EP0672096A1 - Process for the refining of edible oils. - Google Patents

Process for the refining of edible oils.

Info

Publication number
EP0672096A1
EP0672096A1 EP94901805A EP94901805A EP0672096A1 EP 0672096 A1 EP0672096 A1 EP 0672096A1 EP 94901805 A EP94901805 A EP 94901805A EP 94901805 A EP94901805 A EP 94901805A EP 0672096 A1 EP0672096 A1 EP 0672096A1
Authority
EP
European Patent Office
Prior art keywords
oil
acid
temperature
flavour
heat treatment
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.)
Granted
Application number
EP94901805A
Other languages
German (de)
French (fr)
Other versions
EP0672096B1 (en
Inventor
Dalen Josef Petrus Van
Putte Karel P A M Van
Slooten Ronald Frederik Van
Arend Zwanenburg
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.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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 Unilever PLC, Unilever NV filed Critical Unilever PLC
Priority to EP94901805A priority Critical patent/EP0672096B1/en
Priority to DK94901805.5T priority patent/DK0672096T3/en
Publication of EP0672096A1 publication Critical patent/EP0672096A1/en
Application granted granted Critical
Publication of EP0672096B1 publication Critical patent/EP0672096B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C11B3/12—Refining fats or fatty oils by distillation
    • C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam
    • 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

Definitions

  • the present invention is concerned with a method for refining edible oils with the aim to avoid any refining step which is not considered natural.
  • the purification process of a crude edible oil usually comprises the removal of phospholipids (degumming) by means of water, acid and/or a sorbent.
  • Oils for which degumming was the first refining step still contain substances which have a negative influence on taste, smell and keepability. Those substances comprise inter alia free fatty acids and destabilising peroxydes.
  • deodorisation For the removal of several unwan ⁇ ted substances a process is used called deodorisation, which can be performed by stripping the oil with a strip ⁇ ping medium e.g. steam, at temperatures above 200°C. Stripping at such relatively high temperatures has the disadvantages that the oil may decompose and that unwanted and sometimes even toxic compounds are formed.
  • oils having a flavour which is much alike the natural flavour might be much appreciated by oil consumers.
  • the natural flavour of an oil may suffer from the presence of substances which contribute to an off-flavour perception.
  • the problem is to remove the flavour deteriorating substances while preserving and preferably increasing the flavour improving substances, without being hindered by the disadvantages of the processes according to the state of the art.
  • the object of the invention is to provide a mild and cheap refining method for the purification of edible oils and in the same time to provide oils with a specific flavour profile or even without any flavour (bland flavour) .
  • a method for refining a triglyceride oil which comprises acidifying the oil and removing substances which separate from the oil, followed by gas stripping of the oil at a temperature of 30-200°C, characterised in that the stripping treatment is preceded by a heat treatment, which consists of keeping the oil at a temperature of 30-180°C.
  • the flavour profile of the oil can be modified, including the complete removal of flavour.
  • the treatment of the invention is denoted as mild in contrast to the usual, demanding refining treatments comprising use of chemicals and/or high temperatures, such as alkaline deacidification, bleaching and deodorising at temperatures >200°C.
  • the temperature of the heat treatment preceding the stripping of the oil is in the range of 30-180°C, preferably 40-160°C and more preferably 60-160°C.
  • a suitable duration of the heat treatment may be in the range of one hour to one week, and preferably is between 5-40 h.
  • an adsorbent for example silica
  • silica may be admixed before filtration.
  • the duration of the treatment may be considerably shortened.
  • a suitable time is 14-15 h at a temperature of about 120°C, but with the additive the same effect is obtained within 7-8 h at the same temperature.
  • the amount of additive is 10-2000 ppm, preferably 100-2000 ppm calculated on oil.
  • a suitable amount is 500 ppm.
  • the acid may be dissolved or dispersed in a suitable harmless liquid.
  • natural acids are used, which may advantageously be selected from the group comprising citric acid, tartaric acid, malic acid, lactic acid and acetic acid.
  • Such natural acids are preferred as they contribute to the 'green' character of the refining method of the present invention.
  • natural extracts or compositions containing such acids are mentioned, like lemon-juice and the like.
  • the gas stripping is carried out according to methods known in the art with the proviso that preferably temperatures are practised which are moderate.
  • Moderate stripping temperatures suitable for the purpose of this invention are defined as being in the range of 30-200°C.
  • the temperature is in the range of 30-180°C and more preferably of 60-160°C.
  • a suitable period of time for gas stripping is 1-100 h, preferably 1-10 h.
  • the process according to the invention can be used with any kind of edible oil, either from animal or vegetable origin, it is particularly suitable for the purification of natural oils which have been obtained from a natural source and which after a mild refining treatment are ready for direct consumption such as sunflower oil, palm oil, olive oil, rape seed oil etc.
  • the present refining treatment may be combined with other known mild treatments such as washing with water, centrifu- ging or filtration, comprising membrane filtration.
  • Stripping is suitably effected by blowing steam or an inert gas such as nitrogen through the oil.
  • Bland flavour oils which have been obtained by the process of the invention are characterised by a free fatty acids content of at least 0.1 wt.% and a POV-value of less than 1 or even less than 0.5.
  • the oil may be featured as a "natural" oil for still another reason because the process can dispose of the usual bleaching treatment which removes carotenoids, so that the natural colour of the oil is retained.
  • the oils according to the invention can be used as such for consumption, or they may be processed further.
  • the invention therefore finally provides an edible composition containing a refined oil according to the invention.
  • the refined oils according to the invention may be used for example as ingredients in the preparation of edible compositions, such as water and oil emulsions, e.g. mayonnaise, dressings, fat spreads or processed cheese. Since the fat component of such products may be quite substantial, consequentially the flavour of the oil may contribute considerably to the flavour of the end product.
  • the oil refined according to the invention still has most of the original carotenoids present, whereas an oil refined according to the art has no carotenoids left.
  • the oil refined according to the invention can therefore be used as a natural colourant in products, e.g. spreads, having the advantage that no taste is present which could interfere with the desired taste of the product.
  • a reference sample (A) comprising the same oil, was subjected to the same degumming pretreatment, however, after filtration it was deodorised immediately by stripping with steam at 180°C for 5 h.
  • Another reference sample (B) comprising the same oil, was treated like sample (A) but stripped at 120°C for 5 h.
  • Example III the analytical data of the crude oil, the oil refined according to the invention and reference sample (A) are listed. After deodorization the fresh taste of the oil treated according to the invention and the reference sample A was excellent. After 6 months of storage at 15°C in plastic bottles the taste of both treated oils was still qualified as excellent.

Abstract

A method for refining triglyceride oils, preferably of natural origin. The method is particularly suitable for the refining of oils meant for direct consumption such as are sunflower oil, palm oil and olive oil. The method consists of a two-step treatment comprising a heating treatment and a subsequent stripping treatment. The stripping temperature is at 30-200 DEG C and the heating treatment consists of keeping the oil at an elevated but moderate temperature (30-180 DEG C). A stable oil results, which may be characterized further either by a specific flavour profile which may be appraised as natural and attractive or by the absence of any flavour.

Description

PROCESS FOR THE REFINING OF EDIBLE OILS
The present invention is concerned with a method for refining edible oils with the aim to avoid any refining step which is not considered natural.
Background of the invention
The purification process of a crude edible oil usually comprises the removal of phospholipids (degumming) by means of water, acid and/or a sorbent. Oils for which degumming was the first refining step still contain substances which have a negative influence on taste, smell and keepability. Those substances comprise inter alia free fatty acids and destabilising peroxydes. For the removal of several unwan¬ ted substances a process is used called deodorisation, which can be performed by stripping the oil with a strip¬ ping medium e.g. steam, at temperatures above 200°C. Stripping at such relatively high temperatures has the disadvantages that the oil may decompose and that unwanted and sometimes even toxic compounds are formed.
It has been realised that oils having a flavour which is much alike the natural flavour might be much appreciated by oil consumers. However, the natural flavour of an oil may suffer from the presence of substances which contribute to an off-flavour perception. The problem is to remove the flavour deteriorating substances while preserving and preferably increasing the flavour improving substances, without being hindered by the disadvantages of the processes according to the state of the art.
The invention
The object of the invention is to provide a mild and cheap refining method for the purification of edible oils and in the same time to provide oils with a specific flavour profile or even without any flavour (bland flavour) .
Surprisingly a refining process has been found comprising individual steps which are each considered as being natural, which in spite of the mild conditions applied, can afford a purified oil which is suited for direct consump¬ tion and which can be qualified as "natural". Its appearance and flavour are of a surprisingly high quality.
According to the invention a method is provided for refining a triglyceride oil which comprises acidifying the oil and removing substances which separate from the oil, followed by gas stripping of the oil at a temperature of 30-200°C, characterised in that the stripping treatment is preceded by a heat treatment, which consists of keeping the oil at a temperature of 30-180°C. With this method the flavour profile of the oil can be modified, including the complete removal of flavour.
Detailed description
Without wanted to be limited by theory it is believed that during the heating treatment decomposition occurs of unwanted oil substances, particularly destabilising peroxides, into harmless or even flavour imparting com- pounds such as ketones, aldehydes or alcohols.
The treatment of the invention is denoted as mild in contrast to the usual, demanding refining treatments comprising use of chemicals and/or high temperatures, such as alkaline deacidification, bleaching and deodorising at temperatures >200°C.
The temperature of the heat treatment preceding the stripping of the oil is in the range of 30-180°C, preferably 40-160°C and more preferably 60-160°C. A suitable duration of the heat treatment may be in the range of one hour to one week, and preferably is between 5-40 h. It goes without saying that when the process temperature is decreased, the process time should be increased to obtain sufficient effect. Therefore time and temperature should be properly attuned to each other so that a refined oil is obtained with a satisfying flavour.
On behalf of the removal of substances which separate from the oil an adsorbent, for example silica, may be admixed before filtration.
When the heat treatment according to the invention is carried out in the presence of an additive consisting of a relatively small amount of an acid and/or an antioxidant, preferably a tocopherol, the duration of the treatment may be considerably shortened.
For example, without the additive a suitable time is 14-15 h at a temperature of about 120°C, but with the additive the same effect is obtained within 7-8 h at the same temperature. The amount of additive is 10-2000 ppm, preferably 100-2000 ppm calculated on oil. A suitable amount is 500 ppm. On behalf of its addition the acid may be dissolved or dispersed in a suitable harmless liquid.
For acidifying the oil as mentioned above preferably natural acids are used, which may advantageously be selected from the group comprising citric acid, tartaric acid, malic acid, lactic acid and acetic acid. Such natural acids are preferred as they contribute to the 'green' character of the refining method of the present invention. In this respect also natural extracts or compositions containing such acids are mentioned, like lemon-juice and the like.
The gas stripping is carried out according to methods known in the art with the proviso that preferably temperatures are practised which are moderate. Moderate stripping temperatures suitable for the purpose of this invention are defined as being in the range of 30-200°C. Preferably the temperature is in the range of 30-180°C and more preferably of 60-160°C. A suitable period of time for gas stripping is 1-100 h, preferably 1-10 h. By properly attuning stripping time and temperature it is possible to obtain an oil with a characteristic and attractive flavour profile or even an oil being completely disposed of flavour (bland flavour) .
Although the process according to the invention can be used with any kind of edible oil, either from animal or vegetable origin, it is particularly suitable for the purification of natural oils which have been obtained from a natural source and which after a mild refining treatment are ready for direct consumption such as sunflower oil, palm oil, olive oil, rape seed oil etc.
The present refining treatment may be combined with other known mild treatments such as washing with water, centrifu- ging or filtration, comprising membrane filtration.
Stripping is suitably effected by blowing steam or an inert gas such as nitrogen through the oil.
During the heating period it is recommended to protect the oil from the outer air by a nitrogen blanket to prevent oil oxydation.
Bland flavour oils which have been obtained by the process of the invention are characterised by a free fatty acids content of at least 0.1 wt.% and a POV-value of less than 1 or even less than 0.5.
Thus, according to the invention, it is possible to improve and to attune or to remove the flavour of an edible oil applying mild processing conditions and without the addition of non-natural flavour imparting substances to the oil.
The oil may be featured as a "natural" oil for still another reason because the process can dispose of the usual bleaching treatment which removes carotenoids, so that the natural colour of the oil is retained.
The oils according to the invention can be used as such for consumption, or they may be processed further. The invention therefore finally provides an edible composition containing a refined oil according to the invention. The refined oils according to the invention may be used for example as ingredients in the preparation of edible compositions, such as water and oil emulsions, e.g. mayonnaise, dressings, fat spreads or processed cheese. Since the fat component of such products may be quite substantial, consequentially the flavour of the oil may contribute considerably to the flavour of the end product.
The oil refined according to the invention still has most of the original carotenoids present, whereas an oil refined according to the art has no carotenoids left. The oil refined according to the invention can therefore be used as a natural colourant in products, e.g. spreads, having the advantage that no taste is present which could interfere with the desired taste of the product.
The following Examples illustrate some specific embodiments of the present invention in greater detail. All percentages are % by weight on oil unless indicated otherwise.
Example 1
A 5 kg sample of a crude sunflower oil, containing phosphorous containing substances corresponding to 22 mg P/kg oil and free fatty acids corresponding to 0.69 %, was degummed at a temperature of 90°C. 0.10 % of a citric acid solution (50 % concentration) was added and after 15 min 0.2 % of water was added. After another 15 min 1.0 % of Trisyl (Davidson Chemical Division of W.R. Grace & Co.) was added and after 30 min water was removed from the mixture by drying at subatmospheric pressure until the water content was less than 0.1 %. After cooling the mixture to a temperature of 40°C, the solids were filtered off.
The degummed oil heated to 120°C oil was stirred for 15 h under N2-blanketing and subsequently stripped with steam at 120°C for 5 h. The flavour was completely removed. A reference sample (A) comprising the same oil, was subjected to the same degumming pretreatment, however, after filtration it was deodorised immediately by stripping with steam at 180°C for 5 h.
Another reference sample (B) comprising the same oil, was treated like sample (A) but stripped at 120°C for 5 h.
The analytical data of the crude oil, the oil refined by the method according to the invention and the reference sample (A) are listed in Table I. The fresh taste of the oil prepared according to the example and the oil of sample (A) was good. Even after 28 weeks of storage the taste was still acceptable for both exemplified oils. However, the oil sample (B) which had only been subjected to stripping at 120°C, was immediately rejected by a test panel.
Table I
Example 2
To a 5 kg sample of crude palm oil at a temperature of 90°C 0.10% of citric acid solution (50%) was added and after a residence time of 15 minutes 0.2% of water was added. After another 15 minutes 1.0% of Trisyl (Davidson Chemical Division of W.R. Grace & Co.) was added and 30 minutes later water was removed from the mixture by drying at subatmospheric pressure until the water content was less than 0.1%. After cooling the mixture to a temperature of 40°C, the solids were filtered off. The oil was then heated to 120°C, stirred for 15 hours under N2 blanketing and subsequently deodorized for 5 hours at 120°C. The flavour of the oil was completely removed.
For comparison, a reference sample containing the same oil was subjected to traditional palm oil refining comprising alkaline neutralisation and bleaching according to the art and, after filtration, deodorizing at 240°C for 2 hours. The fresh taste of both treated oils was good. The analytical data of the crude oil, the oil refined according to the invention and the reference are listed in Table II
Table II
Example 3
The same experiments as described in Example 1 were repeated on pilot plant scale (75 kg) with good result: in Table III the analytical data of the crude oil, the oil refined according to the invention and reference sample (A) are listed. After deodorization the fresh taste of the oil treated according to the invention and the reference sample A was excellent. After 6 months of storage at 15°C in plastic bottles the taste of both treated oils was still qualified as excellent.
Table III
Example 4
A crude sunflower oil was split in two equal samples. To one sample 0.1% citric acid (50% solution) was added, whereas to the second sample nothing was added. Subsequently both oils were heated under nitrogen for 10 hours at 120°C. In Table IV the POV values at different times are shown. This example clearly shows that the presence of citric acid during the heating treatment increases the decomposition rate of peroxides (indicated by decreasing POV-value) .
Table IV

Claims

C L A I M S
1. Method for refining a triglyceride oil comprising acidifying the oil and removing substances which separate from the oil, followed by gas stripping of the oil at a temperature 30-200°C, characterised in that the stripping treatment is preceded by a heat treatment, consisting of keeping the oil at a temperature of 30-180°C, preferably 40-160°C.
2. Method according to claim 1, characterised in that during the heat treatment the oil is kept at a temperature of 60-160°C.
3. Method according to one or more of claims 1-2, characterised in that the duration of the heat treatment is comprised between one hour to one week, preferably between 5-40 h.
4. Method according to one or more of claims 1-3, characterised in that during the heat treatment the oil contains an additive consisting of an acid and/or an anti- oxidant, which amounts to 10-2000 ppm calculated on oil.
5. Method according to one or more of claims, 1-4 characterised in that for acidifying the oil a natural acid is used.
6. Method according claim 5, characterised in that the natural acid is selected from the group comprising citric acid, tartaric acid, malic acid, lactic acid and acetic acid or natural extracts or compositions containing such acids.
7. Method according to one or more of the preceding claims, characterised in that, the gas stripping temperature is 30-180°C, preferably 60-160°C.
8. Method according to one or more of the preceding claims, characterised in that, the duration of the gas stripping is comprised between 1-100 h.
9. Method according to claim 8, characterised in that, the duration of the gas stripping is comprised between 1- 10 h.
10. Method according to on ore more of the preceding claims, characterised in that the oil is protected from oxidation during the heat treatment by a blanket of nitrogen.
11. Refined triglyceride oil obtainable by the method according to one or more of the preceding claims.
12. Refined triglyceride oil, characterised by a free fatty acids content of at least 0.1 wt.%, a POV-value less than 1 and a bland flavour.
13. Refined triglyceride oil according to claim 12, characterised by a POV-value less than 0.5.
14. Edible composition containing a refined triglyceride oil according to claims 11-13.
EP94901805A 1992-12-03 1993-11-16 Process for the refining of edible oils Expired - Lifetime EP0672096B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP94901805A EP0672096B1 (en) 1992-12-03 1993-11-16 Process for the refining of edible oils
DK94901805.5T DK0672096T3 (en) 1992-12-03 1993-11-16 Process for refining edible oils.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP92203750 1992-12-03
EP92203750 1992-12-03
EP94901805A EP0672096B1 (en) 1992-12-03 1993-11-16 Process for the refining of edible oils
PCT/EP1993/003213 WO1994012596A1 (en) 1992-12-03 1993-11-16 Process for the refining of edible oils

Publications (2)

Publication Number Publication Date
EP0672096A1 true EP0672096A1 (en) 1995-09-20
EP0672096B1 EP0672096B1 (en) 1997-05-07

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ID=8211097

Family Applications (1)

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EP94901805A Expired - Lifetime EP0672096B1 (en) 1992-12-03 1993-11-16 Process for the refining of edible oils

Country Status (11)

Country Link
EP (1) EP0672096B1 (en)
AT (1) ATE152761T1 (en)
AU (1) AU672858B2 (en)
CA (1) CA2150949C (en)
DE (1) DE69310543T2 (en)
DK (1) DK0672096T3 (en)
ES (1) ES2102806T3 (en)
MY (1) MY131379A (en)
TR (1) TR28200A (en)
WO (1) WO1994012596A1 (en)
ZA (1) ZA938754B (en)

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US6841182B1 (en) 1997-12-19 2005-01-11 Lipton, A Division Of Conopco, Inc. Olive oil containing food composition
US8609953B2 (en) 2006-03-10 2013-12-17 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same
US9480271B2 (en) 2009-09-15 2016-11-01 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same

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JPH07247495A (en) * 1994-03-09 1995-09-26 Fuji Oil Co Ltd Method for producing fatty oil highly containing carotene
AUPN023994A0 (en) * 1994-12-23 1995-01-27 Stotter, Gail Dawn A process for deodorising tea tree oil
IT1296002B1 (en) * 1995-04-06 1999-06-03 Paolo Bonazelli EXTRA-VIRGIN OLIVE OIL SOLIDIFIED IN ORDER TO OBTAIN A HIGH VOLUMETRIC EXPANSION AND RELATED PRODUCTION PROCESS
AU5816096A (en) * 1995-05-16 1996-11-29 Unilever Plc Method for refining an edible oil
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US6426423B1 (en) 1998-11-20 2002-07-30 I.P. Holdings Methods for treating phosphatide-containing mixtures
US6844458B2 (en) 1998-11-20 2005-01-18 Ip Holdings, L.L.C. Vegetable oil refining
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PT1013753E (en) * 1998-12-22 2006-06-30 Unilever Nv REFINING A VEGETABLE OIL
US6750359B1 (en) 2001-09-04 2004-06-15 Ip Holdings, L.L.C. Methods for treating deodorizer distillate
AU2004268196B2 (en) 2003-08-21 2010-03-04 Monsanto Technology Llc Fatty acid desaturases from primula
JP2007533310A (en) 2004-04-16 2007-11-22 モンサント テクノロジー エルエルシー Expression of fatty acid desaturase in maize
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CN115253780B (en) * 2022-08-10 2024-01-30 广西壮族自治区林业科学研究院 Aroma generating equipment and method for keeping original flavor of tea oil

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6841182B1 (en) 1997-12-19 2005-01-11 Lipton, A Division Of Conopco, Inc. Olive oil containing food composition
US8609953B2 (en) 2006-03-10 2013-12-17 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same
US9062319B2 (en) 2006-03-10 2015-06-23 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same
US9410161B2 (en) 2006-03-10 2016-08-09 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same
US9873887B2 (en) 2006-03-10 2018-01-23 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same
US10570406B2 (en) 2006-03-10 2020-02-25 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same
US9480271B2 (en) 2009-09-15 2016-11-01 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same
US9816100B2 (en) 2009-09-15 2017-11-14 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same
US10208315B2 (en) 2009-09-15 2019-02-19 Monsanto Technology Llc Soybean seed and oil compositions and methods of making same

Also Published As

Publication number Publication date
MY131379A (en) 2007-08-30
EP0672096B1 (en) 1997-05-07
AU5624694A (en) 1994-06-22
TR28200A (en) 1996-02-08
DE69310543T2 (en) 1997-09-04
ZA938754B (en) 1995-05-23
DE69310543D1 (en) 1997-06-12
ES2102806T3 (en) 1997-08-01
WO1994012596A1 (en) 1994-06-09
ATE152761T1 (en) 1997-05-15
CA2150949C (en) 2000-07-18
DK0672096T3 (en) 1997-11-03
AU672858B2 (en) 1996-10-17

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