US3459776A - Process for the production of metal soaps of epoxydized fatty acids - Google Patents

Process for the production of metal soaps of epoxydized fatty acids Download PDF

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US3459776A
US3459776A US356473A US3459776DA US3459776A US 3459776 A US3459776 A US 3459776A US 356473 A US356473 A US 356473A US 3459776D A US3459776D A US 3459776DA US 3459776 A US3459776 A US 3459776A
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epoxy
epoxydized
acid
fatty acids
water
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Alfred Szczepanek
Margarete Szczepanek
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Hoesch Chemie GmbH
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Hoesch Chemie GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals

Definitions

  • the present invention is concerned with the process for the production of metal soaps of epoxidized fatty acids.
  • Metal soaps of epoxidized fatty acids have frequently been proposed for the heat and light stabilizing of halogen-containing synthetic resins.
  • metal soaps of saturated and unsaturated fatty acids can be produced by the following processess;
  • the saponication of the epoxy fatty acids which are not liquid at room temperature, for example, epoxy stearic acid, with sodium hydroxide in an aqueous medium is incomplete, even with vigorous dispersion and long reaction time, so that the end products are contaminated, after the precipitation, with large amounts of epoxy fatty acid. Furthermore, large amounts of alkali metal soaps are entrained during the precipitation which can only be removed from the reaction product with great diiiiculty.
  • the epoxy fatty acids which are liquid or semi-liquid at room temperature, for example, diepoxy-stearic acid, can admittedly be easily saponied at room temperature in an aqueous medium with alkalis in the same manner as their starting substance, linoleic acid, but, nevertheless, the epoxy metal soaps obtained after the precipitation are considerably contaminated with the alkali metal soaps.
  • the unreacted free epoxy fatty acid there results from the amount of alkali metal hydroxide equivalent hereto by the precipitation with the metal salts, metal hydroxides which, as a result of the their insolubility cannot subsequently be removed by washing and lead to a clouding of the transparent polyvinyl chloride.
  • alkali metal soaps have an undesired effect by increasing the take up of water, together with an increase of the conductivity and cloudiness.
  • the object of the present invention is a process of good reproducibility, in which, while preserving the epoxy group, the production of metal soaps of epoxy fatty acids is possible, said soaps being substantially free from start ing materials and intermediate products.
  • the metal soaps of epoxydized fatty acids are obtained by the double reaction of their alkali metal or ammonium salts with-soluble metal salts.
  • An important factor for the preservation of the epoxy group is the maintenance of a low reaction temperature and a short saponication time for the conversion of the epoxy fatty acids or their esters into the alkali metal or ammonium soaps.
  • alkali metal soaps are produced by the reaction of epoxidized fatty acids or their esters or glycerides with an aqueous alcoholic solution of alkali metal hydroxides, the alkali metal soaps thus produced then being reacted in a second step with a water-soluble metal salt.
  • the reaction takes place according to the following equation:
  • the saponiiication of fatty acids with alkali metal hydroxides is, in general, carried out at a temperature above the melting point of the acid and in a concentration which is determined by the solubility of the alkali metal soap. in this case, one uses temperatures which are as high as possible and which are dependent upon the melting point of the metal soaps produced, in order to limit the amount of water necessary and in order to increase the throughput rate per reaction vessel.
  • reaction media there are used organic solvents miscible with water, in the form of solutions thereof with water.
  • the preferred organic solvents are alcohols.
  • the invention comprises contacting epoxidized fatty acid in an aqueous, organic liquid, alkaline medium with a monovalent cation for saponiiication to form salt of the epoxidized fatty acid and the cation, and thereafter contacting the salt with an aqueous solution of a water-soluble salt of the polyvalent metal to be produced, to thereby form the polyvalent metal soap product.
  • an aqueous, organic liquid medium for the rst step wherein the saponification is performed is preferred.
  • FIG. l is a graph of time in hours versus the percentage of epoxy groups in the product, with the percent organic liquid as parameter, the organic liquid being ethanol;
  • FIG. 2 is a graph of time versus acid number with a parameter as is the case in FIG. l, and also for ethanol as the organic liquid.
  • the graph of FIG. l shows the decrease of the epoxyoxygen in dependence on time, with the alcoholic content of the solution used as parameter.
  • Decrease in oxygen of the epoxy group is light in alcoholic solutions of up to about 50% (that is, is slight for the curves for 10%, 30% and 50%), but rises sharply in the case of 70% alcohol and more concentrated alcoholic solutions in the desired operating times of 2-4 hours.
  • the graph of FIG. 2 shows the increase in acid number in dependence on time, the strength of the aqueous alcoholic solutions being again ⁇ shown as parameter.
  • a high acid number shows that the saponitication proceeds rapidly in the desired time.
  • an alcoholic concentration of at least about 50% is preferred.
  • the dependence of the variables involved is generally true for the process of the invention for the acid ⁇ and esters as starting materials.
  • FIG. 2 shows dependence of the variables when the starting material is the ester.
  • the concentration of organic liquid is percent of organic liquid based on the organic liquid and water.
  • the organic solvents used must be at least partially water-soluble and possess a good dissolving power not only for the epoxidized compounds serving as starting materials but also for their alkali metal soaps.
  • the most suitable solvents are the aliphatic Cl-C., branched and straight chain alcohols. Ethanol is preferred.
  • the ratio waterzalcohol is dependent not only upon the nature of the alcohol, but also of the reaction components.
  • the organic liquid content of the medium for the rst step can -be about -70% organic liquid, for example 10-70% alcohol.
  • ester and also the use of acid, as starting material
  • a high content of organic liquid can be used, and as the temperature is increased, the content of alcohol or other organic should be decreased.
  • an organic liquid content for example an alcohol content, and in particular an ethanol content, of 50-70% is preferred, whereas at 50 the said content is preferably -50%.
  • high organic liquid content is used ⁇ at high temperature, the destruction of epoxy groups becomes faster than the saponication.
  • the organic liquid content of the medium is an important factor in realization of suitable saponication rates and suitable retention of epoxy groups. In some cases, production of the product desired will not be realized in the absence of the selection of appropriate organic liquid concentration-temperature relationship.
  • the reaction temperature for the saponication can be between room temperature and about 60 C.
  • the alcohol content of the medium should correspond to the saponification temperature to provide retention of epoxy groups at least equal to that obtained for the saponication at a temperature of 50 C. and an alcohol content of 30%.
  • the saponification of the epoxy fatty acid ester is an equilibrium reaction, depending upon temperature and time, in which the saponication and ring opening of the epoxy group proceed simultaneously.
  • the saponication velocity of the ester is considerably higher than the ring opening velocity of the epoxy group.
  • the reaction time is dependent upon the nature of the ester and the ratio or water to alcohol.
  • the saponiiication time amounts to about 0.5 hour and for esters of polybasic alcohols to 2 to 4 hours. In general reaction time is about 0.5-4 hours.
  • the ratio of water to alcohol is, as already mentioned, dependent upon the nature of the ester, of the alcohol and of the solubility of the alkali metal soap formed in the saponication mixture. Furthermore, in the case of certain metal soaps, the degree of polymerization is also influenced.
  • the dependence of the polymerization of the metal soaps upon the ratio of alcohol to water is particularly noticeable in the case of the saponification of the zinc soaps from epoxidized linseed fatty acid.
  • These soaps can be produced in aqueous alcoholic solution with an ethanol content of more than 50% without difficulty but, in the case of an alcohol content below 50%, products are obtained which, in the case of the epoxy oxygen determination, can no longer be decomposed with hydrochloric acid ether.
  • the alcohol or other organic liquid content of the aqueous solution amounts to l0-70%, preferably 50- 70%, or better 50-60%, and is so chosen that the alkali metal soaps formed are clearly soluble.
  • a good range or organic liquid, eg. alcohol, concentration is about 10-60%.
  • the lowest limit of the alcohol content of the saponication mixture amounts to 10% in the case of the epoxidation products of poly-unsaturated acids.
  • the metal soaps of epoxy fatty acids produced according to this process contain small amounts of starting esters which, according to the intended use, are either washed out with organic solvents or, for example, for use as polyvinyl chloride stabilizers, are not disturbing since the epoxydized esters of fatty acids are valuable plasticizers.
  • the alkaline material used to provide the desired alkaline conditions can be any suitable alkaline material.
  • alkali metal hydroxides one can also use alkali metal oxides, metallic oxides or hydroxides which form soluble epoxy metal soaps in the reaction mixture, or ammonium hydroxide or its derivatives.
  • acids the alkali metal alcoholates can be used.
  • saponication it is preferred to use the oxides, hydroxides and alcoholates, of Group I of the Periodic System, ammonium hydroxides and its derivatives.
  • Esters with monoor polybasic alcohols can be converted in the saponitication to metal soaps.
  • the esters can be produced by the trans-esterilication of unsaturated nat- -urally occurring oils and, if desired, purified by fractional distillation. Glycerides, glycol derivatives, etc. can be ernployed.
  • the ester is an ester of a monobasic alcohol
  • the alcohol can be a lower alkanol having about l- 4 carbon atoms.
  • the alcohol however, can be a higher alcohol.
  • the aliphatic alcohols can provide the alcohol moiety of the ester.
  • epoxy values of epoxydized fatty acids decreases very rapidly upon storage, presumably because the presence of the carboxylic acid group opens the epoxy ring.
  • the technical application of epoxydized fatty acids is thereby rendered diiiicult.
  • esters renders possible the production of metallic soaps of epoXy-ricinolic acid while avoiding the technically diflicult isolation and puriiicaton of the ricinolic acid.
  • Epoxydized fatty acids and their esters as starting materials in the sense of the present invention are the prod-
  • the usually powdery products are filtered olf, freed from the alkali metal salts formed during the reaction by washing with water and carefully dried at temperatures of -60 C.
  • the metal can be a metal of Group II-IV, particularly the following metals: sodium, lithium, magnesium, aluminum lead, calcium, barium, cadmium, zinc and manganese.
  • the metal content epoxy oxygen value, melting point and f-ree fatty acid were determined.
  • the determination of the characterizing data generally known methods are used, apart from the determination of the epoxy oxygen content of the epoxy metal soaps.
  • This value cannot be determined directly.
  • the metal soap is decomposed, down to the complete decomposition of the soap', at lower temperatures in the presence of ether with 2 N hydrochloric acid.
  • the ethereal solution is subsequently washed with water, dried over anhydrous sodium sulphate and distilled off at a low temperature.
  • the epoxy oxygen value is then determined by the known method on the isolated epoxy fatty acid. Control tests with epoxyand diepoxy-stearic acid show that the test conditions used for the decomposition of the epoxy metal soaps only lead to a negligible reduction of the epoxy oxygen content of the epoxy fatty acid so that this indirect method for the determination of the epoxy oxygen content of the epoxy metal soaps gives a substantially correct value.
  • Epoxydized soyabean oil 150 5.9 10.
  • 4 182 Epoxydized castor oil 52 3. 9 2 3 180 C20-C22 acid mixture 197 3. 8-5. 0 3-5 155-180 Epoxydized methyl ester of C20-C2i acid mixture 190 4. 4-5. 5 3-5 150-170 Epoxydized olive oil 95 4. 2 1 1 184 Epoxydized liuseed oil 190 7.0-7.5 1-2 3.1 186 ucts produced by known processes, preferably from naturally occurring unsaturated fatty acids or their esters. They contain the by-products formed by the opening of the ring of the epoxy group in the epoxydation but the use of pure starting material is also possible in principal.
  • the fatty acid or the fatty acid moiety can contain about 11-22 carbon atoms.
  • Preferred starting materials are epoxydized undecylenic acid, oleic acid, linoleic acid and linolenic acid, either alone or in admixture with one another or with saturated fatty acids, as well as the esters of monoor polybasic alcohols, such as methanol and glycol, obtained therefrom, and the glycerides of these acids.
  • epoxydized fatty acids fatty acids containing oxirane rings. There can be one or more than one epoxy group present.
  • a further advantage of the saponiiication with aqueous alcoholic alkali metal hydroxide solutions is that the crude products obtained after the epoxydation of unsat- -urated fatty acids and of their esters can be converted into the metal soaps via the alkali metal soaps without working up.
  • the reaction of the alkali metal soaps to the metal soaps takes place by the addition of an aqueous solution of the corresponding metallic salt at room temperature.
  • the impurities or by-products contained in these technical products iniiuence the physical constants of the metallic soaps produced therefrom but are, however, of no significance for the preferred technical use as polyvinyl chloride stabilizers.
  • the products produced according to the invention consist mainly of the metal soaps of the following acids: l0,llepoxyundecanic acid, 9,10-epoxystea'ric acid, 9,l0,l2,l3diepoxystearic acid, ⁇ 9,l0,l5,l6 diepoxy-A-lZ, l 3-stearic acid, ⁇ 9, l0, l2, 13, 15, l6triepoxy stearic acid and the epoxydation products of polyunsaturated C20-C22 fatty acids obtained from fish oils.
  • i c a Type C Appearance Metal Type C. Appearance 15 l Calcium di 85-100 White, easily plastic Barium di 120-141 Yellowisli powder. powder. Calcium di 97-105 Yellowish, easily plastic Cadmium di 152-155 D0.
  • Zinc 105-115 Light yellowish, plastic Magnesium di (J8-115 VOlllmlDGllS Whlte 20 Aluminum mono (l) White powder.
  • Metal TYP C Appeaame Aluminum 1.0110 0 i POW elf: Ceiciuni di tic-e5 white powder.
  • epoxydized linseed fatty acid or epoxydized castor oil are readily adhering powders which are somewhat yellowish in color and have a melting range between 150-200 C.
  • the solubility of the sodium and potassium epoxy soaps in water increases, by equal chain length, with the increasing number of epoxy groups.
  • the possibility of producing the lithium soaps of epoxy fatty acids is shown in the following, based on the example of the epoxydized methyl ester of oleic acid, from which can be produced lithium epoxy stearate using lithium hydroxide in water-alcohol mixture. It is a white crystalline powder with a melting point of over 200 C.
  • the partially considerably water-soluble magnesium soaps of the epoxy fatty acids are obtained, by double reaction of their alkali metal soaps with magnesium chloride, as white powders or white to yellowish plastic masses with a melting range of 70-120" C. Their tendency to polymerize with loss of the epoxy oxygen content is considerable, the crystalline magnesium epoxy soaps going over into a plastic state.
  • the calcium soaps of the epoxy fatty acids are white, crystalline to yellowish readily plastic powders with a melting range of 85-120 C. Their water solubility, with the exception of calcium soap of epoxy linseed fatty acid, is slight, as is also their tendency to polymerize with the splitting off of the epoxy group.
  • the barium soaps of the epoxydized fatty acids are white crystalline to yellowish, readily plastic, frequently very water soluble substances with a melting range between 100 and 160 C. The tendency of the epoxy group to polymerize is slight.
  • the cadmium soaps of the epoxydized fatty acids are white crystalline to yellowish readily plastic powders with a melting range between 100 and 180 C. Their water solubility is, in general, slight, as is their tendency to polymerize with the reduction of the epoxy oxygen content.
  • the zinc soaps of the epoxydized fatty acids are white crystalline to yellowish plastic products with a melting range between 100 and 120 C. Their water solubility is slight and the tendency to polymerize exists only in the case of epoxydized castor oil.
  • the manganese soaps of the epoxydized fatty acids are pink to red-brown colored crystalline to plastic products with a melting range of between 80 and 130 C. Their tendency to polymerize is light.
  • the mono, diand tri-aluminum soaps of epoxylized fatty acids can be produced by the reaction of the alkali metal soaps with aluminum sulphate. They are white to pale yellow somewhat sticky powders, whose lower epoxy oxygen content indicates a splitting o of the epoxy group either by polymerization or by the acidic reaction of the aluminum sulphate solution.
  • Normal and basic lead epoxy soaps can be produced by the double reaction of the alkali metal soaps with lead acetate. They are white-yellowish crystalline to plastic products which have a strong tendency to polymerize with loss of the epoxy oxygen content.
  • Example 2 Dialuminum soap of epoxydized oleic acid 62.4 g. epoxydized oleic acid (Ep02 2.8%) are dissolved in 300 ml. 96% ethanol and 12 g. sodium hydroxide in 240 ml. water added at room temperature. One stirs for half an hour at room temperature until the solution has become clear, adds, with stirring, 33.9 g. aluminum sulphate octadecahydrate in 200 ml. water, adds a further 300 ml. water thereto and subsequently stirs for a further hour. After filtration and washing, the product is dried at 60 C. Yield 70 g., aluminum 4.84%, melting range 70200 C., epoxy oxygen of the isolated acid 0.53%.
  • Example 3 -Dibasic lead soap from epoxydized oleic acid 31.2 g. epoxydized oleic acid (EpO2 2.92%) are dissolved in 300 ml. 96% ethanol and 12 g. sodium hydroxide in 240i ml. water added thereto at room temperature. One stirs for half an hour at room temperature until the solution has become clear and adds thereto, with stirring, 58 g. lead acetate trihydrate in 300 ml. water, adds a further 300- ml. water thereto and subsequently stirs for a further hour. After ltering and washing, the product is dried at 60 C. Yield 47 g. lead 44.9%, melting point 70-102" C., epoxy oxygen of the isolated acid 2.98%.
  • Example 7 Magnesium soap of epoxydized soybean oil 32.2 g. apoxydized soybean oil (epoxy oxygen 5.2%) are dissolved in ml. 96% ethanol and 4 g. sodium hydroxide dissolved in 80 ml. water added with stirring at room temperature. One stirs for about half an hour until the solution has become clear and adds thereto 10.4 g. magnesium chloride dissolved in Water. After dilution to three times the volume with water, one stirs for two hours and filters 01T. The product is dried at 50 C. Yield 27 g., magnesium 3.1%, epoxy oxygen of the isolated acid 5.6% melting point 66-102 C.
  • Example 10 -Calcium soap of epoxydized methyl ester of C20-C22 acid mixture
  • 30 g. epoxydized methyl ester of C20-C22 acid mixture (EpO2 4.7%) are dissolved in 124 ml. 96% ethanol and 3.3 g. sodium hydroxide in v66 ml. Water added thereto, with stirring, at room temperature.
  • Example 11-Calcium soap of epoxidized olive oil 29.8 g. epoxydized olive oil (EpOz 4.0%) are dissolved in a mixture of 10() ml. 96% ethanol and 55 ml. butanol and 4 g. sodium hydroxide in 80 ml. water added thereto at room temperature with stirring.
  • 10() ml. 96% ethanol and 55 ml. butanol and 4 g. sodium hydroxide in 80 ml. water added thereto at room temperature with stirring.
  • One warms to 30 C. and continues stirring for up to half an hour until a clear solution is obtained 6.2 g. calcium chloride (91%) dissolved in 300 ml. water are then added, with stirring.
  • After dilution with three times the volume of Water one stirs for two hours, filters oft the product, washes and dries at 50 C. Yield 30.5 g., calcium 4.6%, melting point 90-95 C., epoxy oxygen of the isolated acid, 3.6%.
  • Example 12 -Zinc soap of epoxidized linseed oil 28.6 g. epoxydized linseed oil (EP02 6.5%) dissolved in 150 ml. ethanol and 4 g. sodium hydroxide dissolved in ml. water added thereto with stirring. One stirs for half an hour at room temperature and then adds 14.65 g. zinc sulphate dissolved in 300 ml. Water. The product is filtered off, washed and dried at 50 C. Yield 28 g., zinc 9.8%, melting point 62-90 C., epoxy oxygen of the osolated acid 6.3%.
  • coholic, alkaline medium with a monovalent metal cation for saponication to form the salt of the epoxidized fatty acid and said cation said medium being a solvent for the epoxidized fatty acid and said salt, and containing about l0-70% alcohol based on the alcohol and water present therein, and
  • said medium containing an alkaline material selected from the group consisting of alkali metal oxides, alkali metal hydroxides and alkaline ammonium compounds, said alkaline material rendering the medium alkaline and providing said monovalent cation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Epoxy Compounds (AREA)
  • Fats And Perfumes (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US356473A 1960-06-03 1964-04-01 Process for the production of metal soaps of epoxydized fatty acids Expired - Lifetime US3459776A (en)

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DE1960C0021597 DE1225160C2 (de) 1960-06-03 1960-06-03 Verfahren zur herstellung von metallseifen epoxydierter fettsaeuren
DEC0034634 1960-06-03

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1313453C (zh) * 2004-10-08 2007-05-02 广东联塑科技实业有限公司 环氧不饱和高级脂肪酸复合锌皂的制备方法
RU2497817C1 (ru) * 2012-07-19 2013-11-10 Валерий Валентинович Темников Способ получения солей эпоксидированных карбоновых кислот
US20180077899A1 (en) * 2016-09-22 2018-03-22 Empire Technology Development Llc Methods and Compositions for Dag Mitigation

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PH18130A (en) * 1980-02-07 1985-03-22 Unilever Nv Process for the manufacture of soap

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2684353A (en) * 1951-05-31 1954-07-20 Buffalo Electro Chem Co Method of stabilizing halogen containing polymeric substances against heat and lightwith salts of epoxy fatty acids
GB754584A (en) * 1954-05-17 1956-08-08 Fmc Corp Method of stabilizing halogen containing polymeric substances against heat and light with salts of epoxy fatty acids
GB825691A (en) * 1956-12-03 1959-12-23 Union Carbide Corp Improvements in the preparation of salts of epoxy-fatty acids

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2684353A (en) * 1951-05-31 1954-07-20 Buffalo Electro Chem Co Method of stabilizing halogen containing polymeric substances against heat and lightwith salts of epoxy fatty acids
GB754584A (en) * 1954-05-17 1956-08-08 Fmc Corp Method of stabilizing halogen containing polymeric substances against heat and light with salts of epoxy fatty acids
GB825691A (en) * 1956-12-03 1959-12-23 Union Carbide Corp Improvements in the preparation of salts of epoxy-fatty acids

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1313453C (zh) * 2004-10-08 2007-05-02 广东联塑科技实业有限公司 环氧不饱和高级脂肪酸复合锌皂的制备方法
RU2497817C1 (ru) * 2012-07-19 2013-11-10 Валерий Валентинович Темников Способ получения солей эпоксидированных карбоновых кислот
US20180077899A1 (en) * 2016-09-22 2018-03-22 Empire Technology Development Llc Methods and Compositions for Dag Mitigation

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NL140520B (nl) 1973-12-17
CH413810A (de) 1966-05-31
GB985218A (en) 1965-03-03
GB985219A (en) 1965-03-03
DE1443679A1 (de) 1969-06-26
GB985217A (en) 1965-03-03

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