CA1313381C - Use of a fatty oil ex helianthus annuus for the production of a product containing fatty acid monoglycerides - Google Patents
Use of a fatty oil ex helianthus annuus for the production of a product containing fatty acid monoglyceridesInfo
- Publication number
- CA1313381C CA1313381C CA000566299A CA566299A CA1313381C CA 1313381 C CA1313381 C CA 1313381C CA 000566299 A CA000566299 A CA 000566299A CA 566299 A CA566299 A CA 566299A CA 1313381 C CA1313381 C CA 1313381C
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- fatty
- glycerol
- sigco
- fatty acid
- reaction
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Edible Oils And Fats (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Fatty oil ex Helianthus annuus containing 78 to 92% by weight oleic acid and 2 to 10 by weight linoleic acid, based on total fatty acids present, is used for the production of a product containing fatty acid monoglycerides, with elimination of enrichment steps in respect of the oleic acid content, by transesterification in the presence of glycerol or by fat splitting and reaction of the split fatty acid obtained with glycerol. The fatty acid monoglycerides product thus obtained show surprising oxidation stability and excellent emulsifier properties.
Fatty oil ex Helianthus annuus containing 78 to 92% by weight oleic acid and 2 to 10 by weight linoleic acid, based on total fatty acids present, is used for the production of a product containing fatty acid monoglycerides, with elimination of enrichment steps in respect of the oleic acid content, by transesterification in the presence of glycerol or by fat splitting and reaction of the split fatty acid obtained with glycerol. The fatty acid monoglycerides product thus obtained show surprising oxidation stability and excellent emulsifier properties.
Description
~ 3 3 8 ~
PATENT
Case D 7773 THE USE OF A FATTY OIL EX HELIANTHUS ANNUUS FOR THE PRODUCTION
OF A PRODUCT CONTAINING FATTY ACID MONOGLYCERIDES
BACKGROUND OF THE INVENTION
1. Field of the Invention This invention rela~es to the use of a fatty oil ex Helianthus annuus for the production of a product containing fatty acid monoglycerides.
PATENT
Case D 7773 THE USE OF A FATTY OIL EX HELIANTHUS ANNUUS FOR THE PRODUCTION
OF A PRODUCT CONTAINING FATTY ACID MONOGLYCERIDES
BACKGROUND OF THE INVENTION
1. Field of the Invention This invention rela~es to the use of a fatty oil ex Helianthus annuus for the production of a product containing fatty acid monoglycerides.
2. Statement of Related Art It is known that monoglycerides and diglycerides can be obtained by transesterification of fatty oils with glycerol in the presence of catalysts. Glycerol monostearate and distearate (GMS) and glycerol monooleate and dioleate (GM0) are of the greatest economic significance in this regard.
GMS is produced by discontinuous or continuous glycerinolysis of glycerol tristearate or of hardened fats containing at least 55% stearic acid because the starting material is readily obtainable by hardening of fats and oils. By contrast, GM0 is nor-mally produced by esterification of oleic acid with glycerol because the glycerol trioleate required for the glycerinolysis can~
only be produced on an industrial scale by a multistage process.
The oleic acid used for the esterification with glycerol is obtained by enrichment (solvent or hydrophilization process) of the oleic acid present in split tallow fatty acid. However, fun-damental limits are imposed on these enrichment processes. In -1- ~
q~
.:^
~133~
practlce, therefore, only 65 to 70% oleic ac1ds are used for the product1on of GMO.
Fatty acid monoglycerides are used as emulsif1ers pr1mar11y in the food industry. Accordingly, they have to show a h1gh resistance to oxidation, wh1ch is reduced by contents of polyun-saturated fatty acids, particularly 11noleic ac1d.
DESCRIPTION OF THE INVENTION
Other than in the operat1ng examples, or where otherwise indicated, all numbers expressing quantities of ingredients or reaction conditions used herein are to be understood as modif1ed in all instances by the term ~about".
It has now been found that fatty oils from the seeds of cer-tain sunflower (Helianthus arnuus) species and lines known, for example, from US 4,627,192 can be used for the production of a product containing f~tty acid monoglycerides by transesterification in the presence of glycerol or by fat splitting and reaction of the split ~atty acid obtained with glycerol without any need for the enrichment processes normally applied in the prior art. These species and lines preferably include one or more of SIGCO 41A, SIGCO 41B, SIGC0 4117B, SIGCO 416R, SIGCO 853R, SIGCO 273W, and sunflower lines based on the foregoing.
The fatty oils obtained from the seeds of the above species and lines of Helianthus annuus contain from 78 to 92X by weight oleic acid and 2 to iOX by weight linoleic acid, based on the total fatty acids present, with the balance (to 100% by weight) optionally palmitic acid and stearic acid and up to 1% by weight of one or more of the following fatty acids: myristic, palmito-leic, linolenic, arachic, eicosenoic, and erucic acid.
The process of the invention carried out by the trans-esterification of the above fatty oils with glycerol is carried out as follows: A fatty oil having the above composition and pre-ferably obtained from a Helianthus annuus species or line disclosed above is reacted with glycerol at a reaction temperature 3S in the ranse of from 2,0 to300G,preferably 250 to 280C in the ~3~33~1 presence of a strongly alkal1ne catalyst, e.g. a concentrated aqueous alkal1 metal hydrox1de, pre~erably sod1um hydrox1de.
After completion of the reaction (usually in 5 to 10 minutes~, the reaction mixture is cooled, e.g.
to about 200C, neutralized with a mineral acid, e.g. hydrochlor1c ac1d, sulfuric acid, or pre~erably, phosphor~c acid, and the excess glycerol removed, e.g. by d~st111ation. The resulting pro-duct is then washed, e.g. w1th a hot saturated NaCl solution, dried, and f71tered.
The process of the invention carried out by splitt1ng the fatty oil and reacting the result1ng split fatty ac1d w1th gly-cerol is carried out as follows: The fatty oil is reacted w1th water at a temperature 1n the range of 150 to 250C, preferably 185 to 215C under a pressure of from 15 to 50 bar, preferably 20 to 35 bar. After 5 or 6 hours the glycerol/water phase ~s separated and the above procedure is preferably repeated twice to improve the yield. After the last separation of the glycerol/water phase, the resulting fatty acid mixture is distilled under reduced pressure.
The distilled fatty acid mixture is then reacted with gly-cerol in the presence of a catalyst, e.g. tin, at a temperature in the range of from lâO to25~C preferably from 185 to 215C under pressure, e.g. 35 to 60 Torr. After the reaction is completed, usually within 5 hours, the reaction mixturc is cooled and excess glycerol remo~ed, e.g. by distillation.
It has surprisingly been found that the products containing fatty acid monoglycerides based on these ~at'y oils obtained from the above processes show improved performance properties. Thus, their oxidation stability is considerably greater than that of prior art fatty acid monoglycerides. This is surprising insofar as the content of polyunsaturated fatty acids in the fatty acid monoglycerides obtained in accordanc-e wi~h the invention is as high as in those obtained from split tallow fatty acid. In addition, the fatty acid ~3~338~
monoglycer7des obtalned ln accordance wlth the lnvent10n show 1mproved emulslfler propertles compared wlth the fatty acld monoglycerldes known from the pr10r art. Flnally, 1t ls also surpr1s1ng that, where the present fatty ol~s are used, ~t 1s S poss1ble to obta7n fatty acld monoglycerldes wh7ch show ox1datlon stabll1ty, neutrallty of odor, taste and color and favorable emuls1f7er properties w1thout these fatty oils used as start1ng materials having to be subjected to any enr1chment steps before the reaction.
Since the fatty oils used as startlng materials are natural substances, the proportlons of thelr prlnc1pal components are sub-~ected to certain variat70ns. Typically, the fatty oils or rather the fatty acid monoglycerides obta~ned from them in accordance with the invention show the following ranges of var1ation ~n regard to the fatty acids:
ole1c acid:78 to 92X by weight 17noleic acid:2 to 10% by weight palmlt1c ac1d:2 to 5% by weight stear7c acid:2 to 7% by welght The glycerol monoleates prepared in accordance with the 7nvention using the above fatty o11s have monoester contents of 40 to 60% wh1ch may be 1ncreased to levels of 90% and higher by stan-dard methods, for example by molecular dist111ation.
The invent70n w711 be illustrated but not lim7ted by the follow1ng examples.
EXAMPLES
The GM0 prepared us1ng fatty oils of the above compos1t70n ln accordance w7th the invent10n was tested for 1ts oxidation stab71ity ~n a Ranc~mat*against a GM0 convent70nally produced from glycerol and fractionated oleic ac7d. A Ranc1mat (made by the Metrohm com-pany) 7s an analyt~cal apparatus widely used in the food 7ndustry for testlng the ox7dat70n stab717ty of unsaturated oils.
For the analys1s, a constant stream of a1r 7s passed through a def7ned quantity of sample at elevated temperature (100 to 120C). The volat71e compounds formed during the oxidation are *Trade Mark _~_ s~ 13~33~
determ1ned from the1r electr1tal conduct1v1ty 1n a condensat10n vessel. The per~od of t1me elaps1ng before volat11e, electr1cally conduct1ve ox~dat10n products are formed 1s called the 1nduct10n t1me.
An induction time of 4 h was measured for the GMO produced 1n accordance with the 1nYention wh11e an 1nduction time of 2 h was measured for the GMO obtained from split tallow fatty ac1d.
In addition, odor and taste were evaluated on a 10 points scale. IO points s19n1fy a product of neutral taste and odor; 1 point signifies a totally unuseable product. For use 1n the food industry, oils should have a points score of at least 6. The color was measured 1n a Lovibond t1ntometer using a 5~" cell.
The results obtained are shown in Table 1 below.
Table 1 GMO by tr~ns-esterification GMO from split in accordance tallow fatty acid with the invention Odor (undiluted at 50C) 6 points 8 points Taste (5% in MCT oil of neutral taste) 6 points 8 points Color (Lovibond) Yellow 68 65 Red 12 10 The GMO obtained in accordance with the invention affords distinct sensorial and, albeit less pronounced, color-related advantages.
Hence, the fatty acid monoglycerides product in accordance with the invention affords distinct advantages in terms of performance because the possibilities of using GMO for the production of emulsions, for example edible fat emulsions as a substitute for calves' milk (milk substitute) or margarines of high water con-tent or other fat-containing low-calorie spreads and emulsions for 1 3~3~
1ndustr~al use (for example for bread sl~clng machines), have hltherto been ser~ously restricted by inadequate ox1dat10n stab1-11ty and sensor1al 1mpa~rments.
The following comparison example demonstrates the outstanding 5 suitability of the monoglycerides of the invention obtained using fatty oils hav1ng the composit10n indicated above for the produc-t~on of emuls10ns.
0.5 part by weight of emulsifier of split tallow fatty acid and 0.5 part by weight of emulsifier according to the invention 10 were dissolved in 35 parts by weight soybean oil at 40C. 64.5 parts by weight water were then added with stirring in a slow stream. Finally, the pre-emulsion was finely homogenized twice at 120 bar in a high-pressure homogenizer.
The stability of the emulsions obtained, which were left standing in a quantity of 100 ml in a graduated cylinder, was determined after 24 h and after 8 days by visual assessment and by extraction of 25 ml layers with petroleum ether, the 25 ml layers being removed from below and extracted by shaking w1th petroleum ether. The organic phases were separated off, the petroleum ether evaporated and the residue (= fat content) weighed.
The results are shown in Table 2 below.
Table 2 Emulsions containing:
0.5% GM0 from split 0.5% GM0 according tallow fatt~ to the invention_ Af~er 24 hdistinct oil filmemulsion still uniform visible - After 8 da~s% fat contentX fat content Layer I 0.35 6.2 Layer II 2.75 7.8 Layer III 10.3 8.8 Layer IV 19.5 10.2 -As can be seen from Table 2, the glycerol monooleate accord-ing to the invention shows superior emulsif~er properties to the glycerol monooleate according to the prior art.
2 ~
The production of the glycerol monooleate by transesterlfl-cat~on set forth ln Tables 1 and 2 above us~ng a fatty o~l in accordance with the invent~on is described in detail below:
According to analysis by gas chromatograPhy. the fatty oil 5 obtained from a Helianthus annuus species covered by U.S. 4627192 ha~ the ~ollowin~ ~atty acid composition:
myristic acid0.1~ by weight palmitic acid3.1X by weight stearic acid2.0% by we~ght 10 oleic acid86.2X by weight linoleic acid7.8% by weight linolenic acid0.2X by weight arachic acid0.2X by weight eicosenoic acid 0.2'~ by weight 15 erucic acid0.2~ by weight 688 9 sunflower oil havin~ the above composition and 290 9 99.5% glycerol were heated under nitrogen to 265C in a 2-liter three-necked flask equipped with a stirrer, thermometer, frac-tionating column and external heating system. After the tem-perature of 265 had been reached, 0.05% by volume 50Z sodium hydroxide were added. The reaction was over after 5 to 10 minutes (the contents of the flask becoming clear). The reaction product was cooled, neutralized with phosphoric acid at 200C and left standing for about 10 minutes at 100C. The excess glycerol was distilled off, after which the product was washed three times with approx. 200 ml hot saturated NaCl solution at 95C. After drying at 90 to 100C in a water jet vacuum, the product was filtered with addition of 1% of a filter aid.
An oleic acid monoglyceride having the following characteric-tics was obtained:
Acid value ~.3 Saponification value 163 Iodine value 74 OH value ?39 35 Glycerol content0.6Z by weight Monoglyceride content 60% by weight
GMS is produced by discontinuous or continuous glycerinolysis of glycerol tristearate or of hardened fats containing at least 55% stearic acid because the starting material is readily obtainable by hardening of fats and oils. By contrast, GM0 is nor-mally produced by esterification of oleic acid with glycerol because the glycerol trioleate required for the glycerinolysis can~
only be produced on an industrial scale by a multistage process.
The oleic acid used for the esterification with glycerol is obtained by enrichment (solvent or hydrophilization process) of the oleic acid present in split tallow fatty acid. However, fun-damental limits are imposed on these enrichment processes. In -1- ~
q~
.:^
~133~
practlce, therefore, only 65 to 70% oleic ac1ds are used for the product1on of GMO.
Fatty acid monoglycerides are used as emulsif1ers pr1mar11y in the food industry. Accordingly, they have to show a h1gh resistance to oxidation, wh1ch is reduced by contents of polyun-saturated fatty acids, particularly 11noleic ac1d.
DESCRIPTION OF THE INVENTION
Other than in the operat1ng examples, or where otherwise indicated, all numbers expressing quantities of ingredients or reaction conditions used herein are to be understood as modif1ed in all instances by the term ~about".
It has now been found that fatty oils from the seeds of cer-tain sunflower (Helianthus arnuus) species and lines known, for example, from US 4,627,192 can be used for the production of a product containing f~tty acid monoglycerides by transesterification in the presence of glycerol or by fat splitting and reaction of the split ~atty acid obtained with glycerol without any need for the enrichment processes normally applied in the prior art. These species and lines preferably include one or more of SIGCO 41A, SIGCO 41B, SIGC0 4117B, SIGCO 416R, SIGCO 853R, SIGCO 273W, and sunflower lines based on the foregoing.
The fatty oils obtained from the seeds of the above species and lines of Helianthus annuus contain from 78 to 92X by weight oleic acid and 2 to iOX by weight linoleic acid, based on the total fatty acids present, with the balance (to 100% by weight) optionally palmitic acid and stearic acid and up to 1% by weight of one or more of the following fatty acids: myristic, palmito-leic, linolenic, arachic, eicosenoic, and erucic acid.
The process of the invention carried out by the trans-esterification of the above fatty oils with glycerol is carried out as follows: A fatty oil having the above composition and pre-ferably obtained from a Helianthus annuus species or line disclosed above is reacted with glycerol at a reaction temperature 3S in the ranse of from 2,0 to300G,preferably 250 to 280C in the ~3~33~1 presence of a strongly alkal1ne catalyst, e.g. a concentrated aqueous alkal1 metal hydrox1de, pre~erably sod1um hydrox1de.
After completion of the reaction (usually in 5 to 10 minutes~, the reaction mixture is cooled, e.g.
to about 200C, neutralized with a mineral acid, e.g. hydrochlor1c ac1d, sulfuric acid, or pre~erably, phosphor~c acid, and the excess glycerol removed, e.g. by d~st111ation. The resulting pro-duct is then washed, e.g. w1th a hot saturated NaCl solution, dried, and f71tered.
The process of the invention carried out by splitt1ng the fatty oil and reacting the result1ng split fatty ac1d w1th gly-cerol is carried out as follows: The fatty oil is reacted w1th water at a temperature 1n the range of 150 to 250C, preferably 185 to 215C under a pressure of from 15 to 50 bar, preferably 20 to 35 bar. After 5 or 6 hours the glycerol/water phase ~s separated and the above procedure is preferably repeated twice to improve the yield. After the last separation of the glycerol/water phase, the resulting fatty acid mixture is distilled under reduced pressure.
The distilled fatty acid mixture is then reacted with gly-cerol in the presence of a catalyst, e.g. tin, at a temperature in the range of from lâO to25~C preferably from 185 to 215C under pressure, e.g. 35 to 60 Torr. After the reaction is completed, usually within 5 hours, the reaction mixturc is cooled and excess glycerol remo~ed, e.g. by distillation.
It has surprisingly been found that the products containing fatty acid monoglycerides based on these ~at'y oils obtained from the above processes show improved performance properties. Thus, their oxidation stability is considerably greater than that of prior art fatty acid monoglycerides. This is surprising insofar as the content of polyunsaturated fatty acids in the fatty acid monoglycerides obtained in accordanc-e wi~h the invention is as high as in those obtained from split tallow fatty acid. In addition, the fatty acid ~3~338~
monoglycer7des obtalned ln accordance wlth the lnvent10n show 1mproved emulslfler propertles compared wlth the fatty acld monoglycerldes known from the pr10r art. Flnally, 1t ls also surpr1s1ng that, where the present fatty ol~s are used, ~t 1s S poss1ble to obta7n fatty acld monoglycerldes wh7ch show ox1datlon stabll1ty, neutrallty of odor, taste and color and favorable emuls1f7er properties w1thout these fatty oils used as start1ng materials having to be subjected to any enr1chment steps before the reaction.
Since the fatty oils used as startlng materials are natural substances, the proportlons of thelr prlnc1pal components are sub-~ected to certain variat70ns. Typically, the fatty oils or rather the fatty acid monoglycerides obta~ned from them in accordance with the invention show the following ranges of var1ation ~n regard to the fatty acids:
ole1c acid:78 to 92X by weight 17noleic acid:2 to 10% by weight palmlt1c ac1d:2 to 5% by weight stear7c acid:2 to 7% by welght The glycerol monoleates prepared in accordance with the 7nvention using the above fatty o11s have monoester contents of 40 to 60% wh1ch may be 1ncreased to levels of 90% and higher by stan-dard methods, for example by molecular dist111ation.
The invent70n w711 be illustrated but not lim7ted by the follow1ng examples.
EXAMPLES
The GM0 prepared us1ng fatty oils of the above compos1t70n ln accordance w7th the invent10n was tested for 1ts oxidation stab71ity ~n a Ranc~mat*against a GM0 convent70nally produced from glycerol and fractionated oleic ac7d. A Ranc1mat (made by the Metrohm com-pany) 7s an analyt~cal apparatus widely used in the food 7ndustry for testlng the ox7dat70n stab717ty of unsaturated oils.
For the analys1s, a constant stream of a1r 7s passed through a def7ned quantity of sample at elevated temperature (100 to 120C). The volat71e compounds formed during the oxidation are *Trade Mark _~_ s~ 13~33~
determ1ned from the1r electr1tal conduct1v1ty 1n a condensat10n vessel. The per~od of t1me elaps1ng before volat11e, electr1cally conduct1ve ox~dat10n products are formed 1s called the 1nduct10n t1me.
An induction time of 4 h was measured for the GMO produced 1n accordance with the 1nYention wh11e an 1nduction time of 2 h was measured for the GMO obtained from split tallow fatty ac1d.
In addition, odor and taste were evaluated on a 10 points scale. IO points s19n1fy a product of neutral taste and odor; 1 point signifies a totally unuseable product. For use 1n the food industry, oils should have a points score of at least 6. The color was measured 1n a Lovibond t1ntometer using a 5~" cell.
The results obtained are shown in Table 1 below.
Table 1 GMO by tr~ns-esterification GMO from split in accordance tallow fatty acid with the invention Odor (undiluted at 50C) 6 points 8 points Taste (5% in MCT oil of neutral taste) 6 points 8 points Color (Lovibond) Yellow 68 65 Red 12 10 The GMO obtained in accordance with the invention affords distinct sensorial and, albeit less pronounced, color-related advantages.
Hence, the fatty acid monoglycerides product in accordance with the invention affords distinct advantages in terms of performance because the possibilities of using GMO for the production of emulsions, for example edible fat emulsions as a substitute for calves' milk (milk substitute) or margarines of high water con-tent or other fat-containing low-calorie spreads and emulsions for 1 3~3~
1ndustr~al use (for example for bread sl~clng machines), have hltherto been ser~ously restricted by inadequate ox1dat10n stab1-11ty and sensor1al 1mpa~rments.
The following comparison example demonstrates the outstanding 5 suitability of the monoglycerides of the invention obtained using fatty oils hav1ng the composit10n indicated above for the produc-t~on of emuls10ns.
0.5 part by weight of emulsifier of split tallow fatty acid and 0.5 part by weight of emulsifier according to the invention 10 were dissolved in 35 parts by weight soybean oil at 40C. 64.5 parts by weight water were then added with stirring in a slow stream. Finally, the pre-emulsion was finely homogenized twice at 120 bar in a high-pressure homogenizer.
The stability of the emulsions obtained, which were left standing in a quantity of 100 ml in a graduated cylinder, was determined after 24 h and after 8 days by visual assessment and by extraction of 25 ml layers with petroleum ether, the 25 ml layers being removed from below and extracted by shaking w1th petroleum ether. The organic phases were separated off, the petroleum ether evaporated and the residue (= fat content) weighed.
The results are shown in Table 2 below.
Table 2 Emulsions containing:
0.5% GM0 from split 0.5% GM0 according tallow fatt~ to the invention_ Af~er 24 hdistinct oil filmemulsion still uniform visible - After 8 da~s% fat contentX fat content Layer I 0.35 6.2 Layer II 2.75 7.8 Layer III 10.3 8.8 Layer IV 19.5 10.2 -As can be seen from Table 2, the glycerol monooleate accord-ing to the invention shows superior emulsif~er properties to the glycerol monooleate according to the prior art.
2 ~
The production of the glycerol monooleate by transesterlfl-cat~on set forth ln Tables 1 and 2 above us~ng a fatty o~l in accordance with the invent~on is described in detail below:
According to analysis by gas chromatograPhy. the fatty oil 5 obtained from a Helianthus annuus species covered by U.S. 4627192 ha~ the ~ollowin~ ~atty acid composition:
myristic acid0.1~ by weight palmitic acid3.1X by weight stearic acid2.0% by we~ght 10 oleic acid86.2X by weight linoleic acid7.8% by weight linolenic acid0.2X by weight arachic acid0.2X by weight eicosenoic acid 0.2'~ by weight 15 erucic acid0.2~ by weight 688 9 sunflower oil havin~ the above composition and 290 9 99.5% glycerol were heated under nitrogen to 265C in a 2-liter three-necked flask equipped with a stirrer, thermometer, frac-tionating column and external heating system. After the tem-perature of 265 had been reached, 0.05% by volume 50Z sodium hydroxide were added. The reaction was over after 5 to 10 minutes (the contents of the flask becoming clear). The reaction product was cooled, neutralized with phosphoric acid at 200C and left standing for about 10 minutes at 100C. The excess glycerol was distilled off, after which the product was washed three times with approx. 200 ml hot saturated NaCl solution at 95C. After drying at 90 to 100C in a water jet vacuum, the product was filtered with addition of 1% of a filter aid.
An oleic acid monoglyceride having the following characteric-tics was obtained:
Acid value ~.3 Saponification value 163 Iodine value 74 OH value ?39 35 Glycerol content0.6Z by weight Monoglyceride content 60% by weight
Claims (13)
1. In a process for the preparation of a product containing glycerol monooleate by either transesterifying a fatty oil with glycerol or splitting the fatty oil to form a fatty acid mixture followed by enrichment of the fatty acid mixture to increase the oleic acid content thereof, and reaction of the enriched fatty acid mixture with glycerol, the improvement wherein the fatty oil is obtained from the seeds of Helianthus annuus and the fatty oil contains from about 78 to about 92% by weight of oleic acid, based on the total weight of fatty acids present therein, and the reaction of the fatty acid mixture is carried out without first enriching the fatty acid mixture to increase the oleic acid content thereof.
2. The process of claim 1 wherein the fatty oil is obtained from the seeds of at least one of the following lines of Helianthus annuus: SIGCO 41A, SIGCO 41B, SIGCO 4117B, SIGCO 416R, SIGCO 853R, SIGCO 273W, and sunflower lines based on the foregoing.
3. The product containing glycerol monooleate obtained from the process of claim 1 wherein the product exhibits improved oxidation stability and emulsifier properties, and good colour, odour and taste characteristics.
4. The product containing glycerol monooleate obtained from the process of claim 2 wherein the product exhibits improved oxidation stability and emulsifier properties, and good colour, odour and taste characterstics.
5. A process for the preparation of a product containing glycerol monooleate consisting essentially of the steps of:
A. transesterifying a fatty oil obtained from the seeds of Helianthus annuus and which contains from about 78 to about 92% by weight of oleic acid, based on the total weight of fatty acids present therein, with glycerol at a reaction temperature in the range of from about 230 to about 300°C in the presence of a strongly alkaline catalyst to form a reaction mixture, B. neutralizing the reaction mixture with a mineral acid, and C. removing excess glycerol from the reaction mixture.
A. transesterifying a fatty oil obtained from the seeds of Helianthus annuus and which contains from about 78 to about 92% by weight of oleic acid, based on the total weight of fatty acids present therein, with glycerol at a reaction temperature in the range of from about 230 to about 300°C in the presence of a strongly alkaline catalyst to form a reaction mixture, B. neutralizing the reaction mixture with a mineral acid, and C. removing excess glycerol from the reaction mixture.
6. The process of claim 5 wherein the glycerol monooleate from step C. is then washed, dried, and filtered.
7. The process of claim 5 wherein in step A. the reaction temperature is from about 250 to about 280°C.
8. A process for the preparation of a product containing glycerol monooleate consisting essentially of the steps of:
A. splitting a fatty oil obtained from the seeds of Helianthus annuus and which contains from about 78 to about 92% by weight of oleic acid, based on the total weight of fatty acids present therein, with water at a temperature in the range of from about 150 to about 250°C, to form a fatty acid phase and a glycerol/water phase.
B. separating the glycerol/water phase from the fatty acid phase, C. distilling the fatty acid phase, D. reacting the fatty acid phase with glycerol to form glycerol monooleate, and E. removing therefrom excess glycerol.
A. splitting a fatty oil obtained from the seeds of Helianthus annuus and which contains from about 78 to about 92% by weight of oleic acid, based on the total weight of fatty acids present therein, with water at a temperature in the range of from about 150 to about 250°C, to form a fatty acid phase and a glycerol/water phase.
B. separating the glycerol/water phase from the fatty acid phase, C. distilling the fatty acid phase, D. reacting the fatty acid phase with glycerol to form glycerol monooleate, and E. removing therefrom excess glycerol.
9. The process of claim 8 wherein the fatty oil is obtained from the seeds of at least one of the following lines of Helianthus annuus: SIGCO 41A, SIGCO 41B, SIGCO 4117B, SIGCO 416R, SIGCO 853R, SIGCO 273W, and sunflower lines based on the foregoing.
10. The process of claim 8 wherein in step A. the reaction temperature is from about 185 to about 215°C.
11. The process of claim 8 wherein in step D the reaction temperature is in the range of from about 180 to abut 250°C, and the reaction is carried out under pressure of from about 35 to about 60 Torr.
12. The process of claim 11 wherein the reaction temperature is in the range of from about 185 to 215°C.
13. The process of claim 8 wherein steps A and B are each carried out three times prior to carrying out step C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3715424.9 | 1987-05-08 | ||
| DE3715424A DE3715424C2 (en) | 1987-05-08 | 1987-05-08 | Use of a fatty oil from Helianthus annuus for the production of fatty acid monoglycerides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1313381C true CA1313381C (en) | 1993-02-02 |
Family
ID=6327129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000566299A Expired - Fee Related CA1313381C (en) | 1987-05-08 | 1988-05-09 | Use of a fatty oil ex helianthus annuus for the production of a product containing fatty acid monoglycerides |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0289968B1 (en) |
| JP (1) | JPS63287749A (en) |
| AT (1) | ATE62016T1 (en) |
| CA (1) | CA1313381C (en) |
| DE (2) | DE3715424C2 (en) |
| ES (1) | ES2021786B3 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4236340C2 (en) * | 1992-10-28 | 1994-11-10 | Daimler Benz Ag | Arrangement for the inductive transmission of energy |
| GB9416846D0 (en) * | 1994-08-19 | 1994-10-12 | Croda Int Plc | Lipid supplementation |
| FR2750159B1 (en) * | 1996-06-24 | 1998-08-07 | Inst Francais Du Petrole | METHOD AND SYSTEM FOR REAL-TIME ESTIMATION OF AT LEAST ONE PARAMETER RELATED TO THE BEHAVIOR OF A DOWNHOLE TOOL |
| FR2752850A1 (en) * | 1996-08-27 | 1998-03-06 | Inst Francais Du Petrole | COMPOSITIONS OF ADDITIVES IMPROVING THE LUBRICATING POWER OF FUELS AND FUELS CONTAINING THEM |
| WO2017085737A1 (en) * | 2015-11-19 | 2017-05-26 | Fine Research & Development Centre Pvt Ltd | A natural based monoglyceride with improved odor and flavor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789119A (en) * | 1954-02-09 | 1957-04-16 | Boake Roberts & Co Ltd | Production of fatty acid monoglycerides |
| DE1099520B (en) * | 1957-01-04 | 1961-02-16 | E F Drew & Co Inc | Process for the production of monoglycerides of fatty acids with 8 to 22 carbon atoms |
| US2976251A (en) * | 1957-04-19 | 1961-03-21 | Eastman Kodak Co | Glycerol fatty acid partial ester gels |
| US4627192B1 (en) * | 1984-11-16 | 1995-10-17 | Sigco Res Inc | Sunflower products and methods for their production |
-
1987
- 1987-05-08 DE DE3715424A patent/DE3715424C2/en not_active Expired - Fee Related
-
1988
- 1988-04-30 DE DE8888106971T patent/DE3862147D1/en not_active Revoked
- 1988-04-30 ES ES88106971T patent/ES2021786B3/en not_active Expired - Lifetime
- 1988-04-30 EP EP88106971A patent/EP0289968B1/en not_active Expired - Lifetime
- 1988-04-30 AT AT88106971T patent/ATE62016T1/en not_active IP Right Cessation
- 1988-05-09 CA CA000566299A patent/CA1313381C/en not_active Expired - Fee Related
- 1988-05-09 JP JP63113412A patent/JPS63287749A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3862147D1 (en) | 1991-05-02 |
| JPS63287749A (en) | 1988-11-24 |
| DE3715424A1 (en) | 1988-11-17 |
| EP0289968A1 (en) | 1988-11-09 |
| ATE62016T1 (en) | 1991-04-15 |
| ES2021786B3 (en) | 1991-11-16 |
| DE3715424C2 (en) | 1995-01-26 |
| EP0289968B1 (en) | 1991-03-27 |
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