Compositions for the cryogenic distillation of high boiling molecules

Abstract

Various aspects of the present disclosure relate to compositions comprising a gas phase and a condensed phase, wherein the gas phase comprises molecules; the condensed phase comprises molecules; the gas phase has a temperature and a pressure; the molecules have a boiling point at the pressure of the gas phase; the boiling point of the molecules is lower than the temperature of the gas phase; the molecules have a vapor pressure at the temperature of the gas phase; the vapor pressure of the molecules is lower than the pressure of the gas phase; the condensed phase consists of one or both of a solid and a liquid phase; the condensed phase is suspended in the gas phase; and the condensed phase has a surface area to volume ratio of at least 500 per meter.

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This international application claims priority to U.S. Provisional Patent Application No. 63 / 412,428, filed October 1, 2022, and U.S. Provisional Patent Application No. 63 / 412,429, filed October 1, 2022, each of which is incorporated by reference in its entirety. [Background technology]

[0002] Natural product extraction is a mature technology field. The last major innovation was the development of supercritical fluid extraction in the 1980s. The oligopoly of a few large fragrance companies has created economies of scale and global reach. Their products have become commoditized and fungible, forcing cost reductions and shrinking profit margins.

[0003] As global supply chains increasingly demand sustainable agriculture, fair trade, and organic certification, many "current" good manufacturing practices are becoming anachronistic. Regulators and consumers are increasing pressure on the ingredients industry, with news suggesting that new regulations may inadvertently end the economically viable production of some key ingredients used in everyday consumer packaged goods.

[0004] New extraction techniques that allow higher profit margins without relying on less desirable production methods could allow fragrance companies to absorb the costs of additional regulations and save global supplies of ingredients that currently require production methods that may not be viable for years to come. Summary of the Invention

[0005] Various aspects of the present disclosure relate to the discovery that by converting a solid or liquid into an aerosol, molecules can be distilled from the aerosol in seconds at temperatures well below the boiling point of the molecule, a discovery that extends not only to aerosols but also to many compositions with large surface area to volume ratios. DETAILED DESCRIPTION OF THE INVENTION

[0006] Various aspects of the present disclosure relate to compositions comprising a gas phase and a condensed phase, wherein the gas phase comprises molecules; the condensed phase comprises molecules; the gas phase has a temperature and a pressure; the molecules have a boiling point at the pressure of the gas phase; the boiling point of the molecules is higher than the temperature of the gas phase; the molecules have a vapor pressure at the temperature of the gas phase; the vapor pressure of the molecules is lower than the pressure of the gas phase; the condensed phase consists of one or both of a solid and a liquid phase; the condensed phase is suspended in the gas phase; and the condensed phase has a surface area to volume ratio of at least 500 per meter. Such compositions may be prepared, for example, in the extraction chamber of an extractor described in EP 3,283,606 B1, which is incorporated by reference in its entirety. However, the present disclosure is not limited to compositions that may be made in an extraction machine according to EP 3,283,606 B1.

[0007] In this disclosure, the term "boiling point" includes both the conventional definition of the term and the following: if a molecule of this disclosure lacks a boiling point but has a sublimation point, the term "boiling point" encompasses the term sublimation point with respect to such molecule. For example, caffeine sublimes instead of boiling, and in this disclosure, the "boiling point" of caffeine refers to the sublimation point of caffeine.

[0008] In some embodiments, solid or liquid particles in the condensed phase are introduced into a chamber, passage, vessel, or tube containing a moving gas phase. Collision between the condensed phase and the gas phase causes the condensed phase to aerosolize in the gas phase, producing a composition according to the present disclosure, which is then transported through the chamber, passage, vessel, or tube. Molecules evaporate from the condensed phase to form a vapor in the gas phase. Methods are provided for separating the gas phase from the condensed phase, for example, by passing the composition through a cyclone. The vapor is then separated from the remaining gas phase. The gas phase containing the vaporized molecules may be passed through a spray or curtain of a trapping solvent or bubbled through a tank of trapping solvent to condense the vaporized molecules into condensed molecules. The trapping solvent may contain a compound that attracts and absorbs the vaporized molecules, thereby capturing a significant portion of the vaporized molecules from the gas phase and retaining the condensed molecules within the trapping solvent. The trapping solvent may include ethanol, a mixture of ethanol and water, or other solvents or solvent mixtures. The trapping solvent may advantageously be selected from a solvent or mixture of solvents in which the vaporized molecules are soluble or miscible, for example, to facilitate pumping of the vaporized molecules in the trapping solvent, although such characteristics are not limiting of the present disclosure. Trapped solvents are further described in European Patent No. 3,283,606 B1, which is incorporated by reference in its entirety. Over time, the vaporized molecules increasingly migrate from the gas phase into the trapping solvent. Once the trapping solvent has captured a sufficient amount of the vaporized molecules, the trapping solvent containing the condensed molecules may be manually or automatically removed from the extractor, and fresh trapping solvent may be manually or automatically returned to the extractor. Removal and introduction of the trapping solvent may be performed in incremental batches or continuously.

[0009] "Comprising" refers to an open setting, such that, for example, a gas phase containing a molecule can also contain a second molecule.

[0010] "Consisting of" refers to a closed setup, for example, where the condensed phase consists of one or both of a solid and a liquid phase, but cannot also contain a plasma phase.

[0011] "Condensed phase" refers, without limitation, to "one or both of a solid phase and a liquid phase" and "condensed phase" should not be construed to mean that the condensed phase is derived in part or in whole from a condensed gas phase, except as expressly provided in this disclosure.

[0012] In some embodiments, the composition has a vaporization rate for conversion of molecules in the condensed phase to molecules in the gas phase; the composition has a condensation rate for conversion of molecules in the gas phase to molecules in the condensed phase; the composition has a mass transfer rate equal to the vaporization rate minus the condensation rate; and the mass transfer rate is a positive number.

[0013] In some embodiments, the mass transfer rate is at least 5 micrograms of molecules per gram of composition per second. In some embodiments, the mass transfer rate is at least 5 micrograms of molecules per gram of condensed phase per second. In some embodiments, the mass transfer rate is at least 5 micrograms of molecules per gram of gas phase per second.

[0014] In some embodiments, the temperature of the gas phase is at least 25°C.

[0015] In some embodiments, the temperature of the gas phase is 250° C. or less.

[0016] In some embodiments, the temperature of the gas phase is greater than 100° C. and less than or equal to 250° C. In some embodiments, the temperature of the gas phase is greater than 100° C. and less than or equal to 235° C.

[0017] In some embodiments, the condensed phase has a temperature that is lower than the temperature of the gas phase.

[0018] In some embodiments, the composition has a non-zero sensible heat transfer rate from the vapor phase to the condensed phase.

[0019] In some embodiments, the composition has a sensible heat transfer rate from the vapor phase to the condensed phase of at least 2 joules per gram of condensed phase per second. In some specific embodiments, the composition has a sensible heat transfer rate from the vapor phase to the condensed phase of at least 20 joules per gram of condensed phase per second.

[0020] In some embodiments, the composition has a sensible heat transfer rate from the gas phase to the condensed phase of 20 kilojoules per gram of condensed phase per second or less. In some specific embodiments, the composition has a sensible heat transfer rate from the gas phase to the condensed phase of 2 kilojoules per gram of condensed phase per second or less. In some specific embodiments, the composition has a sensible heat transfer rate from the gas phase to the condensed phase of 1 kilojoule per gram of condensed phase per second or less. In some specific embodiments, the composition has a sensible heat transfer rate from the gas phase to the condensed phase of 500 joules per gram of condensed phase per second or less. In some specific embodiments, the composition has a sensible heat transfer rate from the gas phase to the condensed phase of 100 joules per gram of condensed phase per second or less. In some specific embodiments, the composition has a sensible heat transfer rate from the gas phase to the condensed phase of 50 joules per gram of condensed phase per second or less. In some specific embodiments, the composition has a sensible heat transfer rate from the gas phase to the condensed phase of 20 joules per gram of condensed phase per second or less.

[0021] In some embodiments, the composition has a non-zero latent heat transfer rate between the gas phase and the condensed phase. In some specific embodiments, the composition has a latent heat transfer rate between the gas phase and the condensed phase of at least 10 millijoules per gram of condensed phase per second. In some very specific embodiments, the composition has a latent heat transfer rate between the gas phase and the condensed phase of at least 100 millijoules per gram of condensed phase per second. In some specific embodiments, the composition has a latent heat transfer rate between the gas phase and the condensed phase of no more than 2 kilojoules per gram of condensed phase per second. In some specific embodiments, the composition has a latent heat transfer rate between the gas phase and the condensed phase of no more than 1 kilojoule per gram of condensed phase per second. In some very specific embodiments, the composition has a latent heat transfer rate between the gas phase and the condensed phase of no more than 500 joules per gram of condensed phase per second. In some specific embodiments, the composition has a latent heat transfer rate between the gas phase and the condensed phase of no more than 200 joules per gram of condensed phase per second.

[0022] In some embodiments, the condensed phase is introduced into a chamber, tube, or passage containing a moving gas phase. Upon entering the chamber, tube, or passage, the condensed phase is impacted by the gas phase. The impact by the gas phase aerosolizes the condensed phase in the gas phase. A portion of the condensed phase is converted to gas phase and transported through the chamber, tube, or passage. The gas phase may be heated to promote rapid evaporation of the molecules from the condensed phase to vapor. Additional heat may optionally be applied to the surfaces of the chamber, tube, or passage to apply additional energy to the composition. The heated gas phase is in contact with the condensed phase for a period of time and has an average temperature during the contact time. The total heating energy applied by the system to heat both the gas phase and the condensed phase may be as follows: if the average temperature is less than 275°C, the sum of the energy added to the gas and condensed phases is less than 100 kilojoules per gram of condensed phase; if the average temperature is less than 251°C, the energy added to the gas and condensed phases is less than 80 kilojoules per gram of condensed phase; if the average temperature is less than 225°C, the energy added to the gas and condensed phases is less than 70 kilojoules per gram of condensed phase; if the average temperature is less than 200°C, the energy added to the gas and condensed phases is less than 65 kilojoules per gram of condensed phase; if the average temperature is less than 175°C, the energy added to the gas and condensed phases is less than 55 kilojoules per gram of condensed phase. if the average temperature is less than 150°C, the energy added to the gas and condensed phases is less than 50 kilojoules per gram of condensed phase; if the average temperature is less than 125°C, the energy added to the gas and condensed phases is less than 45 kilojoules per gram of condensed phase; if the average temperature is less than 100°C, the energy added to the gas and condensed phases is less than 35 kilojoules per gram of condensed phase; if the average temperature is less than 75°C, the energy added to the gas and condensed phases is less than 30 kilojoules per gram of condensed phase; if the average temperature is less than 50°C, the energy added to the gas and condensed phases is less than 20 kilojoules per gram of condensed phase; if the average temperature is less than 35°C, the energy added to the gas and condensed phases is less than 10 kilojoules per gram of condensed phase.In some embodiments, the gas phase has a pressure of at least 0.1 to 100 atmospheres or less. In some specific embodiments, the gas phase has a pressure of at least 0.5 to 2 atmospheres or less. In some very specific embodiments, the gas phase has a pressure of at least 0.75 to 1.25 atmospheres or less.

[0023] In some embodiments, the composition has an altitude; the altitude has atmospheric pressure; and the pressure of the gas phase is greater than atmospheric pressure at the altitude.

[0024] In some embodiments, the condensed phase has a surface area to volume ratio per meter of at least 1000. In some specific embodiments, the condensed phase has a surface area to volume ratio per meter of at least 2400. In some even more specific embodiments, the condensed phase has a surface area to volume ratio per meter of at least 5000. In some very specific embodiments, the condensed phase has a surface area to volume ratio per meter of at least 10,000.

[0025] In some embodiments, the condensed phase has an average particle size of 5 millimeters or less, hi some specific embodiments, the condensed phase has an average particle size of 500 micrometers or less.

[0026] "Particle size" refers to the longest straight line distance between one point on a particle of a composition and another point on that particle in three-dimensional Euclidean space.

[0027] In some embodiments, the condensed phase has a mean terminal velocity of 5 meters per second or less in still, dry air at 1 atmosphere pressure. In some specific embodiments, the condensed phase has a mean terminal velocity of 1 meter per second or less in still, dry air at 1 atmosphere pressure.

[0028] In some embodiments, the composition has turbulence.

[0029] In some embodiments, the composition has an average Reynolds number greater than 100. In some specific embodiments, the composition has an average Reynolds number greater than 1000. In some very specific embodiments, the composition has an average Reynolds number greater than 10,000.

[0030] In some embodiments, the composition has an average Reynolds number of 1,000,000 or less.

[0031] In some embodiments, the composition has an average drag coefficient of at least 0.5.

[0032] In some embodiments, the composition has a laminar flow.

[0033] In some embodiments, the composition has an average velocity of at least 100 millimeters per second, hi some specific embodiments, the composition has an average velocity of at least 1 meter per second.

[0034] In some embodiments, the composition has an average kinetic energy of at least 5 microjoules per gram of composition. In some specific embodiments, the composition has an average kinetic energy of at least 500 microjoules per gram of composition.

[0035] In some embodiments, the composition has an average kinetic energy of 50 Joules per gram of composition or less, hi some specific embodiments, the composition has an average kinetic energy of 5 Joules per gram of composition or less.

[0036] In some embodiments, the composition comprises at least 1 gram of condensed phase per cubic meter of gas phase.

[0037] In some embodiments, the composition comprises no more than 1 gram of condensed phase per liter of vapor phase.

[0038] In some embodiments, the composition comprises at least 2 micrograms of molecules per gram of condensed phase.

[0039] In some embodiments, the composition comprises 200 milligrams of molecules or less per gram of condensed phase.

[0040] In some embodiments, the composition comprises at least 2 micrograms of molecules per gram of gas phase.

[0041] In some embodiments, the composition comprises 200 milligrams or less of the molecule per gram of gas phase.

[0042] In some embodiments, the gas phase comprises at least 10 percent of the molecules of the composition. In some specific embodiments, the gas phase comprises at least 25 percent of the molecules of the composition. In some very specific embodiments, the gas phase comprises at least 50 percent of the molecules of the composition.

[0043] In some embodiments, the gas phase has a higher molecular fraction than the condensed phase.

[0044] In some embodiments, the condensed phase comprises one or more polysaccharides, disaccharides, or monosaccharides. In some specific embodiments, the condensed phase comprises cellulose. In some very specific embodiments, the condensed phase comprises cellulose I.

[0045] In some embodiments, the condensed phase comprises dextrin.

[0046] In some embodiments, the condensed phase comprises a pyrodextrin.

[0047] In some embodiments, the condensed phase comprises levoglucosan.

[0048] In some embodiments, the condensed phase comprises one or more proteins, peptides, or amino acids. In some specific embodiments, the condensed phase comprises one or more proteins comprising an amino acid sequence encoding a cellulose synthase.

[0049] In some embodiments, the condensed phase comprises one or more nucleic acids, nucleotides, or nucleic acid bases. In some specific embodiments, the condensed phase comprises one or more nucleic acids comprising a nucleotide sequence encoding a cellulose synthase.

[0050] In some embodiments, the condensed phase comprises one, two, three, four, five, or each of sodium ions ("Na+"), potassium ions ("K+"), calcium ions ("Ca++"), magnesium ions ("Mg++"), monohydrogen phosphate, and dihydrogen phosphate. In some specific embodiments, the condensed phase comprises monohydrogen phosphate and dihydrogen phosphate.

[0051] In some embodiments, the condensed phase comprises chlorophyll.

[0052] In some embodiments, the condensed phase comprises cells. In some specific embodiments, the condensed phase comprises cells, each cell comprising a cell wall. In some very specific embodiments, the condensed phase comprises cells, the cells being plant cells.

[0053] In some embodiments, the condensed phase comprises cells; the cells comprise intact cells, each comprising an intracellular space and an intact cell membrane that inhibits fluid communication between the intracellular space and the gas phase; and the cells comprise lysed cells, each comprising an intracellular space and a lysed cell membrane that allows fluid communication between the intracellular space and the gas phase.

[0054] In some embodiments, at least 10% of the cells are lysed cells. In some embodiments, at least 25% of the cells are lysed cells. In some embodiments, at least 50% of the cells are lysed cells.

[0055] In some embodiments, the intracellular space of each intact cell contains volatile molecules; the volatile molecules have a boiling point at the pressure of the gas phase; and the boiling point of the volatile molecules at the pressure of the gas phase is lower than the temperature of the gas phase.

[0056] In some embodiments, the intracellular space of each intact cell contains superheated liquid.

[0057] In some embodiments, the intracellular space of each intact cell comprises gas.

[0058] In some embodiments, the intracellular space of each intact cell contains water; water has a boiling point at the pressure of the gas phase; and the boiling point of water at the pressure of the gas phase is lower than the temperature of the gas phase.

[0059] In some embodiments, the intracellular space of each intact cell contains superheated water.

[0060] In some embodiments, the intracellular space of each intact cell contains water vapor.

[0061] In some embodiments, the intracellular space of each intact cell has a pressure greater than the pressure of the gas phase.

[0062] In some embodiments, the composition has a non-zero cell lysis rate for converting intact cells into lysed cells. In some specific embodiments, the composition has a cell lysis rate for converting intact cells into lysed cells; the cell lysis rate is at least 1 percent of cells per second. In some very specific embodiments, the composition has a cell lysis rate for converting intact cells into lysed cells; the cell lysis rate is at least 10 percent of cells per second. Cell lysis improves extraction efficiency by promoting fluid communication between the intracellular space and the gas phase.

[0063] In some embodiments, the gas phase comprises one or more of molecular nitrogen, molecular oxygen, carbon dioxide, argon, neon, water vapor, and ethanol vapor, hi some specific embodiments, the gas phase comprises one or more of molecular nitrogen, molecular oxygen, carbon dioxide, argon, neon, water vapor, and ethanol vapor in a combined concentration of at least 50% by weight.

[0064] In some embodiments, the gas phase comprises molecular nitrogen. In some specific embodiments, the gas phase comprises molecular and molecular nitrogen in a combined concentration of at least 50% by weight.

[0065] In some embodiments, the gas phase lacks water vapor at a concentration of greater than 90% by weight. In some specific embodiments, the gas phase lacks water vapor at a concentration of greater than 50% by weight. In some embodiments, the gas phase lacks water vapor at a concentration of greater than 10% by weight.

[0066] In some embodiments, the gas phase comprises dry steam, hi some specific embodiments, the gas phase comprises molecules and dry steam in a combined concentration of at least 50% by weight.

[0067] In some embodiments, the molecule is a furan.

[0068] In some embodiments, the molecule is furyl-hydroxymethyl ketone (CAS: 17678-19-2); 2-methyl-benzofuran (CAS: 4265-25-2); 2-(2-furanylmethyl)-5-methyl-furan (CAS 13678-51-8); or 2,5-furandicarboxylic acid aldehyde (CAS: 823-82-5).

[0069] In some embodiments, the molecule is an alcohol.

[0070] In some embodiments, the molecule is nonan-1-ol (CAS: 143-08-8); decan-1-ol (CAS: 112-53-8); dodec-1-ol (CAS: 112-53-8); tetradecan-1-ol (CAS: 112-72-1); hexadecan-1-ol (CAS: 36653-82-4) or octadecan-1-ol (CAS: 112-92-5).

[0071] In some embodiments, the molecule is a fatty alcohol containing at least 9 carbon atoms.

[0072] In some embodiments, the molecule is nonen-3-ol (CAS: 21964-44-3).

[0073] In some embodiments, the molecule is an unsaturated alcohol.

[0074] In some embodiments, the molecule is 2-decen-1-ol (CAS: 22104-80-9).

[0075] In some embodiments, the molecule is an aromatic alcohol.

[0076] In some embodiments, the molecule is an aldehyde.

[0077] In some embodiments, the molecule is an unsaturated aldehyde.

[0078] In some embodiments, the molecule is a substituted aldehyde.

[0079] In some embodiments, the molecule is an unsubstituted aldehyde.

[0080] In some embodiments, the molecule is tetradecanal (CAS: 124-25-4); (Z)-2-decenal (CAS: 2497-25-8), or (E,E)-2,4-decadinal (CAS: 25152-84-5).

[0081] In some embodiments, the molecule is a carboxylic acid.

[0082] In some embodiments, the molecule is a low molecular weight volatile acid.

[0083] In some embodiments, the molecule is a fatty acid.

[0084] In some embodiments, the molecule is an unsaturated fatty acid.

[0085] In some embodiments, the molecule is a saturated fatty acid.

[0086] In some embodiments, the molecule is octanoic acid (CAS: 124-07-2); nonanoic acid (CAS: 112-05-0); n-decanoic acid (CAS: 334-48-5); n-hexadecanoic acid (CAS: 57-10-3); heptadecanoic acid (CAS: 506-12-7); or octadecanoic acid (CAS: 57-11-4).

[0087] In some embodiments, the molecule is a fatty acid.

[0088] In some embodiments, the molecule is a substituted carboxylic acid.

[0089] In some embodiments, the molecule is 2-ethylhexanoic acid (CAS: 149-57-5).

[0090] In some embodiments, the molecule is an unsaturated carboxylic acid.

[0091] In some embodiments, the molecule is trans-2-undecenoic acid (CAS: 15790-94-0).

[0092] In some embodiments, the molecule is an aromatic acid.

[0093] In some embodiments, the molecule is benzoic acid (CAS: 65-85-0) or phthalic acid (CAS: 88-99-3).

[0094] In some embodiments, the molecule is an ester.

[0095] In some embodiments, the molecule is a branched ester.

[0096] In some embodiments, the molecule is an unbranched ester.

[0097] In some embodiments, the molecule is a primary, secondary, tertiary, substituted, or unsubstituted ester.

[0098] In some embodiments, the molecule is a monoester.

[0099] In some embodiments, the molecule is a diester.

[0100] In some embodiments, the molecule is an ester of a saturated acid.

[0101] In some embodiments, the molecule is an ester of an unsaturated acid.

[0102] In some embodiments, the molecule is an ester of an aromatic acid.

[0103] In some embodiments, the molecule is methyl nonanoate (CAS: 1731-84-6); octyl butanoate (CAS: 110-39-4); isopropyl myristate (CAS: 110-27-0); ethyl nicotinate (CAS: 614-18-6); 3-hexenyl butanoate (CAS: 53398-84-8); diethyl butanedioate (CAS: 123-25-1); or diethyl itaconate (CAS: 2409-52-1).

[0104] In some embodiments, the molecule is a chemical derived from lignin.

[0105] In some embodiments, the molecule is a substituted phenol.

[0106] In some embodiments, the molecule is methyl salicylate (CAS: 119-36-8); eugenol (CAS 97-53-0); vanillin (CAS 121-33-5); (Z)-isoeugenol (CAS: 5932-68-3); ethyl anionate (CAS: 94-30-4); 4-methylguacol (CAS: 93-51-6) or (E)-2,6-dimethoxy-4-(prop-1-en-1-yl)phenol (CAS: 20675-95-0).

[0107] In some embodiments, the molecule is a terpene.

[0108] In some embodiments, the molecule is 1,3,8-p-menthatriene (CAS: 18368-95-1).

[0109] In some embodiments, the molecule is a monoterpene.

[0110] In some embodiments, the molecule is a sesquiterpene.

[0111] In some embodiments, the molecule is an oxide of a terpene.

[0112] In some embodiments, the molecule is an alkaloid.

[0113] In some embodiments, the molecule is a nitrogen-containing volatile compound.

[0114] In some embodiments, the molecule is caffeine (CAS:58-08-2).

[0115] In some embodiments, the molecule is nicotine (CAS:54-11-5).

[0116] In some embodiments, the molecule is 1H-pyrrole-2-carboxaldehyde (CAS: 1003-29-8).

[0117] In some embodiments, the molecule is a phytosterol.

[0118] In some embodiments, the molecule is a derivative of a phytosterol.

[0119] In some embodiments, the molecule is (4R,5R)-5-butyl-4-methyloxolan-2-one (CAS: 55013-32-6); (4S,5R)-5-butyl-4-methyloxolan-2-one (CAS: 39638-67-0); β-ionone (CAS: 8013-90-9); or δ-tetradecalactone (CAS: 2721-22-4).

[0120] In some embodiments, the molecule is an organosulfur compound.

[0121] In some embodiments, the molecule is bis(2-furfuryl) disulfide (CAS: 4437-20-1).

[0122] In some embodiments, the molecule is an alkane.

[0123] In some embodiments, the molecule is an alkene.

[0124] In some embodiments, the molecule is a hydrocarbon.

[0125] In some embodiments, the molecule is hydrocoumarin (CAS:119-84-6).

[0126] In some embodiments, the molecule is coumarin (CAS:91-64-5).

[0127] In some embodiments, the molecule is acetophenone (CAS: 98-86-2); α-bergamotol (CAS: 88034-74-6); α-bisabolol (CAS: 515-69-5); α-bisabolol oxide A (CAS: 22567-36-8); α-cadinol (CAS: 481-34-5); α-curcumene (CAS: 644-30-4); α-phencene (CAS: 471-84-1); α-phellandrene (CAS: 99-83-2); α-pinene (CAS: 80-56-8); α-santalol (CAS: 115-71-9); α-terpinene (CAS: 99-86-5); α-terpinene ol (CAS: 98-55-5); α-terpinyl acetate (CAS: 80-26-2); α-thujene (CAS: 2867-05-2); α-thujone (CAS: 546-80-5); α-zingiberene (CAS: 495-60-3); azulene (CAS: 275-51-4); benzyl acetate (CAS: 140-11-4); benzyl benzoate (CAS: 120-51-4); bergamotene (CAS: 6895-56-3); β-bisabolene (CAS: 495-61-4); β-caryophyllene (CAS: 87-44-5); β-damaskenone (CAS: 23696-85-7); β-eudesmol (CAS: 473-15-4); β-Farnesene (CAS: 77129-48-7); β-Phellandrene (CAS: 555-10-2); β-Pinene (CAS: 127-91-3); β-Santalol (CAS: 11031-45-1); β-Selinene (CAS: 17066-67-0); β-Sesquiphellandrene (CAS: 20307-83-9); β-Terpinene (CAS: 99-84-3); β-Terpinyl acetate (CAS.10198-23-9; β-Thujene (CAS: 28634-89-1); β-Thujone (CAS: 1125-12-8); Borneol (CAS: 464-45-9); Bornyl acetate (CAS: 76-49-3); Camphene (CAS: 79-92-5); Camphor (CAS: 76-22-2); Capsaicin (CAS: 404-86-4); Carene (CAS: 13466-78-9); Carvacrol (CAS: 499-75-2); Carvone (CAS: 99-49-0); caryophyllene oxide (CAS: 1139-30-6); cedrene (CAS: 469-61-4); cedrol (CAS: 77-53-2); chamazulene (CAS: 529-05-5); chavicol (CAS: 501-92-8); cinnamaldehyde (CAS: 104-55-2); citral (CAS: 5392-40-5); citronellal (CAS: 106-23-0); citronellol (CAS. 106-22-9; Citronellyl Formate (CAS: 105-85-1); Curzerene (CAS: 17910-09-7); Cyclopentadecanolide (CAS: 106-02-5); Decanal (CAS: 112-31-2); δ-Guaene (CAS: 3691-11-0); Ethyl Cinnamate (CAS: 103-36-6); Eugenol (CAS: 97-53-0); Farnesene (CAS: 502-61-4); Farnesol (C AS 4602-84-0; Furanoeudesma-1,3-diene (CAS 87605-93-4); Furfural (CAS 98-01-1); Furfuryl acetate (CAS 623-17-6); γ-Decalactone (CAS 706-14-9); γ-Muolene (CAS 30021-74-0); γ-Nonalactone (CAS 104-61-0); γ-Terpinene (CAS 99-85-4); γ-Terpinyl acetate (CAS 1 0235-63-9); Geraniol (CAS: 106-24-1); Geranyl acetate (CAS: 105-87-3); Germacrene A (CAS: 28387-44-2); Germacrene D (CAS: 37839-63-7); Guaiacol (CAS: 90-05-1); Heneicosane (CAS: 629-94-7); Humulene (CAS: 6753-98-6); Isoamyl benzoate (CAS: 94-46-2); Kesane (CAS.3321-66-2; limonene (CAS: 6876-12-6); linalool (CAS: 78-70-6); linalool oxide (CAS: 1365-19-1); linalyl acetate (CAS: 115-95-7); menthol (CAS: 89-78-1); menthone (CAS: 89-80-5); methyl cinnamate (CAS: 103-26-4); methyl eugenol (CAS: 93-15-2); methylpyrazine (CAS: 109-08-0); Myrcene (CAS: 123-35-3); Myristicin (CAS: 607-91-0); Neral (CAS: 5392-40-5); Nerol (CAS: 106-25-2); Nerolidol (CAS: 7212-44-4); Nootkatone (CAS: 91416-23-8); Nootkatine (CAS: 4431-03-2); Nootkatol (CAS: 53643-07-5); Nootkatone (CAS: 91416-23-8); Ocimene (CAS: 7216-56-0; Octanal (CAS: 124-13-0); para-Cresol (CAS: 106-44-5); para-Cymene (CAS: 99-87-6); Patchouli Alcohol (CAS: 5986-55-0); Perylene (CAS: 539-52-6); Phenylacetaldehyde (CAS: 122-78-1); Phenylacetic Acid (CAS: 103-82-2); Phenylethyl Alcohol (CAS: 60-12-8); Phytol (CAS: 150- 86-7); sabinene (CAS: 3387-41-5); safrole (CAS: 94-59-7); taumylol (CAS: 19912-62-0); terpinen-4-ol (CAS: 562-74-3); terpinolene (CAS: 586-62-9); thymol (CAS: 89-83-8); valencene (CAS: 4630-07-3); vanillin (CAS: 121-33-5); zingerone (CAS: 122-48-5); zingiberenol (CAS:58334-55-7; Zingiberol (CAS: 6754-68-3); 1,8-Cineole (CAS: 470-82-6); 1-Phenylethyl Acetate (CAS: 93-92-5); 2,6-Dimethylpyrazine (CAS: 108-50-9); 2-Furanmethanol (CAS: 98-00-0); 2-Heptanol (CAS: 543-49-7); 2-Heptanone (CAS: 110-43-0); 2-Heptyl Acetate (CAS: 5921-82-4); 2-Methoxy-4-vinylphenol (CAS: 7786-61-0); 2-Methyl-3-buten-2-ol (CAS: 115-18-4); 2-Methylbutanoic Acid (CAS: 116-53-0); 2-Nonanone (CAS: 821-55-6); 2-pentanol (CAS: 6032-29-7); 2-pentyl acetate (CAS: 626-38-0); 2-phenylethyl alcohol (CAS: 60-12-8); 2-undecanone (CAS: 112-12-9); 3-methylbutanoic acid (CAS: 503-74-2); 3-phenylpropanoic acid (CAS: 501-52-0); 4-methylguaiacol (CAS: 93-51-6); 5-methylfurfural (CAS: 620-02-0); 6-gingerol (CAS: 23513-14-6); 6-methyl-5-hepten-2-one (CAS: 110-93-0); or 6-shogaol (CAS: 555-66-8).

[0128] In some embodiments, the molecule is phenylacetaldehyde oxime (CAS:7028-48-0).

[0129] In some embodiments, the molecule is dihydrofarnesal (CAS:32480-08-3).

[0130] In some embodiments, the molecule is a cannabinoid carboxylic acid, tetrahydrocannabinolic acid, tetrahydrocannabivarin carboxylic acid, tetrahydrocannabiolic acid, cannabidiolic acid, cannabidivarin carboxylic acid, cannabidiolic acid, cannabichromene acid, cannabichromevarinic acid, cannabigerolic acid, cannabigerovarinic acid, cannabicycloic acid, cannabielsoic acid, perotetinene acid, cannabinolic acid, cannabivarin carboxylic acid, a carboxylate salt of any one of the preceding molecules, cannabinoid, tetrahydrocannabinol, tetrahydrocannabivarin, tetrahydrocannabiol, cannabidiol, cannabidivarin, cannabidiolchol, cannabichromene, cannabichromevarin, cannabigerol, cannabigerovarin, cannabicyclool, cannabielsoin, perotetinene, cannabinol, cannabivarin, a naturally occurring ether of any one of the preceding molecules, a stereoisomer of any one of the preceding molecules. Not β-caryophyllene, humulene, (-)-guaiol, (-)-α-bisabolol, linalool, α-terpineol, caryophyllene oxide, myrcene, eucalyptol, limonene, nerolidol, α-terpinene, borneol, (-)-isopulegol, δ-3-carene, para-cymene, or terpinolene.

[0131] In some embodiments, the composition is devoid of cannabis and cannabis-derived chemical species at a concentration of greater than 10% by weight. In some specific embodiments, the composition is devoid of cannabis and cannabis-derived chemical species at a concentration of greater than 1% by weight. In some very specific embodiments, the composition is devoid of cannabis and any cannabis-derived chemical species.

[0132] "Cannabis" refers to plants of the genus Cannabis and any part of a plant of the genus Cannabis. Cannabis includes, for example, marijuana and industrial hemp.

[0133] "Any chemical species derived from cannabis" includes, for example, chemical species extracted from cannabis and chemical species produced from cannabis, such as by decarboxylating a cannabis extract that contains one or more cannabinoid carboxylic acids.

[0134] In some embodiments, the condensed phase comprises biomass of a perennial plant.

[0135] In some embodiments, the condensed phase comprises annual plant biomass.

[0136] In some embodiments, the condensed phase comprises agave.

[0137] In some embodiments, the condensed phase comprises mezcal pomace or tequila agave pomace.

[0138] In some embodiments, the condensed phase comprises sugarcane.

[0139] In some embodiments, the condensed phase comprises sugarcane pomace.

[0140] In some embodiments, the condensed phase comprises sorghum pomace.

[0141] In some embodiments, the condensed phase comprises peat or smoked peat.

[0142] In some embodiments, the condensed phase comprises malted grain.

[0143] In some embodiments, the condensed phase comprises barley.

[0144] In some embodiments, the condensed phase comprises barley malt.

[0145] In some embodiments, the condensed phase comprises corn.

[0146] In some embodiments, the condensed phase comprises corn fiber, corn cob, or corn pomace.

[0147] In some embodiments, the condensed phase comprises rice.

[0148] In some embodiments, the condensed phase comprises fruit.

[0149] In some embodiments, the condensed phase comprises citrus fruit.

[0150] In some embodiments, the condensed phase comprises stone fruit.

[0151] In some embodiments, the condensed phase comprises xylem of stone fruit trees.

[0152] In some embodiments, the condensed phase comprises a complex fruit.

[0153] In some embodiments, the condensed phase comprises a berry.

[0154] In some embodiments, the condensed phase comprises stone fruit.

[0155] In some embodiments, the condensed phase comprises an achene.

[0156] In some embodiments, the condensed phase comprises pineapple.

[0157] In some embodiments, the condensed phase comprises tomato leaves.

[0158] In some embodiments, the condensed phase comprises dried plants.

[0159] In some embodiments, the condensed phase comprises dried peel.

[0160] In some embodiments, the condensed phase comprises dried citrus peel.

[0161] In some embodiments, the condensed phase comprises ylang-ylang species.

[0162] In some embodiments, the condensed phase comprises spices.

[0163] In some embodiments, the condensed phase comprises an herb.

[0164] In some embodiments, the condensed phase comprises flowers.

[0165] In some embodiments, the condensed phase comprises seeds.

[0166] In some embodiments, the condensed phase comprises a backbone.

[0167] In some embodiments, the condensed phase comprises roots.

[0168] In some embodiments, the condensed phase comprises leaves.

[0169] In some embodiments, the condensed phase comprises rhizomes.

[0170] In some embodiments, the condensed phase comprises a fungus.

[0171] In some embodiments, the condensed phase comprises yeast.

[0172] In some embodiments, the condensed phase comprises dry yeast.

[0173] In some embodiments, the condensed phase comprises mushrooms.

[0174] In some embodiments, the condensed phase comprises algae.

[0175] In some embodiments, the condensed phase comprises bacteria.

[0176] In some embodiments, the condensed phase is composed primarily of dried bacteria.

[0177] In some embodiments, the condensed phase comprises wood.

[0178] In some embodiments, the condensed phase comprises sawdust.

[0179] In some embodiments, the condensed phase comprises a core material.

[0180] In some embodiments, the condensed phase comprises cachaça wood.

[0181] In some embodiments, the condensed phase comprises Amburana cearensis.

[0182] In some embodiments, the condensed phase comprises Santalum seeds.

[0183] In some embodiments, the condensed phase comprises palo santo wood (Bursera graveolens).

[0184] In some embodiments, the condensed phase comprises oak seeds (Quercus).

[0185] In some embodiments, the condensed phase comprises American oak (Quercus alba).

[0186] In some embodiments, the condensed phase comprises French oak (Quercus robur).

[0187] In some embodiments, the condensed phase comprises English oak (Quercus petraea).

[0188] In some embodiments, the condensed phase comprises Hungarian oak (Quercus frainetto).

[0189] In some embodiments, the condensed phase comprises Quercus crispula.

[0190] In some embodiments, the condensed phase comprises Quercus mongolica.

[0191] In some embodiments, the condensed phase comprises Quercus pedunculata.

[0192] In some embodiments, the condensed phase comprises Quercus sessiliflora.

[0193] In some embodiments, the condensed phase comprises apple wood.

[0194] In some embodiments, the condensed phase comprises cherry wood.

[0195] In some embodiments, the condensed phase comprises maple wood.

[0196] In some embodiments, the condensed phase comprises hickory wood.

[0197] In some embodiments, the condensed phase comprises mesquite wood.

[0198] In some embodiments, the condensed phase comprises pecan material.

[0199] In some embodiments, the condensed phase comprises alder.

[0200] In some embodiments, the condensed phase comprises cypress wood.

[0201] In some embodiments, the condensed phase comprises cedar.

[0202] In some embodiments, the condensed phase comprises bourbon barrels, whiskey barrels, rum barrels, brandy barrels, wine barrels, Madeira barrels, port barrels, tequila barrels, mezcal barrels, sotol barrels, cachaça barrels, or barrels containing beer, wine, spirits, beverages, or spices, e.g., sawdust obtained from any one or more of the foregoing.

[0203] In some embodiments, the condensed phase comprises softwood. In some exemplary embodiments, the condensed phase is selected from the group consisting of Araucaria; Hoop pine (Araucaria cunninghamii); Monkey puzzle tree (Araucaria araucana); Parana pine (Araucaria angustifolia); Japanese cedar (Cedrus); Celery top pine (Phyllocladus aspleniifolius); Japanese cypress; Arizona cypress (Cupressus arizonica); Arasu (Fitzroya cupressoides); Japanese cypress (Chamaecyparis obtusa); Lawson cypress (Chamaecyparis lawsoniana), Mediterranean cypress (Cupressus sempervirens); Douglas fir (Pseudotsuga menziesii), European yew (Taxus baccata), fir (Abies); Balsam fir (Abies balsamea); Silver fir (Abies alba); Noble fir (Abies procera); Pacific silver fir (Abies amabilis); Hemlock (Tsuga); Eastern Hemlock (Tsuga canadensis); Mountain Hemlock (Tsuga mertensiana); Western Hemlock (Tsuga heterophylla); Huon Pine (Lagarostrobos franklinii); Kauri (Agathis australis); Queensland Kauri (Agathis robusta); Kaya (Torreya nucifera); Larch (Larix); European Larch (Larix decidua), Japanese Larch (Larix kaempferi), Tamarack (Larix laricina), Western Larch (Larix occidentalis); Pine (Pinus); European Black Pine (Pinus nigra); Jack Pine (Pinus banksiana); Lodgepole Pine (Pinus contorta); Monterey Pine (Pinus radiata); Ponderosa Pine (Pinus ponderosa);Red pine (Pinus resinosa);Scots pine (Pinus sylvestris); white pine; eastern white pine (Pinus strobus); western white pine (Pinus monticola); sugar pine (Pinus lambertiana); southern yellow pine; loblolly pine (Pinus taeda); longleaf pine (Pinus palustris); pitch pine (Pinus rigida); shortleaf pine (Pinus echinata); red cedar; eastern red cedar (Juniperus virginiana); western red cedar (Thuja plicata); coast redwood (Sequoia sempervirens); rim (Dacrydium cupressinum); spruce (Picea); Norway spruce (Picea abies); black spruce (Picea mariana); red spruce (Picea rubens); Sitka spruce (Picea sitchensis); white spruce (Picea glauca); Japanese cedar (Cryptomeria japonica); white cedar; northern white cedar (Thuja occidentalis); Atlantic white cedar (Chamaecyparis thyoides); African cypress (Widdringtonia species); pond cypress (Taxodium ascendens); swamp cedar (Taxodium distichum); Montezuma cypress (Taxodium mucronatum, Taxodium dubium); Chinese swamp cedar (Glyptostrobus pensilis); Cordilleran cypress (Austrocedrus chilensis); Japanese cypress (Callitris species); false cypress (Chamaecyparis species); Fujian cypress (Fokienia hodginsii); Guaitecas cypress (Pilgerodendron uviferum); Japanese cypress (Chamaecyparis obtusa); Patagonian cypress (Fitzroya cupressoides); Mediterranean cypress (Cupressus sempervirens);Includes Monterey cypress (Cupressus macrocarpa); Nootka cypress (Cupressus nootkatensis); Siberian cypress (Microbiota decussata); Summer cypress (Bassia scoparia); Western red cedar (Thuja plicata); or Nootka cypress (Cupressus nootkatensis).

[0204] In some embodiments, the condensed phase comprises angiosperm material.

[0205] In some exemplary embodiments, the condensed phase is selected from the group consisting of: Triplochiton scleroxylon; Acacia; African padak (Pterocarpus soyauxii); Afzelia (Afzelia africana); Agba (Gossweilerodendron balsamiferum); Alder (Alnus); Black alder (Alnus glutinosa); Red alder (Alnus rubra); Ash (Fraxinus); Black ash (Fraxinus nigra); Blue ash (Fraxinus quadrangulata); Common ash (Fraxinus excelsior); Green ash (Fraxinus pennsylvanica); Oregon ash (Fraxinus latifolia); Pumpkin ash (Fraxinus profunda); White ash (Fraxinus americana); Aspen (Populus); Giant aspen (Populus gradidentata); European aspen (Populus tremula); Quaking aspen (Populus tremuloides); Australian red cedar (Toona ciliata); Ayan (Distemonanthus benthamianus); Aquilaria; Balsa (Ochroma pyramidale); Basswood; American basswood (Tilia americana); White basswood (Tilia heterophylla); American beech (Fagus grandifolia); Birch (Betula); Gray birch (Betula populifolia); Black birch (Betula nigra); American white birch (Betula papyrifera); Birch (Betula lenta); Yellow birch (Betula alleghaniensis); Silver birch (Betula pendula); Downy birch (Betula pubescens); Black pea (Castanospermum australe); Blackwood (Blackwood); Australian blackwood (Acacia melanoxylon);African blackwood (Dalbergia melanoxylon); bloodwood (Brosimum rubescens); boxelder (Acer negundo); boxwood (Buxus sempervirens); Brazil walnut (Ocotea porosa); Brazilwood (Caesalpinia echinata); buckeye (Aesculus); horse chestnut (Aesculus hippocastanum); Ohio buckeye (Aesculus glabra); yellow buckeye (Aesculus flava); butternut squash (Juglans cinerea); California bay laurel (Umbellularia californica); camphor (Cinnamomum camphora); Cape chestnut (Calodendrum capense); wood sorrel (Catalpa); Ceylon satinwood (Chloroxylon swietenia); cherry (Prunus); black cherry (Prunus serotina); red cherry (Prunus pensylvanica); sweet cherry (Prunus avium); chestnut (Castanea); American chestnut (Castanea sativa); coachwood (Ceratopetalum apetalum); cocobolo (Dalbergia retusa); corkwood (Leitneria floridana); cottonwood; eastern cottonwood (Populus deltoides); swamp cottonwood (Populus heterophylla); cucumber tree (Magnolia acuminata); kumaru (Dipteryx); dogwood (Cornus); American dogwood (Cornus florida); dogwood (Cornus nuttallii); ebony (Diospyros); Andaman marblewood (Diospyros kurzii); ebony (Diospyros melanida); African ebony (Diospyros crassiflora); Ceylon ebony (Diospyros ebenum); elm; American elm (Ulmus americana); English elm (Ulmus procera);Rock elm (Ulmus thomasii); Slippery elm (Ulmus rubra); Witch elm (Ulmus glabra); Eucalyptus; Flooded gum (Eucalyptus grandis); White mahogany (Eucalyptus acmenoides); Brown mullet (Eucalyptus astringens); Southern mahogany (Eucalyptus botryoides); River red gum (Eucalyptus camaldulensis); Curry (Eucalyptus diversicolor); Blue gum (Eucalyptus globulus); Rose gum (Eucalyptus grandis); York gum (Eucalyptus loxophleba); Jarrah (Eucalyptus marginata); Tallowwood (Eucalyptus microcorys); Gray ironbark (Eucalyptus paniculata); Blackbutt (Eucalyptus pilularis); Mountain ash (Eucalyptus regnans); Australian oak (Eucalyptus obliqua); Alpine ash (Eucalyptus delegatensis); Red mahogany (Eucalyptus resinifera); Swamp mahogany (Eucalyptus robusta); Sydney blue gum (Eucalyptus saligna); Red ironbark (Eucalyptus sideroxylon); Redwood (Eucalyptus transcontinentalis); Wandoo (Eucalyptus wandoo); Crabgrass (Malus sylvestris); Pear tree (Pyrus communis); Tigerwood (Astronium); Greenheart (Chlorocardium rodiei); African blackwood (Dalbergia melanoxylon); Guanandi (Calophyllum brasiliense); Gum (Eucalyptus); Gum bolimbo (Bursera simaruba); Hackberry (Celtis occidentalis); Hickory (Carya);Pecan (Carya illinoinensis); Pignut hickory (Carya glabra); Shagbark hickory (Carya ovata); Shellbark hickory (Carya laciniosa); Hornbeam (Carpinus); American hornbeam (Ostrya virginiana); Ipe (Handroanthus); African teak (Milicia excelsa); Ironwood (Shorea); African hornbeam (Carpinus carolinianus); Sheek (Casuarina equisetifolia); Giant ironwood (Choricarpia subargentea); Diesel tree (Copaifera langsdorffii); Borneo ironwood (Eusideroxylon zwageri); Lignum vitae; Guaiacwood (Guaiacum officinale); Holywood (Guaiacum sanctum); Takhian (Hopea odorata); Black ironwood (Krugiodendron ferreum); Black ironwood (Olea); Lebombo ironwood (Androstachys johnsonii); Catalina ironwood (Lyonothamnus floribundus); Ceylon ironwood (Mesua ferrea); Desert ironwood (Olneya tesota), Persian ironwood (Parrotia persica), Brazilian ironwood (Caesalpinia ferrea), Yellow lapacho (Tabebuia serratifolia), Jacaranda Boca de Sapo (Jacaranda brasiliana), Brazilian jacaranda (Dalbergia nigra); Jatoba (Hymenaea courbaril); Kingwood (Dalbergia cearensis); Lacewood; Northern silk oak (Cardwellia sublimis); American sycamore (Platanus occidentalis); Platanus x acerifolia; Limba (Terminalia superba);Locust;Black locust (Robinia pseudoacacia);Honey locust (Gleditsia triacanthos); Mahogany; True mahogany (Swietenia); West Indian mahogany (Swietenia mahagoni); Bigleaf mahogany (Swietenia macrophylla); Pacific coast mahogany (Swietenia humilis); African mahogany (Khaya); Chinese mahogany (Toona sinensis); Australian red cedar (Toona ciliata); Philippine mahogany (Toona calantas); Indonesian mahogany (Toona sureni); Sapele (Entandrophragma cylindricum); Sipo (Entandrophragma utile); Tiama (Entandrophragma angolense); Kosipo (Entandrophragma candollei); Mountain mahogany (Entandrophragma caudatumi); Indian mahogany (Chukrasia velutina); Spanish cedar (Cedrela odorata); Light bosse (Guarea cedrata); Dark bosse (Guarea thompsonii); Musk tree (Guarea grandifolia); Carapa (Carapa guianensis); Bead tree (Melia azedarach); Maple (Acer); Hard maple; Sugar maple (Acer saccharum); Black maple (Acer nigrum); Soft maple; Boxwood (Acer negundo); Red maple (Acer rubrum); Silver maple (Acer saccharinum); European maple; Sycamore maple (Acer pseudoplatanus); Marblewood (Marmaroxylon racemosum); Marie (Corymbia calophylla); Meranti (Shorea); Merbau (Intsia bijuga); Mesquite; Mopane (Colophospermum mopane); oak (Quercus); American oak or white oak (Quercus alba); bur oak (Quercus macrocarpa);Post oak (Quercus stellata); Swamp white oak (Quercus bicolor); Southern live oak (Quercus virginiana); Swamp chestnut oak (Quercus michauxii); Chestnut oak (Quercus prinus); Chinese oak (Quercus; muhlenbergii); Canyon live oak (Quercus chrysolepis); Overcup oak (Quercus lyrata); Red oak (Red oak); Northern red oak (Quercus rubra); Eastern black oak (Quercus velutina); Laurel oak (Quercus laurifolia); Southern red oak (Quercus falcata); Water oak (Quercus nigra); Willow oak (Quercus phellos); Nuttle oak (Quercus texana); Okoumea klaineana; Olive (Olea europaea); Pink ivory (Berchemia zeyheri); Poplar (Poplar); Balsam poplar (Populus balsamifera); Black poplar (Populus nigra); Hybrid black poplar (Populus × canadensis); Purpleheart (Peltogyne); Prosopis species; Queensland maple (Flindersia brayleyana); Queensland walnut (Endiandra palmerstonii); Ramin (Gonystylus); Redheart, Chaktecock (Erythroxylon mexicanum); Sal (Shorea robusta); Sweetgum (Liquidambar styraciflua); Sandalwood (Santalum); Australian sandalwood (Santalum spicatum); Indian sandalwood (Santalum album); Hawaiian sandalwood (Santalum ellipticum, Santalum freycinetianum, Santalum paniculatum, Santalum haleakalae); Santalum acuminatum; Santalum yasi; Santalum spicatum; Sassafras (Sassafras albidum); Southern sassafras (Atherosperma moschatum); Satine (Brosimum rubescens);Silky oak (Grevillea robusta), silver wattle (Acacia dealbata), sourwood (Oxydendrum arboreum), Spanish cedar (Cedrela odorata), Spanish elm (Cordia alliodora), tamboti (Spirostachys africana), teak (Tectona grandis), Thai rosewood (Dalbergia cochinchinensis), tupelo (Nyssa), black tupelo (Nyssa sylvatica); tulip tree (Liriodendron tulipifera); turpentine (Syncarpia glomulifera); walnut (Juglans); Eastern black walnut (Juglans nigra); common walnut (Juglans regia); wenge (Millettia laurentii); panga panga (Millettia stuhlmannii); willow (Salix serrata); black willow (Salix serrata) nigra); cricket bat willow (Salix alba Caerulea); white willow (Salix alba); weeping willow (Salix babylonica); or zingana (Microberlinia brazzavillensis);

[0206] In some exemplary embodiments, the condensed phase is selected from the group consisting of cachaça; Amburana acreana; Amburana cearensis; Amburana erythrosperma; apple; Malus domestica; Malus sieversii; Palo santo (Bursera graveolens); clove (Syzygium aromaticum); star anise (Illicium verum); cinnamon; Ceylon cinnamon (Cinnamomum verum); cinnamon burmannii (Cinnamomum burmannii); cinnamon cassia (Cinnamomum cassia); Cinnamomum loureiroi; Cinnamomum citriodorum; Brazilian rosewood (Dalbergia nigra); cocobolo (Dalbergia retusa); lignum vitae (Guaiacum officinale); raspberry jamwood (Acacia acuminata); kaya; Torreya californica; Torreya fargesii; Torreya grandis;Torreya jackii;Torreya nucifera;Torreya taxifolia;Thuya (Tetraclinis articulata);Cacao tree (Theobroma cacao);Prunus persica;Apricot (Prunus armeniaca;Prunus brigantina;Prunus cathayana;Prunus dasycarpa;Prunus hongpingensis;Prunus hypotrichodes;Prunus limeixing;Prunus mandshurica;Prunus mume;Prunus sibirica;Prunus zhengheensis);plum (Prunus domestica;Prunus salicina;Prunus simonii);almond (Prunus amygdalus;Prunus dulcis);pistachio (Pistacia vera);honey mesquite (Prosopis) glandulosa); velvet mesquite (Prosopis velutina);Mesquite (Prosopis spp., Prosopis pallida, or Prosopis juliflora); creosote bush (Larrea tridentata); mulberry (Morus); crab apple (Malus sylvestris); or any species of magnolia.

[0207] In some embodiments, the condensed phase comprises biomass of plant milk. In some specific embodiments, the plant milk is lily of the valley (Convallaria), lilac (Syringa), honeysuckle (Lonicera), violet (Violaceae), rubber tree (Philadephaceae), hyacinth (Hiacinthus), sweet pea (Lathyrus), or magnolia (Magnoliaceae) flower seeds. In some very specific embodiments, the condensed phase comprises biomass of lily of the valley.

[0208] In some embodiments, the condensed phase is selected from the group consisting of plum blossom, cherry blossom, apple blossom, orange blossom, lemon blossom, lime blossom, Satsuma flower, Osmanthus flower, jasmine flower, frangipani (plumeria) flower, night jasmine, lavender, tuberose flower, lily, rose, rose flower, ylang-ylang (Cananga odorata), Artabotrys hexapetalus, daffodil flower, scented primrose (Primula vulgaris), sweet autumn clematis (Clematis terniflora), Nicotiana, viburnum, mock orange (Philadelphus), lilac (Syringa), Brugmansia, Daphne, night jasmine (Matthiola longipetala), magnolia, Brunfelsia pauciflora, and the like. pauciflora, Freesia, Wrightia religiosa, Hedychium coronarium, Fagraea berteroana, Tabernaemontana divaricate, Magnolia (Magnoliaceae), Magnolia champaca, Cestrum nocturnum, Gardenia, Wisteria, Azalea, Osmanthus, Camellia, Sasanqua, or Magnolia grandiflora.

[0209] In some embodiments, the condensed phase is selected from the group consisting of agarwood, fragrant wood; Aquilaria malaccensis; frankincense; Boswellia; Boswellia sacra; Boswellia bhaw-dajiana; Boswellia carteri; Boswellia frereana, Boswellia serrata; Boswellia thurifera; Boswellia papyrifera; galbanum; Ferula; Ferula gummosa; Ferula rubricaulis; orris; Rhizoma iridis; Iris germanica; Iris pallida; a species of Iris; squirrel root, iris root; amber; Baltic amber; ambergris; ambrette; ambrette seed; amyris; balsamic; benzoin; pine; resin; juniper; turpentine; styrax tree; bergamot; bergamot orange; crone; cashmeran; galbanum resin; guaiac wood; hedione; heliotrope; heliotrope flower; vetiver; vetiver root; patchouli; patchouli leaf; patchouli bush; indole, iso-e-super, jasmine; coconut; labdanum; rock rose bush; leather; myrrh; commiphora; narcissus; oakmoss; lichen; opopanax; sweet myrrh; balsam; osmanthus; rose; clary sage; or tonka bean.

[0210] In some embodiments, the condensed phase may be selected from the group consisting of allspice (Pimenta dioica); angelica (Angelica archangelica); anise (Pimpinella anisum); asafoetida (Ferula assa-foetida); bay leaf (Laurus nobilis); basil (Ocimum basilicum); bergamot (Monarda species); black cumin (Nigella sativa); black mustard (Brassica nigra); black pepper (Piper nigrum); borage (Borago officinalis); brown mustard (Brassica juncea); burnet (Sanguisorba minor and S. officinalis); caraway (Carum carvi); cardamom (Elettaria cardamomum); cassia (Cinnamomum cassia); catnip (Nepeta cataria); cayenne pepper (Capsicum annuum); celery seed (Apium graveolens, variety dulce); chervil (Anthriscus cerefolium); chicory (Cichorium intybus); chili pepper (Capsicum species); chives (Allium schoenoprasum); Sicily (Myrrhis odorata); coriander (Coriandrum sativum); cinnamon (Cinnamomum verum); cloves (Syzygium aromaticum); coriander (Coriandrum sativum); costmary (Tanacetum balsamita); cumin (Cuminum cyminum); curry; dill (Anethum graveolens); fennel (Foeniculum vulgare);Fenugreek (Trigonella foenum-graecum), fillet (Sassafras albidum), ginger (Zingiber officinale), grains of paradise (Aframomum melegueta), holy basil (Ocimum tenuiflorum), horehound (Marrubium vulgare); horseradish (Armoracia rusticana); hyssop (Hyssopus officinalis); lavender (Lavandula species); lemon balm (Melissa officinalis); lemongrass (Cymbopogon citratus); lemon verbena (Aloysia citrodora); licorice (Glycyrrhiza glabra); lovage (Levisticum officinale); mace (Myristica fragrans); marjoram (Origanum majorana); nutmeg (Myristica fragrans); oregano (Origanum vulgare);Paprika (Capsicum annuum); These include parsley (Petroselinum crispum); peppermint (Mentha × piperita); poppy seeds (Papaver somniferum); rosemary (Salvia rosmarinus); rue (Ruta graveolens); saffron (Crocus sativus); sage (Salvia officinalis); savory (Satureja hortensis and S. montana); sesame (Sesamum indicum); sorrel (Rumex species); star anise (Illicium verum); spearmint (Mentha spicata); tarragon (Artemisia dracunculus); thyme (Thymus vulgaris); turmeric (Curcuma longa); vanilla (Vanilla planifolia and V. tahitensis); wasabi (Eutrema japonicum); or white mustard (Sinapis alba).

[0211] In some embodiments, the condensed phase comprises saffron.

[0212] In some embodiments, the condensed phase comprises vanilla.

[0213] In some embodiments, the condensed phase comprises cinnamon.

[0214] In some embodiments, the condensed phase comprises capsaicin.

[0215] In some embodiments, the condensed phase comprises menthol.

[0216] In some embodiments, the condensed phase comprises certain peppercorns.

[0217] In some embodiments, the condensed phase comprises leather.

[0218] In some embodiments, the condensed phase comprises a plant species from the genus Nicotiana.

[0219] In some embodiments, the condensed phase is Nicotiana acuminata; Nicotiana Africana; Nicotiana alata; Nicotiana attenuata; Nicotiana benthamiana; Nicotiana clevelandii; Nicotiana glauca; Nicotiana glutinosa; Nicotiana langsdorffii; Nicotiana longiflora; Nicotiana occidentalis; obtusifolia;Nicotiana otophora;Nicotiana plumbaginifolia;Nicotiana quadrivalvis;Nicotiana rustica;Nicotiana suaveolens;Nicotiana sylvestris;Nicotiana tabacum;Nicotiana tomentosiformis;Nicotiana×didepta;Nicotiana debneyi×Nicotiana.tabacum;Nicotiana×digluta;Nicotiana glutinosa×Nicotiana tabacum; Nicotiana × sanderae; or Nicotiana alata × Nicotiana forgetiana.

[0220] In some embodiments, the condensed phase comprises tea.

[0221] In some embodiments, the condensed phase is selected from the following types of tea: Green Tea; Chun Mee; Chun Lu; Bi Luo Chun; Chinese Green Tea; Maofeng; Yellow; Jasmine; Anji Bai Cha; Maojian; Taiping Houkui; Jin Shan; Longjing; Sejak; Ujeon; Sanbancha; Yonbancha; Sencha; Gyokuro; Kabusecha; Tencha; Matcha; Budcha; Shincha; Hojicha; Kukicha; Bancha; Genmaicha; Konacha; Kamairicha; Tamaryokucha; Black Tea; Assam; English Breakfast; Earl Grey; Darjeeling; Rukeri; Pu-erh; Scottish Afternoon; Irish Breakfast; Mirima; Ceylon. ;Chai;Pan Yang Kong Gu;Keemun;Lapsang Souchong;Golden Tip;Temi Sikkim;Ning Bu;Wakuo Cha;White Tea;Yin Zhen;White Peony;Shou Mei;Gong Mei;Darjeeling White;Oolong Tea;Da Hong Pao;Shui Jin Gui;Tie Luo Han;Shui Daffodil;Bai Ziyuan;Tie Guanyin (Iron Goddess);Mi Lan Xiang Dancong;Gu Shu Dangun;Guanyin Tea;Dancong Tea;Cassia;Dayuling;Dongding;Oriental Beauty;Alishan;Baozhong Tea;Ruan Zhi;Jin Xuan Tea;Lishan Tea.

[0222] In some embodiments, the condensed phase comprises herbal tea.

[0223] In some embodiments, the condensed phase comprises one or more of the following types of tea: avocado leaf; bamboo; butterfly pea flower; chaga mushroom; chamomile; lavender; liquorice; guayusa; honeysuckle flower; lemon; mint; olive leaf; hibiscus; rooibos; turmeric; pumpkin spice; chrysanthemum; buckwheat; honeybush; bush; mamaki; yaupon; or yerba mate.

[0224] In some embodiments, the condensed phase comprises yerba mate.

[0225] In some embodiments, the condensed phase comprises rooibos.

[0226] In some embodiments, the condensed phase comprises meat or dried meat.

[0227] In some embodiments, the condensed phase comprises dried mushrooms.

[0228] In some embodiments, the condensed phase comprises legumes.

[0229] In some embodiments, the condensed phase comprises soy.

[0230] In some embodiments, the condensed phase comprises fermented plant matter.

[0231] In some embodiments, the condensed phase comprises dried fermented plant matter. In some embodiments, the boiling point of the molecules at the pressure of the gas phase is at least 10° C. higher than the temperature of the gas phase. In some specific embodiments, the boiling point of the molecules at the pressure of the gas phase is at least 20° C. higher than the temperature of the gas phase. In some even more specific embodiments, the boiling point of the molecules at the pressure of the gas phase is at least 40° C. higher than the temperature of the gas phase. In some very specific embodiments, the boiling point of the molecules at the pressure of the gas phase is at least 100° C. higher than the temperature of the gas phase.

[0232] Various aspects of the present disclosure relate to methods of separating a molecule from an impurity, including providing a composition comprising a molecule and an impurity, wherein the molecule is present in the composition in a solid or liquid phase and the impurity is present in the composition in a solid or liquid phase; converting the molecule to a vaporized molecule in a gas phase, wherein the gas phase has a pressure and a temperature, the molecule has a boiling point at the pressure and a vapor pressure at the temperature, the pressure of the gas phase is greater than the vapor pressure of the molecule, the boiling point of the molecule is greater than the temperature of the gas phase, and the impurity lacks vapor pressure or has a vapor pressure at a temperature lower than the vapor pressure of the molecule at the temperature; separating the vaporized molecule from the impurity, and condensing the vaporized molecule to a condensed molecule. [Example]

[0233] The following examples provide a framework for implementing certain aspects of the present disclosure, and these examples do not limit the scope of this patent document or any claims that may be made from the disclosure of this patent document.

[0234] Example 1: Extraction of coumarin from Brazilian oak barrels.

[0235] Brazilian oak is known to contain coumarin. Brazilian oak barrels are commonly used to age cachaça, a distilled spirit with qualities similar to rum. Coumarin is the primary aroma source of Brazilian oak, but is present in small amounts, making it very difficult to extract using traditional solvent methods.

[0236] Three kilograms of moderately burned Brazilian oak wood was ground and extracted using the extractor described in European Patent No. 3,283,606 B1. The extractor was operated at an extraction temperature not exceeding 205°C. The evaporated coumarin was recovered in 3 liters of ethanol. One hundred milliliters of the resulting extract was analyzed using high-pressure liquid chromatography (HPLC). The extract was found to contain 1.138 milligrams of coumarin per kilogram.

[0237] Based on the known amount of coumarin in burnt Brazilian oak, the disclosed method efficiently extracted coumarin at extraction temperatures well below its known boiling point. Although coumarin's boiling point is 301.7°C, the extractor never exceeded an extraction temperature of 205°C.

[0238] These results confirm that the composition of the present disclosure was produced in an extractor, the condensed phase consisted of crushed Brazilian oak wood, the gas phase consisted of the extractor gas stream, and the molecule was coumarin.

[0239] Example 2: Toasted French Oak Extraction Although toasted French oak is known to contain only a few milligrams of vanillin, eugenol, and isoeugenol per kilogram, these compounds contribute significantly to barrel-aged whiskey and other barrel-aged spirits.

[0240] Three kilograms of moderately toasted French oak was ground and extracted using the extractor described in European Patent No. 3,283,606 B1. The extractor was operated at an extraction temperature not exceeding 205°C. The evaporated vanillin, eugenol, and isoeugenol were recovered in 3 kilograms of a collection solvent consisting of ethanol and water. One hundred milliliters of the resulting extract was analyzed using gas chromatography-mass spectrometry (GC-MS) and found to contain 15.8 milligrams of vanillin per kilogram, 0.2 milligrams of eugenol per kilogram, and 0.9 milligrams of isoeugenol per kilogram.

[0241] Based on the known amounts of vanillin, eugenol, and isoeugenol in toasted French oak, the disclosed method efficiently extracted each of these compounds at temperatures much lower than their known boiling points. Vanillin has a boiling point of 285°C, but the extractor never exceeded an extraction temperature of 205°C. Eugenol has a boiling point of 252°C, but the extractor never exceeded an extraction temperature of 205°C. Isoeugenol has a boiling point of 266°C, but the extractor never exceeded an extraction temperature of 205°C.

[0242] These results confirm that the compositions of the present disclosure were produced in an extractor, the condensed phase consisted of crushed French oak, the gas phase consisted of the extractor gas stream, and the molecules were vanillin, eugenol, or isoeugenol.

[0243] Example 3: Extraction of Burnt American Oak Although charred American oak is known to contain only a few milligrams of vanillin, eugenol, and isoeugenol per kilogram, these compounds contribute significantly to the quality of barrel-aged whiskey and other barrel-aged spirits.

[0244] Three kilograms of well-burned American oak was ground and extracted using the extractor described in European Patent No. 3,283,606 B1. The extractor was operated at an extraction temperature not exceeding 205°C. The evaporated vanillin, eugenol, and isoeugenol were recovered in 3 kilograms of a collection solvent consisting of ethanol and water. The resulting extract was analyzed using a GC-MS method and found to contain 13.1 milligrams of vanillin per kilogram, 0.9 milligrams of eugenol per kilogram, and 2.4 milligrams of isoeugenol per kilogram.

[0245] Based on the known amounts of these compounds in burnt American oak, the disclosed method efficiently extracted each of these compounds at temperatures well below their known boiling points. Vanillin has a boiling point of 285°C, but the extractor never exceeded an extraction temperature of 205°C. Eugenol has a boiling point of 252°C, but the extractor never exceeded an extraction temperature of 205°C. Isoeugenol has a boiling point of 266°C, but the extractor never exceeded an extraction temperature of 205°C.

[0246] These results confirm that the compositions of the present disclosure were produced in an extractor, the condensed phase consisted of crushed American oak, the gas phase consisted of the extractor gas stream, and the molecules were vanillin, eugenol, or isoeugenol.

[0247] Example 4: Extraction of Sandalwood The characteristic scent of sandalwood comes from α-santalol, which boils at 302°C.

[0248] Three kilograms of sandalwood are finely ground to increase surface area. The ground sandalwood is homogenized by mixing to ensure uniformity throughout. Random 100 gram samples of the homogenized sandalwood are examined using HPLC to analyze the α-santalol content of the starting material. Test results indicate that the pre-extracted sandalwood contains approximately 33,000 milligrams of α-santalol per kilogram of sandalwood.

[0249] The remaining 2,900 grams of sandalwood is extracted using the disclosed method at a sweep gas temperature of 210° C. and a pressure of 760.00 mmHg. The evaporated α-santalol is captured in 3 kilograms of a collection solvent consisting of ethanol and water, producing a highly fragrant sandalwood extract.

[0250] One hundred milliliters of the extract is homogenized and tested using HPLC. The test results show that the extract contains 23,430 milligrams per kilogram. The depleted extracted sandalwood is homogenized by mixing, and a 100 gram sample is tested using HPLC. The test results show that the pre-extracted sandalwood contains approximately 7,260 milligrams of α-santalol per kilogram of sandalwood.

[0251] The boiling point of α-santalol is 302°C, but efficient extraction is achieved at 210°C. Comparing the HPLC results of sandalwood before and after extraction shows that approximately 78% of the available α-santalol has been removed from the sandalwood. Comparing the HPLC results of sandalwood before and after extraction shows that approximately 76% of the available α-santalol has been captured from the sandalwood. Approximately 2% of the total α-santalol is unaccounted for.

[0252] These results confirm that the composition of the present disclosure was produced in an extractor, the condensed phase consisted of ground sandalwood, the gas phase consisted of the extractor gas stream, and the molecule was α-santalol.

[0253] Example 5: Extraction of Sandalwood Three kilograms of ground sandalwood was crushed and extracted using the method of the present invention at a sweep gas temperature of 200°C. A highly aromatic sandalwood extract was produced, judged by several senior fragrance industry experts to have a higher aroma intensity than steam distillation and solvent extraction reference samples. Sensory testing was performed on the raw sandalwood material before and after extraction using the disclosed method. The starting material exhibited a strong aroma of freshly crushed sandalwood. The extracted raw material had very little remaining aroma. This experiment was repeated at sweep gas temperatures of 170°C, 180°C, and 210°C. In each case, most of the α-santalol-related aroma was removed from the starting material.

[0254] These results confirm that the composition of the present disclosure was produced in an extractor, the condensed phase consisted of ground sandalwood, the gas phase consisted of the extractor gas stream, and the molecule was α-santalol.

[0255] Example 6: Extraction of Orris The characteristic aroma of orris root comes from iron, which boils at 295°C.

[0256] Three kilograms of orris are finely ground to increase surface area. The ground orris is homogenized by mixing to ensure uniformity throughout. Random 100 gram samples of the homogenized orris are analyzed using an HPLC method to analyze the ironone content of the starting material. Test results indicate that the orris prior to extraction contains approximately 1,880 milligrams of ironone per kilogram of orris.

[0257] The remaining 2,900 grams of orris is extracted using the method of the present disclosure at a sweep gas temperature of 200°C and a pressure of 760.00 mmHg. The evaporated iron is captured in 3 kilograms of a collection solvent consisting of ethanol and water, producing a highly aromatic orris extract.

[0258] One hundred milliliters of the extract is tested using HPLC. The test results show that the extract contains 1,523 milligrams of iron per kilogram. The depleted extracted orris is homogenized by mixing, and a 100 gram sample is tested using HPLC. The test results show that the extracted orris contains only 301 milligrams of iron per kilogram of orris.

[0259] The boiling point of iron is 295°C, but efficient extraction is achieved at 200°C. Comparing the HPLC results of orris before and after extraction shows that approximately 84% of the available iron is removed from the orris. Comparing the HPLC results of orris before and after extraction shows that approximately 81% of the available iron is captured from the orris. Approximately 3% of the total iron is unaccounted for.

[0260] These results confirm that the compositions of the present disclosure were produced in an extractor, the condensed phase consisted of ground oris, the gas phase consisted of the extractor gas stream, and the molecules were irons.

[0261] Example 7: Extraction of Orris Three experiments were conducted using ground orris as the starting material. In each experiment, 3 kilograms of ground orris root was extracted using the method of the present invention. The first experiment utilized a sweep gas temperature of 170°C. The second experiment utilized a sweep gas temperature of 190°C. The third experiment utilized a sweep gas temperature of 205°C. In each case, a highly aromatic orris extract was produced. Several senior fragrance industry experts judged the orris extract produced by the disclosed method to be preferable to a steam-distilled and solvent-extracted reference sample. For each experiment, sensory evaluations were conducted on the starting material before and after extraction using the disclosed method. The starting material exhibited a strong aroma of freshly ground orris. In all experiments, very little aroma remained in the extracted material, with the 170°C extraction material retaining only a slight aroma compared to the 205°C extraction material. In each case, the majority of the irones present in the orris were apparently removed from the starting material and precipitated in the extract.

[0262] These results confirm that the composition of the present disclosure was produced in an extractor, the condensed phase consisted of ground orris, the gas phase consisted of the extractor gas stream, and the molecules were irons.

[0263] Example 8: Extraction of various woods and detection of high boiling point compounds Several different compositions, consisting of different types of wood, wooden barrels that had previously held spirits, and wooden barrels that had previously held wine, were separately ground into sawdust particles with an average length of less than 1 millimeter. In a series of separate tests, the wood particles were extracted using the disclosed method, and the resulting extracts were subjected to GC-MS analysis. Experiments were performed in an extractor such as that described in European Patent No. 3,283,606 B1. For each test, the sweep gas was heated to approximately 205°C. The wood particles were continuously introduced at a metered rate into the extractor's extraction chamber by an auger. Upon entering the extraction chamber, the wood particles were bombarded with the sweep gas. The impact of the sweep gas aerosolized the wood particles, transporting them with the sweep gas through the extraction chamber. The aerosolized composition remained in contact with the sweep gas for several seconds as it traversed the entire length of the extraction chamber. The extraction chamber rotated, creating turbulence and enhancing the mass transfer rate of the composition molecules to vaporized molecules. In each test, molecules from each of the different compositions were evaporated to form a vapor. A cyclone separator was used to separate the vaporized molecules from the non-evaporated components of the wood particles. The sweep gas containing the separated vaporized molecules was passed through a spray of trapping solvent to condense the molecules into condensed molecules. The trapping solvent contained a blend of ethanol and water to attract, absorb, and retain the molecules. To achieve the desired concentration of condensed molecules in the trapping solvent, in each test, the trapping solvent spray was continuously circulated with a liquid pump, and the sweep gas containing the vaporized molecules was continuously passed through the trapping solvent spray. The embodiment was operated continuously until approximately 3 kilograms of wood particles had passed through the extractor. In each case, the aromatic wood extract was captured in the trapping solvent. 100 milliliters of each extract was analyzed using GC-MS and HPLC methods. Although the sweep gas and extraction chamber were kept below approximately 205°C, significant amounts of the following high-boiling molecules were detected in different tests: furyl-hydroxymethyl ketone (CAS: 17678-19-2), which boils at 239°C; 2,5-furandicarboxaldehyde (CAS: 823-82-5), which boils at 276-277°C; nonan-1-ol (CAS: 143-08-8), which boils at 214°C;Decane-1-ol (CAS: 112-53-8) boils at 231°C; dodecan-1-ol (CAS: 112-53-8) boils at 230°C; tetradecan-1-ol (CAS: 112-72-1) boils at 289°C; hexadecan-1-ol (CAS: 36653-82-4) boils at 344°C; octadecan-1-ol (CAS: 112-92-5) boils at 384°C; 2-decen-1-ol (CAS: 22104-80-9) boils at 229°C; phenylethyl alcohol (CAS: 60-12-) boils at 219-221°C. 8); tetradecanal (CAS: 124-25-4), which boils at 260°C; (Z)-2-decenal (CAS: 2497-25-8), which boils at 226-230°C; (E,E)-2,4-decadienal (CAS: 25152-84-5), which boils at 279-280°C; octanoic acid (CAS: 124-07-2), which boils at 237°C; nonanoic acid (CAS: 112-05-0), which boils at 254°C; n-decanoic acid (CAS: 334-48-5), which boils at 268.00-270°C; n-hexadecanoic acid (CAS: 57-10-3), which boils at 351°C; 26 Heptadecanoic acid (CAS: 506-12-7), boiling at 3°C; octadecanoic acid (CAS: 57-11-4), boiling at 361°C; 2-ethylhexanoic acid (CAS: 149-57-5), boiling at 228°C; trans-2-undecenoic acid (CAS: 15790-94-0), boiling at 295°C; benzoic acid (CAS: 65-85-0), boiling at 249°C; phthalic acid (CAS: 88-99-3), boiling at 289°C; methyl nonanoate (CAS: 1731-84-6), boiling at 213°C; octyl butanoate (CAS: 1), boiling at 224°C. 10-39-4); isopropyl myristate (CAS: 110-27-0), boiling at 315°C; ethyl nicotinate (CAS: 614-18-6), boiling at 224°C; 3-hexenyl butanoate (CAS: 53398-84-8), boiling at 213°C; diethyl butanedioate (CAS: 123-25-1), boiling at 217°C; diethyl itaconate (CAS: 2409-52-1), boiling at 213°C; benzyl benzoate (CAS: 120-51-4), boiling at 323°C; methyl salicylate (CAS: 119-36-8), boiling at 222-224°C;Eugenol (CAS: 97-53-0), which boils at 252-253°C; vanillin (CAS: 121-33-5), which boils at 285-286°C; (Z)-isoeugenol (CAS: 5932-68-3), which boils at 266-268°C; ethyl anisate (CAS: 94-30-4), which boils at 263°C; 4-methylguacol (CAS: 93-51-6), which boils at 221°C; (E)-2,6-dimethoxy-4-(prop-1-en-1-yl)phenol (CAS: 20675-95-0), which boils at 305°C; thymol (CAS: 89-83-8), which boils at 232°C; caryophyllene (CAS: 87-44-5), which boils at 256-259°C; and α- Bisabolol (CAS: 515-69-5); (4R,5R)-5-butyl-4-methyloxolan-2-one (CAS: 55013-32-6), which boils at 245-247°C; (4S,5R)-5-butyl-4-methyloxolan-2-one (CAS: 39638-67-0), which boils at 246°C; β-ionone (CAS: 8013-90-9), which boils at 255°C; δ-tetradecalactone (CAS: 2721-22-4), which boils at 322°C; bis(2-furfuryl) disulfide (CAS: 4437-20-1), which boils at 229-230°C; hydrocoumarin (CAS: 119-84-6), which boils at 272°C; and coumarin (CAS: 91-64-5), which boils at 301.7°C. In most cases, the masses extracted from these molecules corresponded to the majority of the masses known to be present in the starting wood composition. Hundreds of other compounds not mentioned were also found in the tests.

[0264] The foregoing results confirm that the compositions of the present disclosure were produced in an extractor, where the condensed phase consisted of comminuted wood, the gas phase consisted of the extractor gas stream, and the molecules were any one of the molecules described in the previous paragraph.

Claims

1. 1. A composition comprising a gas phase and a condensed phase, wherein the gas phase comprises molecules; the condensed phase comprises the molecules; the gas phase has a temperature and a pressure; the molecules have a boiling point at the pressure of the gas phase; the boiling point of the molecules is higher than the temperature of the gas phase; the molecules have a vapor pressure at the temperature of the gas phase; the vapor pressure of the molecules is less than the pressure of the gas phase; the condensed phase consists of one or both of a solid phase and a liquid phase; the condensed phase is suspended in the gas phase; and the condensed phase has a surface area to volume ratio of at least 500 per meter.

2. 2. The composition of claim 1, wherein the composition has a vaporization rate for conversion of the molecules in the condensed phase to the molecules in the gas phase; the composition has a condensation rate for conversion of the molecules in the gas phase to the molecules in the condensed phase; the composition has a mass transfer rate equal to the vaporization rate minus the condensation rate; and the mass transfer rate is a positive number.

3. 3. The composition of claim 2, wherein the mass transfer rate is at least 5 micrograms of the molecule per gram of the composition per second.

4. 4. The composition of claim 2 or 3, wherein the mass transfer rate is at least 5 micrograms of said molecules per gram of said condensed phase per second.

5. 5. The composition of any one of claims 2 to 4, wherein the mass transfer rate is at least 5 micrograms of said molecules per gram of said gas phase per second.

6. The composition of any one of claims 1 to 5, wherein the temperature of the gas phase is at least 25°C.

7. The composition of any one of claims 1 to 6, wherein the temperature of the gas phase is 250°C or less.

8. The composition of any one of claims 1 to 7, wherein the temperature of the gas phase is greater than 100°C and less than or equal to 235°C.

9. The composition of any one of claims 1 to 8, wherein the condensed phase has a temperature that is lower than the temperature of the gas phase.

10. The composition of any one of claims 1 to 9, wherein the composition has a non-zero sensible heat transfer rate from the vapor phase to the condensed phase.

11. 11. The composition of any one of claims 1 to 10, wherein the composition has a sensible heat transfer rate from the vapor phase to the condensed phase of at least 2 joules per gram of the condensed phase per second.

12. 12. The composition of any one of claims 1 to 11, wherein the composition has a sensible heat transfer rate from the vapor phase to the condensed phase of 20 kilojoules per gram of the condensed phase per second or less.

13. The composition of any one of claims 1 to 12, wherein the composition has a non-zero latent heat transfer rate between the vapor phase and the condensed phase.

14. 14. The composition of any one of claims 1 to 13, wherein the composition has a latent heat transfer rate between the vapor phase and the condensed phase of at least 10 millijoules per gram of the condensed phase per second.

15. 15. The composition of any one of claims 1 to 14, wherein the composition has a latent heat transfer rate between the vapor phase and the condensed phase of no more than 2 kilojoules per gram of the condensed phase per second.

16. The composition according to any one of claims 1 to 15, wherein the gas phase has a pressure of at least 0.1 to 100 atmospheres.

17. 17. The composition of any one of claims 1 to 16, wherein the composition has an altitude; the altitude has atmospheric pressure; and the pressure of the gas phase is greater than the atmospheric pressure at the altitude.

18. 18. The composition of any one of claims 1 to 17, wherein the condensed phase has a surface area to volume ratio of at least 5000 per meter.

19. The composition of any one of claims 1 to 18, wherein the condensed phase has an average particle size of 5 millimeters or less.

20. 20. The composition of any one of claims 1 to 19, wherein the condensed phase has an average particle size of 500 micrometers or less.

21. 21. The composition of any one of claims 1 to 20, wherein the condensed phase has a mean terminal velocity of 5 meters per second or less in still, dry air at 1 atmosphere pressure.

22. The composition of any one of claims 1 to 21, wherein the composition has turbulence.

23. The composition of any one of claims 1 to 22, wherein the composition has an average Reynolds number greater than 100.

24. The composition of any one of claims 1 to 23, wherein the composition has an average Reynolds number of 1,000,000 or less.

25. The composition of any one of claims 1 to 24, wherein the composition has an average drag coefficient of at least 0.

5.

26. The composition of any one of claims 1 to 21, wherein the composition has laminar flow.

27. The composition of any one of claims 1 to 26, wherein the composition has an average velocity of at least 100 millimeters per second.

28. 28. The composition of any one of claims 1 to 27, wherein the composition has an average kinetic energy of at least 5 microjoules per gram of the composition.

29. The composition of any one of claims 1 to 28, wherein the composition has an average kinetic energy of 50 joules per gram of the composition or less.

30. 30. The composition of any one of claims 1 to 29, wherein the composition comprises at least 1 gram of the condensed phase per cubic meter of the gas phase.

31. 31. The composition of any one of claims 1 to 30, wherein the composition comprises no more than 1 gram of the condensed phase per liter of the gas phase.

32. 32. The composition of any one of claims 1 to 31, wherein the composition comprises at least 2 micrograms of the molecule per gram of the condensed phase.

33. 33. The composition of any one of claims 1 to 32, wherein the composition comprises no more than 200 milligrams of the molecule per gram of the condensed phase.

34. 34. The composition of any one of claims 1 to 33, wherein the composition comprises at least 2 micrograms of the molecule per gram of the gas phase.

35. 35. The composition of any one of claims 1 to 34, wherein the composition comprises no more than 200 milligrams of the molecule per gram of the gas phase.

36. The composition of any one of claims 1 to 35, wherein the gas phase comprises at least 10 percent of the molecules of the composition.

37. The composition of any one of claims 1 to 36, wherein the gas phase comprises at least 25 percent of the molecules of the composition.

38. The composition of any one of claims 1 to 37, wherein the gas phase comprises at least 50 percent of the molecules of the composition.

39. 39. The composition of any one of claims 1 to 38, wherein the gas phase contains a higher proportion of the molecules than the condensed phase.

40. 40. The composition of any one of claims 1 to 39, wherein the condensed phase comprises one or more polysaccharides, disaccharides, or monosaccharides.

41. The composition of any one of claims 1 to 40, wherein the condensed phase comprises cellulose I.

42. 42. The composition of any one of claims 1 to 41, wherein the condensed phase comprises a dextrin.

43. 43. The composition of any one of claims 1 to 42, wherein the condensed phase comprises a pyrodextrin.

44. 44. The composition of any one of claims 1 to 43, wherein the condensed phase comprises levoglucosan.

45. 45. The composition of any one of claims 1 to 44, wherein the condensed phase comprises one or more proteins comprising an amino acid sequence encoding a cellulose synthase.

46. 46. ​​The composition of any one of claims 1 to 45, wherein the condensed phase comprises one or more nucleic acids, nucleotides, or nucleic acid bases.

47. 47. The composition of any one of claims 1 to 46, wherein the condensed phase comprises one or more nucleic acids comprising a nucleotide sequence encoding a cellulose synthase.

48. 48. The composition of any one of claims 1 to 47, wherein the condensed phase comprises monohydrogen phosphate and dihydrogen phosphate.

49. 49. The composition of any one of claims 1 to 48, wherein the condensed phase comprises chlorophyll.

50. 50. The composition of any one of claims 1 to 49, wherein the condensed phase comprises cells.

51. 51. The composition of any one of claims 1 to 50, wherein the condensed phase comprises cells, each cell comprising a cell wall.

52. 52. The composition of any one of claims 1 to 51, wherein the condensed phase comprises cells, and the cells are plant cells.

53. 53. The composition of any one of claims 1 to 52, wherein the condensed phase comprises cells; the cells comprise intact cells, each comprising an intracellular space and an intact cell membrane that inhibits fluid communication between the intracellular space and the gas phase; and the cells comprise lysed cells, each comprising an intracellular space and a lysed cell membrane that allows fluid communication between the intracellular space and the gas phase.

54. 54. The composition of claim 53, wherein at least 10 percent of the cells are lysed cells.

55. 55. The composition of claim 53 or 54, wherein the intracellular space of each intact cell contains volatile molecules; the volatile molecules have a boiling point at the pressure of the gas phase; and the boiling point of the volatile molecules at the pressure of the gas phase is lower than the temperature of the gas phase.

56. 56. The composition of any one of claims 53 to 55, wherein the intracellular space of each intact cell contains superheated liquid.

57. 57. The composition of any one of claims 53 to 56, wherein the intracellular space of the intact cell comprises a gas.

58. 58. The composition of any one of claims 53-57, wherein the intracellular space of each intact cell contains water; the water has a boiling point at the pressure of the gas phase; and the boiling point of water at the pressure of the gas phase is lower than the temperature of the gas phase.

59. 59. The composition of any one of claims 53 to 58, wherein the intracellular space of each intact cell contains superheated water.

60. 60. The composition of any one of claims 53 to 59, wherein the intracellular space of each intact cell contains water vapor.

61. 61. The composition of any one of claims 53 to 60, wherein the intracellular space of each intact cell has a pressure greater than the pressure of the gas phase.

62. 62. The composition of any one of claims 53 to 61, wherein the composition has a non-zero cell lysis rate for converting intact cells into lysed cells.

63. 63. The composition of any one of claims 53-62, wherein said composition has a cell lysis rate for converting intact cells to lysed cells, said cell lysis rate being at least 1 percent of said cells per second.

64. 64. The composition of any one of claims 1 to 63, wherein the gas phase comprises one or more of molecular nitrogen, molecular oxygen, carbon dioxide, argon, neon, water vapor, and ethanol vapor.

65. 65. The composition of any one of claims 1 to 64, wherein the gas phase comprises the molecules and molecular nitrogen in a combined concentration of at least 50% by weight.

66. 66. The composition of any one of claims 1 to 65, wherein the gas phase is devoid of water vapor at a concentration of more than 90% by weight.

67. 65. The composition of any one of claims 1 to 64, wherein the gas phase comprises the molecules and dry vapor in a combined concentration of at least 50% by weight.

68. The molecule is acetophenone; α-bergamotol; α-bisabolol; α-bisabolol oxide A; α-cadinol; α-curcumene; α-phencene; α-Phellandrene; α-pinene; α-santalol; α-terpinene; α-terpineol; α-Terpinyl acetate; α-Thujene; ​​α-Thujone; α-Zingiberene; Azulene; Benzyl acetate; Benzyl benzoate; Bergamotene; β-Bisabolene; β-Caryophyllene; β-Damaskenone; β-Eudesmol; β-Farnesene; β-Phellandrene; β-Pinene; β-Santalol; β-Selinene; β-Sesquiphellandrene; β-Terpinene; β-Terpinyl acetate; β-Thujene; ​​β-Thujone; Borneol; Bornyl acetate; Camphene; Camphor; Capsaicin; Carene; Carvacrol; Carvone; Caryophyllene oxide; Cedrene; Cedrol; Chamazulene; Chavicol; Cinnamaldehyde; Cinnamate; Citral; Citronellal; Citronellol; Citronellyl formate; Curzerene; Cyclopentadecanolide; Decanal δ-Guaiene; Ethyl cinnamate; Eugenol; Farnesene; Farnesol; Furanoidesma-1,3-diene; Furfural; Furfuryl acetate; γ-Decalactone; γ-Muolene; γ-Nonalactone; γ-Terpinene; γ-Terpinyl acetate; Geraniol; Geranyl acetate; Germacrene A; Germacrene D; Guaiacol; Heneicosane; Humulene; Isoamyl benzoate; Kesane; Limonene; Linalool; Linalool oxide; Linalyl acetate; Lindestrene; Menthol; Menthone; Methyl cinnamate; Methyleugenol; Methylpyrazine; Myrcene; Myristin; Neral; Nerol; Nerolidol; Nootkatone; Nootkatone Chin; Nootcatol; Nootkatone; Ocimene; Octanal; Patchouli alcohol; p-cresol; p-cymene; Perylene; Phenylacetaldehyde; Phenylacetic acid; Phenylethyl alcohol; Phytol; Sabinene; Safrole; Taumulolol; Terpinen-4-ol; Terpinolene; Thymol; Valencene; Vanillin; Zingerone; Zingiberenol; Zingiberol; 1,8-cineole; 1-Phenylethyl acetate; 2,6-Dimethylpyrazine; 2-Furanmethanol; 2-Heptanol; 2-Heptanone; 2-Heptyl acetate; 2-Methoxy-4-vinylphenol; 2-Methyl-3-buten-2-ol; 2-Methylbutanoic acid; 2-nonanone; 2-pentanol; 2-pentyl acetate; 2-phenylethyl alcohol; 2-undecanone; 3-Methylbutanoic acid; 3-phenylpropanoic acid; 4-methylguaiacol; 5-methylfurfural; 6-gingerol; 6-methyl-5-hepten-2-one; 6-shogaol; acetic acid; glycerol; nonane; decane; undecane; dodecane; tridecane; tetradecane; pentadecane; 1-octanol; 3-octanol; 1-nonanol; pentanal; hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; tetradecanal; isobutyraldehyde; 4-ethylbenzaldehyde; 2-decanone; dec-3-en-5-one; 2-undecanone; 2-dodecanone; 2-tridecanone; 2-tetradecanone; 2-pentadecanone; 3-Octanone; 2-Methylhept-2-en-6-one; 6,10-dimethylundecan-2-one; 6,1-,14-trimethylpentadecan-2-one; 2,2,6-trimethylcyclohexanone; 2,2,6-trimethylcyclohexan-5-enone; caproic acid; 68. The composition of any one of claims 1 to 67, wherein the acid is caprylic acid; capric acid; lauric acid; myristic acid; palmitic acid; or hexyl acetate.

69. 69. The composition of claim 68, wherein the molecule is acetophenone.

70. 69. The composition of claim 68, wherein the molecule is α-bergamitol.

71. 69. The composition of claim 68, wherein the molecule is α-bisabolol.

72. 69. The composition of claim 68, wherein the molecule is α-bisabolol oxide A.

73. 69. The composition of claim 68, wherein the molecule is α-cadinol.

74. 69. The composition of claim 68, wherein the molecule is α-curcumene.

75. 69. The composition of claim 68, wherein the molecule is α-fenchen.

76. 69. The composition of claim 68, wherein the molecule is α-phellandrene.

77. 69. The composition of claim 68, wherein the molecule is alpha-pinene.

78. 69. The composition of claim 68, wherein the molecule is α-santalol.

79. 69. The composition of claim 68, wherein the molecule is alpha-terpinene.

80. 69. The composition of claim 68, wherein the molecule is alpha-terpineol.

81. 69. The composition of claim 68, wherein the molecule is alpha-terpinyl acetate.

82. 69. The composition of claim 68, wherein the molecule is alpha-thujene.

83. 69. The composition of claim 68, wherein the molecule is alpha-thujone.

84. 69. The composition of claim 68, wherein the molecule is alpha-zingiberene.

85. 69. The composition of claim 68, wherein the molecule is azulene.

86. 69. The composition of claim 68, wherein the molecule is benzyl acetate.

87. 69. The composition of claim 68, wherein the molecule is benzyl benzoate.

88. 69. The composition of claim 68, wherein the molecule is bergamotene.

89. 69. The composition of claim 68, wherein the molecule is β-bisabolene.

90. 69. The composition of claim 68, wherein the molecule is β-caryophyllene.

91. 69. The composition of claim 68, wherein the molecule is β-damascenone.

92. 69. The composition of claim 68, wherein the molecule is β-eudesmol.

93. 69. The composition of claim 68, wherein the molecule is β-farnesene.

94. 69. The composition of claim 68, wherein the molecule is β-phellandrene.

95. 69. The composition of claim 68, wherein the molecule is β-pinene.

96. 69. The composition of claim 68, wherein the molecule is β-santalol.

97. 69. The composition of claim 68, wherein the molecule is β-selinene.

98. 69. The composition of claim 68, wherein the molecule is β-sesquiphellandrene.

99. 69. The composition of claim 68, wherein the molecule is β-terpinene.

100. 69. The composition of claim 68, wherein the molecule is β-terpinyl acetate.

101. 69. The composition of claim 68, wherein the molecule is β-thujene.

102. 69. The composition of claim 68, wherein the molecule is β-thujone.

103. 69. The composition of claim 68, wherein the molecule is borneol.

104. 69. The composition of claim 68, wherein the molecule is bornyl acetate.

105. 69. The composition of claim 68, wherein the molecule is camphene.

106. 69. The composition of claim 68, wherein the molecule is camphor.

107. 69. The composition of claim 68, wherein the molecule is capsaicin.

108. 69. The composition of claim 68, wherein the molecule is carene.

109. 69. The composition of claim 68, wherein the molecule is carvacrol.

110. 69. The composition of claim 68, wherein the molecule is carvone.

111. 69. The composition of claim 68, wherein the molecule is caryophyllene oxide.

112. 69. The composition of claim 68, wherein the molecule is cedrene.

113. 69. The composition of claim 68, wherein the molecule is cedrol.

114. 69. The composition of claim 68, wherein the molecule is chamazulene.

115. 69. The composition of claim 68, wherein the molecule is chavicol.

116. 69. The composition of claim 68, wherein the molecule is cinnamaldehyde.

117. 69. The composition of claim 68, wherein the molecule is citral.

118. 69. The composition of claim 68, wherein the molecule is citronellal.

119. 69. The composition of claim 68, wherein the molecule is citronellol.

120. 69. The composition of claim 68, wherein the molecule is citronellyl formate.

121. 69. The composition of claim 68, wherein the molecule is curzeren.

122. 69. The composition of claim 68, wherein the molecule is cyclopentadecanolide.

123. 69. The composition of claim 68, wherein the molecule is decanal.

124. 69. The composition of claim 68, wherein the molecule is delta-guaiene.

125. 69. The composition of claim 68, wherein the molecule is ethyl cinnamate.

126. 69. The composition of claim 68, wherein the molecule is eugenol.

127. 69. The composition of claim 68, wherein the molecule is farnesene.

128. 69. The composition of claim 68, wherein the molecule is farnesol.

129. 69. The composition of claim 68, wherein the molecule is furanoeudesma-1,3-diene.

130. 69. The composition of claim 68, wherein the molecule is furfural.

131. 69. The composition of claim 68, wherein the molecule is furfuryl acetate.

132. 69. The composition of claim 68, wherein the molecule is gamma-decalactone.

133. 69. The composition of claim 68, wherein the molecule is gamma-muurolene.

134. 69. The composition of claim 68, wherein the molecule is gamma-nonalactone.

135. 69. The composition of claim 68, wherein the molecule is gamma-terpinene.

136. 69. The composition of claim 68, wherein the molecule is gamma-terpinyl acetate.

137. 69. The composition of claim 68, wherein the molecule is geraniol.

138. 69. The composition of claim 68, wherein the molecule is geranyl acetate.

139. 69. The composition of claim 68, wherein the molecule is germacrene A.

140. 69. The composition of claim 68, wherein the molecule is germacrene D.

141. 69. The composition of claim 68, wherein the molecule is guaiacol.

142. 69. The composition of claim 68, wherein the molecule is heneicosane.

143. 69. The composition of claim 68, wherein the molecule is humulene.

144. 69. The composition of claim 68, wherein the molecule is isoamyl benzoate.

145. 69. The composition of claim 68, wherein the molecule is kessane.

146. 69. The composition of claim 68, wherein the molecule is limonene.

147. 69. The composition of claim 68, wherein the molecule is linalool.

148. 69. The composition of claim 68, wherein the molecule is linalool oxide.

149. 69. The composition of claim 68, wherein the molecule is linalyl acetate.

150. 69. The composition of claim 68, wherein the molecule is menthol.

151. 69. The composition of claim 68, wherein the molecule is menthone.

152. 69. The composition of claim 68, wherein the molecule is methyl cinnamate.

153. 69. The composition of claim 68, wherein the molecule is methyl eugenol.

154. 69. The composition of claim 68, wherein the molecule is methylpyrazine.

155. 69. The composition of claim 68, wherein the molecule is myrcene.

156. 69. The composition of claim 68, wherein the molecule is myristicin.

157. 69. The composition of claim 68, wherein the molecule is neral.

158. 69. The composition of claim 68, wherein the molecule is nerol.

159. 69. The composition of claim 68, wherein the molecule is nerolidol.

160. 69. The composition of claim 68, wherein the molecule is nocatone.

161. 69. The composition of claim 68, wherein the molecule is nootcatin.

162. 69. The composition of claim 68, wherein the molecule is nootcatol.

163. 69. The composition of claim 68, wherein the molecule is nootkatone.

164. 69. The composition of claim 68, wherein the molecule is ocimene.

165. 69. The composition of claim 68, wherein the molecule is octanal.

166. 69. The composition of claim 68, wherein the molecule is para-cresol.

167. 69. The composition of claim 68, wherein the molecule is para-cymene.

168. 69. The composition of claim 68, wherein the molecule is patchouli alcohol.

169. 69. The composition of claim 68, wherein the molecule is perylene.

170. 69. The composition of claim 68, wherein the molecule is phenylacetaldehyde.

171. 69. The composition of claim 68, wherein the molecule is phenylacetic acid.

172. 69. The composition of claim 68, wherein the molecule is phenylethyl alcohol.

173. 69. The composition of claim 68, wherein the molecule is phytol.

174. 69. The composition of claim 68, wherein the molecule is sabinene.

175. 69. The composition of claim 68, wherein the molecule is safrole.

176. 69. The composition of claim 68, wherein the molecule is thau-muurol.

177. 69. The composition of claim 68, wherein the molecule is terpinen-4-ol.

178. 69. The composition of claim 68, wherein the molecule is terpinolene.

179. 69. The composition of claim 68, wherein the molecule is thymol.

180. 69. The composition of claim 68, wherein the molecule is valencene.

181. 69. The composition of claim 68, wherein the molecule is vanillin.

182. 69. The composition of claim 68, wherein the molecule is zingerone.

183. 69. The composition of claim 68, wherein the molecule is zingiberenol.

184. 69. The composition of claim 68, wherein the molecule is zingiberol.

185. 69. The composition of claim 68, wherein the molecule is 1,8-cineole.

186. 69. The composition of claim 68, wherein the molecule is 1-phenylethyl acetate.

187. 69. The composition of claim 68, wherein the molecule is 2,6-dimethylpyrazine.

188. 69. The composition of claim 68, wherein the molecule is 2-furanmethanol.

189. 69. The composition of claim 68, wherein the molecule is 2-heptanol.

190. 69. The composition of claim 68, wherein the molecule is 2-heptanone.

191. 69. The composition of claim 68, wherein the molecule is 2-heptyl acetate.

192. 69. The composition of claim 68, wherein the molecule is 2-methoxy-4-vinylphenol.

193. 69. The composition of claim 68, wherein the molecule is 2-methyl-3-buten-2-ol.

194. 69. The composition of claim 68, wherein the molecule is 2-methylbutanoic acid.

195. 69. The composition of claim 68, wherein the molecule is 2-nonanone.

196. 69. The composition of claim 68, wherein the molecule is 2-pentanol.

197. 69. The composition of claim 68, wherein the molecule is 2-pentyl acetate.

198. 69. The composition of claim 68, wherein the molecule is 2-phenylethyl alcohol.

199. 69. The composition of claim 68, wherein the molecule is 2-undecanone.

200. 69. The composition of claim 68, wherein the molecule is 3-methylbutanoic acid.

201. 69. The composition of claim 68, wherein the molecule is 3-phenylpropanoic acid.

202. 69. The composition of claim 68, wherein the molecule is 4-methylguaiacol.

203. 69. The composition of claim 68, wherein the molecule is 5-methylfurfural.

204. 69. The composition of claim 68, wherein the molecule is 6-gingerol.

205. 69. The composition of claim 68, wherein the molecule is 6-methyl-5-hepten-2-one.

206. 69. The composition of claim 68, wherein the molecule is 6-shogaol.

207. 69. The composition of claim 68, wherein the molecule is phenylacetaldehyde oxime.

208. 69. The composition of claim 68, wherein the molecule is dihydrofarnesal.

209. 68. The composition of any one of claims 1 to 67, wherein the molecule is furyl-hydroxymethyl ketone.

210. 68. The composition of any one of claims 1 to 67, wherein the molecule is 2-methyl-benzofuran.

211. 68. The composition of any one of claims 1 to 67, wherein the molecule is 2-(2-furanylmethyl)-5-methyl-furan.

212. The composition of any one of claims 1 to 67, wherein the molecule is 2,5-furandicarboxaldehyde.

213. 68. The composition of any one of claims 1 to 67, wherein the molecule is nonan-1-ol.

214. 68. The composition of any one of claims 1 to 67, wherein the molecule is decan-1-ol.

215. 68. The composition of any one of claims 1 to 67, wherein the molecule is dodecan-1-ol.

216. 68. The composition of any one of claims 1 to 67, wherein the molecule is tetradecan-1-ol.

217. 68. The composition of any one of claims 1 to 67, wherein the molecule is hexadecan-1-ol.

218. 68. The composition of any one of claims 1 to 67, wherein the molecule is octadecan-1-ol.

219. 68. The composition of any one of claims 1 to 67, wherein the molecule is nonen-3-ol.

220. 68. The composition of any one of claims 1 to 67, wherein the molecule is 2-decen-1-ol.

221. 68. The composition of any one of claims 1 to 67, wherein the molecule is tetradecanal.

222. 68. The composition of any one of claims 1 to 67, wherein the molecule is (Z)-2-decenal.

223. 68. The composition of any one of claims 1 to 67, wherein the molecule is (E,E)-2,4-decadienal.

224. 68. The composition of any one of claims 1 to 67, wherein the molecule is octanoic acid.

225. 68. The composition of any one of claims 1 to 67, wherein the molecule is nonanoic acid.

226. 68. The composition of any one of claims 1 to 67, wherein the molecule is n-decanoic acid.

227. 68. The composition of any one of claims 1 to 67, wherein the molecule is n-hexadecanoic acid.

228. 68. The composition of any one of claims 1 to 67, wherein the molecule is heptadecanoic acid.

229. 68. The composition of any one of claims 1 to 67, wherein the molecule is octadecanoic acid.

230. 68. The composition of any one of claims 1 to 67, wherein the molecule is 2-ethylhexanoic acid.

231. 68. The composition of any one of claims 1 to 67, wherein the molecule is trans-2-undecenoic acid.

232. 68. The composition of any one of claims 1 to 67, wherein the molecule is benzoic acid.

233. 68. The composition of any one of claims 1 to 67, wherein the molecule is a phthalic acid.

234. 68. The composition of any one of claims 1 to 67, wherein the molecule is methyl nonanoate.

235. 68. The composition of any one of claims 1 to 67, wherein the molecule is octyl butanoate.

236. 68. The composition of any one of claims 1 to 67, wherein the molecule is isopropyl myristate.

237. 68. The composition of any one of claims 1 to 67, wherein the molecule is ethyl nicotinate.

238. 68. The composition of any one of claims 1 to 67, wherein the molecule is 3-hexenyl butanoate.

239. 68. The composition of any one of claims 1 to 67, wherein the molecule is diethyl butanedioate.

240. 68. The composition of any one of claims 1 to 67, wherein the molecule is diethyl itaconate.

241. 68. The composition of any one of claims 1 to 67, wherein the molecule is methyl salicylate.

242. 68. The composition of any one of claims 1 to 67, wherein the molecule is (Z)-isoeugenol.

243. 68. The composition of any one of claims 1 to 67, wherein the molecule is ethyl anisate.

244. 68. The composition of any one of claims 1 to 67, wherein the molecule is 4-methylguacol.

245. 68. The composition of any one of claims 1 to 67, wherein the molecule is (E)-2,6-dimethoxy-4-(prop-1-en-1-yl).

246. The composition of any one of claims 1 to 67, wherein the molecule is a phenol.

247. 68. The composition of any one of claims 1 to 67, wherein the molecule is 1,3,8-p-menthatriene.

248. 68. The composition of any one of claims 1 to 67, wherein the molecule is caffeine.

249. 68. The composition of any one of claims 1 to 67, wherein the molecule is nicotine.

250. 68. The composition of any one of claims 1 to 67, wherein the molecule is 1H-pyrrole-2-carboxaldehyde.

251. 68. The composition of any one of claims 1 to 67, wherein the molecule is a phytosterol.

252. 68. The composition of any one of claims 1 to 67, wherein the molecule is (4R,5R)-5-butyl-4-methyloxolan-2-one.

253. 68. The composition of any one of claims 1 to 67, wherein the molecule is (4S,5R)-5-butyl-4-methyloxolan-2-one.

254. 68. The composition of any one of claims 1 to 67, wherein the molecule is β-ionone.

255. 68. The composition of any one of claims 1 to 67, wherein the molecule is δ-tetradecalactone.

256. 68. The composition of any one of claims 1 to 67, wherein the molecule is bis(2-furfuryl) disulfide.

257. 68. The composition of any one of claims 1 to 67, wherein the molecule is a hydrocoumarin.

258. 68. The composition of any one of claims 1 to 67, wherein the molecule is a coumarin.

259. The molecule may be a cannabinoid carboxylic acid, tetrahydrocannabinolic acid, tetrahydrocannabivarin carboxylic acid, tetrahydrocannabiolic acid, cannabidiolic acid, cannabidivarin carboxylic acid, cannabidiolic acid, cannabichromene acid, cannabichromevaric acid, cannabigerolic acid, cannabigerovaric acid, cannabicycloic acid, cannabiersoic acid, perotetinenic acid, cannabinolic acid, cannabivarin carboxylic acid, a carboxylate salt of any one of the preceding molecules, cannabinoid, tetrahydrocannabinol, tetrahydrocannabivarin, tetrahydrocannabiol, cannabidiol, cannabidivarin, cannabidiol chol, canna 259. The composition of any one of claims 1 to 258, which is not nabichromene, cannabichromevarin, cannabigerol, cannabigerovarin, cannabicyclol, cannabielsoin, perotetinene, cannabinol, cannabivarin, a naturally occurring ether of any one of the preceding molecules, a stereoisomer of any one of the preceding molecules, β-caryophyllene, humulene, (-)-guaiol, (-)-α-bisabolol, linalool, α-terpineol, caryophyllene oxide, myrcene, eucalyptol, limonene, nerolidol, α-terpinene, borneol, (-)-isopulegol, δ-3-carene, para-cymene, or terpinolene.

260. 260. The composition of any one of claims 1 to 259, wherein the composition is devoid of cannabis and any chemical species derived from cannabis.

261. The composition of any one of claims 1 to 260, wherein the boiling point of the molecule at the pressure of the gas phase is at least 10°C higher than the temperature of the gas phase.

262. The composition of any one of claims 1 to 261, wherein the boiling point of the molecule at the pressure of the gas phase is at least 100°C higher than the temperature of the gas phase.

263. The composition of any one of claims 1 to 262, wherein the condensed phase comprises wood.

264. The composition of any one of claims 1 to 263, wherein the condensed phase comprises sawdust.

265. The composition of any one of claims 1 to 264, wherein the condensed phase comprises a core material.

266. The composition of any one of claims 1 to 265, wherein the condensed phase comprises softwood.

267. The composition of any one of claims 1 to 266, wherein the condensed phase comprises pine wood.

268. The composition of any one of claims 1 to 266, wherein the condensed phase comprises fir wood.

269. The composition of any one of claims 1 to 266, wherein the condensed phase comprises spruce wood.

270. The composition of any one of claims 1 to 266, wherein the condensed phase comprises cedar wood.

271. 266. The composition of any one of claims 1 to 265, wherein the condensed phase comprises angiosperm material.

272. The composition of any one of claims 1 to 265, wherein the condensed phase comprises oak wood.

273. The composition of any one of claims 1 to 265, wherein the condensed phase comprises chestnut wood.

274. 272. The composition of any one of claims 1 to 265 and 271, wherein the condensed phase comprises sandalwood.

275. 272. The composition of any one of claims 1 to 265 and 271, wherein the condensed phase comprises maple wood.

276. 272. The composition of any one of claims 1 to 265 and 271, wherein the condensed phase comprises walnut wood.

277. 272. The composition of any one of claims 1 to 265 and 271, wherein the condensed phase comprises ash wood.

278. 272. The composition of any one of claims 1 to 265 and 271, wherein the condensed phase comprises cachaça wood.

279. 272. The composition of any one of claims 1 to 265 and 271, wherein the condensed phase comprises ambrana wood.

280. 272. The composition of any one of claims 1 to 265 and 271, wherein the condensed phase comprises sandalwood (Santalum) wood.

281. The composition of any one of claims 1 to 262, wherein the condensed phase comprises plant milk biomass.

282. 279. The composition of any one of claims 1 to 262 and 278, wherein the condensed phase comprises biomass of lily of the valley, lilac, broomrape, violet, rubber tree, hyacinth, or sweet pea.

283. 279. The composition of any one of claims 1 to 262, 278, and 279, wherein the condensed phase comprises lily of the valley biomass.

284. 1. A method for separating a molecule from an impurity, the method comprising: providing a composition comprising the molecule and the impurity, wherein the molecule is present in the composition in a solid or liquid phase, and the impurity is present in the composition in a solid or liquid phase; converting the molecule to a vaporized molecule in a gas phase, wherein the gas phase has a pressure and a temperature, the molecule has a boiling point at the pressure and a vapor pressure at the temperature, the pressure of the gas phase is greater than the vapor pressure of the molecule, the boiling point of the molecule is greater than the temperature of the gas phase, and the impurity lacks vapor pressure or has a vapor pressure at a temperature lower than the vapor pressure of the molecule at the temperature; separating the vaporized molecule from the impurity, and condensing the vaporized molecule to a condensed molecule.

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