CA1049551A - Process for purifying lecithin - Google Patents

Process for purifying lecithin

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Publication number
CA1049551A
CA1049551A CA222,599A CA222599A CA1049551A CA 1049551 A CA1049551 A CA 1049551A CA 222599 A CA222599 A CA 222599A CA 1049551 A CA1049551 A CA 1049551A
Authority
CA
Canada
Prior art keywords
phosphatides
volume
liquid
hydrophobic liquid
phosphatide
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.)
Expired
Application number
CA222,599A
Other languages
French (fr)
Other versions
CA222599S (en
Inventor
Fritz G. Sietz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Original Assignee
Unilever PLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever PLC filed Critical Unilever PLC
Application granted granted Critical
Publication of CA1049551A publication Critical patent/CA1049551A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • C07F9/10Phosphatides, e.g. lecithin
    • C07F9/103Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23JPROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J7/00Phosphatide compositions for foodstuffs, e.g. lecithin

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)

Abstract

TO ALL WHOM IT MAY CONCERN:
Be it known that I, FRITZ GEORG SIETZ, a citizen of the Federal Republic of Germany and Berlin (West), of Van Oldenbarneveldlaan 37, Zwijndrecht, Netherlands, has invented an improvement in PROCESS FOR PURIFYING PHOSPHATIDES

of which the following is a S P E C I F I C A T I O N
Abstract of the Disclosure Process for purifying phosphatides wherein crude phosphatides are subjected to the combined action of a hydrophobic liquid and an aqueous liquid, the two liquids are separated and the purified phosphatides product is recovered from the hydrophobic liquid. In this way a transparent phosphatide product is obtained.
In a preferred embodiment hexane is added to a non-dried crude phosphatide sludge obtained by the water desliming of a crude oil and the amount by volume of the hexane is about twice that of the sludge.

Description

l , cL 540 111495S~L

The i~lve~tion relates to a proces~, for purifying i phosphatides and the phosphatide product obtained by said ¦ process.
I Conventionally phosphatides are obtained from beans, in particular soya beans and other phosphatide-containing materials. In the processing of beans the phosphatides ; are, for nstance, obtained by pressing or solvent ; extraction of the beans and by separating the phosphatides from the resulting crude oils by a treatment with water or i 10 aqueous solutions.
.' I The aqueous sludge obtained contains phospholipids, ; a certain proportion of oil, fatty acids, carbohydrates, ¦ proteins, mineral salts, sterols, some remainders of the j bean shelIs and occasionally other materials. The sludge ¦ 15 may be dried to obtain a yellow to black mass with a wax-i like consistency. The phosphatides may be subjected to '¦ various treatments such as removal~of the oil, replace-ment of the oil by another oil~ hydroxylat~on and hydro-i - lysis, either by en~ymatic action or by acidic or alkaline hydrolysis. :~
Until now, however, it has been very difficult to I remove from the phosphatides some of the materials which i , i render them less suitable for certain applications.
~ U.S. Patent Specification 2,201,064 describes a .~j ,:-91 25 purification process in which dried phosphatides are . r dissolved in hexane. Bel~ian patent 590,731 describes a ~ purification process in which dried crude phosphatides .j . .
are treated with e.g. hexane and e.g. acetone which may contain up to 10% of water.
!
These prior art processes do not yield atransparent ~i~

~ 2 -' ~,.,.~,'"'.'~;''''''''''""''''"'""'''"' ~ ; ~

495Sl phosphatide product.
It has now been found that a purified phosphatide product is obtained when phosphatides are subjected to the combined action of a hydrophobic liquid and an a~ueous liquid. The two liquids are separated and the purified -phosphatide product is recovered from the hydrophobic liquid.
According to the process of the invention a transparent phosphatide product is obtained.
Surprisingly it has been found that the presence of an appreciable amount of a polar organic solvent, dissolved in the aqueous liquid, adversely affects the purification. It is therefore a special feature of the instant invention to carry out the process while less than 30% by weight, preferably less than 10% of the aqueous liquid consists of an organic polar solvent.
`(~ The process of the invention produces a purified phosphatide product which is transparent. Moreover, much of the disagreeable ~ff-flavour normally associated especially , . . .
with conventional hydrolysed phosphatides appears to have been removed during the purification treatment.
.
The hydrophobic liquid to be used in accordance with the present invention may be any hydrophobic liquid in which phosphatides are soluble. Examples are aliphatic, I preferably saturated hydrocarbons, preferably alkanes such .j ' as heptane, hexane and pentane~ Cyclic alkanes such as cyclohexane are also suitable. Aromatic compounds such as benzene may also be used. Hexane is -"
- - ' ' ' ~ 3-.. , . . .. ~, . . .

, cL 540 .
4~55:~L
, . . .
preferred. The aqueous liquid will normally be water which, however, may contain some proportion of another liquid or other liquids dissolved or dispersed therein.
¦ One preference as stated above ls the absence of substantial amounts of po]ar organic liquids from the i aqueous liquid. The presence of substantial amounts of polar organic liquids tends to make the subsequent `¦ ' ! separation of hydrophobic liquid and aqueous liquid more difficult. Moreover, it has been found that polar organic liquids cause the recovery of the phosphatide product from the hydrophobic liquid to be more troublesome and affect ¦ the quality of the product adversely. Smaller quantities, ; on the contrary, do not exhibit these undesirable characteristics, and may even facilitate the separation of hydrophobic liquid and aqueous liquid.
~ Another preference is the presence in the aqueous ; liquid of a minor amount of a bleaching agent. A suitable ~ ~ . , .
agent is H202. Suitable quantities are 0.5-5%, preferably 0.5-2% by weight, based on the aqueous liquid.
` 20 The t~rm "phosphatides" as used herein denotes a mixture of phopholipids and other materials (other than ;
water) çomprising non-lipid materials as is, for instance, ~ . :
i obtained in the aqueous sludge described above, possibly after one or more of the treatments also described above.
Such products are also often referred to as "lecithin". -The amount of aqueous liquid to be used in accordance with the process of the invention is preferably between 5 and 150% by volume of the phosphatides, more preferably between 50 and 100%.
The amount of hydrophobic liquid to be used in the , /
i '~ ' , .,.

.

~ cL 540 ~04~5~ ~
process of the invention is preferably between 200 and ¦ ,l 2000% by volume of the phosphatides, more preferably ! between 400 and 600%.
The process is preferably carried out while the amount (by volume) of hydrophobic liquid is about 1 to a~out 3 times, preferably about twice, as large as the amount (by volume) of phosphatides plus aqueous liquid.
- The sequence in which the two liquids are added to the phosphatides is immaterial. In a preferred embodiment the hydrophobic liquid is added to the aqueous sludge described above containing the phosphatides, optionally after some other treatment like, for instance, hydrolysis of the phospholipids. This procedure has the advantage that the need for an intermediate drying step is obviated.
The manner in which the two liquids are separated is not essential. Centrifuging is preferred.
Recovery of the purified phosphatide product from the hydrophobic liquid is preferably by evaporation.
The temperature and pressure at which the process is carried out can vary within wide limits. Atmospheric -pressure at ambient temperature is preferred.
The purified phosphatide product obtained is trans-`~ parent and superior to the untreated one with respect to odour, taste and oil-solubility. The product can especially usefully be applied in food preparations like margarine. Still another advantage of the purified phosphatide product according to the invention is its good oil solubility as compared with conventional products.
The advantages of the process according to the invention are especially pronounced when the process is ' , ,~ ' ' ' ' '' ' .. . .

, ~ .

cL 540 .
~L~4~55~
applied to phosphatides which have been hydrolysed by pancreatin.
! The invention is illustrated by the following - ~ examples.
EXA~PLE I
. _ 100kg crude soybean phosphatide sludge containing 33% of water were homogenised with 200 1 hexane and centrifuged. The transparent hexane phase emerging from the centrifuge was evaporated in two stages, in the first stage in a vertical evaporator, in the second stage in ~
a thin film evaporator. As compared with the phosphatides -, ~ ,: .
recovered in the conventional way, i.e. by drying of the sludge, the phosphatides obtained showed the following properties.

conventionalprocess of process the invention ~-Acetone-insoluble 6 6 matter (1) % 3 3 Moisture (2) % 0.5 -~ 0.05 Colour/Gardner (3) 10 10 ;
Colour / Iodine (4) 20 18 Colour/Lovibond (5) 35 g + 3.6 r + 35 + 3.2 . .
Sugar (calc. on ~ ~ F ~ r :
; 25 saccharose) (6) ~ ' ' J 1 .

Transparency (7) % 12.8 84.5 Acid Value (8) 23 23 Phosphorus (9) % 1.93 2.0 . Iron (10) ppm 152 73 Composition with settles does not settle (1) Acetone-insoluble matter determined according to the Official and Tentative Methods of the American Oil .. . . .

~' .

cL 540 , . , " , ' Chemists' Society.
i , .
(2) Modified Karl Fischer Method according to the Official and Tentative Methods of the American Oi' Chemists' Society.
(3) Official and Tentative Methods of the A.O.C.S.
(4) Methods of the Deutsche Gesellschaft fUr Fett-wissenschaft, Munster/Westf.
' (5) Methods of the A.O.C.S.
' (6) ditto (7) Transparency was determined as follows:
The material is heated to 50C in a waterbath.
It is then dissolved with stirring in equal parts by weight of xylol.
' Turbidity of the solution is measured in a turbidity ~- 15 measuring unit sold by B. Lange GmbH, Berlin, Germany.
The transparency of the solution is Tv = 100 - t, wherein t is the measured turbidity.
The extinction of the solution is Ev ~ logLv~
' The transparency of the material is then calculated from the formula v . 2 = log (8~ Methods of the A.O.C.S.
' (9) ditto '' (10) Methods of the Deutsche Gesellschaft fur Fett- ' ' ' 25 wissenschaft, Munster/Westf. ' EXAMPLE II ;
100 kg of crude soybean phosphatide sludge '~ containing 55% of water were''t'reated as described in Example I. The loss of sludge, calculated on the dry matter, amounted to abt. 9.5% Analytical results:

, ~ , : ' , ~ 7 cL 5ll0 1~4~SS:l conventional process of the .~ processinvention Acetone-insoluble % ~ 67 67 ~ matter '! 1' 5 Moisture % o.6S 0.05 Colour/Iodine 24 22 , Sugar % 3.2 1.7 Transparency % 10 88 ! I Acid Value 18 18 I , 10 Phosphorus % 1.962.04 Iron ppm 280 135 20% oil settlesdoes not settle -~, j EXAMPLE III
i 15 10 kg of crude soybean phosphatides were homogenised -with 10 l water. The sludge was then homogenised with401 -¦ cyclohexane and the mixture was centrifuged. The white ; ., . .:
¦ solvent phase was evaporated. The phosphatides thus ~ ~
.
¦ obtained were transparent. Analysis showed that the sugar content decreased to abt. 40~ and the iron content ¦ to abt. 55% of the starting value. The P-content had risen by 0.04%. Colour, acetone-insoluble matter and acid ¦ value had remained substantially constant. -.
~I EXAMPLE IV
_j 10 kg crude soybean phosphatides were dissolved in 40 l - -hexane. Subsequently 10 l water was stirred into the o solution. After 10 min stirring the solution was allowed to settle. After a resting period of 5 h and separation - of the phases the hexane solution was evaporated. The phosphatides thus obtained were transparent. The analyt-i ical data corresponded to those of the preceding examples.
.
`' j/ ' ' , ,, f ., ' ' , cL 540 . . .
495S~
EXAMPLR V
j ¦ 10 kg crude phosphatide sludge, which had been hydrolysed enzymatically according to USP 3,652,397, were homogenised with 20 1 hexane and centrifuged. The hydrolysed phosphatides isolated from the hexane phase : were transparent. The sugar and iron contents had been reduced to about half the star~ing values.
The P-value had increased by 0.05%. The other values (colour, acetone-insoluble matter, acid value) had remainel constant.

', --.

. ' , ~: ' :~
, :, .

' _ g _

Claims (9)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for purifying phosphatides by treatment with a solvent for the phosphatides, comprising subjecting the phosphatides to the combined action of a hydrophobic liquid in an amount of between about 200 and about 2000% by volume and an aqueous liquid containing less than 30% by weight of an organic polar solvent) in an amount of between about 5 and about 150% by volume, both calculated on the phosphatides, separating the hydrophobic liquid and the aqueous liquid and recovering the purified phosphatide product from the hydrophobic liquid.
2. Process according to claim 1, in which as the hydrophobic liquid an aliphatic saturated hydrocarbon is used.
3. Process according to claim 2, in which as the hydrophobic liquid hexane is used.
4. Process according to claim 1, in which the amount of the hydrophobic liquid is between about 400 and about 600% by volume and the amount of the aqueous liquid is between about 50 and about 100% by volume, both calculated on the volume of the phosphatide.
5. Process according to claim 1, in which the volume of the hydrophobic liquid is between about 1 and about 3 times the volume of the phosphatides plus the aqueous liquid.
6. A process for purifying phosphatide wherein the phosphatides are treated with a solvent, comprising admixing a crude phosphatide sludge obtained by the desliming of a crude oil with water and without drying the sludge with a hydrophobic liquid in an amount of about 1 to about 3 times the volume of the sludge, thoroughly mixing the hydrophobic liquid with the sludge, separating the mixture obtained into an aqueous phase and a hydrophobic phase and recovering the purified phosphatide product from the hydrophobic phase.
7. Process according to claim 6, in which the volume of the hydrophobic liquid is about twice the volume of the crude phosphatide sludge.
8. Process according to claim 6, in which the hydro-phobic phase and the aqueous phase are separated by centri-fugation.
9. Process according to claim 6, in which the purified phosphatide product is recovered from the hydrophobic liquid by evaporation of said liquid.
CA222,599A 1974-03-22 1975-03-18 Process for purifying lecithin Expired CA1049551A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB12927/74A GB1504125A (en) 1974-03-22 1974-03-22 Process for purifying phosphatides

Publications (1)

Publication Number Publication Date
CA1049551A true CA1049551A (en) 1979-02-27

Family

ID=10013697

Family Applications (1)

Application Number Title Priority Date Filing Date
CA222,599A Expired CA1049551A (en) 1974-03-22 1975-03-18 Process for purifying lecithin

Country Status (14)

Country Link
JP (1) JPS5628132B2 (en)
AT (1) AT345462B (en)
BE (1) BE827026A (en)
CA (1) CA1049551A (en)
CH (1) CH614606A5 (en)
DE (1) DE2512639A1 (en)
DK (1) DK122175A (en)
FR (1) FR2264815B1 (en)
GB (1) GB1504125A (en)
IE (1) IE41884B1 (en)
IT (1) IT1030399B (en)
LU (1) LU72108A1 (en)
NL (1) NL7503304A (en)
SE (1) SE415565B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3218027A1 (en) * 1982-05-13 1983-11-17 A. Nattermann & Cie GmbH, 5000 Köln PHOSPHOLIPID SOLUTIONS
GB8307594D0 (en) * 1983-03-18 1983-04-27 Unilever Plc Triglyceride oils
JPS63265914A (en) * 1987-04-23 1988-11-02 Sanyo Chem Ind Ltd Production of epoxy resin
IT1319679B1 (en) 2000-12-05 2003-10-23 Chemi Spa PHOSPHATIDYLSERINE PURIFICATION PROCESS.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB933814A (en) * 1959-05-12 1963-08-14 Unilever Ltd Improvements in or relating to the purification of phosphatides
AT315359B (en) * 1972-07-31 1974-05-27 Etapharm Chem Pharm Lab Ges M Process for the production of highly purified phosphatides from animal organs

Also Published As

Publication number Publication date
LU72108A1 (en) 1976-07-01
AT345462B (en) 1978-09-25
FR2264815B1 (en) 1978-02-03
NL7503304A (en) 1975-09-24
JPS5628132B2 (en) 1981-06-30
IT1030399B (en) 1979-03-30
DK122175A (en) 1975-09-23
SE7503140L (en) 1975-09-23
BE827026A (en) 1975-09-22
ATA215075A (en) 1978-01-15
GB1504125A (en) 1978-03-15
JPS50130797A (en) 1975-10-16
IE41884B1 (en) 1980-04-23
IE41884L (en) 1975-10-22
CH614606A5 (en) 1979-12-14
DE2512639A1 (en) 1975-10-16
SE415565B (en) 1980-10-13
FR2264815A1 (en) 1975-10-17

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