US3687989A - Process for the selective hydrogenation of fats and fatty acids - Google Patents

Process for the selective hydrogenation of fats and fatty acids Download PDF

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Publication number
US3687989A
US3687989A US828383A US3687989DA US3687989A US 3687989 A US3687989 A US 3687989A US 828383 A US828383 A US 828383A US 3687989D A US3687989D A US 3687989DA US 3687989 A US3687989 A US 3687989A
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fatty acid
fatty acids
process according
catalyst
hydrogenation
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Josef Baltes
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • B01J27/04—Sulfides
    • B01J27/047—Sulfides with chromium, molybdenum, tungsten or polonium
    • B01J27/049—Sulfides with chromium, molybdenum, tungsten or polonium with iron group metals or platinum group metals

Definitions

  • ABSTRACT Fats and fatty acids containing diene, triene or polyene fatty acid residues or containing cis monoene residues are hardened or decolorized by hydrogenating them in the presence of a nickel sub sulfide alone or together with molybdenum and/or tungsten sulfides to form a product having a substantial amount of trans monoene residues.
  • This invention relates to the hardening and decolorizing of fats (including animal and vegetable oils) and fatty acids by selective hydrogenation. It is known that certain properties of unsaturated fatty acids and their derivatives can be altered by removing a double bond by reaction with hydrogen or by re-arrangement of a double bond structure, with respect either to the steric configuration or the position of a double bond or bonds in the carbon chain of the fatty acid molecule.
  • the first reaction is known as hydrogenation, while the second reaction is tenned isomerization.
  • monoene will be used to denote both monoethenoid fatty acids and also polyethenoid fatty acids in which the double bonds form neither a conjugated nor an allyl structure; fatty acids with two conjugated double bonds or a single allyl configuration (as defined above) will be referred to as dienes; compounds having three double bonds in a conjugated or allyl configuration will be referred to as trienes.
  • Molecules having more than three double bonds either in a conjugated configuration or in an allyl configuration will be referred to as polyenes.
  • the selectivity of the partial hardening depends on the different rates at which different unsaturated fatty acid residues are hydrogenated, and also on the stepwise course followed by the reaction. Trienes and polyenes show the highest reaction speeds, compounds with diene and monoene groups reacting noticeably more slowly. Under the usual conditions the selective hardening takes place stepwise; for example triene groups are first converted to dienes,zthese are then converted to monoenes and the latter are finally converted to saturated groups. According to the simplified reaction scheme trienes K dienes I K, monoenes K saturated products the ratio of the velocity constants can be employed as a measure of the selectivity and can'be calculated from the composition of the particular starting product and hardened products. In addition to the hardening conditions (temperature, hydrogen pressure and stirring) the nature of the catalyst has a significant influence on the degree of selectivity. Theselectivity of nickel catalysts is not high,'butusually suffices for the requirements set in the manufacture of edible fats.
  • nickel catalysts when used for the hardening of fats, are particularly'sensitive towards contact poisons, and in the presence of such poisons the course of the reaction is significantly interfered with and the hardened products have properties whichdeviate from standard and are undesired.
  • the presence of sulfur compounds is particularly feared, since these can under certain circumstances completely inhibit the hydrogenation reaction.
  • the raw materials intended for hardening are purified asv highly as possible (by treatment with caustic alkali and F ullers earth, washing and drying) in order to remove the contact poisons mentioned and especially sulfur.
  • fats and fatty acids can be selectively hydrogenated with the aid of nickel subsulfide along or with tunsten sulfide and/or molybdenum sulfide, in such a way that the diene, triene and polyene fatty acid residues are almost completely converted to monoene fatty acid residues of trans-configuration, and that monoene fatty acid residues of cis-configuration originally present undergo a spatial rearrangement to the corresponding transcompounds.
  • Selenides or tellurides of the corresponding transition metals can also be used but do not offer any advantages in respect of selectivity and are more difficult to manufacture.
  • the invention comprises a process for the selective hydrogenation of fats and fatty acids in the presence nickel subsulfide as a catalyst.
  • the catalysts can be used on supports if desired.
  • the sulfides are preferably employed in amounts of 0.05 to parts per 100 parts of fat or fatty acid. (Parts are by weight). It is advantageous to work at a temperature between 100 and 250 C., and using a hydrogen pressure of l to 50 kg/cm.
  • Suitable sulfides are, molybdenum disulfide, molybdenum pentasulfide, molybdenum sesquisulfide, molybdenum tetrasulfide, molybdenum trisulfide, nickel monosulfide, nickel subsulfide, tungsten disulfide, tungsten trisulfide.
  • a nickel sub sulfide catalyst for use according to the invention can advantageously be made by mixing an aqueous solution of a nickel salt with a support, such as 'y-aluminum oxide, rendering the mixture weakly alkaline with ammonia, and passing the stoichiometric amount of hydrogen sulfide into the mixture at ordinary or a slightly elevated temperature, whereupon nickel is deposited on the support as the sulfide. After filtration, copious washing, drying and grinding, the material is treated with hydrogen at elevated temperature (for example at 200 C.) and at ordinary or elevated pressure to convert the nickel-sulfur compound completely into Ni S which is then ready to be used as the catalyst.
  • elevated temperature for example at 200 C.
  • the hydrogen treatment can take place in the presence of the material which is to be hydrogenated (as in Examples 2 and 7).
  • Another known method that can be used is to precipitate nickel hydroxide or nickel carbonate from a nickel salt solution, and to convert this, after filtering off and drying, into the sulfide (Ni S by means of hydrogen sulfide or sulfur at elevated temperature.
  • nickel sulfide is obtained in the form of a paste which after treatment with hydrogen is also well suited for use as the catalyst.
  • catalysts and mixed catalysts within the scope of the invention can be made in essentially the same way.
  • the weight ratio of transition metal to sulfur generally corresponds to that of the particular known sulfides (for example Ni S M08; or W8).
  • a particular advantage of the catalysts to be used according to the invention is that they are practically completely insensitive towards contact poisons such as can occur in fats and fatty acids, and that they therefore possess an almost unlimited working life and can be used repeatedly. As a result, less effort can be expended on purifying the fats to be hardened; in general mechanical clarification (filtration with filtration aids), washing and drying suffices.
  • Hardening using the catalysts of the invention, can be effected under the usual conditions, in discontinuous or continuous operations. Below C. the hydrogenation takes place very slowly, while temperatures above 250 C. are not necessary and should be avoided in view of possible thermal modification of the starting material. In the case of fats the most favorable temperature range is 180 to 210 C. and in the case of fatty acids 200 to 220 C.
  • the hydrogen pressure can vary within fairly wide limits. Below 1 kg/cm the reaction speed is low, while pressures above 50 kg/cm are not necessary and would therefore be uneconomical.
  • the most advantageous pressure range is usually between 2 and 25 kglcm
  • the hydrogenation up to the final stage that is to say up to the complete conversion of the polyene fatty acids residues into monoene residues, can be completed in a few hours, the precise time depending on the temperature, hydrogen pressure, and catalyst concentration.
  • Fats and fatty acids generally which contain unsatu rated constituents can be treated by the process of the invention, particularly vegetable oils such as soya bean oil, sunflower oil, groundnut oil, rape oil, cottonseed oil, corn oil, oiticica oil, tung oil, perilla oil, grapefruit seed oil, hempseed oil, orangeseed oil, peanut oil, poppyseed oil, safflower oil, sesame seed oil, and the like, and oil from marine animals such as fish oil and whale oil, of which the unsaturated fatty acid residues are known to possess a cis-configuration and which, to the extent that they contain more than one ethylenic group (i.e. are polyethenoid), possess allyl structures.
  • vegetable oils such as soya bean oil, sunflower oil, groundnut oil, rape oil, cottonseed oil, corn oil, oiticica oil, tung oil, perilla oil, grapefruit seed oil, hempseed oil, orangeseed oil, peanut oil, poppys
  • the oils there can be used the corresponding mixtures of the free fatty acids or pure fatty acids such as linoleic acid or linolenic acid.
  • the hardened products obtained have an unusual composition in comparison to the known hardened fats, and as a result possess some novel advantageous properties which are of importance for their use. This is based on the fact that fatty acid residues in which the ethylenic groups have an allyl structure, are hydrogenated to monoene fatty acid residues, but the latter are not at all, or only to a very insignificant extent, converted to saturated fatty acid residues.
  • the fats which have been hardened in accordance with the invention are distinguished by high stability towards oxidative influences and have hardly any ten- 5 dency to become rancid either on storage or during use. For this reason they are particularly suitable for baking and deep frying. Their melt behavior over the approximate temperatures range to 40 C., as can be deduced from dilatation measurements, shows their excellent suitability for use as substitutes for cocoa butter, for example for the manufacture of icing fats.
  • the hardened products can also be employed in other cases where solid fats are usually required, for example in the manufacture of margarine.
  • the hardened fatty acids are mixtures of transmonoene fatty acids and saturated fatty acids, having a content of saturated fatty acid determined by that of the starting material.
  • Technical fatty acids of this nature thus for the first time become accessible in a simple manner.
  • Relative to the comparable solid technical fatty acids, which consist practically completely of saturated fatty acids (palmitic acid, stearic acid and higher acids) they are distinguished by their differing melting behavior (lower melting point and solidification point), while their stability in use and on storage of H.P. Kaufmann, F. Volbert and G.
  • EXAMPLE 1 p 1.5 kg. of de-acidified and bleached soya bean oil (containing 0.06 percent of free fatty acids calculated as oleic acid) and 25 g. of a supported catalyst consisting of 1 part of nickel sulfide (Ni s and 2 parts of 7- aluminum oxide, were introduced into anautoclave of 3 liters capacity fitted with an electromagnetic stirrer and the usual attachments. Thus, 0.55 parts of nickel sulfide (Ni S were used per 100 parts of soya bean oil. After displacingthe air by hydrogen the system was heated to 200 C.
  • Ni S nickel sulfide
  • the hydrogenation of the color- 0 132-8 liquid C10 105 0.5 ing constituents takes place preferentially, and this is $3 Cm particularly noticeable in the case of crude palm oil, 45 glB- 0 the red color of which disappears completely after a is: brief period of hydrogenation (up to half an hour), 1% 103.5 26.0 0,, 10.5 though the fat hardening process only just starts 5 3 noticeably in this stage.
  • the invention includes the 1; discoloring of fats and fatty acids without or with con- 50 88.2 32.0 com1tantharden1ng.
  • the total fatty acids consisted of: 10.0% of palmitic acid 8.0% of stearic acid 73.0% octadecaene-acid 8.5% of octadecadiene-acid 0.5% of octadecatriene-acid.
  • the poly-unsaturated fatty acids of this hardened product did not show any allyl structure, that is to say their double bonds were separated from one another by more than one methylene group.
  • EXAMPLE 2 An autoclave equipped with an electromagnetic stirrer and the usual fittings was charged with 2 kg. of washed, dried and filtered soya bean oil (0.45 percent free fatty acid) and 100 g. of nickel sulfide (NiS) which had been freshly precipitated with exclusion of air and dried, and was flushed with hydrogen and heated to 200 C., after starting the stirrer. During the heating-up period hydrogen was injected up to a pressure of 20 kg/cm and a stream of about 3 liters of hydrogen per minute was then established by means of the appropriate inlet and outlet valves, keeping the pressure in the autoclave constant. Reduction of the sulfide started at once, as shown by the formation of hydrogen sulfide.
  • NiS nickel sulfide
  • the total fatty acids consisted of 6.8% of palmitic acid 8.2% of stearic acid 1.5% of arachidic acid 79.0% of octadecaene-acid 4.5% of octadecadiene-acid.
  • EXAMPLE 3 1.5 kg. of de-acidified and dried herring oil (0.06 percent free fatty acid, iodine number 141) were hardened for 5 hours with 30 g. of a nickel sulfide supported catalyst according to Example 1, at 4-5 kg/cm hydrogen pressure, and otherwise under the same conditions as in Example 1.
  • the hardened product had the following properties and characteristics:
  • EXAMPLE 4 1.5 kg. of de-acidified and dried Peruvian fish oil (0.06 percent free fatty acid, iodine number 197) were hardened with 30 g. of a commercially available mixed supported catalyst containing 8 percent by weight of nickel sulfide (Ni s and 10 percent by weight of molybdenum sulfide (MoS deposited on 'y-aluminum oxide, in the same way as in Example 1. The initially high speed of hydrogen uptake fell off appreciably after 3 hours, and after a further hour the hydrogenation was stopped.
  • Ni s and 10 percent by weight of molybdenum sulfide MoS deposited on 'y-aluminum oxide
  • the liquid part of the hardened product was separated off by means of a pressure filter, leaving about 1 kg. of solid residue.
  • the constituent which is liquid at ordinary temperature had an iodine number of 105, and the solid residue an iodine number of 87.0 and a capillary melting point of 34.8 C.
  • EXAMPLE 1.5 kg. of commercial distilled soya oil fatty acid were hydrogenated with 45 g. of the supported catalyst specified in Example 1 for 5 hours at 210 C., and 20 kg/cm hydrogen pressure.
  • the properties and characteristics of the starting material and the hardened product are compared below.
  • EXAMPLE 6 1.5 kg. of crude palm oil (2.3 percent of free fatty acid) were treated with hydrogen with the aid of 30 g. of a mixed supported catalyst consisting of 10 parts of nickel sulfide (M 8 and parts of tungsten sulfide (WS on 75 parts of kieselguhr, at 180 C., and 6 kg/cm pressure, under conditions otherwise identical to those of Example 1. The course of the hardening can be seen from the comparison of the properties and characteristics of the starting oil and hardened products, given below.
  • the color of the oil is already considerably lighter after a hydrogenation time of 15 minutes and corresponds to that of an oil which has been heat-bleached in the usual manner, before any significant hardening of the oil has occurred.
  • a process for the hardening or decolorizing of a fat or fatty acid containing diene, triene or polyene fatty acid residues or containing cis-monoene residues comprising subjective said fat or fatty acid to hydrogenation conditions in the presence of a catalyst selected from the group consisting of nickel subsulfide and mixtures of nickel subsulfide with at least one of tungsten sulfide and molybdenum sulfide whereby the gie e, trien or polyene re s'dues re selectivel y rogenate to monoene resi ues an almost all 0 the cis-monoene residues present in the starting material or formed during the hydrogenation reaction are isomerized to trans-monoene residues.
  • a process according to claim 3 wherein the hydrogenation is carried out at 100 C. to 250 C. at a hydrogen pressure of l to 50 kg/cm.
  • the catalyst consists of nickel sulfide Ni S 6.
  • the catalyst is a mixture of nickel subsulfide with a member of the group consisting of molybdenum sulfide and tungsten sulfide, the catalyst is used in an amount of 0.05 to 10 parts by weight per 100 parts by weight of fat or fatty acid and the hydrogenation is carried out at 100 C. to 250 C. at a hydrogen pressure of 1 to 50 kg/cm*.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US828383A 1968-06-04 1969-05-27 Process for the selective hydrogenation of fats and fatty acids Expired - Lifetime US3687989A (en)

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Application Number Priority Date Filing Date Title
DE1767675A DE1767675C2 (de) 1968-06-04 1968-06-04 Verfahren zur selektiven Härtung und trans-lsomerisierung von Fetten und Fettsäuren

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US (1) US3687989A (ja)
JP (1) JPS5231363B1 (ja)
AT (1) AT319445B (ja)
BE (1) BE733800A (ja)
CH (1) CH511936A (ja)
DE (1) DE1767675C2 (ja)
DK (1) DK133115C (ja)
FR (1) FR2011012B1 (ja)
GB (1) GB1213116A (ja)
NL (1) NL157649B (ja)
NO (1) NO129303C (ja)
SE (1) SE339277B (ja)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3856831A (en) * 1973-07-12 1974-12-24 Fuji Oil Co Ltd Process for preparing hard butter
US4163750A (en) * 1976-02-11 1979-08-07 Johnson, Matthey & Co., Limited Process for the hydrogenation of a vegetable oil
US5064670A (en) * 1990-04-06 1991-11-12 The Procter & Gamble Company Low-saturate frying fat and method of frying food
US5215779A (en) * 1990-01-04 1993-06-01 The Procter & Gamble Company Low-saturate, all purpose plastic shortening with specially hydrogenated intermediate-melting fat component
US5852208A (en) * 1996-08-30 1998-12-22 Dixie Chemical Company, Inc. Method of producing compounds containing acyloxyalkoxy groups from alcohols
US20040146626A1 (en) * 2003-01-28 2004-07-29 Higgins Neil W. Low trans-stereoisomer shortening systems
WO2019132407A1 (ko) 2017-12-29 2019-07-04 한화케미칼 주식회사 수소화 반응용 촉매 및 이의 제조방법

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4799727B2 (ja) * 2000-10-31 2011-10-26 花王株式会社 オレイン酸の製法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB415203A (en) * 1933-04-12 1934-08-23 Ig Farbenindustrie Ag Improvements in the hydrogenation of fats and fatty oils
US2674634A (en) * 1950-08-05 1954-04-06 Shell Dev Hydrogenation of polyunsaturated compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3123626A (en) * 1964-03-03 Fatty oils
DE615148C (de) * 1932-12-24 1935-06-28 I G Farbenindustrie Akt Ges Verfahren zur katalytischen Hydrierung von Fetten und fetten OElen

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB415203A (en) * 1933-04-12 1934-08-23 Ig Farbenindustrie Ag Improvements in the hydrogenation of fats and fatty oils
US2674634A (en) * 1950-08-05 1954-04-06 Shell Dev Hydrogenation of polyunsaturated compounds

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Dierichs et al. Hydrogenation of Crude Montan Wax Chem. Abst. Vol. 55 (1961) 16980e *
German Pat. 801395 Aluminum catalysts Especially for the Treatment of Hydrocarbon Oils, Chem. Abst. Vol. 45 (1951) 2192b *
Kirkpatrick Nickel Sulfide Catalysts Advances in Catalysis, Volume II, 1951 *
Tyutyunnikov et al. Sulfur Containing Nickel as a Catalyst in Hydrogenation of Fat Izv. Vyssh. Ucheb. Zaved., Pisbeb. Tekhnol. 1968(6), 38 41. Chem Abst. vol. 70 (1969) 59132t *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3856831A (en) * 1973-07-12 1974-12-24 Fuji Oil Co Ltd Process for preparing hard butter
US4163750A (en) * 1976-02-11 1979-08-07 Johnson, Matthey & Co., Limited Process for the hydrogenation of a vegetable oil
US5215779A (en) * 1990-01-04 1993-06-01 The Procter & Gamble Company Low-saturate, all purpose plastic shortening with specially hydrogenated intermediate-melting fat component
US5064670A (en) * 1990-04-06 1991-11-12 The Procter & Gamble Company Low-saturate frying fat and method of frying food
US5852208A (en) * 1996-08-30 1998-12-22 Dixie Chemical Company, Inc. Method of producing compounds containing acyloxyalkoxy groups from alcohols
US20040146626A1 (en) * 2003-01-28 2004-07-29 Higgins Neil W. Low trans-stereoisomer shortening systems
US7169430B2 (en) 2003-01-28 2007-01-30 Bunge Oils, Inc. Low trans-stereoisomer shortening systems
US20070172573A1 (en) * 2003-01-28 2007-07-26 Higgins Neil W Low trans-stereoisomer shortening system
US7718211B2 (en) 2003-01-28 2010-05-18 Bunge Oils, Inc. Low trans-stereoisomer shortening system
WO2019132407A1 (ko) 2017-12-29 2019-07-04 한화케미칼 주식회사 수소화 반응용 촉매 및 이의 제조방법
KR20190081127A (ko) 2017-12-29 2019-07-09 한화케미칼 주식회사 수소화 반응용 촉매 및 이의 제조방법
US11987659B2 (en) 2017-12-29 2024-05-21 Hanwha Solutions Corporation Hydrogenation reaction catalyst and preparation method therefor

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Publication number Publication date
NO129303C (ja) 1975-12-30
DE1767675B1 (de) 1970-05-14
CH511936A (de) 1971-08-31
FR2011012A1 (ja) 1970-02-27
DK133115B (da) 1976-03-22
SE339277B (ja) 1971-10-04
NO129303B (ja) 1974-03-25
GB1213116A (en) 1970-11-18
BE733800A (ja) 1969-12-01
NL6908072A (ja) 1969-12-08
NL157649B (nl) 1978-08-15
DK133115C (da) 1976-08-23
SU363236A3 (ja) 1972-12-30
FR2011012B1 (ja) 1975-04-18
JPS5231363B1 (ja) 1977-08-15
DE1767675C2 (de) 1975-11-20
AT319445B (de) 1974-12-27

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