US3928062A - Method for obtaining anhydrous fructose crystals - Google Patents

Method for obtaining anhydrous fructose crystals Download PDF

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Publication number
US3928062A
US3928062A US435525A US43552574A US3928062A US 3928062 A US3928062 A US 3928062A US 435525 A US435525 A US 435525A US 43552574 A US43552574 A US 43552574A US 3928062 A US3928062 A US 3928062A
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fructose
crystals
solution
process according
crystallization
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Toshio Yamauchi
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DKS Co Ltd
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Dai Ichi Kogyo Seiyaku Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K11/00—Fructose

Definitions

  • This invention relates to a method for obtaining anhydrous fructose crystals from an aqueous solution containing fructose. More particularly, it relates to the method whereby anhydrous fructose crystals are obtained economically and in a high yield from an aqueous solution containing fructose.
  • crystalline fructose occurs in the forms of anhydrous fructose, the hemihydrate or the dihydrate. Since the hemihydrate or dihydrate generally crystallizes out more easily than anhydrous fructose, it is difficult to obtain crystalline anhydrous fructose from the aqueous solution containing fructose by crystallization. This can be explained by the fact that the metastable range of a supersaturated solution of fructose in which the growth of existing crystals can take place without the formation of additional crystal nuclei is relatively narrow and the range lies close to the supersaturating point of the hemihydrate. This therefore makes it difficult to crystallize anhydrous crystalline fructose out from the aqueous solution. The formation of the hemihydrate or dihydrate crystals makes the massecuite of the crystallizing process pasty so that further growth of crystals is greatly retarded.
  • the anhydrous crystals are more advantageous than the hemihydrate or the dihydrate for various purposes because the dihydrate will melt even during transportation, packaging, or other handling processes thereof, especially in the summer.
  • anhydrous fructose crystals may be obtained by crystallizing from an aqueous methanolic or ethanolic solution of fructose.
  • the use of such organic solvents is undesirable not only from an economical point of view, but the resulting crystals and the mother liquor contain the solvent used which must be completely removed prior to the consumption.
  • An object of the present invention is to provide a method for obtaining anhydrous fructose crystals from an aqueous solution containing fructose.
  • Another object is to provide a method for crystallization of anhydrous fructose in which the crystals are separated out from the aqueous solution thereof without using any organic solvent.
  • anhydrous fructose crystals can be obtained from aqueous solutions of fructose in high yields without forming the hemi-or dihydrate crystals if the crystallization is carried out within a certain range of fructose concentration and temperature.
  • this range lies within the supersaturation area a below the point at which the hemihydrate begins to crystallize out. If a supersaturated solution falling within such range is seeded with crystals of anhydrous fructose and then the equilibrium between the liquid-solid phases of the system is shifted to a direction in which the degree of supersaturation of the liquid phase is enhanced, crystallization of anhydrous fructose may be achieved very satisfactorily.
  • FIG. I is a graph showing the range of fructose concentration in the liquid phase and the temperature thereof within which the crystallization of anhydrous fructose crystals takes place in accordance with the present invention.
  • FIG. 2 is a graph which typically shows the change of the concentration-temperature relationship in a few embodiments of the present invention.
  • the concentration and the temperature of the starting fructose solution in water are adjusted to a point within the range defined by points A, B, C and D in FIG. 1.
  • the solution is seeded with a small amount of anhydrous fructose crystals and then concentrated and/or cooled under moderate stirring within said range so that crystallization of anhydrous fructose takes place.
  • This crystallization step may be carried out in several manners as shown in FIG. 2.
  • the starting point is shown at a.
  • the anhydrous fructose crystallizes out as the concentration rises to a point at b.
  • the crystallization may take place as the temperature lowers to a point at 0 while maintaining substantially constant concentration by cooling and concentrating the solution simultaneously, or as both the temperature and the concentration lower from a point at e to point f by simultaneous cooling of the solution while concentrating under reduced pressure at a lower speed of evaporation than in the above case. Cooling under atmospheric pressure without concentrating may also be employed. In this case the fructose concentration and the temperature lower from point a to point g.
  • the foregoing procedures may be employed alone or in combination thereof depending upon the situation to give a satisfactory results.
  • the range within which the crystallization of the present invention must be carried out is defined by points A, B, C and D.
  • A, B, C and D locate at temperatures of 25C, 60C, 25C and 60C, and at concentrations of 83%, 95.5%, 8 l% and 89.7% respectively.
  • the crystallization is carried out within the range defined by points G, H, C and D wherein G and H locate at temperatures of 25C and 60C, and at concentrations 82.6% and 94% respectively.
  • the starting fructose solution at a is gradually cooled from temperature I to I, while a sufficient amount of water is evaporated under reduced pressure from the solution to maintain a constant level of the initial fructose concentration c,,.
  • the rate of temperature-fall is preferably such that the increase of crystallization speed becomes linear to the operation time and is between 0.2 to C, more preferably 03C per hour. The rate above 15C per hour will cause the formation of pseudocrystals and is, therefore, undesirable.
  • This procedure may be conducted by simply cooling the solution under atmospheric pressure.
  • the selection of the above-described procedures l to (4) depends in part on the type of crystallization apparatus and the' instrumentation thereof, but substantially the same yield can be achieved using any one of them.
  • the procedures 1 to (3) above are different from the procedure (4) in that the fructose level in the mother liquor from which the resulting crystals have been separated is kept to a higher or the same, or slightly lower levels than that of the starting solution. This enables the use of each mother liquor for recovering a second or further crops as such.
  • the fructose level in the mother liquor resulting from procedure (4) necessarily decreases proportionally to the yield of crystals. Therefore, the mother liquor must be concentrated to the starting level at a certain point for obtaining a second or further crops.
  • the former three procedures are more advantageous than the latter.
  • the starting fructose solutions which may be employed in practising the present invention include those obtained from inversion of sucrose or from isomerization of glucose.
  • these starting fructose solutions may be subjected to the crystallization of the present invention as such. Otherwise the concentration and the temperature of the solution must be brought into said range by conventional means such concentration, dilution, heating or cooling. If the fructose proportion in the total sugar content thereof is less than 88%, it is necessary to increase the fructose proportion to greater than 88%. This can be accomplished in a conventional manner by removing other sugars from the mixture.
  • the solution preferably contains from 83 to 95.5% (dry basis) of total sugar comprising 88 to 99% of fructose.
  • concentrations greater than 90%, particularly 92 to 95% make the evaporation speed decrease greatly because of their high viscosity. Therefore, a higher evaporation temperature such as to C and a longer period of time are required for the concentration thereof.
  • concentrations such as less than 90% are preferable for the present invention.
  • Adjustment of pH for example, pH at 3.9 5.7 by the addition of food-grade hydrochloric acid is also effective to prevent deterioration.
  • the initial temperature must be from 45 to 60C. If 60C has been chosen as the initial temperature, then the abovementioned procedure (I) wherein the temperature of 60C is maintained, or procedure (2) wherein the 90% of sugar concentration is maintained can be taken into consideration. Similarly, procedure (3) can be also be taken into consideration when the starting solution has the sugar concentration of 90% and the initial temperature of 55C. In this case, the solution is concentrated and cooled while maintaining the constant concentration of 90% in the first stage, then is cooled without concentration. It must be noted that the initial temperature close to the line A B of FIG.
  • a temperature below 50C is not preferable in the above case and the starting solution is subjected to the crystallization step.
  • the solution having a sugar concentration of 90% and an initial temperature of 55C is charged in a vacuum crystallization vessel while maintaining the temperature at 55ilC and the pH at 4.5i0.3.
  • the crystallization vessel is installed with heating and cooling means, and a rotary stirring-wing therein. The stirring is controlled to such extent that it is not sufficient to cause any crushing or growing crystals or generation of heat.
  • the solution is allowed to standfor a certain period of time, for example, for 20 to 30 minutes to stabilize the system, and then seeded with l to 4% by weight of seed crystals based on the weight of the charged solution.
  • the seed crystals preferably have a particle size of I00 I50 mesh (Tyler, 0.06 0.1 mm).
  • the addition of seed crystals may be achieved using a form of massecuite which was previously prepared by suspending the crystals in the fructose solution.
  • the resulting solution is gradually cooled and concentrated under reduced pressure in accordance with the aforementioned procedure (2). Addition of seed crystals often brings fine air-bubbles into the solution. These bubbles retard the growth of crystals and heat-transfer between the vessel and the solution.
  • Removal of these bubbles may easily be accomplished by conventional means such as evacuation.
  • the crystallization vessel is evacuated to 80 to 60mm Hg, the bubbles are removed for to minutes from the massecuite as the result ing foams disappear on the surface of the solution.
  • the degree of evacuation should be controlled to such extent that the foams do not overflow by watching the level from the viewing window.
  • the significance of crystallization by concentrating under reduced pressure resides in that it prevents a decrease of sugar concentration resulting from the crystallization, maintains crystallization in the metastable supersaturation range and increases the speed and the yield of the crystallization.
  • the rate of temperature-fall is 1 to 4 hours/C, pref erably 2.5 to 3 hours/C.
  • the preferable degree of vacuum is to 60mm Hg, although it varies with the temperature and fructose concentration.
  • the crystals begin to grow without forming pseudo-crystals when the temperature begins to fall.
  • the speed of growth is inversely proportional to the speed of temperature-fall and is directly proportional to the speed of concentration. Therefore the amount of 20 crystals formed may increase linearly to the time.
  • the massecuite becomes very viscous.
  • the yield of crystals reaches higher than 50%. it is almost a mud and transfer or separation of massecuite becomes difficult.
  • the mother syrup of the second crop or fresh fructose solution may be added to reduce the viscosity and to ease centrifugation.
  • the syrup is added at the final stage of the crystallization step after adjusting its sugar concentration to the same or a slightly higher level than the massecuite at the same temperature. 10 to parts by weight of the syrup per 100 parts by weight of massecuite are suitable for this purpose. Then the massecuite is taken from the crystallization vessel and centrifuged.
  • the centrifuge is provided with ajacket and is warmed at a temperature of 30 to 50C. This makes the separation of syrup easier, especially in winter.
  • the separation may easily be accomplished by a conventional means.
  • the resulting crystals are washed with small amounts of warm water (30 45C) 2 to 3 times to remove syrup remaining on the crystal surfaces. 5 to 10 parts of water are preferable to wash 100 parts of crystals.
  • the crystals thus prepared are then dried preferably at a temperature of 50 to 60C under reduced pressure below 100mm Hg whereby free-flowing anhydrous fructose crystals are obtained. Yield of the first crop of crystals ranges from 40 to 50 parts per 100 parts by weight of fructose in the starting solution.
  • crystals melt at 101 104C and have an optical purity of 100%.
  • the aforementioned procedure (4) (a g) may be applied to the same starting solution.
  • a temperature between 45C and C is preferable for the fructose solution. Therefore, the temperature and pH are adjusted at 58C and at 3.9 to 5.7 respectively.
  • the solution is seeded with l to 4% of anhydrous fructose crystals mesh/Tyler). After seeding, the solution is stirred slowly for 10 to 20 minutes to disperse seeds uniformly. The temperature is reduced by cooling at a rate of 1 to 02C per hour. As the crystallization proceeds, the massecuite becomes viscous as well.
  • Crystallization is stopped when the yield of crystals reaches 45 to 50% for 20 to 25 hours at which point the temperature has fallen to 30 to 35C. Separation of the resulting massecuite is carried out by centrifuging and the resulting crystals are washed with water and dried as the aforementioned manner.
  • Example 3 The starting solution of Example 3 was prepared by adding a sufficient amount of glucose to the fructose used in Example I to make a 92.6% fructose content. This fructose content corresponds to that of the mother liquor obtained in Example 7. This fact suggests that the mother liquor may be used repeatedly for the crystallization of further crops in the same manner as the first crop without any additional treatment.
  • Examples 5 and 8 illustrate examples wherein the crystallization took place in part outside the range of FIG. 1. In these examples, a large amount of pseudocrystals appeared within 3 to 4 hours and the massecuite became too viscous to continue the crystallizatron.
  • crystallization of the anhydrous fructose can satisfactorily be accomplished only when the crystallization takes place within the range defined by A, B, C and D. preferably by G, H, C and D, in FIG. 1.
  • the range above line A B in FIG. 1 is believed to be that in which the crystallization of fructose hemihydrate will take place.
  • the range defined A, B, C and D is that in which the seed crystals can grow without formation of additional nuclei.
  • line E F is the extended saturation curve of fructose in water reported by R. F. Jackson, J. Phys. Chem. 56, 1092-1096 1952.
  • the yield and the time required are not influenced by the purity of starting fructose, size or shape of seed crystals, or the quantity thereof, but mainly depend on the evaporation speed of water from the massecuite. Furthermore, it has been found that the crystals grow almost linearly to the evaporation speed. Therefore, the crystallization vessel used for earring out the present invention is preferably installed with means to control the sugar concentration of the massecuite and the degree of vacuum during the operation, and has a good heat-transfer coefficient.
  • a process for obtaining anhydrous fructose crystals without the formation of fructose hemihydrate or fructose dihydratc crystals from an aqueous solution of fructose which comprises:
  • a process according to claim I further comprising centrifuging the resultant massecuite at 3050 C., washing the resultant crystals with warm water and drying the washed crystals at 5060 C. under reduced pressure.
  • a process according to claim 1. wherein the concentrating is carried out with gradual cooling at the rate of 0.2-1 .5 C. per hour such that the resultant increase in crystallization speed becomes a linear function of the operation time.
  • fructose solution has a sugar concentration of less than by weight and a pH of 3.9-5.7.

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US435525A 1973-02-12 1974-01-22 Method for obtaining anhydrous fructose crystals Expired - Lifetime US3928062A (en)

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Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199374A (en) * 1978-12-22 1980-04-22 Chimicasa Gmbh Process of preparing crystalline fructose from high fructose corn syrup
US4199373A (en) * 1979-04-13 1980-04-22 Chimicasa Gmbh Process for the manufacture of crystalline fructose
EP0028136A1 (en) * 1979-10-24 1981-05-06 Cetus Corporation Process for the production of D-Glucosone and D-Fructose
US4517021A (en) * 1983-10-28 1985-05-14 A. E. Staley Manufacturing Company Semi-crystalline fructose
US4643773A (en) * 1984-03-09 1987-02-17 A. E. Staley Manufacturing Company Crystallization of fructose utilizing a mixture of alcohols
US4666527A (en) * 1983-11-29 1987-05-19 Kato Kagaku Co., Ltd. Continuous crystallization of fructose anhydride
US4724006A (en) * 1984-03-09 1988-02-09 A. E. Staley Manufacturing Company Production of crystalline fructose
US4861382A (en) * 1985-03-13 1989-08-29 Tate & Lyle Plc Sugar process
US4895601A (en) * 1988-12-12 1990-01-23 Archer Daniels Midland Company Aqueous-alcohol fructose crystallization
US4931101A (en) * 1985-05-15 1990-06-05 Roquette Freres Method and installation for the preparation of anhydrous crystalline dextrose
US4938804A (en) * 1987-06-03 1990-07-03 Suomen Sokeri Oy Method for the crystallization of fructose
US4988531A (en) * 1989-11-07 1991-01-29 A. E. Staley Manufacturing Company Method for manufacturing gel pieces
US5004507A (en) * 1988-12-12 1991-04-02 Archer Daniels Midland Company Aqueous-alcohol fructose crystallization
US5015297A (en) * 1985-05-15 1991-05-14 Roquette Freres Method and installation for the production of anhydrous crystalline fructose
US5039346A (en) * 1988-03-25 1991-08-13 A. E. Staley Manufacturing Company Fructose syrups and sweetened beverages
US5047088A (en) * 1989-06-30 1991-09-10 A. E. Staley Manufacturing Company Method for crystallization of fructose
USH1014H (en) 1988-04-28 1992-01-07 A. E. Staley Manufacturing Company Method of making cherries of maraschino type
US5230742A (en) * 1987-02-02 1993-07-27 A. E. Staley Manufacturing Co. Integrated process for producing crystalline fructose and high-fructose, liquid-phase sweetener
US5234503A (en) * 1987-02-02 1993-08-10 A.E. Saley Manufacturing Co. Integrated process for producing crystalline fructose and a high-fructose, liquid-phase sweetener
US5258199A (en) * 1991-08-30 1993-11-02 A. E. Staley Manufacturing Co. Chocolate-flavored confections and method for manufacturing
US5350456A (en) * 1987-02-02 1994-09-27 A. E. Staley Manufacturing Company Integrated process for producing crystalline fructose and a high fructose, liquid-phase sweetener
US5368878A (en) * 1990-02-20 1994-11-29 A. E. Staley Manufacturing Company Reduced fat meat products
US5372835A (en) * 1990-02-20 1994-12-13 A. E. Staley Manufacturing Company Method of preparing reduced fat foods
US5374442A (en) * 1990-02-20 1994-12-20 A. E. Staley Manufacturing Company Method of preparing reduced fat foods
US5376399A (en) * 1992-05-15 1994-12-27 A.E. Staley Manufacturing Co. Reduced fat cremes
USH1395H (en) * 1992-05-22 1995-01-03 A. E. Staley Manufacturing Company Composition and method of preparing reduced fat spreads
US5378491A (en) * 1990-02-20 1995-01-03 A. E. Staley Manufacturing Co. Method of preparing a starch hydrolysate, an aqueous starch hydrolysate dispersion, method of preparing a food containing a starch hydrolysate, and a food formulation containing a starch hydrolysate
USH1394H (en) * 1992-05-22 1995-01-03 A. E. Staley Manufacturing Company Method of preparing reduced fat spreads
US5378286A (en) * 1990-02-20 1995-01-03 A. E. Staley Manufacturing Co. Method of preparing reduced fat foods
US5387426A (en) * 1990-02-20 1995-02-07 A.E. Staley Manufacturing Company Method of preparing reduced fat foods
US5395640A (en) * 1990-02-20 1995-03-07 A.E. Staley Manufacturing Company Method of preparing reduced fat foods
US5409726A (en) * 1990-02-20 1995-04-25 A. E. Staley Manufacturing Co. Method of preparing reduced fat foods
US5436019A (en) * 1990-02-20 1995-07-25 A. E. Staley Manufacturing Co. Method of preparing reduced fat foods
US5656094A (en) * 1987-02-02 1997-08-12 A.E. Staley Manufacturing Company Integrated process for producing crystalline fructose and a high-fructose, liquid phase sweetener
US6093326A (en) * 1993-01-26 2000-07-25 Danisco Finland Oy Method for the fractionation of molasses
US6206977B1 (en) * 1992-01-27 2001-03-27 Danisco Finland Oy Method for crystallizing anhydrous fructose from its aqueous solutions
US6214125B1 (en) 1994-09-30 2001-04-10 Danisco Finland Oy Fractionation method for sucrose-containing solutions
US6224776B1 (en) 1996-05-24 2001-05-01 Cultor Corporation Method for fractionating a solution
US6663780B2 (en) 1993-01-26 2003-12-16 Danisco Finland Oy Method for the fractionation of molasses
US6681495B2 (en) * 1999-03-31 2004-01-27 Okuma Corporation Measuring apparatus and method for correcting errors in a machine
US20040231662A1 (en) * 2001-08-15 2004-11-25 De Mendonca Ferreira Joao Afonso Process for the production of crystallin fructose of high purity utlizing fructose syrup having a low content of fructose made from sucrose and product obrained
US6896811B2 (en) 2001-05-09 2005-05-24 Danisco Sweeteners Oy Chromatographic separation method
EP2292803A1 (en) 2009-07-07 2011-03-09 Danisco A/S Separation process
US20110237790A1 (en) * 2010-03-26 2011-09-29 Cj Cheiljedang Corp. Method of producing d-psicose crystals
CN105938382A (zh) * 2015-03-06 2016-09-14 苹果公司 具有隔离的腔天线的电子设备
US11084840B2 (en) 2016-12-27 2021-08-10 Samyang Corporation Method for purifying allulose conversion reaction product
US12071451B2 (en) 2020-05-05 2024-08-27 Amalgamated Research Llc Systems including simulated moving bed separators for high purity fructose production and related methods

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GB1456260A (en) * 1974-01-28 1976-11-24 Suomen Sokeri Oy Method for crystallization of fructose from water solution
EP0613953B1 (en) * 1991-08-20 1999-02-03 A.E. Staley Manufacturing Company Fructose and dextrose containing liquid sweetener

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US2588449A (en) * 1950-03-03 1952-03-11 Us Agriculture Levulose dihydrate
US3513023A (en) * 1966-04-29 1970-05-19 Boehringer Mannheim Gmbh Process for the production of crystalline fructose
US3607392A (en) * 1967-12-21 1971-09-21 Boehringer Mannheim Gmbh Process and apparatus for the recovery of crystalline fructose from methanolic solution
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Cited By (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4199374A (en) * 1978-12-22 1980-04-22 Chimicasa Gmbh Process of preparing crystalline fructose from high fructose corn syrup
US4199373A (en) * 1979-04-13 1980-04-22 Chimicasa Gmbh Process for the manufacture of crystalline fructose
EP0028136A1 (en) * 1979-10-24 1981-05-06 Cetus Corporation Process for the production of D-Glucosone and D-Fructose
US4517021A (en) * 1983-10-28 1985-05-14 A. E. Staley Manufacturing Company Semi-crystalline fructose
US4666527A (en) * 1983-11-29 1987-05-19 Kato Kagaku Co., Ltd. Continuous crystallization of fructose anhydride
US4724006A (en) * 1984-03-09 1988-02-09 A. E. Staley Manufacturing Company Production of crystalline fructose
US4643773A (en) * 1984-03-09 1987-02-17 A. E. Staley Manufacturing Company Crystallization of fructose utilizing a mixture of alcohols
US4861382A (en) * 1985-03-13 1989-08-29 Tate & Lyle Plc Sugar process
US4931101A (en) * 1985-05-15 1990-06-05 Roquette Freres Method and installation for the preparation of anhydrous crystalline dextrose
US5015297A (en) * 1985-05-15 1991-05-14 Roquette Freres Method and installation for the production of anhydrous crystalline fructose
US5230742A (en) * 1987-02-02 1993-07-27 A. E. Staley Manufacturing Co. Integrated process for producing crystalline fructose and high-fructose, liquid-phase sweetener
US5350456A (en) * 1987-02-02 1994-09-27 A. E. Staley Manufacturing Company Integrated process for producing crystalline fructose and a high fructose, liquid-phase sweetener
US5656094A (en) * 1987-02-02 1997-08-12 A.E. Staley Manufacturing Company Integrated process for producing crystalline fructose and a high-fructose, liquid phase sweetener
US5234503A (en) * 1987-02-02 1993-08-10 A.E. Saley Manufacturing Co. Integrated process for producing crystalline fructose and a high-fructose, liquid-phase sweetener
US4938804A (en) * 1987-06-03 1990-07-03 Suomen Sokeri Oy Method for the crystallization of fructose
US5039346A (en) * 1988-03-25 1991-08-13 A. E. Staley Manufacturing Company Fructose syrups and sweetened beverages
USH1014H (en) 1988-04-28 1992-01-07 A. E. Staley Manufacturing Company Method of making cherries of maraschino type
US5004507A (en) * 1988-12-12 1991-04-02 Archer Daniels Midland Company Aqueous-alcohol fructose crystallization
US4895601A (en) * 1988-12-12 1990-01-23 Archer Daniels Midland Company Aqueous-alcohol fructose crystallization
US5047088A (en) * 1989-06-30 1991-09-10 A. E. Staley Manufacturing Company Method for crystallization of fructose
US4988531A (en) * 1989-11-07 1991-01-29 A. E. Staley Manufacturing Company Method for manufacturing gel pieces
US5395640A (en) * 1990-02-20 1995-03-07 A.E. Staley Manufacturing Company Method of preparing reduced fat foods
US5409726A (en) * 1990-02-20 1995-04-25 A. E. Staley Manufacturing Co. Method of preparing reduced fat foods
US5374442A (en) * 1990-02-20 1994-12-20 A. E. Staley Manufacturing Company Method of preparing reduced fat foods
US6113976A (en) * 1990-02-20 2000-09-05 A.E. Staley Manufacturing Company Method of preparing reduced fat foods
US5372835A (en) * 1990-02-20 1994-12-13 A. E. Staley Manufacturing Company Method of preparing reduced fat foods
US5378491A (en) * 1990-02-20 1995-01-03 A. E. Staley Manufacturing Co. Method of preparing a starch hydrolysate, an aqueous starch hydrolysate dispersion, method of preparing a food containing a starch hydrolysate, and a food formulation containing a starch hydrolysate
US5436019A (en) * 1990-02-20 1995-07-25 A. E. Staley Manufacturing Co. Method of preparing reduced fat foods
US5378286A (en) * 1990-02-20 1995-01-03 A. E. Staley Manufacturing Co. Method of preparing reduced fat foods
US5387426A (en) * 1990-02-20 1995-02-07 A.E. Staley Manufacturing Company Method of preparing reduced fat foods
US5368878A (en) * 1990-02-20 1994-11-29 A. E. Staley Manufacturing Company Reduced fat meat products
US5258199A (en) * 1991-08-30 1993-11-02 A. E. Staley Manufacturing Co. Chocolate-flavored confections and method for manufacturing
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FR2217421B1 (nl) 1978-01-13
DE2406663B2 (de) 1981-07-16
FR2217421A1 (nl) 1974-09-06
AU6545674A (en) 1975-08-14
GB1407785A (en) 1975-09-24
JPS5239901B2 (nl) 1977-10-07
DE2406663A1 (de) 1974-08-15
JPS49102853A (nl) 1974-09-28

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