Isomerization during hydrogenation of soap: II. Potassium elaidate and potassium linoleate

Potassium elaidate in slightly alkaline solution was hydrogenated for up to 7 hr with 1.5% of Rufert nickel catalyst at 150 C and 20 kg/sq cm pressure. Potassium linoleate was similarly hydrogenated with 1.0% catalyst for 7 hr, and the hydrogenation continued for another 7 hr after addition of 0.5% fresh catalyst. Periodic samples from each were analyzed for component acids. The positional isomers in thecis andtrans monoenes, isolated by preparative argentation thin layer (TLC) or column chromatography, were estimated after oxidation to dicarboxylic acids. Some diene fractions were isolated for further examination. In potassium elaidate hydrogenation,cis monoenes were initially produced in considerable amounts, but to a lesser extent thereafter. Positional isomers were similarly distributed in bothcis andtrans monoenes after prolonged hydrogenation. In the hydrogenation of potassium linoleate, a drop in iodine value (IV) of 60 units occurred in the first hour, and 38% oftrans monoenes (in which the 10- and 11-monoenes constitute 32% each) were formed. The IV then fell only slowly, and up to 38% ofcis monoene (mostly 9- and 12-isomers) was formed. Addition of fresh catalyst caused a major shift ofcis monoenes totrans forms. The diene fraction was mostly nonconjugated material with the first double bond at the 9, 8 and 10-positions. Minor amounts of conjugated dienes were present as well as a dimeric product.     

Hydrogenation of soybean oil with copper catalysts containing small amounts of nickel catalysts

Reaction rates, linolenate/linoleate reaction selectivity,trans formation, and conjugated diene formation were determined for mixed commerical catalysts containing 0.5, 1, 2, 10, and 20 parts nickel catalyst (25% nickel) per 1000 parts copper chromite catalyst (ppt) and at catalyst concentrations in the oil of 1.0, 0.5, and 0.25%. The rate of hydrogenation increased as the amount of nickel increased. Addition of 0.5, 1, and 2 ppt nickel catalyst to copper chomite catalyst resulted in a small decrease in selectivity compared with straight copper chromite. When soybean oil was hydrogenated with these mixed catalysts sufficiently to reduce linolenate to 0, iodine values were 102–108 compared to 109–112 for straight copper chromite and to less than 80 for straight nickel. Presented at the AOCS Meeting, New Orleans April 1973. ARS, USDA.     

Isomerization during hydrogenation of soap. I. Potassium oleate

Potassium oleate in slightly alkaline solution was hydrogenated for up to 7 hr with Rufert nickel catalyst at 150C and 20 kg/sq cm pressure. With 1% catalyst, the iodine value dropped by 12 units in the first hour, and only slightly thereafter. With 2% catalyst there was a drop of 24 units in iodine value in the first hour, a steady state for the next 3 hr, and a second sharp drop of 30 units prior to the seventh hour. Samples of fat hydrogenated over 1% catalyst for 3 hr and 7 hr respectively were analyzed by gas-liquid chromatography, thecis andtrans monoenes were separated by argentation thin-layer chromatography, and the positional isomers in each were determined by oxidation of the total fraction to dicarboxylic acids, which were then estimated by GLC. Apart from double-bond saturation during the first 3 hr of hydrogenation, extensive double-bond migration yielded 23.5% oftrans 8- to 13-monoene, accompanied by small amounts only of positionalcis monoenes other than the starting material. After 7 hr of hydrogenation, extensivecis tocis isomerization occurs, accompanied by lesscis totrans shift; thecis:trans ratio for each monoene consequently tended toward 1:1. The results are explained on the sorption mechanism of hydrogenation and suggest that soap hydrogenation, involving catalyst poisoning, may represent a magnified version of normal fat hydrogenation.     

Selective hydrogenation of the cyclopropene acid groups in cottonseed oil

The cyclopropene acid groups in cottonseed oil can be modified by a light hydrogenation which will not produce large amounts oftrans isomers or lower the iodine value to a significant extent. Optimum conditions, as indicated by this investigation, are 105-115C, 20 psig hydrogen pressure, 0.1% electrolytic nickel as catalyst, and a low hydrogen-dispersion rate. Under milder conditions of hydrogenation the elimination of the cyclopropenes was accompanied by a lower formation oftrans isomers and a lower hydrogenation of noncyclopropenes, but the time required increased. In one hydrogenation carried out with commercial nickel catalyst, the 0.4% of malvalic acid groups in the cottonseed oil was hydrogenated completely whereas the iodine value was reduced by only 1.7 units and only 2.1% oftrans isomers was formed. AVinterization of cottonseed oils which had been hydrogenated to the point of eliminating their response to the Halphen test and in which only small amounts of saturated acid groups andtrans isomers had been formed gave yields equal to or better than those of the original oil. Hydrogénation actually increased the ease of winterization. 2 So. Utiliz. Ees. Dev. Div, ARS, USDA.     

Deuteration of methyl linoleate with nickel,palladium, platinum and copper-chromite catalysts

Samples taken during deuteration of methyl linoleate with the title catalysts were separated into saturate, monoene and diene fractions. Monoenes were further separated intocis andtrans fractions. A comparison of the double bond distribution in monoenes with those from hydrogenation of alkaliconjugated linoleate indicated that up to 59% of the linoleate was reduced through a conjugated intermediate with nickel catalyst. The respective percentages for palladium and platinum catalysts were 51 and 23. Copper catalysts have previously been shown to reduce linoleate solely through conjugated intermediates. Copper-chromite catalyst showed infinite selectivity for the reduction of linoleate, because stearate did not form. The decreasing order of various catalysts for the selective reduction was copper-chromite>>>Ni at 195 C>Pd>Ni at 100 C>Pt. Computer simulation of platinum reduction indicated that ca. 20% of the linoleate was directly reduced to stearate through a shunt. Geometrical isomers of linoleate were formed during reduction with all catalysts except copper-chromite. Nickel catalyst formed bothtrans,trans- andcis,trans-isomers, as well as nonconjugatable dienes. These isomers were favored at the higher temperature and deuterium was incorporated into them. Palladium and platinum did not isomerize linoleate to nonconjugatable dienes. Because conjugated dienes are more reactive than linoleate, they were not found in appreciable amounts during reduction. Conjugated dienes were the only isomers formed with copper-chromite catalyst. Deuterium was found in these conjugated dienes, which were also extensively isomerized. As a result of isomerization and exchange during reduction of linoleate-as well as further exchange between deuterium and monoenes-a wide distribution of isotopic isomers in monoenes was found with nickel, palladium and platinum catalysts. Since isomerization of monoenes with copper-chromite is negligible, the isotopic distribution of monoenes must be due to exchange of intermediate conjugated dienes followed by addition. Presented at the AOCS Meeting, Ottawa, September 1972. ARS, USDA.     

Competitive hydrogenation rates of isomeric methyl octadecadienoates

Determination of the relative reaction rates of isomeric methyl octadecadienoates is possible by competitive reduction of a mixture containing an inactive diene and a radioactively labeled isomer. The hydrogenation rate of methylcis-9,cis-12-octadecadienoate with platinum and nickel catalysts is compared to the hydrogenation rate of each of several isomers of methyl octadecadienoate, and the relative rate of the competitive hydrogenations is calculated by a digital computer. Methylcis-9,cis-12 linoleate is reduced the most rapidly of all the dienes studied. The relative rates of the positional isomers tend to decrease with the increasing number of methylene groups between the double bonds, except when one of the double bonds is in the more reactive 15 position. Comparison of the geometric isomers shows thattrans,trans diene is hydrogenated at a slower rate thancis,cis linoleate.

     

Hydrogenation of alkali-conjugated linoleate: Isomeric monoene profiles obtained with nickel,palladium and platinum catalysts

Alkali-conjugated linoleate (cis-9,trans-11- andtrans-10,cis-12-octadecadienoate) was hydrogenated with nickel, palladium and platinum catalysts. Thetrans andcis monoenes formed during reduction were isolated, and their double bond distribution was determined by reductive ozonolysis and gas liquid chromatography. About 44–69% of the monoenes were composed of δ¹⁰ and δ¹¹ trans monoene isomers, whereas the δ⁹ and δ¹² cis monoenes amounted to 20–26%. With nickel catalyst, composition of monoene isomers remained the same, even when the hydrogenation temperature was increased. The monoene isomer profiles between nickel and palladium catalysts were indistinguishable. Isomerization of monoenes with platinum catalyst was suppressed at 80 psi. The position of the double bonds in unreacted conjugated diene was always retained, except with nickel at both temperatures and with platinum at 150 C when a slight migration occurred. Geometrical isomerization totrans,trans-conjugated diene was observed in the unreacted diene with nickel (ca. 15% of diene) at both 100 C and 195 C, and with platinum (ca. 7% of diene) at 150 C. ARS, USDA.     

Alteration of long chain fatty acids of herring oil during hydrogenation on nickel catalyst

During hydrogenation of a refined herring(Clupea harengus) oil iodine value (IV) 119, on a commercial nickel catalyst, samples were collected at IV 108, 101, 88 and 79. In the early stages of the process, IV 119 to IV 101, the positional and geometrical isomerization of the long chain monoenoic fatty acids (20:1 and 22:1) was hindered by the stronger absorption on the catalyst surface of the polyenes with 4, 5 and 6 double bonds. Consequently at IV 101, 70% of these polyenes had been converted to dienoic and trienoic fatty acids, but only 3-4%trans 20:1 and 22:1 accumulated. As the hydrogenation proceeded, IV 101 to IV 79, the originaleis 20:1 and 22:1 isomers (mainly Δ11 with some ΔA9 and Δ13) decreased and new positional and geometrical isomers (both cis andtrans in positions Δ6 to Δ15) were formed. The majortrans isomers were Δ11 accompanied by important proportions of Δ10 and Δ12. At IV 79, moretrans 20:1 (ca. 36%) thantrans 22:1 (ca. 29%) was detected. Monoethylenic fatty acids newly formed from polyethylenic fatty acids made only minor contributions to the total 20:1 and 22:1 at these levels of hydrogenation, but a “memory effect” which skews the proportions of minorcis andtrans isomers can be attributed to the proportions of minorcis 22:1 isomers (Δ9, Δ13 and Δ15) orginally present. Presented in part at AOCS Annual Conference, San Francisco, May 1979.     

Positional and geometrical isomerization during partial hydrogenation of trilinolein: A comparison of copper and nickel catalysts

We have compared a nickel with a copper catalyst in the formation of some geometrical and positional isomers during the partial hydrogenation of trilinolein. The copper catalyst was found to produce fewer diene isomers than the nickel catalyst at a comparable iodine value. The copper catalyst produced more monoene isomers however, than did the nickel, particularlytrans monoenes. The distribution of the monoene isomers appeared to obey an equilibrium relationship with each other, independent of both iodine value and reaction conditions. We have presented additional evidence to postulate that copper catalysts hydrogenate polyenoic acids by first conjugating the acids. The selectivity of copper catalysts for triene over diene is probably due to the greater ease of conjugation of the triene.     

Hydrogenation of Vegetable Oils with Minimum trans and Saturated Fatty Acid Formation Over a New Generation of Pd-catalyst

Hydrogenation of sunflower and canola oils over a novel Pd-supported catalyst (pore size of 6.8 nm and BET specific surface area of 837 m²/g) was investigated and compared to commercial nickel catalyst. The formulated catalyst with Pd-loading of 1 wt%, supported on structured silica material was active and selective for the hydrogenation of sunflower and canola oils under mild process conditions. For both oils, the novel Pd supported catalyst exhibited a better selectivity than commercial Ni catalyst at a similar activity with a lower metal loading. For the same iodine value (IV) reduction, the Pd-catalyst produced less saturated fatty acids (SFA) and about the same level of trans fatty acids (TFA), but was more selective towards cis monoenes formation than Ni-catalyst. More importantly, this catalyst produced a reduced level of stearic acid, which at increased levels causes waxy mouth feel of the hydrogenated fat.     

The effect of conjugated linoleic acid isomers on fatty acid profiles of liver and adipose tissues and their conversion to isomers of 16:2 and 18:3 conjugated fatty acids in rats

Conjugated linoleic acid (CLA) is a collective term that describes different isomers of linoleic acid with conjugated double bonds. Although the main dietary isomer is 9cis,11trans-18∶2, which is present in dairy products and ruminant fat, the biological effects of CLA generally have been studied using mixtures in which the 9cis,11trans- and the 10trans,12cis-18∶2 were present at similar levels. In the present work, we have studied the impact of each isomer (9cis,11trans- and 10trans,12cis-18∶2) given separately in the diet of rats for 6 wk. The 10trans,12cis-18∶2 decreased the triacylglycerol content of the liver (−32%) and increased the 18∶0 content at the expense of 18∶1n−9, suggesting an alteration of the Δ9 desaturase activity, as was already demonstrated in vitro. This was not observed when the 9cis,11trans-18∶2 was given in the diet. Moreover, the 10trans,12cis-18∶2 induced an increase in the C₂₂ polyunsaturated fatty acids in the liver lipids. The 10trans,12cis-18∶2 was mainly metabolized into conjugated 16∶2 and 18∶3, which have been identified. The 9cis,11trans isomer was preferentially metabolized into a conjugated 20∶3 isomer. Thus, the 9cis,11trans- and the 10trans,12cis-CLA isomers are metabolized differently and have distinct effects on the metabolism of polyunsaturated fatty acids in rat liver while altering liver triglyceride levels differentially.     

Hydrogenation of a menhaden oil: I. Fatty acid and C20 monoethylenic isomer compositions as a function of the degree of hydrogenation

US menhaden oil is rich in long-chain polyethylenic fatty acids, chiefly C₂₀ (eicosapentaenoic) and C₂₂ (docosahexaenoic) fatty acids, unlike Canadian herring oil, which is rich in long-chain (C₂₀ and C₂₂) monoethylenic fatty acids. An examination of the product fatty acids from hydrogenation of menhaden oil therefore comple-ments studies previously published for herring oil. During a commer-cial hydrogenation of menhaden oil, iodine value (IV) 159.0, on nickel catalyst, samples were collected at IV 150.0, 140.0, 131.5, 120.5, 96.5, 90.0 and 84.5. The fatty acid compositions were deter-mined using a combination of mercuric adduct fractionation and gas liquid chromatographic (GLC) analyses, and the totaltrans content by infrared spectroscopy. The partial hydrogenation resulted in the disappearance of the pentaenoic and hexaenoic fatty acids, a de-crease in tetraenes, and a definite increase in trienes, 8.3% at IV 84.5 compared to 4.2% at IV 159.0. The dienoic fatty acids in-creased to 13.2% at IV 84.5 compared to 4.1% at IV 159.0, and the monoenoic fatty acids increased to 34.2% from 24.0%. No impor-tant changes in the saturated acids were observed, 43.8% at IV 84.5 compared to 41.6% at IV 159.0. The totaltrans content varied from 3.4% at IV 150.0 to 45.1% at an IV of 84.5. The isomer composi-tions of thecis andtrans C₂₀ monoethylenic fatty acids were deter-mined using a combination of preparative GLC, AgNO₃ thin layer chromatography and ozonolysis. Thecis 20:1 acids at IV 84.5 still retained 27.5% of the major isomer (All) originally present at 72%. The parent A5, A8, All, A14 and A17 bonds of the 20:5 originally present could be detected in thecis 20:1 isomers at IV 96.5 but not at IV 84.5. At IV 84.5, 58% of the 20:1was trans, the major isomer being All (9.4% of total 20.1), accompanied by important quanti-ties of Δ10 and Δ12, respectively, 6.9% and 6.6% of the total 20:1. Presented in part at the 73rd annual AOCS meeting, Toronto, 1982.     

High oleic oils by selective hydrogenation of soybean oil

High oleic (monoene) oils were obtained from soybean oil by selective hydrogenation with copper catalysts. A mixture of nickel and copper chromite catalyst had activity suitable for producing the high monoene oils. A new catalyst (copper-on-Cab-O-Sil) prepared in the Laboratory was more active than commercial copper catalysts. Hydrogenated oils contained 61–72% monoenoic and 14–24% dienoic acids, and there was essentially no increase in stearic acid. Thetrans-isomer content of these oils varied between 17% to 32%. Double bonds in the monoene were distributed along the molecule from C₆ to C₁₅, but were located preferentially in the C₉ position for thecis-monoene and in the C₁₀ and C₁₁ positions for thetrans-monoene. When the iodine value of these high monoene oils was about 90–95, they remained liquid above 28 C. Citric acid treatment reduced the copper content of hydrogenated oils to a level that was comparable to that of the original soybean oil. Presented at the AOCS Meeting, Chicago, October 1967. Food and Agricultural Organization representative from Rumania. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Hydrogenation ofcis-9,cis-12-,cis-9,trans-12- andtrans-9,trans-12- Octadecadienoates

The products formed by hydrogenation of methylcis-9,trans-12- andtrans-9,trans-12-octadecadienoates with nickel and platinum catalysts have been compared with those from methyl esters of the naturally occurring all-cis linoleate. Hydrogen uptake is slower for thetrans isomers. Much of the monoene consisted of esters with double bonds at the 9 and 12 positions with their original geometric configurations. Monoenoic esters with double bonds at the 10 and 11 positions were predominatelytrans and apparently formed by conjugation before hydrogenation. Nickel produced more isomerization than platinum but less than previously reported for copper. With both catalysts hydrogenation proceeded both directly and through conjugated intermediates, in contrast to copper in which all hydrogenation is believed to follow conjugation. Presented at the AOCS Meeting, Los Angeles, April 1972. ARS, USDA.     

Incorporation oftrans long-chain n−3 polyunsaturated fatty acids in rat brain structures and retina

During heat treatment, polyunsaturated fatty acids and specifically 18∶3n−3 can undergo geometrical isomerization. In rat tissues, 18∶3 Δ9c, 12c, 15t, one of thetrans isomers of linolenic acid, can be desaturated and elongated to givetrans isomers of eicosapentaenoic and docosahexaenoic acids. The present study was undertaken to determine whether such compounds are incorporated into brain structures that are rich in n−3 long-chain polyunsaturated fatty acids. Two fractions enriched intrans isomers of α-linolenic acid were prepared and fed to female adult rats during gestation and lactation. The pups were killed at weaning. Synaptosomes, brain microvessees and retina were shown to contain the highest levels (about 0.5% of total fatty acids) of thetrans isomer of docosahexaenoic acid (22∶6 Δ4c, 7c, 10c, 13c, 16c, 19t). This compound was also observed in myelin and sciatic nerve, but to a lesser extent (0.1% of total fatty acids). However, the ratios of 22∶6trans to 22∶6cis were similar in all the tissues studied. When the diet was deficient in α-linolenic acid, the incorporation oftrans isomers was apparently doubled. However, comparison of the ratios oftrans 18∶3n−3 tocis 18∶3n−3 in the diet revealed that thecis n−3 fatty acids were more easily desaturated and elongated to 22∶6n−3 than the correspondingtrans n−3 fatty acids. An increase in 22∶5n−6 was thus observed, as has previously been described in n−3 fatty acid deficiency. These results encourage further studies to determine whether or not incorporations of suchtrans isomers into tissues may have physiological implications. Presented in part at the 32nd International Conference on the Biochemistry of Lipids, 1991, Granada, Spain. Delta nomenclature (Δ) is used fortrans polyunsaturated fatty acids to specify the position and geometry of ethylenic bonds. Polyunsaturated fatty acids containingtrans double bonds are abbreviated giving the locations of thetrans double bonds only; e.g., 20∶5 Δ17t 20∶5 Δ5c,8c,11c,14c,17t; 22∶5 Δ19t, 22∶5 Δ7c,10c,13c,16c,19t; 22∶6 Δ19t 22∶6 Δ4c,7c,10c,13c,16c,19t.     

Catalytic hydrogenation of linoleic acid on nickel,copper, and palladium

The catalytic activity and selectivity for hydrogenation of linoleic acid were studied on Ni, Cu, and Pd catalysts. A detailed analysis of the reaction product was performed by a gas-liquid chromatograph, equipped with a capillary column, and Fourier transform-infrared spectroscopy. Geometrical and positional isomerization of linoleic acid occurred during hydrogenation, and many kinds of linoleic acid isomers (trans-9,trans-12; trans-8,cis-12 orcis-9,trans-13; cis-9,trans-12; trans-9,cis-12 andcis-9,cis-12 18∶2) were contained in the reaction products. The monoenoic acids in the partial hydrogenation products contained eight kinds of isomers and showed different isomer distributions on Ni, Cu, and Pd catalysts, respectively. The positional isomers of monoenoic acid were produced by double-bond migration during hydrogenation. On Ni and Pd catalysts, the yield ofcis-12 andtrans-12 monoenoic acids was larger than that ofcis-9 andtrans-9 monoenoic acids. On the contrary, the yield ofcis-9 andtrans-9 monoenoic acids was larger than that ofcis-12 andtrans-12 monoenoic acids on Cu catalyst. From these results, it is concluded that the double bond closer to the methyl group (Δ12) and that to the carboxyl group (Δ9) show different reactivity for hydrogenation on Ni, Cu, and Pd catalysts. Monoenoic acid formation was more selective on Cu catalyst than on Ni and Pd catalysts.     

Hydrogenation of methyl oleate in solvents

The hydrogenation of the oleic acid group was investigated with the objective of determining the effect of solvents on the reaction rate and the formation of positional and geometrical isomers. Methyl oleate, either alone or dissolved in one of several solvents, hexane, ethanol,n-butyl ether, or acetic acid, was hydrogenated to an iodine value of about 50 under atmospheric pressure and at 30°C, with palladium-on-carbon and the W-5 form of Raney nickel as catalysts. Hydrogenation with palladium catalyst, with or without solvents, produced 76.6 to 79.1%trans bonds, based on the total double bonds. This is significantly greater than the 67% obtained previously. Hydrogenation products obtained with Raney nickel and solvents contained as little as 20.7%trans bonds at an iodine value of about 50. In two cases thetrans bonds were equal to about one-third the positional isomers. Positional isomers formed extensively when the Raney nickel was used in the absence of solvents and when the palladium catalyst was used. When the Raney nickel and solvents were used large proportions of double bonds were found in the original 9-position. Presented at the 51st Annual Meeting of the American Oil Chemists’ Society, Dallas, Tex., April 4–6, 1960. One of the laboratories of the Southern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture.     

Hydrogenation of fatty oils with palladium catalysts. V. Products of the tall oil industry

Conditions were found for reducing tall oil distillate to an iodine number of 22 with a sufficiently small amount of palladium catalyst to make the process commereially feasible. The operating conditions were 200°C and 2,600 psi. Tall oil fatty acids were reduced with palladium and the concentration of linoleic acid,cis-oleic acid, saturated acid, andtrans isomers were determined as a function of iodine number. The five-platinum group metals (Pt, Pd, Ir, Rh, Ru) were compared as to activity, selectivity of partial hydrogenation, and tendeney to formtrans-isomers.     

New synthesis ofcis-3,cis-5- andtrans-3,cis-5-tetradecadienoic acids,pheromone constituents ofattagenus elongatulus andA. megatoma

A new method for the synthesis ofcis-3,cis-5- andtrans-3,cis-5-tetradecadienoic acids, pheromone constituents of the dermestid beetlesAttagenus elongatulus andA. megatoma, was developed. The syntheses are based upon the formation oftrans-2-tetradecen-5-ynoic acid by reaction of 4-bromo-2-butenoic acid with 1-decynylmagnesium bromide. The enynoic acid undergoes alkali-induced isomerization to yield a mixture of acids from whichcis-3- andtrans-3-tetradecen-5-ynoic acids were separated in 31% and 34% yields, respectively. Methyltrans-2-tetradecen-5-ynoate was similarly prepared and isomerized to furnish methylcis-3-tetradecen-5-ynoate in 8% yield. Reduction of the tetradecenynoic acids with dicyclohexylborane gavecis-3,cis-5-andtrans-3,cis-5-tetradecadienoic acids in 4% and 39% yields, respectively. A better yield (49%) in the reduction ofcis-3-tetradecen-5-ynoic acid tocis-3,cis-5-tetradecadienoic acid was obtained by hydrogenation over Lindlar's catalyst. Similarly, reduction of methylcis-3-tetradecen-5-ynoate with disiamylborane gave 22% methylcis-3,cis-5-tetradecadienoate.     

Continuous slurry hydrogenation of soybean oil with nickel catalysts

Soybean oil was hydrogenated continuously in the presence of nickel catalysts. The iodine value of the products was varied by changing the oil flow rate and temperature of the reaction. Sulfur-promoted nickel catalyst increased the selectivity for linolenate hydrogenation, but formed much higher proportions oftrans isomers. Linoleate selectivity improved with temperature with both nickel and sulfur-promoted nickel catalysts, buttrans isomerization also increased. The feasibility of this continuous reactor system was demonstrated as a practical means to prepare hydrogenated stocks of desired composition and physical characteristics at high throughput.