharide having a fiber content of 38.1% by weight was prepared according to the method set out in Example 1. The polysaccharide was then added to water to form a composition. The polysaccharide was present in the water at 49.7% by weight.

[0247] The features disclosed in the preceding description or in the following claims or in the accompanying drawings, expressed in their specific form or as means for performing the disclosed functions, or as methods or processes for appropriately obtaining the disclosed results, may be used alone or in any combination of such features to realize the invention in its various and different forms.

[0248] Although certain exemplary aspects of the invention have been described, the scope of the appended claims is not intended to be limited to these embodiments. The claims should be interpreted literally, equivocally, and / or encompassing equivalents.

Claims

1. A polysaccharide, comprising: 5 to 35% by weight of 1,2-glycosidic bonds and 1,3-glycosidic bonds, 25 to 35 wt. % of 1,4-glycosidic bonds, and 35 to 45% by weight of 1,6-glycosidic bonds, wherein the polysaccharide has a DP1 and DP2 content, wherein DP1 and DP2 are present in a combined weight % of greater than 15 wt % to 25 wt %.

2. The polysaccharide of claim 1, wherein DP1 and DP2 are present in a combined weight % of greater than 15 wt% to 25 wt%, or greater than 17.5 wt% to 22.5 wt%, or at 20 wt%, wherein the weight % is measured on a dry basis; and / or, wherein the polysaccharide has a DP1+ content of 90 wt% to 99 wt%, or 92 wt% to 96 wt%, or 93.6 wt%, wherein the wt% are measured on a dry basis; and / or, wherein the polysaccharide has a DP1 content of 2 wt% to 5 wt%, or 3 wt% to 4 wt%, or 3.5 wt%, wherein the wt% are measured on a dry basis; and / or, wherein the polysaccharide comprises 1 wt% to 4 wt%, or 2 wt% to 3 wt%, or 2.4 wt% 1,6-anhydrodextrose, wherein the wt% is measured on a dry basis; and / or, wherein the polysaccharide has a DPn content, wherein n is equal to 8 or more, wherein the DPn is present at 55 wt% or less, or 50 wt% or less, wherein the wt% is measured on a dry basis; and / or, wherein the polysaccharide has a DP3 to DP7 content, wherein the DP3 to DP7 are present in a combined weight % of 28 wt % to 45 wt %, or 29 wt % to 35 wt %; and / or, The polysaccharide comprises or consists of glucose monomers and / or oligomers; optionally, wherein the polysaccharide comprises 50% to 100% by weight of glucose monomers and / or oligomers, or 60% to 100% by weight of glucose monomers and / or oligomers, or 70% to 100% by weight of glucose monomers and / or oligomers, or 80% to 100% by weight of glucose monomers and / or oligomers, or 90% to 100% by weight of glucose monomers and / or oligomers, or 100% by weight of glucose monomers and / or oligomers; and / or wherein the polysaccharide has a fiber content of 70% to 85% by weight, or 75% to 80% by weight, or 77% by weight; and / or, wherein the polysaccharide has a 5-hydroxymethylfurfural (HMF) content of less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2.5 ppm, or 2 ppm; and / or, wherein the polysaccharide has a furfural content of less than 5 ppm, or less than 4 ppm, or less than 3 ppm, or less than 2.5 ppm, or 2 ppm; and / or, wherein the polysaccharide has a Gardner color value of less than 2, or less than 1.5, or less than 1.25, or less than 1.1, or less than 1.05, or less than 1.0, or less than 0.9, or preferably 0.8; and / or, wherein the polysaccharide has a pH of 4 to 6, or 4.5 to 5.5, or 5.1; and / or, The polysaccharide is polydextrose and / or resistant dextrin.

3. A composition comprising: The polysaccharide according to any one of claims 1 to 3; and water; optionally, wherein the composition comprises 40% to 90% by weight, or 45% to 80% by weight dry solids; optionally, wherein the dry solid comprises or consists of the polysaccharide.

4. A method for preparing the polysaccharide according to claim 1 or claim 2, the method comprising: (a) providing a sugar feed comprising glucose monomers and / or glucose oligomers; (b) providing at least one acid catalyst; (c) providing a microreactor comprising one or more flow guiding elements; as well as (d) passing the sugar feed through the microreactor in the presence of the acid catalyst until at least 80 wt % of the glucose monomers and / or glucose oligomers in the sugar feed have reacted to form polysaccharides having a DPn content, wherein n is at least 3.

5. The method of claim 4, wherein the sugar feed comprises a dry matter content of less than 80 wt%, or less than 70 wt%, or less than 60 wt%; optionally, wherein the remaining weight % of the sugar feed is water; and / or, wherein the dry matter content comprises at least 50 wt%, or at least 55 wt%, or at least 60 wt% of the glucose monomers and / or glucose oligomers; and / or wherein the dry matter content comprises: Up to 50%, or up to 45%, or up to 40% by weight of monosaccharides, disaccharides and oligosaccharides; and The monosaccharides, disaccharides and oligosaccharides do not include glucose monomers and / or glucose oligomers.

6. A method according to claim 4 or claim 5, wherein at least 85 wt%, or at least 90 wt%, or at least 95 wt% of the glucose monomers and / or glucose oligomers in the sugar feed are reacted to form polysaccharides having a DPn content, wherein n is at least 3; and / or, wherein the microreactor is operated at a temperature of 180°C to 250°C, or 190°C to 245°C, or 200°C to 240°C, or 220°C to 235°C, or 220°C; and / or, wherein the microreactor is operated at a pressure of 2 bar to 25 bar, or 2 bar to 20 bar, or 2 bar to 15 bar, or 2 bar to 10 bar, or 2 bar to 5 bar, or 2 bar to 3 bar; and / or, wherein the residence time of the sugar feed in the microreactor is 180 seconds or less, or 120 seconds or less, or 100 seconds or less, or 90 seconds or less, or 80 seconds or less, or 70 seconds or less, or 60 seconds or less, or 50 seconds or less, or at least 5 seconds, or at least 10 seconds, or at least 15 seconds; and / or, wherein the glucose monomers and / or glucose oligomers have a DPn content, wherein n has an average value of 3 to 10; and / or, wherein the glucose monomers and / or glucose oligomers are derived from glucose syrup or maltodextrin; optionally, (i) wherein the glucose syrup has a dextrose equivalent (DE) of 20 or greater; or, (ii) wherein the maltodextrin has a dextrose equivalent (DE) of 3 to 20.

7. The method according to any one of claims 4 to 6, wherein the sugar feed comprises a polyol; optionally, The polyol is any one of glycerol, erythritol, threitol, arabitol, xylitol, ribitol, allitol, altritol, gulitol, galactitol, mannitol, sorbitol, talitol, maltitol, isomalt, isomalt, lactitol or a combination thereof.

8. The method according to any one of claims 4 to 7, wherein the acid catalyst is any one of phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid, or a combination thereof.

9. The method according to claim 7 or claim 8, wherein the polyol is sorbitol and the acid catalyst is any one of phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof; and / or, wherein the sugar feed comprises the glucose monomers and / or glucose oligomers, the polyol and the acid catalyst in a weight ratio of 85:15:1 to 95:5:1, respectively; or, The sugar feed comprises the glucose monomers and / or glucose oligomers, the polyol and the acid catalyst in a weight ratio of 90:10:1, respectively.

10. The method according to any one of claims 4 to 9, wherein the microreactor comprises a plurality of flow guiding elements; optionally, depending on the size of each flow guiding element, comprises 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49 or 50 flow guiding elements or more; optionally, The plurality of flow guiding elements are arranged as follows: in series; or in parallel; or A portion of the plurality of flow guiding elements is in a first series connection, a portion of the plurality of flow guiding elements is in a second series connection, and the first series connection and the second series connection are connected in parallel.

11. The method according to any one of claims 4 to 10, wherein: The flow-guiding element is a device for achieving a defined guidance of a certain volume of fluid flow through a channel-shaped element; wherein in the channel-shaped element, the microchannel structure flow-guiding element is arranged to divide the volume flow and to guide the generated fluid flow division; The construction is arranged in such a way that the partial flows are guided so that they come into contact alternately with the inner wall of the channel-shaped element and with other partial flows.

12. The method according to claim 11, wherein the cross section of the channel-shaped element is designed to be circular, annular, elliptical or rectangular; and / or, wherein the flow guide element comprises a catalytically active material; optionally, Wherein the microchannel structure flow guiding element further comprises a carrier material, and the catalytically active material is supported on the carrier material; optionally, wherein the support material is carbon or silicon dioxide; optionally, wherein the catalytically active material is an acid; optionally, The acid is any one of phosphoric acid, citric acid, malic acid, succinic acid, adipic acid, gluconic acid, tartaric acid, fumaric acid or a combination thereof.

13. The method according to claim 11 or claim 12, wherein the microchannel structure guide element comprises a catalytically active material, an anti-corrosion material, an anti-fouling layer or a combination thereof; optionally, Wherein the microchannel structure guide element further comprises a carrier material, and the catalytically active material, the anti-corrosion material, the anti-fouling layer or a combination thereof is loaded on the carrier material; optionally, The support material is carbon or silicon dioxide.

14. The method according to any one of claims 4 to 13, wherein the method does not comprise a flash drying step; and / or, wherein the method does not include a water reduction step; and / or, wherein the method comprises passing the sugar feed through the microreactor once; and / or, The method further comprises one or more of the following steps: chromatography, hydrogenation, filtration (by ultrafiltration or membrane filtration), activated carbon treatment, decolorization, electrolysis, ion exchange resin or a combination thereof.

15. A food or beverage product, comprising the polysaccharide according to any one of claims 1 to 2; optionally, wherein the food product is a dairy product; optionally, wherein the dairy product is a milk-based beverage; or, wherein the food product is a confectionery food product; optionally, wherein the confectionery food product is gummy candy, jelly candy, gelatin candy, chewing gum or jelly beans.

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