List of references to the literature on tall oil (tallol, liquid rosin, pine oil or black liquor soap)

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Title:
List of references to the literature on tall oil (tallol, liquid rosin, pine oil or black liquor soap)
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Book
Creator:
Bray, M. W ( Mark W )
Martin, J. S
Smith, L. H
Forest Products Laboratory (U.S.)
University of Wisconsin
United States -- Forest Service
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U.S. Dept. of Agriculture, Forest Service, Forest Products Laboratory ( Madison, Wis )
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LIST OF 1RlET[NCEIS TO T1E ITITAEITAUIE


ON TAIL OIL


(Tallel, Liquid Iosin, Pinc oil, or

IBlacM Liquor Soap)








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I
_________________ -__________________I____




UNITED STATES DEPARTMENT OF AGRICULTURE
FOREST SERVICE
FOREST PRODUCTS LABORATORY


Madison,


Wisconsin


In Cooperation with the University of Wisconsin
Revised, August 1938


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LIST OF REFERENCES TO THE LITERATURE ON TALL OIL
(TALLOL, LIQUID ROSIN, PINE OIL OR BLACK LIQUOR SOAP)

By
Me W. Bray, Senior Chemist
J. S. Martin, Associate Engineer
and
L. H. Smith, Research Fellow, Victoria, Australia

Revised August 19358




1. P. Klason, Tek. Tid. 23, 31(1893).

2. E. Larson, Svensk. Kern. Tid. ;l, 14g (1905).

3. H. Bergstrom and 0. Fagerlund, Jernkontorets Ann. Bihaug. 9, 575,
649 (190og).
4. We Fehrion, Z. Angew. Chem. 22, 582 (1909).

5. H. Bergstrom, ibid 11, 297 (1910); ibid 12, 507 (1911).
6. Pine oil obtained in the manufacture of soda cellulose by Hilding
Bergstrom. Papier-Fabricant 9, Fest. Auslandschieft 76-82,
C.A. 6, 421 (1912).
7. H. Bergstrom, Papier-Fabr. 11, (25) 730 (June 20, 1913).

8. C. G. Schwalbe, Chem. Ztg. 38, 926 (1914).

9. Constituents of colophony and sulphate black liquor by 0. Ashan.
Ber. 45:867-86 (1921); abst. J.S.C.I. 40 (12):439A (June 30, 1921);
abst. Paper Trade J. 7_ (25): 54 (Dec. 22, 1921).

10. Some experiments on the separation of fatty acids and resin acids
in the liquid resin from sulphate pulping process by Astrid Cleve
von Euler. Arkiv. Kemi. Mineral Geol. (4): 21 (1921). C. A.
16: 2405 (1922).
I1. H. Sandquist, Ing. Vetenspaps. Akad. Handle. No. 10 (1922).

12. Kiefernol (Liquid rosin, poly terpen, sulfatharz) by Hakan Sandquist,
Papier-Fabr. 20, (50): 1713 (Dec. 17, 1922).

13. Process for the conversion of tall oil into technically useful
products, by Josef Ziv, Ger. Pat. 494,950 (June 9, 1923), C. A.
24, 3670 (July 20, 1930).


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14. Experiments with sulphate soap and sulphate oil (floating resin), by
H. E. Wahlbcrg. Svensk. Papers.-Tid. 27:l68-9 (1924). C.A. 18:
24o9 (1924)
15. Hardened fatty products from liquid resin, by H. 0. V. Bcrgstrom.
Swed. Pat. 57,226 (Sept. 3, 1924).
16. Aqueous emulsions of solutions of tall oil, by Hein and Comp.
Ger. Pat. 479,085 (June 10, 1925); C.A. 2-: 4842 (1929).
17. Fatty acids in pine oil, by T. Hasselstrom. Paper Trade J. 8_ (2):
60-64 (July 8, 1926); Papers och Travarutiskrift (Finland) (22):
632 (1925)Abs. in Paper Trade J. 84, (15):49 (April 14, 1927).
Finish Pat. 11,469 (NTovember 26, 1925). Finnish Pat. 11,455
(Novebcr 23, 1925).
18. Harz der hndlholzer, by R. Sieber, Verlag der Papier Ztg. Berlin
1925.
19. Rosin from uulp mill black liquor, by F. E. Greenwood. U. S. Pat.
l,56C:-?6 (Nov. 3, 1925): C.A. 20, 290 (1926).
20. Tall oil (properties of), by Duesberg, Seifensieder-Ztg. 52, 873
(1925); C.A. 20, 514 (1926).
21. Composition and utilization of tallol, by Maurice De Keghel. Rev.
chim. ind. 35, 170 (1926); C.A. 21, 1354, (1927),

22. Method for separating solid, resin-like compounds and oily fatty
acids from tall oil. H. Nordlinger, Chemischo Fabrik. Florshcim
A. G. Ger. Pat. 434,924 (1926).
23. Preparation of fatty acid compounds, by A. Riebecksche Montan-werke
A. G. Ger. 429,272 (1926).
24. Process for obtaining fatty acids from raw tall oil, by Oel-und fett
Chemic G. m. b. h. Magdeburg. Ger. Pat.4g4,243
(Oct. 12, 1926); Brit. Pat. 279,697 (Oct. 11, 1926); C. A. 24,
984 (Feb. 20, 1930).
25. Purification of liquid rosin. Papier-Fabri. 24), 180 (March 21, 1926);
Paper Trade J. _, (2):60 (July 8, 1926), Ab. in Paper Trade J.
L3, (15):49 (April 14, 1927); C. A. 20, 3566 (1926).
26. Tall oil, a byproduct of sulphate pulp mfg., by '. Ditmer. Z. angew.
chem. 3, 262, (1926); C. A. 20, 2072 (1926).
27. Tall oil products. (Oel- und fett chemie G.rm.b.h.) Ger. Pat. 477,829
(Dec. 5, 1S26). Nor. Pat. 45,894 (Nov. 11, 1927); C.A. 23, 4842
(1929).
28. Treating pulpmill black liquor, by F. E. Greenwood. U. S. Pat.
1,593,656 (July 27, 1926); C.A. 20, 3236 (1926).


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29. Treating tall oil. A. Schultze and co. Brit. Pat. 281,637 (D'c.
4, 1926); C.A. 22, 3529 (1928).
30. Composition and. utilization of tall oil, by M. De Keghel. Pulp and
Paper Mag. Canada 26, (16):529, 546 (April 19, l2g); C.A. 21, 1352
(1927); 22, 3295 (1928); Paper Trade J. 95, (21):50 (11ov. 2W, 1927);
abs. Paper Trade J. 97 (10):71 (Sept. 6, 1928).
31. Residual oils. Oel.-und Fett-cheirie. G.m.b.h. Frr:'-ch Pat. 643,853
(Nov.15, 1927); C.A. 23, 1750 (1929).
32. Manufacture of floating soap, by C. H. .icLelson. Finn. Pat. 12,689
(May 9, 1928).
33. Purifying oils, by Soc. Meusienne de Prod. Chim. Fr. Pat. 656,728
(June 29, 1928); C.A. 23, 4343 (1929). Fr. Pat. 663,728 (Jan. 5,
1929).
34. Recovery resinous products in wood pulp mfg., by E. H. French. U.S.
Pat. 1,693,586 (Nov.27, 1928); C.A. 23, 722 (1929).
35. Recovery of resins from black liquors, by K. G. Bergstrom. Fr. Pat.
663,416 (Feb. 6, 1928); C.A. 2_4, 739 (1930).
36. Process for the recovery of priytosterin, fatty and resinic acids ob-
tained from raw sulphate soap as byproducts in the manufacture of
sulphate soap. Satt att utvinna fytosterin, fettsyror och hartssyror
ur ra sulfatsapa, by H. Sandqvist and T. 0. H. Lindstrom. Swed. Pat.
o80,941 (March 22, 1928).
37. Use of tallol (liquid rosin) in the alkali wash of petroleum disstillate,
by K. Dittler, Chem.-Ztg. 52, 577 (1928); C.A. 22, 4238 (1928); abs.
Paper Trade J. a, (S):80 (August 22, 1929).
38. Working up cellulose industry byproducts, by C. H. Michelson. Ger. Pat.
503,030 (July 27, 1928); C.A. 24, 5157 (1930).
39- Process for treating talloel, by Willi Schultze. U.S. Pat. 1,736,802
Nov. 26, 1929; C.A.24, 744 (1930).
40. Recovery of rosin. Soc. chim. des resins du pin. Tor. Pat. 47,181
(Feb. 4, 1929).
41. Phytosterol from sulphate soap, by Ewald Pyimlh. Acta Chem. Fennica
1, (10, 12):125 (Dec. 15, 1930).
42. Rosin soap material from spent wood liquors, by Viggo Drcwsen. U.S.
Pat. 1,778,523 (Oct. 14, 1930); C.A. 24, 6016 (1930).
43. Valuable constituents of sulphate soap, by H. Sqndqvist and T. H.
Lindstrom. Tekn. Tidskr., Chemic 60, 41 (1930).


21129






44. Liquid resin and its possible uses, by W. Schmid. Papier-Fabr. 2?,
(1):l (Jan. 4, 1931); abs. Paper Trade J. 2,(20)62 (May 14, 1931);
Zellstoff u. Papicr 13, (12):571 (Dec. 1933); C.A. 2_8, 2529 (1934).
45. Method of treating talloel, by Willi Schultze. U.S. Pat. 1,826,224
Oct. 6, 1931. Paper Trade J. 9, (2):29 T.S.15. (July 14, 1932);
C.A._26, 613 (1932).
46. Process for the distillation of floating rosin precipitated as a by-
product in the manufacture of sulphate soap, by E. Ocman. Stocksund.
Finnrm. Pat. 15, 731 (Feb. 27, 1931).
47. Process of recovering resinous byproducts in the manufacture of wood
Vulp, by E.H.French. U.S. Pat. 1,810,472 (June 16,1931); C.A. 2_,
708 (1931).
48. Process for working up tall oil, by Robert Held and Hans Franzen.
Ger. Pat. 578,843 (Nov. 6, 1931); C.A. 2., 922, (Feb. 10, 1934).
49. Refining of "soap" floating on the waste liquors of cellulose manufacture,
by C.H. Michelson. U.S. Pat. 1,823,752 (Sept. 15, 1931); C.A.
26, 305 (1932).
50. Sulphate black liquor soap disposal, TAPPI Special Report No. 152,
(April 10, 1931).
51. Tall oil and its possible uses, W. Schmaid, Farben-Chemiken 2, 306 (1931)
Cf. C.A. 25, 3165 (1931); C.A. 25, 5582 (1931). Papier-Fabr. 2_,
(1);1 (Jan. 4, 1931); C.A. 25, 3165 (1931); Paper Ind. 12, 2117
(1931).
52. Use of tall oil as core binders. Imp. Chcr.i. Ind. Ltd. and H. M.
Bunbury. Eng. Pat. 348,315 (May 14,1931); C.A. 26, 3087 (1932).

53. Compositions adapted for use as emulsifying agents, by Imp. Chem.
Industries Ltd. Lond., H. M. Bunbury, and R.P.McGlynn. Eng. Pat.
369,985 (Mar. 29, 1932). C.A. 21, 3046 (1933).
54. Process for the continuous manufacture of liquid rosin from raw soap
obtained as a byproduct in the manufacture of sulphate pulp.
H. Bergstrom and K. Ccdarquist. Swedish Pat. 87, 842 (Sept. 8,
1932). Abs. Paper Tr-tdo J. 106(8):136 T.S. 88 (Feb. 24, 1938).
55. Process for the mfg. of material from pine oil for floor and wall
covering, "Deutsche Lineoleum wcrke, A.G. Berlin." Swed. Pat.
80,570 (Feb. 8, 1932). Abs. Paper Tr-de J. 101, (7):45, (August
15, 1935.)
56. Process for the preparation of "soft soap"t from so-called "floating
rosin" as a byproduct in the mrnufacturo of sulphate pulp, by
A. Hellstrom. iTor. Pat. 52,815 (Oct. 28, 1932); Abs. P-pcr Tra-de
J. (22):33, (May 31, 1934).


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57. Process of recovering rosin from rosin coiltaining soap produced in the
mfg. of paper frorm rosin containing wood, by L.IT. Bent. U.S. Pat.
1,888,581 (Nov. 22, 1932); C.A. 27, 1503 (1933).
58. Process for refining and discoloring of raw sulphate soft soap, by
Ewald Pyhala. U.S. Pat. 1,887,246 (Tov. 8, 1932).

59. Refining liquid rosin, by H. Bergstrom. Svensk. Papers-Tidn. 3, (5):
156, 161 (March 15, 1932); C. A. 26, 3124 (1932).
60. Tall oil distillate in soaps, by G. Knugger. Seifensieder Ztg.
2., 7S2 (1932); C.A. 27, 1224 (1933).
61. Cellulose turpentine, b-, A. H. Weissner. Farbe u. Lack. 261 (1933);
C.A. 2a, 4073 (1933).
62. Centrifugal separator for the removal of fats, soaps, and resins from
diffuser black liquors, by S. D. Wells. U.S. Pat 1,934,957 (Nov.
14, 1933); Abs. Paper Trade J. _ (22):33 (May 31, 1934).
63. Distribution of the sulphate soap during the washing of the diffusers,
by BergstrSm and Cederquist. Svenske Papers-Tidn. 35 (17):571 (Sept.
15, 1933); Abs. Paper Trade J. 103 (5):32 (July 30, 1936).
64. Method of obtaining phytosterol fatty acids and resin acids from raw
soap or liquid resin obtained in the manufacture of cellulose
according to the sulphate method, by Sandqvist, Hakan. U.S.
Pat. 1,940,372 (Dec. 19, 1933); C.A. 28, 1533 (1934).

65. Method of polymerizing, condensing, and oxidizing tall oil and the
resulting product, by R. H. Patch and F. Dambacher, U. S. Pat.
1,938,532 (Dec. 5, 1933); C.A. 28, 1207 (1934).
66. Production of valuable products from tall oil, by Hans Franzen and
Robert Held, U.S. Pat 1,921,556 (Aug. 8, 1933); C.A. 271, 5207 (1933)
67. Recovering rosin from crude collected mixtures, by A.R. Hitch and I. A.
Ebaugh. U.S. Pat.l,899,388 (Fob. 28, 1933); C.A. 27, 3094 (1933)
68. Sulphonated derivatives of tall oil, by J.R. Gcigy. A.G. Swiss Pat.
156,113; C.A. 2_1, 1212 (1933).
69. Black soap and sulphate'black liquor, by E-..ld Pyhala. Mat. Grasses
26, 10,290, 10,317 (Oct. Nov. 1934); C.A. 29, 3831 (1935).
70. Liquid Resin (Tall oil), R. Klatt. Fett chem. UhscCvLL 41, 90 (1934);
C.A. 28, 4901 (1934).
71. The development of different methods for purifying the raw sulphate
rosin soap, by E. Pyhala, Zell. u. Papier 14, (7):273 (July 1934);
Abs. Paper Trade J. 101, (7):45 (Aug. 15, 1935).


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72. Thu quantity of liquid rosin obtained in sulphate cookinC vs. resinic
acid and fatty content of the wood, by H. Borgstr'om and K. Coderquist.
Iva 2, 42 (1934); C.A. 28, 4595 (1934), Abs. Paper 7r'i, J. 99 (19):
24o0 (NTov. 8, 1934). -
73 Use of tall oil in soap making. A, LFrnLuv1ch and LT. ?rct'Yakova-
Masloboino T'-irova Delo. 10, (12):39 (1934); C. A. 2;, 8379 (1935).
74. Making soap from wood, by A. Hellstrom, Paper Ind. E, (3): 173 (June 1935).

75. Production of pure byproducts from resin-containing li uors, by E. H.
FrencIh, U. S. Pat. 1,997,171 (April 9, 1935); C.A. 29, 3864 (1935).

76. Refined sulphate black liquor,talloel and process of making the same,
by Torsten Hosselstrom, U. S. Pat. 1,986,815 (Jan. 8, 1935); C.A.
2_, 1249 (1935).

77. The raw material problem of the Gerra.-n soap inddastry, by R. Krin's.
Seifensieder-Ztg. 62, 115 (1935); C.A. 29, 3185 (1935).
78. Use of liquid resin (tall oil) in soap making, by KIuptschvisku and
A. Yasnui. Maslob. Zhir. Delo. 11, 492 (1935); B.O.A. 585; (1937B)
C.A. 30, 893 (1936).
79. Use of the waste from rosin soap preparation in the paper industry,
by P.D. Sotov, Bumazhnaya Prom. 14j, (9):45, (Sept. 1935).
90. Water soluble resinate production, by E. H. French. U.S. Pat.
2,012,125 (August 20, 1935); C.A. 2, 6782 (1935).
81. A new method for refining tall oil II, by R. H. .;cKee and H. L.
Bleugsli, Paper Trade J. 103, (14):33 (Oct. 1, 1936); C.A. 30
(8613) (1936).
II
82. Dehydrogenation of liquid resin, by H. 0. V. Bergstrom and K. M.
Cederquist. Swed. Pat. 86,321; C.A. Q, 8666 (1936).
83. Historical development of the tall oil industry I, by R. H. McXoe and
H. L. Bleugsli. Paper Trade J. l0p, (12):34 (Sept. 17, 1936); C.A.
30, 8613 (1936).
84. Phthalic acid glycerol tall oil resins, by F. Kalke. Farbcn-Ztg.
42, 942 (Sept. 18, 1936); C.A. _, 3308 (1937).
85. Recovery of waste products at the Lobov Salormbal'sk sulphate pulp mill,
by G. S. Xovalevich. Bumazhnaya Prom. 1, ITo. 10, 20 (Oct. 1936);
C.A. 31, 2422 (1937); Abs. Paper Tr..--, J. 105, (21):3S (Nov. 18,
1937.)
86. Tall oil as a varnish natcrial, by H. Reinert, Farbe u. Lack. 461
(1936); C.A. ., 5603 (1937)-


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87. Tall oil, by R. Yussteig. Mat. grasses 2_8:1076-10769 (1936).
88. Tall oil fat acids. Fr. Kolke. F-.rbn-Ztg. 41:1186 (1936); C.A. 3:
3308 (1937); Paper TrLd J. j 106 (4):36, T.S. 32 (Jan. 27, 1938).
89. Tall oil liquid rosin, by C. Becher. Che:i.-Ztg. 60, Jo. 37, 373
(May 6, 1936); Abs. Paper Tra..c J. l01, (15):40 (Oct. 8, 1936).
90. Uses of tall oil. Tech. Bull- Paper Makers Assoc. Gt Britain and
Ireland l_ (S):109 (August 1936); Abs. Paper Trade J. 103 (23):44
(Dec. 3, 1936).
91. Einrichtung zum v'.r'io'.'n zweier teile von 7egenstanden, by Georg
Hossenfelder. Berlin, Karl Lenck (1937).
92. Fatty acids from pine wood, by J. A. Wallach, Soap 1,3 (3):31-33, 73
(1937); C.A. L1, 3313 (1937); Abs. Paper Trtdo J. l06(4):36 (Jan.
27, 1938).
93. Liquid rosin is beinr produced in greater quantities in Europe.
Naval Stores Rev. CJ_, (5):1 0(May 1, 1937)-
94. Manufacture of sized papers. Oscar F. :T2itzkc (Bennctt, Inc).
U.S. Pat. 2,093,337 (Sept. 14, 1937); Abs. Paper Trade J. 106 (9):
28, T.S. 154 (Ofarch 3, 1938).
95. Occurrence of resin acids in black liquor and wash water, by
Borgstrou, Hilding, and Cederqiaist. Svonsk Pappers-Tidn. 40
(5):112 (March 15, 1937); C.A. ,1 4114 (1937); 3. I. P. C. 1:295;
Abs. P-:pur Trade J. 106 (4):36 (Jan. 27, 1938).
96. Pine st uips to fine chemicals, by R. C. Palmn'.r. DuPont Mag. 31
(4):18-20, 24, (April 1937).
97. Tall oil fat acids with regard to chemistry and paint technology by
H. Holler. Fotte u. Seifon 44, 486 (1937); C.A. 32, 1121 (1938);
Abs. Papeor Trade J. 106 (21):-57 (May 26, 1938).
98. Tall oil fat acids with regard to chemistry and technolo--, by
H. 17iLsen. Fotte u. Seifen 44, 426 (1937); C.A. L, 1121 (1938);
Abs. Paper rade J. 106 (21)Tl (.- 26, 1938).


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LIQUID ROSI:: (TALL-OIL)


Manufacture

Liquid rosin is a byproduct obtained in the ,anufacture of sulphate
pulp from pi:ne (pine =- "tall" in Sweclish), hence the name "Tall-Oil" that is
often uscd in as a commercial term. A soap is separated from the ;.''.ste
liquor and the liquid rosin is obtained from the soap thr-;.:h precipitation
with sulphuric acid or sodium bi-sulphate solution.


Constituents

The composition of liquid rosin is not constant due to variations
in the contents of resinous and fatty acids in the wood. Ordinary liquid
rosin usually tests as follows:
Percent
Water....................... 0.5 2.0
Unsaponifiable matter ...... 8.0 -11.0
Resinous acids .............. 55.0 -45*0
Fatty acids................ 45.0 -55.0

Usually it is sold as about 90 percent saponifiable.

Liquid rosin is a dark-brown and thickish oil, at times soer.1what
cloudy and at times nith a sodi. unt of small crystals of resin. Due to
certain sulphurous r;aters it h-s a characteristic s-ioell.


Purification

The smell can be improved to a high dx:rL:c through treatment with
oxidating agents or through partial -hydration.

Usually the rosin is, however, purified through distillation in
v-cuumr wi-th or without stca-. It is then divided into the following fractions:

Abt. Percent
IP Ll-oil.......... ... ..... .-.. -. 5
Fatty acids (refined tall-oil).. 45
Solid rosin..................... 20
Pitch .................... ....... 30

The quantities of these distillation products, as oell as the
quality, vary according to the cemocsition of the crude rosin and the manner
in which the distillation has been carried out.


RI 129









The products obt-;in..d by distilling crude ro:i. hve all found
their uses.

Th], refined tall-oil (fatty acids) is the most valuable part.
This product still contains some resinous acids but it consists :rini.ily of
fatty acids such as .almitic, oleic and linoleic acid. The refined tall-oil
is light-yclluw in color and is free from di-agre able smell. It is used in
the manuf-ict-ire of ha!ird and. soft soap. It can be transferred into solid
fatty acids by hydration and can be 'used to substitute more expensive
vegetable and u: Xin.- fats. An oil of linseed oil type can be produced tIzro'ih
esterifica.tion with g]yc rine. After a sickative is added it ai]l dry easily
.and can be used a-s a substitute for linseed oil in the manufacture of varnish.
Such esterifiod tall-oil is for sale in Germany.

The rosin obtained through distillation comes in crystalline form
but can be tr-uds,'erred into an aLnorf state by smelting. It is voxr similar
to ordinary colophonium, but the melting point is somewhat higher. It can
be used to advart,_,ge in the manufacture of rosin-size, especially according
to the Dclthlirna method.

The pitch obtained by distillation varies in composition depending
upon the point to which the distillation has been carried out. It has found
many usce such as for lac-varnish and in the manui:acturo of printers' ink.
It is also used as a substitute for asphalt in road building and for similar
purposes.

Liquid rosin is used without purification for several purposes,
such as asphalt c.: .Isions for road building. Other uses for liquid rosin,
as well as for the distillation products, are as oil for moulding cores,
bore-oil and disinfectants, also for impregnation and in the manufacture of
washing soap for sheep and cattle.

A very valuable ingredient of liquid rosin (2-3 percent) is
phytosterine, an alcoholic compound. of high molecular wcig;ht, which g n:: rally
is found in animal and vegetable fats. Phytosterine can be obtain.ed in
crystalline form and is an extremely good agent for em-.ilgation of vaseline,
grease etc., so it ought to find a considerable use for medicinal and
cosmetic purposes as well as in the manufacturer of marina oil. T.he
possibility of -.sing r'hytostorine, in a purified state, in the manufacture
of vitamine and hormone pr.-p _-rations is not precluded.

-Swedish Wood Pulp Journal,
December 31, 1937.


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