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`(cid:7)(cid:16)(cid:26)(cid:13)(cid:27)(cid:29)(cid:23)(cid:16)(cid:24)(cid:29)(cid:1)(cid:25)(cid:17)(cid:1)(cid:6)(cid:19)(cid:16)(cid:23)(cid:20)(cid:15)(cid:13)(cid:22)(cid:1)(cid:8)(cid:24)(cid:18)(cid:20)(cid:24)(cid:16)(cid:16)(cid:27)(cid:20)(cid:24)(cid:18)(cid:2)(cid:1)(cid:12)(cid:24)(cid:20)(cid:30)(cid:16)(cid:27)(cid:28)(cid:20)(cid:29)(cid:31)(cid:1)(cid:25)(cid:17)(cid:1)(cid:10)(cid:16)(cid:14)(cid:27)(cid:13)(cid:28)(cid:21)(cid:13)(cid:3)(cid:9)(cid:20)(cid:24)(cid:15)(cid:25)(cid:22)(cid:24)(cid:5)(cid:1)(cid:40)(cid:45)(cid:46)(cid:51)(cid:48)(cid:37)(cid:36)(cid:36)(cid:15)(cid:51)(cid:45)(cid:43)(cid:45)(cid:46)(cid:50)(cid:37)(cid:49)(cid:7)(cid:51)(cid:45)(cid:43)(cid:7)(cid:37)(cid:36)(cid:51)
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`(cid:27)(cid:33)(cid:48)(cid:50)(cid:1)(cid:46)(cid:38)(cid:1)(cid:50)(cid:40)(cid:37) (cid:17)(cid:41)(cid:46)(cid:44)(cid:33)(cid:50)(cid:37)(cid:48)(cid:41)(cid:33)(cid:43)(cid:49)(cid:1)(cid:18)(cid:46)(cid:44)(cid:44)(cid:46)(cid:45)(cid:49)
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`(cid:27)(cid:33)(cid:47)(cid:37)(cid:48)(cid:1)(cid:9)(cid:11)(cid:7)
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`(cid:19)(cid:41)(cid:39)(cid:41)(cid:50)(cid:33)(cid:43)(cid:18)(cid:46)(cid:44)(cid:44)(cid:46)(cid:45)(cid:49)(cid:15)(cid:30)(cid:45)(cid:41)(cid:52)(cid:37)(cid:48)(cid:49)(cid:41)(cid:50)(cid:54)(cid:1)(cid:46)(cid:38)(cid:1)(cid:25)(cid:37)(cid:34)(cid:48)(cid:33)(cid:49)(cid:42)(cid:33)(cid:1)(cid:6)(cid:1)(cid:24)(cid:41)(cid:45)(cid:35)(cid:46)(cid:43)(cid:45)(cid:7)
`
`Actavis - IPR2017-01100, Ex. 1029, p. 1 of 6
`
`
`
`1184
`
`Densities of Vegetable Oils and Fatty Acids
`
`H. Noureddini‘, 3.0. Tech and L. Davis Clements
`Department of Chemical Engineering. University of Nebraska-Lincoln, Lincoln, Nebraska 88583—0126
`
`Complete data for density as a function of temperature
`have been measured for a number of vegetable oils
`(crambe, rapeseed. corn, soybean, mill-tweed, coconut, les-
`querella), as well as eight fatty acids in'the range C9 to
`C22 at temperatures from above their melting points to
`110°C (230°F). The specific gravity and density measure-
`ments were performed according to American Society for
`rfleeting and Materials (ASTM) standard test methods D
`368, D 891 and D 1298 for hydrometers and a modified
`ASTM D 369 and D 891 for pycnometers. Correlation con-
`stants, based on the experimental data, are presented for
`calculating the density of fatty acids and vegetable oils
`in the range of temperature from 24°C [75°F] or the
`melting point of the substance, to 110°C (230°F). The con-
`stants are valuable for designing or evaluating such
`chemical process equipment as heat exchangers, reactors,
`process piping and storage tanks. Estimated density of
`fatty acids by a modified Beckett equation is also
`presented.
`
`KEY WORDS: Density, fatty acids, specific gravity, vegetable oils.
`
`Density or specific gravity data are important in numer-
`ous chemical engineering unit operations in the fatty acid
`industry. Representative excruples include reactors for
`splitting of fatty acids or conversion of fatty acids to their
`derivatives, distillation for separation of fatty acids. or
`for designing storage tanks and process piping. In addi-
`tion, the pure component data for fatty acids may be used
`to ascertain mixture property values and to estimate oil
`density.
`The data were measured by both hydrometer and pyc-
`nometer procedures in a single constant-temperature bath.
`Pycnometer measurements provide the true density of the
`material and the hydrometer measures specific gravity.
`Due to the tedious procedure involved in pycnometer
`measurements, they were used only for some of the data
`to validate the hydrometer readings over the entire range
`of temperature This procedure resulted in a correction fac-
`tor for hydrometer measurements. In all measurements
`the correction never exceeded 0.2%.
`
`EXPERIMENTAL PROCEDURES
`
`
`
`A Precision Scientific (Chicago, IL) constant—temperature
`bath with a Micro-set Thermoregulator, in accordance
`with American Society for Testing and Materials (ASTM)
`D 445 (1), was used in the procedures for specific gravity
`and density determinations. This assembly maintains a
`temperature uniformity of
`i0.0033° C {i005 °F)
`throughout the range of 20 to 130°C (68 to 266°F), ex-
`ceeding the ASTM D 445 (1) requirements. Fisher’s Preci-
`sion Specific Gravity Hydrometers (Fisher Scientific, Pitt-
`sburgh, PA), ASTM D 1298 {2] with subdivisions of 0.001,
`and Fisher thermometers, ASTM D 445 (1), with subdivi-
`sions of 0.056°C (01° F), were used for specific gravity and
`temperature readings, respectively.
`*To whom correspondence should be addressed at Department of
`Chemical Engineering, 236 Avery Laboratory, University of
`Nebraska-Lincoln, Lincoln, NE 68588-0126.
`FIG. I. Pycnometer membly.
`Actavis - IPR2017-01100, Ex. 1029, p. 2 of 6
`Actavis - lPR2017-01100, Ex. 1029, p. 2 of 6
`JAOCS, Vol. 69, no. 12 (December 1992)
`
`A glass cylinder was installed through one of the holes
`in the bath cover assembly. The sample was placed inside
`the glass cylinder for hydrometer measurements. The bath
`temperature was set at the desired temperature and was
`monitored with a glass thermometer during the experi-
`ment. The temperature of the sample inside the glass
`Cylinder was monitored with a second thermometer. At
`higher temperatures, where a temperature gradient may
`exist, the bath temperature was increased to maintain the
`desired temperature inside the cylinder. The specific gravi-
`ties were determined according to the procedures in
`ASTM methods D 1298, D 368, and D 891 (2-4].
`The pycnometer measurements were performed along
`with the hydrometer procedures in the same bath. Three
`lO-mL Fisher pycnometers. in accordance with ASTM D
`369 (5), were used in all measurements. Pycnometers were
`filled with the sample at a temperature below the bath
`temperature. Heat resistant tubing was slipped over the
`outside of the pycnometer neck to prevent direct contact
`between the bath fluid and the capillary opening of the
`bottle. Figure 1 shows the pycnometer assembly. This
`assembly was secured to the bath cover and clip and
`
`Bath CaVer
`
`Bath Fluid Level
`
`Temperature Resistant Tubing
`
`Pycnometer
`
`
`
`DENSITIES 0F VEGETABLE OILS AND FATTY ACIDS
`
`TABLE 1
`
`Fatty Acid Distributions and Sources of Vegetable Oils
`
`‘70 Cornpositim‘I
`Vegetable
`Source or manufacturer
`Saturated
`Monounsaturated
`oils
`Polyunsaturated
`
`16
`79
`5
`Crambeb
`Texas A&M University. College Station, TX
`University of ldaho, Moscow, ID
`21
`72
`7
`Rapeseedb
`64.3
`21.4
`4.3
`Corn
`Hain Pure Food Co. Inc., Los Angeles, CA
`Hain Pure Food Co. Inc., Los Angeles. CA
`57.1
`28.0
`14.3
`Soybean
`NA
`NA
`NAC
`Milkwaed
`Biological System Eng, U. of Nebraska, Lincoln, NE
`1.0
`5.0
`94.0
`Coconut
`Vinton Pop Corn Co., Vinton, IA
`Jojoba Growers & Processors lnc.. Apache Junction, AZ
`20.9
`76.0
`3.1
`Lesquerella
`
`“Provided by the manufacturers. bApproximate values. CNot available.
`
`TABLE 2
`
`Purity of Fatty Acids
`Acids Manufacturer % Purity“
`
`
`
`
`
`Nonanoic
`Capric
`Laurie
`Myristic
`Palmitic
`Stearic
`Oleic
`Erucic
`
`98
`99—100
`99—1 00
`99
`99
`9 5
`98
`9 0
`
`“Provided by the manufacturers.
`
`Kodak, Rochester. NY
`Sigma1 St. Louis, MO
`Sigma
`Kodak
`Sigma
`Aldrich, Milwaukee, WI
`J .T. Baker. Pbillipsburg, PA
`Sigma
`
`immersed inside the bath. Except fer the modifications
`for the pycnometer assembly, the procedures in the ASTM
`standard test methods D 891 andD 369 (4.5) were followed
`for the density determinations.
`The fatty acid composition and source or manufacturer
`of each vegetable oil are shown in Table 1. Table 2 shows
`the purity and the manufacturers of the fatty acids used.
`The information on the fatty acid c0mpositi0n of vege—
`table oils and purity of the fatty acids were provided by
`the manufacturers.
`
`RESULTS
`
`The scale readings for the hydrometer were corrected for
`the glass expansion by using a glass expansion coefficient
`of 25 X 10“i per “‘0. The specific gravity data for crambe
`and milkweed seed oils and for oleic acid were measured
`
`
`
`ments are also included. As expected. the deviations found
`were small. The mean deviation was less than 0.07% for
`all data. Figures 2 and 3 show the experimental and linear
`predictions for vegetable oils {lesquerella milkweed,
`crambe) and for saturated fatty acids [nonanoic capric.
`lauric, myristic, palrnitic, stearic}, respectiver Lines show
`the linear correlations compared to the experimental
`points.
`The difference between successive test results by the
`same apparatus under constant operating conditions on
`identical test material never exceeded 0.0005 for hydro-
`meter scale readings and 0.003 f0r pycnometer measure-
`ments. These are within the sensitivity limits imposed by
`ASTM test methods D 1298 and D 369 (2,5), respectively.
`Random examination of results for other samples, for
`which hydrorneter measurements were principally per-
`formed. confirmed the correction applied to the scale
`readings. Corrected data were also within the repeatability
`specifications given by the ASTM methods, thus justi-
`fying the application of the correction factor for the
`hydrometer measurements.
`The modified Rackett equation [8) also can be used for
`calculation of fatty acid and vegetable oil densities. This
`approach can be used directly in most computer-aided—
`process-design programs such as PRO/II”, DESIGN
`IITM or HySimTM. The modified Beckett equation re-
`quires the critical properties and an empirical parameter,
`Z“, for each acid as the basis for computing density as
`a function of temperature. The required critical proper-
`ties and Rackett parameters are usually available in the
`component library or may be easily incorporated into the
`program data file. The modified Rackett equation is as
`follows:
`MW
`2 =—
`RT: Z[‘l+(1—Trl2{7]
`pc
`RA
`
`with both hydrometers and pycnometers. The hydrometer
`scale readings were corrected according to the pycnorneter
`measurements. The correction was equal to 0.0025. This
`correction was uniform and did not depend on tempera- '
`ture or type of oil or acid used. This correction was then
`Tc and Pr are the critical temperature and pressure,
`applied to the rest of the samples, f0]: which only the
`respectively; Q is the density; TI
`is the reduced
`hydrometer measurements were performed Densities were
`calculated by multiplying the specific gravities by water
`temperature [Tr = 'D'Tc); R is the universal gas constant;
`density (0.99904 glmL) at 155°C {60.0 °F}. This is the
`MW is the molecular weight; and ZRA is the Rackett
`parameter, a Correlating parameter unique to each com-
`calibration temperature of the hydrometBrs. The results
`are tabulated in Tables 3 and 4- Available literature values
`pound. Critical properties for the fatty acids mentioned
`in this work are shown in Table 7. A more complete listing
`(6,7) at 25°C (77°F) are presentEd for comparison.
`A linear correlation was fitted to the experimental data.
`of fatty acid critical properties was found in earlier works
`The linear coefficients are tabulated in Tables 5 and 6. The
`(Halvorsen, 1D,, W.C. Mammel. Jr. and L. Davis Clements,
`percent mean deviations frg‘rgteax
`féi‘f’i'tlflz’li‘ial‘ib‘ii 13‘6",“E‘i<‘°’.1“i‘l)‘ia§a§"p. 3 of 6
`Actavis - IPR2017-01100, Ex. 1029, p. 3 of 6
`JAOCS, Vol. 69, no. ‘12 (December 1992)
`
`{1]
`
`
`
`TABLE 3
`
`H. NOUREDDINI ET AL.
`
`Density of Vegetable Oils
`Density (gme)
`
`Rapeseed Lesquerelfi Corn Soybe an Milkweed“ Coconut
`Crambefl
`
`
`
`
`
`Temperature
`“ C (° F}
`
`[75.0)
`23.9
`37.3 {100.0}
`48.9 (120.0)
`60.0 (140.0)
`82.2 (180.0}
`100.0 (212.0)
`110.0 1230.0)
`
`0.9078
`0.8977
`0.8898
`0.8829
`0.8681
`0.8564
`0.8501
`
`0.9073
`0.8987
`0.8908
`0.8839
`0.8636
`0.8579
`0.8511
`
`0.9188
`0.9082
`0.9028
`0.8939
`0.8800
`0.8679
`0.8610
`
`0.9193
`0.9032
`0.9023
`0.8939
`0.8795
`0.3674
`0.3615
`
`0.9203
`0.9097
`0.9018
`0.8934
`0.8790
`0.8684
`0.8605
`
`0.9107
`0.9033
`0.8949
`0.8795
`0.8669
`0.8605
`
`0.9393
`0.9307
`0.9229
`0.9152
`0.3999
`0.8879
`0.8830
`
`0903—0907
`0.912-0.917
`0914—0918
`0916—0918
`25 25 25 25
`“By direct pycnometer determination. Other values by corrected hydrometer determination. bRef. 6.
`
`
`
`
`
`
`
`Literature data
`
`Temp. (°C)b
`
`TABLE 4
`
`Density of Fatty Acids
`Density (gme)
`Myristic
`Pahnitic
`14:0
`16:0
`
`Temperature
`°C (°F)
`
`Nonanoic
`9:0
`
`Capric
`10:0
`
`Oleica
`13:1
`
`
`
`Erucic
`22:1
`
`querella; i“). milkweed; and (fl), crambe.
`
`
`
`
`
`23.9 (75.0]
`37.8 (100.0]
`48.9 (120.0)
`60.0 (140.0)
`71.1 1160.0]
`82.2 (180.0)
`93.9 (210.0)
`110.0 (230.0)
`121.1 (250.0}
`
`Literature data
`
`Temp. (“01b
`
`0.9013
`0.8913
`0.8833
`0.8744
`0.8665
`0.3571
`0.3445
`0.8371
`
`0.8863
`0.8788
`0.8694
`0.8615
`0.8526
`0.8405
`0.8332
`
`.
`
`0.3729
`0.8634
`0.8560
`0.3471
`0.8351
`0.8282
`
`0.8590
`0.8516
`0.3432
`0.8321
`0.8257
`
`0.8496
`0.8412
`0.8302
`0.8237
`
`0.3387
`0.8276
`0.8217
`0.8148
`
`0.8928
`0.8823
`0.8753
`0.8674
`0.8605
`0.352]
`0.8400
`0.8327
`
`0.8763
`0.8689
`0.8611
`0.8532
`0.8459
`0.8348
`0.8284
`
`0.8699
`0.850
`0.8390
`0.3414
`0.8439
`0.8477
`0.8531
`0.8570
`30 55 30 80 80 80 80 80
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`clBy direct pycnometer determination. Other values by corrected hydrorneter determination. bRef. 6, except for erucic acid (ref. 7).
`
`
`0.940{)u\
`0.9100"
`
`0.9000-
`
`
`
`Density[gImLJ
`
`03909.;
`
`0.8800"
`
`08700-5
`0.3600-
`
`9.8500-
`
`08400-
`0.8300‘
`i
`0.32007:
`
`
`
`1
`1'
`
`0.9300}
`
`
`
`Density(glmIJ
`
`0.9200j
`
`0.9100
`
`(Ii-90001
`0.8900-
`
`5
`0.8800-I
`
`0.8?00i
`08600-
`1
`83509}
`
`0840020
`
`30
`
`40
`
`70
`50
`50
`Temperature (°Cl
`
`30
`
`90
`
`100
`
`0810020
`
`3'0— 40
`
`50
`
`9'0
`80
`70
`50
`Temperature [°C)
`
`100
`
`:10 120
`
`130
`
`FIG. 2. Density vs. temperature for vegetable oils. The lines are cor-
`relation derivatives and the points are experimental data. 1+). Les-
`
`FIG. 3. Density vs. temperature for fatty acids. The lines are cor-
`relation derivatives and the points are experimental data. (a).
`Nonanoic acid; (+1 capric acid; 1*), lauric acid; “III. myristic acid; (X).
`palmitic acid; and (A), stearic acid.
`Actavis - IPR2017-01100, Ex. 1029, p. 4 of 6
`Actavis - lPR2017-01100, Ex. 1029, p. 4 of 6
`JAOCS, Vol. 69, nd ‘12 (December 1992)
`
`
`
`DENSITIES OF VEGETABLE OILS AND FATTY ACIDS
`
`TABLE 5
`
`Linear Correlations“ for the Vegetable Oil Densities {glmL)
`
`
`
`
`
`Temperature range
`% Mean deviation
`Data points
`ConStants
`Vegetable
`
`
`
`m c n roils (3C?
`Crambe
`—6.665F‘.-04
`9.2300E-01
`0.032
`23.921100
`Rapeseed
`—6.550E-04
`9.2305E-01
`0.029
`23.9-110.0
`Corn
`—6.650E-04
`9.3432E-01
`0.056
`23.9—110.0
`Soybean
`—6.674E-04
`9.344113-01
`0.057
`23.9—110.0
`Milkweed
`—6.820E-04
`9.3552E-01
`0.069
`23.9—110.0
`Coconut
`—7.000E-04
`9.3716E-01
`0.026
`37.8—110.0
`
`0.0499.5569E—01Lesquerella —6.709E-04 23.9-110.0
`
`
`
`“Density = c + mT.
`
`TABLE 6
`
`Linear Correlations“ for the Fatty Acid Densities (gImL)
`
`
`
`
`
`
`
`«magnum-Joe
`
`
`
`Data points % Mean deviation Temperature range
`constants
`Fatty
`
`
`
`Carbon :11 c n racids l“ C)
`0.048
`23.9—110.0
`0.047
`37.3—110.0
`0.067
`48.9-110.0
`0.055
`60.04100
`0.060
`71.171100
`0.036
`SEE-121.1
`0.023
`23.9—110.0
`0.042
`37.8—110.0
`
`Nonanoic
`Capric
`Laurie
`Myristic
`Palmitic
`Stearie
`0191::
`Erucic
`
`9:0
`10:0
`12:0
`14:0
`16:0
`18:0
`18:1
`22:1
`
`—7.595E—04
`—7.453E-04
`—7.319E-U4
`—6.727E-04
`76.649E~04
`-6.081E-04
`*6.982E-04
`—6.694E-04
`
`9.2015E-01
`9.1452E-01
`9.0792E-01
`8.9909E-01
`8.9634E—01
`3.8838E-01
`9.0946E-01
`9.0131E-01
`
`“Density = c + 1117'.
`
`TABLE 7
`
`Fatty Acid Densities and Properties for Use with the Beckett Equation
`
`
`Fatty acid (density, gme)
`Erucic
`Oleic
`SLearic
`Myristic
`Laurie
`Gepric
`Nonanoic
`Pelmitic
`
`22:1
`‘ 18:1
`13:0
`14:0
`12:0
`10:0
`9:0
`16:0
`
`MW
`Tc (K)
`PB (bar)
`ZRA
`
`158.24
`717.03
`2518
`0.24654
`
`172.27
`730.84
`22.92
`0.24419
`
`200.32
`756.21
`19.22
`0.23862
`
`228.37
`779.07
`16.35
`0.23263
`
`256.43
`799.89
`14.08
`0.22641
`
`284.48
`819.00
`12.25
`0.22041
`
`284.48
`819.41
`12.76
`0.22344
`
`340.59
`853.41
`9.87
`0.21177
`
`Temperature [30 (“F11
`23.9 (75.0)
`37.8 (100.0)
`48.9 [120.0]
`60.0 (140.0)
`71.1 060.0)
`82.2 (180.0}
`98.9 {210.0}
`110.0 (230.0)
`121.1 (250.0)
`
`0.9015
`0.8912
`0.8829
`0.8745
`0.8660
`0.8573
`0.8442
`0.8353
`
`0.8910
`0.8820
`0.3748
`0.8675
`0.8602
`0.8528
`0.8415
`0.8340
`
`
`
`0.060% Mean deviatitm, r 0.102
`
`
`
`Actavis - IPR2017-01100, Ex. 1029, p. 5 of 6
`Actavis - lPR2017-01100, Ex. 1029, p. 5 of 6
`
`
`
`H. NOUREDDINI ET AL.
`
`The modified Rackett equation predicts the liquid den-
`sity with an average error of 0.08 %, which is of sufficient
`accuracy for use with process design calculations.
`
`ACKNOWLEDGMENT
`
`The authors express their gratitude to U. S. Department of Agricul-
`ture Cooperative State Research Service for its support of this work.
`
`. Ibii, 1991. pp. 484—488. Method D 1298.
`. Ibid, 1991, pp 132-133. Method D 368.
`. Ibid, 1991, pp. 1—4, Method D 991.
`. Ibid. 1991, pp. 134—136, Method D 369.
`. Formo, M.W., E. Jungermann. EA. Norris and ND. Sonntag,
`Bailey’s Industrial Oil and Fat Products, edited by D. Swern, 4th
`edn, Vol. 1. John Wiley and Sons, New York, 1979, pp. 186—189.
`. Ullmann’s Encyclopedia of Industrial Chemistry, edited by W.
`Gerhartz, Y.S Yamamoto, L. Kandy. J.F. Rounsaville and G.
`Schulz. 5th cer, Vol. A10, 1985, p. 247.
`. Spencer, C.F. and RP. Danner, J. Chem. and Eng. Dam 171-236
`(1972).
`
`
`
`REFERENCES
`
`1. Methods of the American Society for Wasting and Materials, edited
`by Susan P. Canning, Paula C. Fazio, Donna Fisher, Elizabeth L.
`Gutman. Catherine T. Hsia, Sharon L. Kauffman, Joanne Kramer,
`Marianne Lane. Christine M. LemWeber and Patricia A. McGee,
`1991, pp. 168—1?3, Method D 445.
`
`[Received May 1, 1992; accepted October 12, 1992]
`
`Actavis - IPR2017-01100, Ex. 1029, p. 6 of 6
`Actavis - lPR2017-01100, Ex. 1029, p. 6 of 6
`JAOGS, V01. 69, no. 12 (December 1992}
`
`