CA2023800A1 - Process for the removal of cholesterol and/or cholesterol esters from foodstuffs - Google Patents
Process for the removal of cholesterol and/or cholesterol esters from foodstuffsInfo
- Publication number
- CA2023800A1 CA2023800A1 CA002023800A CA2023800A CA2023800A1 CA 2023800 A1 CA2023800 A1 CA 2023800A1 CA 002023800 A CA002023800 A CA 002023800A CA 2023800 A CA2023800 A CA 2023800A CA 2023800 A1 CA2023800 A1 CA 2023800A1
- Authority
- CA
- Canada
- Prior art keywords
- cholesterol
- carbon dioxide
- process according
- extraction
- components
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C15/00—Butter; Butter preparations; Making thereof
- A23C15/12—Butter preparations
- A23C15/14—Butter powder; Butter oil, i.e. melted butter, e.g. ghee ; Anhydrous butter
- A23C15/145—Removal of steroids, e.g. cholesterol or free acids; Fractionation of anhydrous milkfat by extraction with solvents other than solvent crystallisation or with supercritical gases or by distillation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/23—Removal of unwanted matter, e.g. deodorisation or detoxification by extraction with solvents
Abstract
Abstract Process for the removal of cholesterol and/or cholesterol esters from foodstuffs The present invention provides a process for the removal of cholesterol and/or cholesterol esters from foodstuffs by extraction with compressed carbon dioxide, wherein a) the cholesterol-containing extraction material is treated with compressed carbon dioxide at a pressure above 100 bar and at a temperature of from 10 to 90°C., b) from the carbon dioxide stream loaded with cholesterol and/or cholesterol esters, as well as with further lipophilic components, the cholesterol components are selectively removed by adsorption on a solid adsorp-tion agent or by adduct formation and c) at least a part of the carbon dioxide current substant-ially free from cholesterol components is again passed over the treated extraction material and/or used for the extraction of untreated, cholesterol-containing extraction material.
Description
%o2380 ~ he present invention is concerned with a multi-step process for tbe removal of cholesterol and cholest-erol esters from foodstu~fs by extraction ~ith compressed carbon dioxide.
C~Olesterol and cholesterol esters are lipophilic substances ~Jhich occur in numerous important foodstuffs of animal origin, for example egg ~olk, meat, animal fats and the like.
As is kno~n, increased cholesterol values in the -blood serum of humans represents an increased risk factor for arteriosclerosis and of coronary heart disease.
B~ means of a reduction of the cholesterol intake from foodstuffs, it is, in pathological cases, often possible again to achieve normal cholesterol values in the blood serum. For this reason, endeavours are made in the foodstuff industry to schieve a distinct reduction of the content of cholesterol and cholesterol esters in fat-rich foodstuffs of animal origin.
An important problem is thereb~ substantially to retain the sensor~ and nutritional-physiological prop-erties o~ the foodstuffs after removal of the cholesterol components.
Admittedly~ a number of processes is already known for the isolation of cholesterol and cholesterol esters but these methods are not suitable for the reduction of the cholesterol content of foodstuffs since they bring about chemical changes of important components of the starting material, for example of proteins, tri~l~cerides and the like.
20238~o A relativel~ ~entle process for the removal of cholesterol and cholesterol esters from foodstuffs is the extraction with supercritical carbon dioxide (c~.
V~ krul{onis, ~upercritical F1Uid Processin~, International Symposium on Supercritical Fluids, Nice, 1988, and Ao Budde and D. I~norr, Xeduction of ChOlesterol in Egg Po~der and WhOle E~gs b~ E~traction with Supercritical Carbon DiOxide, Fifth International Congress on Engineerin~ and Food, Colo~ne~ 1989)~
~ is process is admittedl~ charzcterised by the ph~sio-logical safet~ of t~e carbon dioxide used as e~traction agent but, according to the known processes, cholesterol and cholesterol esters cannot be separated sufficiently selectivel~ ~rom foodstu~fs because triglycerides and other lipophilic components are also removed from the extraction material bg treatment ~Jith supercritical carbon dioxide. An improvement of the selectivity in favour of the cholesterol components in the case of the extraction is admittedly in principle possible by increasing the temperature to above 80C. but this has a negative effect on the quality o~ the product obtained, Accordin$ to an article by Rizvi and Benkrid (A Process for ChOlesterol Reduction and Fractionation of Animal Fats using Supercritical ~luids~ ~ifth I~ternational Con~ress on ~ngineerin~ a~d Food, Cologne~ 1989), it is su~gested to fractionate animal fats and thereb~ to co-extract c~olesterol on a solid adsorption agent which is not described i~ detail. However, the obàect aimed for of 202380~
preventin~ a chan~e of the sensory and nutritiona~-physiological properties of foodstuf~s by the loss of impor~ant lipophilic components which are different from cholesterol is thereb~ not achieved.
Therefore, it is an object of the present inve~tion to provide a process for -the removal of cholesterol and/or c~olesterol esters from foodstuffs b~ extraction with compressed carbo~ dioxide which does not suffer from the disadvantages of known processes but rather makes possible a substantially selective separation of the cholesterol components under ge~tle conditions and, at the same time, reduces to a minimum the losses of further import~t lipophilic components.
~ hus, accordin~ to the present invention, there is provided a process for the removal of cholesterol andjor cholesterol esters-from foodstuffs b~ extraction with compressed carbon dioxide, wheremn a) the cholesterol-containing extraction material is traated with compressed carbon dioxide at a pressure above 100 bar and a temperature of from 10 to 90C., b) the cholesterol components are selectively removed from the carbon dioxide gas stream loaded with cholesterol snd/or cholesterol esters, as well as ~ith further lipophilic components, by adsorption on a solid adsorption agent ~ by adduct formation and c) at least a part of the carbon dioxide current pre-ponderantly freed from cholesterol compone~ts is again passed over the treated extraction material ;: ' and/or e~ployed ~or the e~traction of untreated, c~olesterol-containin~ extraction material.
Surprisin~ly, we have Pound tha~, in this wa~, fat-containin~ foodstuffs with a low total chol~sterol content and ~ood sensory ~roperties are obtained.
The process accordin~ to the present invention consists, in all, of three steps.
In the ~irst step, the cholesterol-containin~
extraction material is ~reated wit~ compressed carbon dioxide. As starting material, there can be used all fat-containing foodstuf~s, such as for example egg yol~
powder, liquid egg yolk, butter fat, ~eat and the like.
Depending upon the startin~ ~aterial, tbe extraction conditions can be varies ~ithin wide limits but, for economic reasons, it is recommended preferabl~ to carr~
out the extraction above a pressure of 100 bar and at a temperature of from 10 to 90C. ~specially preferabl~, the extraction is carried out at a pressure o~ ~rom 200 to ~00 bar and at a temperature of from 30 to 60C.
because, u~der these conditions, there is no ther~al stressing of the startin~ material and the cholesterol components readil~ dissolve in the compressed carbon dioxide.-Durin~ the extraction procedure, a loadin~ of thecompressed carbon dioxide takes place with cholesterol ~, components and further lipophilic substances, for example triglycerides, phospholipids, colouring materials and the like. In thesecond step, tbe :;:
,:~
~ ' ~
202380o cholesterol components are ~eparated o~f 3S selectivel~ as possible ~rom this loaded current o~ carbon dioxide, i.e.
tile otner 'ipophilic components should remain as far as possible dissolved in the carbon dioxide. ~his selective s~parating off of t~e cholesterol components is possible in several ~lays. n the one hand, these substances can be adsorbed on an appropr~te solid adsorption agent, in which case there can be used all adsorption agents usuallg employed, ~or example aluminium oxide, silica ~el, Florosil, ma~nesium silicate and the like, or combinations thereof. n the other hand, the current of carbon dioxide can be passed through or over a packin~ of metal salts, preferablg with di- or polgvalent cations which form insoluble adducts ~Jith the cholesterol or cholesterol esters present in the carbon dioxide, examples of such salts includin~ zinc chloride, magnesium sulphate, man~anese sulphate and the like.
'rhe amount of adsorption agent or adduct former used depends, in particular, upon the total cholesterol content of the'lextraction material used and, as a rule, amounts to 1 to 100 g. per g. of cholesterol components to be removed~
A special advanta~e o~ the process according to the present invention is the fact that the separating off of the cholesterol components can take place under the same pressure and temperature conditions as the extraction so that it is not necessar~ to have to put up with an~ large losses o~ energy.
- ' 20238oo ~7--For the third step of the process according to the presen~ inven~ion, it i3 important tllat, after separatin~
off of the cholesterol co~ponents, still dissolved, non-cnolesterol-lil~e components in the carbon dioxide are not separated off. n the co~trary, the current of carbon dioxide is at least partl~ either a~ain passed over the treated extraction material or used for the extraction o~ s~ill untreated eætraction material. In botb process variants, in the case of renewed extraction, only small amounts of non-cholesterol-like lipophilic components dissolve in the current of carbon dioxide because tbe carbon dioxide is already laden ~Jith these materials.
In order to leep as small as possible ~e extraction of lipophilic materials u~ich do not consiæt of cholesterol components in the carryin~ out of the process accordin~
to the invention, the amounts of ~aseous carbon dioxide or the extraction conditions are preferably so chosen in tbe first step that a loading of the carbon dioxide can there already take place ~lhich is as substantial as possible, i.e. after tbe first eætraction, the carbon dioxide should be saturated as completely as possible witb lipophilic components.
After seLective separatin~ o~f of the cbolesterol components bg adsorption or adduct formation, the current of carbon dioxide, which is substantially free of cholesterol but saturated witb further lipophilic components, can again be passed over the extraction material in the case of the following extrsction `, . - .
202380~
procedures in o der to re~lov~ cholesterol components from foodstuffs with very hi~h selectivity.
~ he specific carbon dioxide consumption, i.e. the amount which is circulated~ depends essentiall~ upon the nature and amount of the extraction material and, as a rule, amounts to 60 to 300 ~. of carbon dioxide per k~.
of extraction material, l:~e have fou~d that for both of the above-mentioned --process variants, which can also be carried out in combination with one another, the losses of lipophilic components which do not consist of cholesterol components is less than 1~,'.
ThUs~ with the help o~ the process according to the present invention, it is possible to produce low-cholesterol foodstu~fs with good sensorg properties, the total cholesterol content of which is reduced by about 60 to 90~.
The following Examples are ~given for the purpose of illustratin~ the present invention:
Example 1.
Removal of cholesterol and cholesterol esters ~rom e~
k powder.
C~Olesterol and cholesterol esters are lipophilic substances ~Jhich occur in numerous important foodstuffs of animal origin, for example egg ~olk, meat, animal fats and the like.
As is kno~n, increased cholesterol values in the -blood serum of humans represents an increased risk factor for arteriosclerosis and of coronary heart disease.
B~ means of a reduction of the cholesterol intake from foodstuffs, it is, in pathological cases, often possible again to achieve normal cholesterol values in the blood serum. For this reason, endeavours are made in the foodstuff industry to schieve a distinct reduction of the content of cholesterol and cholesterol esters in fat-rich foodstuffs of animal origin.
An important problem is thereb~ substantially to retain the sensor~ and nutritional-physiological prop-erties o~ the foodstuffs after removal of the cholesterol components.
Admittedly~ a number of processes is already known for the isolation of cholesterol and cholesterol esters but these methods are not suitable for the reduction of the cholesterol content of foodstuffs since they bring about chemical changes of important components of the starting material, for example of proteins, tri~l~cerides and the like.
20238~o A relativel~ ~entle process for the removal of cholesterol and cholesterol esters from foodstuffs is the extraction with supercritical carbon dioxide (c~.
V~ krul{onis, ~upercritical F1Uid Processin~, International Symposium on Supercritical Fluids, Nice, 1988, and Ao Budde and D. I~norr, Xeduction of ChOlesterol in Egg Po~der and WhOle E~gs b~ E~traction with Supercritical Carbon DiOxide, Fifth International Congress on Engineerin~ and Food, Colo~ne~ 1989)~
~ is process is admittedl~ charzcterised by the ph~sio-logical safet~ of t~e carbon dioxide used as e~traction agent but, according to the known processes, cholesterol and cholesterol esters cannot be separated sufficiently selectivel~ ~rom foodstu~fs because triglycerides and other lipophilic components are also removed from the extraction material bg treatment ~Jith supercritical carbon dioxide. An improvement of the selectivity in favour of the cholesterol components in the case of the extraction is admittedly in principle possible by increasing the temperature to above 80C. but this has a negative effect on the quality o~ the product obtained, Accordin$ to an article by Rizvi and Benkrid (A Process for ChOlesterol Reduction and Fractionation of Animal Fats using Supercritical ~luids~ ~ifth I~ternational Con~ress on ~ngineerin~ a~d Food, Cologne~ 1989), it is su~gested to fractionate animal fats and thereb~ to co-extract c~olesterol on a solid adsorption agent which is not described i~ detail. However, the obàect aimed for of 202380~
preventin~ a chan~e of the sensory and nutritiona~-physiological properties of foodstuf~s by the loss of impor~ant lipophilic components which are different from cholesterol is thereb~ not achieved.
Therefore, it is an object of the present inve~tion to provide a process for -the removal of cholesterol and/or c~olesterol esters from foodstuffs b~ extraction with compressed carbo~ dioxide which does not suffer from the disadvantages of known processes but rather makes possible a substantially selective separation of the cholesterol components under ge~tle conditions and, at the same time, reduces to a minimum the losses of further import~t lipophilic components.
~ hus, accordin~ to the present invention, there is provided a process for the removal of cholesterol andjor cholesterol esters-from foodstuffs b~ extraction with compressed carbon dioxide, wheremn a) the cholesterol-containing extraction material is traated with compressed carbon dioxide at a pressure above 100 bar and a temperature of from 10 to 90C., b) the cholesterol components are selectively removed from the carbon dioxide gas stream loaded with cholesterol snd/or cholesterol esters, as well as ~ith further lipophilic components, by adsorption on a solid adsorption agent ~ by adduct formation and c) at least a part of the carbon dioxide current pre-ponderantly freed from cholesterol compone~ts is again passed over the treated extraction material ;: ' and/or e~ployed ~or the e~traction of untreated, c~olesterol-containin~ extraction material.
Surprisin~ly, we have Pound tha~, in this wa~, fat-containin~ foodstuffs with a low total chol~sterol content and ~ood sensory ~roperties are obtained.
The process accordin~ to the present invention consists, in all, of three steps.
In the ~irst step, the cholesterol-containin~
extraction material is ~reated wit~ compressed carbon dioxide. As starting material, there can be used all fat-containing foodstuf~s, such as for example egg yol~
powder, liquid egg yolk, butter fat, ~eat and the like.
Depending upon the startin~ ~aterial, tbe extraction conditions can be varies ~ithin wide limits but, for economic reasons, it is recommended preferabl~ to carr~
out the extraction above a pressure of 100 bar and at a temperature of from 10 to 90C. ~specially preferabl~, the extraction is carried out at a pressure o~ ~rom 200 to ~00 bar and at a temperature of from 30 to 60C.
because, u~der these conditions, there is no ther~al stressing of the startin~ material and the cholesterol components readil~ dissolve in the compressed carbon dioxide.-Durin~ the extraction procedure, a loadin~ of thecompressed carbon dioxide takes place with cholesterol ~, components and further lipophilic substances, for example triglycerides, phospholipids, colouring materials and the like. In thesecond step, tbe :;:
,:~
~ ' ~
202380o cholesterol components are ~eparated o~f 3S selectivel~ as possible ~rom this loaded current o~ carbon dioxide, i.e.
tile otner 'ipophilic components should remain as far as possible dissolved in the carbon dioxide. ~his selective s~parating off of t~e cholesterol components is possible in several ~lays. n the one hand, these substances can be adsorbed on an appropr~te solid adsorption agent, in which case there can be used all adsorption agents usuallg employed, ~or example aluminium oxide, silica ~el, Florosil, ma~nesium silicate and the like, or combinations thereof. n the other hand, the current of carbon dioxide can be passed through or over a packin~ of metal salts, preferablg with di- or polgvalent cations which form insoluble adducts ~Jith the cholesterol or cholesterol esters present in the carbon dioxide, examples of such salts includin~ zinc chloride, magnesium sulphate, man~anese sulphate and the like.
'rhe amount of adsorption agent or adduct former used depends, in particular, upon the total cholesterol content of the'lextraction material used and, as a rule, amounts to 1 to 100 g. per g. of cholesterol components to be removed~
A special advanta~e o~ the process according to the present invention is the fact that the separating off of the cholesterol components can take place under the same pressure and temperature conditions as the extraction so that it is not necessar~ to have to put up with an~ large losses o~ energy.
- ' 20238oo ~7--For the third step of the process according to the presen~ inven~ion, it i3 important tllat, after separatin~
off of the cholesterol co~ponents, still dissolved, non-cnolesterol-lil~e components in the carbon dioxide are not separated off. n the co~trary, the current of carbon dioxide is at least partl~ either a~ain passed over the treated extraction material or used for the extraction o~ s~ill untreated eætraction material. In botb process variants, in the case of renewed extraction, only small amounts of non-cholesterol-like lipophilic components dissolve in the current of carbon dioxide because tbe carbon dioxide is already laden ~Jith these materials.
In order to leep as small as possible ~e extraction of lipophilic materials u~ich do not consiæt of cholesterol components in the carryin~ out of the process accordin~
to the invention, the amounts of ~aseous carbon dioxide or the extraction conditions are preferably so chosen in tbe first step that a loading of the carbon dioxide can there already take place ~lhich is as substantial as possible, i.e. after tbe first eætraction, the carbon dioxide should be saturated as completely as possible witb lipophilic components.
After seLective separatin~ o~f of the cbolesterol components bg adsorption or adduct formation, the current of carbon dioxide, which is substantially free of cholesterol but saturated witb further lipophilic components, can again be passed over the extraction material in the case of the following extrsction `, . - .
202380~
procedures in o der to re~lov~ cholesterol components from foodstuffs with very hi~h selectivity.
~ he specific carbon dioxide consumption, i.e. the amount which is circulated~ depends essentiall~ upon the nature and amount of the extraction material and, as a rule, amounts to 60 to 300 ~. of carbon dioxide per k~.
of extraction material, l:~e have fou~d that for both of the above-mentioned --process variants, which can also be carried out in combination with one another, the losses of lipophilic components which do not consist of cholesterol components is less than 1~,'.
ThUs~ with the help o~ the process according to the present invention, it is possible to produce low-cholesterol foodstu~fs with good sensorg properties, the total cholesterol content of which is reduced by about 60 to 90~.
The following Examples are ~given for the purpose of illustratin~ the present invention:
Example 1.
Removal of cholesterol and cholesterol esters ~rom e~
k powder.
3 kg, of egG yolk powder ~Ihich a total cholesterol content of 2.4c~ were extracted with carbon dioxide at 280 bar pressure and at 50C,, the carbon dioxide bein~
passed in a cgcle.
Apter the extraction, the current of carbon dioxide gas loaded with cholesterol and cholesterol esters, as ` ' , ' .
well as further lipophilic components, is passed under the -same pressure .-lnd temperature conditions ~hrou~h an adsorber ~ositioned after the extr3ction container, t~is adsorber bein~ provided wi~ 1 kg, alu~inium oxide, Subsequentl~, the current o~ carbon dioxide ~as obtained, which is low in cholesterol and substantially onl~ contains lipophilic components ~hict~ do not consist o~ cholesterol components, is a~ain passed into ~he extraction container with the pre-~r~ated extraction material and recycled, ~ he e~traction circulation is main~ained for 3 hours and the specific extraction agent requirement amounts to 240 k~, of carbon dio~ide/kg. of egg golk powder, 85~,~ of ~e total amoun~ of cholesterol and cholesterol esters are re~oved from the e~g yolk powder, whereas the losses of lipophilic components which do not consist of cholesterol com~onents is about 8~.', Example 2, Removal o~ cholesterol and cholesterol esters from butter fat, :
2 k~, of butter fat with a total c~olesterol content of 0.4c,' were extracted with carbon dioxide at 280 bar pressure and at 60C., the carbon dioxide bein~ passed in a c~cleO
After the extract on, the carbon dioxide gas current was passed throu~h a followin~ adsorber which T.Jas provided with 0.~ I~g. zinc chloride. .~ter separating off the cholesterol components in the adsorber under the same pressure ard temperaturs conditiors as in ~e case of :
2~23800 the extraction, '~e carbon dioxide ~as current was recycled over already extracted material.
;~he e-~traction circulation was maintained for ~ hours and the specific extraction agent requirement was 120 k~.
of carbon dioxide per ~ of butter fat.
75c,, of t~e total amount of choles~arol and cholesterol esters was removed from the butter fat. '~he loss of lipophilic components which did not consists of cholesterol components was about 8%.
passed in a cgcle.
Apter the extraction, the current of carbon dioxide gas loaded with cholesterol and cholesterol esters, as ` ' , ' .
well as further lipophilic components, is passed under the -same pressure .-lnd temperature conditions ~hrou~h an adsorber ~ositioned after the extr3ction container, t~is adsorber bein~ provided wi~ 1 kg, alu~inium oxide, Subsequentl~, the current o~ carbon dioxide ~as obtained, which is low in cholesterol and substantially onl~ contains lipophilic components ~hict~ do not consist o~ cholesterol components, is a~ain passed into ~he extraction container with the pre-~r~ated extraction material and recycled, ~ he e~traction circulation is main~ained for 3 hours and the specific extraction agent requirement amounts to 240 k~, of carbon dio~ide/kg. of egg golk powder, 85~,~ of ~e total amoun~ of cholesterol and cholesterol esters are re~oved from the e~g yolk powder, whereas the losses of lipophilic components which do not consist of cholesterol com~onents is about 8~.', Example 2, Removal o~ cholesterol and cholesterol esters from butter fat, :
2 k~, of butter fat with a total c~olesterol content of 0.4c,' were extracted with carbon dioxide at 280 bar pressure and at 60C., the carbon dioxide bein~ passed in a c~cleO
After the extract on, the carbon dioxide gas current was passed throu~h a followin~ adsorber which T.Jas provided with 0.~ I~g. zinc chloride. .~ter separating off the cholesterol components in the adsorber under the same pressure ard temperaturs conditiors as in ~e case of :
2~23800 the extraction, '~e carbon dioxide ~as current was recycled over already extracted material.
;~he e-~traction circulation was maintained for ~ hours and the specific extraction agent requirement was 120 k~.
of carbon dioxide per ~ of butter fat.
75c,, of t~e total amount of choles~arol and cholesterol esters was removed from the butter fat. '~he loss of lipophilic components which did not consists of cholesterol components was about 8%.
Claims (18)
1. A process for the removal of at least one of cholesterol and cholesterol esters from foodstuffs by extraction with compressed carbon dioxide, wherein:
a) a cholesterol-containing extraction material is treated with compressed carbon dioxide at a pressure above 100 bar and at a temperature of from 20 to 90°C., b) from the carbon dioxide gas stream loaded with at least one of cholesterol and cholesterol esters, and with further lipophilic components, the cholesterol components are selectively removed by adsorption on a solid adsorption agent or by adduct formation and c) at least a part of the carbon dioxide current substantially free from cholesterol components is again passed over the treated extraction material and/or used for the extraction of untreated, cholesterol-containing extraction material.
a) a cholesterol-containing extraction material is treated with compressed carbon dioxide at a pressure above 100 bar and at a temperature of from 20 to 90°C., b) from the carbon dioxide gas stream loaded with at least one of cholesterol and cholesterol esters, and with further lipophilic components, the cholesterol components are selectively removed by adsorption on a solid adsorption agent or by adduct formation and c) at least a part of the carbon dioxide current substantially free from cholesterol components is again passed over the treated extraction material and/or used for the extraction of untreated, cholesterol-containing extraction material.
2. A process according to claim 1, wherein the extraction is carried out at a pressure of from 200 to 300 bar and at a temperature of from 30 to 60°C.
3. A process according to claim 1 or 2, wherein the selective removal of cholesterol com-ponents from the carbon dioxide gas current is carried out by adsorption on a solid adsorption agent.
4. A process according to claim 3, wherein aluminium oxide is used as adsorption agent.
5. A process according to claim 1 or 2, wherein the cholesterol components are selectively removed from the carbon dioxide gas current by the formation of adducts which are insoluble in carbon dioxide.
6. A process according to claim 5, wherein an appropriate metal salt is used for the adduct formation.
7. A process according to claim 6, wherein said metal salt is zinc chloride.
8. A process according to claim 1, 2, 4, 6 or 7, wherein 1 to 100 g. of adsorption agent or adduct former are used per g. of cholesterol components to be removed.
9. A process according to claim 1, 2, 4, 6 or 7, wherein the selective removal of cholesterol components is carried out under the same pressure and temperature conditions as the extraction.
10. A process according to claim 3, wherein the selective removal of cholesterol components is carried out under the same pressure and temperature conditions as the extraction.
11. A process according to claim S, wherein the selective removal of cholesterol components is carried out under the same pressure and temperature conditions as the extraction.
12. A process according to claim 8, wherein the selective removal of cholesterol components is carried out under the same pressure and temperature conditions as the extraction.
13. A process according to claim 1, 2, 4, 5, 6, 7, 10, 11 or 12, wherein the specific carbon dioxide requirement is 60 to 300 kg. of carbon dioxide per kg. of extraction material.
14. A process according to claim 3, wherein the specific carbon dioxide requirement is 60 to 300 kg.
of carbon dioxide per kg. of extraction material.
of carbon dioxide per kg. of extraction material.
15. A process according to claim 5, wherein the specific carbon dioxide requirement is 60 to 300 kg.
of carbon dioxide per kg. of extraction material.
of carbon dioxide per kg. of extraction material.
16. A process according to claim 8, wherein the specific carbon dioxide requirement is 60 to 300 kg.
of carbon dioxide per kg. of extraction material.
of carbon dioxide per kg. of extraction material.
17. A process according to claim 9, wherein the specific carbon dioxide requirement is 60 to 300 kg.
of carbon dioxide per kg. of extraction material.
of carbon dioxide per kg. of extraction material.
18. Foodstuffs, whenever freed from cholesterol and/or cholesterol esters by the process according to claim 1, 2, 4, 6, 7, 10, 11 or 12.
#15-08/20/1990
#15-08/20/1990
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3929555.9 | 1989-09-06 | ||
| DE3929555A DE3929555A1 (en) | 1989-09-06 | 1989-09-06 | METHOD FOR REMOVING CHOLESTERIN OR CHOLESTERINE STARS FROM FOOD |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2023800A1 true CA2023800A1 (en) | 1991-03-07 |
Family
ID=6388712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002023800A Abandoned CA2023800A1 (en) | 1989-09-06 | 1990-08-22 | Process for the removal of cholesterol and/or cholesterol esters from foodstuffs |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5061505A (en) |
| EP (1) | EP0416561B1 (en) |
| JP (1) | JPH0398541A (en) |
| AT (1) | ATE110530T1 (en) |
| AU (1) | AU626714B2 (en) |
| CA (1) | CA2023800A1 (en) |
| DE (2) | DE3929555A1 (en) |
| DK (1) | DK0416561T3 (en) |
| NZ (1) | NZ235031A (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5436018A (en) * | 1986-10-21 | 1995-07-25 | Source Food Technology, Inc. | Preparation of low cholesterol oil |
| US5116628A (en) * | 1989-10-30 | 1992-05-26 | Sumitomo Seika Chemicals Co., Ltd. | Process for producing liquid egg having reduced cholesterol content |
| US5238694A (en) * | 1989-10-30 | 1993-08-24 | Sumitomo Seiko Chemicals Co., Ltd. | Liquid egg having reduced cholesterol content |
| US5514401A (en) * | 1990-03-19 | 1996-05-07 | The Regents Of The University Of California | Supercritical fluid extraction of cholesterol from liquid egg yolk |
| CA2077020A1 (en) * | 1991-09-03 | 1993-03-04 | Yoshikazu Isono | Process for producing lipoprotein-containing substance having reduced lipid content and food containing substance thus produced |
| AU665438B2 (en) * | 1992-06-10 | 1996-01-04 | Kyowa Hakko Kogyo Co. Ltd. | Process for producing a cholesterol-reduced food or feed |
| DE4306303C2 (en) * | 1993-03-01 | 1996-08-08 | Barth Raiser Hopfenextraktion | Process for extracting vegetable oils |
| DE4407939A1 (en) * | 1993-03-15 | 1994-09-22 | Sueddeutsche Kalkstickstoff | Process for producing egg-based reduced-fat and reduced-cholesterol pulverulent products |
| DE4404524C2 (en) * | 1994-02-12 | 1997-12-18 | Lefo Inst Fuer Lebensmittel Un | Cream with a significantly reduced cholesterol content and process for its production |
| MX9603627A (en) * | 1994-02-23 | 1997-05-31 | Swift Eckrich Inc | Apparatus and method for defatting meat and products derived therefrom. |
| CN1084977C (en) * | 1994-05-07 | 2002-05-15 | 株式会社Ntt都科摩 | Echo canceler and its learning method |
| DE4433274A1 (en) * | 1994-09-19 | 1996-03-28 | Sueddeutsche Kalkstickstoff | Process for the preparation of fat and cholesterol-reduced egg-based powdery products with a high content of phospholipids |
| ATE242303T1 (en) * | 1995-08-17 | 2003-06-15 | Hoffmann La Roche | CHROMATOGRAPHY PROCESS |
| DE19917929C2 (en) * | 1999-04-15 | 2002-07-11 | Luckenwalder Fleischwaren Gmbh | Process for the production of low-cholesterol fats based on pork and pork fat |
| US6413572B1 (en) | 1999-08-24 | 2002-07-02 | Michael Foods, Inc. | Enhanced precooked egg product and process for formulation of precooked egg products |
| DE10018606A1 (en) * | 2000-04-14 | 2001-10-25 | Sueddeutsche Kalkstickstoff | Production of food or animal feed, especially cereal, cocoa or egg yolk product, involves extracting and separating lipids and mixing lipophilic constituents with extracted matrix using supercritical and compressed carbon dioxide |
| US20030118714A1 (en) | 2001-12-21 | 2003-06-26 | Michael Foods Of Delaware, Inc. | Formulation and process to prepare a premium formulated fried egg |
| US7288279B2 (en) | 2001-12-21 | 2007-10-30 | Michael Foods Of Delaware, Inc. | Formulated fried egg product |
| US7241469B2 (en) | 2002-05-30 | 2007-07-10 | Michael Foods, Inc. | Formulation and process to prepare a pre-formed filing unit |
| AU2002330770A1 (en) * | 2002-08-22 | 2004-03-11 | Centro De Investigacion En Alimentacion Y Desarrollo, A.C. | Low-cholesterol shrimp and method of obtaining same |
| US20110212250A1 (en) * | 2005-02-22 | 2011-09-01 | Higuera-Ciapara Inocencio | Low-cholesterol shrimp and method of obtaining same |
| MX2008016028A (en) * | 2006-06-12 | 2009-04-22 | Conagra Foods Rdm Inc | Egg product and production method. |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3717474A (en) * | 1969-12-29 | 1973-02-20 | Gen Foods Corp | Low cholesterol egg process |
| US3958034A (en) * | 1975-02-06 | 1976-05-18 | Cornell Research Foundation, Inc. | Fractionated egg yolk product |
| JPS609770B2 (en) * | 1977-11-16 | 1985-03-13 | 旭化成株式会社 | Production method of cholesterol-free defatted egg powder |
| CH643713A5 (en) * | 1980-06-04 | 1984-06-29 | Ernst Haussener | Process for the preparation of ready-to-use foods which are fried in vegetable oil and/or fat |
| US4333959A (en) * | 1980-09-26 | 1982-06-08 | Societe D'assistance Technique Pour Produits Nestle S.A. | Decholesterization of egg-yolk |
| ATE16011T1 (en) * | 1980-12-02 | 1985-10-15 | Duphar Int Res | METHOD OF ISOLATING STEROLS IN SALES QUANTITIES FROM STEROL CONTAINING MATERIALS. |
| JPS62134042A (en) * | 1985-12-05 | 1987-06-17 | Riyoushiyoku Kenkyukai | Method for fractionating low cholesterol butter fat |
| US4692280A (en) * | 1986-12-01 | 1987-09-08 | The United States Of America As Represented By The Secretary Of Commerce | Purification of fish oils |
| DK403989A (en) * | 1988-08-19 | 1990-02-20 | Corran Norman Stuart Mclachlan | PROCEDURES FOR LIPID REMOVAL |
| AU2386588A (en) * | 1988-09-09 | 1990-04-02 | Corran Norman Stuart Mclachlan | Separation of sterols from lipids |
| JPH05504975A (en) * | 1988-09-09 | 1993-07-29 | マックラクラン，コラン，ノーマン，スチュアート | Separation of sterols from lipids |
-
1989
- 1989-09-06 DE DE3929555A patent/DE3929555A1/en not_active Withdrawn
-
1990
- 1990-01-16 US US07/465,032 patent/US5061505A/en not_active Expired - Fee Related
- 1990-08-22 CA CA002023800A patent/CA2023800A1/en not_active Abandoned
- 1990-08-23 NZ NZ235031A patent/NZ235031A/en unknown
- 1990-08-27 AU AU61371/90A patent/AU626714B2/en not_active Ceased
- 1990-09-04 DE DE59006963T patent/DE59006963D1/en not_active Expired - Fee Related
- 1990-09-04 DK DK90117015.9T patent/DK0416561T3/en active
- 1990-09-04 AT AT90117015T patent/ATE110530T1/en not_active IP Right Cessation
- 1990-09-04 EP EP90117015A patent/EP0416561B1/en not_active Expired - Lifetime
- 1990-09-06 JP JP2234657A patent/JPH0398541A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK0416561T3 (en) | 1995-01-16 |
| ATE110530T1 (en) | 1994-09-15 |
| JPH0398541A (en) | 1991-04-24 |
| EP0416561A2 (en) | 1991-03-13 |
| US5061505A (en) | 1991-10-29 |
| EP0416561A3 (en) | 1991-08-14 |
| EP0416561B1 (en) | 1994-08-31 |
| DE3929555A1 (en) | 1991-03-07 |
| DE59006963D1 (en) | 1994-10-06 |
| NZ235031A (en) | 1992-01-29 |
| AU6137190A (en) | 1991-03-14 |
| AU626714B2 (en) | 1992-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2023800A1 (en) | Process for the removal of cholesterol and/or cholesterol esters from foodstuffs | |
| US5063077A (en) | Process for the removal of cholesterol and cholesterol esters from egg yolk | |
| DE3168815D1 (en) | Highly concentrated egg white product or salted whole egg and process of preparation | |
| CA2118894A1 (en) | Process for the production of egg-based products in a powder form with a reduced fat and cholesterol content | |
| NO893284L (en) | PROCEDURE FOR REMOVAL OF FOOD STEROLS. | |
| US5616352A (en) | Process for the production of fat- and cholesterol-reduced powered products based on eggs which are characterized by a high phospholipid content | |
| EP0505797B1 (en) | Process for producing a sliceable mixture of meat and cheese | |
| AU662713B2 (en) | Process for the removal of cholesterol from egg yolk | |
| CA1103984A (en) | Process for preparing squid products | |
| CZ279513B6 (en) | Process for removing cholesterol from yolk | |
| US3211559A (en) | Process for dehydrating meat | |
| CN115777880A (en) | Method for making preserved eggs | |
| RU2060668C1 (en) | Method of brine processing | |
| US789238A (en) | Process of curing meat. | |
| KR20170001302A (en) | Seasoned Squid containing garlic and the method of the same | |
| JPS5910180B2 (en) | Method for improving the flavor of livestock meat and livestock-like foods | |
| JPS6229942A (en) | Method of deoiling from food waste containing fat and oil | |
| SU1438686A1 (en) | Method of producing meat semi-finished products | |
| AU765796B2 (en) | Blood chunks | |
| JPS5561755A (en) | Frozen geoduck | |
| JPS60224695A (en) | Preparation of yolk phospholipid | |
| JPS6352856A (en) | Pickling method for meat in 'miso' | |
| JPH01243944A (en) | Improvement of flavor and eating feel of fried snack confectionery |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |