AU672858B2 - Process for the refining of edible oils - Google Patents
Process for the refining of edible oilsInfo
- Publication number
- AU672858B2 AU672858B2 AU56246/94A AU5624694A AU672858B2 AU 672858 B2 AU672858 B2 AU 672858B2 AU 56246/94 A AU56246/94 A AU 56246/94A AU 5624694 A AU5624694 A AU 5624694A AU 672858 B2 AU672858 B2 AU 672858B2
- Authority
- AU
- Australia
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000007670 refining Methods 0.000 title claims abstract description 16
- 239000008157 edible vegetable oil Substances 0.000 title description 7
- 239000000796 flavoring agent Substances 0.000 claims abstract description 27
- 235000019634 flavors Nutrition 0.000 claims abstract description 26
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 238000010438 heat treatment Methods 0.000 claims abstract description 14
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 235000015165 citric acid Nutrition 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 235000021588 free fatty acids Nutrition 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 235000006708 antioxidants Nutrition 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 63
- 235000019198 oils Nutrition 0.000 abstract description 63
- 235000019482 Palm oil Nutrition 0.000 abstract description 4
- 235000019486 Sunflower oil Nutrition 0.000 abstract description 4
- 239000002540 palm oil Substances 0.000 abstract description 4
- 239000002600 sunflower oil Substances 0.000 abstract description 4
- 239000004006 olive oil Substances 0.000 abstract description 2
- 235000008390 olive oil Nutrition 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000523 sample Substances 0.000 description 7
- 239000013074 reference sample Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 3
- 235000021466 carotenoid Nutrition 0.000 description 3
- 150000001747 carotenoids Chemical class 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000014059 processed cheese Nutrition 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
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 (14)
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.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP92203750 | 1992-12-03 | ||
| NLEP92203750 | 1992-12-03 | ||
| PCT/EP1993/003213 WO1994012596A1 (en) | 1992-12-03 | 1993-11-16 | Process for the refining of edible oils |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5624694A AU5624694A (en) | 1994-06-22 |
| AU672858B2 true AU672858B2 (en) | 1996-10-17 |
Family
ID=8211097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU56246/94A Ceased AU672858B2 (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) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07247495A (en) * | 1994-03-09 | 1995-09-26 | Fuji Oil Co Ltd | Process for producing fats and oils containing high 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 |
| WO1996036684A1 (en) * | 1995-05-16 | 1996-11-21 | Unilever N.V. | Method for refining an edible oil |
| WO1996041852A1 (en) * | 1995-06-12 | 1996-12-27 | Unilever N.V. | Mild refining of triglyceride oil |
| BR9813703A (en) | 1997-12-19 | 2000-10-10 | Unilever Nv | Spreadable paste composition containing oil, and processes for refining an olive oil, and for manufacturing a food composition. |
| US6426423B1 (en) | 1998-11-20 | 2002-07-30 | I.P. Holdings | Methods for treating phosphatide-containing mixtures |
| US6423857B1 (en) | 1998-11-20 | 2002-07-23 | I.P. Holdings | Methods for recovering fatty acids |
| US6441209B1 (en) | 1998-11-20 | 2002-08-27 | Ip Holdings, L.L.C. | Method for treating organic acid-treated phosphatides |
| US6844458B2 (en) | 1998-11-20 | 2005-01-18 | Ip Holdings, L.L.C. | Vegetable oil refining |
| US6172248B1 (en) * | 1998-11-20 | 2001-01-09 | Ip Holdings, L.L.C. | Methods for refining vegetable oils and byproducts thereof |
| 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 |
| ATE430802T1 (en) | 2003-08-21 | 2009-05-15 | Monsanto Technology Llc | FATTY ACID DESATURASES FROM PRIMULA |
| BRPI0509944A (en) | 2004-04-16 | 2007-09-25 | Monsanto Technology Llc | fatty acid desaturases expression in maize |
| TWI397582B (en) | 2004-11-04 | 2013-06-01 | Monsanto Technology Llc | Method for preparing oil composition |
| US20090300972A1 (en) * | 2006-02-28 | 2009-12-10 | Massoud Jalalpoor | Physical Refining Process Using Adsorbent Particles for the Production of Biodiesel Fuel |
| AU2007226680B2 (en) | 2006-03-10 | 2013-10-24 | Monsanto Technology Llc | Soybean seed and oil compositions and methods of making same |
| WO2009025542A1 (en) * | 2008-02-26 | 2009-02-26 | Ruslee Hussain | Improved process of refining crude vegetable oil and animal fats for biodiesel feedstock |
| US9480271B2 (en) | 2009-09-15 | 2016-11-01 | Monsanto Technology Llc | Soybean seed and oil compositions and methods of making same |
| CN115253780B (en) * | 2022-08-10 | 2024-01-30 | 广西壮族自治区林业科学研究院 | A fragrance-generating equipment and method for maintaining the original flavor of camellia oil |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51109908A (en) * | 1975-03-22 | 1976-09-29 | Asahi Denka Kogyo Kk | PAAMUYUNOSEISEIHO |
| JPS5488904A (en) * | 1977-12-27 | 1979-07-14 | Nisshin Oil Mills Ltd:The | Preparation of palm oil |
| AU632272B2 (en) * | 1988-03-11 | 1992-12-24 | Malaysian Palm Oil Board | Refining of edible oil |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51109907A (en) * | 1975-03-22 | 1976-09-29 | Asahi Denka Kogyo Kk | PAAMUYUNOSEISEIHO |
| DE3771670D1 (en) * | 1986-11-13 | 1991-08-29 | Cambrian Eng Group Ltd | METHOD FOR SLIMING TRIGLYCERIDOILS. |
| DE3839017A1 (en) * | 1988-11-18 | 1990-05-23 | Henkel Kgaa | Process for separating off by distillation undesirable constituents of natural fats/oils and derivatives thereof |
| ES2013206A6 (en) * | 1989-06-29 | 1990-04-16 | Espan Carburos Metal | OIL AND FAT DEODORIZATION PROCEDURE. |
-
1993
- 1993-11-16 AT AT94901805T patent/ATE152761T1/en not_active IP Right Cessation
- 1993-11-16 AU AU56246/94A patent/AU672858B2/en not_active Ceased
- 1993-11-16 EP EP94901805A patent/EP0672096B1/en not_active Expired - Lifetime
- 1993-11-16 DK DK94901805.5T patent/DK0672096T3/en active
- 1993-11-16 ES ES94901805T patent/ES2102806T3/en not_active Expired - Lifetime
- 1993-11-16 CA CA002150949A patent/CA2150949C/en not_active Expired - Fee Related
- 1993-11-16 WO PCT/EP1993/003213 patent/WO1994012596A1/en not_active Ceased
- 1993-11-16 DE DE69310543T patent/DE69310543T2/en not_active Expired - Fee Related
- 1993-11-23 ZA ZA938754A patent/ZA938754B/en unknown
- 1993-11-30 TR TR01088/93A patent/TR28200A/en unknown
- 1993-12-01 MY MYPI93002547A patent/MY131379A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51109908A (en) * | 1975-03-22 | 1976-09-29 | Asahi Denka Kogyo Kk | PAAMUYUNOSEISEIHO |
| JPS5488904A (en) * | 1977-12-27 | 1979-07-14 | Nisshin Oil Mills Ltd:The | Preparation of palm oil |
| AU632272B2 (en) * | 1988-03-11 | 1992-12-24 | Malaysian Palm Oil Board | Refining of edible oil |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69310543D1 (en) | 1997-06-12 |
| EP0672096A1 (en) | 1995-09-20 |
| DE69310543T2 (en) | 1997-09-04 |
| MY131379A (en) | 2007-08-30 |
| CA2150949C (en) | 2000-07-18 |
| ZA938754B (en) | 1995-05-23 |
| WO1994012596A1 (en) | 1994-06-09 |
| DK0672096T3 (en) | 1997-11-03 |
| ATE152761T1 (en) | 1997-05-15 |
| EP0672096B1 (en) | 1997-05-07 |
| ES2102806T3 (en) | 1997-08-01 |
| AU5624694A (en) | 1994-06-22 |
| TR28200A (en) | 1996-02-08 |
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