CA2023486A1 - Liquid triglyceride oil - Google Patents
Liquid triglyceride oilInfo
- Publication number
- CA2023486A1 CA2023486A1 CA 2023486 CA2023486A CA2023486A1 CA 2023486 A1 CA2023486 A1 CA 2023486A1 CA 2023486 CA2023486 CA 2023486 CA 2023486 A CA2023486 A CA 2023486A CA 2023486 A1 CA2023486 A1 CA 2023486A1
- Authority
- CA
- Canada
- Prior art keywords
- triglyceride oil
- oil
- fatty acid
- weight
- triglyceride
- 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.)
- Abandoned
Links
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims description 61
- 239000007788 liquid Substances 0.000 title abstract description 7
- 239000003921 oil Substances 0.000 claims description 87
- 235000019198 oils Nutrition 0.000 claims description 87
- 235000021281 monounsaturated fatty acids Nutrition 0.000 claims description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 16
- 229930195729 fatty acid Natural products 0.000 claims description 16
- 239000000194 fatty acid Substances 0.000 claims description 16
- 150000004665 fatty acids Chemical class 0.000 claims description 15
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 6
- 235000019486 Sunflower oil Nutrition 0.000 claims description 5
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 239000002600 sunflower oil Substances 0.000 claims description 5
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 235000006708 antioxidants Nutrition 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- -1 carbon fatty acids Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 claims description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000473 propyl gallate Substances 0.000 claims description 2
- 235000010388 propyl gallate Nutrition 0.000 claims description 2
- 229940075579 propyl gallate Drugs 0.000 claims description 2
- 239000004250 tert-Butylhydroquinone Substances 0.000 claims description 2
- 235000019281 tert-butylhydroquinone Nutrition 0.000 claims description 2
- 239000011732 tocopherol Substances 0.000 claims description 2
- 229930003799 tocopherol Natural products 0.000 claims description 2
- 235000019149 tocopherols Nutrition 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 claims description 2
- 241000208818 Helianthus Species 0.000 claims 1
- 235000003222 Helianthus annuus Nutrition 0.000 claims 1
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract description 4
- 239000008158 vegetable oil Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 description 11
- 239000000306 component Substances 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 238000009882 destearinating Methods 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 235000012020 french fries Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005481 linolenic acid group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
Abstract
ABSTRACT
Liquid vegetable oils having desirable cis:trans configuration are obtained herein.
Liquid vegetable oils having desirable cis:trans configuration are obtained herein.
Description
2~234~6 TITLE: LIQUID TRIGLYCERIDE OIL
FIELD OF THE INVENTION
This invention relates to triglyceride oils typically obtained from vegetable sources and which have been hydrogenated to provide stability without adversely affecting flavor and other desirable characteristics of the liquid oil.
INTRODUCTION TO THE INVENTION
It is known that vegetable oils which are triglycer ides maybe hydrogenated to obtain a completely saturated product. A triglyceride oil is one which is the triester of glycerin and the corresponding fatty acid. The diffi-culty in hydrogenating an oil is that the desirable mono unsaturated content of the oil may be removed when the polyunsaturated content is removed. That is, it is desirable to maintain a single double bond such as that corresponding to oleic acid in each fatty acid component in a triglyceride. It is not desirable to maintain linoleic or linolenic acid residues within an edible vegetable oil used for frying. The latter two mentioned acids contribute to oxidative instability or rancidity.
Typical processing of various oils include those described in United States Patent 4,804,555 issued Febru-ary 14, 1989 to Marschner et al. A process for preparing a butter like spread is found in the disclosure of Wiles et al in United States Patent 4,606,926 issued August 19, 1986.
2023~86 The hydrogenation of long chain olefinic oils withRaney catalyst is described by Gray et al in United States Patent 4,584,139 issued April 22, 1986. The selective reduction o~ edible fats and oils using a phosphorus modified nickel catalyst is described by Qualeatti in United States Patent 4,547,319 issued October 15, 1985.
The treatment of vegetable oils is also described in Unites States Patent 4,588,745 issued May 13, 1986 to Bessler.
The foregoing patents deal generally with obtaining oils and various aspects of processing to hydrogenate such oils. The present invention deals with obtaining oils having desirable mouth feel, flavor, oxidative stability, and a desirable Solid Fat Index.
The triglycerides of the present invention may be obtained without crystallization of the oil. The products are sufficiently stable that they do not require, or de sirably only have present a small amount of, conventional antioxidants.
Throughout the specification and claims percentages and ratios are by weight, temperatures are in degrees Celsius and pressures are in KPa gauge unless otherwise indicated. The references cited herein are incorporated by reference to the extent that they are applicable. The various numerical values given herein may be combined.
SUMMARY OF THE INVENTION
The first aspect of this invention is a triglyceride oil wherein the fatty acid components of the triglyceride are greater than 90~ by weight of C18; the monounsaturated fatty acid content of the triglyceride oil is at least 80~
by weight; the polyunsaturated fatty acid com ponents in the triglyceride oil are less than 1.5% by weight; the saturated fatty acid content of the triglycer ide oil is less than 15~ and the cis:trans ratio of the C18 monounsaturated fatty acid content of the triglycer ide oil is from 15:1 to 3:1.
2023~86 A further aspect of the present invention is a tri-glyceride oil wherein the fatty acid components of the triglyceride oil are greater than 90% by weight of C18;
the monounsaturated fatty acid content of the triglyceride oil is at least 80% by weight the polyunsaturated fatty acid components în the triglyceride oil are less than 1.5%
by weight; the saturated fatty acid content of the tri-glyceride oil is less than 15% by weight and the cis:trans ratio of the monounsaturated fatty acid content of the triglyceride oil is from 15:1 to 3:1; wherein the trigylceride oil has a Solid Fat Index of less than 10 at 50F (10C); the triglyceride oil has a minimum AOM value of 100 hours; and the cis monounsaturated fatty acid content of the trigylceride oil is from 65% to 80% by weight.
DETAILED DESCRIPTION OF THE INVENTION
The triglyceride oils of the present invention as previously described contain greater than 90% by weight of C18 fatty acid substituents, preferably greater than 92%.
The monounsaturated fatty acid content of the triglycer-ide oil is typically at least 80% and more preferably greater than 85~ and more preferably greater than 90~ by weight. The polyunsaturated fatty acid components in the triglyceride oil are typically les~ than 1.5%, often less than 1% by weight. The saturated fatty acid content in the oil is less than 15%, and often less than 12%, and most preferably less than 8% by weight. It is desirable that the fatty acid components of the triglyceride are less than 10% by weight, preferably 6% by weight or less of 16 carbon fatty acids.
An important feature of the present invention result-ing from the particular hydrogenation to obtain the liquid oil is the cis:trans ratio of the monounsaturated fatty acids. That is when a polyunsaturate is hydrogenated there is rearrangement and either the cis or trans mono unsaturated fatty acid may result. It has been found desirable herein that the ultimate cis:trans ratio should be from 15:1 to 3:1; preferably from 12:1 to 4:1. This ratio is dimensionless and refers to the fatty acids in the triglyceride. As the C18 components predominate the foregoing is particularly applicable to the oleic components. The desirable benefits of the oils of the present are so obtained.
It is also desirable in the present invention that the fatty acids having a 20 or more carbon atoms therein are less than 3% by weight of the triglyceride oil. It is desirable that substantially all of the unsaturated fatty acid components in the triglyceride oil contain 18 carbon atoms.
A typical source for the oil described herein is sunflower seeds, however, most any highly monounsaturated fatty acid oil may be utilized to obtain the triglyceride oils of the present invention. The starting sunflower oil typically contains at least 70% (and typically at least 80%) by weight of oleci~ fatty acids in the triglyceride triester.
It will also be observed that the cis monounsaturated fatty acid content is typically from 6S to 85% by weight of the finished triglyceride oil. That is, substantially 2S no free fatty acids are present in the edible oil.
The liquid vegetable oils of the present invention are often obtained without utilizing crystallization (winterizing) of the oil. The avoidance of winterizing is desirable as the cost of the crystallizing through cooling is avoided.
As will be described later herein the triglyceride oils of the present invention have an Active Oxygen Method (AOM) value of 100 hours or greater. A measure of the liquidity of the oil described herein is by the Solid Fat Index (SFI) being less than 10 at 50F (10C). The AOM
2~2348~
test employed is A.O.C.S. Method CD 12-57 revised 1981.
The SFI test is A.O.C.S. CD 10-57 revised in 1974.
Lastly, whereas many triglyceride oils require a supplemental antioxidant the oils of the present invention do not require an antioxidant for stability against ran cidity. However, it may be desirable to include in the oils of the present invention small amounts e.g. up to 1~
of a material such as butylated hydroxyanisole, butylated hydroxytoluene, tertiary butyl hydroquinone, tocopherols, and propyl gallate and mixtures thereof.
To obtain the oils of the present invention it is desirable to utilize a catalyst which is capable of giving the desired cis:trans configuration of the monounsaturated fatty acid content in the oil. To accomplish the foregoing it has been found that a catalyst described as Nysosel 325 from the Harshaw Division of the Engelhard Corporation of Cleveland, Ohio provides, under the conditions described, the desired cis:trans content, AOM
and SFI value. The Nysosel catalyst is a nickel hydrogenation catalyst. The composition of the catalyst is typically 22% by weight nickel with an inert support system of about 8~ by weight. The catalyst system also contains about 70~ by weight stearine.
PROCESSING
The processing aspect of the present invention involves mixing of 0.5 to 50 grams of the active catalyst with 1,000 grams of the oil to be hydrogenated. The oil and catalyst are premixed and the mixture temperature is then raised to 125C to 200C. The introduction of hydrogen utilizing a nitrogen blanket is then conducted.
The hydrogen is maintained at a pressure of about 20 KPa to 500 KPa and the temperature of hydrogenation is from 150C to 195C for a period of 0.25 to 5 hours. By following the foregoing description and utilizing the nickel catalyst as described herein the products so described are obtained.
2Q23~,~fi What follows is an example of the present invention:
EXAMPLE I
A liquid triglyceride oil is prepared by first cleani~g a 4 liter stainless steel reaction system. The system is vented to the aix and a catalyst slurry comprising 1.9 grams of the nickel catalyst in 100 grams of sunflower oil having an oleic acid content of 80~ is charged. The charging equipment is flushed with an additional 200 grams of the previously described sunflower oil to ensure that all the catalyst is introduced to the reaction vessel.
An additional 2440 grams of the sunflower oil i5 then added to the reactor which is then sealed and pressure tested to 410 KPa (60 psig).
The reaction vessel is equipped with a stirring device which is maintained at 1300 rpm. The system is then evacuated to 2 KPa (15 mm Hg) to remove any entrained air. The contents of the reaction vessel are then heated to 177C (350F) for 30 minutes or longer. When the contents of the reaction vessel have achieved the 177C
temperature the system is pressuriæed with hydrogen to 35 KPa (5 psig). The temperature and pressure are maintained until the refractive index measured at 48C is lowered from 1.4595 to 1.4584. The refractive index is measured by A.O.C.S. method CC 7-25 Reapproved 1973.
Any remaining excess hydrogen is then vented to the atmosphere and a nitrogen purge is employed to remove any entrained hydrogen. The hydrogenated oil is cooled to 87C to 94C (190-200F) over a period of approximately 15 minutes. The oil is then filtered utilizing 30 grams of diatomaceous earth.
The oil obtained from the above process has a refrac-tive index of 1.4582 to 1.4586, a linoleic acid content of less than 1%, and AOM of 100 as a minimum and a Mettler Dropping Point of 10C tp 18C (50-65F). The Mettler Dropping Poiint Test is AOCS test Cc 18-80.
202~86 EXAMPLE II
The oil obtained from the preceding example is used as a deep frying oil. French fries when fried in the above described are crispy without any noticeable after-taste. The high AOM value of the oils indicate that whenused on a commercial basis that the oil will not need to be discarded as frequently because of rancidity.
FIELD OF THE INVENTION
This invention relates to triglyceride oils typically obtained from vegetable sources and which have been hydrogenated to provide stability without adversely affecting flavor and other desirable characteristics of the liquid oil.
INTRODUCTION TO THE INVENTION
It is known that vegetable oils which are triglycer ides maybe hydrogenated to obtain a completely saturated product. A triglyceride oil is one which is the triester of glycerin and the corresponding fatty acid. The diffi-culty in hydrogenating an oil is that the desirable mono unsaturated content of the oil may be removed when the polyunsaturated content is removed. That is, it is desirable to maintain a single double bond such as that corresponding to oleic acid in each fatty acid component in a triglyceride. It is not desirable to maintain linoleic or linolenic acid residues within an edible vegetable oil used for frying. The latter two mentioned acids contribute to oxidative instability or rancidity.
Typical processing of various oils include those described in United States Patent 4,804,555 issued Febru-ary 14, 1989 to Marschner et al. A process for preparing a butter like spread is found in the disclosure of Wiles et al in United States Patent 4,606,926 issued August 19, 1986.
2023~86 The hydrogenation of long chain olefinic oils withRaney catalyst is described by Gray et al in United States Patent 4,584,139 issued April 22, 1986. The selective reduction o~ edible fats and oils using a phosphorus modified nickel catalyst is described by Qualeatti in United States Patent 4,547,319 issued October 15, 1985.
The treatment of vegetable oils is also described in Unites States Patent 4,588,745 issued May 13, 1986 to Bessler.
The foregoing patents deal generally with obtaining oils and various aspects of processing to hydrogenate such oils. The present invention deals with obtaining oils having desirable mouth feel, flavor, oxidative stability, and a desirable Solid Fat Index.
The triglycerides of the present invention may be obtained without crystallization of the oil. The products are sufficiently stable that they do not require, or de sirably only have present a small amount of, conventional antioxidants.
Throughout the specification and claims percentages and ratios are by weight, temperatures are in degrees Celsius and pressures are in KPa gauge unless otherwise indicated. The references cited herein are incorporated by reference to the extent that they are applicable. The various numerical values given herein may be combined.
SUMMARY OF THE INVENTION
The first aspect of this invention is a triglyceride oil wherein the fatty acid components of the triglyceride are greater than 90~ by weight of C18; the monounsaturated fatty acid content of the triglyceride oil is at least 80~
by weight; the polyunsaturated fatty acid com ponents in the triglyceride oil are less than 1.5% by weight; the saturated fatty acid content of the triglycer ide oil is less than 15~ and the cis:trans ratio of the C18 monounsaturated fatty acid content of the triglycer ide oil is from 15:1 to 3:1.
2023~86 A further aspect of the present invention is a tri-glyceride oil wherein the fatty acid components of the triglyceride oil are greater than 90% by weight of C18;
the monounsaturated fatty acid content of the triglyceride oil is at least 80% by weight the polyunsaturated fatty acid components în the triglyceride oil are less than 1.5%
by weight; the saturated fatty acid content of the tri-glyceride oil is less than 15% by weight and the cis:trans ratio of the monounsaturated fatty acid content of the triglyceride oil is from 15:1 to 3:1; wherein the trigylceride oil has a Solid Fat Index of less than 10 at 50F (10C); the triglyceride oil has a minimum AOM value of 100 hours; and the cis monounsaturated fatty acid content of the trigylceride oil is from 65% to 80% by weight.
DETAILED DESCRIPTION OF THE INVENTION
The triglyceride oils of the present invention as previously described contain greater than 90% by weight of C18 fatty acid substituents, preferably greater than 92%.
The monounsaturated fatty acid content of the triglycer-ide oil is typically at least 80% and more preferably greater than 85~ and more preferably greater than 90~ by weight. The polyunsaturated fatty acid components in the triglyceride oil are typically les~ than 1.5%, often less than 1% by weight. The saturated fatty acid content in the oil is less than 15%, and often less than 12%, and most preferably less than 8% by weight. It is desirable that the fatty acid components of the triglyceride are less than 10% by weight, preferably 6% by weight or less of 16 carbon fatty acids.
An important feature of the present invention result-ing from the particular hydrogenation to obtain the liquid oil is the cis:trans ratio of the monounsaturated fatty acids. That is when a polyunsaturate is hydrogenated there is rearrangement and either the cis or trans mono unsaturated fatty acid may result. It has been found desirable herein that the ultimate cis:trans ratio should be from 15:1 to 3:1; preferably from 12:1 to 4:1. This ratio is dimensionless and refers to the fatty acids in the triglyceride. As the C18 components predominate the foregoing is particularly applicable to the oleic components. The desirable benefits of the oils of the present are so obtained.
It is also desirable in the present invention that the fatty acids having a 20 or more carbon atoms therein are less than 3% by weight of the triglyceride oil. It is desirable that substantially all of the unsaturated fatty acid components in the triglyceride oil contain 18 carbon atoms.
A typical source for the oil described herein is sunflower seeds, however, most any highly monounsaturated fatty acid oil may be utilized to obtain the triglyceride oils of the present invention. The starting sunflower oil typically contains at least 70% (and typically at least 80%) by weight of oleci~ fatty acids in the triglyceride triester.
It will also be observed that the cis monounsaturated fatty acid content is typically from 6S to 85% by weight of the finished triglyceride oil. That is, substantially 2S no free fatty acids are present in the edible oil.
The liquid vegetable oils of the present invention are often obtained without utilizing crystallization (winterizing) of the oil. The avoidance of winterizing is desirable as the cost of the crystallizing through cooling is avoided.
As will be described later herein the triglyceride oils of the present invention have an Active Oxygen Method (AOM) value of 100 hours or greater. A measure of the liquidity of the oil described herein is by the Solid Fat Index (SFI) being less than 10 at 50F (10C). The AOM
2~2348~
test employed is A.O.C.S. Method CD 12-57 revised 1981.
The SFI test is A.O.C.S. CD 10-57 revised in 1974.
Lastly, whereas many triglyceride oils require a supplemental antioxidant the oils of the present invention do not require an antioxidant for stability against ran cidity. However, it may be desirable to include in the oils of the present invention small amounts e.g. up to 1~
of a material such as butylated hydroxyanisole, butylated hydroxytoluene, tertiary butyl hydroquinone, tocopherols, and propyl gallate and mixtures thereof.
To obtain the oils of the present invention it is desirable to utilize a catalyst which is capable of giving the desired cis:trans configuration of the monounsaturated fatty acid content in the oil. To accomplish the foregoing it has been found that a catalyst described as Nysosel 325 from the Harshaw Division of the Engelhard Corporation of Cleveland, Ohio provides, under the conditions described, the desired cis:trans content, AOM
and SFI value. The Nysosel catalyst is a nickel hydrogenation catalyst. The composition of the catalyst is typically 22% by weight nickel with an inert support system of about 8~ by weight. The catalyst system also contains about 70~ by weight stearine.
PROCESSING
The processing aspect of the present invention involves mixing of 0.5 to 50 grams of the active catalyst with 1,000 grams of the oil to be hydrogenated. The oil and catalyst are premixed and the mixture temperature is then raised to 125C to 200C. The introduction of hydrogen utilizing a nitrogen blanket is then conducted.
The hydrogen is maintained at a pressure of about 20 KPa to 500 KPa and the temperature of hydrogenation is from 150C to 195C for a period of 0.25 to 5 hours. By following the foregoing description and utilizing the nickel catalyst as described herein the products so described are obtained.
2Q23~,~fi What follows is an example of the present invention:
EXAMPLE I
A liquid triglyceride oil is prepared by first cleani~g a 4 liter stainless steel reaction system. The system is vented to the aix and a catalyst slurry comprising 1.9 grams of the nickel catalyst in 100 grams of sunflower oil having an oleic acid content of 80~ is charged. The charging equipment is flushed with an additional 200 grams of the previously described sunflower oil to ensure that all the catalyst is introduced to the reaction vessel.
An additional 2440 grams of the sunflower oil i5 then added to the reactor which is then sealed and pressure tested to 410 KPa (60 psig).
The reaction vessel is equipped with a stirring device which is maintained at 1300 rpm. The system is then evacuated to 2 KPa (15 mm Hg) to remove any entrained air. The contents of the reaction vessel are then heated to 177C (350F) for 30 minutes or longer. When the contents of the reaction vessel have achieved the 177C
temperature the system is pressuriæed with hydrogen to 35 KPa (5 psig). The temperature and pressure are maintained until the refractive index measured at 48C is lowered from 1.4595 to 1.4584. The refractive index is measured by A.O.C.S. method CC 7-25 Reapproved 1973.
Any remaining excess hydrogen is then vented to the atmosphere and a nitrogen purge is employed to remove any entrained hydrogen. The hydrogenated oil is cooled to 87C to 94C (190-200F) over a period of approximately 15 minutes. The oil is then filtered utilizing 30 grams of diatomaceous earth.
The oil obtained from the above process has a refrac-tive index of 1.4582 to 1.4586, a linoleic acid content of less than 1%, and AOM of 100 as a minimum and a Mettler Dropping Point of 10C tp 18C (50-65F). The Mettler Dropping Poiint Test is AOCS test Cc 18-80.
202~86 EXAMPLE II
The oil obtained from the preceding example is used as a deep frying oil. French fries when fried in the above described are crispy without any noticeable after-taste. The high AOM value of the oils indicate that whenused on a commercial basis that the oil will not need to be discarded as frequently because of rancidity.
Claims (15)
1. A triglyceride oil wherein the fatty acid components of the triglyceride are greater than 90% by weight of C18; the monounsaturated fatty acid content of the triglyceride oil is at least 80% by weight; the poly-unsaturated fatty acid components in the triglyceride oil are less than 1.5% by weight; the saturated fatty acid content of the triglyceride oil is less than 15% by weight and the C18 cis:trans ratio of the monounsaturated fatty acid content of the triglyceride oil is from 15:1 to 3:1.
2. The triglyceride oil of claim 1 wherein the fatty acid content of the triglyceride oil is less than 3%
by weight of those fatty acids having 20 or greater carbon atoms.
by weight of those fatty acids having 20 or greater carbon atoms.
3. The triglyceride oil of claim 1 wherein the unsaturated fatty acid components of the triglyceride are substantially 18 carbon atoms or greater.
4. The oil of claim 1 wherein the Solid Fat Index is less than 10 at 50°F (10°C).
5. The triglyceride oil of claim 1 wherein the oil is derived from sunflower.
6. The triglyceride oil of claim 1 wherein the fatty acid components of the triglyceride are 10% by weight or less of 16 carbon fatty acids.
7. The triglyceride oil of claim 1 wherein the mono unsaturated cis:trans ratio is from 12:1 to 4:1.
8. The triglyceride oil of claim 5 wherein the fatty acids in the starting sunflower oil are greater than 85% by weight monounsaturated.
9. The triglyceride oil of claim 1 wherein the saturated fatty acid content of the triglyceride is less than 12% by weight.
10. The triglyceride oil of claim 1 wherein the cis monounsaturated fatty acid content is from 65 to 85% by weight.
11. The triglyceride oil of claim 1 wherein the AOM
value is greater than about 100 hours.
value is greater than about 100 hours.
12. The triglyceride oil of claim 1 containing an anti-oxidant.
13. The triglyceride oil of claim 1 which is ob-tained without crystallization.
14. The triglyceride oil of claim 12 wherein the oil contains a member selected from the group consisting of butylated hydroxyanisole; butylated hydroxytoluene;
tertiary butyl hydroquinone; tocopherols; and propyl gallate and mixtures thereof.
tertiary butyl hydroquinone; tocopherols; and propyl gallate and mixtures thereof.
15. A triglyceride oil wherein the fatty acid components of the triglyceride oil are greater than 90% by weight of C18; the monounsaturated fatty acid content of the triglyceride oil is at least 80% by weight; the polyunsaturated fatty acid components in the triglyceride oil are less than 1.5% by weight; the saturated fatty acid content of the triglyceride oil is less than 15% by weight and the cis:trans ratio of the monounsaturated fatty acid content of the triglyceride oil is from 15:1 to 3:1;
wherein the triglyceride oil has a Solid Fat Index of less than 10 at 50°F (10°C); the triglyceride oil has an AOM
minimum value of 100 hours; and the cis monounsaturated fatty acid content of the triglyceride oil is from 65% to 80% by weight.
wherein the triglyceride oil has a Solid Fat Index of less than 10 at 50°F (10°C); the triglyceride oil has an AOM
minimum value of 100 hours; and the cis monounsaturated fatty acid content of the triglyceride oil is from 65% to 80% by weight.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39618589A | 1989-08-21 | 1989-08-21 | |
| US07/396,185 | 1989-08-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2023486A1 true CA2023486A1 (en) | 1991-02-22 |
Family
ID=23566207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2023486 Abandoned CA2023486A1 (en) | 1989-08-21 | 1990-08-17 | Liquid triglyceride oil |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2023486A1 (en) |
-
1990
- 1990-08-17 CA CA 2023486 patent/CA2023486A1/en not_active Abandoned
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |