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A unique process of soapmaking, based on the methyl ester saponification method, is described here. High-quality toilet soaps can be produced from palm stearin and palm kernel oil as well as tallow and coconut oil. C-SFMe is a promising surfactant for detergents and will contribute to expanding the use of palm oil in the near future.
A unique process of soapmaking, based on the methyl ester saponification method, is described here. High-quality toilet soaps can be produced from palm stearin and palm kernel oil as well as tallow and coconut oil. C-SFMe is a promising surfactant for detergents and will contribute to expanding the use of palm oil in the near future.
A unique process of soapmaking, based on the methyl ester saponification method, is described here. High-quality toilet soaps can be produced from palm stearin and palm kernel oil as well as tallow and coconut oil. C-SFMe is a promising surfactant for detergents and will contribute to expanding the use of palm oil in the near future.
S o a p a n d R e l a t e d P r o d u c t s : P a l m a n d L a u r i c O i l
T. OGOSHI and Y. MIYAWAKI, Process Development Laboratory, Lion Corporation,
No. 13-12, 7-chome, Hirai, Edogawa-Ku, Tokyo, 132, Japan 331 ABSTRACT There are three main methods for producing soap: direct sapon- ification of fats and oils, neutralization of fatty acids and saponifica- tion of fatty acid methyl esters. Our unique process of soapmaking, based on the methyl ester saponification method, is described here. By this process, high-quality toilet soaps can be produced from palm stearin and palm kernel oil as well as tallow and coconut oil. A new sulfonation process was developed to produce high-quality c~-SFMe (c~-sulfo fatty acid methyl ester) from palm stearin as the starting material. Quality and performance of ~-SFMe bear com- parison with those of LAS, AES, AS or AOS. Thus c~-SFMe is a promising surfactant for detergents and will contribute to expanding the use of palm oil in the near future. I NTRODUCTI ON Fat t y acid met hyl esters have been used mai nl y as inter- medi at es f or f at t y alcohols. Fr om t he vi ewpoi nt s of physi cal and chemi cal propert i es, f at t y acid met hyl esters have t he fol l owi ng advantages as compar ed wi t h f at t y acids: easy t o handl e because of l ower melting poi nt s, mor e stable in storage, noncorrosi ve in t he equi pment used, and easy t o distill because of l ower boiling poi nt s. Two r out es are available f or manuf act ur i ng f at t y acid met hyl ester: est eri fi cat i on of f at t y acid obt ai ned by fat-splitting, and di rect i nt erest eri fi cat i on of fats and oils wi t h met hanol (met hanol ysi s process). Accor di ng t o t he l at t er rout e, met hyl esters wi t h t he above-ment i oned advantages can be pr oduced at relatively l ow costs. Thus t he esters have been reevaluated as i nt ermedi at es f or various f at t y acid derivatives. Among t he raw materials f or fats and oils, pal m oil has been gaining at t ent i on as a material f or soaps and det ergent s since t he recent increase in its pr oduc- t i on in Malaysia. The present paper report s on a uni que process of soap- maki ng via f at t y acid met hyl ester and t he devel opment of ~-sulfo f at t y acid met hyl ester (cX-SFMe) derived f r om pal m oil, whi ch is hi ghl y promi si ng as a surfact ant f or detergents. METHYL ESTER SAPONI FI CATI ON PROCESS Soapmaking Process There are t hree met hods f or manufacturing neat soap (65-70% anhydr ous soap): di rect saponi fi cat i on of fat s and oil, neut ral i zat i on of f at t y acids and saponi fi cat i on of f at t y acid met hyl esters (Fig. 1). The first t wo met hods are commonl y used in soap i ndust ry. Direct saponification. This is a t radi t i onal l y used met hod in whi ch fats and oils are saponified wi t h alkali sol ut i on t o yi el d f at t y acid alkali salt (soap) and gl ycerol . This met hod requires compl ex pr ocedur es of salting out and washing t o recover t he gl ycerol f or med by saponi fi cat i on and t o remove impurities f r om t he soap. In large-scale pr oduct i on, cont i n- uous met hods are used, i.e., t he Sharpies process, DeLaval process and Monsavon process are t ypi cal (1). Fatty aci d neutralization method. Fat t y acids are neutralized wi t h alkali sol ut i on t o make soap. Mainly used are distilled f at t y acids made by cont i nuous hydr ol i zat i on of fat s and oils at high t emper at ur es (250 C) and under high pressures (50 kg/ cm 2) wi t hout catalysts. No salting out or washing procedures t hat are required in di rect saponi fi cat i on are needed. Since f at t y acids have undesirable propert i es such as relatively high mel t i ng poi nt , t her mal change in qual i t y and corrosive act i on, pr oper at t ent i on shoul d be gwen t o their handling. Typi cal cont i nuous processes are t he Fats and Oils I r A,,a,, So,n c " ' O e O . I F t t y o c , 0 s I [ M o t h y , e s t e r s I > Neat Soap 1 Bar Soaps F I G. 1 . Ma n u f a c t u r i n g p r o c e s s e s o f n e a t s o a p f r o m f a t s a nd o i l s . Mills process (P & G), t he Mazzoni SC process and t he Ar mour process (2). Methyl ester saponification method. The t hi rd met hod is t o interesterify fats and oils using met hanol t o pr oduce met hyl ester whi ch is t hen saponified wi t h alkali sol ut i on t o pr oduce neat soap. This met hod has been vi gorousl y studied in t he U.S.A. since 1940 but t he met hod seemed not t o come of f well. Li on Cor por at i on succeeded in t he industrial appl i cat i on of t he cont i nuous process of met hyl ester saponi fi cat i on in 1960 (named ES-process). Fol l owi ng accumul at ed i mprovement s, t he process now pr oduces good-qual i t y met hyl ester t o manuf act ur e hi gh-qual i t y t oi l et soaps in large scale (3). ES-Process A schemat i c fl ow diagram of t he ES-process is shown in Figure 2. The ES-process consists of est eri fi cat i on of free f at t y acids, i nt erest eri fi cat i on of fats and oils, saponi fi cat i on of f at t y acid met hyl ester and r ecover y of gl ycerol and met hanol . Chemical react i ons in each step are shown in Figure 3. Esterification of free fatty acids. This pr ocedur e is a prel i mi nary t r eat ment f or t he i nt erest eri fi cat i on o f fat s and oils. Free f at t y acids cont ai ned in fat s and oils, whi ch i nhi bi t t he cat al yt i c act i on of t he alkali in t he next interesterifica- t i on procedure, are convert ed i nt o met hyl esters by ester- ification. Characteristically, in this step a special synt het i c resin is used as cat al yst . Fat s and oils cont ai ni ng free f at t y acids are mi xed wi t h met hanol and convert ed i nt o met hyl ester by cont i nuous passage t hr ough t he packed col umn of t he cat al yst resin. The l ow react i on t emper at ur e of 60 C prevent s degradat i on of t he raw oils and t he fixed cat al yst bed eliminates t he need f or cat al yst fi l t rat i on and separat i on. JAOCS, Vol. 62, no. 2 (February 1985) 3 3 2 T. OGOSH1 AND Y. MIYAWAKI { Atkali M e O H ~ [ Alkali Soln. I ~ I Y ~ MeOH Recovery ~ ~ I I L - - - , I I Neat Soap I , ' , , / ;eparator I Separator Rectifying MeOH CoIumn Recovery 1 st. Stage-Reactor Sweet Water Waste Water FIG. 2. Schematic flow diagram of the ES-process. ( 1 )- Est er i f i cat i on RCOOH + CH30H ~RCOOCH3 + H20 (FFA) (2) I nt er - est er i f i cat i on RCOOCHz CH20H I l RCOOCH + 3CH30H , 3RCOOCH3 + CHOH I I RCOOCH2 CH20H (3) Saponi f i cat i on RCOOCH3+NaOH , RCOONa + CH30H FIG. 3. Chemi cal reacti ons in each step o f t he ES-process. Interesterification o f fats and oils. Processed fats and oils are converted into met hyl esters by interesterification with met hanol together with a small quant i t y of NaOH as catalyst at 60 C and under approxi mat el y atmospheric pressure. The raw oil conversion rate into met hyl ester is at most 96% in the one-stage reaction owing to the chemical equilibrium. To circumvent such chemical equilibrium, .a t wo-st age reaction is used in which t he glycerol formed in the initial reaction is continuously removed in a specially designed separator and interesterification is again performed, achiev- i ng a high conversion rate of more t han 99%. On the ot her hand, colored mat t er and impurities are occluded in a small quantity of the soap formed by t he action of the alkali catalyst, yielding a dark brown layer separated f r om t he ester layer during the process of separation. This refining action yields light-colored met hyl esters at a high conversion rate. Interesterification is t he most i mport ant procedure in the ES-process. Saponification of fatty acid methyl esters. Methyl ester and alkali solution are supplied t o t he saponifier at a con- stant rate with rapid saponification at 100 C. The met hanol secondarily produced in the reaction is recovered in a met h- anol recovery vessel, yielding neat soap with more t han a 99% saponification rate. Glycerol~methanol recovery. The lower layer discharged f r om the separator contains met hanol , glycerol, soap and water. The met hanol contained in the lower layer is re- covered in a met hanol recovery t ower and yields sweet wat er as its residue. The sweet water is treated with sulfuric acid t o yield 70% crude glycerol and a dark oil layer with accu- mulated impurities. The dark oil is used for lower grade soap. The met hanol recovered is rectified and reused. Advantages of the ES-process. 1. Methyl ester/soap of light color can be obtained in high yield. 2. Soap obtained has a good color and excellent quality stability because the low t emperat ure during the process prevents degradation of the oil and met hyl ester, and also because met hyl ester is considerably refined in t he inter- esterification step. 3. Glycerol of high concentration (more t han 70%) is recovered in good yield. 4. Fat t y acid met hyl ester can be distilled and refined if necessary, allowing the use of raw oils. 5. No corrosion occurs in the equipment. 6. Methyl ester used as t he intermediate is more stable in storage and easier t o handle than f at t y acids because of low melting point. 7. The low t emperat ure and atmospheric pressure re- quired for t he process allow easy plant maintenance. We are manufacturing quality toilet soaps by this ES- process using tallow and coconut oil as the base materials. Recently palm oil has been gaining at t ent i on as a raw material for soap. We have conduct ed trial product i on of soap using pal m stearin and palm kernel oil by the ES- process and have confirmed its quality is as high as t hat of s oa pf r om tallow and coconut oil. DEVELOPMENT OF c~-SFMe Background As shown in Figure 4, one of the derivatives developed from f at t y acid met hyl ester is a-sulfo f at t y met hyl ester (a-SFMe), an anionic surfactant formed by sulfonation of f at t y acid met hyl ester. At present, linear alkylbenzene sulfonate (LAS), alcohol et hoxy sulfate (AES), alcohol sulfate (AS) and a-olefin sulfonate (AOS) are mainly used as anionic surfactants for detergents. Most of these materials have been synthesized starting from petroleum. Since the oil crisis in 1973, however, natural fats and oils have been reevaluated and a-SFMe syn'thesized from fat s and oils has been gaining at t ent i on as a raw material, a-SFMe, though its synthesis had been long known and studied, posed probl ems to be solved in t erms of its quality such as unsatisfactory color and bypr oduct of di-sodium a-sulfo f at t y acid (a-SFNa2) of low performance. JAOCS, Vol. 62, no. 2 (February 1985) SOAP AND RELATED PRODUCTS 3 3 3 Palm oi l Palm kernel - oi l Coconut oi l Beef t al l ow etc. J i I I J I . . . . - ~ ( S p l i t t i n g ~ * { E s t e r i f i c a t J o n . ) FIG. 4. Derivatives from fat t y acid methyl esters. ~ ~ Soaps l - ' - ' ~ ~ 1 Ct-SFMe I . , c o . o . s l O t h e r s RCH~COOR' [ I ] _s o~t ~+so3 ~'e e OR' ~CHC,(: s o ? [ H ] i ~-e "O o~+SOa ~ c . ~ B " s o ~ [.~ 3 SO3H SO3H NaOH I NaOH SO3Na SO~Na [ ~ . N a ] [ Z ] [ ~ ] FIG. 5. Mechanism of sulfonatlon o f f at t y acid esters (6). New ~-SFMe Process Palm stearin or beef tallow is used as t he starting material. Hardened pal m stearin met hyl ester is sulfonated by gaseous sulfur trioxide t o give a-SFMe. Several studies (4-7) have been report ed on t he mechanism of this reaction, which has not yet been fully clarified. One of t he previously reported mechanisms is shown in Figure 5 (6). Most of the reports commonl y suggest t hat the reaction occurs via an interme- diate with 2 moles of SO3 and neutralization wi t hout elimi- nation of the SO3 added to the met hyl ester group forms a bypr oduct cz-SFNa2 (di-salt). This suggestion reasonably explains the phenomenon, though t he structural formul a of the intermediate is not fully clarified. Figure 6 shows t he schematic flow diagram of the newly developed c~-SFMe. The sulfonating agent, SO3 gas, is manu- factured by t he sulfur burning process. Palm stearin met hyl ester is supplied t o t he sul fonat or where it is sulfonated by the SO3 gas. The sulfonator is a fi l m-t ype reactor originally developed by Lion for sulfonation of such surfactants as AOS and AES [named T. O. -Reactor (8)]. It allows mild sulfonation by controlling the reaction temperature. The sulfonated substance separated from exhaust gas in the gas- liquid separator is transferred t o the specially designed acid- t reat ment unit, where the sulfonated substance is sufficiently mixed with met hanol and a small quant i t y of hydrogen peroxide. Remarkable bleaching effect is obtained in this step. The bleached substance is neutralized by vigorous mixing with NaOH solution in the neutralizer. Lastly, the methanol contained in the neutralized slurry is recovered in the met hanol recovery uni t giving a high concentration (50-60% A.M. content) of c~-SFMe slurry wi t hout cz-SFNa2. Typical qualities resulting from this process (9) are shown in Table I. Its advantages are: The manufact ure of a-SFMe containing substantially no ~-SFNa2, previously considered impossible, is made possible. The process allows the manufact ure of cx-SFMe of good color, comparable t o t hat of petroleum-derived sur- factants such as LAS. Slurry obtained has 60% active mat t er, compared with the former maxi mum cont ent of 35%. A continuous sulfonation plant t hat is used for LAS, OcrLJ Blower Storage Tank Storage Tank FAMe = Fatty Acid Methytester cnverter Burner H E. H.E. Effluent Gas Cleaners ~ - - - ~ f - - to Condense~ ~S~aratorr___l ~ L ~ - ] i '~ I ] I MeOH Reactor T I I I I ] Recovery Unit Acid Treat ment Unit Storage Tank FIG. 6. Schematic flow diagram of the newly developed process for c~-SFMe. J AOCS, Vot . 6 2 , no. 2 ( Febr uar y 1 9 8 5 ) 334 T. OGOSHI AND Y. MIYAWAKI TABLE I Typi cal Qualities of ~-SFMe New process Previous process Active mat t er (%) { ~-SFMe (%) ~-SFNa 2 (%) ~-SFMe x lO0 (%) c~-SFMe + c~-SFNa 2 Col or (5% Kl et t ) a Un-reacted oil 55 35 55 f 26 t race 9 ca. 100 74 50 200 (%)b 1.6 3.0 Raw mat eri al : Pal m st eari n met hyl est er ( har dened, distilled). a5% A.M. soln., 40 mm cell, No. 42 Blue fi l t er. b% based on A.M. 1 0 0 , ,,,,, 100 90 80 g ~ 7o 60 56 C16 oo/o 5O/5o O/loo a-SFMe- Na/~- SFN a~(%) 9o : ' T A E S (Cl1-153.EO) c ~ \ ~ - ' OSFMe / Ha r d e n e d ~ ~ l ~ l \ t a l l o w ] e# 70 t 3 60 ~ O OA S (Coco al c) 50 ~ ~ , ....%oap f { , , 0 40 8 0 120 160 2 0 0 2 4 0 280 3 2 0 3 6 0 CaCO3 p p m FIG. 7. Water hardness vs. detergency of surfactants in phosphate- free formulation (I0). 2 0 . . . . . . , . . . . . z 2 15 10 5 c~e ~ oo/ o 50/ 50 % oo a - S F Me - Na / a - S F Na 2 ( %) FI G. 8. Effect of bi nar y system c~-SFMe/a-SFNa2 on det ergency and foaming pr oper t i es in phosphat e-free f or mul at i on (6). (Water hardness 54 ppm) AES, etc. , can be used f or t he pr oduct i on of a-SFMe wi t h some addi t i onal equi pment s. a- SFNa2 cont ent can be cont rol l ed in t he range o f 0-50%, i f necessary, by changing condi t i ons. e-SFMe wi t h good odor is obt ai ned. The qual i t y disadvantages of ~-SFMe, i.e., bypr oduc t t o be cont rol l ed and col or i mpr ovement , have been solved by t he devel opment of this process. A d a p t a b i l i t y o f ~ - S F Me t o Det er gent s ~-SFMe is available as a surfact ant f or det ergent s wi t h t he fol l owi ng advantages: It has high det er gency and hard wat er resistance (Fig. 7). As t he or der o f excellence is C16 ~-SFMe > C18 ~-SFMe > C14 ~-SFMe in t erms of det er gency and foami ng, beef t al l ow and pal m stearin composed o f C16 and C18 car bon chai n are best as t he raw oils. Not e t hat an increase in ~-SFNa2 leads t o a sudden l oweri ng of per f or mance, so t hat t he subst ance shoul d be careful l y handl ed duri ng t he det ergent manuf act ur i ng process (Fig. 8). It has good bi odegradabi l i t y (Fig. 9). We have al ready established t he t echni ques of manuf act ur i ng det ergent s compounded wi t h ~-SFMe synt hesi zed f r om pal m stearin. F U T U R E T R E N D S The devel opment of a process whi ch allows t he manuf act ur e o f hi gh-qual i t y a-SFMe has opened t he way f or a new way I O0 o 80 .~ 60 ~ 40 ~ 20 O ee" 0 o a- SFMe- Na ; zx AOS- Na ~, o " LAS- Na 3' ~ l I I I I 0 10 20 30 Days FIG. 9. Biodegradability of e-SFMe, AOS and LAS by residual organic car bon met hod (6). o f appl i cat i on o f pal m stearin t o det ergent , al t hough t he appl i cat i on o f pal m stearin t o soap is not a novel idea. At present salrfactants f or det ergent s such as LAS, AES, AS and AOS, are most l y dependent on pet rol eum-deri ved materials, while a part of f at t y al cohol is manuf act ur ed f r om coconut oil. Since t he oil crisis, however, nat ural fat s and oils have been expect ed t o gain mor e and mor e signifi- cance as industrial raw materials because t he y are renewabl e as compar ed wi t h pet rol eum-deri ved materials t hat are ex- pect ed t o be exhaust ed, and also because t hei r pr oduct i on is expect ed t o be subst ant i al l y increased by bi ot echnol ogy and agricultural t echnol ogy. As ~-SFMe is a surfact ant equal or superi or t o LAS, AES, AS or AOS, we believe t hat JAOCS, Vol . 62, no. 2 ( Febr uar y 1985) 335 SOAP AND RELATED PRODUCTS palm oil will compet e well with petroleum-derived materials and rank as one of the significant materials for detergents in the near future. REFERENCES 1. Junger mann, E., Bailey' s Industrial Oil and Fat Products, edi t ed byD. Swern, Vol. 1, 4t h ed., J ohn Wiley & Sons (1979) p: 534. 2. Ibid, p. 541. 3. Li on Corp. , Jpn. Pat ent 277, 606 (1951); Jpn. Pat ent 546, 648 (1969); U.S. Pat ent 4, 303, 590 (1981). 4. Smi t h, F.D., and A.J. St i rt on, JAOCS 44: 405 (1967). 5. Stein, W., and H. Baumann, JAOCS 52: 323 (1975). 6. Okumura, O., T. Sakat ani and I. Yamane, Vl l t h CID, Moscow (1976). 7. Schmid, K., H. Baumann, W. Stein and H. Dolhaine, Proceed- ings of 1st World Surfact ant s Congress, II, p. 105 (Mt i nchen 1984). 8. Lion Corp., U.S. Pat ent 3,839,391 (1974); U.S. Pat ent 3,925,441 (1974); U.S. Pat ent 4, 036, 596 (1977). 9. Lion Corp., U.S. Pat ent 3,997,575 (1976); U.S. Pat ent 4,404,143 (1983). 10. Kadoya, 1., and O. Okumura, Fragrance Jour nal 29: 61 (1978). Other Ol eochemi cal Uses: Palm Oil Products YOSHI TERU A K A I K E , Nippon Oil & Fats Co. , Ltd., Amagasaki Factory, Oil & Fats Research Lab. , 1-56 Ohama-cho, Amagasaki, Hyogo, 660 Japan ABSTRACT Product i on and consumpt i on of pal m oil and its pr oduct s are dis- cussed as t hey rel at e t o i ndust ri al pr oduct s The large volumes of palm oil bei ng produced and proj ect ed f or f ut ur e pr oduct i on shoul d increase t he use of i t s bypr oduct s in oleochemicals. Tallow is t he most compet i t i ve fat t o palm oil in t hese applications, but its mar ket share ( at least in Japan) seems t o be declining. An enzymat i c process for hydrol yzi ng fat s and oils by a solid phase process is described. I NTRODUCTI ON In t he near future, pal m oil is expect ed to be one of the largest fat and oil resources along with soybean oil. The main use of palm oil is in food products. Technologies such as fractionation, hydrogenation, and interesterification have made it possible to use more palm oil for these edible pur- poses. Industrial uses of palm oil could be learned based on those of tallow, whose f at t y acid composition is similar to t hat of palm oil. This presentation discusses mainly what kinds of palm oil products should be considered as the raw materials for industrial uses; what kinds of technological improvements will be expected for the development of industrial applications, and what are potential new uses. OUTLOOK FOR PALM OI L The high pot ent i al for palm oil is described in relation to: world fat and oil product i on; pal m oil product i on in Malaysia; vegetable oil product i on and f at t y acid composi- tion. World Fat and Oil Production Wor l d f a t a n d oi l p r o d u c t i o n ha s r e a c h e d 5 6 . 6 mi l l i o n t o n s with an increase of 16.7 million tons in the last ten years (Table I). In particular, the growth of vegetable oils for food was very remarkable, i.e., palm oil production was tripled, and soybean and rapeseed oils were doubled. Animal fat product i on showed less than 20% growth, but tallow and but t er product i on did increase. It is remarkable t hat the proport i on o f vegetable oils for edible uses in world fat and oil product i on increased from 61% to 69%. The growth of world fat and oil product i on in the past 10 years was due t o t he large harvests of palm, soybean and rapeseed oils. I t is assumed t hat this t endency will continue in the future. Palm Oil Production in Malaysia Palm oil production, which showed the largest growth c o mp a r e d wi t h o t h e r f a t a n d oi l r e s our c e s , ha s r e a c h e d 13% TABLEI W~ l dOH ~ d F ~ ~ o duc t i o n in 1970 ~ d 1 9 8 0 1970 1980 Decade (10,O00 met ri c t ons) growt h (%) Edible vegetable oils Soybean 608 1,222 201 Palm 172 506 294 Sunfl ower 380 478 126 Rapeseed 188 387 206 Coconut 214 326 152 Cot t onseed 262 321 123 Peanut 327 280 86 Olive 125 193 154 Ot hers 161 220 137 Subt ot al 2, 437 3,933 161 Industrial vegetable oils Linseed 111 64 Ot hers 64 63 Subt ot al 175 127 73 Marine animal oils Fish 104 117 Ot her s 21 7 Subt ot al 125 124 99 Ani mal fats Tallow and grease 435 604 139 Lard 413 383 93 Ot her s 411 493 120 Subt ot al 1, 259 1, 480 118 Tot al 3,996 5, 664 142 Source: U.S. Depar t ment of Agriculture. of world vegetable oil consumption for food in 1980, up f r om 7% in 1970. Palm oil production in Malaysia, having reached 3.5 million tons (60% of world production) in 1982, is expect ed to rise to 4 million tons in 1985, and to 6 million tons in 1990s (Table II). The big increase of palm oil in Malaysia is mainly dependent upon cultivation of idle land by FELDA, new hybri d seeds yielding bigger harvest and oil and pollination by the weevil. Malaysia export ed 3 million tons of palm oil and prod- ucts in 1982, 93% of which was palm oil product s (Table l i D. Th i s f i gur e wa s e q u i v a l e n t t o 85% o f t o t a l p r o d u c t i o n . Ta k i n g t h e s e i n t o a c c o u n t , t h e d e v e l o p me n t o f i n d u s t r i a l a p p l i c a t i o n s o f p a l m oi l a n d p r o d u c t s is g e t t i n g mo r e a n d mo r e i mp o r t a n t . JAOCS, Vol. 62, no. 2 (February 1985)
Journal of the American Oil Chemists' Society Volume 29 Issue 12 1952 [Doi 10.1007%2Fbf02631723] Daniel Swern; Winfred E. Parker -- Application of Urea Complexes in the Purification of Fatty Acids, Esters, And Alc