# US 8,772,517 B2 · Method of producing a product based on vegetable oil > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,772,517 B2 - Document ID: US8772517B2 - Status: Granted - Kind: B2 - Application number: 12/937,249 - Filed: 2009-04-14 - Published: 2011-04-21 - Granted: 2014-07-08 - Earliest claimed: 2008-04-10 - Assignees: Neste Oil Oyj - Applicants: Kosti Mokkila - Inventors: Kosti Mokkila - Web page: https://patentgrep.com/patent/US8772517B2 ## CPC - C07C 41/26: by introduction of hydroxy or O-metal groups - C07C 37/0555: {being esterified hydroxy groups} - C07C 43/23: containing hydroxy or O-metal groups - C07C 69/58: Esters of straight chain acids with eighteen carbon atoms in the acid moiety - C07C 69/587: Monocarboxylic acid esters having at least two carbon-to-carbon double bonds - C07C 69/753: of polycyclic acids - C11B 13/005: {of residues of the fabrication of wood-cellulose (in particular tall-oil)} - C11C 3/003: {by esterification of fatty acids with alcohols (C11C3/02 takes precedence)} - C07C 2603/26: Phenanthrenes; Hydrogenated phenanthrenes - Y02W 30/74: Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - 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 (drying-oils C09F) - C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM - Y02W: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT ## Abstract A composition, which is suitable for the production of stilbene compounds, can be separated from tall oil. It contains esters of pinosylvin or pinosylvin derivatives and it is concentrated in relation to these. Preferably, the composition contains esters of pinosylvin monomethyl ethers, the acid part of which is formed of an inorganic acid or an organic acid, in particular an organic acid, which is present in the crude tall oil or which is generated from this oil during the process of refining it. Typically, such acids are fatty and resin acids and lower alkane acids. With the invention, it is possible to generate, at an industrial scale, product fractions, and the pinosylvin compounds which are separated from the fractions can be used as such or they can be further modified by means of different chemical methods. ## Claims ### Claim 1 A composition suitable for manufacturing stilbene compounds, which comprises esters of pinosylvin and that it is enriched in relation to these, wherein the acid part of said esters is derived from linoleic acid, linolenic acid, oleic acid, or a tricyclic, aliphatic or aromatic carboxylic acid. ### Claim 2 (depends on 1) The composition according to claim 1, wherein the ester percentage of the pinosylvin in the composition is at least approximately 3 weight-%, calculated from the total weight of the composition. ### Claim 3 (depends on 1) The composition according to claim 1, wherein said acid part is derived from linoleic acid, linolenic acid or oleic acid. ### Claim 4 (depends on 1) The composition according to claim 1, wherein said acid part of the esters is derived from a tricyclic, aliphatic or aromatic carboxylic acid. ### Claim 5 (depends on 4) The composition according to claim 4, wherein said acid part is derived from abietic acid, dehydroabietic acid, neoabietic acid, palustrene acid, pimaric acid or levopimaric acid. ### Claim 6 (depends on 1) The composition according to claim 1, wherein the concentration of the dry matter or of the pinosylvin of the composition is approximately 3-50 weight-%. ### Claim 7 (depends on 6) The composition according to claim 6, wherein the concentration of the ester of the pinosylvin is approximately 5-95 weight-%. ### Claim 8 (depends on 1) The composition according to claim 1, which comprises a fraction of the distillation or evaporation of crude tall oil, which fraction has been enriched in order to increase the portion of pinosylvin or of the esters of its derivatives. ### Claim 9 (depends on 1) The composition according to claim 1, which comprises tall oil pitch, which has been concentrated in order to increase the portion of pinosylvin or esters of its derivatives. ### Claim 10 (depends on 1) The composition according to claim 1, wherein the portion of esters of pinosylvin, or a mixture of two or more of the compounds, is approximately 1-95 weight-%. ### Claim 11 A method of producing a composition suitable for manufacturing pinosylvin and its compounds, said method comprises recovering a fraction of the distillation or evaporation of crude tall oil as the overhead product of a column or of an evapopration used in the distillation of tall oil, wherein said fraction contains esters of pinosylvin or its derivatives, which fraction is then enriched in relation to the esters of pinosylvin or its derivatives and wherein stilbene compounds, which form part of the overhead product, are esterified with lower alkane acids or fatty acids or resin acids, or the stilbene compounds are modified by means of chemical technology methods to form compounds that are easier to separate from the rest of the fraction then is the original compound. ### Claim 12 (depends on 11) The method according to claim 11, wherein the feeding flow of the distillation or the evaporation is a fraction, which is the overhead product, the bottoms product or a side draw-off taken from a chosen intersection, of a distillation column or an evaporator of the tall oil distillery. ### Claim 13 (depends on 11, 12) The method according to claim 11 or 12, wherein a fraction, which contains esters of pinosylvin or its derivatives, is recovered as the bottoms fraction of the fatty acid distillation column. ### Claim 14 (depends on 11, 12) The method according to claim 11 or 12, wherein said fraction, which contains esters of pinosylvin or its compounds, is tall oil pitch. ### Claim 15 (depends on 11) The method according to claim 11, wherein any overhead product of the tall oil distillery or other product flow is concentrated in relation to stilbene or its compounds, after the esterification of said compounds. ### Claim 16 (depends on 11) The method according to claim 11, wherein a composition suitable for the manufacturing of stilbene compounds is formed by combining the bottoms fraction of the fatty acid distillation column and the overhead product of the distillation of the light fatty acids. ### Claim 17 (depends on 11) The method according to claim 11, wherein in order to improve the ester yield from the stilbene compounds, the crude tall oil or one of its distillation fractions is brought to such conditions which facilitate the generation of esters, through a reaction between pinosylvin or pinosylvin monomethyl ether and fatty acids or resin acids. ### Claim 18 (depends on 17) The method according to claim 17, wherein crude tall oil or its distillation fraction is contacted with an additive which catalyzes the esterification. ### Claim 19 (depends on 18) The method according to claim 18, wherein oxygen is used as the additive which catalyzes the esterification. ### Claim 20 (depends on 18, 19) The method according to claim 18 or 19, wherein a compound, which discharges hydrogen ions when it reacts with fatty or resin acids, is used as the additive which catalyzes the esterification. ### Claim 21 A resin acid ester of pinosylvin or of us monomethyl ether wherein the acid part is derived from abietic acid, dehydroabietic acid, neoabietic acid, palustrene acid, pimaric acid or levopimaric acid. ### Claim 22 (depends on 2) The composition according to claim 2, wherein said ester percentage is approximately 3-80 weight-%. ### Claim 23 (depends on 2) The composition according to claim 2, wherein said ester percentage is approximately 5-50 weight-%. ### Claim 24 (depends on 7) The composition according to claim 7, wherein said concentration of the ester is approximately 10-60 weight-%. ### Claim 25 (depends on 7) The composition according to claim 7, wherein said concentration of the ester is approximately 15-50 weight-%. ### Claim 26 (depends on 10) The composition according to claim 10, wherein said portion is approximately 10-60 weight-%. ### Claim 27 (depends on 10) The composition according to claim 10, wherein said portion is approximately 15-50 weight-%. ### Claim 28 A composition suitable for manufacturing stilbene compounds, which comprises 5 to 95 weight % of esters of pinosylvin, wherein the acid part of said esters is derived from linoleic acid, linolenic acid, oleic acid, or a tricyclic, aliphatic or aromatic carboxylic acid. ### Claim 29 (depends on 21) The composition according to claim 21, wherein said acid part is derived from linoleic acid, linolenic acid or oleic acid.