NZ796408A - Terpene enrichment methods and systems - Google Patents

Abstract

The present disclosure provides methods and systems producing active extraction products from cannabis resin. An example method comprises introducing a mixture of a resin and an extractor into a sealed container, heating the mixture to extract cannabinoids and terpenes from the resin, adding water to the mixture, cooking the mixture and water, for example at high temperature and pressure for a predetermined time period to decarboxylate the cannabinoids, allowing the mixture and water to cool and separate, and removing an active extraction product from an upper portion of the sealed container.

Description

The present disclosure provides methods and systems producing active extraction products from cannabis resin. An example method comprises ucing a e of a resin and an extractor into a sealed container, heating the mixture to extract cannabinoids and terpenes from the resin, adding water to the mixture, cooking the mixture and water, for example at high ature and pressure for a predetermined time period to decarboxylate the cannabinoids, allowing the mixture and water to cool and separate, and removing an active extraction product from an upper portion of the sealed container.

NZ 796408 October 2019 2019 TERPENE ENRICHMENT METHODS AND SYSTEMS Cross Reference to Related Application This application claims the benefit of priority of US. Provisional Patent Application No. 62/578,971 filed r 30, 2017, which is hereby incorporated herein by reference in its entirety.

Technical Field The present disclosure relates to extraction and decarboxylation of nds from cannabis.

Background Cannabis contains many compounds of medicinal and commercial significance, including cannabinoids and terpenes. A large fraction (often >50%) of the terpenes are lost upon drying of the plant. Most tions rely on dried material to make final products which s in a significant loss of terpenes before extractions.

Furthermore, current solvent extraction processes, such as ethanol extraction, lose much of the terpenes during extraction. Finally, is products which intend to use the therapeutic effects of cannabinoids must undergo a decarboxylation process, and optional winterization and work up steps, and this can cause further terpene losses.

The inventors have determined a need for ed methods and systems for extraction of compounds from cannabis.

Summary One aspect of the present disclosure provides a method of producing active extraction products from cannabis resin. The method comprises introducing a e of a resin and an tor into a sealed container, heating the mixture to extract cannabinoids and terpenes from the resin; adding water to the mixture, cooking the mixture and water at temperature in a range of imately 90-140 Celsius under a for a period pressure in a range of approximately 0-420 kPa over atmospheric pressure AMENDED SHEET ; .,«,s,_.,., 5. . . ,7 e ., .7 . _ A“..pruaweggkézngumyg. ..vamszzegnlmg-vaggmp‘MW.,._-W...... 2018/051374 October 2019 252019 water of about 1-25 hours to decarboxylate the cannabinoids, allowing the mixture and extraction to cool and separate for a period of about 8—24 hours, and removing an active product from an upper portion of the sealed container.

The extraction product may comprise a terpene to cannabinoid ratio by mass in the range of about 1:1 to 1:20. Terpenes may comprise at least 5% of active compounds in the active extraction t. When made from fresh cannabis resin, the active extraction product can be enriched in terpenes by up to 150% as compared to the e content of dried is of the same cultivar.

In some embodiments the method comprises filtering resin from the mixture after extracting cannabinoids and terpenes. In some embodiments filtering resin occurs prior to cooking the mixture.

In some embodiments the extractor comprises an edible lipid. In some embodiments the extractor comprises a hydrophobic organic solvent. In some embodiments the method comprises evaporating solvent and removing residues from the extraction product.

In some embodiments the method comprises removing a al mixture from a bottom n of the sealed container and separating water and extractor from the residual mixture to produce a secondary extraction product. In some embodiments the method comprises introducing the secondary extraction product into the sealed container with the mixture.

Further aspects of the invention and details of example embodiments are set forth below.

Drawings The following figures set forth embodiments in which like reference numerals denote like parts. Embodiments are illustrated by way of example and not by way of limitation in the accompanying s.

Figure 1 shows an e container for carrying cut a method of producing a terpene-rich extraction t according to one embodiment of the t disclosure.

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October 2019 252019 Figure 2 shows another e container for carrying out a method of producing a terpene—rich extraction product according to one embodiment of the present disclosure.

Figure 2A is a sectional view taken along line A-A in Figure 2.

Figure 28 is a side view of the container of Figure 2.

Figure 2C is a top view of the container of Figure 2.

Figure 3A shows terpene content of dry is and extraction products made by example methods according to the present disclosure for different strains.

Figure 3B shows the tage of terpene increase from dry cannabis to extraction ts made by example s according to the present disclosure for different strains.

Figure 3C shows the distribution of terpene contents for dry cannabis strains and extraction products made by example methods according to the present disclosure.

Detailed Description - The following disclosure provides methods and associated apparatus and systems for ng terpene rich cannabis extracts from is resin in a single vessel reaction. In some embodiments, the starting material used is cannabis resin separated from fresh or frozen plant al. In some embodiments, the cannabinoids are decarboxylated while still in a mixture with the terpenes, resin and an extractor.

Certain embodiments provide s and systems for producing decarboxylated extraction products (sometimes referred to as “orally active" extraction ts, or simply “active” extraction products). As described in detail below, starting from fresh or frozen cannabis (plant matter or physically separated cannabis resin) an extract can be made which s a higher proportion of terpenes to cannabinoids than are found in dried is material or the extracts made thereof. Even starting from material that is dried, the extraction and decarboxylation process will retain more terpenes than typical cannabis extraction processes. Fresh is is infused directly into a solvent or edible food matrix and decarboxylated, and final oil separated in a AMENDED SHEET AT»— ;s,,9.m.‘,x “7,", . “4.“, 7‘. m. ,. ., .......-..\~ by: ..-».-,=~.t.,/.m. .._ W-.w..=wnumw.mm ..A)¢m.®.»...{..._r.sg-;my, October 2019 252019 single pressurized extraction vessel. Oil is filtered and ted from any water remaining.

For simplicity and clarity of illustration, reference numerals may be repeated among the figures to indicate corresponding or ous elements.

Numerous details are set forth to provide an understanding of the examples described herein. The examples may be practiced without these details. In other instances, well- known methods, procedures, and components are not described in detail to avoid obscuring the examples described. The description is not to be considered as limited to the scope of the examples described herein.

In an example method according to the present disclosure, fresh is resin, also known as bubble hash, is used as a starting material for an extraction process. As described below, the resin is mixed with an extractor comprising either a hobic organic solvent or an edible lipid such as coconut oil. In example embodiments, the mixture of resin and extractor is'heated, and then separated under particular conditions to produce a final active product which has a relatively high level of terpenes compared to products produced by other methods using the same starting material. In other words, certain embodiments provide extraction methods that result in less terpene loss than other s typically employed in the art.

The extracts with the highest concentration of terpenes from a particular batch of cannabis will be produced from cannabis resin made from fresh cannabis material which is utilized for extraction directly after harvest (or which is frozen directly after harvest and utilized for extraction later). The cannabis resin may, for example, be obtained by sing plant material as described in International Patent ation No. , which is hereby incorporated by reference herein.

After being made into bubble hash, or cannabis resin, the resin may be ved into solvent or oil immediately for sing by s according to the present disclosure or may be frozen for future use. In some embodiments, the ratio (by mass) of resin to tor is in the range of about 121.5 to 1:3 if the tor is an edible oil, or about 1:2 to 1:10 if the extractor is a hobic organic solvent.

The resin and extractor are placed into a sealed container. Figure 1 shows an e container 100 for carrying out an extraction process according to the AMENDED SHEET «a new, ».— A ... .- 9... t- . .. . s ...V swafin... .,»L_Q.,..M,. 7‘“«7erkmeeé‘a-vfomqwr-gganE‘gAAisuvreL—‘Amprv .ans»: 2018/051374 October 2019 2019 present disclosure. The container 100 comprises a sealed housing 110, having an agitator 120 and a pressure and temperature controller 130. The housing 110 has an input port 112 for receiving the resin/extractor mixture, a water inlet port 114 for receiving water, a product port 116 for removal of terpene enriched extracts, and an outlet port 118 for removal of water and remaining resin/extractor. A resin output hatch 119 may be provided at the bottom of the container 119 for removing settled resins- from the g 110, for example at the end of a batch process.

In the illustrated example, the agitator 120 comprises a motor 122, shaft 124 and impeller 126. The or 120 may take different forms in other embodiments.

The resin and extractor are mixed in the ner 100 by the agitator 120 to create a resin/extractor mixture, which is heated to extract cannabis material binoids and es). In some ments, the extractor mixture is heated for about 20-60 minutes before filtering any resin or adding any water, as described below. In some embodiments, some or all of the depleted resin can optionally be filtered out of the mixture at this point in the process. For example, in situations where there is a lot of resin present, some of the resin may be filtered out before decarboxylation and may be further dissolved in the same tor after decarboxylation. In some embodiments, depleted resin can optionally be filtered out after decarboxylation.

To decarboxylate, water is added to the mixture at a 1:1 ratio (by mass) with the oil or solvent. The mixture of cannabis resin/extractor/water (or extractor/water if resin is already filtered out) is cooked at a temperature in a range of approximately 90- 140 Celsius under pressure in a range of approximately 0—420 kPa above atmospheric pressure for a time period of about 1-24 hours to decarboxylate the cannabinoids. In some embodiments, the mixture of cannabis resin/extractor/water is cooked at a temperature of approximately 125 Celsius under pressure in a range of approximately 0-150 kPa (or approximately 80 kPa in some examples) above atmospheric pressure for a time period of about 2-3 hours. After cooking, the mixture is typically left to cool for about 8-24 hours after the cooking period.

After the mixture has separated, the oil or solvent at the top of the container will form a high-quality extraction t, and is removed from the container AMENDED SHEET October 2019 252019 100, for example by ing or siphoning h the product port 116. Water may be added to the bottom of the container 100 through the water inlet port 114 to raise a level of an interface between the top layer ting of the high-quality extraction product and a lower layer with the water/resin to near the level of the product port 116.

Any suitable process may be used for removing the extraction product from the upper portion of the container, so long as it does not include any, or at least no significant amount, of the resin or water at the bottom of the container. For example, in some embodiments the layer of high quality extraction product may be removed from the container 100 by a pipette or by using a beaker to decant the extraction product. The extraction product may also be passed through a filter in some embodiments.

If an edible oil was used, the extraction product removed from the product port 116 is the final product and will be the most terpene rich extract. If a solvent was used then the solvent is evaporated, and es removed to create the final product, but this s in some terpene loss. These extraction products (whether ed using either edible oil or solvent as the extractor) are considered the highest quality and should not have any residual water and are referred to herein as “primary extraction The remaining residual mixture of extractor, resin and water leftover after decanting is removed from the container 100, for example through the outlet port 118, then passed through a filter and the resin removed from the water and extractor. Water and extractor are separated in a funnel. The ing oil or extract is considered second quality and contains residual water and is referred to herein as a “secondary extraction product”.

The secondary tion product can be dried with a drying agent, or heated with more water again and first quality siphoned off to turn it into a higher y product of similar quality to the primary extraction products. The ary extraction product can also be added'to the start of a new production cycle as part of the extractor input Resin that has been separated by filtration (either before or after decarboxylation) will often still contain up to 5% cannabinoids when dried (usually 1-3%) and can be used as a flour substitute for making cannabis edibles.

AMENDED SHEET 2.... 3. 1,4, , . . ,. .7 .._ - a~~..~»~ :ws 5nr1-.-5n.».=qx»g‘swwmwwmgwmwwgwy.h_ «r w , , » ~ th7\ ( ”up, , .. .2-.. ., ,u «flaw-w- ane-«em m: October 2019 252019 s 2, 2A, 28 and 2C show another example container 200 for ng out an extraction process according to the present disclosure. The container 200 comprises a sealed housing 210, having a lid 212 with a pressure relief valve 213 thereon. The lid 212 can be opened to receive resin and extractor, and is held closed by closures 211. An or can be inserted into the interior of the housing 210 to mix the resin and tor while the lid 212 is open. The g has an input port 214 in a lower side portion thereof, a product output 216 in an upper side n f, and an outlet port 218 and the bottom thereof. In some embodiments the outlet port 218 includes a built-in valVe. In some embodiments the outlet port 218 es a built-in filter.

The. housing 210 also has a viewing window 219 along the side thereof.

The viewing window 219 is positioned to e a user with a view of the contents of the interior of the housing 210 from a height of the product output 216 to a predetermined height below the product output 216, such that the user can see the height of a top layer of high—quality extraction product on top of the separated mixture.

In some embodiments, the container 200 also has heating elements 220 built into the walls f. The walls of the container may be insulated in some embodiments. in an example operation, resin and extractor are added through the open lid 212, and optionally mixed manually or by means of an agitator apparatus. In some embodiments, the resin and extractor may be heated while mixing to create a mostly homogeneous solution. The lid 212 is closed, water is added and the mixture is cooked to decarboxylate the cannabinoids. The mixture may be cooked, for example under high temperature and high pressure as described above. After the cook, pressure is ed via a tee connected near 213, and then additional water is introduced through port 214 to raise the liquid level until the bottom of the top layer of high-quality extraction product gets near the product port 216 so that the oil exits through the product port 216. Once, the high-quality product has been removed, the remaining material is removed by opening the outlet port 218. The material may be removed by a combination of gravity and compressed air introduced through port 216.

AMENDED SHEET >>777'>v‘q‘— q {‘4 ~7—.~ N;M +5“? "5, ,. ;>-,.<»«_<.s..,—W,795*:ngM7AWL—W;my»; y ”5.. «Mp—t,,- October 2019 2019 After the material has been removed, the lid 212 is opened up for access for cleaning the interior of the container 200.

In some embodiments, the high quality extraction t has a terpene to inoid ratio (by mass) in the range of 1:20 to 1:5, although this ratio may vary depending on the strain(s) of cannabis used for the starting material. For example, Figures 3A to 3C illustrate results of a comparison between a high-quality extraction product made using resin from fresh/frozen product of a variety of cultivars or strains using coconut oil as the extractor, and dried plant material of the same cultivar/strain‘.

Figure 3A shows terpene content of dry cannabis and extraction ts made by example methods according to the present disclosure, and Figure 3B shows the percentage of e increase from dry cannabis to tion products made by example methods according to the present disclosure, for a variety of ent strains of cannabis. Dry cannabis from different strains can have different terpene to cannabinoid ratios, and the terpene to cannabinoid ratio for extraction products made by example methods according to the present disclosure do not necessarily correspond to the terpene to cannabinoid ratio for dry cannabis. For example, the “Dancehall” strain has one of the lowest terpene to cannabinoid ratios of those tested for dry cannabis and of the highest terpene to cannabinoid ratios for the extraction product (and therefore has the highest percentage enrichment), whereas the “CBD Shark" strain has a slightly higher (in comparison to Dancehall) terpene to inoid ratio for dry cannabis but a significantly lower terpene to cannabinoid ratio for the extraction product (and has the lowest tage enrichment). However, as illustrated in Figure 3C, which shows the distribution of terpene contents for dry cannabis s and extraction products made by example methods according to the t disclosure, the extraction products from all strains tested in the illustrated example have higher terpene to cannabinoid ratios than any of the dry cannabis.

In some ments, the high quality extraction product may have a terpene to cannabinoid ratio (by mass) of about 1:1 when ng with a strain with high terpene content and low cannabinoid content. Dry cannabis typically has a terpene to cannabinoid ratio of about 1:15, and extracts produced by prior art t based techniques often have terpene to cannabinoid ratios of about 1:75 or lower. The AMENDED SHEET October 2019 2019 extraction products created by methods according to the present sure are thus significantly terpene enriched compared to certain prior art products.

It will be appreciated that numerous specific details are set forth in order to provide a thorough understanding of the exemplary embodiments described herein. r, it will be understood by those of ordinary skill in the art that the embodiments described herein may be practiced t these specific details. In other instances, well—known methods, procedures and components have not been bed in detail so as not to obscure the embodiments bed herein. Furthermore, this description not to be considered as limiting the scope of the embodiments described herein in any of the various example way, but rather as merely describing implementation embodiments described herein.

The description provides many example embodiments of the inventive subject . Although each embodiment represents a single combination of inventive elements, the inventive subject matter is considered to include all possible combinations of the disclosed elements. Thus if one ment comprises elements A, B, and C, and a second embodiment comprises elements B and D, then the inventive t matter is also considered to include other remaining combinations of A, B, C, or D, even if not explicitly disclosed.

As will be apparent to those skilled in the art in light of the foregoing disclosure, many alterations and modifications are possible to the methods and systems described . While a number of exemplary aspects and embodiments have been discussed above, those of skill in the art will recognize certain modifications, permutations, ons and sub-combinations thereof. It is therefore intended that the following appended claims and claims ter introduced are interpreted to include all such modifications, permutations, additions and sub-combinations as may reasonably be inferred by one skilled in the art. The scope of the claims should not be limited by the ments set forth in the examples, but should be given the broadest interpretation consistent with the foregoing disclosure.

The present disclosure may be embodied in other specific forms without departing from its spirit or essential characteristics. The bed embodiments are to be considered in all respects only as illustrative and not restrictive.

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October 2019 252019

Claims (18)

Claims

1. A method of producing active extraction products from cannabis resin, the method comprising: introducing a mixture of a resin and an extractor into a sealed container; heating the mixture in the sealedcontainer to extract cannabinoids and terpenes from‘the resin to e an extracted mixture; adding water to the extracted mixture in the sealed container; decarboxylating the inoids by cooking the extracted mixture and water in the sealed container at a temperature in a range of approximately 90 to 140 Celsius under a pressure of up to approximately 420 kPa over atmospheric pressure for a period of about 1-25 hours; allowing the mixture and water to cool and separate in the sealed container for a period of about 8-24 hours; and removing an active extraction t from an upper portion of the sealed

2. The method of claim 1 wherein oxylating the cannabinoids by cooking the extracted mixture and water comprises cooking at a temperature of approximately 125 Celsius and a re of up to 150 kPa over atmospheric pressure.

3. The method of claim 2 comprising cooking at a pressure of imately 80 kPa over atmospheric pressure for a period of 2—3 hours.

4. The method of claim 1 wherein the extraction product comprises a terpene to inoid ratio by mass in the range 0f about 1:20 to 1:1.

5. The method of any one of claims 1 to 4 wherein terpenes comprise at least 5% of active compounds in the active extraction product. AMENDED SHEET 25 October 2019 252019

6. The method of any one of claims 1 to 5 comprising filtering resin from the mixture after extracting cannabinoids and terpenes.

7. The method of claim 6 wherein filtering resin occurs prior to cooking the mixture.

8. The method of any one of claims 1 to 7 wherein the extractor comprises an edible lipid.

9. The method of any one of claims 1 to 7 wherein the extractor comprises a hydrophobic c solvent.

10. The method of claim 9 comprising evaporating solvent and removing es from the extraction product.

11. The method of any one of claims 1 to 10 wherein adding water to the ted mixture comprises adding water in a 1:1 ratio (by mass) with the extractor.

12. The method of any one of claims 1 to 11 comprising removing a al mixture from a bottom portion of the sealed container and separating water and extractor from the residual mixture to produce a secondary extraction product.

13. The method of claim 12 comprising introducing the secondary extraction product into the sealed container with the mixture.

14. The method of any one of claims 1 to 13 comprising obtaining the resin for the mixture by separating the resin from fresh plant material.

15. The method of claim 14 wherein the resin is mixed with the extractor immediately after separating the resin from fresh plant material. AMENDED SHEET 25 October 2019 2019

16. The method of any one of claims 1 to 15 wherein the sealed container has an inlet port in a lower portion thereof and a product port in the upper portion thereof, and wherein removing the active extraction product from the upper n of the sealed container Comprises introducing additional water into the inlet port until a height of a bottom of a top layer of the active extraction t is near a height of the product port.

17. An apparatus for producing active extraction products from is resin, the apparatus comprising: a sealed housing having a le opening in a top thereof for receiving resin and extractor; an inlet port in a lower side portion of the sealed housing for receiving water; a product port in an upper side portion of the sealed housing for removing high- quality active extraction product; an outlet port in a bottom of the sealed housing; and a viewing window positioned to provide a user with a view of materials in an interior of the sealed housing from a height of the product port to a predetermined height below the t port.

18. A method of producing active extraction products from cannabis resin, the method comprising: introducing fresh cannabis resin, an edible lipid and water into a sealed extracting cannabinoids and terpenes from the fresh cannabis resin in the sealed container; decarboxylating the cannabinoids by cooking the fresh cannabis resin, edible lipid and water in the sealed container at a temperature in a range of approximately 90 to 140 Celsius under a pressure of up to approximately 420 kPa over atmospheric pressure for a period of about 1-25 hours; alloWing the mixture and water to cool and separate in the sealed container for a period of about 8-24 hours; and AMENDED SHEET “A“-.p. _7J.,A,.,t. ,.. K;.:..._,:r.n «Mm. :.u.— a” .di —\~.-~ r.i«.....Y,.m,—.4m f