73
`
`meEs (FATS AND RELATED sunsram‘cas)
`
`an increase in the number of carbon atoms in the molecule. The change
`
`in physical state is aCcompanied by a decrease in solubility. Stearie
`acid, which melts at TOCC., is practically insoluble in water.
`The fatty acids up to and including caprie are etsily removed from
`solutions by distillation with steam and hence are known as volatile fatty
`acids. The determination of the volatile fatty acids is a matter of con—
`siderable importance in the analysis of fats, as it aids in distinguishing
`one type of fat from another. Butter fat, for example, gves a higher
`proportion of Volatile acids than any other fat or oil.
`The volatile fatty acids likewise have a decided odor. Butyric acid
`has a strong odor similar to that of rancid hutter. Caproie, eanrylic,
`and caprie acids have a pronounced animal odor and are sometimes spoken
`of as the goat. acids. When fats become rancid, a small amount. of these
`volatile fatty acids is formed and gives to the fats a particularly objec-
`tionable odor and taste. Thus the objectionable odor of rancid butter
`is due largely to the presence of free butyric acid.
`
`Unsaturated fatty acids
`
`If a fatty acid contains a pair of carbon atoms that are joined together
`by two bonds instead of one, that is, a double bend,
`it
`is said to be
`unsaturated.
`Such an acid can take up hydrogen, iodine, bromine, oxy-
`gen, or other elements by the breaking open of one of these two bonds.
`This leaves an open position on each carbon atom. Therefore, for each
`double bond, two hydrogcns can combine with the compound, which would
`then be regarded as a saturated compound. This condition of unsatura-
`tion has a unique relation to the physical state of the fatty acid and
`likewise to the glyccrides of the fatty acid. For example, oleie acid
`[Cl1I133COOII), which contains one double bond, and therefore two
`fewer hydrogcns than stearic acid,
`is a liquid, whereas stearic acid
`(CquaC‘OOHHs a solid. Oleie acid melts at. 14°, whereas stearic acid
`melts at 70“.
`If the fatty acid contains more than one double bond,
`it will have a correspondingly lower melting point;
`linoleie acid, which
`contains two double bonds, has a melting point of —18°.
`The physical state of the fatty acids is carried over to the glycerides
`of these acids. Oleie acid and olein are liquids, and stearic acid and
`stearin are solids. Linolein and linolenin, as expected, are liquid glycer-
`ides. Since fats are mixtures of glycerides, a fat will be soft or hard
`depending upon the proportion of
`liquid glycerides it contains. Oils
`differ from fats in that. they contain a larger proportion of liquid glycer~
`ides. As a general statement, it might be said that oils contain about
`80 per cent of unsaturated glyccridcs, whereas solid fats do not contain
`more than 40 to 50 per cent. Unsaturation is a fundamental property
`and, in most fats, is the key to the whole question of their physical state.
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 78
`
`Petitioner Microsoft Corporation — EX. 1032, p. 78
`
`

`

`unions (sun‘s AM) unmrnn sunsramzns)
`
`79
`
`If this is kept in mind, an undeistanlling.r of many physical and chemical
`properties of fats is easily acquired.
`isomeric forms.
`in different
`Unsaturated acids have. the ability to exist
`which are called geometric. isomers. These. are. designated by the prefixes
`cis- and trans-. This type of isomcrism, a conseqln-nee of the presence
`of carbon—to-earhon double bonds, may be. illustrated by the. formulas of
`oleic acid and its trans-isomer, elaidic acid:
`
`II(|‘|J(CH;};CII;
`IIC(CII:);CO0H
`Oleic acid
`
`(sis-isomer)
`
`H;C(CH:);C”IH
`IICtCHoEOOl—l
`Elaidic acid
`
`_
`
`(trans-isomer)
`
`in four geometric
`Acids like linoleie with tWo double bonds can exist
`isomers, corresponding to the. iris-trans arrangement about each; in general,
`the number of ismners possible is {2}", where a is the number of double
`bonds present. Generally the natural fatty acids occur in the cis form,
`although vaccenic appears to he a trans acid. Where {mas forms do not
`occur naturally, they may readily be produced by treating the. cis acids
`with nitrous acid or certain other reagents. This reaction has come.
`to be spoken of as “elaidinization” from the circumstance that oleic acid
`is
`thus partially converted into elairlic. The trans acids are higher
`melting and less soluble than the corresponding cis forms.
`The most important unsaturated fatty acids, together with their for-
`mulas and occurrence, are listed in Table 4—4. Many other acids with
`varying numbers of carbon atoms and different degrees of unsaturation
`have been reportedly obtained from brain, liver, and other tissues. The
`chemistry of these acids and their function in the animal organism are
`not yet clearly defined. Their presence in some of the most important
`organs of the body leaves little room for doubt
`that their role is an
`important one.
`Although it is- rather well established that the animal body can dc-
`saturate fats, certain limitations to this process apparently exist
`in
`many, if not all, species. Rats kept on diets devoid of unsaturated fats
`develop a scaliness of the skin,
`lesions in the kidneys. sterility, and
`loss of "weight, and eventually die. This nutritionai deficiency can he
`prevented by including either linoleie or arachidonic acid in the diet.
`These particular unsaturated fatty acids have therefore come to he
`called “essential fatty acids.” Xo one has demonstrated a need of the
`human body for these acids, but even though they may be required, their
`widespread occurrence in foodstuffs renders any disease in man resulting
`from their deficiency quite unlikely.
`Quantitative Relations of the Fatty Acids. Many of the statements
`made in the preceding pages regarding the. fatty acids become more
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 79
`
`Petitioner Microsoft Corporation — EX. 1032, p. 79
`
`

`

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`Petitioner Microsoft Corporation — EX. 1032, p. 80
`
`
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`Petitioner Microsoft Corporation - Ex. 1032, p. 80
`
`

`

`LnanEs (FATS AND RELATED suasr-mcns)
`
`81
`
`clear if a study is made of their tplautitative distribution. The com-
`position of the mixture of fatty acids obtained by hydrolysis of some
`common fats and oils is given in Table 11—5.
`they yield such a large
`Butter-fat and coconut oil are. unique in that
`number of fatty acids, many of which are lou'er members of the saturated
`fatty acid series. Kote the small number of fatty acids obtained from
`lard and the large percentage of unsaturated acids given by the oils.
`
`Nonsaponifinbfe nmuer
`
`In addition to glycerol and fatty acids, natural fats contain another
`type of material called nonsaponifiahle matter or “nousap.” This is
`customarily separated after saponitieation by extracting the alkaline
`soap solution with ether. The “nonsap” left after evaporation of the
`ether consists of
`fat-soluble pigments, sterols. vitamins, antioxidants,
`and other miscellaneous substances. Although the nonsaponifiable com-
`ponents constitute only a small part (1—2 per cent] of most natural fats,
`they are often of great importance in relation to the flavor, color, keeping
`qualities, and nutritional value of the fat.
`
`GLYCERIDES 0F COMMON FATS
`
`Although the percentages of different fatty acids given by hydrolysis
`of natural fats are fairly accurately known, much less information exists
`as to the I'iarticular glycerides from which these fatty acids are obtained.
`lly crystallizing the fats from acetone and other solvents, a partial separa-
`tion of the individual glycerides in a number of fats has been made. The
`separation is a long and laborious procedure, and in no sense complete.
`All the data accumulated show that the number of glycerides is very
`great and that they are more complex than was previously supposed.
`Since glycerol, C;:,H,—,(OH]3, contains three hydroxyl groups,
`it. can be
`ester-ified with one, two, or three molecules of acid to give monoglyccrides,
`diglycerides, and triglycerides, respectively.
`It is this last type which
`is found in fats.
`.The three acid radicals in a triglyceride may be all
`alike, in which case the substance is called a simple glyceridc;
`if more
`than one kind of radical is present, the cmnpound is called a attired glycer-
`i'de. The glycerides are named according to the fatty acids involved in
`their formation.
`
`Thus the ester formed from glycerol and three molecules of palmitic
`acid is called tripalmitin, or simplyr pahnitin.
`Its structural formula is
`written below. Other typical simple glyceridcs are trioiein, tristearin,
`and tributyrin:
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 81
`
`Petitioner Microsoft Corporation — EX. 1032, p. 81
`
`

`

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`Petitioner Microsoft Corporation - Ex. 1032, p. 82
`
`.55
`
`82
`
`Petitioner Microsoft Corporation — EX. 1032, p. 82
`
`

`

`LIPIDI-JS (Li-err;
`
`.m'n RELATED sr’nancns)
`
`“3
`
`0 l
`
`l
`11 ;C()C (CI 1 0:01 I =CII (C112),CH3
`
`ll
`HCOCKJHQ);CII=C‘II(CH1);CII;
`
`l r
`
`IIgCOCLCHa);(TlI=CIl (CH1) :CII;
`Triolein
`
`ll
`}12COC(CII))1CII3
`
`
`
`ll
`IICOC£CII=):CH,
`
`| 0ll
`
`H1C0C(CII,} 2CH;
`Tributyrin
`
`0
`H2C0g(CH3) “CH;
`
`9
`HCO(I31[CH2)“CH;
`O
`IIgCOCHI(CH3) “CH;
`Tripalmit'm
`
`O
`H,CO(l"l(CH,) ”CH;
`O
`HCOg(CH2)15CH-a
`l 0
`H1C0g(CH:)”CHa
`Tri5tearin
`
`The ester formed from glycerol emnbinerl with two molecules of stearie
`arid and one of palmitie acid is eulletl (listenro-palmitin. This is a typical
`mixed glyceride. Another is o]eo-stearo-palmitin:
`
`0
`H,COg[CIl;)1CH=CH(CHz} :CH:
`I o
`HCOg(CH2} ”CH;
`O
`chog(CII-1)|‘CHJ
`Olco-stearo—palmitin
`
`0 l
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`l
`H1COC(CH3)15CH;
`
`0 l
`
`
`
`l
`HCOC£CHa)1aCH';
`
`ll
`H:COC(CH :) ”CH:
`Distearo—palmitin
`
`More eonrlenserl fm'mulus are. :llr‘n frequently written. Thus, for example,
`the oleie. aeill raclieal
`luleyl ratliral) may be abbreviated from
`
`0 l
`
`l
`t0 —CC1;H;;
`
`0 I
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`I
`hC(CH2)TCII2CII(C£12)ICII3
`
`and triulein may be written
`
`‘1?
`caflsloccnnuh
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 83
`
`Petitioner Microsoft Corporation — EX. 1032, p. 83
`
`

`

`84
`
`LIPIDES (FATS AND RELATED SUBSTANCES)
`
`However, the more detailed structural formulas should be used by the
`beginning student until familiarity with them has been gained.
`It
`is
`evident
`that a great many different
`individual glycerides might be
`formed by suitably combining glycerol with the various fatty acids.
`It
`has been calculated that ten fatty acids can produce 550 possible com-
`binations.
`
`Formerly it was customary to regard the natural fate as consisting
`chiefly of simple glycerides, but more recent work shows that they eon-
`sist largely of mixed glycerides.
`It is impossible to say with certainty
`just how much of any given fatty acid goes to make up simple or mixed
`glycerides in a fat.
`In the ease of butyric acid, it is known that the
`acid does not exist as a simple glyccride in butter, but is present in a
`mixed combination. Tributyrin is a bitter substance; obviously, it cannot
`be present in butter.
`It is probably more nearly correct to say that
`natural fats consist essentially of mixtures of mixed glycerides.
`
`PHYSICAL PROPERTIES OF FATS
`
`As already explained, fats may be either solids or liquids at room tem-
`pcraturc (20°C.). The common animal fats arc solids at this tempera-
`ture, and the majority of “vegetable fats (oils) are liquids. Fats and
`oils are lighter than water and, as a rule. have a specific gravity of about.
`0.8. As usually seen they are noncrystatlinc, although many fats can
`be made to crystallize under suitable conditions.
`{See Fig. 4—1.) They
`are poor conductors of heat, therefore serving a useful purpose in the
`insulation of the body.
`Fats are colorless when they are obtained in a pure state. The more
`or less yellow color common to many fats is due to the presence of a
`pigment, and not to the fat itself. Butt-er, for example, varies in color
`with the season.
`In June, when cows feed on grass, the butter is highly
`colored, while in January, when the animals receive a dry ration, the
`butter is paler in color. The yellow pigment, therefore,
`is contained in
`the feed of the animals. This is largely carotene, (3401-156, which occurs
`in all green plants, in the petals of many flowers, such as the narcissus,
`and in many vegetables sueh as carrots, squash, etc.
`In grass it is not
`evident because the green pigment, chlorophyll, masks the carotene.
`Xanthophyll, CwI‘Ingg, is another yellow pigment which is widely dis-
`tributed in plant materials. This is the chief coloring pigment found
`in egg yolk.
`It is also contained in butterfat, but in a much smaller
`percentage than is carotene. The egg yolk likewise varies in color with
`the feed of the poultry. Lard contains no coloring matter, probably
`because swine are fed on rations largely free from green material.
`The coloring of fats, which is of importance commercially, has been
`brought into considerable prominence in connection with the vitamin A
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 84
`
`Petitioner Microsoft Corporation — EX. 1032, p. 84
`
`

`

`Lll’lllI-ZS (FA‘I‘b‘ AND ltEI..—\‘I‘F.D suoslumcrzs)
`
`8:":
`
`In 1919 Stt-enbuek called attention to the occurrence
`content of food.
`of vitamin A in close association with the yellow pigmentation of fats
`and foods: for example, yellow corn was found to be rich in vitamin A.
`while white corn was deficient
`in this. vitamin. The same correlation
`
`between vitamin and pigment was found with mama to carrots, squash,
`
`
`
`From Hawk and Bergelm. Practice! Physiological f'liPlliinl‘y.
`(fourtvsy of 1’. Blakls'ton's lion 8: (‘11.. Im'.
`
`Fig. 4—1. Crystals of beef fat.
`
`cabbage, and other vegetables. The work of von Euler, Moore, and
`others has demonstrated that carotene of plants is the precurSor of
`vitamin A in the animal body. Carotene is transformed in the body,
`apparently in the liver, from an intensely yellow pigment into an almost
`colorless compound. This transformation is accompanied by changes in
`structure and other properties of the pigment
`(see p. 207).
`In the pure state, fats have no taste, but by a curious anomaly natural.
`fats are the chief materials that give flavor to food. Food prepared with-
`out. the addition of fat is considered by many people unpalatable; liberal
`additions of butter make food particularl)r appetizing. Butter owes its
`taste largely to diaeetvl
`(CH3 CO CO CH“) and aeety[methyl—carbine]
`[CH3 CO CIlOII CHa), compounds produced by bacteria in the ripen-
`ing of the cream.
`The same condition obtains with respect to odor. When purified, fats
`have no odor: yet natural fats frequently have marked odors. This
`apparent contradiction is explained by the readiness with which
`ats
`take up odors. The housewife carefully avoids putting onions and
`butter together in the refrigerator. The absorption of odors by fats is
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 85
`
`Petitioner Microsoft Corporation — EX. 1032, p. 85
`
`

`

`86
`
`LIPIDES (FATS AND RELATED SUBSTANCES)
`
`used to advantage in the extraction of delicate perfumes from flowers.
`Rese petals are spread on glass plates covered with a thin layer of lard
`and tallow and left
`in contact with the fat for 24‘72 hours. At the
`end of this time the 01d flowers are removed and a new lot
`is added.
`
`to remove the essence,
`is extracted with cold alcohol
`Finally the fat
`and the alcoholic solution is concentrated or bottled directly. This proc-
`ess yields perfumes of the finest quality.
`The substances that often are present in natural fats and, as explained
`above, impart to them characteristic colors, flavors, and odors are not
`chemically related to the fats themselves, but are merely associated
`with them on account of being “fat-soluble," that is, easily soluble in
`fat. Thus carotene is a fat—soluble pigment. When the cream is churned
`nearly all of
`the carotene remains in the butter rather than in the
`buttermilk, which of course is largely an aqueous medium. Substances
`that are fat-soluble are usualiy insoluble in water, and vice versa.
`
`CHEMICAL PROPERTIES OF FATS
`
`Hydrolysis and snponificalion
`
`The most important chemical reaction of fats is hydrolysis, with the
`production of glycerol and fatty acids. This process may be brought
`about by means of acids, superheated steam, or enzymes. The fat-
`splitting enzymes are known as lipases. They occur in many tissues of
`the body and in plant material, especially in oily seeds. A well known
`fat-splitting enzyme is steepsin, which is secreted by the pancreas and
`is involved in the digestion of fats. Many bacteria, molds, and other
`microorganisms produce fat-splitting enzymes. An equation illustrat—
`ing the hydrolysis of a fat, for example, palmitin, is:
`
`0
`stea si
`[I
`CaH5(OCCisH31)s + 31120 ——--a-"n
`Palmitin
`
`0
`ii
`C,H5(OH), + success,1
`Glycerol
`Palmitic acid
`
`If the hydrolysis is brought about by means of alkali, a soap is formed
`instead of a fatty acid, and the process is then called soponificetion.‘
`
`O
`II
`C3H5(OCC]5H3;)3 + 3NaOH
`Palmitin
`
`'_'_'—""
`
`0
`II
`CIH§(OH)3 + 3N30CC1§Ii31
`Glycerol
`Sodium palmitate
`(soap)
`
`In this equation the formula of sodium palmitate is written in such a
`manner as to show how it is produced by the action of the NaOH on
`the palmitin.
`It. might also be written CmHglCOONa. This substance
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 86
`
`Petitioner Microsoft Corporation — EX. 1032, p. 86
`
`

`

`Lirmus (l-‘.-\'l'$i
`
`.vxu Iii-IL-i'l'lil) 5U”S'l'.-\Nfilisl
`
`37
`
`is a typi -al soap. and the above equation illustrates the commercial mantl-
`faeture of soaps.
`
`Son ps-
`
`A soap is defined chemically as a metallic salt of a fatty acid contain-
`ing ten or more earlion atoms. All eonmu-reial soaps. however, are. mix-
`tures of several individual “soaps" because they are made from natural
`fats which are mixtures of glyeerides. The ulyccrides are all saponified
`at once, and each fatty acid radical is converted into the corresponding
`soap. Thus the product
`is a mixture correspomliog in composition to
`the fatty acid make—up of the original fat.
`Sodium and potassium soaps, hcing fairly soluhle in water, are Useful
`washing agents. Soaps of other metals, although too insoluhle in Water
`to form a lather, are very valualile for other purposes, as deserilied below.
`The consistency and washing qualities of soaps depend partly on the
`metal and on the fatty acid radicals of which they are composed. Thus
`from a given fat. sodium hydroxide will tend to produce the harder and
`potassium hydroxide, the softer soap.
`{in the other hand,
`if the same
`alkali
`is used throughout, a liquid fat, containing unsaturated or
`low
`molecular weight- fattv acid radicals, will tend to produce a soft or liquid
`soap, whereas a hard fat. like fallow will make a hard soap. Other things
`heing equal, the soaps of capric, lauric, and myristie acids, that is the
`saturated fatty acids containing 11], 12, and 14 carbon atoms,
`lather
`better, and of these the laurie soaps are the best.
`It is for this reason
`that fats such as palm and coconut oils, yielding a large amount of these
`particular fatty acids on hydrolysis, are so valuable in soap making.
`Water-soluble soaps are. classified as detergents, substances which, when
`dissolved in water, lower the surface tension of
`the water and help to
`loosen and was]: away particles of grease and dirt. Other kinds of
`detergents are also produced more or less directly from fats and have
`become so popular that over 1.2 million lb. were produced in 1950.
`These so-called "synthetic detergents," which should not he called soaps,
`are of many types, but all of them consist of a water-soluble, salt-like
`group attached to a long-chain, fat-like residue. A typical example is
`sodium alkyl sulfate, Btu-1033's, where it represents alkyl groups cor—
`responding to various fatty acids such as laurie, myristie, palmitie, and
`stearie. These synthetic detergents differ mainly from ordinary soaps by
`having a sulfate in place of the carhoxyl group. Since they form soluble
`calcium and magnesium Compounds. which are not precipitated by the
`minerals in hard water, they are as effective washing agents in hard water
`as in soft water. Their aqueous solutions are also practically neutral,
`whereas those of ordinary soaps are quite strongly alkaline and have. a
`_pH of about 9.
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 87
`
`Petitioner Microsoft Corporation — EX. 1032, p. 87
`
`

`

`33
`
`LIPIDES (FATS AN!)
`
`iii-:I..-\ra1i solar-wees)
`
`Various Hater-insoluble soaps of metals other than sodium or potassium
`have important industrial uses. Soaps of the higher saturated or slightly
`unsaturated fatty acids such as steai'ie, palmitie, and oleic acids, with
`such metals as aluminum, calcium, lead. barium, lithium and others, are
`used in making lubricating greases. When combined with lubricating
`oils.
`these soaps produce semisolid gels. or greases. More highly un-
`saturated acids such as linoleie or eleosteal‘ie are combined with lead,
`manganese. or cobalt to produce “driers” for use in paints, varnishes,
`and enamels. These soaps catalyze the oxidation processes, which came
`the films to “dry” or harden. Zinc oleate and stearate are. used as
`antisepties and astringents in medicinal preparations. Of the above soaps,
`aluminum and zinc stearates are quantitatively the most important, being
`produced annually to the extent of some 10 million lb. each.
`
`A erol'el'n leaf.
`
`When glycerol is heated strongly, and especially if a dehydrating agent
`such as potassium bisult‘ate is present.
`it decomposes into water and
`acrolein:
`
`a
`
`C3H5(OH)3 TSO.’ CH2=CHCHO + 21120
`
`The unsaturated aldehyde, aerolein, has a characteristic sharp, irritating
`odor and is partially responsible for the smell of burnt fat.
`Fats likewise give the aerolein test- sinee on heating to a sufficiently
`high temperature the. glycerides in the fat are. partially broken down with
`the eventual formation of acrolein.
`
`Iodine rmmber
`
`The unsatul'ation of a fat is determined by means of incline, which gives
`the so-ealled iodine number of a fat. The iodine number is the per-
`centage of iodine by weight that the fat will absorb;
`for example, if a
`fat has an iodine number of 100, one gram of the fat will absorb one
`gram of iodine. The following table shows how the iodine number gener-
`ally varies with the. physical state of the fats.
`It will he noted that
`the hard fat, tallow, has a low iodine number, 35—45, whereas lard, a
`soft fat, has an iodine number of 50—70, and the oils have iodine numbers
`ranging from 80 to 200.
`If judged by the low iodine number, butter,
`and especially coconut oil, should be hard fats. The low melting point
`of coconut. oil (about 25°) as compared with that of tallow [about 45°) is
`due to the presence of large quantities of glycerides of the lower saturated
`fatty acids. The softness of butter is caused by two factors, unsaturation
`and glycerides of low molecular weight.
`In most fats and oils only the
`first of these tWo factors plays a part.
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 88
`
`Petitioner Microsoft Corporation — EX. 1032, p. 88
`
`

`

`LimnEs
`
`(FATS AND Incl..\'l‘i=.n smear-moles)
`
`3"
`
`Table! 4—6
`
`Iodine. number (If
`
`saunte- emullmu nils and fats
`
`.
`(‘oconul oil ......
`Immortal.
`.......... _
`lleef
`talluw .
`..
`..
`.
`(Jim oil from heel tallnw
`Lard
`.
`.
`.
`Olive Oil
`l‘i-anul nil
`(‘ultnllseetl oil
`('ol'n oil
`.
`Soybean oil
`Linseed oil
`
`.
`
`.
`
`.
`
`..
`
`.
`.
`
`.
`
`.
`.
`
`....
`_
`.
`
`._
`.
`.
`
`.
`
`..
`
`_
`
`.
`
`.
`..
`..
`
`.
`..
`
`.
`_____
`..
`.
`.
`.
`... .
`_
`.
`.
`.
`.....
`.
`
`_
`
`..
`
`.
`
`.
`.
`
`.
`
`.
`,
`
`5~ 10
`26— 38
`35— 15
`4(1-
`:35
`Fill— 70
`:75!— ill]
`HT—Itll]
`IUl
`Ill}
`lll
`ill-l
`137— | Iii
`[Til-dull
`
`It is :I
`iodine number of any known fat.
`Linseed oil has the highest
`highly unsaturated oil and takes up atmospheric.
`(.rxygen \‘L-l'y readily
`to form a hard tough film. For this reason it. is peculiarly well adapted
`for paint. purposes. When paint
`is spread over a surface, the linseed
`oil takes up oxygen from the air and forms a thin, hard, watertight coat.
`No other oil has ever been found which is equal
`to linseed oil
`in this
`respect. Tang and soybean oils come nearer to it than any other oils and
`are used to supplement linseed oil in the paint industry. At the present
`time the demand for linseed oil
`is far greater than can he met by the
`supply. Were it possible to desaturatc other oils such as cottonseed
`and peanut oil so that- they would have the some drying capacity as
`linseed oil, it would he. of enormous benefit to the paint- industry. Un-
`fortunately no method for doing this has yet. been discovered, although
`the reverse process of saturating an unsaturated oil can be easily ac-
`complished. The term “drying oil” is applied to liquid fats. like linseed
`oil, which hare iodine numbers in the range 150 to 200 and form hard,
`dry films when spread over a surface and exposed to the air.
`The drying oils are unsuited for
`lubricating purposes because they
`tend to become gummy and sticky. The same. property of unsaturation
`operates, but in lubricating oils it is an undesirable property rather than
`a desirable one.
`
`Hydrogenation of oils
`
`The saturating or hardening of fats has become an important com-
`mercial process.
`If an oil or soft fat is exposed to the action of hydrogen
`in the presence of finely divided nickel
`[a catalyst} at a moderately
`high temperature (150° to 190"'('J.} and pressure (25 lb. per sq. in.).
`it combines with the hydrogen and is converted into a solid fat. This
`process is applied annually to several hundred thousand tons of un—
`saturated fats in the United States. Although not all of this hydrogenated
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 89
`
`Petitioner Microsoft Corporation — EX. 1032, p. 89
`
`

`

`90
`
`LIPIDES (FATS AND RELATED SUBSTANCES)
`
`is converted into edible fats, great quantities of well known
`material
`commercial products.
`(29., “Crisco” and “e'uowdrift,” are preparer!
`in
`this manner from peanut, cottonseed, and other oils. These fats are
`more stable to heat than natural fats, such as lard, and are, therefore,
`peculiarly well adapted to certain cooking operations, such as deep-fat
`frying. The natural
`fat-s tend to decompose at higher
`temperatures,
`owing,
`it is assumed, to the presence of small amounts of
`free fatty
`acid. The more free acid present in a fat, the more readily it is decom-
`posed by heat.
`
`Roncidify of fats
`
`When fats are kept for a long time, they develop objectionable odors
`and tastes, a condition which is known as rancidity. Many different
`factors such as heat, light, moisture, air, enzymes, bacteria, and metals
`are iiivolved in the decomposition of fats. The principal chemical changes
`are hydrolysis and oxidation. The former is particularly- important in
`the case of butter and other dairy products be ‘ausc the free fatty acids,
`produced when buttcrfat is hydrolyzed,
`include several of
`the lower,
`saturated series {c.g., bntyrie, caproic, etc., see Table. 4—5), which have
`very sharp, unpleasant odors. Rancidity due to oxidation develops par»
`ticularly in moderately unsaturated fats and oils, :1 group which includes
`the bulk of the common food fats. Atnmspheric oxygen slowly reacts
`to produce liydropcroxidcs. fats or fatty acids having an —OOH group
`attached to a carbon atom next to a double bond. Once formed,
`the
`
`further oxidation. As a result,
`hydropcroxides serve as catalysts for
`lower fatty acids, kctones, peroxides, and other substances are formed,
`and the glycerol disappears. The unpleasant odors and flavors of these
`products make.
`the fat rancid. Rancidity is a term which applies to
`any objectionable odor or taste in fats. no matter how brought about.
`There exist a number of different substances, not
`themselves fats,
`which have a remarkable power of slowing down the development of
`oxidative rancidity.
`Such substances are called antioxidants. They are
`present naturally in many fats, which have not been too extensively
`refined, and have a large influence on the keeping qualities of fats. Ex-
`amples of antioxidants are crude lecithin, hydroquinoac (HOCBI-LOII],
`vitamin C, and the tocopherols
`(vitamins E, p. 216). Only small
`amounts, of the order of
`1 per cent of the fat, or less, are sufficient to
`delay the onset of oxidative rancidity for extended periods. Antioxidants
`appear to function by interfering with the catalytic effect of the hydro-
`peroxidcs mentioned above.
`In so doing they are themselves slenvly
`oxidized, so that
`their effect eventually wears olT. Antioxidants are
`deliberately added to many food fats to improve their keeping qualities.
`They are also thought, by many investigators,
`to play an important
`biological role in preventing unwanted oxidations from occurring in viva.
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 90
`
`Petitioner Microsoft Corporation — EX. 1032, p. 90
`
`

`

`Helm-:5 (FATS .\.\‘o aisle-trim hl'lia'l‘ANtIl-Zri]
`
`91
`
`Determination of for
`
`in a foodstuff is determined by extracting,r the.
`The percentage of fat
`fat with ether and weighing it.
`11]
`tables of :Lllal_\‘.—cs
`this is generally
`spoken of as fat. or more correctly. ether extract.
`' It
`is Not necessarily
`all fat, since ct her will dissolve many other substam'es such as \t'axcb‘.
`resins. fatty acids. and coloring: matter. all of which may be. contained
`in natural fats. The ether extract of cereals is mainly fat. whereas a
`
`large proportion of that obtained from vegetables consists of fatty acids,
`plunsphulipides. no]1saponiliable matter. etc. The following table shims
`how variable is the composition of ether extract:
`
`Table 1—7
`
`(lumpusilion 01' ('llwr exlral‘l
`
`ilfoteri'ot
`extracted
`
`Potatoes ,.c .
`Bi’l'la‘
`,
`.
`.
`.
`.
`.
`(‘om .
`.....
`Barley .
`.
`.
`.
`Unis
`_.
`Pi 'as
`_
`Soybeans
`
`.
`.
`
`.
`
`_
`.
`
`.
`
`.
`
`.
`_
`.
`.
`
`.
`
`.
`
`.
`
`.Vratml
`furs
`(per rem)
`113.15
`23.0
`88.7
`73.0
`59.2
`SS .6
`$15.5
`
`Free fatty
`acids
`(per cent}
`56.9
`35.3
`6.7
`1-1.0
`35.4
`l 1.13
`1.2
`
`"Lecithin"
`(per cent)
`3.1
`
`03
`27:1
`1.8
`
`Noampum'fiubh-
`mum-r
`(per cent)
`10.9
`10.7
`3.7
`6.1
`2.7
`751
`1.5
`
`A special test for the determination of fat in certain dairy products,
`particularly milk, was introduced in 1890 by Stephan Moulton Babcock.
`The “Babcuck test,” as it
`is universally called, has been of decisive im-
`portance to the growth of dairying in this country, since it made. possible
`a quick, practical means of judging the butter fat prmluetioa of individual
`cows, permitting selection of the best producers for breeding. The test
`is made by treating a definite amount of milk with an equal volume of
`90 per cent sulfuric acid and warming the mixture gently.
`0:1 cen-
`trifuging this 111ixtnre,
`the fat separates as a distinct
`layer, which is
`measured in the neck of a special flask calibrated to read directly the
`percentage of butter fat.
`
`\VAXES
`
`Definition
`
`fats,
`together with the true.
`Waxes are classified as simple lipiilcs,
`but unlike fats they contain higher motlohydroxy {sometimes diliydroxy)
`alcohols in place of glycerol.
`'l‘hesc alcohols exist in the. wax in com-
`
`Petitioner Microsoft Corporation - Ex. 1032, p. 91
`
`Petitioner Microsoft Corporation — EX. 1032, p. 91
`
`

`

`92
`
`melons (Ears AM) RELATED SUBSTANCES)
`
`hination with fatty acids, that is, as esters. An example of an individual
`wax ester is cetyl palnlitate:
`
`if
`CH3(CH2)”CH200(CI'12)HCH3
`
`The