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United States Patent (19) 11 Patent Number: 4,585,593 Keulemans Et Al

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United States Patent (19) 11 Patent Number: 4,585,593 Keulemans Et Al United States Patent (19) 11 Patent Number: 4,585,593 Keulemans et al. (45) Date of Patent: Apr. 29, 1986 54 INTERESTERIFICATION PROCESS AND 4,284,578 8/1981 Lathauwer et al. ............. 260/410.7 APPARATUS 4,335,156 6/1982 Kogan et al. ................ 260/410.7 X (75) Inventors: Cornelis N. M. Keulemans, FOREIGN PATENT DOCUMENTS Rozenburg; Gerard Smits, 55-012146 1/1980 Japan. Rotterdam, both of Netherlands 57-047396 3/1982 Japan. 73. Assignee: Lever Brothers Company, New York, 796808 11/1955 United Kingdom . N.Y. 767085 9/1980 U.S.S.R. (21) Appl. No.: 690,820 OTHER PUBLICATIONS 22 Filed: Jan. 11, 1985 J. Am. Oil Chemists' Soc., 44414A (1967). Journal of the American Oil Chemists Society, 55, 1978 Related U.S. Application Data (796) (Sreenivasan). 63 Continuation of Ser. No. 422,778, Sep. 24, 1982, aban Primary Examiner-Helen M. S. Sneed doned. Attorney, Agent, or Firm-James J. Farrell (30) Foreign Application Priority Data (57) ABSTRACT Oct. 6, 1981 GB) United Kingdom ................. 813013S The process is a continuous process and comprises bringing together streams comprising a triglyceride oil 51 int. Cl." ................................................ C11C3/02 and a catalyst solution of water, sodium hydroxide and 52 U.S. Cl. ............... ... 260/410.7; 422/224 glycerine respectively, homogenizing the mixture, re 58) Field of Search ...................... 260/410.7; 422/224 ducing its water content, and interesterifying. Prefera (56) References Cited bly the homogenization and drying steps take place consecutively and are combined and are performed by U.S. PATENT DOCUMENTS passage through a spray drying nozzle. The efficiency 2,309,949 2/1943 Gooding . 2,474,740 6/1949. Ittner ................................ 260/410.7 of the homogenization and drying steps allows the in 2,738,278 3/1956 Holman et al. .............. 260/410.7 X teresterifying step to take place in about 4 minutes and 3,095,431 6/1963 Giddings et al. thus permit operation of the process in a continuous ac. 3,170,798 2/1965 Burgers et al. .............. 260/410.7 X 3,271,434 9/1966 Baenitz ............................. 260/410.7 4,263,216 4/1981 Volpenhein ...................... 260/410.7 23 Claims, 8 Drawing Figures U.S. Patent Apr. 29, 1986 4,585,593 WWELS U.S. Patent Apr. 29, 1986 Sheet 2 of6 4.585,593 Fig. 2D. 28 \ \ Y o 0.07% NaOH O 0.10% NOOH 24 \ O 0.14% NaOH : 3 6- Ap(B)g5 (kg/h) U.S. Patent Apr. 29, 1986 Sheet 3 of 6 4,585,593 S. s Cd cd Cd 3 3 Nad s CN NOWOSN / U.S. Patent Apr. 29, 1986 Sheet 4 of 6 4,585,593 (NIW)HW||NOILIJVER] 001 NOV) SN / U.S. Patent Apr. 29, 1986 Sheets of 6 4,585,593 se : s st cN g s co ODOONOW/ U.S. Patent Apr. 29, 1986 Sheet 6 of 6 4,585,593 DVEH(NW)BWLINOII no3GIÐMIÐIG%0g+ NOILV)-23 IS383LN % 4,585,593 1. 2 solution; (ii) homogenising the oil and catalyst solution INTERESTERFICATION PROCESS AND by subjection to energetic shear; (iii) reducing the water APPARATUS content of the homogenised mixture so as to allow the formation of an active catalyst component as herein This is a continuation of Ser. No. 422,778, filed Sept. 5 defined; and (iv) holding the resulting mixture at a tem 24, 1982, now abandoned. perature sufficient to cause interesterification. The present invention relates to a process and an The continuous confluence of two streams followed apparatus for the interesterification of fats and oils and by homogenisation can allow a very fine and rapid to the fats and oils so treated. In the present specifica dispersion of the aqueous catalyst solution to be tion the terms "fats' and "oils' are used interchange 10 achieved in the oil. The size of the aqueous droplets ably. determines the rate of water removal as well as the Molecular rearrangement of triglycerides is a tool surface area between the catalyst and the oil and can well known in the art to adjust the physical characteris thus influence the time necessary to complete the intere tics of a fat or oil. Interesterification of the fatty acid sterification reaction. We have for example found that moieties can for example alter the melting point of a 15 aqueous droplets as small as about 10.5 m can be triglyceride composition without substantially effecting achieved on homogenisation, which on water removal its overall fatty acid composition. give catalyst particles of from about 2 to about 10 um A review article in J.A.O.C.S. 44414A(1967) entitled which bring about at least 90% interesterification "Interesterification Products and Processes' describes a within about 4 minutes. A continuous throughput of variety of process conditions and catalysts capable of 20 triglycerides is thus possible without a long residence bringing about the reaction. It refers for example to time for any part of the process. U.S. Pat. No. 3,170,798 which is an example of a batch Use of an on-line process can moreover allow very process. The oil, which if necessary has been pre-neu short contact times between the initial confluence of the tralised by heating with an aqueous alkaline solution to streams and the subsequent removal of water. Due to reduce its free fatty acid content to not more than 0.1%, 25 the variety of reactions which can occur on admixture is placed in a reaction vessel and the catalyst comprising of the catalyst solution and the oil the prompt removal a mixture of water, an alkali metal hydroxide and glyc of water to a value of less than 0.03 wt %, preferably erine is stirred into the oil. The reaction mixture is less than 0.01 wt % (as measured by the Karl-Fischer heated to a reaction temperature and the reaction is method), can be advantageous in furthering the desired allowed to proceed for between 30 minutes and 1 hour. 30 interesterification reaction. The water is necessarily The process described in U.S. Pat. No. 3,170,798 there present initially to act as a carrier for the alkali metal fore suffers inter alia from a long reaction time required hydroxide and glycerine and to aid their dispersal in the to effect interesterification. The specification moreover oil and is moreover produced by the action of the cata emphasises the need to reduce the free fatty acid con lyst. tent to less than 0.1 wt % in order to effect successful 35 interesterification. Sreenivasan (J.A.O.C.S. 55 (1978) The following are the more important reactions 796) therefore views the batch process as a two stage which are thought to occur following admixture of the reaction involving two distinct heating steps, one at a tWO Streams: low temperature of 60° C. under vacuum to effect neu tralisation, water removal and catalyst dispersion and H2O 1. the second at a higher temperature for interesterifica (a) MOH + glycerine s =&M glycerolate (insoluble in oil) tion. (b) M glycerolate -Gactive catalytic component A continuous process referred to at page 454A in the Rate of reaction (b) is increased in the presence of mono review article in JAOCS 44 comprises that described in and diglycerides. U.S. Pat. No. 2,738,278. The process there described 45 involves the use of an aqueous alkali metal hydroxide as the catalyst. The specification teaches continuously triglyceride introducing a flowing stream of aqueous alkali metal MOH -- monoglyceride saponification eM salt of fatty acids hydroxide into a flowing stream of the ester material diglyceride being subjected to molecular rearrangement. Disper 50 sion of solid hydroxide is said to occur following Rate of reaction is increased in presence of water. "flash' removal of the moisture. Reaction times of 5 minutes or less are claimed in the specification. Such MOH + free fatty acid neutralisation- M salt of fatty acids 3. short reaction times are however only obtained when relatively high catalyst concentrations with respect to 55 Removal of water from the system thus encourages the oil are employed. The process described in U.S. Pat. the equilibrium of reaction 1(a) to shift in the desired No. 2,738,278 therefore suffers from the disadvantage direction towards the M glycerolate and discourages that acceptable rates of reaction for a continuous pro reaction 2. The discouragement of the saponification cess are only achieved at the expense of high oil losses reaction reduces the amount of triglyceride and alkali due to saponification in the presence of excess hydrox metal hydroxide lost. ide. The presence of mono and diglycerides is believed to According to a first aspect of the present invention effect the rate constant of reaction 1 in two ways. there is provided a process for the interesterification of Firstly the mono and diglycerides preferentially un a triglyceride oil employing a catalyst solution compris dergo interesterification compared to triglycerides. ing a mixture of water, an alkali metal hydroxide and 65 During their interaction with the catalytic solution an glycerine, characterised by performing the process as a intermediate is formed, which is believed to be M dia continuous process comprising (i) bringing together cylglycerol, which promotes the interesterification of streams comprising respectively the oil and the catalyst the triglycerides. Secondly mono and diglycerides also 4,585,593 3 4 preferentially saponify compared to triglycerides. The The interesterification temperature is preferably in portion of mono and diglycerides which therefore un the range of from 100' to 160° C., more preferably in the dergoes saponification before the reaction is substan range of from 125 to 150° C. The temperature selected tially halted due to the removal of the water, provides depends on the overall desired reaction rate.
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