US3779796A - Sodium propionate coated with sorbitan higher fatty acid ester and process for its preparation - Google Patents

Sodium propionate coated with sorbitan higher fatty acid ester and process for its preparation Download PDF

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Publication number
US3779796A
US3779796A US00164808A US3779796DA US3779796A US 3779796 A US3779796 A US 3779796A US 00164808 A US00164808 A US 00164808A US 3779796D A US3779796D A US 3779796DA US 3779796 A US3779796 A US 3779796A
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United States
Prior art keywords
sodium propionate
sorbitan
fatty acid
acid ester
higher fatty
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Expired - Lifetime
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US00164808A
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English (en)
Inventor
R Ueno
T Miyazaki
S Inamine
S Kishi
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Ueno Fine Chemicals Industry Ltd
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Ueno Fine Chemicals Industry Ltd
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2/00—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
    • B01J2/30—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic using agents to prevent the granules sticking together; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/50—Use of additives, e.g. for stabilisation

Definitions

  • the coating is per- [51] Int. Cl 844d 1/00, 844d 5/08 formed y adding 10-500 ppm y e ght of the SOrbi- 581 Field of Search 117/100 A, 167; tan higher fatty acid ester to an aqueous solution of 99/224 118 163 166 90 167; 260/526, sodium propionate, removing the aqueous medium 537 R 540; 252/384 from the resultant mixture, and drying it.
  • Sodium propionate finds wide applications as a preservative for bread and cakes and also for animal feed. This compound is very hydroscopic and tends to cake. Even when it is sealed from the atmospheric air in an attempt to avoid moisture absorption, it cakes to form a mass under a relatively small load. Therefore, when bags of sodium propionate are stacked and stored for prolonged periods of time, the sodium propionate cakes considerably and is not easily disintegrated.
  • the caking of a water-sluble substance is considered to be due to the fact that on the surfaces of the particles of the substance, the cycle of dissolving the particles in moisture contained in the particles and recrystallizing them by evaporation of water is repeated, and that the transfer of substance takes place to cause the particles to adhere to one another at their contacting surfaces to form a mass.
  • Caking therefore, is closely related to the amount of moisture and areas of contact between the particles, and as a matter of course, proceeds markedly with an increase in the mositure content and the contacting area. In order to prevent the caking of such a substance, it is necessary to reduce the moisture content as much as possible, and minimize the contacting area.
  • sodium propionate can be dried to a moisture content of about 0.1 to 0.5 percent.
  • drying costs are very high.
  • the caking of sodium propionate has been prevented for example by packing sodium propionate in units of to kilograms and placing each unit in one box so as not to exert a large load, or by coating the surfaces of the particles with a water-insoluble substance such as calcium carbonate, magnesium carbonate, calcium phosphate, or calcium stearate.
  • the former method of avoiding a large load is based on the minimization of the areas of contact between the crystals of sodium propionate as mentioned above.
  • sodium propionate is produced in large quantities, it is difficult to pack it into boxes automatically. This requires large manpower, and the cost of packaging boxes adds to the cost of the sodium propionate, which appreciably affects the cost of production of the sodium propionate.
  • the latter method of preventing caking of sodium propionate by a water-soluble anti-caking agent is also based on the minimization of the areas of contact between the crystals of sodium propionate.
  • the amount of anticaking agent should be as much as l to 10 percent based on the weight of sodium propionate in order to produce the intended anti-caking effect.
  • the anti-caking agent must be mixed after sodium propionate has been obtained in the form of crystals, and a procedure of thoroughly mixing them is required.
  • the anti-caking effect is not durable, and when the anti-caking agent is added to water, turbidity is very evident.
  • a non-caking sodium propionate coated with a sorbitan higher fatty acid is provided.
  • a process for preventing the caking of sodium propionate which comprises coating sodium propionate with the sorbitan higher fatty acid ester.
  • Sodium propionate as referred to in the present invention, is in the form of crystals, powders, granules or flakes, the particle size ranging from 50 microns to 5
  • the sorbitan higher fatty acid ester used as a coating agent in the present invention is substantially colorless, odorless, and non-toxic, and can effectively prevent caking when used in small amounts.
  • the sorbitan fatty acid ester are esters of sorbitan with fatty acids having 12 to 18 carbon atoms, and specifically include sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan tristearate, sorbitan monoleate, or sorbitan trioleate.
  • Sorbitan monolaurate, sorbitan monooleate, and sorbitan trioleate are especially preferred as they are oily substances at room temperature.
  • Other sorbitan fatty acid esters are waxy substances, and difficult to dissolve in an aqueous medium. But if they are added to a heated aqueous medium (for example, to C.), relatively uniform dispersing is possible, and therefore, they can also be used.
  • One embodiment of the process of the present invention comprises mixing an aqueous solution of sodium propionate with 10-500 ppm by weight, based on the sodium propionate, of a sorbitan higher fatty acid ester to make a uniform dispersion, removing the aqueous medium from the dispersion, and drying it to therby obtain coated sodium propionate.
  • Another embodiment of the process of the invention involves adding sodium propionate to a 0.1-l wt. percent (preferably 0.20.8 wt. percent) solution of a sorbitan higher fatty acid ester in an organic solvent, mixing them with each other, collecting sodium propionate by such means as filtration, removing the organic solvent, and drying the product to thereby obtain coated sodium propionate.
  • excess sorbitan higher fatty acid ester is contained in the filtrate.
  • the filtration should be performed at reduced pressure such that 10-500 ppm by weight of the sorbitan higher fatty acid ester will remain in the sodium propionate.
  • the removal of the excess sorbitan higher fatty acid ester may be carried out by centrifugal separation.
  • suction filtration or centrifugal separation isstopped when an organic solvent solution of 10-500 ppm by weight, based on the sodium propionate, of the sorbitan higher fatty acid ester remains. This can be determined by measuring the ester content of the sample.
  • sodium propionate is added to a solution in an organic solvent of 10-500 ppm of a sorbitan higher fatty acid ester to form a slurry. Thereafter, the organic solvent is removed, and the remainder dried to recover coated sodium propionate.
  • an organic solvent solution of 0.5-5 wt. percent (preferably 1-3 wt. percent) sorbitan higher fatty acid ester is sprayed onto sodium propionate while the latter is being stirred so that the amount of the sorbitan higher fatty acid ester in the resulting coated sodium propionate is -500 ppm; subsequent drying gives coated sodium propionate.
  • Sodium propionate is generally produced by adding an aqueous solution of sodium hydroxide to an aqueous solution of propionic acid to neutralize the latter and form an aqueous solution containing 20-50 wt. percent of sodium propionate, and drying the solution to produce solid sodium propionate.
  • a predetermined amount of a sorbitan higher fatty acid ester may be added during the manufacture of sodium propionate described to effect uniform dispersion. This simply leads to coated sodium propionate without using any particular operation. Therefore, the process utilizing water as the medium is preferred because ofits low cost of production.
  • Examples of the organic solvent used in the process of the invention include lower alcohols such as methanol, ethanol, propanol, isopropanol, or n-butanol, benzene-type hydrocarbons such as benzene, xylene and toluene, and aliphatic hydrocarbons such as chloroform and hexane.
  • the organic solvents that are used in the invention have a boiling point of 50 to 150C., preferably 60l20C., and can dissolve the sorbitan higher fatty acid ester of a predetermined amount and be removed by heating or spray drying.
  • the preferred organic solvents are lower alcohols or benzene.
  • the removal and drying of the aqueous medium or organic medium can be effected by customary means.
  • drum drying or spray drying by heating under reduced pressure or atmospheric pressure or by heating with hot air can be utilized in the invention.
  • the drying is performed until the resulting coated sodium propionate has a moisture content of O. l-l percent by weight, preferably 0.1-0.5 percent by weight, based on the sodium propionate.
  • crystals or powders of sodium propionate having a particle size of about 50 microns to 500 microns are coated with the sorbitan higher fatty acid ester.
  • granular sodium propionate having a particle size of 0.5 to 1 mm to flaky sodium propionate having a particle size of 0.5 to 5 mm are coated with the sorbitan fatty acid ester.
  • sodium propionate can be made into fine crystals (3-50 microns). Because of their small size, however, such fine crystals especially tend to scatter off and absorb moisture to a great extent, and are not commercially feasible. Gathering of the fine crystals will result in powders (SO-500 microns), granules (0.5 to 1 mm), or flakes (0.5 to 5 mm).
  • the amount of sodium propionate to be added to the aqueous solution in the first-mentioned embodiment is 10 to percent by weight, preferably 20 to 50 percent by weight. If sodium propionate is dissolved in hot water to prepare an aqueous solution, the concentration of it in the aqueous solution is usually about 60 percent by weight, but the preferred concentration is 20 to 50 percent by weight.
  • the amount of the sorbitan higher fatty acid ester coated as the anti-caking agent is 10 to 500 ppm by weight, preferably 30 to 300 ppm by weight based on the weight of sodium propionate. If the amount is less than 10 ppm by weight, the anti-caking effect is insufficient, and amounts around 200 ppm are most effective. Amounts larger than 500 ppm by weight result in a descreased anti-caking effect, and the increased amounts of the sorbitan higher fatty acid ester adversely affect the quality of the sodium propionate. The reason is considered to be that the increased amounts of the sorbitan higher fatty acid ester cause the wetting of the crystals of sodium propionate.
  • the sorbitan higher fatty acid esters used in the process of the invention as an anti-caking agent are colorless, odorless, and non-toxic, and are suitable for use in coating sodium propionate which is a preservative for fooodstuffs.
  • a marked anti-caking effect is exhibited by using as small an amount as l0-500 ppm by weight of this sorbitan ester on the basis of the sodium propionate. Such small amounts do not affect the efficacy of sodium propionate, nor cause marked reduction in purity.
  • the product of the present invention retains its transparency even when dissolved in water, and hardly differs from uncoated sodium propionate.
  • the anticaking effect attained by the present invention is also excellent in that even in the source of long periods of time under a load, the effect is hardly lost.
  • EXAMPLE 1 A dispersion of each of the sorbitan fatty acid esters indicated in Table l in 10 times their weight of water was added to a 40 percent aqueous solution of sodium propionate in the concentrations indicated in Table l. The resultant mixture was spray dried to form powders of sodium propionate having a moisture content of 0. l 5 to 0.2 percent.
  • the degree of caking of the powders of sodium propionate obtained was measured by the following method. Eight grams of the sample were packed into a cylinder having a diameter of 3 cm and a height of 4 cm, and a pressure of l kg/cmG was applied to the sample at 37C. and a relative humidity of 50 percent to shape the sample for one hour. The load needed to destroy the shaped article was determined. On the other hand, sodium propionate containing no anti-caking agent was shaped, and the load needed to destroy the shaped article was determined.
  • the break load for the shaped article of sodium propionate containing no anti-caking agent was defined as l, and the degree of caking was defined as a ratio of the break load for the shaped article of sodium propionate containing anti-caking agent against the break load for the shaped article containing no anti-caking agent.
  • the results are given in Table l.
  • the break load of 0 in the table indicates that there was hardly any caking, and the product lost its shape upon withdrawal from the vessel.
  • EXAMPLE 2 One thousand kilograms of a 40 percent aqueous solution containing 400 kg of sodium propionate were mixed with 200 g of a dispersion of 20 g of sorbitan monolaurate in 180 g of water, and the mixture was uniformly stirred. The mixture was drum dried to form flaky sodium propionate having a moisture content of 0.1 percent.
  • Sorbitan monopalmitate 200 0.20 0.24 300 0.30 0.35 500 0.73 0.86 10 0.84 0.99 50 0.69 0.81
  • EXAMPLE 4 600 Grams of sorbitan monooleate were added to 30 kg of benzene, and a solution was prepared by heating to 45C.. Ten kilograms of flaky sodium propionate (moisture content 0.2 percent by weight) having a particle diameter of 1 3 mm were added, and mixed for 30 minutes while stirring the solution so that the surface of sodium propionate was thoroughly wetted with the benzene solution. The mixture was then subjected to suction filtration so that the sodium propionate contained 4 percent by weight of the benzene solution. Sodium propionate was taken out, and benzene was completely evaporated in hot air at C., followed by drying. Coated sodium propionate containing 400 ppm of sorbitan monooleate was obtained.
  • EXAMPLE 5 Powders of sodium propionate having a particle size of 200 to 500 microns (10 kg) were put into a coating pan. While rotating the pan, 30 g of an iso-propyl alcohol solution at 45C. containing 2 percent by weight of sorbitan monolaurate were sprayed onto the surface of sodium propionate. Thereafter, by blowing hot air at 70C., isopropyl alcohol was evaporated. This cycle of spraying and hot air blowing was repeated five times, and a total of g of the iso-propyl alcohol solution was sprayed so that the amount of sorbitan monolaurate in the coated sodium propionate was 300 ppm. Sodium propionate coated with sorbitan monolaurate was obtained.
  • EXAMPLE 6 Three grams of sorbitan monopalmitate were added to 20 kg of methanol, and a complete solution was prepared by heating to 45C. 10 kg of sodium propionate having a particle diameter of 200 to 500 microns were added, and with slow stirring, a uniform slurry was prepared. Methanol was evaporated by a drum dryer, followed by drying. Sodium propionate coated with 300 ppm of sorbitan monopalmitate was obtained.
  • Non-caking sodium propionate having a particle diameter of 50 microns to 5 mm coated with a sorbitan higher fatty acid ester in an amount of 10 to 500 ppm by weight based on the weight of the sodium propionate.
  • sorbitan higher fatty acid ester is an ester wherein said sorbitan higher fatty acid ester is selected from the group consisting of sorbitan monolaurate, sor bitan monooleate and sorbitan trioleate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Glanulating (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • General Preparation And Processing Of Foods (AREA)
US00164808A 1970-07-24 1971-07-21 Sodium propionate coated with sorbitan higher fatty acid ester and process for its preparation Expired - Lifetime US3779796A (en)

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JP45064295A JPS493512B1 (enrdf_load_stackoverflow) 1970-07-24 1970-07-24

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US (1) US3779796A (enrdf_load_stackoverflow)
JP (1) JPS493512B1 (enrdf_load_stackoverflow)
AU (1) AU459905B2 (enrdf_load_stackoverflow)
BE (1) BE770372A (enrdf_load_stackoverflow)
DE (1) DE2136973C3 (enrdf_load_stackoverflow)
FR (1) FR2101909A5 (enrdf_load_stackoverflow)
GB (1) GB1333397A (enrdf_load_stackoverflow)
NL (1) NL164458C (enrdf_load_stackoverflow)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0054016A2 (en) 1978-11-03 1982-06-16 Tetra Laval Holdings & Finance SA Apparatus for electron-beam irradiation of surfaces
US5096718A (en) * 1982-09-17 1992-03-17 The State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University Preserving foods using metabolites of propionibacteria other than propionic acid
US5635484A (en) * 1982-09-17 1997-06-03 The State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University Propionibacteria peptide microcin
US20030203004A1 (en) * 2002-04-24 2003-10-30 Kelm Gary Robert Compositions comprising short and long chain fatty acids and methods of their use for the management of body weight
US20050136166A1 (en) * 2003-09-19 2005-06-23 ICS Holding, Inc. Preparation of an edible product from dough
US20060286213A1 (en) * 2005-04-25 2006-12-21 Innovative Cereal System, Llc Preparation of an edible product from dough
US20140264156A1 (en) * 2013-03-14 2014-09-18 Ecolab Usa Inc. Composition for mineral supplement anticaking and dust control
CN108191679A (zh) * 2018-02-10 2018-06-22 安徽唯诗杨信息科技有限公司 一种具有生物活性的面包防霉剂的合成方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2183173A (en) * 1938-12-22 1939-12-12 Jefferson Island Salt Mining C Method of treating salt and resulting product
US2830906A (en) * 1955-08-03 1958-04-15 Swift & Co Yeast plasticizer
US2932574A (en) * 1958-01-06 1960-04-12 Robert C Bour Monoglyercide aqueous emulsion and process of preparing same
US3008986A (en) * 1959-05-26 1961-11-14 Du Pont Odor-controlled sodium propionate-sodium dipropionate composition
CA673321A (en) * 1963-10-29 J. Tacey Wesley Anti-caking agent and composition
US3164476A (en) * 1962-07-03 1965-01-05 H C Fisher Company Emulsifier for cake batters
US3459798A (en) * 1966-06-23 1969-08-05 Du Pont Process for preventing caking of adipic acid,and product
US3507665A (en) * 1966-05-25 1970-04-21 Quaker Oats Co Coating emulsions and method of coating foodstuffs
US3617299A (en) * 1969-09-15 1971-11-02 Abbott Lab Animal feed premix resistant to static charge and method of making same

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA673321A (en) * 1963-10-29 J. Tacey Wesley Anti-caking agent and composition
US2183173A (en) * 1938-12-22 1939-12-12 Jefferson Island Salt Mining C Method of treating salt and resulting product
US2830906A (en) * 1955-08-03 1958-04-15 Swift & Co Yeast plasticizer
US2932574A (en) * 1958-01-06 1960-04-12 Robert C Bour Monoglyercide aqueous emulsion and process of preparing same
US3008986A (en) * 1959-05-26 1961-11-14 Du Pont Odor-controlled sodium propionate-sodium dipropionate composition
US3164476A (en) * 1962-07-03 1965-01-05 H C Fisher Company Emulsifier for cake batters
US3507665A (en) * 1966-05-25 1970-04-21 Quaker Oats Co Coating emulsions and method of coating foodstuffs
US3459798A (en) * 1966-06-23 1969-08-05 Du Pont Process for preventing caking of adipic acid,and product
US3617299A (en) * 1969-09-15 1971-11-02 Abbott Lab Animal feed premix resistant to static charge and method of making same

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0054016A2 (en) 1978-11-03 1982-06-16 Tetra Laval Holdings & Finance SA Apparatus for electron-beam irradiation of surfaces
US5096718A (en) * 1982-09-17 1992-03-17 The State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University Preserving foods using metabolites of propionibacteria other than propionic acid
US5260061A (en) * 1982-09-17 1993-11-09 The State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University Propionibacteria metabolites inhibit spoilage yeast in foods
US5635484A (en) * 1982-09-17 1997-06-03 The State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon State University Propionibacteria peptide microcin
US20030203004A1 (en) * 2002-04-24 2003-10-30 Kelm Gary Robert Compositions comprising short and long chain fatty acids and methods of their use for the management of body weight
US7981452B2 (en) 2003-09-19 2011-07-19 Innovative Cereal System Llc Preparation of an edible product from dough
US20050136166A1 (en) * 2003-09-19 2005-06-23 ICS Holding, Inc. Preparation of an edible product from dough
US20090136636A1 (en) * 2003-09-19 2009-05-28 Innovative Cereal System Llc. Preparation of an edible product from dough
US7575769B2 (en) 2003-09-19 2009-08-18 Innovative Cereal System Llc Preparation of an edible product from dough
US8545917B2 (en) 2003-09-19 2013-10-01 Innovative Cereal System Llc Preparation of an edible product from dough
US20060286213A1 (en) * 2005-04-25 2006-12-21 Innovative Cereal System, Llc Preparation of an edible product from dough
US20090214732A1 (en) * 2005-04-25 2009-08-27 Innovative Cereal System, Llc Preparation of an edible product from dough
US20140264156A1 (en) * 2013-03-14 2014-09-18 Ecolab Usa Inc. Composition for mineral supplement anticaking and dust control
WO2014158442A1 (en) * 2013-03-14 2014-10-02 Ecolab Usa Inc. Composition for mineral supplement anticaking and dust control
CN108191679A (zh) * 2018-02-10 2018-06-22 安徽唯诗杨信息科技有限公司 一种具有生物活性的面包防霉剂的合成方法

Also Published As

Publication number Publication date
DE2136973A1 (enrdf_load_stackoverflow) 1972-01-27
BE770372A (fr) 1971-12-01
JPS493512B1 (enrdf_load_stackoverflow) 1974-01-26
DE2136973B2 (de) 1978-10-26
GB1333397A (en) 1973-10-10
AU3160671A (en) 1973-01-25
FR2101909A5 (enrdf_load_stackoverflow) 1972-03-31
DE2136973C3 (de) 1979-06-21
NL164458C (nl) 1981-01-15
AU459905B2 (en) 1975-04-10
NL164458B (nl) 1980-08-15
NL7110222A (enrdf_load_stackoverflow) 1972-01-26

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