US2245538A - Recovery of higher fatty alcohols - Google Patents

Description

June 10, A1941. B', H, THURMAN 2,245,538

RECOVERY OF HIGHER FATTY ALCOHOLS Filed April l, 1941 llotum;

mantenute io, 1941 s PATENT N OFFICE RECOVERY ormonali FATTY ALconoLs Benjamin H. Thurman, Charlotte, N. C., assignor to. Refining, Inc., Reno, Nev., a corporation of Nevada F Application April ll, 1941, Serial No. 386,388 v l 13 Claims.

This invention relates to the recovery of highper fatty alcohols, and more particularly to a process by which oils or fats containing 'fatty acid radicals in combination with higher fatty alcohols are treated to form soap from the fatty acids and to recover the higher fatty alcohols substantially free from impurities. Certain oils or fats, particularly oils known as sperm oils from certain Whales, for example, whales of the genera Physeter and Hyperoodon, contain esters of certain saturated and unsaturated fatty alcohols with fatty acids, in addition to or in complete substitution of glycerol esters of fatty acids. These higher fatty alcohols, which contain from 16 to 20 carbon atoms per molecule, are insoluble in water and soluble in alcohol and ether, whereas glycerine is soluble in water. They occur as esters of saturated and unsaturated fatty acids containing from to 20 carbon atoms per m'olecule. 'Ihey have heretofore been recovered from sperm oils by saponifying the same with caustic alkali at 110 to 120 C., the sodium salts thus formed being dissolved in boiling water and thereafter decomposed with hot concentrated solutions of calcium chloride in excess, whereby the alcohols and insoluble calcium soaps of the fatty acids precipitate out together. The precipitate is filtered, dried and extracted with benzene or alcohol, the solvent is then driven ofi by heating, leaving the crude alcohol, which is then purified by crystallization from dilute alcohol. Such a process is time consuming and expensive. The sperm oil is extremely dimcult to saponify in ordinary soap kettle operations and the process requires the employment of expensive solvents, producesless valuable calcium soaps and any glycerine present is dissolved in dilute and impure solutions containing large amounts of salts, such that it is expensive and difficult to recover the glycerine.

The present process directly produces relative ly pure higher fatty alcohols, a high quality sodium soap having good detergent properties, also relatively pure glycerine Waters from which glycerine may be easily recovered, and does not require the use of solvents. The process is preferably carried out as a continuous operation in which the higher fatty alcohols, as Well as glycerine, are vaporized from the soap and condensed in relatively pure form, and high quality soap in substantially anhydrous form produced.

It is, therefore, anI object of the invention to provide a process in which fats or oils containing higher fatty alcohol esters of fatty acids are treated to saponify the fatty acids and the higher so as to recover both the soap and the alcohols in substantially pure form.

Another object ofthe invention is to provide a process of continuously saponifying'oils and fats containing higher fatty alcohol esters of fatty acids in which the alcohols are recovered directly from soluble soap and the soap produced in substantially anhydrous form,

There are two types of sperm oils, one coming from the head and the other from the blubber of whales. The head oil is more saturated in both its alcoholic and acidic components and contains the following alcohols in the form of esters with fatty acids: about 50% of cetyl alcohol CieHssOH, about l0 to 12% of hexadecenyl alcohol CisHnOl-l, about 10 to 12% of octadecyl alcohol Cial-IMOH, about 25% of octadecenyl alcohol ClaHasOH, about 2 to 3% of glycerine and the remainder as eicosenyl alcohol CzoHaaOH. 'I'he fatty acids combined with the alcohols include about 4% of capric acid Cial-12002, about 18% of lauric acid CizHziOz, about 6% of the corresponding unsaturatedacid CizHazOg, about 12% of myristic acid Cul-12u02, about 16% of the corresponding unsaturated acid CnHzsOz, about 8%.of palmitic acid Ciel-13002, about 17% of palmitoleic acid Clef-12802, a small amount of stearic acid C16, and about 10% of oleic acid CmHslOz, and a small amount of unsaturated acid CzoHssOz.

The blubber oil, as stated above, is less saturated, and the 4alcoholic constituents include about 20% of cetyl alcohol, about 20% `of hexadecenyl alcohol, a small am'ount of octadecyl a1- cohol, about of octadecenyl alcohol and ,about 10% of unsaturated alcohols containing 20 carbon atoms as well as 3 to 4% glycerine. The fatty acids resemble those of ordinary Whale oil more closely than those of sperm head oil but are not so highly unsaturated as the former. They contain about 1% of lauric acid, about 3% of myristic acid, -about 3% of the corresponding unsaturated acid C14Hze02, about 8% palmitic acid, about 24% of palmitoleic acid, about 35% of oleic acid and about 10 to.12% each of arachidic (C20) and behenic (C22) acid series.

the head oil contains about 26% of glycerides and 74% of higherfatty esters and the blubber oil contains about 34% of glycerides and 66% of higher fatty acid esters. It will be noted that the alcohols of the head oil are pre' dominantly saturated alcohols, mostly cetyl alcohol, whereas the alcohols of the blubber oil are predominantly an unsaturated alcohol, namely octadecenyl, and that the acids of the blubber oil are vmuch less saturated than those of the head oil. Either of these oils may be hydrogenated to saturate both the alcoholic and acidic components to any desired degree before treating the samge by the present process so that more highly saturated alcohols are produced, as well as soap containing more highly saturated acids.

or the alcoholic component can be hydrogenated after separation from the soap.

The present invention will be described in conjunction with a suitable apparatus diagrammatically shown in the accompanying drawing. Referring to the drawing, a source of supply of oils containing esters of higher fatty alcohols and fatty acids is shown as a tank I provided with a heating coil I I so that the oils may be maintained in fiowable condition. A source of supply for alkalies, such as caustic soda solution, is shown as a tank I2 provided with a heating coil I3 so that the alkali solution will be brought to the desired temperature. In an operation including continuous saponiiication, proportioned streams of oil and alkali may be withdrawn from the tanks I0 and I2 through pipes Il and I5, respectively, by proportion pumps I6 and I1, respectively, and forced under pressure through preheating` coils I9 and I9, respectively. The pumps I6 and I1 are shown, by way of example, as being driven by a variable speed electric motor 29 with a variable speed device 2| positioned between the pumps so that any desired amounts and proportions of oil and alkali can be introduced into the process. Any other type of known or suitable proportioning mechanism can be substituted for that shown.

The heating coils I8 and I9 may be heated by any suitable means, for example, burners 22 for gaseous or liquid fuel. The oil is preferably heated in the coil i8 under flow conditions to avoid local overheating to temperatures ranging from 250 to 300 F. so as to provide for rapid saponiiication when the oil is contacted with alcohol and to also prevent the formation of viscous soap masses, which tend to form at lower temperatures. The alkali solution is also preferably preheated in coil I9 so as not to chill the oil when brought in contact therewith. Since the alkali solution is extremely corrosive at high temperatures it is preferred to preheat the oil to a somewhat higher temperature than that necessary to produce a flowable soap mixture to enable the alkali solution to be preheated to a somewhat less temperature, for example, temperatures not in excess of 200 F., and still form a fiowable soap mixture. The preheated oil and alkali are preferably mixed in a closed ilow mixer 23 by jetting a stream of one material into a stream of the other although any type of flow mixer, for example, a closed mechanical mixer provided with agitators, can be employed so long as air is prevented from contacting the materials at the high temperatures employed. Saponication of the oil is rapid and substantially complete in the mixer 23 and a fiowable mixture containing soap, higher fatty alcohols and small amounts of glycerine is produced which may also contain portions of unsaponiiied oil. A pump 24 is preferably employed for forcing the resulting mixture through another heating device such as a coil 25 heated lin a desired manner, for example, by burner 22. The temperature of the mixture is increased in the coil 25 and saponication of any unsaponified materials completed. It is preferred not to raise the temperature in the coil above that at which decomposition of esters or fatty acids will Vtake place. Thus, temperatures between 350 to 420 F. can be employed. It is preferred to maintain a relatively high pressure in this coil to prevent the formation of substantial amounts of vapors therein; thus pressures ranging between 125 to 350 pounds per square inch can be satisfactorily employed. The pump 24 produces a further mixing action, and any further mixing which takes place during stream ilow in the coil in conjunction with the high temperatures employed, results in a substantially complete saponified mixture leaving the coil 25. tially completely saponified mixture may then be pumped by means of a pump 26 through another heating device shown as a heating coil 21 in which the temperature of the mixture is further increased. The temperature employed in coil 21 will ordinarily range between 500 and 650 F. although in certain cases temperatures as high as 700 F. may be necessary. Since the mixture has previously been substantially completely saponified, decomposition of esters orl fatty acids is avoided.- Heat may be applied to the heating coil 21 by a burner 22.

Substantially all of the higher fatty alcohols, glycerine and water, as well as any other vaporizable materials contained in the mixture, are evaporated when the heated mixture is discharged into an evaporatlng chamber 29. The pressure in coil 21 may be as low as or somewhat lower than that in the coil 25 so that a portion of the vaporizable materials are vaporized in the coil 21, thus enabling more heat to be supplied to the mixture at the temperature employed and reducing the amount of heat necessary to be supplied in the evaporating chamber 28 in order to vaporize substantially Vall of the vaporizable materials. Pressures ranging from 250 pounds down to almost atmospheric pressure at the outlet of the coil can be employed, although due to the frictional head in the coil, the pressures at the inlet thereof will be somewhat higher.

A vacuum is preferably maintained within the evaporating chamber 20 by removing vapors through the pipe 29 and condensing the same in one or more condensers 30 supplied with receivers 3| connected to a vacuum pump 32. VThe evaporating chamber is also preferably supplied with a heating jacket 32 through which any desired heating medium, such as superheated steam or heated mineral oil, may be circulated by pipes 34 and 35. The heated mixture coming from the coil 21 is preferably directed against the heated Walls of the evaporating chamber by nozzles 36 positioned adjacent said walls. In order to completely remove the alcohols, glycerine, etc., it is usually necsary to maintain the temperature of the separated soap in the vacuum chamber suiliciently high to cause the same to be in liquid form after the vaporizable materials have been removed. Thus, temperatures between 420 and 600 F. must ordinarily be employed in the evaporating chamber. It will be noted that the liquid soap ilows down the heated walls of the evaporating chamber as a lm such that vapors are readily released therefrom and that the vapors can pass inwardly and upwardly to the pipe 29 through a substantially unimpeded path in the evaporating chamber.

The soap is thus deposited in the evaporating chamber in liquid anhydrous form and will continuously flow into the casing 31 of a screw conveyor 38. The casing 31 is connected to the evaporating chamber in fluid-tight relationship such that the casing 31, for example, forms a part of the evaporating chamber. A cooling jacket 39 through which any desired cooling medium, such aswater, can be circulated is preferably positioned around the discharge end of the conveyor housing 31 to cool the soap being discharged therefrom, and the portion 40 of the conveyor The substan- Y is preferably enlarged Vevaporating chamber had a temperature` of 450 shaft adjacent the discharge end of the conveyor to provide a restricted passageway 4I for the. cooled soap. By forcing .the cooled soap. through such a restricted 4eway 'an effective vacuum seal is formedl vso that the soap can be continuously removed from the evap` i orating chamber during operations without breaking the vacuum. A manually operated valve 42 in the discharge endof the conveyor housing' 311s preferably provided 'so 'that it may be closed during starting andl stopping of the process to maintain a vacuum in the evaporating chamber- F. vDuring this run the pressure at the entrance of the coils I8 and I8 was 200 pounds per square inch, the pressure at the outlet of coil was 250 pounds per square inch and the pressure on the mixture Just before it entered the evaporating chamber 48 was 40 pounds per square inch. The

v vacuum in the evaporating chamber was maintained at 281/2 inches mercury.

when insumcient soap is present in the restricted l passageway 4I. The valve 42 is normally open during operation of the process. The soap dis-4 charged from the conveyor housing'41 shouldl be sufficiently cooled so-th-at ituisnot damaged byv contact with the atmosphere and in general its temperature must be as low as 120 F. `The soap produced is readily soluble in water and can be The soap produced was light in color, readily soluble in water and has good detergent properties. The condensate was milky when withdrawn from the receiver 3l but settled cleanly into an upper layer of pale yellow fatty alcohols land a lower one of water containing a small y amount of soap and glycerine. Such a condensate is readily susceptible to centrifugal separahydrated if desired to form bar, vpowdered or granular soap. It is light colored and of an The fatty alcohols resulting from the settling or'centrifugal separating operation are mixtures of the higher fatty yalcohols in substantially the vsame proportions that occur in the original oil,

agreeable odor and has excellentvdetergent proper-ties. l

The vaporizable materials are condensed in the condenser and cooled in the receiver 3i'. The

condensate will settle cleanly into an upper layer of pale yellow fatty alcohol and a lower layer of water containing a small amountof glycerine and soap. It may be withdrawn from the receiver 3i through a pipe 43`by any desired means, such as a pump 44. For example, the condensate can be continuously withdrawn and subjected to con-- tinuous centrifugal separation in a centrifugal separator 45. The higher fatty alcohols are conand this mixture will depend upon the type of sperm oil employed. If substantially pure cetyl alcohol, for example, is desired, the hea'd oil would be employed which contains nearly 50% of cetyl alcohol, and the various other alcohols can be separated therefrom by fractional distillation under vacuum conditions. Another way to producel substantially pure cetyl alcohol is to first produce spermaceti from the head oil by'chilling y the sperm oil for several weeks and then pressing A. it cold (about 0 C.) then repressing the residual tinuously discharged as the lighter vaffluent` lthrough a spout 46 into a receptacle 41 and the water, soap and glycerine layer discharged as the heavier aiiiuent .through a spout 48 into a receiver 49. A somewhat cleaner separation can `be effected bythe centrifugal-separator and the entire process is continuous from the introduction of the materials therein to the production of high quality, higher fatty alcohols and high quality anhydrous soap. rThe water layer containing small amounts of soap and glycerine may be. con.

centrated and glycerine separated from the soap in any desired manner. vThis can be` simplyv done as the glycerine and soap are not contaminated by large amounts of other impurities.

As a specific example of a process in accord- -ance with the present invention, sperm oil in the cakes at approximately 15 C. to remove more oil.

v'I'.he residue is largely spermaceti which may be ing the variousfatty alcohols so as to first protank I0 was heated by the coil H to a temperature of 190 F. so as to render the same flowahle and reduce the amount of heat which was necessary to add during the rest of the process. A solution of 31.76% sodium hydroxide was supplied from the tank 1 2 at approximately room temperature. Approximately 8 pounds of sperm oil per minute was pumped through the coil I8,

wherein it was preheated to 280 F. The speed of the proportioning pump l1 was adjusted until the proper proportion of lye solution to produce a substantially neutral soap was pumped through lthe coil I9 in which it waspreheated to 175 F.

These materials were mixed in a flow mixer 23 and heated in .the coil 25 so that the discharge temperature therefrom was 450 F. It was then -pumped through the coil 21 wherein additional heat was supplied and the mixture was discharged from the coil at 585 l5'. Mineral'oil was used in the heating jacket 32 around vthe Y evaporating chamber 28 and was maintained at a temperature of 475 F. The vapors from the duce a mixture of said alcohols, which may be later separated if desired. This mixture can be hydrogenated if it is desired to produce a mixture of wholly or partially saturated alcohols hav-ing properties very similar to pure cetyl alcohol.

Several modifications of the above described -process are possible. For example, the sperm oil and saponification reagent maybe mixed in proper proportions in a batch mixing device, such as a soap kettle', wherein they are heated or maintained at a temperature sufficiently high, or in the presence of sufficient water, or both, to form a fiowable mixture. 'I'hat is, temperatures approaching the boiling point of Water may be employed. Some saponication may take place in such kettle but complete saponiiication is unnecessary. By maintaining sumcient agitation, a substantially uniform mixture may be continuously pumped from the kettle through the coils 25 and 21 wherein substantially complete saponication isl effected and the temperature raised sumcient to cause separation of the alcohols as vapors in the evaporating chamber 28, as above described. Also, the coils 25 or 21 may be employed to completely saponify a mixture from either a continuous or batch mixer and the resulting soap mixture cooled, for example, in a cooling coil, before contacting the same with the atmosphere, and then treated to separate alcohols and form insoluble soap in accordance with prior practices above described. 'This procedure enables a substantiallycompletely saponiiled mixture to be quickly produced but does not avoid the employment of solvents or the production of less valuable insoluble soap. The combination of rapid and substantially complete saponication with vaporization of the alcohols from soluble soap does, however, rapidly produce high quality soluble soap and substantially pure alcohols.

While in the preferred operation the oil is preheated in the heating device I8 and the mixture subsequently heated in the heating device A5 to a temperature which insures substantially complete saponication therein, it is apparent .that all of the heat necessary for such reaction can be supplied in the preheating coil I8 since the reaction temperatures are below those which cause substantial decomposition of fatty materials under the conditions in the present process. Thus the temperature of the saponiable material can be raised in the preheating coil to a temperature which, when .the heated material is mixed with the saponifying material, will produce the desired reaction temperature in the coil 25, for example, 350 to 420 F., so that no further heat need be applied in the coil which can function merely as a reaction zone. 'I'he reacted mass can then either be further heated in the heating device 21 in order to separate vapors inthe vapor separating zone 2l, it can be introduced directly into the vapor separating zone to at least partially separate vapors, or can be cooled and discharged from the system.

This application is a continuation-impart of my copending application Serial No, 180,231.

While I have disclosed the preferredvembodiments of my invention, it is understood that the details thereof may be varied within the scop of the following claims: y

I claim:

1. The process of producing substantially pure higher fatty alcohols and high quality soap, which comprises, forming a mixture of an oil containing higher fatty alcohol esters of fatty acids and sufficient alkali to substantially completely saponify said esters, saponifying said esters by pumping a stream of said mixture through a heating zone under pressure, supplying suiiicient heat to said heating zone to substantially completely saponify said mixture and raise the temperature thereof suilicient to cause said alcohols to separate in vapor form as soon as saidV pressure is reduced, any heating of oil or fatty material substantially above the boiling point of water being effected during stream ow thereof, discharging said heated mixture into an evaporating zone at a lower pressure wherein said alcohols are substantially immediately separated in vapor form from the resultant soap, and continuously withdrawing and condensing said vapors.

2. 'I'he process of producing substantially pure mixtures of higher fatty alcohols, which comprises, forming a mixture of an oil cointaining higher fatty alcohol esters of fatty acids and av saponifying reagent, saponifying said esters by continuously pumping a stream of said mixture under pressure through a heating zone, supplying suilicient heat to said zone and maintaining said mixture under sufficient conditions of movement to rapidly and substantially completely sapcnify said mixture, thereafter pumping the resulting mixture through a second heating zone and increasing the temperature of said mixture suiiicient to cause said fatty alcohols to be separated in vapor form as soon as said pressure is reduced, discharging the resulting heated mixture into an evaporating zone under a. reduced pressure wherein said higher fatty alcohols and water are substantially immediately separated in the form of vapors from the resulting soap, continuously removing said vapors from said evaporating zone and condensing the same to form a liquid mixture containing said higher fatty alcohols and water, and .separating said higher alcohols from said water by difference in specific gravity.

3. The process of producing soap and substantially pure mixtures of higher fatty alcohols from oils containing substantial quantities of higher fatty alcohol esters of fatty acids, which comprises, forming a mixture of said oil and an aqueous saponifying reagent, saponifying said esters by pumping a stream of said mixture under pressure through a heating zone, imparting sumcient heat in said zone to substantially completely saponify said mixture and raise the temperature thereof suil'icient to cause said higher fatty alcohols and water to be separated in the form of vapor from the resulting soap when the heated mixture is introduced into an evaporating chamber in which a vacuum is maintained, introducing said heated mixture into said exaporating chamber, maintaining the temperature in said evaporating chamber sufliciently high to cause said soap to be deposited in substantially anhydrous molten form after said alcohols and water have been separated therefrom, continuously withdrawing said vapors from said evaporating zone at a rate sufficient to maintain said vacuum, condensing said vapors to form a mixture of higher fatty alcohols and water, separating said alcohols from said water by difference in specific gravity, continuously removing said soap from said evaporating chamber without breaking said vacuum and cooling said soap during removal and while still anhydrous below a temperature at which it will be damaged by contact with the atmosphere.

4. The process of saponifying oils consisting predominantly of higher fatty alcohol esters of fatty acids to produce high quality soap and substantially pure mixtures of higher fatty alcohols, which comprises, heating a. flowing stream of said oils out of contact with the atmosphere to a temperature between approximately 250 and 300 F. at which substantially instantaneous saponiflcation of said oils will take place when the same are mixed with a saponifying reagent, continuously admixing a stream of saponifying reagent with a stream of the heated oils to produce said saponication, thereafter raising the temperature of the resulting mixture sufiicient to cause substantially immediate separation of water and said alcohols in vapor form from said soap under vacuum conditions, introducing said heated mixture into an evaporating chamber in which a vacuum is maintained and continuously separating said vapors from said soap and withdrawing the same from said evaporating chamber at a rate sumcient to maintain said vacuum, condensing said vapors to form a mixture of water and higher fatty alcohols, and separating said higher fatty alcohols from said water by difference in specific gravity.

5. The process of saponifying oils containing substantial quantities of higher fatty alcohol esters of fatty acids, which comprises, saponifying said oil by flowing a stream of a mixture of said oil and suicient alkali to substantially completely saponify said esters through a heating zone under pressure, maintaining suilicient substantial quantities of higher fatty alcoholv4 esters of fatty acids, which comprises, forming a mixture of said oils and sufilcient alkali to substantially completely saponify the same, saponifying said mixture by` pumping a stream of said mixture through a heating zone under pressure, supplying sufcient heat to sai d mixture in said heating zone to substantially completely. saponify the same while maintaining sufficient movement of said mixture in said heating zone to prevent local overheating thereof, any heating of the oils or mixture containing fatty materials to a temperature substantially above the boiling point of water being effected during stream ilow thereof and thereafter separating alcohols liberated during said saponication from said soap. l

"I, The process of saponifying oils containing substantial quantities of higher fatty alcohol esters of fatty acids to produce soap and higher fatty alcohols, which comprises, continuously mixing a stream of said oil and a stream of said alkali at an elevated temperature and out'of contact with the atmosphere, passing the resulting mixture through a heating zone under pressure and with suillcient movement to maintain a substantially uniform mixture, supplying sufficient heat to said mixture in said heating zone to substantially completely saponify said oil to form soap and liberate said alcohols, anyheating of the oils or mixture containing fatty materials to a temperature substantially above the boiling point of water being effected during stream flow thereof.

8. The process of saponifyingoils containing substantial quantities of higher fatty alcohol esters of fatty acids to produce soap and higher alcohols, which comprises, continuously mixing a stream of said oil and a stream of said alkali at an elevated temperature and out of contact with the atmosphere, passing the resulting mixture through a heating zone under pressure and with sufcient movement to maintain a substantially uniform mixture, supplying suflioient heat to said mixture in said heating zone to substantially completely saponify said oil to form soap and liberate said alcohols, any heating of the oils or mixture containing fatty materials to a temperature substantially above the boiling point of water being effected during stream flow thereof and thereafter separating said alcohols from said soap.

9. The process of saponifying sperm oil -to produce high quality soap and substantially pure higher fatty alcohols, which comprises, forming a mixture of said sperm oil and sufiicient alkali to substantially completely saponify said oil, saponifying said oil by pumping a stream as said pressure is reduced, any heating of the oils or mixture containing fatty materials to a temperature substantially above the boiling point of water being eected during stream f'iow thereof, dischargingthe heated soap mixture into an evaporating zone wherein a vacuum is maintained and said alcohol is separated in. vapor form from said soap and continuously withdrawing and condensing said vapors to maintain said vacuum.

10. The. process of saponifying sperm oil, which comprises, forming a mixture of said oil and sufilcient alkali to substantially completely saponify said oil, saponifying said oil .by continuously pumping said mixture through an elongated heating zone under pressure, and supplying sufficient heat to said heating zone and maintaining said mixture in said zone in sufficient state of movement to substantially completely saponify said mixture, any heating of the oils or mixture containing materialsto a temperature substantially above the boiling point of water being effected during stream flow thereof.

11. The process of saponifying oils containing substantial quantities of higher fatty alcohol esters of fatty acids, which comprises, forming a mixtureof said oil and sufficient alkali to substantially completely saponify said oil, saponifying said oil by continuously pumping said mixture through a reaction zone under pressure,

maintainingfsuicient movement of said mixture substantial quantities of higher fatty alcohol esters of fatty acids, which comprises, saponifying said oil by flowing a stream of a mixture of said oil and suillcient alkali to substantially completely saponify said esters through a reaction zone under pressure, maintaining sufficient movement of the resulting mixture in said heating zone and preheating at least said esters prior to mixing the same with said alkali to supply sufncient heat to said mixture in said zone in substantially completely saponify the same, any heating of the oils or mixture containing fatty materials to a temperature substantially above the boiling point of water being enected during the stream flow thereof.

13. The process of saponifying oils containing substantial quantities of higher fatty alcohol esters of fatty acids, which comprises, forming a mixture of said oil and sumcient alkali to substantially completely saponify said oil, saponifying said oil by continuously pumping said mixture through a reaction zone under pressure, maintaining sumcient movement of said mixture in said reaction zone and subjecting the mixture therein to a sufficiently high temperature to substantially completely saponify said mixture, any heating of the oils or mixture containing fatty material to a temperature substantially above the boiling point of water being effected 'during stream flow thereof, further heating the substantially completely saponified mixture and separating the liberated alcohols in vapor form from the resultant soap.

BENJAMIN THURMAN.

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