EP2164627A1 - Procédé d'affinage modéré d'huiles végétales par terres de blanchiment naturelles - Google Patents

Procédé d'affinage modéré d'huiles végétales par terres de blanchiment naturelles

Info

Publication number
EP2164627A1
EP2164627A1 EP08773856A EP08773856A EP2164627A1 EP 2164627 A1 EP2164627 A1 EP 2164627A1 EP 08773856 A EP08773856 A EP 08773856A EP 08773856 A EP08773856 A EP 08773856A EP 2164627 A1 EP2164627 A1 EP 2164627A1
Authority
EP
European Patent Office
Prior art keywords
oil
bleaching
organic acid
bleaching earth
acid
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Withdrawn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
EP08773856A
Other languages
German (de)
English (en)
Inventor
Klaus Schurz
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.)
Sued Chemie AG
Original Assignee
Sued Chemie AG
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 Sued Chemie AG filed Critical Sued Chemie AG
Publication of EP2164627A1 publication Critical patent/EP2164627A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • B01J20/12—Naturally occurring clays or bleaching earth
    • 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
    • C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
    • 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
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/04—Refining fats or fatty oils by chemical reaction with acids

Definitions

  • the invention relates to a process for bleaching oils and fats.
  • bleaching earths are used to remove turbidity, discoloration or even to remove oxidation accelerators. Adsorptive cleaning significantly improves the taste, color and storage stability of oils and fats.
  • different classes of bleaching earths are used.
  • this group comprises acid-activated montmorillonites, wherein the acid activation is carried out in a complex process by dealuminating the crude clays with concentrated acids at high temperatures, usually at boiling heat. In this process, a bleaching earth product with a very high specific surface area and a large pore volume is obtained. Even the use of small amounts of these highly active _
  • Bleaching earth leads to noticeable cleaning of the crude oils.
  • Low amounts used in the bleaching process are desirable because the used bleaching earth binds to a residual amounts of oil, whereby the yield is reduced, and on the other hand the used bleaching earth must be disposed of in accordance with applicable regulations.
  • a disadvantage of these highly active bleaching earths is the fact that dealuminating with acid during production results in large amounts of acidic, high-salinity wastewater, which can only be treated or disposed of in complex processes.
  • the high costs for waste disposal and the complex production process justify the comparatively high prices of such highly active bleaching earths.
  • NABE Natural Active Bleaching Earth
  • SMBE surface activated systems
  • SMBE surface modified bleaching earth
  • a naturally active raw clay with small amounts of acid is applied and thus achieved an "in situ activation”.
  • Attapulgite and hormone-containing raw clays have proven particularly suitable for this process. These have a very high specific surface area of natural raw materials of about 100 to 180 m 2 / g and a pore volume of about 0.2 to 0.35 ml / g.
  • salts formed in the acid activation or unreacted portions of the acid are not washed out, they remain on the product and are at least partially deposited in the pores.
  • these acid-activated bleaching earths generally do not achieve the same efficiency as achieved by highly active bleaching earths (HPBE) produced by dealuminating with acid.
  • HPBE highly active bleaching earths
  • the simple manufacturing process allows a comparatively low-cost production, with no acid effluents being a particular advantage.
  • a bleaching earth composition comprising a neutral bleaching earth comprising attapulgite and smectite in a ratio in the range of 0.3: 1 to 1.5: 1, the proportion of attapulgite and smectite being at least 65% by weight. % of the bleaching earth corresponds. Further, the composition contains a polyvalent carboxylic acid having an even number of carboxyl groups arranged in pairs, the carboxyl groups each having an eclipsed configuration. - -
  • US 6,346,286 D1 claims a bleaching earth composition
  • a bleaching earth composition comprising a mixture of a particulate clay and a particulate polyvalent carboxylic acid wherein the carboxylic acid has a pKg in the range of 1 to 7 and is substantially free of salts of organic acids.
  • the clay has a moisture content of not more than 8% by weight based on the clay.
  • the polyvalent carboxylic acid is contained in a proportion in the range of 1 to 8 wt .-%, based on the composition in this.
  • 6,346,286 B1 describes a bleaching process in which the oil to be bleached is brought into contact with a particulate composition which comprises particles of a clay mineral and particles of at least one organic acid, the organic acid being substantially free of salts of the organic acid.
  • a suitable organic acid u.a. Called citric acid.
  • oils and fats each requires a careful selection of the bleaching earth used to obtain a satisfactory result. This applies in particular to naturally active as well as surface-modified bleaching earths. Fats and oils are extracted from natural sources. Therefore, fluctuations also occur between different batches of the same type of oil. Especially in small to medium-sized farms, different types of oil are refined in the same plant. In this case, it would be desirable to be able to individually adjust the bleaching earth individually to the crude oil to be purified by adjusting the amount of bleaching earth and its degree of activation in each case to the oil.
  • the present invention therefore an object of the invention to provide a method for bleaching oils and fats, which allows an individual vote of the bleaching earth on the oils and fats to be bleached.
  • This object is achieved in a method having the features of patent claim 1.
  • Advantageous embodiments of the method according to the invention are the subject of the dependent claims.
  • a natural or non-natural active bleaching earth is provided in a first container;
  • the bleaching earth is not previously sprayed with the acid in advance or ground together with the acid to achieve intimate mixing, but the bleaching earth and the solid organic acid are not mixed until immediately before the bleaching or individually metered to be added to the oil or fat to be bleached.
  • several bleacher sorts can be stored, which are then mixed for bleaching with a likewise stored solid acid. As a result, in an operation where various oils are refined, the - -
  • used bleaching earths are individually adjusted by selecting a suitable bleaching earth and this is then mixed with the also stored separately, preferably solid organic acid. This is particularly advantageous from a cost point of view for companies that process varying types of oil.
  • a naturally active or non-naturally active bleaching earth is understood as meaning a bleaching earth which has not yet undergone any activation steps, in particular not yet having been charged with an acid.
  • the bleaching earth may already have some activity in the bleaching of oils and fats without acid addition, but this bleaching effect can be enhanced by the addition of an organic acid.
  • These naturally active or non-natural bleaching earths are usually obtained from natural sources, ie mined in a mine. They are then dried and ground.
  • the naturally active or non-natural active bleaching earth provided in the process according to the invention is prepared per se in the customary manner, ie it has a customary moisture content and a customary fineness.
  • the moisture of the bleaching earth is usually adjusted to a water content in the range of 5 to 50 wt .-%, preferably 10 to 30 wt .-%.
  • the fineness of the bleaching earth is usually adjusted so that the residue is on a sieve of mesh size 63 microns in the range of about 5 to 45 wt .-%, preferably 20 to 40 wt .-%.
  • the mean particle diameter d 50 is preferably in the range from 15 to 45 ⁇ m, preferably from 20 to 40 ⁇ m, particularly preferably from 25 to 35 ⁇ m.
  • the naturally active or non-natural active bleaching earth is preferably provided in a form that it is free-flowing and flow out of the first container under the action of gravity _
  • the organic acid is provided in a second container.
  • the organic acid can be provided in dissolved form, preferably as an aqueous solution, or else as a solid powder. Again, the organic acid is preferably provided in a mold so that it can automatically flow out of the second container under the action of gravity.
  • organic acids which are harmless under food law.
  • organic acids which are in solid form at room temperature.
  • the organic acids preferably have at least two carboxyl groups.
  • Exemplary organic acids, which are advantageously present in solid form at room temperature, are citric acid, oxalic acid or even tartaric acid. The use of citric acid is particularly preferred.
  • the oil or fat to be bleached is provided in a mixing vessel.
  • This mixing container can be a preliminary container in which the oil or fat to be bleached is mixed with the naturally active or non-naturally active bleaching earth and the organic acid, in order subsequently to be transferred to a bleaching tank.
  • the mixing container can also be designed so that after the addition of the naturally active or non-natural active bleaching earth and the organic acid, the oil or fat can be bleached directly in the mixing container.
  • a mixing container conventional containers can be used.
  • These mixing containers are preferably equipped with a mixing device, for example in the form of an agitator.
  • a mixing device for example, can also act a steam injection, with which - -
  • superheated steam is introduced into the mixed with the bleaching earth and the organic acid oil.
  • the first container can be provided with a first controllable metering device and the second container with a second controllable metering device, which can each be controlled individually.
  • the metering can be carried out, for example, in such a way that a corresponding valve is provided on the first container or on the second container, through which the amount of naturally active or non-naturally active bleaching earth taken from the first container and the quantity of the product removed from the second container organic acid can be regulated in terms of quantity.
  • a special conveyor for example, in solid starting materials, a screw conveyor or liquid starting materials, a pump with which the flow rate of the added bleaching earth and the organic acid can be controlled.
  • the oil or fat to be bleached is bleached.
  • usual parameters are met.
  • the oil is heated, for example, at normal pressure to preferably 60 to 100 0 C, preferably 70 to 95 0 C, particularly preferably 80 to 9O 0 C and for a time of 10 to 40 minutes, preferably 15 to Stirred for 25 minutes.
  • the treatment time depends on the oil or fat to be treated and can be determined individually, for example by sampling during bleaching.
  • vacuum for example 30 to 150 mbar, preferably 60 to 100 mbar
  • the oil for about 10 to 60 minutes, preferably 20 to 40 minutes at about 80 to 14O 0 C, preferably 90 to 120 0 C stirred.
  • the bleaching earth is separated by, for example, the oil on with a Filtered filter covered with a paper filter is filtered.
  • the filtration is preferably carried out at elevated temperature, preferably in the range of 60 to 90 0 C, particularly preferably 70 to 85 ° C.
  • the amount of added organic acid can be tailored individually to the oil to be bleached and to the natural or non-natural bleaching earth used.
  • the appropriate amount can be determined by the expert by appropriate preliminary tests.
  • the proportion of the organic acid based on the weight of the naturally active or non-naturally active bleaching earth in a range from 0.1 to 10 wt .-%, preferably 1 to 5 wt .-%, particularly preferably 2 to 4 wt .-% selected.
  • the proportion of naturally active or non-naturally active bleaching earth added during bleaching depends on the oil to be bleached. By preliminary tests, however, the appropriate amount can be determined. Based on the weight of the oil to be bleached, the amount of bleaching earth added is preferably in the range from 0.01 to 10% by weight, preferably 0.1 to 5% by weight, particularly preferably 0.5 to 3% by weight. selected.
  • the organic acid is provided in solid form. If the acid is present in solid form, it is known to be stable even after prolonged storage, so that no loss of quality must be accepted. Furthermore, a solid powder can be metered very well, for example via a screw conveyor. As a further advantage, organic acids, when in solid form, are less aggressive, ie corrosion on the reservoirs occurs only to a minor extent, or more favorable materials can be used to make the reservoir. _
  • the solid organic acid should be able to flow out of the reservoir under the effect of gravity.
  • certain organic acids in particular citric acid
  • bridging occurs when the organic acid is stored in pure form.
  • the solid organic acid is mixed with a suitable flow aid.
  • the flow agents used are preferably those flow aids which are harmless under food law. Suitable examples are silicon dioxide, diatomaceous earth or talc.
  • a clay mineral is preferably used as flow aid, in particular preferably a naturally active or non-naturally active bleaching earth.
  • the flow aid is preferably added in an amount of 5 to 30% by weight based on the solid organic acid. If smaller amounts of flow aid are added, bridge formation in the reservoir can not be reliably suppressed. If higher amounts of flow aids are used, the amount of added solid increases, which is particularly disadvantageous if the flow aid involved does not simultaneously show a bleaching effect on the oil or fat to be treated.
  • the amount of the flow aid is selected in a range of 6 to 25 wt .-%, particularly preferably 7 to 15 wt .-%.
  • the bleaching earth and the organic acid can be added to the oil or fat to be bleached in various ways.
  • the organic acid and the naturally active or non-natural active bleaching earth are added separately to the mixing vessel to be mixed there with the oil or fat.
  • the organic acid can also be in the form - -
  • an aqueous solution of the organic acid is also used for other process steps, such as degumming of the oil. It is in this case then only a single reservoir required.
  • the bleaching earth and the solid organic acid are blended into a bleaching mixture just prior to addition to the oil or fat to be bleached.
  • the natural or non-natural active bleaching earth and the solid organic acid are removed to the desired amounts from the reservoirs and mixed intensively via a mixing device.
  • the resulting bleaching mixture is then added to the oil or fat to be bleached.
  • a screw conveyor is preferably used as a mixing device.
  • the screw conveyor is supplied with the bleaching earth and the solid organic acid. In the screw conveyor then an intimate mixing of bleaching earth and organic acid takes place.
  • the solid organic acid preferably has an average particle size D 50 in the range from 20 to 40 ⁇ m.
  • the oil or fat to be bleached is degummed to a phosphorus content of less than 15 ppm prior to the addition of the bleaching earth and the organic acid.
  • FIG. 1 shows schematically a device for carrying out the method according to the invention.
  • the crude oil which has been obtained, for example, by pressing corresponding plant seeds in an oil mill, is first subjected to drying and degassing (not shown), for example to remove dissolved oxygen from the oil.
  • the degassed crude oil which has a phosphorus content in the range of about 250 ppm, is then stored in a crude oil tank 1. From the crude oil tank 1, the crude oil is first fed to a degumming stage. For this purpose, the crude oil from the crude oil tank 1 is fed to a degumming tank 2.
  • Degumming may include pre-degumming as well as acid degumming.
  • pre-degumming water is added to the crude oil and the mixture is stirred at about 70 to 80 0 C at atmospheric pressure.
  • the aqueous lecithin phase is subsequently separated off.
  • the crude oil after pre-degumming has a phosphorus content in the range of about 100 to 200 ppm.
  • the acid degumming shown in FIG. 1 the pre-degummed oil in the degumming tank 2 is mixed with an acid.
  • the acid for example, a 50% citric acid can be used, which is taken from an acid storage tank 3.
  • the Entschleimungs technologyer 2 is provided with a stirrer 4, which allows intensive mixing of acid and crude oil.
  • the offset with the acid crude oil is heated in Entschleimungs effectiveer 2 to about 70 to 100 0 C and then stirred at atmospheric pressure.
  • Exemplary conditions are an acid amount of 0.06 wt% of a 50% citric acid, a treatment temperature of about 95 ° C and a treatment time of about 15 minutes.
  • water may still be added with the amount of water chosen at about 0.2% by weight to facilitate the separation of the gums.
  • the mixture is transferred to a centrifuge 5, in which the aqueous phase containing the mucilage is removed from the Slime crude oil is separated.
  • the mucilages are collected in a container 6.
  • the oil has a phosphorus content in the range of about 10 to 20 ppm. Degumming is necessary in combination with subsequent bleaching to reduce the proportion of phospholipids (phosphors) in the oil as well as the metals. If the degumming is dispensed with, the phosphorus and iron contents are often too high, even at sufficiently low Lovibond red / yellow color numbers in the refined oil.
  • the oil may optionally be dried and degassed (not shown). For phosphorous poor crude oils, such as palm oil, acid degumming may optionally be dispensed with and bleaching carried out directly.
  • the degummed oil is first collected in a storage tank 7 for degummed oil.
  • the degumming is followed by a bleaching of the oil, in which first a wet bleaching and then a vacuum bleaching can be carried out.
  • the degummed oil is transferred from the storage tank 7 into a mixing tank 8.
  • the mixing tank 8 the degummed oil is mixed with the bleaching earth and the citric acid.
  • bleaching earth which is stored in a bleacher silo 9, is transferred to a first feed container 10.
  • Powdered citric acid (a) which is mixed with a flow aid (b), for example a naturally active or non-naturally active bleaching earth, is stored in a second feed tank 11. From the first storage tank 10, the bleaching earth is fed to a screw conveyor 12.
  • the feed screw 12 is supplied from the second storage tank 11, the solid citric acid and the flow aid, so that the components are mixed in the screw conveyor 12.
  • the bleaching mixture is then fed to the mixing tank 8, where it is intensively mixed with the degummed oil by means of the agitator 13. It is not necessary, - -
  • only the bleaching earth can be transferred with the conveying screw 12 into the mixing tank 8, and separately, the citric acid from the second collecting container can be added directly to the mixing tank Delivery line 14 is provided, via which the citric acid is transferred directly into the mixing tank 8.
  • Delivery line 14 is provided, via which the citric acid is transferred directly into the mixing tank 8.
  • the degummed oil mixed with the bleaching earth and citric acid passes into a bleacher 15.
  • the oil is initially heated to atmospheric pressure of about 80 to 100 ° C. and stirred for about 20 minutes, then vacuum (for example 100 mbar) is applied and the oil is stirred for a further 30 minutes at about 90 to 120 ° C.
  • the oil is then fed to a filter 16 in which the used bleaching earth is bleached
  • a filter 16 for example, one with a Filterp apier occupied filter chute can be used.
  • the filtration is carried out at a temperature of about 80 0 C.
  • the oil can still be deodorized.
  • the deodorization is not shown in FIG.
  • superheated steam having an exit temperature of about 240 to 260 0 C, passed through the oil to remove free fatty acids and unpleasant flavors and odors.
  • the deodorization is carried out in vacuo at a pressure in the range of less than 5 mbar, preferably 1 to 3 mbar.
  • the oil After refining, the oil has a phosphorus content of less than 3 ppm and an iron content of less than 0.1 ppm.
  • a degummed rapeseed oil was added with 0.75% by weight of the bleaching agents listed in Table 1 and then for 30 minutes bleached at 105 0 C, wherein a reduced pressure of 60 mbar was applied.
  • a reduced pressure of 60 mbar was applied for deodorization.
  • hot water vapor which had an outlet temperature of 235 ° C., was passed through the mixture for 60 minutes.
  • the still hot oil is filtered through a paper filter to separate solids from the oil.
  • Table 1 The properties of the refined oils are summarized in Table 1.
  • NABE naturally active bleaching earth
  • Lovibond red color number The Lovibond red color number was determined in a 5% "cuvette (or crude ( * ) in a 1" cuvette) according to AOCS Cc 13b-45.
  • Chlorophyll A Chlorophyll A determination was according to AOCS Cc 13d-55.
  • IP Induction Period
  • Metrohm For this purpose, a constant air flow was passed through the heated sample and collected in a measuring vessel filled with distilled water. Oxidation results in short-chain organic acids, especially formic acid, which dissolve in the distilled water of the measuring vessel.
  • the conductivity of the distilled water was measured as a function of time. The conductivity initially remains constant and then increases. A tangent was created on the rising branch of the curve and the induction time was read on the x-axis.
  • Anisidine number (ANZ): The determination was carried out according to C-VI 6e (77)
  • Citric acid (H 3 Cit) is in proportion with natural bleaching earth (HUB) - -
  • the educts as well as the mixtures prepared are each transferred to a powder funnel, which is closed at the bottom with a watch glass.
  • the diameter of the Pulvertrichterauslaufes is 2.8 cm, the height is 14 cm. After removing the watch glass, it is observed - for the time being without any further mechanical action - whether the material drains very well or even well (assessment "++ to +"). If this is not the case, try tapping with (slightly) a little light to start a leak (if yes, judgment "x to o"). If there is no fluidity even then the assessment is "-").

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Inorganic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)

Abstract

L'invention concerne un procédé de blanchiment d'huiles ou de graisses. Dans ce but, on prépare une terre de blanchiment naturellement active ou naturellement inactive dans un premier récipient (10) et un acide organique dans un deuxième récipient (11). Dans un récipient de mélange (8), on fait réagir l'huile ou la graisse à blanchir avec la terre de blanchiment et l'acide organique, la terre de blanchiment et l'acide organique étant ajoutés séparément. Ensuite, on blanchit de la manière habituelle l'huile ou la graisse à blanchir.
EP08773856A 2007-07-04 2008-07-03 Procédé d'affinage modéré d'huiles végétales par terres de blanchiment naturelles Withdrawn EP2164627A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007031039A DE102007031039A1 (de) 2007-07-04 2007-07-04 Verfahren zur schonenden Raffination von Pflanzenölen mit Naturbleicherde
PCT/EP2008/005450 WO2009003710A1 (fr) 2007-07-04 2008-07-03 Procédé d'affinage modéré d'huiles végétales par terres de blanchiment naturelles

Publications (1)

Publication Number Publication Date
EP2164627A1 true EP2164627A1 (fr) 2010-03-24

Family

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Family Applications (1)

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EP08773856A Withdrawn EP2164627A1 (fr) 2007-07-04 2008-07-03 Procédé d'affinage modéré d'huiles végétales par terres de blanchiment naturelles

Country Status (5)

Country Link
US (1) US20100298587A1 (fr)
EP (1) EP2164627A1 (fr)
CA (1) CA2691861A1 (fr)
DE (1) DE102007031039A1 (fr)
WO (1) WO2009003710A1 (fr)

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Publication number Priority date Publication date Assignee Title
CA2696378C (fr) * 2009-03-13 2014-10-14 Woodrising Resources Ltd. Methode d'elimination de phosphates volatils presents dans des hydrocarbures
JP2011144343A (ja) * 2009-12-15 2011-07-28 Kao Corp 精製油脂の製造方法
CN106158274A (zh) * 2013-12-31 2016-11-23 赵牧青 铁芯变压器

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FR2290248A1 (fr) * 1974-11-07 1976-06-04 Union Minerale Produits antimottants pour substances pulverulentes ou granuleuses telles que les engrais
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Also Published As

Publication number Publication date
CA2691861A1 (fr) 2009-01-08
US20100298587A1 (en) 2010-11-25
WO2009003710A1 (fr) 2009-01-08
DE102007031039A1 (de) 2009-01-08

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