EP0030941A1 - Cold water soluble fumaric acid - Google Patents

Cold water soluble fumaric acid

Info

Publication number
EP0030941A1
EP0030941A1 EP80900693A EP80900693A EP0030941A1 EP 0030941 A1 EP0030941 A1 EP 0030941A1 EP 80900693 A EP80900693 A EP 80900693A EP 80900693 A EP80900693 A EP 80900693A EP 0030941 A1 EP0030941 A1 EP 0030941A1
Authority
EP
European Patent Office
Prior art keywords
fumaric acid
dextrin
malto
product
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP80900693A
Other languages
German (de)
English (en)
French (fr)
Inventor
John J. Loporto
John J. Hennesey
Philip J. Petix
David Chin
Herbert Kopperman
John H. Gubbe
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Alberta Gas Chemicals Inc
Original Assignee
Alberta Gas Chemicals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Alberta Gas Chemicals Inc filed Critical Alberta Gas Chemicals Inc
Publication of EP0030941A1 publication Critical patent/EP0030941A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/68—Acidifying substances

Definitions

  • the present invention relates to a fumaric acid composition having an enhanced rate of solubility in cold water and to a method for manufacturing same.
  • Fumaric acid has long been used as an acidulant in various food products, particularly in dry beverages mixes where quick dissolution in cold water at 2 to 5°C is necessary.
  • fumaric acid is hydrophobic in nature because of the low resultant dipole moment inherent in its chemical structure. Indeed solubility of fumaric acid in water at 25° C. is only 0.63 g. per 100 g. as compared to other acidulants such as citric acid or tartaric acid which are water soluble up to their own weight.
  • fumaric acid treated with a wetting agent is preferred as an acidulant, because it is substantially more effective than its competitors.
  • U.S. Patent 3,009,810 issued to Raffensperger and Takashima showed that fumaric acid particles would dissolve readily, if they were coated with 0.2 to 2.0% by weight of a partial low chain fatty ester of a polyoxyeth lene derivative of hexitol • anhydride derived from sorbitol.
  • Van Ness in U.S. Patent 3,151,986 eliminated the problem of agglomeration and caking associated with the Raffensperger product by admixing with fumaric acid particles 0.1 to 1.0% by weight of a -dialkyl ester of sodium sulfosuccinate conatining 7 to 11 carbons in each alkyl chain.
  • Demeler et al. -U.S. Patent 3,351,471 treated ultrafine fumaric acid crystals having a particle size below 10 microns with anionic and nonionic surfactants. This process, however, required that the particles of fumaric acid be in a micronized state in order for the dissolution in cold water to take place.
  • U.S. Patent 3,370,956 issued to Reitmann and Hamilton enhanced the solubility of fumaric acid by treating acid crystals with a water solution of a water soluble edible surfactant, the solution optionally containing a water dispersible edible film forming additive.
  • An example of the water soluble surfactant is a hydroxy- carboxylic acid of from about two to twelve cabon atoms such as citric and tartaric acid.
  • the film forming additive was selected from the group consisting of carbohydrates, water soluble gelatins. and surfactants, with effective amounts of this component ranging from about 0.001 to about 0.7% by weight based on total solids.
  • the fumaric acid is mixed with a surfactant to enhance solubility.
  • the surfactant lowers the surface tension at the solute crystal interface there ⁇ by accelerating the dissolution of the fumaric acid.
  • the absolute solubility of the acid at a given temperature is, of course, unchanged.
  • the preferred product of ⁇ the present invention is a granular fumaric acid composition of increased solu ⁇ bility in cold water which has little off flavor, can be manufactured to a particle size between 50 and 400 U.S. Standard Sieve, and exhibits goods material handling characteristics.
  • the solubility of the product is enhanced by coating fumaric acid crystals having a particle size,,., . between 10 and 40 microns with a film of a hydrol zed carbohydrate and then spray drying an aqueous slurry of-the treated particles to produce the granular product.
  • the pre ⁇ ferred carbohydrate is a maito-dextrin consisting of at least 75 % by weight of polysaccharides above trisaccharides.
  • It is an object of this invention to produce a cold water soluble fumaric acid composition said composition com ⁇ prised of fumaric acid particles coated wtih 2.5 to 10% by weight of a hydrolyzed carbohydrate wetting agent, the preferred carbohydrate being a maito-dextrin consisting of at least 75% by weight of polysaccharides above trisaccharides.
  • An additional object of this invention is to produce a cold water soluble fumaric acid composition of granular par ⁇ ticles between 50 and 400 U.S. Standard Sieve that can be sieved, screened or classified to discreet particle size compositions.
  • fumaric acid is used as an acidulent in the food industry, particularly in dry water soluble beverage mixes, .
  • an ingredient to be used as a wetting agent in a fumaric acid formulation must be edible. It should also be able to extend the shelf life of the fumaric acid, and not interfere in its characteristic acidic taste.
  • a hydrolyzed 0 carbohydrate of low sweetness and low dextrose equivalence can be used as a wetting agent for the fumaric acid.
  • the hydrolyzed carbohydrate is a malto-dextrin, which is defined as a polysaccharide constitutionally between dextrin and maltose, the composition being dependent upon the relative amounts of each, 5
  • Malto-dextrin is readily digestible natural food derivative produced from starch in barley during the manufacture of malt or from hydrolysis of corn starch.
  • the malto-dextrin should have a composition which contains at least 75% by weight of a polysaccharide above trisaccharide.
  • malto-destrin is available as Mor-rex (produced by Corn Products) and Maltrin (produced by Grain Processing Corporation) , which have the following typical physical properties and chemical analysis:
  • the preferred malto-dextrin wetting agents have low hygro- scopocit , which enhances the ability of malto-dextrin containing compositions to be spray dried. Furthermore, this property extends the shelf life of dry mixes containing malto- dextrin by preventing moisture absorption.
  • malto-dextrin is. accepted readily in the marketplace as a valuable food additive and is used currently in beverage powders, condi ⁇ ments, dehydrated foods, instant tea, cakes " and cookies to extend shelf life, control browning, and induce thickening.
  • Fumaric acid is a hydrophobic compound that is not easily wetted. Dissolution may be enhanced by drastic reduction in particle size in order to expose greater surface area to the solvent. Even then, however, the acid has a tendency to clump or agglomerate when added to an aqueous solution. While the reduction in particle size is beneficial, powdered fumeric is difficult to handle in that it has poor bulk flowability, creates substantial quantities of dust and is difficult to sieve properly.
  • Hydrolyzed carbohydrates are wetting agents which do not foam. Because they are low in sweetness they do not influence the flavor of the product, and have been used in a variety of other food preparations to extend shelf life.
  • the outside surface of the fumaric acid particles Upon receiving a coating of a hydrolyzed carbohydrate, the outside surface of the fumaric acid particles is easily wetted so that they become dispersed throughout the solution. This occurs because the malto-dextrin coating is hydrophilic in nature. Once the particles are dispersed, dissolution occurs at a faster rate, especially if accompanied by gentle stirring.
  • the fumaric -acid composition is obtained by milling fumaric acid crystals to a particle size between 10 and 40 microns, and then blending it with the hydrolyzed carbohydrates wetting agent.
  • the particle size of the fumaric acid after the milling operation determines the smallest particle size of the final fumaric acid composition.
  • Blending with the wetting agent may be performed in two ways. In the first method a dry mixture of fumaric acid particles and the wetting agent is obtained with the wetting agent comprising between 2.5 and 10% of the total dry mixture. This blend is then slurried with water to obtain an aqueous solution that is between 35 and 65% by weight solids.
  • the wetting agent may be admixed with milled fumaric acid by first dissolving the wetting agent completely in water, and then adding the fumaric acid particles to that solution to create a slurry as before. In each instance the object of coating the fumaric acid particles with the wetting agent is obtained by agitation of the slurry.
  • the slurry is then dried to obtain the finished fumaric acid product.
  • Spray drying is preferred because the particle size of the final product can be regulated by proper selection of spray nozzle type and size, the pressure of the atomizing air, and the rate of drying.
  • an inlet air temperature to the spray drying chamber is maintained between 150 to 250 ° C, while the outlet air temperature is controlled usually between 80 and 120° C.
  • Atomizing pressures depend upon nozzle selection, but generally lie in a range between 20 and 100 psig. These procedures produce a fumaric acid composition that ranges between 10 and 300 microns in size or approximately between 50 and 400 U.S. standard sieve.
  • the product which is granular in texture, exhibits excellent flow characteristics and is low in dust formation.
  • the spray dried fumaric acid composition of this invention may, unlike the prior art products, be sieved, screened or calssified to obtain products in particular particle size ranges.
  • Volatile.- matter in the dried material is preferably less than 1% by weight.
  • the dissolvability of fumaric acid as a function of time in 10% sugar solutions at 2 to 5° C. in grams per liter is shown in Table I below. Untreated fumaric acid is compared with 2.6, 5 and 9.1% malto-dextrin fumaric acid mixtures. From this table it is apparent that a fumaric acid composition containing between 4 and 7% malto-dextrin is preferred because higher concentrations of malto-dextrin increase the solubility of the acid in cold water only marginally. Above about 10% malto-dextrin the solubility of the fumaric acid in cold water .is not substantially enhanced.
  • Mor-rex malto-dextrin Twenty grams of Mor-rex malto-dextrin was dry mixed with 409 grams of fumaric acid milled to between 10 and 40 microns. This mixture was added to 600 milliliters of water at room tempera ⁇ ture to produce a slurry of about 40% by weight solids having a specific gravity of about 1.023 g./cc. The fumaric acid slurry was transferred from a two liter glass graduated feed flask to a two fluid aspirating type nozzle, Stork-3owen model number 59063, via a small Moyno pump at a feed rate of 77 ml./min.
  • the slurry was sprayed through the nozzle into a vertical spray drying chamber and the dried fumaric acid compo ⁇ sition collected.
  • the inlet air temperature was 160° C. and the outlet air temperature was 75° C.
  • the material that was collected ranged in size from 10 to 60 microns and had 0.5% by weight volatile matter.
  • the dissolvability of the treated fumaric acid in a 10% sugar solution at 2 to 5° C. was 1.51 g./l. after 30 seconds, 1.72 g./l. after 60 seconds and 1.89 g./l. after 120 seconds. At 20° C. the dissolvability in 10% sugar solution was 4.59 g./l. after 30 seconds, 4.61 g./l. after 60 seconds and 4.58 g./l. after 120 seconds.
  • Mor-rex malto-dextrin was dry mixed with 1080' grams of fumaric acid milled to between 10 and 40 microns. This mixture was added to 1450 milliliters of water at room temperature to produce a slurry of about 45% by weight solids having a specific gravity of about 1.037 g./cc.
  • the fumaric acid slurry was transferred from a glass graduated feed flask to a two fluid aspirating type nozzle, Stor -Bowen model number 5906B, via a small Moyno pump at a feed rate of 63 ml./min.
  • the slurry was sprayed through the nozzle into a vertical spray drying chamber and the dried fumaric acid composition collected.
  • the inlet air temperature was 160° C. and the outlet air temperature was 75° C.
  • the material that was collected ranged in size from 20 to 80 microns and had 0.5% by weight volatile matter.
  • the dissolvability of the treated fumaric acid in a 10% sugar solution at 2 to 5° C. was 1.62 g./l. after 30 seconds, 1.77 g./l. after 60 seconds and 1.86 g./l. after 120 seconds.
  • Mor-rex malto-dextrin Ten grams of Mor-rex malto-dextrin was dry mixed with 375 grams of fumaric acid milled to between 10 and 40 microns. This mixture was added to 715 milliliters of water at room temp ⁇ erature to produce a slurry of about 35% by weight solids having a specific gravity of about 1.120 g./cc.
  • the fumaric acid slurry was transferred from a glass graduated feed flask to a two fluid aspirating type nozzle, Stork-Bowen model number 5906B, via a small Moyno pump at a feed rate of 105 ml./min. Using an atom ⁇ izing force of 40 psig (3.8454 kg/cm.
  • the slurry was sprayed through the nozzle into a vertical spray drying chamber and the dried fumaric acid composition collected.
  • the inlet air temp ⁇ erature was 180° C. and the outlet air temperature was 75° C.
  • the material that was collected ranged in size from 10 to 60 microns and had Q.5% bv wei ⁇ ht volatile matter.
  • the dissolvability of the treated fumaric acid in a 10% sugar solution at 2 to 5° C. was 1.21 g/1. after -30 seconds, - 1.38 g/1. after 60 seconds and 1.65 g/1. after 120 seconds.
  • the slurry was sprayed through these nozzles into a horizontal spray drying chamber and the dried fumaric acid was screened and collected.
  • the fumaric product was analyzed and found to contain 5% of the wetting agent.
  • the inlet air temper ⁇ ature was 309° F. (154° C.) and the outlet air temperature was 172° F. (77.8° C).
  • the material that was collected ranged in size from 325 mesh to greater than 170 mesh and had 0.5% by weight volatile matter.
  • the dissolvability of the treated fumaric acid in ' a 10% sugar solution at 2 to 5° C. was 2.01 g./l. after . 30 seconds and 2.06 g./l. after 60 ' seconds.

Landscapes

  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Jellies, Jams, And Syrups (AREA)
EP80900693A 1979-04-26 1980-11-17 Cold water soluble fumaric acid Withdrawn EP0030941A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3354579A 1979-04-26 1979-04-26
US33545 1979-04-26

Publications (1)

Publication Number Publication Date
EP0030941A1 true EP0030941A1 (en) 1981-07-01

Family

ID=21871031

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80900693A Withdrawn EP0030941A1 (en) 1979-04-26 1980-11-17 Cold water soluble fumaric acid

Country Status (5)

Country Link
EP (1) EP0030941A1 (enrdf_load_stackoverflow)
JP (1) JPS5754110B2 (enrdf_load_stackoverflow)
GB (1) GB2068705B (enrdf_load_stackoverflow)
NL (1) NL8020128A (enrdf_load_stackoverflow)
WO (1) WO1980002364A1 (enrdf_load_stackoverflow)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6320666U (enrdf_load_stackoverflow) * 1986-07-21 1988-02-10

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA635273A (en) * 1962-01-23 General Foods Corporation Fumaric acid composition and preparation thereof
GB765885A (en) * 1953-07-25 1957-01-16 Goldschmidt Ag Th Dispersing pulverulent substances in water
US3016299A (en) * 1959-02-09 1962-01-09 Gen Foods Corp Fumaric acid composition
US3359119A (en) * 1964-03-27 1967-12-19 Reynolds Tobacco Co R Method of preparing an agglomerated food product
US3853706A (en) * 1967-03-30 1974-12-10 Cpc International Inc Process for producing non-waxy starch hydrolysates
US3681086A (en) * 1969-07-30 1972-08-01 Gen Foods Corp Process for making jams and jellies
US3821436A (en) * 1971-07-20 1974-06-28 Abbott Lab Food-flavor-composition
US3962468A (en) * 1974-03-07 1976-06-08 General Foods Corporation Spray-dried L-aspartic acid derivatives
US4059706A (en) * 1974-03-07 1977-11-22 General Foods Corporation Spray-dried L-aspartic acid derivatives
US4022924A (en) * 1974-05-13 1977-05-10 General Foods Corporation Dry acidulents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8002364A1 *

Also Published As

Publication number Publication date
WO1980002364A1 (en) 1980-11-13
JPS5754110B2 (enrdf_load_stackoverflow) 1982-11-16
JPS56500518A (enrdf_load_stackoverflow) 1981-04-23
GB2068705A (en) 1981-08-19
GB2068705B (en) 1983-08-17
NL8020128A (nl) 1981-02-27

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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Designated state(s): FR

18D Application deemed to be withdrawn

Effective date: 19810424

RIN1 Information on inventor provided before grant (corrected)

Inventor name: KOPPERMAN, HERBERT

Inventor name: PETIX, PHILIP J.

Inventor name: HENNESEY, JOHN J.

Inventor name: CHIN, DAVID

Inventor name: GUBBE, JOHN H.

Inventor name: LOPORTO, JOHN J.