New low sulfur terpene mix recovery from wood processing

Patent metadata

Field	Value
Publication number	US-2025290009-A1
Application number	US-202318861193-A
Country	US
Kind code	A1
Filing date	May 8, 2023
Priority date	May 9, 2022
Publication date	Sep 18, 2025
Grant date	—

Abstract

Disclosed herein is an eco-friendly liquid wood extract including terpenic compounds. Also disclosed herein is a perfumery, cosmetic, pharmaceutic, nutraceutical, antimicrobial, agrochemical or chemical ingredient obtained by the use the eco-friendly liquid wood extract. Also disclosed herein is a process for preparing an eco-friendly liquid wood extract.

First claim

1 . A liquid wood extract comprising:
a) between 50 and 95% (wt %) of at least one non-oxygenated monoterpene, b) between 5 and 30% (wt %) of at least one terpene of higher molecular-weight than non-oxygenated monoterpenes, c) less than 0.1% (wt %) of at least one wood biomass thermal degradation compound, and d) a sulfur content of less than 1000 ppm.

2 . The liquid wood extract according to claim 1 , wherein said at least one terpene of higher molecular-weight than non-oxygenated monoterpenes has a molecular-weight of more than 140 g/mol and/or is selected from the group consisting of oxygenated monoterpenes, diterpenes, sesquiterpenes, and mixtures thereof.

3 . The liquid wood extract according to claim 1 , wherein said at least one terpene of higher molecular-weight than non-oxygenated monoterpenes is at least one oxygenated monoterpene selected from the group consisting of monoterpenes alcohols, monoterpene epoxides, and mixtures thereof and/or at least one diterpene selected from the group consisting of a dicyclic diterpene, a tricyclic diterpene, and mixtures thereof.

4 . The liquid wood extract according to claim 1 , wherein said at least one terpene of higher molecular-weight than non-oxygenated monoterpenes is at least one sesquiterpene selected from the group consisting of acyclic sesquiterpene, cyclic sesquiterpene, and mixtures thereof.

5 . The liquid wood extract according to claim 1 , wherein said at least one non-oxygenated monoterpene is selected from the group consisting of a bicyclic non-oxygenated monoterpene, a monocyclic non-oxygenated monoterpene, an acyclic non-oxygenated monoterpene, and mixtures thereof.

6 . The liquid wood extract according to claim 1 , wherein said at least one non-oxygenated monoterpene is
at least one bicyclic non-oxygenated monoterpene selected from the group consisting of α-Pinene, β-Pinene, Camphene, delta-3-Carene, bornylene, sabinene, thujene, Carane, each being in the form of any one of their stereoisomers, and a mixture thereof; and/or at least one acyclic non-oxygenated monoterpene selected from the group consisting of Myrcene, ocimene, allo-ocimene, Citronellene, each being in the form of any one of their stereoisomers, and a mixture thereof; and/or at least one monocyclic non-oxygenated monoterpene selected from the group consisting of Limonene, Dipentene, Isolimonene, p-Menthane, 1-p-Menthene, 3-p-Menthene, α-Terpinene, γ-Terpinene, Terpinolene, α-Phellandrene, β-phellandrene, p-Cymene, each being in the form each in the form of any one of their stereoisomers, and a mixture thereof.

7 . The liquid wood extract according to claim 1 , wherein said at least one wood biomass thermal degradation compound is any of:
at least one cellulose-derived decomposition product selected from the group consisting of hydroxymethyl furfural, levoglucosan, cellobiose, anhydroglucose derivatives, acetaldehyde, methanol, glyoxal, acrolein, each being in the form of any one of their stereoisomers, and a mixture thereof, and/or at least one hemicellulose-derived decomposition product selected from the group consisting of furan, furan derivatives, furfuraldehyde, and furfuryl alcohol, and/or at least one lignin-derived decomposition product selected from the group consisting of phenol, phenol derivatives, cresol, catechol, eugenol, methyleugenol, guaiacol, 4-propylphenol, 4-ethylguaiacol, syringol, p-hydroxyphenolic hydroxy methoxy toluene, hydroxy methoxy ethyl benzene, hydroxy methoxyvinyl benzene, hydroxy methoxy propyl benzene, dimethoxy phenol, hydroxy dimethoxy toluene, hydroxy dimethoxy ethyl benzene, hydroxy dimethoxy propyl benzene, pyrocatechol, benzofuran, dibenzofuran, vanillin, each being in the form of any one of their stereoisomers, and a mixture thereof, and/or a mixture thereof.

8 . The liquid wood extract according to claim 1 , comprising:
less than 0.05% (wt %) of at least one wood biomass thermal degradation compound; and/or a sulfur content of less than 200 ppm; and/or 5 and 20% (wt %) of at least one terpene of higher molecular-weight than non-oxygenated monoterpenes

9 . The liquid wood extract according to claim 1 , wherein said at least one oxygenated monoterpene is at least one monocyclic monoterpene alcohol.

10 . A process for producing a liquid wood extract comprising:
a. providing wood logs mix comprising hardwood and softwood, with more than 50% of softwood, b. cutting or chipping or shredding the wood logs in strands or chips, c. applying a first steam treatment on the wood strands or chips in such a way that the steam is passed over the wood stands or chips at a temperature between 50° C. and 120° C. and at a pressure between 0.1×105 Pa and 4×105 Pa, d. applying a first compression step of the wood strands or chips at a pressure of between 7×105 Pa and 15×105 Pa and by adding water to the wood strands or chips at a temperature of between 10 to 40° C., to obtain pre-softened wood strands or chips and to collect a first compression extract, e applying an evaporation step to the first compression extract by evaporating more than 15% of the first compression extract to generate a steam enriched in terpenic compounds, f. condensing the steam enriched in terpenic compounds, optionally combined with steam collected from the first steam treatment process, to obtain a condensed phase, and g. applying a separation phase to said condensed phase by treating the condensed phase preferably by gravimetry decantation and/or centrifugation to obtain a liquid wood extract.

11 . The process according to claim 10 wherein the process further comprises:
second steam treatment that is applied to the pre-softened wood strands or chips in such a way that the steam is passed over the pre-softened wood strands or chips at a temperature between 150° C. and 220° C., at a pressure between 7×105 Pa and 17×105 Pa, and
a second compression step applied following the second steam treatment at a pressure of between 7×105 Pa and 15×105 Pa to obtain softened wood strands or chips and to collect a second compression extract.

12 . The process according to claim 10 wherein said process further comprises a refining step applied by passing a steam over the pre-softened wood stands or chips or over the softened wood stands or chips at a temperature between 150° C. and 220° C., at a pressure between 7×105 Pa and 15×105 Pa.

13 . The process according to claim 11 wherein said condensed phase also comprises the steam collected from the second steam treatment and/or the refining step.

14 . A process for obtaining a perfumery, cosmetic, pharmaceutic, nutraceutical, antimicrobial agrochemical and/or chemical ingredient comprising the step of obtaining the liquid wood extract according to the process of claim 10 .

15 . A method of using the liquid wood extract according to claim 1 , the method comprising using the liquid wood extract as an active compound in perfumery, cosmetic, pharmaceutic, nutraceutical, antimicrobial, agrochemical and/or chemical compositions or for obtaining an active compound for a perfumery, cosmetic, pharmaceutic, nutraceutical, antimicrobial, agrochemical or chemical composition.

16 . The liquid wood extract according to claim 1 , wherein said at least one terpene of higher molecular-weight than non-oxygenated monoterpenes is at least one sesquiterpene selected from the group consisting of farnesene, longifolene, longicyclene, longipinene caryophyllene, humulene, murolene, each in the form of any one of their stereoisomers, and a mixture thereof.

17 . The liquid wood extract according to claim 1 ,

Assignees

• Firmenich & Cie

Inventors

• Cazeils Emmanuel
• Rivier Claudio
• Navarre Sébastien

Classifications

• A23L27/115

  obtained by distilling, stripping, or recovering of volatiles · CPC title

• C11B9/027 Primary

  Recovery of volatiles by distillation or stripping · CPC title

• C11B9/025 Primary

  Recovery by solvent extraction · CPC title