CBD Oil Distillation Process

CBDISTILLERY

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Hemp (Cannabis sativa L.) synthesizes and accumulates a number of secondary metabolites such as terpenes and cannabinoids. They are mostly deposited as resin into the glandular trichomes occurring on the leaves and, to a major extent, on the flower bracts. In the last few years, hemp for production of high-value chemicals became a major commodity in the U.S. and across the world. The hypothesis was that hemp biomass valorization can be achieved through distillation and procurement of two high-value products: the essential oil (EO) and cannabinoids. Furthermore, the secondary hypothesis was that the distillation process will decarboxylate cannabinoids hence improving cannabinoid composition of extracted hemp biomass. Therefore, this study elucidated the effect of steam distillation on changes in the content and compositional profile of cannabinoids in the extracted biomass. Certified organic CBD-hemp strains (chemovars, varieties) Red Bordeaux, Cherry Wine and Umpqua (flowers and some upper leaves) and a T&H strain that included chopped whole-plant biomass, were subjected to steam distillation, and the EO and cannabinoids profile were analyzed by gas chromatography-mass spectrometry (GC–MS) and HPLC, respectively. The distillation of hemp resulted in apparent decarboxylation and conversion of cannabinoids in the distilled biomass. The study demonstrated a simple method for valorization of CBD-hemp through the production of two high-value chemicals, i.e. EO and cannabinoids with improved profile through the conversion of cannabidiolic acid (CBD-A) into cannabidiol (CBD), cannabichromenic acid (CBC-A) into cannabichromene (CBC), cannabidivarinic acid (CBDV-A) into cannabidivarin (CBDV), cannabigerolic acid (CBG-A) into cannabigerol (CBG), and δ-9-tetrahydrocannabinolic acid (THC-A) into δ-9-tetrahydrocannabinol (THC). In addition, the distilled biomass contained CBN while the non-distilled did not. Distillation improved the cannabinoids profile; e.g. the distilled hemp biomass had 3.4 times higher CBD in variety Red Bordeaux, 5.6 times in Cherry Wine, 9 times in variety Umpqua, and 6 times in T&H compared to the original non-distilled samples, respectively. Most of the cannabinoids remained in the distilled biomass and small amounts of CBD were transferred to the EO. The CBD concentration in the EO was as follows: 5.3% in the EO of Umpqua, 0.15% in the EO of Cherry Wine and Red Bordeaux and 0.06% in the EO of T&H. The main 3 EO constituents were similar but in different ratio; myrcene (23.2%), (E)-caryophyllene (16.7%) and selina-3,7(11)-diene (9.6%) in Cherry Wine; (E)-caryophyllene (~ 20%), myrcene (16.6%), selina-3,7(11)-diene (9.6%), α-humulene (8.0%) in Red Bordeaux; (E)-caryophyllene (18.2%) guaiol (7.0%), 10-epi-γ-eudesmol (6.9%) in Umpqua; and (E)-caryophyllene (30.5%), α-humulene (9.1%), and (E)-α-bisabolene (6.5%) in T&H. In addition, distillation reduced total THC in the distilled biomass. Scanning electron microscopy (SEM) analyses revealed that most of the glandular trichomes in the distilled biomass were not disturbed (remained intact); that suggest a possibility for terpenes evaporation through the epidermal membrane covering the glandular trichomes leaving the cannabinoids in the trichomes. This explained the fact that distillation resulted in terpene extraction while the cannabinoids remained in the distilled material. How is CBD extracted from the hemp plant, and can you make your own CBD-infused oil at home? Read our CBD extraction guide to find out. In this blog, Maratek gives an overview of the cannabis and hemp oil distillation process and how it can help to create a consistent pure product.

Valorization of CBD-hemp through distillation to provide essential oil and improved cannabinoids profile

Hemp (Cannabis sativa L.) synthesizes and accumulates a number of secondary metabolites such as terpenes and cannabinoids. They are mostly deposited as resin into the glandular trichomes occurring on the leaves and, to a major extent, on the flower bracts. In the last few years, hemp for production of high-value chemicals became a major commodity in the U.S. and across the world. The hypothesis was that hemp biomass valorization can be achieved through distillation and procurement of two high-value products: the essential oil (EO) and cannabinoids. Furthermore, the secondary hypothesis was that the distillation process will decarboxylate cannabinoids hence improving cannabinoid composition of extracted hemp biomass. Therefore, this study elucidated the effect of steam distillation on changes in the content and compositional profile of cannabinoids in the extracted biomass. Certified organic CBD-hemp strains (chemovars, varieties) Red Bordeaux, Cherry Wine and Umpqua (flowers and some upper leaves) and a T&H strain that included chopped whole-plant biomass, were subjected to steam distillation, and the EO and cannabinoids profile were analyzed by gas chromatography-mass spectrometry (GC–MS) and HPLC, respectively. The distillation of hemp resulted in apparent decarboxylation and conversion of cannabinoids in the distilled biomass. The study demonstrated a simple method for valorization of CBD-hemp through the production of two high-value chemicals, i.e. EO and cannabinoids with improved profile through the conversion of cannabidiolic acid (CBD-A) into cannabidiol (CBD), cannabichromenic acid (CBC-A) into cannabichromene (CBC), cannabidivarinic acid (CBDV-A) into cannabidivarin (CBDV), cannabigerolic acid (CBG-A) into cannabigerol (CBG), and δ-9-tetrahydrocannabinolic acid (THC-A) into δ-9-tetrahydrocannabinol (THC). In addition, the distilled biomass contained CBN while the non-distilled did not. Distillation improved the cannabinoids profile; e.g. the distilled hemp biomass had 3.4 times higher CBD in variety Red Bordeaux, 5.6 times in Cherry Wine, 9 times in variety Umpqua, and 6 times in T&H compared to the original non-distilled samples, respectively. Most of the cannabinoids remained in the distilled biomass and small amounts of CBD were transferred to the EO. The CBD concentration in the EO was as follows: 5.3% in the EO of Umpqua, 0.15% in the EO of Cherry Wine and Red Bordeaux and 0.06% in the EO of T&H. The main 3 EO constituents were similar but in different ratio; myrcene (23.2%), (E)-caryophyllene (16.7%) and selina-3,7(11)-diene (9.6%) in Cherry Wine; (E)-caryophyllene (~ 20%), myrcene (16.6%), selina-3,7(11)-diene (9.6%), α-humulene (8.0%) in Red Bordeaux; (E)-caryophyllene (18.2%) guaiol (7.0%), 10-epi-γ-eudesmol (6.9%) in Umpqua; and (E)-caryophyllene (30.5%), α-humulene (9.1%), and (E)-α-bisabolene (6.5%) in T&H. In addition, distillation reduced total THC in the distilled biomass. Scanning electron microscopy (SEM) analyses revealed that most of the glandular trichomes in the distilled biomass were not disturbed (remained intact); that suggest a possibility for terpenes evaporation through the epidermal membrane covering the glandular trichomes leaving the cannabinoids in the trichomes. This explained the fact that distillation resulted in terpene extraction while the cannabinoids remained in the distilled material.

Introduction

Industrial hemp (Cannabis sativa L.) was grown as a commodity fiber crop in North America until the mid-1930s. Hemp was banned and was considered an illegal crop in the United States for several decades. In 2014, section 7606 of the U.S. Congress Agricultural Act of 2014, the “Farm Bill”, authorized pilot programs on cultivation of industrial hemp, defined as “the plant Cannabis sativa L. and any part of such plant, whether growing or not, with a delta-9 tetrahydrocannabinol (THC) concentration of not more than 0.3% on a dry weight basis”. The 2018 Farm Bill decriminalized cultivation of industrial hemp and designated the U.S. Department of Agriculture (USDA) Agricultural Marketing Service to develop regulations. Hemp production in the U.S. is increasing rapidly and there were up to 500,000 licensed acres to grow hemp in 2019 1 , that would have produced $11.3 billion of income, or around 6% of the total value of all cash crops in this country 1 . Currently, at least 47 states have passed legislation to establish hemp production programs or allow for hemp cultivation research. At this time, hemp is prohibited only in Idaho, and Mississippi. Specific state legislation varies from state to state. Currently, Oregon legal environment with respect to commercial hemp production is among the most reassuring in the U.S. and hence, stimulating hemp production for high-value chemicals.

Most of the hemp grown in the U.S. is for production of high-value chemicals such as cannabinoids and terpenes. Essential oil (EO) production is a novel use of hemp, and as such, it needs to be researched. Hemp for EO and cannabinoids production is an understudied, high-value crop, with many pending unanswered questions.

Hemp synthesizes and accumulates numerous secondary metabolites 2,3,4 . The most important of these are the cannabinoids and terpenes; they are toxic to many organisms and are considered to be plant protective chemicals. Hemp chemicals have numerous uses due to their bioactivities 5,6,7,8,9,10 .

Hemp (C. sativa) is an annual, normally wind pollinated dioecious plant (separate male and female plants), although monoecious forms can also occur naturally. Botanically, hemp belongs to Cannabaceae. There has been a debate on whether hemp is a single species or include other species such as Cannabis indica Lam. and Cannabis ruderalis Janisch. Small and Cronquist 11 separated the species into two subspecies, subsp. indica (Lam.) E. Small & Cronq., with relatively high amounts of the psychotropic constituent THC, and subsp. sativa with low amounts of THC. According to this systematics, the modern fiber and grain industrial hemp varieties would belong to subsp. sativa. Therefore, most recreational, or medical marijuana varieties and strains would belong to subsp. indica. However, there are numerous hybrids blurring the line. Overall, botanists consider C. sativa to be a single species with several subspecies 12,13,14 .

Hemp plants form different epidermal trichomes, which are considered defense structures to reduce herbivory by making the biomass less palatable. Cystolith trichomes contain calcium carbonate particles. These trichomes are present in great numbers on both leaf surfaces along with the slender non glandular trichomes 13 . In addition, hemp forms secretory or glandular trichomes, the sites for EO (terpenes) synthesis and accumulation, with the highest density in non-fertilized flower bracts (Figs. 1, 2). Current understanding is that secretory trichomes are also the site where cannabinoids are synthesized and accumulate 3,14,15 . Most of the hemp chemicals are produced in multicellular glandular trichomes, which can be sessile glands (with very short stalks), or long-stalk secretory glands (Figs. 1, 2). The top of these glands is a cavity covered by a waxy cuticle, where the resin (a mix of cannabinoids and terpenes) is accumulated. Since the waxy cuticle of the glands is a thin layer, it can easily be ruptured resulting in a release of its contents. The density of secretory glands differs, with the highest concentration found in perigonal bracts covering the female flowers. Therefore, traditionally, flowers have been the plant part of the most interest because of their high content of various natural products 2,14,15 .

(A) Hemp abaxial (lower) leaf surface with glandular trichomes, and slender cystolithic non glandular trichomes. (B) Hemp adaxial (upper) leaf surface with an abundance of cystolithic trichomes and few sessile glandular trichomes. (C) Hemp leaf petiole with an abundance of cystolithic and slender non glandular trichomes and few sessile glandular trichomes. (D) Flower bract densely covered with glandular trichomes. (E) Close up of flower bract with glandular trichomes and slender non glandular trichomes. (F) Detached sessile glandular trichomes from hemp leaves.

Non-extracted Red Bordeaux flower part with glandular trichomes.

Hemp plants contain a whole array of chemicals that may act synergistically or antagonistically. Currently, the pharmacological power of the C. sativa is based on the content of δ-9-tetrahydrocannabinolic acid (THC-A) and cannabidiolic acid (CBD-A) 16 . Other major cannabinoids include cannabinolic acid (CBN-A), cannabigerolic acid (CBG-A), cannabichromenic acid (CBC-A), and cannabinodiolic acid (CBND-A) 2,17 . With recent legalization of hemp in many countries, researchers are now focusing on better understanding of the role of various other chemicals found in hemp 2,18 . Terpenes (that are constituents of the hemp EO) contribute to the aroma of various hemp genotypes, and so far, around 140 different terpenes have been reported in hemp 2,14,19,20 . The major ones belong to the class of monoterpenes (e.g., α-pinene and myrcene) and sesquiterpenes ((E)-caryophyllene, and caryophyllene oxide) 21 .

The hypothesis was that CBD-hemp biomass valorization can be achieved through distillation and production of two high-value products: EO and cannabinoids. Furthermore, a preliminary distillation process may decarboxylate cannabinoids and therefore improve cannabinoid composition of extracts from the residual biomass.

Results

Essential oil (EO) content (yield) and composition of Cherry Wine (CW), Red Bordeaux (RB), Umpqua (Umpq) and T&H

The EO yield (% in dry biomass) was highest in CW and RB (1.85 and 1.6%, respectively), lower in Umpqua (0.72%), and the lowest in T&H (0.37%) strains (Table 1). The lower EO content in T&H was most probably because the biomass was chopped by the grower; it included all plant parts (stems, leaves, flowers), and therefore there is dilution factor in addition to the chopping that may have destroyed some of the glandular trichomes resulting in terpene evaporation.

Table 1 Essential oil yield and composition obtained by non-stop steam distillation for 240 min of autoflower type hemp biomass of Cherry Wine organic (CW), Red Bordeaux organic (RB), Umpqua organic (Umpq), and non-stop steam distillation for 120 min of chopped biomass of autoflower type hemp T&H.

The EO chemical profile of the four strains was also different. Cherry Wine and Red Bordeaux had higher concentrations of myrcene compared with Umpqua and T&H. Limonene was around 4–5% in Cherry Wine, Red Bordeaux and Umpqua but < 1% in T&H. Conversely, (E)-caryophyllene was much higher in T&H (30.1%) and lower in the other 3 hemp strains. α-trans-Bergamotene was also higher in T&H and much lower in the other 3 hemp strains.

α-Humulene and α-bulnesene, (E)-α-bisabolene, caryophyllene oxide, and epi-α-bisabolol were also higher in the EO of T&H and lower in the EO of the other three strains. The highest concentration of guaiol, 10-epi-γ-eudesmol, bulnesol, and cannabidiol (5.3%) were found in the EO of Umpqua. The concentration of cannabidiol was < 0.2% in the EO of the other three strains. α-Guaiene was only found in T&H and in Umpqua, cannabidivarin and cannabicitran were only detected in the EO of Umpqua, (E,E)-α-farnesene (2.1%) was only found in the EO of T&H.

Cherry Wine EO contained myrcene (23.2%), (E)-caryophyllene (16.7%), selina-3,7(11)-diene (9.6%), as the three main constituents (> 10% of total oil) (Table 1). The Red Bordeaux main EO constituents were (E)-caryophyllene (~ 20%), myrcene (16.6%), selina-3,7(11)-diene (9.6%), and α-humulene (8.0%).

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The EO of Umpqua had (E)-caryophyllene (18.2%) as the main constituent, other constituents included guaiol (7.0%), 10-epi-γ-eudesmol (6.9%), selina-3,7(11)-diene (5.6%), cannabidiol (5.3%), and α-humulene (5.3%). (E)-Caryophyllene (30.5%) was the main constituent of T&H strain; other constituents included α-humulene (9.1%), (E)-α-bisabolene (6.5%), epi-α-bisabolol (6.0%), α-bulnesene (6.0%), and caryophyllene oxide (5.1%) (Table 1).

Effect of distillation on cannabinoids

The distillation of hemp biomass resulted in two high-value products: essential oil (EO) and distilled biomass with largely preserved but altered cannabinoids because of the decarboxylation that occurs during the distillation. Most notable, the distillation of hemp resulted in apparent decarboxylation and conversion of cannabinoids in the distilled biomass. One of the notable conversions of interest is the decarboxylation of CBD-A into CBD (Table 2). This was observed in all four different strains (chemovars). Distillation of the biomass slightly increased the concentration of total CBD in Cherry Wine and decreased it slightly in Red Bordeaux. Overall, the total CBD ranged from 2.3 to 11.7% and from 2.1 to 12.7% in the non-distilled and distilled biomass, respectively.

Table 2 Cannabinoid content (%) in distilled and not distilled biomass of 4 varieties, transplanted autoflower type hemp plants (mean ± std.err.; n = 2).

Similarly, distillation resulted in the decarboxylation of CBC-A into CBC; the concentration of CBC in the distilled biomass increased 4.1, 2.8, and 5.2 times in Cherry Wine, Red Bordeaux, Umpqua relative to the non-distilled biomass, respectively, and from 0 to 0.123%, in T&H. There was concomitant decrease of CBC-A from non-distilled to distilled biomass.

Similar tendency was observed with the conversion of CBG-A into CBG in Cherry Wine, Red Bordeaux, and Umpqua; CBG-A in the distilled biomass was below the detection limit of the instrument. Overall, distillation resulted in slight decrease of total CBG in Cherry Wine and Red Bordeaux and slight increase in the total CBG in Umpqua. The CBG-A and CBG in T&H were both under the detection limit.

The concentration of CBN in not-distilled biomass was under the detection limit and was 0.041, 0.035, and 0.075% in the distilled biomass of Cherry Wine, Red Bordeaux and Umpqua, respectively, while it was under the detection limit in T&H.

As expected, distillation resulted in conversion of all THC-A into THC. This has both practical and legal importance; some states limit the concentration of THC in hemp while others limit the concentration of total THC. The concentration of THC in the distilled biomass was 197, 124, and 236% in Cherry Wine, Red Brodeau, and Umpua, relative to their respective concentrations in the not-distilled biomass, respectively. Overall, distillation tended to increase the concentration of total THC in Cherry Wine but decreased it a bit in the rest of the hemp strains (Table 2).

Scanning electron microscopy (SEM) of the distilled biomass

Scanning electron microscopy (SEM) analyses revealed that most of the glandular trichomes in the distilled biomass were not disturbed, they were not open (Fig. 3A–E). That suggest a possibility for terpenes evaporation through the epidermal membrane covering the glandular trichomes leaving the cannabinoids in the trichomes. This explained the fact that distillation resulted in terpene extraction while the cannabinoids remained in the distilled material. Furthermore, mechanical harvest and chopping of the T&H biomass resulted in damage of some of the glandular trichomes (Fig. 4A), however, it seems while some of the terpenes may have evaporated, some may have formed a resinoid-like slush with the cannabinoids that did not volatilize. Furthermore, an open sessile gland in T&H after the extraction of the EO (Fig. 4B) indicates similar resinoid-like substance that can be assumed to contain mostly cannabinoids.

(A) Red Bordeaux extracted flower/leaf parts. (B) Red Bordeaux extracted flower/leaf parts. (C) Red Bordeaux extracted leaf with non-destructed glandular trichomes. (D) Red Bordeaux extracted leaf with non-destructed glandular trichomes and well preserved cystolithic trichomes. (E) Cherry Wine extracted flower/leaf parts.

(A) T&H non-extracted leaf with part of the sessile gland missing probably due to the mechanical chopping of the biomass, revealing resinoid substance inside that could be a mix of the cannabinoids and some of the terpenes that did not volatilize. (B) T&H Extracted leaf part with part of the sessile gland missing revealing resinoid substance inside that could be the cannabinoids and some of the non-extracted terpenes.

Discussion

This study demonstrated that distillation of hemp biomass may extract the terpenes (EO) and leave the cannabinoids in the distilled biomass that can be further extracted. This presents an opportunity for valorization of hemp biomass because of the resulting two high-value products: essential oil (EO) and distilled biomass with largely preserved but altered (into desirable chemical forms) cannabinoids because of the decarboxylation that occurs during the distillation.

Secondly, the study reveal that the above effects may depend on the specific variety (strain, cultivar) as some CBD was transferred into the EO of one of the tested strains but not in the other three. Still, most of the CBD stayed in the distilled biomass. The extracted biomass did not possess any aroma because the volatile terpenes were extracted. That presents an opportunity for the extracted biomass to be included in various products with targeted designed aroma and flavor of choice.

The SEM analyses of distilled biomass revealed that the thin layer covering the glands of the glandular trichomes were not open suggesting that terpenes may have moved through this membrane during distillation leaving the cannabinoids in the glands.

Third, the EO yield, and profile of different strains can differ significantly as a function of the variety (genetics); the major EO constituents can be either the same but in the different concentration gradients, or the 3–5 main EO constituents could be different in different strains. That presents an opportunity to obtain EO with specific composition and subsequently aroma, that would be of interest to the aroma and flavor industries.

Overall, the EO yield in this study clearly showed that the hemp strains tested in this study were very different from the typical registered industrial hemp varieties listed in the European Union (EU) 22 and in Canada 23 . The EO yield of the hemp strains in this study varied from 0.72 to 1.85% in dried flowers and upper leaves except for the chopped whole plant biomass of T&H which was 0.37%. Recent literature data showed that the EO yield of 8 industrial hemp breeding lines was between 0.06 and 0.14%, while the EO yield of other 8 registered industrial hemp varieties was 0.1–0.2% (mL per 100 g air-dried hemp biomass) 24 . Other studies on industrial hemp have reported EO yield of 0.04–0.3% 3,5,6,9,25,26,27 .

There are two reasons for the higher EO content of the high-value (high-cannabinoids) hemp used in this study: (1) the four strains in this study were selected in the past from the medical or illicit marijuana strains that have different architecture (phenotype) and genotype than the registered industrial hemp varieties; and (2) three of the strains in this study were established using feminized seed and care was taken to avoid pollination and fertilization of the female flowers, that results in higher density of glandular trichomes (Fig. 1D). The T&H was grown until late, and harvested with a forage chopper that resulted in EO losses (Fig. 4A,B).

Myrcene and (E)-caryophyllene were two of the main EO constituents in the hemp strains in this study. Myrcene has been reported as a major EO constituent in industrial hemp, ranging from negligible amounts to 25% of the EO 3,5,21,26,27,28,29 . Also, myrcene is found in higher concentrations in hops EO depending on the distillation time 30 . The importance and the use of myrcene, acyclic monoterpene, has been reviewed 31 ; it is a constituent in the EO of many other species such as hop, lemongrass, nutmeg, sage, rosemary and others 31,32 . However, the major raw material for myrcene has been turpentine 31 . Other chemicals such as menthol, geraniol, nerol, linalool can be commercially produced from myrcene, and these products have wide and various applications such as flavor and fragrance agents, in insect repellents, vitamins and also in polymers, pharmaceuticals and surfactants 31 . However, myrcene has been touted as potential carcinogen, and suggested that food and beverages with myrcene should be monitored 32 . Indeed, research has shown myrcene was linked to tumor in the urinary tracts of rodents although no data is available for humans 33 .

(E)-Caryophyllene, a bicyclic sesquiterpene, has been reported as a constituent of industrial hemp EO ranging from 14 to 33% of the total oil 3,26,28 . (E)-Caryophyllene is a known anti-inflammatory agent, that possesses also analgesic action; it is used as food additive/flavoring agent, has many other biological properties 34,35 . It is found in industrial hemp varieties from 22 to 55% in registered varieties and from 11 to 22% of the EO of breeding lines 36 . (E)-Caryophyllene is considered a dietary cannabinoid and in vivo, it was reported to act as non-psychotropic CB2 receptor ligand in foodstuff 37 . (E)-Caryophyllene is found in the EO of other plant species such as peppermint (Mentha × piperita L.), common basil (Ocimum basilicum L.), oregano (Origanum vulgare L.) black pepper (Piper nigrum L.), and has been known to possess insecticidal, acaricidal, repellent, and antifungal properties 10,35,38 .

Recent study on 8 registered industrial hemp varieties in Europe (in Serbia, which is approximately at the same latitude as Oregon) has shown the following main EO constituents: (E)-caryophyllene 11–22% and 15.4–29.6%; α-humulene 4.4–7.6% and 5.3–11.9%; caryophyllene oxide 8.6–13.7% 36 . The major EO constituents of the U.S. high-cannabinoid hemp strain that was grown in the close vicinity to the above study in Serbia had different chemical profile, with major constituents as myrcene (9.2 to 12%), (E)-caryophyllene (6.5 to 7.5%), limonene (3.8 to 4.2%), (E)-β-ocimene (5.3 to 5.6%) and α-bisabolol (3.9 to 4.4%) 36 . Therefore, we may postulate that the high-cannabinoid U.S. hemp strains will synthesize and accumulate similar cannabinoids and EO amount and composition in other remote geographic areas at similar latitude.

Conclusions

This study elucidated the effect of the steam distillation of four high-cannabinoids hemp strains on changes in the content and compositional profile of cannabinoids. The study demonstrated a simple method for valorization of CBD-hemp through the production of two high-value chemicals; EO and cannabinoids with improved profile through the conversion of CBD-A into CBD, CBC-A into CBC, CBDV-A into CBDV, CBG-A into CBG, and THC-A into THC. In addition, the distilled biomass contained CBN while the non-distilled did not. Distillation improved cannabinoids profile; e.g. the distilled hemp biomass had 3.4 times higher CBD in variety Red Bordeaux, 5.6 times in Cherry Wine, 9 times in variety Umpqua, and 6 times in T&H compared to the original non-distilled samples, respectively. The main 3 EO constituents were similar but in different ratio. The distillation converted most of the THC-A into THC reducing total THC in the process, which carries practical and legal importance because of the rapidly changing legal environment in the U.S. and across the world. Scanning electron microscopy (SEM) analyses revealed that most of the glandular trichomes in the distilled biomass were not disturbed (open); that suggest a possibility for terpenes evaporation through the epidermal membrane covering the glandular trichomes leaving the cannabinoids in the trichomes.

Methods

Plant material

The plant material utilized in this study was from varieties (strains) of cultivated hemp (Cannabis sativa L.) in the United States and this is not an endangered species at risk of extinction. The collection of plant tissue research specimens was acquired (including transportation) conformed scrupulously to procedures and regulations adopted under international legal agreements. In addition, the plant material sampling, transportation, and handling was in compliance with the U.S. federal and Oregon state legislations. Certified and compliant (THC < 0.3% in dry biomass) organically grown CBD-hemp strains (also called chemovars, varieties) Red Bordeaux, Cherry Wine and Umpqua (flowers and some upper leaves) and a T&H strain that included chopped whole-plant biomass were donated by two licensed Oregon hemp producers. The original Certificates of analyses are kept and available from the authors. We are using “strain” to denote non-registered hemp variety (cultivar); this is a common term in the hemp industry in the U.S.

Distillation of the essential oil (EO)

Representative subsamples in 3 replicates from each of the four hemp strains were subjected to steam distillation for 240 min in 2-L steam distillation apparatuses as described previously 39 . The first drop of the EO in the separator part of the apparatus was considered the beginning of the distillation. After 240 min non-stop distillation, the power was switched off, the heat source was removed, the EOs were collected in glass vials and stored in a freezer. Later, the EO was separated from the remaining water in the vials, its weight was taken on analytical scale, and transferred to a freezer again until the gas chromatography (GC) analyses could be performed.

The remaining hemp biomass was removed from the bioflask and spread for drying at T around 30 °C at forced air. After the biomass reached a constant weight, subsamples were generated for cannabinoid extraction.

Cannabinoid extraction and identification

Subsamples from non-extracted (original) and extracted biomass was submitted for cannabinoid analyses and characterization to the Columbia Laboratories in Portland, OR (https://www.columbialaboratories.com/), a commercial laboratory that is ISO 17025:2017 accredited, as well as TNI certified. The method of cannabinoid extraction and analyses was JAOAC 2015 V98-6 20 and the instrumentation was HPLC–DAD Agilent 1200 series (Agilent Technologies, Inc. Santa Clara, CA, U.S.A).

Gas chromatography-mass spectrometry (GC–MS) analyses of the essential oils

A gas chromatograph Agilent 6890 N equipped with a single quadrupole mass spectrometer 5973 N was used. The stationary phase was a HP-5MS (30 m l. × 0.25 mm i.d., 0.1 mm f.t., Folsom, CA, USA) made up of 5% phenylmethylpolysiloxane; the mobile phase was helium (99.999%) flowing at 1 mL/min. The temperature of the oven was programmed as follows: 60 °C held for 5 min, then increase up to 220 °C at 4 °C/min, finally 11 °C/min up to 280 °C held for 15 min. Once diluted in n-hexane (dilution ratio 1:100) the hemp EO samples were injected (2 μL) through an auto-sampler 7863 (Agilent, Wilmingotn, DE) in the inlet of GC taken at 280 °C using the split mode (split ratio 1:50). Peaks were acquired in full scan mode (29–400 m/z) using the electron impact (EI) mode at 70 eV. Chromatograms were analyzed by the Enhanced Data Analysis program of Agilent G1701DA GC/MSD ChemStation. In addition, the NIST Mass Spectral Search Program for the NIST/EPA/NIH EI was used for peak assignment. Mass spectra (MS) of peaks were compared with those stored in ADAMS 40 (Adams, 2007), NIST 17 and FFNSC3 libraries. The temperature-programmed retention indices (RI) were determined using a homologue mixture of C8-C30 n-alkanes (Merk, Milan, Italy) and computed by the following formula (ref. 41 ):

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where n is the number of carbon atom of the alkane eluting before the unknown peak, tx the retention time of the unknown peak, tn the retention time of the alkane eluting before the unknown peak and tn + 1 the retention time of the alkane eluting after the unknown peak. The combination of the MS overlapping and RI coherence with respect to those reported in the aforementioned libraries was used to assign the peak. Furthermore, for the following compounds the identity was confirmed by comparison with analytical standard: α-pinene, camphene, sabinene, β-pinene, myrcene, p-cymene, limonene, 1,8-cineole, (Z)-β-ocimene, (E)-β-ocimene, γ-terpinene, terpinolene, linalool, borneol, α-terpineol, (E)-caryophyllene, α-humulene, (E)-β-farnesene, (E)-nerolidol, caryophyllene oxide, cannabidiol (Merck). The relative peak area percentages were obtained from the chromatograms without using correction factors. The GC–MS response resulted similar to that of GC-FID as determined previously 21 .

Scanning electron microscopy (SEM) analysis of hemp flowers, glands, leaves and stems

The scanning electron microscope (SEM) used in this investigation of hemp biomass extracted and non-extracted samples was an FEI Quanta 600 SEM (ThermoFisher Scientific/FEI, Hillsboro, OR, U.S.A.) at the Microscopy Facility at Oregon State University, (https://emfacility.science.oregonstate.edu/). Samples were placed into a fixative, 1% paraformaldehyde and 2.5% glutaraldehyde in 0.1 M sodium cacodylate buffer with pH 7.4, soaked in the fixative for 2 h, rinsed in 0.1 M cacodylate buffer, 15 min each, and dehydrated in acetone (10%, 30%, 50%, 70%, 90%, 95%, 100%), 10–15 min each, followed by critical point drying (two ‘bomb flushes’ at chamber pressure to 5 °C, fill chamber with CO2). The samples were left to vent for 5 min, and then, the procedure was repeated. The dry samples were mounted onto an aluminum SEM stub with double stick carbon tape. Samples were sputter coated with a Cressington (Cressington Scientific Instruments, Watford, U.K.) 108A sputter coater from Ted Pella with Au/Pd, 60/40 mix.

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Acknowledgements

We are thankful to the two licensed Oregon hemp producers (Cook Family Farms and Libosoils LLC) for providing certified and compliant hemp material for this study. We thank Ms. Teresa Sawyer for the help with the Scanning Electron Microscopy sample preparation and analyses. Funding was provided by Oregon State University.

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These authors contributed equally: Valtcho D. Zheljazkov and Filippo Maggi.

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Crop and Soil Science Department, Oregon State University, 3050 SW Campus Way, Corvallis, OR, 97331, USA

Valtcho D. Zheljazkov

School of Pharmacy, University of Camerino, via Sant’ Agostino 1, 62032, Camerino, Italy

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V.D.Z. conceived the experiments, V.D.Z and F.M. conducted the experiments, and analysed the results. Authors reviewed the manuscript and approved it for publication.

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Zheljazkov, V.D., Maggi, F. Valorization of CBD-hemp through distillation to provide essential oil and improved cannabinoids profile. Sci Rep 11, 19890 (2021). https://doi.org/10.1038/s41598-021-99335-4

Received : 25 April 2021

Accepted : 23 September 2021

Published : 06 October 2021

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CBD Extraction: CO2, Steam Distillation, and More

We’d like to thank CBDfx and Natural Hemp Solutions for supplying us with images of the processes used in their labs.

Cannabidiol, or CBD for short, is an organic compound that is found in the cannabis plant, with the flowers of the hemp plant being the richest source. And in order for CBD to be added to a wide array of consumer products—think CBD oil, lotions, topicals, or CBD vape juice—the first step that manufacturers need to take is to extract it from the plant.

This guide will present the various CBD extraction methods, essentially explaining how full-spectrum CBD oil is obtained from the CBD strains of cannabis. Some of these methods have been used in various industries for decades or even centuries, far before CBD oil was even a thing. Examples include essential oil extraction, decaffeination (and caffeine extraction) of coffee beans, and even beer production. In all cases, the idea is the same: how to extract a valuable resource out of plant material.

If you are interested in the ins and outs of CBD extraction from cannabis strains high in CBD, here’s a breakdown of the most commonly used CBD methods.

Supercritical CO2 extraction

The word “supercritical” sounds real fancy, but it is actually a term that’s very commonly used in chemistry. Simply put, a substance in its supercritical state possesses characteristics of both a gas and a liquid.

When supercritical CO2 is used in CBD extraction, its gas properties allow it to effuse through all plant matter, while its liquid properties allow it to extract compounds efficiently. The exact process varies, and some labs start the extraction with liquid CO2 while others start with CO2 in gas form. In both cases, manufacturers add CO2 in a chamber that includes plant material and use the exact amounts of pressure and temperature needed for CO2 to reach its supercritical state. At this point, and with the help of some additional heat, CO2 acts as a solvent and causes the plant material to separate, carrying with it all the essential compounds. Once done, CO2 is separated from the organic compounds, and manufacturers are left with full-spectrum CBD oil.

See also  Laced CBD Gummies

While it requires qualified personnel and there are higher costs associated with the equipment needed for supercritical CO2 extraction, it is by far the most efficient and quickest method to extract CBD. It is also environmentally friendly due to the limited amount of emissions, and safer than extractions that use certain solvents as CO2 is “generally regarded as safe” by the FDA.

  • The most efficient method
  • CO2 is regarded as generally safe
  • Quick (once everything is in place)
  • Environmentally safe
  • Expensive (equipment costs)
  • Needs qualified personnel

Steam distillation

Steam distillation is a centuries-old process that’s commonly used to distill alcohol as well as extract essential oils from organics. The process is much less complicated than CO2 CBD extraction. First, plant matter is introduced in a distillation tank. With the use of water and heat, the produced steam carries oils to the top of the tank, and it is then passed through a condenser, resulting in a mix of water and oil. The mix then goes through further distillation to separate water and oil, and the result is full-spectrum CBD oil.

While this CBD extraction process is much simpler, there are some downfalls. It is more prone to error, much less efficient, and may potentially damage part of the essential oil profile of the plant. Due to these reasons, steam distillation is very rarely used to extract CBD nowadays, but many labs still use some type of distillation in the process of isolating CBD from full-spectrum oil.

  • Relatively easy to perform
  • Low cost
  • Not very efficient
  • Not consistent
  • Resulting CBD oil is less potent

Solvent extraction

This method is also centuries old and is somewhat of a middle point between CO2 extraction and steam distillation when it comes to complexity and efficiency. It bears many similarities to CO2 extraction, albeit without the advanced methodology that’s behind the “supercritical” part.

In layman’s terms, this type of extraction involves mixing plant material with some type of solvent that will carry the essential oils given the right conditions and enough time. Some of the most popular natural solvents are alcohol (ethanol) and natural plant oils (including olive oil), with alcohol being much more efficient in dissolving the plant’s compounds. But due to the higher cost associated with ethanol, many manufacturers choose to go with synthetic solvents (hydrocarbons like butane or hexane), which may end up in lower quality, or even CBD oil that’s unfit for consumption if they’re not removed properly from the final product.

Solvent extraction is a delicate CBD extraction process and its pros and cons, as well as the consistency of the resulting oil, varies greatly depending on the solvent used. It can be more efficient than steam distillation if performed properly, but it carries a lot of risk and most labs choose CO2 extraction if they can afford it.

  • More efficient than steam distillation
  • Can be performed with natural oils
  • Relatively safe if natural oils are used
  • Varied results in final product
  • Not as efficient as CO2 extraction
  • Synthetic solvents are dangerous to handle
  • Synthetic solvents need to be completely removed from final product

How to extract CBD at home

At this point, you may be wondering if there’s any way you can extract CBD at the comfort of your own home. The short answer is “yes”, but it really depends on how willing you are to do further research. The following is not going to be a real step-by-step guide, but it can serve as a starting point and give you some basic guidelines.

Olive oil extraction

Possibly the simplest way to extract CBD oil, as it only requires some CBD-rich bud, olive oil, and some basic kitchen equipment to ensure a steady supply of heat. If you’ve ever made cannabutter, then technically you have already utilized this method before. The only difference in this case, is that you are using hemp and olive oil—but olive oil can easily be swapped out for the oil or butter of your choice. This includes regular butter, coconut oil, hempseed oil, etc.

The first step for olive oil extraction is decarboxylation, i.e. activation of the compounds of plant material with the use of heat (there’s more info in the following section). Trimmed hemp flower in an oven tray heated between 240 and 280°F (115-135°C) for up to an hour should do the trick. Once this step is taken care of, the resulting activated cannabis is mixed with olive oil and heated at low temperature (ideally in a double boiler) for around two hours. The only thing left to do at this point is to use a filter to strain the mixture and separate the oil from the plant material. The result: CBD-infused olive oil.

While this is the easiest and least risky way to extract CBD oil, it is certainly not the most efficient. As with most DIY projects, there’s always room for user error. But even if you do everything right, you are going to sacrifice a large part of the organic compounds of the plant and you will produce less potent oil than a lab would. For these reasons, extracting CBD at home is an interesting experiment, but if you want to reap all the benefits of CBD it is advisable to get it from a reputable source instead.

Activation and purification

While technically not steps of CBD extraction, activation of active organic compounds and purification of CBD oil are two processes that are very important in CBD production. The most common methods used for these purposes are decarboxylation and winterization.

Decarboxylation

The active organic compounds of the cannabis plant come in their acidic forms. In order to go from THCA and CBDA to THC and CBD, manufacturers need to apply heat and decarboxylate the compounds—that’s the lab equivalent to lighting up a joint. Heat removes a carbon molecule from the organic compounds and turns them into their active counterparts.

Decarboxylation may take place before or after the extraction, and the exact methodology followed is highly dependent on this choice. But it is an essential part of the CBD oil production process, as non-activated compounds have little to no effect on the user.

Winterization

While not as essential as carboxylation, winterization is a very common process that ensures that the final product of the extraction is as pure as possible. Simply put, the process of winterization employs solvents (usually ethanol) and low temperatures to ensure that lipids and other impurities are removed from an oil extract. This takes place as one of the final steps before full spectrum oil is obtained.

Winterization is not always performed, but it is a very important process when the final product is intended to be vaped. Some terpenes and other compounds are also filtered out during this process, but many manufacturers choose to add terpenes to their CBD oil after winterization.

CBD extraction: the takeaway

These are the most commonly used CBD extraction methods and, as expected, each comes with its own advantages and disadvantages. The main takeaway from this guide should be that the reason you may have seen “supercritical CO2 extraction” in ads and promotions is not just that it sounds cool (although it does!) Simply put, CO2 extraction is by far the cleanest and most efficient CBD extraction method—and a no-brainer for any lab that can actually afford it.

This doesn’t mean that all CO2-extracted CBD products are better by definition. But if a lab invests in the equipment that’s required for the most technically demanding extraction method, chances are that they know what they are doing. When in doubt, check lab tests, and always choose third-party tested CBD products from reputable sources.

An Overview of the Cannabis and Hemp Oil Distillation Process

Are you looking to improve your cannabis and hemp oil extraction methods? In this blog, Maratek is going to give an overview of the cannabis and hemp oil distillation process and how it can help to create a consistent pure product.

What is distillation?

Distillation is a process that heats a substance into a vapor and cools it back to a liquid. This process can be used to separate components with different boiling points. There are different variations of this process, which are all dependent on the components, and the temperature, and pressure of the system.

Simple distillation is appropriate for the separation of materials that have significantly different boiling points. When heated the liquid that is more volatile will vaporize and travel through the system, recondensing into a liquid when it passes through a chilled condenser. This results in the volatile substance becoming separated from the initial product.

How is distillation used for cannabis oil?

The cannabis and hemp industry uses distillation to further purify crude oil. The extraction process generally uses solvents such as ethanol, or CO2 to remove the crude oil from the plant biomass. The distillation equipment then takes the crude oil and produces a pure product, usually of either THC or CBD distillate by removing other volatiles and contaminants.

Distillation can take multiple passes to remove all unwanted compounds before producing the intended final product. The first pass usually removes low boiling point volatiles. A second pass focuses on distilling the desired cannabinoids, leaving behind other contaminants such as waxes, sugars and any leftover plant material. This results in a pure product of the desired cannabinoids or terpenes depending on a company’s intention.

Multiple passes can be necessary especially if a company does not use a winterization process on their products . Winterization removes any contaminants like fats, and waxes from the initial oil extraction. Without this process those contaminants are left in the solution and will need to be removed during distillation to produce a pure final product. Setting up multiple distillation equipment that are connected directly to each other reduces the need for multiple passes through a singular system.

The most common form of distillation system is short path distillation. It is beneficial because the vapor travels a shorter distance before it is condensed, allowing the equipment to take up less space. The crude oil is deposited at the bottom of a flask where it is then heated to initiate the distillation process. This system generally gets used on a smaller scale, as it typically needs more manual operation or oversight.

A similar equipment is the wiped film distillation system. The only difference to the above system is the introduction of a wiper blade that spreads a layer of the initial feed product onto the chamber walls. This thin layer reduces the amount of time heat is applied to the product. Prolonged exposure to heat can degrade a cannabis product and this equipment reduces that risk. The wipers also provide an even spread that supports more consistent evaporation and condensation rates.

The popularity of wiped film short path distillation may also be attributed to its continuous feed abilities that increase output and efficiency. Continuous feed supports operation by helping to produce large quantities and maintaining consistency. This process is more automated due to continuous feed and the wipers and is therefore more suitable for large scale operations.

Temperatures and pressures used in a system can usually be altered to address a business’s specific goals. Changing the pressure can affect the temperatures at which certain compounds boil at, making it easier to remove them from the product. If boiling temperatures are lowered, this also decreases the risk of overheating and degrading the product.

Distillation is relatively simple once the extraction process has taken place. After all the undesirable materials are removed during the extraction process, the purest form of crude oil is left. As this is not a one size fits all method, the industry today requires you to focus on both scaling up for the mass market, and scaling down for smaller, more local needs.

As short path distillation requires less pressure to be exerted on the distillate, it is more common and favorable when working with volatile compounds and when purifying small amounts of substance. With heat, pressure, and humidity – it forces the remaining impurities and traces of solvent extraction residue out.

The short path causes the cannabis extract to break down into its constituent compounds. THC and CBD are separated out at different temperatures as they have slight differences in boiling points. It is more effective and has better results when it is done on a large scale using industrial level equipment. Once it is distilled, the cannabis concentrate has a higher CBD or THC content compared to the crude oil. Distillates of different cannabinoids can then be blended to customize a product.

If further purification is required, the distillate can be passed through an isolate production system to obtain up to 99.9% pure cannabinoids.

Want to learn more about the process of distillation in the cannabis and hemp extraction industry? Maratek has engineered short path distillation systems that will improve the purity of your product. Contact us today for more information .

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