WO2001049814A1 - Process for refining animal and vegetable oil - Google Patents

Process for refining animal and vegetable oil Download PDF

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Publication number
WO2001049814A1
WO2001049814A1 PCT/CA2000/000028 CA0000028W WO0149814A1 WO 2001049814 A1 WO2001049814 A1 WO 2001049814A1 CA 0000028 W CA0000028 W CA 0000028W WO 0149814 A1 WO0149814 A1 WO 0149814A1
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WO
WIPO (PCT)
Prior art keywords
oil
silica
animal
triglycerides
absorbent
Prior art date
Application number
PCT/CA2000/000028
Other languages
French (fr)
Inventor
Michel Delmas
George E. Walsh
Original Assignee
Caboto Seafoods
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 Caboto Seafoods filed Critical Caboto Seafoods
Priority to PCT/CA2000/000028 priority Critical patent/WO2001049814A1/en
Priority to CA002406910A priority patent/CA2406910C/en
Priority to CNB008190410A priority patent/CN1261553C/en
Priority to AU30279/00A priority patent/AU3027900A/en
Publication of WO2001049814A1 publication Critical patent/WO2001049814A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/10—Refining fats or fatty oils by adsorption
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/20—Inorganic substances, e.g. oligoelements
    • A23K20/28—Silicates, e.g. perlites, zeolites or bentonites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • 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
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
    • B01J20/103—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate comprising silica

Definitions

  • the field of the present invention is a process for the production of refined edible oils using absorbent silica.
  • Unprocessed vegetable and animal oils consist of a mixture of substances extracted from oily plants or fatty parts of animals by mechanical means such as pressing or crushing or by physical and chemical means such as stripping or hexane extraction.
  • the oil mixture generally consists of triglycerides, usually from about 90-99% by weight of the mixture.
  • the triglycerides are formed in living organisms by esterification of three hydroxy groups with fatty acids. These are organic acids with long hydrocarbon chains which can include one or several double bonds.
  • the oil mixture also includes other compounds, usually from 1-9% by weight, such as fatty acids, mono and diglycerides formed by esterification of one or two hydroxy groups of glycerol with an organic acid, phosphoglycerides which contain at least one atom of phosphorus, molecules coming from secondary metabolisms such as steroids, tocopherols, carotenes, and sugars. These other compounds are not triglyceride fatty acids and are non-saponificable. These compounds must be removed to allow the oil to be refined to a food quality standard suitable for human use.
  • Standard techniques to refine the oil are either a chemical or a physical type process or a combination of the two.
  • the chemical process uses slightly acidic aqueous solutions which are put in contact with the oil mixture in a first stage, to extract in the aqueous phase substances such as phosphoglycerides and polar molecules.
  • the oil phase is treated further with an aqueous base solution to remove free fatty acids.
  • the acidic or alkali washing and stripping with steam or through filtration generates aqueous wastes.
  • the oil is then filtered using clays. It may be filtered using silica. [P.J. Wan, American Oil Chemist Society, Introduction to Fats and Oil Technology 1991, pp 85-131, 137-163].
  • a finishing treatment as indicated above, may be performed on the resulting oil to give an edible oil.
  • the finishing treatment usually incorporates clays but may use silica. In either situation, silica is used only in the finishing step after the unrefined oil has been treated with a chemical and/or physical treatment.
  • the industrial refining technologies generate by-products at each stage of the refining process. Wastes of little or no value are generated and discarded and a small quantity of triglycerides is lost during refining. This process gives rise to a weight loss of approximately 2-10% between the unrefined oil and the refined oil.
  • the present invention provides for a process for treating animal or vegetable oil comprising the steps of treating the oil with absorbent silica; and separating the oil and silica to produce a refined oil wherein the silica absorbs little or no triglycerides from the oil.
  • the present invention also provides for a vegetable or animal oil refined by this process as well as an additive for animal feed comprising the silica used in this process.
  • Absorbent silica can be used in treating unrefined oil to trap non-saponifiable compounds, mono and diglycerides, phosphoglycerides, and trace metals without using acidic or alkali washing, stripping with steam or filtration on clays. Thus, large quantities of aqueous wastes are not generated.
  • the unrefined oil is treated with the absorbent silica and the oil is separated from the silica.
  • the desired triglycerides remain in the oil phase and the silica is saturated with these other molecules.
  • the saturated silica may hold back a small quantity of oil and becomes a good additive for animal feed since it has a good energy value.
  • the use of the absorbent silica to trap these compounds and remove them from the oil improves the quality of the resulting refined oil.
  • this technology does not produce waste by-products.
  • the resulting saturated silica which is removed from the oil can be reused as an additive for animal feed. The process is easy to use, clean, and does not require a large factory or significant investment in equipment.
  • the unrefined oil used in the process may be vegetable oil taken from fruits such as palm or olive oil or oils from seeds such as soya, rapeseed or sunflower oil. It may also be animal oils such as seal oil, whale oil, or fish oil.
  • the silica used to refine the oil has an agglomerate size of between about 50 and about 120 ⁇ m and a surface area of between 50 and about 250 m 2 /g. This size and surface area is most efficient for the fixation of compounds in the oil mixture other than the triglycerides to produce a refined oil.
  • the refined oil may be separated from the silica by filtration or percolation.
  • the resulting saturated silica which is separated from the oil may be used as an additive in animal feed without the need for further treatment.
  • This refining process is water-free and consequently does not generate aqueous water polluted effluents.
  • the quantity of silica used is directly linked to the quality of the oil and the quantity of compounds other than triglycerides which are found in the unrefined oil.
  • silica is arranged on the bottom of a column and the oil is percolated on it under pressure. Saturation of the silica is detectable when the white silica turns to a brownish colour. The saturated silica is then removed from the column and may be used as an animal feed additive. The amount of silica required will depend upon the quality and characteristics of the unrefined oil. Generally, 1 kg of silica will refine 10-15 kg of unrefined oil.
  • EXAMPLE 1 We put in a glass column (1) (diameter: 0.04m, height: 0.8m), 0.04 kg of absorbent silica (2) (average size of agglomerates: 60 ⁇ m, average surface area: 100 m 2 /g) retained by a cellulose filter (3) put on a metallic framework (4).
  • the soya oil stored in the container (5) has been obtained with a hexane extraction of soya seeds.
  • the average value of the acidity of the raw oil expressed in % of weight of oleic acid is of 1.2% .
  • the average value of 0.7 1/h is measured for the flow rate.
  • the saturation of the silica is obtained for an addition of 0.2 kg of raw oil.
  • the refined oil has an acidity expressed in % weight of oleic acid lower than 0.1 % which allows its use in human feeding.
  • the saturated silica is removed from the column and directly used as an additive animal feeding.
  • 0.3 kg of oil is then placed in the column (1) at room temperature with a device including a pump and a flood gate (7).
  • a pressure of 16 p.s.i. is applied with a compressor (7) fitted with a flood gate (8) after closing the flood gate (6).
  • the average value of 1.8 1/h is measured for the flow rate.
  • the saturation of silica is obtained after another addition of 0.25 kg of raw sunflower oil.
  • the refined oil has an acidity expressed in % weight of oleic acid lower than 0.1 % which allows its use in human feeding.
  • the saturated silica is removed from the column and directly used as an additive for animal feeding.
  • the seal oil stored in the container (5) has been extracted from the blubbers of harp seals.
  • the average value of the acidity expressed in % of weight of oleic acid is of 1.4% .
  • a pressure of 12 p.s.i. is applied with a compressor (7) fitted with a flood gate (8) after closing the flood gate (6).
  • the average value of 3.8 1/h is measured for the flood rate.
  • the saturation of silica is obtained after another addition of 27 kg of raw seal oil.
  • the refined oil has an acidity expressed in % weight of oleic acid lower than 0.1 % which allows its use in human feeding.
  • the saturated silica is removed from the column and directly used as an additive for animal feeding.
  • the seal oil stored in the container (5) has been extracted from the blubbers of harp seals.
  • the average value of the acidity expressed in % of weight of oleic acid is of 0.9% .
  • a pressure of 12 p.s.i. is applied with a compressor (7) fitted with a flood gate after closing the flood gate (6).
  • the average value of 4.2 1/h is measured for the flood rate.
  • the saturation of the silica is obtained after another addition of 35 kg of raw seal oil.
  • the refined oil has an acidity expressed in % weight of oleic acid lower than 0.1 % which allows its use in human feeding.
  • the saturated silica is removed from the column and directly used as an additive for animal feeding.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Analytical Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Animal Husbandry (AREA)
  • Microbiology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Fodder In General (AREA)

Abstract

The present invention provides for a process for refining animal or vegetable oil. Unprocessed oil is made up of triglycerides and other compounds such as fatty acids, mono and diglycerides formed by esterification of one or two hydroxy groups of glycerol with an organic acid, phosphoglycerides which contain at least one atom of phosphorus, molecules coming from secondary metabolisms such as steroids, tocopherols, carotenes, and sugars. The process of the present invention comprises treating the unprocessed oil with absorbent silica. The silica absorbs those compounds other than the triglycerides from the oil and absorbs little or no triglycerides. The silica is separated from the oil to produce a refined oil. The silica may then be used as an additive for animal feed.

Description

PROCESS FOR REFINING ANIMAL AND VEGETABLE OIL
The field of the present invention is a process for the production of refined edible oils using absorbent silica.
Unprocessed vegetable and animal oils consist of a mixture of substances extracted from oily plants or fatty parts of animals by mechanical means such as pressing or crushing or by physical and chemical means such as stripping or hexane extraction.
The oil mixture generally consists of triglycerides, usually from about 90-99% by weight of the mixture. The triglycerides are formed in living organisms by esterification of three hydroxy groups with fatty acids. These are organic acids with long hydrocarbon chains which can include one or several double bonds. The oil mixture also includes other compounds, usually from 1-9% by weight, such as fatty acids, mono and diglycerides formed by esterification of one or two hydroxy groups of glycerol with an organic acid, phosphoglycerides which contain at least one atom of phosphorus, molecules coming from secondary metabolisms such as steroids, tocopherols, carotenes, and sugars. These other compounds are not triglyceride fatty acids and are non-saponificable. These compounds must be removed to allow the oil to be refined to a food quality standard suitable for human use.
Standard techniques to refine the oil are either a chemical or a physical type process or a combination of the two. The chemical process uses slightly acidic aqueous solutions which are put in contact with the oil mixture in a first stage, to extract in the aqueous phase substances such as phosphoglycerides and polar molecules. The oil phase is treated further with an aqueous base solution to remove free fatty acids. The acidic or alkali washing and stripping with steam or through filtration generates aqueous wastes. The oil is then filtered using clays. It may be filtered using silica. [P.J. Wan, American Oil Chemist Society, Introduction to Fats and Oil Technology 1991, pp 85-131, 137-163].
The physical refining process allows the elimination of most of the compounds other than the triglycercides. A finishing treatment, as indicated above, may be performed on the resulting oil to give an edible oil. The finishing treatment usually incorporates clays but may use silica. In either situation, silica is used only in the finishing step after the unrefined oil has been treated with a chemical and/or physical treatment. [K. Carlson, Inform, American Oil Chemist Society, vol. 4, no. 3, pp 272-275, 1993].
The industrial refining technologies generate by-products at each stage of the refining process. Wastes of little or no value are generated and discarded and a small quantity of triglycerides is lost during refining. This process gives rise to a weight loss of approximately 2-10% between the unrefined oil and the refined oil.
There, therefore, is a need for a process to refine raw vegetable and animal oil which does not produce waste by-products. There is also a need to process raw vegetable and animal oils using a process which retains the triglycerides and removes the other substances without producing aqueous wastes.
The present invention provides for a process for treating animal or vegetable oil comprising the steps of treating the oil with absorbent silica; and separating the oil and silica to produce a refined oil wherein the silica absorbs little or no triglycerides from the oil.
The present invention also provides for a vegetable or animal oil refined by this process as well as an additive for animal feed comprising the silica used in this process.
The present invention may be better understood with reference to the embodiment shown in Figure 1 which is a schematic drawing of the process of the present invention and the equipment used to carry it out.
Absorbent silica can be used in treating unrefined oil to trap non-saponifiable compounds, mono and diglycerides, phosphoglycerides, and trace metals without using acidic or alkali washing, stripping with steam or filtration on clays. Thus, large quantities of aqueous wastes are not generated. The unrefined oil is treated with the absorbent silica and the oil is separated from the silica. The desired triglycerides remain in the oil phase and the silica is saturated with these other molecules. The saturated silica may hold back a small quantity of oil and becomes a good additive for animal feed since it has a good energy value.
Since it is these other compounds which produce the unpleasant taste and/or smell of oil particularly when using the oil in cooking, the use of the absorbent silica to trap these compounds and remove them from the oil improves the quality of the resulting refined oil. As well, this technology does not produce waste by-products. The resulting saturated silica which is removed from the oil can be reused as an additive for animal feed. The process is easy to use, clean, and does not require a large factory or significant investment in equipment.
The unrefined oil used in the process may be vegetable oil taken from fruits such as palm or olive oil or oils from seeds such as soya, rapeseed or sunflower oil. It may also be animal oils such as seal oil, whale oil, or fish oil.
Preferably, the silica used to refine the oil has an agglomerate size of between about 50 and about 120 μm and a surface area of between 50 and about 250 m2/g. This size and surface area is most efficient for the fixation of compounds in the oil mixture other than the triglycerides to produce a refined oil.
The refined oil may be separated from the silica by filtration or percolation. The resulting saturated silica which is separated from the oil may be used as an additive in animal feed without the need for further treatment.
This refining process is water-free and consequently does not generate aqueous water polluted effluents. The quantity of silica used is directly linked to the quality of the oil and the quantity of compounds other than triglycerides which are found in the unrefined oil.
In the separation step using percolation, silica is arranged on the bottom of a column and the oil is percolated on it under pressure. Saturation of the silica is detectable when the white silica turns to a brownish colour. The saturated silica is then removed from the column and may be used as an animal feed additive. The amount of silica required will depend upon the quality and characteristics of the unrefined oil. Generally, 1 kg of silica will refine 10-15 kg of unrefined oil.
The following examples are meant to be illustrative of preferred embodiments and are not intended to limit the scope of the present invention. Nariations of the invention will be readily apparent to a person skilled in the art and may be made without departing from the spirit or scope of the invention. These variations are intended to be within the scope of the present invention. The only limitations to the scope of the present invention are set out in the appended claims.
EXAMPLE 1 We put in a glass column (1) (diameter: 0.04m, height: 0.8m), 0.04 kg of absorbent silica (2) (average size of agglomerates: 60 μm, average surface area: 100 m2/g) retained by a cellulose filter (3) put on a metallic framework (4).
The soya oil stored in the container (5) has been obtained with a hexane extraction of soya seeds. The average value of the acidity of the raw oil expressed in % of weight of oleic acid is of 1.2% .
0.3 kg of oil is then placed in the column (1) at room temperature with a device included in a pump and a flood gate (7). A pressure of 16 p.s.i. is applied with a compressor (7) fitted with a flood gate (8) after closing the flood gate (6).
The average value of 0.7 1/h is measured for the flow rate.
The saturation of the silica is obtained for an addition of 0.2 kg of raw oil.
The refined oil has an acidity expressed in % weight of oleic acid lower than 0.1 % which allows its use in human feeding.
The saturated silica is removed from the column and directly used as an additive animal feeding.
EXAMPLE 2
We put in a glass column (1) (diameter: 0.04m, height: 0.8m) 0.04 kilo of absorbent silica (2) (average size of agglomerate 100 μm, average surface area: 190 m2/g) retained by a cellulose filter (3) put on a metallic framework (4). The sunflower oil stored in the container (5) has been obtained with a hexane extraction of dehulled seeds. The average value of the acidity of the raw oil expressed in % of weight of oleic acid is 1.1 % .
0.3 kg of oil is then placed in the column (1) at room temperature with a device including a pump and a flood gate (7). A pressure of 16 p.s.i. is applied with a compressor (7) fitted with a flood gate (8) after closing the flood gate (6). The average value of 1.8 1/h is measured for the flow rate.
The saturation of silica is obtained after another addition of 0.25 kg of raw sunflower oil.
The refined oil has an acidity expressed in % weight of oleic acid lower than 0.1 % which allows its use in human feeding. The saturated silica is removed from the column and directly used as an additive for animal feeding.
EXAMPLE 3
We put in a polyvinylchloride (P.N.C.) Column (1) (diameter: 0.5 m, height: 0.8 m) fitted with a window in plexiglass (width: 0.04 m, height: 0.7 m), 5 kilos of absorbent silica (2) (average size of agglomerates: 100 μm, average surface area: 190 m2/g) retained by a synthetic textile filter (3) put on a metallic framework (4).
The seal oil stored in the container (5) has been extracted from the blubbers of harp seals. The average value of the acidity expressed in % of weight of oleic acid is of 1.4% .
30 kg of oil is then placed in the column (1) at room temperature with a device including a pump and a flood gate (7).
A pressure of 12 p.s.i. is applied with a compressor (7) fitted with a flood gate (8) after closing the flood gate (6). The average value of 3.8 1/h is measured for the flood rate.
The saturation of silica is obtained after another addition of 27 kg of raw seal oil.
The refined oil has an acidity expressed in % weight of oleic acid lower than 0.1 % which allows its use in human feeding.
The saturated silica is removed from the column and directly used as an additive for animal feeding.
EXAMPLE 4
We put (scheme no. 1) in a polyvinylchloride (P.N.C.) Column (1) (diameter: 0.5 m, height: 0.8 m) fitted with a window of plexiglass (width: 0.04 m, height: 0.7 m), 5 kilos of absorbent silica (2) (average size of agglomerates: 100 μm average surface area: 190 m2/g) retained by a cellulose filter (3) put on a metallic framework (4).
The seal oil stored in the container (5) has been extracted from the blubbers of harp seals. The average value of the acidity expressed in % of weight of oleic acid is of 0.9% .
30 kg of oil are then placed in the column (1) at room temperature with a device including a pump and a flood gate (7).
A pressure of 12 p.s.i. is applied with a compressor (7) fitted with a flood gate after closing the flood gate (6). The average value of 4.2 1/h is measured for the flood rate.
The saturation of the silica is obtained after another addition of 35 kg of raw seal oil.
The refined oil has an acidity expressed in % weight of oleic acid lower than 0.1 % which allows its use in human feeding.
The saturated silica is removed from the column and directly used as an additive for animal feeding.

Claims

CLAIMS:
1. A process for treating animal or vegetable oil comprising the steps of treating the oil with absorbent silica; and separating the oil and silica to produce a refined oil wherein the silica substantially absorbs compounds from the oil other than triglycerides.
2. The process of claim 1 wherein the absorbent silica is a precipitated silica suitable for use in animal feed.
3. The process of claim 2 wherein the precipitated silica has an average agglomerated size of between 50 and 120 μm.
4. The process of claim 2 or 3 wherein the precipitated silica has an average surface area of between 50 and 250 m2/g.
5. The process of claim 1 wherein the silica absorbs less than 2% of triglycerides from the oil.
6. The process of any one of claims 1 to 4 wherein the step of treating the oil with the absorbent silica comprises percolating the oil through a silica bed in a column.
7. The process of claim 5 wherein the percolating step is carried out at about room temperature (20 °C).
8. The process of claim 1 wherein the vegetable oil is a fruit oil or a seed oil.
9. The process from claim 1 wherein the animal oil is oil of mammals or fish oil.
10. A refined oil produced by the process in claim 1. An additive for animal feed comprising silica separated from the refined oil in the process defined in claim 1.
AMENDED CLAIMS
[received by the International Bureau on 7 May 2001 (07.05.01); original claims 1-11 replaced by amended claims 1-9 (1 page)]
1. A process for treating substantially raw animal or vegetable oil comprising the steps of treating the oil with absorbent silica having an average surface area between 50 and 250 m /g; and separating the oil and silica to produce a refined oil and an animal feed additive comprising the silica which substantially absorbs compounds from the oil other than triglycerides.
2. The process of claim 1, wherein the absorbent silica is a precipitated silica suitable for use in animal feed.
3. The process of claim 2 wherein the precipitated silica has an average agglomerated size of between 50 and 120 μm.
4. The process of claim 1 wherein the silica absorbs less than 2% of triglycerides from the oil.
5. The process of any one of claims 1 to 4 wherein the step of treating the oil with the absorbent silica comprises percolating the oil through a silica bed in a column.
6. The process of claim 6 wherein the percolating step is carried out at about room temperature (20 °C).
7. The process of claim 1 wherein the vegetable oil is a fruit oil or a seed oil.
8. The process from claim 1 wherein the animal oil is oil of mammals or fish oil.
9. A refined oil produced by the process in claim 1.
PCT/CA2000/000028 2000-01-05 2000-01-05 Process for refining animal and vegetable oil WO2001049814A1 (en)

Priority Applications (4)

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PCT/CA2000/000028 WO2001049814A1 (en) 2000-01-05 2000-01-05 Process for refining animal and vegetable oil
CA002406910A CA2406910C (en) 2000-01-05 2000-01-05 Process for refining animal and vegetable oil
CNB008190410A CN1261553C (en) 2000-01-05 2000-01-05 Process for refining animal and vegetable oil
AU30279/00A AU3027900A (en) 2000-01-05 2000-01-05 Process for refining animal and vegetable oil

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CN102051262A (en) * 2010-11-16 2011-05-11 北京林业大学 Physical refining device for edible oil
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EP0185182A1 (en) * 1984-12-07 1986-06-25 W.R. Grace & Co.-Conn. Method for refining glyceride oils using amorphous silica
EP0234221A2 (en) * 1986-01-28 1987-09-02 W.R. Grace & Co.-Conn. Method for refining glyceride oils using acid-treated amorphous silica
EP0247411A1 (en) * 1986-05-14 1987-12-02 W.R. Grace & Co.-Conn. Method for treating caustic refined glyceride oils for removal of soaps and phospholipids
EP0361622A2 (en) * 1988-09-30 1990-04-04 Unilever N.V. Process for refining glyceride oil
CA2239393A1 (en) * 1998-07-09 2000-01-09 Caboto Seafoods Process for the production of refined edible oils and products for feedstuff animal industry from vegetable or animal raw oils and absorbent silicas

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
EP0185182A1 (en) * 1984-12-07 1986-06-25 W.R. Grace & Co.-Conn. Method for refining glyceride oils using amorphous silica
EP0234221A2 (en) * 1986-01-28 1987-09-02 W.R. Grace & Co.-Conn. Method for refining glyceride oils using acid-treated amorphous silica
EP0247411A1 (en) * 1986-05-14 1987-12-02 W.R. Grace & Co.-Conn. Method for treating caustic refined glyceride oils for removal of soaps and phospholipids
EP0361622A2 (en) * 1988-09-30 1990-04-04 Unilever N.V. Process for refining glyceride oil
CA2239393A1 (en) * 1998-07-09 2000-01-09 Caboto Seafoods Process for the production of refined edible oils and products for feedstuff animal industry from vegetable or animal raw oils and absorbent silicas

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR20190100375A (en) * 2019-01-23 2020-08-31 Pinchas Or Cold pressed olive oil having free fatty acid content
GR1009852B (en) * 2019-01-23 2020-10-29 Pinchas Or Cold pressed olive oil having free fatty acid content
EP3858958A1 (en) * 2020-01-28 2021-08-04 Or, Pinhas Cold pressed olive oil having free fatty acid content of less than 0.1%

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CN1261553C (en) 2006-06-28
CN1434849A (en) 2003-08-06
CA2406910C (en) 2010-03-09
CA2406910A1 (en) 2001-07-12

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