WO2020219826A1

WO2020219826A1 - Process of extracting useful materials from cannabis plants

Info

Publication number: WO2020219826A1
Application number: PCT/US2020/029741
Authority: WO
Inventors: Joshua MAYO; Aaron RIEDER
Original assignee: Taba Ip, Llc
Priority date: 2019-04-24
Filing date: 2020-04-24
Publication date: 2020-10-29

Abstract

The present disclosure is generally directed to methods for extracting useful materials from Cannabis plants. Particularly, the present disclosure is directed to extracting Cannabis plant oils from Cannabis plant materials.

Description

PROCESS OF EXTRACTING USEFUL MATERIALS FROM CANNABIS PLANTS

CROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of priority of U.S. Provisional Patent Application No. 62/838,133, filed April 24, 2019, which is incorporated by reference in its entirety.

BACKGROUND OF THE DISCLOSURE

Field of the Invention

[0002] The present disclosure is generally directed to methods for extracting useful materials from Cannabis plants. Particularly, the present disclosure is directed to extracting Cannabis plant oils from Cannabis plant materials.

Description of the Related Art

[0003] Every individual has an endocannabinoid system comprised of chemical receptors in the brain, immune system, and central nervous system, for example, cannabinoid 1 (CB1 ) receptor and cannabinoid 2 (CB2) receptor. CB1 and CB2 receptors are members of the G protein-coupled receptor (GPCR) superfamily. The CB1 receptor is expressed in the central nervous system (CNS), lungs, liver, adipose tissue, and kidneys, and the CB2 receptor is mainly localized in immune cells and on cells that are involved in bone formation and bone loss. These receptors have been associated with many human diseases including obesity, diabetes, fibrosis, liver diseases, cardiovascular disease, cancer, pain, MS spasticity, and glaucoma, among others.

[0004] Cannabinoids are compounds active on cannabinoid receptors in humans and have been implicated in many of the pharmacological benefits on the diseases noted above. Cannabinoids of plant origin, also known as phytocannabinoids, are abundant in Cannabis. Medical use of cannabis and associated phytocannabinoids is becoming widely accepted in the United States as an alternative form of medicine. Many states have legalized its use for qualified medical conditions such as chronic pain, epilepsy, sleep disorders, anxiety, cancer, glaucoma, nausea, amyotrophic lateral sclerosis (ALS), Alzheimer’s disease, Crohn’s disease, Post-traumatic Stress Disorder (PTSD), arthritis, fibromyalgia, and others. [0005] One of the most common ways that cannabis is used for medicinal use in many countries is through smoking. Although proven to be beneficial in certain indications, smoking medical cannabis has disadvantages. For example, the smoke from the plant matter comprises carcinogens and other toxins in addition to the desired cannabinoids. Heavy cannabis use through smoking has also been associated with accelerated pulmonary decline, lung damage, and emphysema. Another disadvantage of smoking medical cannabis is difficulty in maintaining control over the proper dosing of medicinal cannabis due to active ingredients fluctuations (e.g., the amounts of active ingredients may differ depending on the differences present in plant varietals as well as changing growing conditions which result in intravarietal variations.) Finally, consumption through smoking has a relatively low bioavailability of target compounds compared to other delivery methods.

[0006] A less common way to utilize cannabis for medical use is to extract beneficial cannabinoids from cannabis. Many purification processes have been developed for isolating and purifying cannabinoids but many of these purification processes require starting from Cannabis oil or Cannabis extract relatively high in cannabinoids content, which in turn are obtained from raw plant material or plant resin.

[0007] Because raw plant materials or plant resins typically contain only small quantities of desired cannabinoids, the current methods for obtaining Cannabis oil or extract generally employ large-scale processes using hydrocarbons, alcohols, or supercritical fluids in the extraction process. There are benefits and limitations to each of these methods that impact the throughput, efficiency, and yield percentage.

[0008] The use of supercritical fluids, such as carbon dioxide, to carry out the extraction has been utilized for several years throughout the industry. In general, such extraction takes a minimum of several hours to complete. But in order to produce a high quality (palatable) oil, the extraction process is usually carried out for up to 22 hours. This method regularly produces a yield of 10% to 12% from dry weight of raw plant material. The yield can be increased by extending the extraction time even further; however, the resulting oil commonly contains a larger amount of biomass contaminants thereby decreasing the quality of the oil. [0009] The use of alcohols, specifically ethanol, for the extraction is a common method and often touted for high throughput and yield. But in order to maximize the yield, alcohol solvent is generally passed over the plant material multiple times. With each pass over the plant material, more biomass contaminants end up in the solvent. The multiple pass method also extends the extraction time required to carry out the extraction. Additionally, the removal of alcohols during post-extraction processing requires more energy (heat) that affects the aroma and flavor profile of the oil by also evaporating the desired constituents from the oil during the solvent removal.

[0010] Traditional hydrocarbon extractions are done at subzero temperatures, which in turn influences the quality and yield of the process. Low temperature hydrocarbon extractions result in cannabis oil that is pale in color, flavorful, and aromatic, but low yields. The typical run times for these extractions range from 45 minutes to 130 minutes, depending on whether in-line dewaxing of the final product is used. Typical hydrocarbons used are propane and butane, often in combination where butane is the dominant solvent to increase yield. Other hydrocarbons may include hextane, pentane, and heptane, although these solvents are used less frequently due to concerns regarding the solvent removal process.

[0011] In general, currently available extractions, whether at cold temperatures or room temperature, see a yield of 4% from wet plant material. Therefore, there exists a need for simple, economical, and reliable methods that provide Cannabis oil or extract in high yield, without sacrificing flavor or aroma.

SUMMARY OF THE DISCLOSURE

[0012] The disclosure provides methods for obtaining Cannabis plant oil from a Cannabis plant material. Such methods generally include:

providing one or more solvents selected from propane, butane, and combination

thereof to the Cannabis plant material to obtain a slurry;

brining the slurry to a target temperature in the range of -10 °C to 70 °C and

maintaining the slurry at the target temperature for a time sufficient to extract target mixture from the plant material;

separating the target mixture from the remaining plant material; and

cooling the target mixture to a temperature in the range of -75 °C to -20 °C for a time sufficient to obtain the Cannabis plant oil. [0013] Another aspect of the disclosure provides a Cannabis plant oil prepared according to method of the disclosure as described herein.

[0014] In certain embodiments of this aspect, the Cannabis plant oil comprises tetrahydrocannabinolic acid (THCA, THCa, A⁹-tetrahydrocannabinolic acid, or A⁹- THCA), cannabidiolic acid (CBDA or CBDa), cannabidiol (CBD),

tetrahydrocannabivarin (THCV or THV), or a combination thereof. In certain embodiments of this aspect, the Cannabis plant oil comprises tetrahydrocannabinolic acid.

[0015] In certain embodiments, the Cannabis plant oil prepared according to method of the disclosure as described herein comprises at least 70%, based on the total weight of the oil, of tetrahydrocannabinolic acid.

[0016] In certain embodiments, the Cannabis plant oil prepared according to method of the disclosure as described herein comprises at least 2%, based on the total weight of the oil, of one or more terpenes and/or terpenoids.

DETAILED DESCRIPTION

[0017] In view of the present disclosure, the methods and compositions described herein can be configured by the person of ordinary skill in the art to meet the desired need. In general, the disclosed methods and compositions provide improvements in extraction of Cannabis plant oil from Cannabis plant materials. Specifically, the inventors found that subjecting the plant material to hydrocarbon solvents at high temperatures allows for improved yield of Cannabis plant oil. Thus, method of the disclosure, in certain embodiments, is efficient and economical as it obtains higher amount of plant oil than the amount obtained using traditional hydrocarbon methods. In addition, the Cannabis plant oil obtained by the method of the disclosure has a high content of desired components, such as THCA, THCV, and other cannabinoids, terpenes and/or terpenoids. Thus, in certain embodiments, the Cannabis plant oil obtained by the method of the disclosure is also flavorful and aromatic. Furthermore, in certain embodiments, the Cannabis plant oil obtained by the method of the disclosure, when subjected to crystallization conditions, can nucleate and crystalize THCA and/or THCV on a much reduced timeline (e.g., about 24 hours vs. 20 days). [0018] In contrast, the current commercial and known purification methods utilizing hydrocarbon solvents require negative temperatures, e.g., less than 0 °C and usually between -80 °C and -20 °C. To date, the hydrocarbon solvents, such as propane and butane, have not been used for high temperature (e.g., more than 0 °C) extractions because such extractions are considered to have major drawbacks. Specifically, safety concerns and increased contamination of the Cannabis plant oil with lipids, general biomass and color contaminants are provided as reasons against using hydrocarbons for high temperature extractions.

[0019] Accordingly, one aspect of the disclosure provides a method of obtaining a Cannabis plant oil from a Cannabis plant material, the method including:

providing one or more solvents selected from propane, butane, and combination thereof to the Cannabis plant material to obtain a slurry;

separating the target mixture from the remaining plant material; and

cooling the target mixture to a temperature in the range of -75 °C to -20 °C for a time sufficient to obtain the Cannabis plant oil.

[0020] One of skill in the art recognizes that any part of the plant having desired cannabinoid content may be used in the methods of the disclosure. For example, the plant material may be obtained from trichomes, flowers, leaves, inflorescences, stalks, buds, seeds, flower trimmings, etc. In certain embodiments, the plant material is raw wet plant material (i.e. , plant material that has been subjected to mechanical manipulation but not dried). In certain embodiments, the plant material is raw dried plant material (i.e., plant material that has been subjected to mechanical manipulation and dried). In certain embodiments, the plant material is resin, including but not limited to kief and hashish.

[0021] In certain embodiments, the plant material is Cannabis flowers.

[0022] In certain embodiments, the plant material is Cannabis flowers trimmings.

[0023] As noted above, the methods include providing one or more solvents to the Cannabis plant material. The one or more solvents of the invention includes propane, butane (n-butane or /-butane), and combination thereof. [0024] In certain embodiments of the method of the disclosure as described herein, the one or more solvents is propane.

[0025] In certain embodiments of the method of the disclosure as described herein, the one or more solvents is butane (e.g., n-butane or /-butane).

[0026] In the methods of the disclosure as disclosed herein, in certain

embodiments, the one or more solvents is a combination of propane and butane. In certain embodiments, the one or more solvents is a combination of propane and n- butane. In certain embodiments, propane and butane (e.g., n-butane) are provided in a weight ratio in a range of 95:5 and 50:50. In certain ambodiments, the weight ratio of propane and butane is in a range of 95:5 and 60:40. In certain ambodiments, the weight ratio of propane and butane is in a range of 95:5 and 70:30. In certain ambodiments, the weight ratio of propane and butane is in a range of 95:5 and 80:20. In certain ambodiments, the weight ratio of propane and butane is in a range of 95:5 and 85:15. In certain embodiments, propane and butane (e.g., n-butane) are provided in a weight ratio in a range of about 90:10.

[0027] In certain embodiments, the one or more solvents are provided at low temperature, such as the temperature below the boiling point of the one or more solvents. In certain embodiments, the one or more solvents is provided at a temperature in a range of -70 °C to -30 °C, e.g., in a range of -60 °C to -30 °C, or -50 °C to -30 °C, or -40 °C to -30 °C. In certain embodiments, the one or more solvents is provided at a temperature in a range of -70 °C to -40 °C, e.g., in a range of -60 °C to -40 °C, or -50 °C to -40 °C. In certain embodiments, the one or more solvents is provided at a temperature in a range of -70 °C to -50 °C, e.g, in a range of -60 °C to -50 °C. In certain embodiments, the one or more solvents is provided at a temperature in a range of -45 °C to -35 °C. In certain embodiments, the one or more solvents is provided at a temperature in a range of -42 °C to -38 °C. In certain embodiments, the one or more solvents is provided at a temperature of about -40 °C; or about -50 °C; or about -60 °C; or about -65 °C; or about -70 °C.

[0028] The Cannabis plant material and the one or more solvents, in certain embodiments of the methods of the disclosure, are provided in a weight ratio in a range of 1 :1 and 1 :20, e.g., in a range of 1 :2 and 1 :20, or 1 :4 and 1 :20, or 1 :5 and 1 :20, or 1 : 10 and 1 :20, or 1 : 15 and 1 :20. In certain embodiments, the Cannabis plant material and the one or more solvents are provided in a weight ratio or in a range of 1 :1 and 1 :15, e.g., in a range of 1 :2 and 1 :15, or 1 :4 and 1 :15, or 1 :5 and 1 :15, or 1 :10 and 1 :15. In certain embodiments, the Cannabis plant material and the one or more solvents are provided in a weight ratio in a range of 1 :1 and 1 :10, e.g., in a range of 1 :2 and 1 :10, or 1 :4 and 1 :10, or 1 :5 and 1 :10. In certain embodiments, the Cannabis plant material and the one or more solvents are provided in a weight ratio in a range of 1 : 1 and 1 :5, for example, in a range of 1 :2 and 1 :5, or in a range of 1 :4 and 1 :5. In certain embodiments, the Cannabis plant material and the one or more solvents are provided in a weight ratio in a range of 1 :4 and 1 :7. In certain embodiments, the Cannabis plant material and the one or more solvents are provided in a weight ratio in a range of 1 :8 and 1 :12, for example in a range of 1 :9 and 1 :11. In certain embodiments, the Cannabis plant material and the one or more solvents are provided in a weight ratio of about 1 :10.

[0029] In the methods of the disclosure as provided herein, the Cannabis plant material and the one or more solvents form a slurry. The slurry is then brought up to a target temperature in the range of -10 °C to 70 °C.

[0030] In certain embodiments of the methods of the disclosure, the target temperature is in the range of 20 °C to 70 °C, for example in the range of 20 °C to 60 °C, or 20 °C to 50 °C. In certain embodiments, the target temperature is in the range of 30 °C to 70 °C, e.g, in the range of 30 °C to 60 °C, or 30 °C to 50 °C. In certain embodiments, the target temperature is in the range of 10 °C to 50 °C, for example in the range of 10 °C to 40 °C or 10 °C to 30 °C. In certain embodiments, the target temperature is in the range of 40 °C to 70 °C, e.g., in the range of 40 °C to 60 °C, or 40 °C to 50 °C. In certain embodiments of the methods of the disclosure, the target temperature is in the range of 30 °C to 50 °C.

[0031] In general, bringing the slurry to the target temperature is by controlled heating. For example, controlled heating is achieved with a hating rate in a range of 0.5 °C/min to 3 °C/min and pressure in a range of 2 atm to 35 atm. In certain embodiments, the hating rate in a range of 1 °C/min to 2.5 °C/min; or 1.5 °C/min to 2.5 °C/min; or 2 °C/min to 2.5 °C/min; or 0.5 °C/min to 2 °C/min; or 1 °C/min to 2 °C/min; or 1.5 °C/min to 2 °C/min. In certain embodiments, the pressure is provided herein. [0032] In the methods of the disclosure as provided herein, bringing the slurry to the target temperature and/or maintaining the slurry at the target temperature can be performed at pressures of more than 1 atm (e.g., more than 1.5 atm, or 2 atm, or 10 atm, or even 20 atm). For example, in certain embodiments, the pressure is in the range of 2 atm to 35 atm, e.g., in the range of 2 atm to 30 atm, or 2 atm to 20 atm, or 2 atm to 15 atm, or 2 atm to 10 atm, or 2 atm to 5 atm. In certain embodiments, the pressure is in the range of 3 atm to 35 atm, e.g., in the range of 3 atm to 30 atm, or 3 atm to 20 atm, or 3 atm to 15 atm, or 3 atm to 10 atm, or 3 atm to 5 atm. In certain embodiments, the pressure is in the range of 5 atm to 35 atm, e.g., in the range of 5 atm to 30 atm, or 5 atm to 20 atm, or 5 atm to 10 atm. In certain embodiments, the pressure is about 2 atm; or about 3 atm; or about 5 atm. In certain embodiments, the pressure is in the range of 15 atm to 35 atm, e.g., in the range of 20 atm to 35 atm, or 25 atm to 35 atm; or 30 atm to 35 atm. In certain embodiments, the pressure is in the range of 15 atm to 30 atm, e.g., in the range of 20 atm to 30 atm, or 25 atm to 30 atm.

[0033] In certain embodiments of the methods of the disclosure as described herein, the slurry is brought to the target temperature in the range of 30 °C to 50 °C and a pressure of more than 1 atm as provided herein.

[0034] In certain embodiments of the methods of the disclosure, the target temperature is in the range of -10 °C to 0 °C, for example, in the range of -10 °C to -4 °C, or -10 °C to -5 °C, or -10 °C to -8 °C. In certain embodiments of the methods of the disclosure, the target temperature is about -10 °C, e.g., about -4 °C or about 0 °C.

[0035] In certain embodiments of the methods of the disclosure as described herein, the slurry is brought to the target temperature in the range of -10 °C to 0 °C and a pressure of more than 1 atm (e.g., 1.5 atm or 2 atm).

[0036] The slurry is maintained at the target temperature for a period of time sufficient to extract target mixture from the plant material. In certain embodiments, the slurry is maintained at the target temperature for a period of 30 min to 5 hours; for example, for a period of 30 min to 3 hours, or 1 hour to 3 hours, or 1 hour to 2 hours. In certain embodiments, the slurry is maintained at the target temperature for a period of less than 30 min; for example, less than 20 min, or 15 min, or 10 min, or even less than 5 min. In certain embodiments, slurry is maintained at the target temperature for only a couple of minutes or less, i.e. , the slurry is allowed to reach the target temperature and then immediately proceeded to separating step.

[0037] In certain embodiments of the methods of the disclosure, the slurry may be agitated. For example, the slurry may be agitated before bringing it to the target temperature, and/or during the heating to the target temperature, and/or during maintenance at the target temperature. Agitation methods known in the art may be used including, but not limited to, mechanical means (e.g., stirrers), ultrasonication, and microwaves.

[0038] As provided above, after the extraction, the target mixture is separated from the remaining plant material. The target material is then cooled to a temperature in the range of -75 °C to -20 °C to remove lipids (such as waxes, fats, sterols, etc.). In certain embodiments of the methods of the disclosure as described herein, the target mixture is cooled to a temperature in the range of -70 °C to -20 °C, for example in the range of -60 °C to -20 °C, or -70 °C to -40 °C, or -60 °C to -40 °C. In certain embodiments of the methods of the disclosure as described herein, the target mixture is cooled to a temperature of about -60 °C; or about -65 °C; or about -70 °C.

[0039] The target mixture is cooled for a period of time sufficient to separate the lipids. In certain embodiments, the target mixture is cooled for a period of 30 min to 5 hours; or 30 min to 3 hours; or 1 hour to 3 hours; or 1 hour to 2 hours. The separated lipids may be removed by filtration (such as filtration with stainless stell mesh or stainless sintered disk. After removing the lipids, the solvent may be optionally removed to obtain the Cannabis plant oil. In certain embodiments, the solvent may be removed by evaporation. In some embodiments, the solvent vapor is collected and recycled. Thus, the methods of the disclosure, in some embodiments, may be additionally efficient and economical in that less solvent is wasted or lost.

[0040] The disclosure also provides, in another aspect, a Cannabis plant oil prepared according to method of the disclosure as described herein.

[0041] In certain embodiments of the disclosure, the Cannabis plant oil comprises tetrahydrocannabinolic acid, cannabidiolic acid, cannabidiol, tetrahydrocannabivarin, or a combination thereof. In certain embodiments of this aspect, the Cannabis plant oil comprises tetrahydrocannabinolic acid. [0042] In certain embodiments of the disclosure, the Cannabis plant oil prepared according to method of the disclosure as described herein comprises at least 66%, based on the total weight of the oil, of tetrahydrocannabinolic acid. In certain embodiments, the tetrahydrocannabinolic acid is present in an amount of at least 70 wt% based on the total weight of the oil. In certain embodiments, the

tetrahydrocannabinolic acid is present in an amount of at least 74 wt% based on the total weight of the oil.

[0043] In certain embodiments of the disclosure, the Cannabis plant oil prepared according to method of the disclosure as described herein comprises one or more terpenes and/or terpenoids. In certain embodiments, the one or more terpenes and/or terpenoids is present in an amount of at least 2%, based on the total weight of the oil.

[0044] The particulars shown herein are by way of example and for purposes of illustrative discussion of certain embodiments of the present invention only and are presented in the cause of providing what is believed to be the most useful and readily understood description of the principles and conceptual aspects of various embodiments of the disclosure. In this regard, no attempt is made to show structural details of the invention in more detail than is necessary for the fundamental understanding of the invention, the description taken with the examples making apparent to those skilled in the art how the several forms of the disclosure may be embodied in practice. Thus, before the disclosed compositions and methods are described, it is to be understood that the aspects described herein are not limited to specific embodiments, or configurations, and as such can, of course, vary. It is to be understood that the embodiments of the disclosure disclosed herein are illustrative of the principles of the present disclosure. Other modifications that may be employed are within the scope of the disclosure. Thus, by way of example, but not of limitation, alternative configurations of the present disclosure may be utilized in accordance with the teachings herein. In addition, the terminology used herein is for the purpose of describing particular aspects only and, unless specifically defined herein, is not intended to be limiting. Accordingly, the present disclosure is not limited to that precisely as shown and described. [0045] As used herein, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise. "And" as used herein is

interchangeably used with "or" unless expressly stated otherwise.

[0046] As used herein,“about” means ± five percent (5 %) of the recited unit of measure.

[0047] As used herein,“cannabinoids” include any one of substances that are structurally related to tetrahydrocannabinol and that bind to a cannabinoid receptor such as CB1 , CB2, or both.

[0048] Unless the context clearly requires otherwise, throughout the description and the claims, the words‘comprise’,‘comprising’, and the like are to be construed in an inclusive sense as opposed to an exclusive or exhaustive sense; that is to say, in the sense of“including, but not limited to”. Words using the singular or plural number also include the plural and singular number, respectively. Additionally, the words "herein," "above," and "below" and words of similar import, when used in this application, shall refer to this application as a whole and not to any particular portions of the application. The compositions and methods for their use can

"comprise," "consist essentially of," or "consist of" any of the ingredients or steps disclosed throughout the specification.

[0049] Certain aspects of the disclosure are illustrated further by the following examples, which are not to be construed as limiting the disclosure in scope or spirit to the specific procedures and compounds described in them.

EXAMPLES

Example 1 : General procedure

[0050] Raw Cannabis plant material (2kg) is loaded into an extraction column, and cooled to -20 °C. Then, a minimum of -30 psi vacuum is applied to the column. To the extraction column containing the raw plant material, cold solvent(s) (12.5 kg, cooled to about -40 °C) was added to obtain a slurry. The addition of the cold solvent(s) is accomplished over 2 to 5 minutes, assisted using inert gas push.

[0051] The extraction column containing the slurry is then brought up to the target temperature with controlled heating. Specifically, controlled heating is achieved with 2 kW of heating power using a polydiimethylsiloxane heat transfer fluid and maintaining hating rate in a range of 1 °C/min to 2.5 °C/min and the pressure in a range of 2 atm to 7 atm, or up to 35 atm, depending on the solvent system. The slurry in the extraction column is then maintained at the target temperature for at least 5 minutes, up to 60 minutes.

[0052] The slurry is then transferred from the extraction column to the dewaxing column, and cooled to -75 °C to -40 °C for 60 minutes. After precipitation of lipids, the remaining mixture is transferred to a recovery tank leaving behind the lipid precipitate. After removing the solvent from the mixture using a low-temperature, condensation coil assisted gas compressor, Cannabis oil is obtained. Residual solvent is removed using a vacuum assisted centrifuge.

Example 2: Cookies & Chem Cannabis flower

[0053] Cannabis flower from Cookies & Chem strain was harvested, homogenized, and split into 2000 g samples (wet weight). The 2000 g samples were then dried and reweighed, and the dry weight is provided in Table 1.

[0054] The raw dry Cannabis material samples were then processed according to general procedure provided in Example 1 using propane: butane in a 50:50 ratio cooled to -40 °C. Three samples were heated to three different target temperatures: 10° C, 30° C, and 50° C. To achieve the desired target temperature, the heating was controlled by maintaining the heating rate at 2.5 °C/min (for 10 °C), 2 °C/min (for 30 °C), or 1 °C/min (for 50 °C), and the pressure at 4 atm, 6.8 atm, or 12 atm, respectively. Once the target temperature was reached, the samples were maintained at the target temperature for 5 minutes.

[0055] Traditional extraction using propane:butane (50:50) solvent system is performed at a target temperature of -40° C. Thus, a control sample was maintained a target temperature of -40° C for 5 minutes. After extraction, each sample was then dewaxed as described above (-75 °C for 60 minutes), and the obtained Cannabis plant oil was analyzed for THCA and terpenes content using HPLC with diode detection. The results are provided in Table 1. Table 1

¹ The weight of 2000 g of raw cannabis material after drying.

² The final weight of cannabis oil obtained in the method.

[0056] The results in Table 1 show that the yield for Cannabis plant oil increases with the increase in target temperature. Specifically, when the extraction was performed at target temperature of 50 °C, the overall yield improved by 33% over the extraction performed at the control (-40° C) target temperature (e.g., 104.13 g vs. 78 g). The improved yield is very important for commercial efforts where any increase in yield of Cannabis plant oil from the wet plant material translates to significant cost savings and less waste.

[0057] But increase in overall oil yield does not necessarily correlate to an increase in quality of oil, which is determined by its content of desired components, such as THCA and terpenes. Thus, it was important to evaluate the content of the desired components in the plant oil obtained by the methods of the disclosure. As provided in Table 1 , the THCA and terpenes content of the oil extracted using the methods of the disclosure was better or comparable to the THCA and terpenes content of the oil extracted at control target temperature. Thus, the methods of the disclosure provide cannabis plant oil in high yield and improved content of desired components (such as THCA and terpenes).

Example 3: Viper Cookies Cannabis flower

[0058] Cannabis flower from Viper Cookies strain was harvested, homogenized, and split into 2000 g samples (wet weight). This raw plant material was then processed according to general procedure provided in Example 1 using

propane: butane (50:50) cooled to -40° C. The slurry was brought to a target temperature of 30° C (2 °C/min heat rate, and pressure of 4 atm), and maintained at that temperature for 5 minutes. A control sample was extracted at a target temperature of -40° C for 5 minutes. After extraction, each sample was dewaxed for 60 minutes at -65° C, and the obtained Cannabis plant oil was analyzed for THCA, terpenes, and total cannabinoids content. The results are provided in Table 2.

Table 2

¹ The final weight of cannabis oil obtained in the method.

² The yield of cannabis oil based on the wet weight of raw plant material.

[0059] The results in Table 2 show that the yield for Cannabis plant oil extracted at 30 °C was about 12.5% higher than the yield for Cannabis plant oil extracted at -40 °C (e.g., 103.2 g vs. 91.7 g). In addition, the THCA, terpenes, and total

cannabinoids content in the oil extracted at 30 °C was better or comparable to the THCA, terpenes, and total cannabinoids content in the oil extracted at -40 °C.

Example 4: Tangie Cannabis flower

[0060] Cannabis flower from Tangie strain was harvested, homogenized, and split into 2000 g samples (wet weight). This raw plant material was then processed according to general procedure provided in Example 1 using 9:1 propane: n-butane solvent mixture (25.5 kg) cooled to -40° C. Solvent was injected into the reaction chamber at -40° C. After the injection, the slurry was then brought to a target temperature of 55° C (1 °C/min heat rate, and pressure of 7 atm), and maintained at that temperature for 5 minutes. A control sample was extracted at a target temperature of -40° C for 5 minutes. After extraction, each sample was dewaxed for 60 minutes at -65° C, and the obtained Cannabis plant oil was analyzed for THCA, terpenes, and total cannabinoids content. The results are provided in Table 3. The Cannabis plant oil extract obtained at -40 °C was placed into a sealed pressure vessel and placed in a degassing oven for 20 days to allow for cannabinoid crystal development. The cannabinoid crystals were a mixture or cannabinoids, with THCA as the primary component and minor amounts of THCV. The Cannabis plant oil extract obtained at 55 °C was also placed into a sealed pressure vessel in a degassing oven; however the cannabinoid crystal development was accomplished in 24 hours. These quickly-forming crystals were comparable in flavor and aroma to, and slightly smaller in size from, the crystals that formed over 20 days.

Table 3

¹ The final weight of cannabis oil obtained in the method.

² The yield of cannabis oil based on the wet weight of raw plant material.

[0061] The results in Table 3 show that the yield for Cannabis plant oil extracted at 55 °C was about 223% higher than the yield for Cannabis plant oil extracted at -40 °C (e.g., 358.96 g vs. 111.28 g). The THCA and total cannabinoid content in the Cannabis plant oil extracted at 55 °C is lower than the content in the control oil.

Without being bound by a particular theory, however, it is believed that the other components present in the control oil negatively affect nucleation and crystal formation of THCA. As a result, the control oil required 20 days for nucleation and crystal formation, whereas the Cannabis plant oil extracted using the method of the disclosure required 24 hours for crystal formation. Thus, even with lower THCA concentration, the Cannabis plant oil extracted using the method of the disclosure provides significantly higher commercial value (i.e., requires far less resources and time) than the plant oil extracted with the traditional methods.

[0062] Various aspects of the present disclosure are further exemplified by the non limiting embodiments recited in the claims below. In each case, features of multiple claims can be combined in any fashion not inconsistent with the specification and not logically inconsistent.

[0063] It is understood that the examples and embodiments described herein are for illustrative purposes only and that various modifications or changes in light thereof will be suggested to persons skilled in the art and are to be incorporated within the spirit and purview of this application and scope of the appended claims. All publications, patents, and patent applications cited herein are hereby incorporated herein by reference for all purposes.

Claims

We claim:

1. A method of obtaining a Cannabis plant oil from a Cannabis plant material, the method comprising:

separating the target mixture from the remaining plant material; and

2. The method of claim 1 , wherein the Cannabis plant material is Cannabis flowers.

3. The method of claim 1 or 2, wherein the one or more solvents provided to the Cannabis plant material is a temperature between -70 °C to -30 °C; or -60 °C to -30 °C; or -50 °C to -30 °C; or -40 °C to -30 °C; or -70 °C to -40 °C; or -60 °C to -40 °C; or -50 °C to -40 °C; or -70 °C to -50 °C; or -60 °C to -50 °C; or -45 °C to -35 °C; or -42 °C to -38 °C; or about -40 °C.

4. The method of any of claims 1-3, wherein the one or more solvents is selected from propane, n-butane, and /-butane.

5. The method of any of claims 1-4, wherein the one or more solvents is propane; or wherein the one or more solvents is butane.

6. The method of any of claims 1-4, wherein the one or more solvents is a combination of propane and butane.

7. The method of any of claims 1 -4, wherein the one or more solvents is a combination of propane and n-butane.

8. The method of claim 7, wherein propane and n-butane are provided in a weight ratio in a range of 95:5 and 50:50; or 95:5 and 60:40; or 95:5 and 70:30; or 95:5 and 80:20; or 95:5 and 85:15.

9. The method of claim 7, wherein propane and n-butane are provided in a weight ratio in a range of about 90: 10.

10. The method of any of claims 1 -9, wherein the Cannabis plant material and the one or more solvents are provided in a weight ratio in a range of 1 : 1 and 1 :20 (e.g., in a range of 1 :2 and 1 :20, or 1 :4 and 1 :20, or 1 :5 and 1 :20, or 1 : 10 and 1 :20, or 1 : 15 and 1 :20); or a weight ratio or in a range of 1 : 1 and 1 : 15 (e.g., in a range of 1 :2 and 1 :15, or 1 :4 and 1 : 15, or 1 :5 and 1 :15, or 1 : 10 and 1 : 15); or a weight ratio in a range of 1 : 1 and 1 : 10 (e.g., in a range of 1 :2 and 1 : 10, or 1 :4 and 1 : 10, or 1 :5 and 1 : 10); or a weight ratio in a range of 1 : 1 and 1 :5 (e.g., in a range of 1 :2 and 1 :5 or in a range of 1 :4 and 1 :5); or a weight ratio in a range of 1 :4 and 1 :7; or a weight ratio in a range of 1 :8 and 1 :12 (e.g., in a range of 1 :9 and 1 :1 1 ); or a weight ratio of about 1 :10.

1 1. The method of any of claims 1 -10, wherein bringing the slurry to the target temperature and/or maintaining the slurry at the target temperature is performed at pressures of more than 1 atm (e.g., more than 1.5 atm, or 2 atm, or 10 atm, or even 20 atm); or at a pressure in the range of 2 atm to 35 atm (e.g., in the range of 2 atm to 30 atm, or 2 atm to 20 atm, or 2 atm to 15 atm, or 2 atm to 10 atm, or 2 atm to 5 atm); or at a pressure in the range of 3 atm to 35 atm (e.g., in the range of 3 atm to 30 atm, or 3 atm to 20 atm, or 3 atm to 15 atm, or 3 atm to 10 atm, or 3 atm to 5 atm); or at a pressure in the range of 5 atm to 35 atm (e.g., in the range of 5 atm to 30 atm, or 5 atm to 20 atm, or 5 atm to 10 atm); or at a pressure of about 2 atm; or about 3 atm; or about 5 atm; or a pressure in the range of 15 atm to 35 atm (e.g., in the range of 20 atm to 35 atm, or 25 atm to 35 atm; or 30 atm to 35 atm). In certain embodiments, the pressure is in the range of 15 atm to 30 atm (e.g., in the range of 20 atm to 30 atm, or 25 atm to 30 atm).

12. The method of any of claims 1 -1 1 , wherein the target temperature is in the range of 20 °C to 70 °C; or 20 °C to 60 °C; or 20 °C to 50 °C; or 30 °C to 70 °C; or 30 °C to 60 °C; or 30 °C to 50 °C, or 10 °C to 50 °C; or 10 °C to 30 °C; or 40 °C to 70 °C; or 40 °C to 60 °C; or 40 °C to 50 °C.

13. The method of any of claims 1 -1 1 , wherein the target temperature is in the range of 30 °C to 50 °C.

14. The method of any of claims 1-11 , wherein the slurry is brought to the target temperature in the range of 30 °C to 50 °C and a pressure of more than 1 atm (e.g.,

1.5 atm, or 2 atm, or 10 atm, or 20 atm, or 30 atm, or even 35 atm).

15. The method of any of claims 1 -11 , wherein the target temperature is in the range of -10 °C to 0 °C; or -10 °C to -4 °C; or -10 °C to -5 °C; or -10 °C to -8 °C; or -10 °C; or about -4 °C; or about 0 °C.

16. The method of any of claims 1-11 , wherein the slurry is brought to the target temperature in the range of -10 °C to 0 °C and a pressure of more than 1 atm (e.g.,

1.5 atm or 2 atm).

17. The method of any of claims 1 -16, wherein the slurry is maintained at the target temperature for a period of 30 min to 5 hours (e.g., 30 min to 3 hours; or 1 hour to 3 hours; or 1 hour to 2 hours); or for a period of less than 30 min (e.g., less than 20 min, or 15 min, or 10 min, or even less than 5 min).

18. The method of any of claims 1-16, wherein the target mixture is cooled to a temperature in the range of -70 °C to -20 °C; or -60 °C to -20 °C; or -70 °C to -40 °C; or -60 °C to -40 °C; or about -65 °C.

19. The method of any of claims 1-18, wherein the target mixture is cooled for a period of 30 min to 5 hours; or 30 min to 3 hours; or 1 hour to 3 hours; or 1 hour to 2 hours.

20. The method of any of claims 1-19, wherein the Cannabis plant oil comprises one or more tetrahydrocannabinolic acid, cannabidiolic acid, cannabidiol,

tetrahydrocannabivarin, or a combination thereof.

21. The method of any of claims 1 -19, wherein the Cannabis plant oil comprises tetrahydrocannabinolic acid.

22. The method of claim 21 , wherein the tetrahydrocannabinolic acid is present in an amount of at least 66 wt%, based on the total weight of the oil.

23. The method of claim 21 , wherein the tetrahydrocannabinolic acid is present in an amount of at least 70 wt% or at least 74 wt%, based on the total weight of the oil.

24. The method of any of claims 21 -23, wherein the Cannabis plant oil further comprises one or more terpenes and/or terpenoids.

25. The method of claim 24, wherein the one or more terpenes and/or terpenoids is present in an amount of at least 2 wt%, based on the total weight of the oil.

26. A Cannabis plant oil prepared according to the method of any of claims 1-21.

27. The Cannabis plant oil of claim 26 comprising one or more

tetrahydrocannabinolic acid, cannabidiolic acid, cannabidiol, tetrahydrocannabivarin, or a combination thereof.

28. The Cannabis plant oil of claim 26 comprising tetrahydrocannabinolic acid.

29. The Cannabis plant oil of claims 26-28, wherein the tetrahydrocannabinolic acid is present in an amount of at least 66 wt%, based on the total weight of the oil.

30. The Cannabis plant oil of claims 26-28, wherein the tetrahydrocannabinolic acid is present in an amount of at least 70 wt% or at least 74 wt%, based on the total weight of the oil.

31. The Cannabis plant oil of claims 26-30, wherein the Cannabis plant oil further comprises one or more terpenes and/or terpenoids.

32. The Cannabis plant oil of claim 31 , wherein the one or more terpenes and/or terpenoids is present in an amount of at least 2 wt%, based on the total weight of the oil.