US3926936A - Process for manufacturing valuable products from tall oil pitch - Google Patents

Process for manufacturing valuable products from tall oil pitch Download PDF

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Publication number
US3926936A
US3926936A US41610173A US3926936A US 3926936 A US3926936 A US 3926936A US 41610173 A US41610173 A US 41610173A US 3926936 A US3926936 A US 3926936A
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United States
Prior art keywords
pitch
tall oil
process according
oil
distillate
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English (en)
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Timo Pellervo Lehtinen
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OULO OSAKEYHTIO
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OULO OSAKEYHTIO
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
    • C11B13/005—Recovery of fats, fatty oils or fatty acids from waste materials of residues of the fabrication of wood-cellulose (in particular tall-oil)
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes

Definitions

  • the present invention relates to a process of the character once described, which comprises heating of the tall oil pitch at a temperature of 200300C together with a-basic reagent, the base rate being 5-25 of the amount of pitch, acidifying the reaction product thereby obtained into oil having an acid value of 50-l50, distilling the obtained oil under a pressure of less than 50 mm Hg to get, a distillate, 10-70 of which the acid value is ,100-190 and which can be refined further by the previously known fraction distillation process under a lowered pressure, and a distillation residue of which the softening point (ball and ring) is not lower than 50C.
  • the oil pitch may be heated with the alkali reagent either as such or in a solvent.
  • the oil obtained after acidifying may be distilled either as such or after the removal of the salt produced in the acidification.
  • Acid value 150-160 saponification value 155-165 Rosin acids, L. 30-50 Unsaponifiables;-% l0-20 Color, Gardner l0-l2 The invention is based on the observation that the difference between the saponification and acid values of tall oil pitch is considerably high. This difference, which is also called the ester number, is illustrated in the following table, for which quality samples of the pitch produced by three European tall oil distilleries have been selected arbitrarily:
  • a B C Acid value 35 40 3O saponification value 95 Ester number 55 60 65 The real incentive for this invention was, however, given by the observation that when the saponification of tall oil pitch is carried out under very drastic conditions, for example, by treating pitch with alkali 10-15 for 2 hours at 230C, strongly bonded acids on which a mild or moderately drastic saponification, such as is used, for example, in determining the saponification value, has no noteworthy effect, takes place to a surprisingly great extent. As a result of the said rigorous treatment, acids are released to such an extent that the real saponification value of pitch rises to about -140.
  • Rosin acid anhydrides are created as the first intermediates under the influence of high temperature when dehydration takes place, and these rosin acid anhydrides for their part react very easily with alcohols so that one half of an anhydride becomes esterified with the alcohol in question, while the other half is released as rosin acid:
  • An advantageous temperature for the saponification of pitch is 220250C. At temperatures lower than this the saponification remains incomplete and, furthermore, the viscosity of the pitch soap is so great that mixing becomes difficult and is almost impossible at temperatures under 200C. At temperatures above 250C. saponification is accelerated, but the decarboxylation and splitting reactions of the acids are simultaneously fortified.
  • the requisite amount of alkali depends to some extent on the quality of the pitch and is usually -15 of the amount of pitch.
  • the alkali can be added either as such or as a 50 water solution, for example.
  • the addition can already be started, when so desired, at a temperature of 100-1S0C As the addition progresses, the temperature of the pitch is raised so much that increased viscosity will not disturb the mixing.
  • the alkali can just as well be added at the reaction temperature, e.g., 230C. Adding the alkali as a water-free powder isadvantageous because foaming does not then take place nearly as much as when using a water solution of the alkali.
  • the acidification of the produced pitch soap in order to release the fatty and rosin acids, can take place either while the soap is hot or by cooling the soap and dissolving it as granules in hot water for acidification.
  • the pitch soap immediately after the saponification reaction it is preferable to cool the pitch soap immediately after the saponification reaction to a temperature at which mixing is just barely possible, i.e., usually to about 200C.
  • the acidification can be carried out with, for example, a 30-50 sulfuric acid solution.
  • the viscosity of the reaction mixture begins to lower sharply after even a small acid addition and, consequently, the temperature can be lowered during the acidification so that at the end of the acidification it may be 150C, for example.
  • the temperature lowers, removing water by evaporation is complicated, for which reason it is preferable to use vacuum drying at the end.
  • excess sulfuric acid causes corrosion problems and, on the other hand, it catalyzes the reesterification of the released acids.
  • a third possibility is to achieve the alkali treatment of pitch in a suitable solvent, e.g., diethylene glycol, in which case the temperature of the reaction mixture can be lowered to below 100C before beginning the acidification, without the viscosity preventing it.
  • a suitable solvent e.g., diethylene glycol
  • the rest of the process according to this invention can be arranged in its simplest form so that the oil obtained by acidification after the alkali treatment and which contains the alkali salt produced in the acidification is distilled over by a rapid vacuum distillation (e.g., 1-5 mm Hg), in which case the distillate yield is 30-40 the bottom temperature rising to about 300C.
  • a rapid vacuum distillation e.g. 1-5 mm Hg
  • the yield of a distillate which has a neutral substance content of about 50 e.g., hydrocarbons produced from sterols by dehydration is still about 10
  • the alkali salt remains in the distillation residue, from which it can, when so desired, be regenerated by, for example, burning, which is possible in, for example, sulfate cellulose plants.
  • the alkali salt can be removed before distillation, in which case the hard pitch obtained as a distillation residue is ash-free.
  • the hard pitch obtained as a distillation residue is ash-free.
  • most of the solid, crystalline Na SO can be removed from dried oil by decantation or centrifugation. Even a water wash of the oil at C removes most of the alkali salt, but owing to the rather great viscosity of the oil, the separation of the layers is slower and less complete than in, for example, the wash of crude tall oil.
  • the most effective method for removing the alkali salt is to dissolve the oil released in the acidification in a suitable solvent with a polarity sufficient for complete dissolving.
  • the alkali can be easily removed by centrifugation, filtration, or a water wash from this low-viscosity solution.
  • the yield of distillate from tall oil pitch is 30-40 in a typical case, and'on the basis of a gravimetric analysis (alkali extraction and selective esterification) this distillate contains fatty acids 35-40 rosin acids 40-50 and neutral substance 12-16
  • the composition of the fatty acid portion is special in that the typical polyunsaturated fatty acids of tall oil (linoleic, cis-5,9,l2- octadecatrienoic, and cis-5,l 1,14-eicosatrienoic acids) have become transformed, under the influence of alkali treatment, almost quantitatively into their isomers with a conjugated diene system.
  • the fatty acid portion contains conjugated diene 30-40 and conjugated triene less than 1
  • the respective rosin acid portion is otherwise conventional except that the abietic/dehydroabietic acid ratio is lower than 1, while in a normal tall oil rosin it is usually higher than 1.
  • the neutral substance contains two main groups which are very distinct in a temperature programmed gaschromatographic analysis (SE 30 column).
  • One group comprises the hydrocarbons produced as a result of the decarboxylation of the acids and the other decomposition products with low boiling points.
  • the other group comprises the hydrocarbons produced as dehydration products from the sterols released from sterol esters. Obviously dehydration of sterols takes place both during the alkali treatment and during the acidification stage, for sulfuric acid is mentioned as an effective dehydration catalyst of secondary alcohols at 200C.
  • the main component of these hydrocarbons is the A -diene C l-I produced from B-sitosterol and which is interesting even technologically owing to its conjugated diene structure, because by, for example, the Diels-Alder reaction it can be bonded with maleic anhydride or fumaric acid, in which case the obtained product is a usable additive in, for example, paper size.
  • the process which can be mainly considered for further refinement of the distillate is fractionating distillation at a lowered pressure. This can be carried out either as a completely separate line, in which case the th it h was i d to 150C A amount 6f 15 g f special characteristics of the obtained fatty acid and N OH as a 50 water l i was dd d to h i h rosin can be utilized, or alternatively the pitch distillate hil l i h temperature to rise to 200 during can be fed into the distillation of normal tall oil, either th additi Th temperature was i d to 230C d into the crude tall oil or the distillate after the pitch mixing was continued for 2 hours. The temperature of column.
  • lfthe rosin is also taken as a distillate, a considerable proportion of the hydrocarbons in question in gggjgfifvm 52 33 the distillation residue.
  • Acid value 163 80 In addition to the described distillate suitable for 323123;; value 2g 38 further refining, another, interesting product is ob Unsaponifiables,% 16 46 tained simultaneously from tall oil pitch, namely, hard l1 18 pitch produced as a distillation residue. In a typical case the proporties of this product are as follows:
  • Fraction l represents a very high-standard product suitable for further refinement.
  • the temperature Acid fl 1 at the bottom rose above 300C, a great amount of Saponification value 60-90 softening point r 30 neutral substance was distilled over, as indicated by the (bail and ring), "C 60- 0 analysis of Fraction 2. Ash, 0-2
  • The'acid value of the tall oil pitch used in the follow- 60 ing examples was 39 and its saponification value 96.
  • the rosin acid content was determined by g ff l l" 94 the Linder-Persson method, the softening point by the Alt i point ac ifs ball and ring method, and the color in Gardner units.
  • EXAMPLE 1 EXAMPLE 3 l00 g of tall oil pitch was placed in a flask provided The saponification and the acidification of tall oil with a mixer and a thermometer. The temperature of pitch wa carried ut in h same way as in Example 2 7 except that the 2-hour hot saponification took place at a lower temperature, 200C. overdistillation was not carried out because the acid value of the obtained oil was only 72, its saponification value 99, and its rosin acid content 20 This indicates that the saponification conditions used were too mild.
  • EXAMPLE 6 100 g of tall oil pitch, 100 ml of diethylene glycol, and g of NaOH was placed in reaction flask provided with a mixer and a thermometer. The temperature of the mixture was raised to 230C and mixing was continued for 2 hours. The reaction mixture was cooled to 90C and the pitch soap was acidified with a 30 H solution. The glycol was washed away with water. The acid value of the obtained oil was 96.
  • EXAMPLE 7 2500 g of tall oil pitch was placed in a 5 1 reaction flask provided with a mixer and a thermometer. The temperature of ,the pitch was raised to 230C, and 250 g of powdered NaOH was added to the pitch in the course of about half an hour. Mixing was continued for 2 hours at 230C. The reaction mixture at 230C was poured into an aluminium foil mold and allowed to cool. The cooled, hard pitch soap was crushed into pieces and dissolved in about 5 l of water. The dissolution took place easily when heated. The obtained soap solution was acidified with a 30 H 80 solution and the produced oil was washed with water (3 times 2 liters). The acid value of the obtained oil was 104 and its ash content 5 so that the washing of Na SO had not been nearly complete. The yield of the overdistillation was 35 and its analysis as follows:
  • the pitch soap solution was acidified with an equivalent amount of a 30 sulfuric acid.
  • the NaSO -containing water layer and the oil produced in the acidification became easily and sharply separated from each other at 90C.
  • About 90 of the Na SO produced in the acidification ended up in the water layer.
  • the xylene was removed from the oil by an overdistillation carried out under a pressure of about 100 mm Hg. At the same time the oil was obtained completely water-free since the remanent water was distilled together with the xylene.
  • the analysis of the obtained oil was as follows:
  • the oil was fed into a continuous-working distillation column.
  • the feeding rate varied within the range of 40-70 kg/h.
  • the pressure at the top of the column was 2-4 mm Hg and at the bottom 5-7 mm Hg.
  • a process for the manufacture of products from tall oil pitch produced in the distillation of tall oil comprising:
  • a. saponifying tall oil pitch by heating it at a temperature in the range 200-300C. together with an alkali saponification agent, the amount of said agent comprising 525% of the amount of pitch until a main portion of the sterols liberated from fatty and rosin acid esters have been converted to hydrocarbons by dehydration,
  • a process according to claim 1 wherein the saponification is conducted by heating said tall oil pitch together with said saponification agent in the presence of a solvent for said tall oil pitch.
  • step (a) the amount of said saponification agent is 720% and said temperature is in the range 230280C.
  • step (b) the saponified pitch soap melt is directed into water to obtain a pitch soap solution which is acidified into oil;
  • step (b) the alkali salt produced in the acidification is removed by a water wash prior to step (c).

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Working-Up Tar And Pitch (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US41610173 1972-11-17 1973-11-15 Process for manufacturing valuable products from tall oil pitch Expired - Lifetime US3926936A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FI323772A FI49708C (fi) 1972-11-17 1972-11-17 Menetelmä arvotuotteiden valmistamiseksi mäntypiestä.

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US3926936A true US3926936A (en) 1975-12-16

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US (1) US3926936A (enrdf_load_stackoverflow)
JP (1) JPS5726319B2 (enrdf_load_stackoverflow)
AT (1) AT330925B (enrdf_load_stackoverflow)
DE (1) DE2356576B2 (enrdf_load_stackoverflow)
FI (1) FI49708C (enrdf_load_stackoverflow)
FR (1) FR2207185B1 (enrdf_load_stackoverflow)
GB (1) GB1432853A (enrdf_load_stackoverflow)
IT (1) IT1003227B (enrdf_load_stackoverflow)
NL (1) NL175432C (enrdf_load_stackoverflow)
NO (1) NO140799C (enrdf_load_stackoverflow)
PL (1) PL87655B1 (enrdf_load_stackoverflow)
SE (1) SE383527C (enrdf_load_stackoverflow)
SU (1) SU587871A3 (enrdf_load_stackoverflow)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4272419A (en) * 1978-11-20 1981-06-09 Westvaco Corporation Treatment of styrene-butadiene rubber
US5097012A (en) * 1990-01-23 1992-03-17 Clemson University Solvent extraction of fatty acid stream with liquid water and elevated temperatures and pressures
US6107456A (en) * 1998-08-31 2000-08-22 Arizona Chemical Corporation Method for separating sterols from tall oil
US20040195886A1 (en) * 2003-04-07 2004-10-07 Beatty George T. Rotation lock mechanism for aircraft seat
EP1586624A1 (en) * 2004-02-06 2005-10-19 Härting Glade, Thomas Francis Process of refinement of crude tall oil using short path distillation
US20070256594A1 (en) * 2006-03-01 2007-11-08 Andriessen Marcel J Release Agents Containing Saponified Fatty and Rosin Acids or Derivatives Thereof
WO2008099051A3 (en) * 2007-02-15 2008-10-09 Ravintoraisio Oy Process for isolation of fatty acids, resin acids and sterols from tall oil pitch
US20110049012A1 (en) * 2008-04-21 2011-03-03 Lars Stigsson Conversion of crude tall oil to renewable feedstock for diesel range fuel compositions
US20120117879A1 (en) * 2010-11-16 2012-05-17 Vapo Oy Method for utilizing distillation fractions obtained from distillation of tall oil in btl or cellulose factory
US20150164966A1 (en) * 2012-05-14 2015-06-18 Hankkija Oy Saponified tall oil fatty acid for use in treatment and animal feed supplements and compositions
US9789143B2 (en) 2013-05-14 2017-10-17 Hankkija Oy Use of tall oil fatty acid
US9962353B2 (en) 2013-10-24 2018-05-08 Hankkija Oy Use of tall oil fatty acid in binding toxins
WO2019103684A1 (en) * 2017-11-21 2019-05-31 Sunpine Ab Method for thermal treatment of tall oil pitch (top)
WO2019228602A1 (en) * 2018-06-01 2019-12-05 Raisio Nutrition Ltd Process for isolation of sterols and a fraction rich in fatty acids and resin acids
US10799544B2 (en) 2013-11-13 2020-10-13 Hankkija Oy Feed supplement and a feed composition comprising resin acid based composition
US10945939B2 (en) 2017-02-15 2021-03-16 Yokozeki Oil & Fat Industries Co., Ltd. Oil composition, production method thereof, oily base and external preparation for skin
US11097981B2 (en) 2016-08-09 2021-08-24 A.L.M. Holding Company Sterol blends as an additive in asphalt binder
US11168214B2 (en) 2016-06-10 2021-11-09 A.L.M. Holding Company Method for identifying the extent of aging in an asphalt
US11427697B2 (en) 2017-07-26 2022-08-30 A.L.M. Holding Company Use of sterols from animal waste as an additive in asphalt binder
US11542668B2 (en) 2017-02-02 2023-01-03 Ergon Asphalt & Emulsions, Inc. Sterol additive in asphalt pavement
US11578234B2 (en) 2019-07-10 2023-02-14 Neste Oyj Process and apparatus for treating tall oil
US11718756B2 (en) 2017-10-20 2023-08-08 A.L.M. Holding Company Asphalt emulsion surface treatment containing sterol

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5887676U (ja) * 1981-12-10 1983-06-14 ヤンマー農機株式会社 田植機
DE3225337C2 (de) * 1982-07-07 1986-10-16 Hermann Dr. 4400 Münster Stage Verfahren zum Entsalzen von Rohtallöl
JPH0293216U (enrdf_load_stackoverflow) * 1988-10-17 1990-07-24

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2138183A (en) * 1936-06-12 1938-11-29 Hercules Powder Co Ltd Process for the treatment of rosins and metal salts produced thereby
US2276517A (en) * 1939-12-16 1942-03-17 Nat Oil Prod Co Treatment of tall oil
US2334762A (en) * 1939-12-11 1943-11-23 Hasselstrom Torsten Stable tall oil product
US2530810A (en) * 1949-08-23 1950-11-21 Pittsburgh Plate Glass Co Separation of unsaponifiable matter from tall oil residue

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2138183A (en) * 1936-06-12 1938-11-29 Hercules Powder Co Ltd Process for the treatment of rosins and metal salts produced thereby
US2334762A (en) * 1939-12-11 1943-11-23 Hasselstrom Torsten Stable tall oil product
US2276517A (en) * 1939-12-16 1942-03-17 Nat Oil Prod Co Treatment of tall oil
US2530810A (en) * 1949-08-23 1950-11-21 Pittsburgh Plate Glass Co Separation of unsaponifiable matter from tall oil residue

Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4272419A (en) * 1978-11-20 1981-06-09 Westvaco Corporation Treatment of styrene-butadiene rubber
US5097012A (en) * 1990-01-23 1992-03-17 Clemson University Solvent extraction of fatty acid stream with liquid water and elevated temperatures and pressures
US6107456A (en) * 1998-08-31 2000-08-22 Arizona Chemical Corporation Method for separating sterols from tall oil
US6414111B2 (en) 1998-08-31 2002-07-02 Arizona Chemical Company Method for separating sterols from tall oil
US20040195886A1 (en) * 2003-04-07 2004-10-07 Beatty George T. Rotation lock mechanism for aircraft seat
EP1586624A1 (en) * 2004-02-06 2005-10-19 Härting Glade, Thomas Francis Process of refinement of crude tall oil using short path distillation
US20070256594A1 (en) * 2006-03-01 2007-11-08 Andriessen Marcel J Release Agents Containing Saponified Fatty and Rosin Acids or Derivatives Thereof
US9422507B2 (en) * 2007-02-15 2016-08-23 Ravintoraisio Oy Process for isolation of fatty acids, resin acids and sterols from tall oil pitch
WO2008099051A3 (en) * 2007-02-15 2008-10-09 Ravintoraisio Oy Process for isolation of fatty acids, resin acids and sterols from tall oil pitch
US8450453B2 (en) 2007-02-15 2013-05-28 Ravintoraisio Oy Process for isolation of fatty acids, resin acids and sterols from tall oil pitch
US20130261284A1 (en) * 2007-02-15 2013-10-03 Ravintoraisio Oy Process for isolation of fatty acids, resin acids and sterols from tall oil pitch
US20100137556A1 (en) * 2007-02-15 2010-06-03 Ravintoraiso Oy Process for isolation of fatty acids, resin acids and sterols from tall oil pitch
US20110049012A1 (en) * 2008-04-21 2011-03-03 Lars Stigsson Conversion of crude tall oil to renewable feedstock for diesel range fuel compositions
US8735637B2 (en) * 2008-04-21 2014-05-27 Sunpine Ab Conversion of crude tall oil to renewable feedstock for diesel range fuel compositions
US20120117879A1 (en) * 2010-11-16 2012-05-17 Vapo Oy Method for utilizing distillation fractions obtained from distillation of tall oil in btl or cellulose factory
US20150164966A1 (en) * 2012-05-14 2015-06-18 Hankkija Oy Saponified tall oil fatty acid for use in treatment and animal feed supplements and compositions
US9789077B2 (en) 2012-05-14 2017-10-17 Hankkija Oy Use of saponified tall oil fatty acid
US9907771B2 (en) 2012-05-14 2018-03-06 Hankkija Oy Saponified tall oil fatty acid for use in treatment and animal feed supplements and compositions
US9789143B2 (en) 2013-05-14 2017-10-17 Hankkija Oy Use of tall oil fatty acid
US9919013B2 (en) 2013-05-14 2018-03-20 Hankkija Oy Use of tall oil fatty acid
US10092610B2 (en) 2013-05-14 2018-10-09 Hankkija Oy Tall oil fatty acid for use in treatment and animal feed supplements and compositions
US9962353B2 (en) 2013-10-24 2018-05-08 Hankkija Oy Use of tall oil fatty acid in binding toxins
US10799544B2 (en) 2013-11-13 2020-10-13 Hankkija Oy Feed supplement and a feed composition comprising resin acid based composition
US10849947B2 (en) 2013-11-13 2020-12-01 Hankkija Oy Feed supplement and a feed composition comprising resin acid based composition
US11253562B2 (en) 2013-11-13 2022-02-22 Forchem Oy Feed supplement
US11168214B2 (en) 2016-06-10 2021-11-09 A.L.M. Holding Company Method for identifying the extent of aging in an asphalt
US11912874B2 (en) 2016-06-10 2024-02-27 A.L.M. Holding Company Crude sterol as an additive in asphalt binder
US11760882B2 (en) 2016-06-10 2023-09-19 A.L.M. Holding Company Method for identifying the extent of aging in an asphalt
US11667570B2 (en) 2016-08-09 2023-06-06 A.L.M. Holding Company Sterol blends as an additive in asphalt binder
US12234189B2 (en) 2016-08-09 2025-02-25 A.L.M. Holding Company Sterol blends as an additive in asphalt binder
US11097981B2 (en) 2016-08-09 2021-08-24 A.L.M. Holding Company Sterol blends as an additive in asphalt binder
US12163294B2 (en) 2017-02-02 2024-12-10 A.I.M. Holding Company Sterol additive in asphalt pavement
US11542668B2 (en) 2017-02-02 2023-01-03 Ergon Asphalt & Emulsions, Inc. Sterol additive in asphalt pavement
US10945939B2 (en) 2017-02-15 2021-03-16 Yokozeki Oil & Fat Industries Co., Ltd. Oil composition, production method thereof, oily base and external preparation for skin
US11427697B2 (en) 2017-07-26 2022-08-30 A.L.M. Holding Company Use of sterols from animal waste as an additive in asphalt binder
US11718756B2 (en) 2017-10-20 2023-08-08 A.L.M. Holding Company Asphalt emulsion surface treatment containing sterol
US12084577B2 (en) 2017-10-20 2024-09-10 A.L.M. Holding Company Asphalt emulsion surface treatment containing sterol
WO2019103684A1 (en) * 2017-11-21 2019-05-31 Sunpine Ab Method for thermal treatment of tall oil pitch (top)
US10988707B2 (en) * 2017-11-21 2021-04-27 Sunpine Ab Method for thermal treatment of tall oil pitch (TOP)
US11370990B2 (en) 2018-06-01 2022-06-28 Raisio Nutrition Ltd Process for isolation of sterols and a fraction rich in fatty acids and resin acids
WO2019228602A1 (en) * 2018-06-01 2019-12-05 Raisio Nutrition Ltd Process for isolation of sterols and a fraction rich in fatty acids and resin acids
US11578234B2 (en) 2019-07-10 2023-02-14 Neste Oyj Process and apparatus for treating tall oil

Also Published As

Publication number Publication date
SE383527B (sv) 1976-03-15
NO140799B (no) 1979-08-06
FR2207185B1 (enrdf_load_stackoverflow) 1977-08-12
SU587871A3 (ru) 1978-01-05
DE2356576A1 (de) 1974-05-22
NO140799C (no) 1979-11-14
GB1432853A (en) 1976-04-22
IT1003227B (it) 1976-06-10
ATA962473A (de) 1975-10-15
PL87655B1 (enrdf_load_stackoverflow) 1976-07-31
DE2356576B2 (de) 1979-11-15
NL175432C (nl) 1984-11-01
JPS5726319B2 (enrdf_load_stackoverflow) 1982-06-03
SE383527C (sv) 1984-10-15
FR2207185A1 (enrdf_load_stackoverflow) 1974-06-14
NL7315842A (enrdf_load_stackoverflow) 1974-05-21
FI49708B (enrdf_load_stackoverflow) 1975-06-02
FI49708C (fi) 1975-09-10
AT330925B (de) 1976-07-26
DE2356576C3 (enrdf_load_stackoverflow) 1980-08-07
JPS49133313A (enrdf_load_stackoverflow) 1974-12-21

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