CN112062658A - Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp - Google Patents
Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp Download PDFInfo
- Publication number
- CN112062658A CN112062658A CN202010852203.9A CN202010852203A CN112062658A CN 112062658 A CN112062658 A CN 112062658A CN 202010852203 A CN202010852203 A CN 202010852203A CN 112062658 A CN112062658 A CN 112062658A
- Authority
- CN
- China
- Prior art keywords
- ethanol
- mass concentration
- cbdv
- cbg
- cbd
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- REOZWEGFPHTFEI-JKSUJKDBSA-N Cannabidivarin Chemical compound OC1=CC(CCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 REOZWEGFPHTFEI-JKSUJKDBSA-N 0.000 title claims abstract description 61
- REOZWEGFPHTFEI-UHFFFAOYSA-N cannabidivarine Natural products OC1=CC(CCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 REOZWEGFPHTFEI-UHFFFAOYSA-N 0.000 title claims abstract description 60
- QXACEHWTBCFNSA-SFQUDFHCSA-N cannabigerol Chemical compound CCCCCC1=CC(O)=C(C\C=C(/C)CCC=C(C)C)C(O)=C1 QXACEHWTBCFNSA-SFQUDFHCSA-N 0.000 title claims abstract description 60
- QXACEHWTBCFNSA-UHFFFAOYSA-N cannabigerol Natural products CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1 QXACEHWTBCFNSA-UHFFFAOYSA-N 0.000 title claims abstract description 59
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 title claims abstract description 57
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 title claims abstract description 57
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 title claims abstract description 57
- ZROLHBHDLIHEMS-UHFFFAOYSA-N Delta9 tetrahydrocannabivarin Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCC)=CC(O)=C3C21 ZROLHBHDLIHEMS-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 244000025254 Cannabis sativa Species 0.000 title claims abstract description 41
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 title claims abstract description 41
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 title claims abstract description 41
- 235000009120 camo Nutrition 0.000 title claims abstract description 41
- 235000005607 chanvre indien Nutrition 0.000 title claims abstract description 41
- 239000011487 hemp Substances 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 40
- ZROLHBHDLIHEMS-HUUCEWRRSA-N (6ar,10ar)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCC)=CC(O)=C3[C@@H]21 ZROLHBHDLIHEMS-HUUCEWRRSA-N 0.000 title claims abstract description 16
- 241001471082 Colocasia bobone disease-associated cytorhabdovirus Species 0.000 title claims abstract 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 218
- 239000013078 crystal Substances 0.000 claims abstract description 66
- 238000000199 molecular distillation Methods 0.000 claims abstract description 52
- 238000000926 separation method Methods 0.000 claims abstract description 36
- 239000000843 powder Substances 0.000 claims abstract description 24
- 238000001914 filtration Methods 0.000 claims abstract description 18
- 238000001035 drying Methods 0.000 claims abstract description 12
- 238000011068 loading method Methods 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 230000008014 freezing Effects 0.000 claims abstract description 6
- 238000007710 freezing Methods 0.000 claims abstract description 6
- 238000002386 leaching Methods 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims description 30
- 238000004821 distillation Methods 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 17
- 239000000706 filtrate Substances 0.000 claims description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 8
- 239000000741 silica gel Substances 0.000 claims description 8
- 229910002027 silica gel Inorganic materials 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 5
- 230000005484 gravity Effects 0.000 claims description 5
- 230000004580 weight loss Effects 0.000 claims description 5
- JBQLQIMCKFDOHK-UHFFFAOYSA-N Stephanol Natural products CC(O)C1(O)CCC2(O)C3(O)CC=C4CC(O)CCC4(C)C3C(O)C(O)C12C JBQLQIMCKFDOHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 229950011318 cannabidiol Drugs 0.000 description 42
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 description 41
- 241000218236 Cannabis Species 0.000 description 7
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 7
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 7
- 229960004242 dronabinol Drugs 0.000 description 7
- 239000003480 eluent Substances 0.000 description 6
- 238000011031 large-scale manufacturing process Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000011160 research Methods 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000000324 neuroprotective effect Effects 0.000 description 2
- 238000011112 process operation Methods 0.000 description 2
- 230000001603 reducing effect Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- -1 CBG is cannabigerol Natural products 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000001145 Metabolic Syndrome Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000003445 Mouth Neoplasms Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010041925 Staphylococcal infections Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 208000030886 Traumatic Brain injury Diseases 0.000 description 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 230000001062 anti-nausea Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229930003827 cannabinoid Natural products 0.000 description 1
- 239000003557 cannabinoid Substances 0.000 description 1
- 230000004706 cardiovascular dysfunction Effects 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000001037 epileptic effect Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 238000011170 pharmaceutical development Methods 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000006403 short-term memory Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Botany (AREA)
- Crystallography & Structural Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp, which comprises the following steps of crushing raw materials; drying; ③ leaching: extracting, concentrating and freezing the roasted flower and leaf powder and ethanol according to the solid-to-liquid ratio of 1: 8-12; fourthly, filtering: filtering and extracting the frozen concentrated solution to obtain a hemp extract; molecular distillation: carrying out tertiary molecular distillation on the hemp extract; sixthly, chromatographic column separation: dissolving the distilled CBG, CBDV, CBD and THCV oil by using ethanol with the mass concentration of 60 percent, and then carrying out wet-process sample loading for chromatographic column separation; and (b) recrystallizing: and dissolving the prepared CBG crystal, CBDV crystal, CBD crystal and THCV oil by using ethanol respectively, recrystallizing, washing and drying to obtain finished products of CBG crystal, CBDV crystal, CBD crystal and THCV crystal. The raw material and reagent used in the invention are cheap and easily available, the cost is lower, the operation and method are simple and easy to advance, and the prepared product has high purity and good safety.
Description
Technical Field
The invention belongs to the technical field of extraction and separation of chemical components of natural plants, and particularly relates to a method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp.
Background
Industrial cannabis refers to the obtaining of legally planted cannabis containing less than 0.3% Tetrahydrocannabinol (THC). At present, legal planting and processing are obtained in Yunnan and Heilongjiang, and in recent years, industrial hemp is more and more emphasized by people, so that a large number of large healthy industries lay industrial hemp. The most valuable components of industrial cannabis are mainly Cannabigerol (CBG), Cannabidivarin (CBDV), Cannabidiol (CBD), Tetrahydrocannabidivarin (THCV), and the like.
At present, increasing anecdotal reports of patients and physicians highlight the potential of CBD as a treatment for a variety of diseases, firstly autoimmune diseases (inflammation, rheumatoid arthritis); ② nervous system disorders (alzheimer's disease, dementia, parkinson's disease, multiple sclerosis, epilepsy, huntington's chorea, stroke, brain trauma); ③ metabolic syndrome (diabetes, obesity); neuropsychiatric diseases (autism, attention deficit hyperactivity disorder, post-traumatic stress disorder, alcoholism); intestinal diseases (colitis, crohn's disease); sixthly, cardiovascular dysfunction (atherosclerosis and arrhythmia); (iii) skin diseases (acne, dermatitis, psoriasis), etc., CBD has been shown to have neuroprotective properties, whose anticancer properties are being studied at various academic research centers in the united states and elsewhere.
Sub-cannabidiol, CBDV, a phytocannabinoid naturally occurring in the cannabis plant, is structurally similar to CBD, and so far, much research has not been carried out on CBDV, which is very similar and a slightly degenerated version of cannabinoid, but small changes in the shape of the molecule are of great significance. Medical value of CBDV: anti-epileptic, anti-nausea. Between 2012 and 2013, there was research on CBDV as an epileptic drug, and soon thereafter, uk GW pharmaceutical company issued a patent on CBDV pharmacy that would allow GW pharmaceutical development to produce an antiepileptic drug based on CBDV. In 2013, university of canada university has also conducted intensive research on CBDV, and announced that CBDV may also be helpful in treating gastrointestinal problems such as nausea.
Cannabigerol, CBG, a non-psychoactive component of CBG, is present in the early stages of the cannabis growth cycle, so it is difficult to find a large amount of CBG, which means that its medical use can be obtained by cultivating cannabis. Medical value of CBG: can be used as antibiotic, and can be used for treating psoriasis, resisting tumor, relieving depression, and relieving pain. CBG was also tested against MRSA virus infection in 2008 as it was discovered in 1982 as it had antibacterial and fungicidal effects. In 1998, it was found by the korean researchers that CBG was effective in delaying the growth of oral cancer cells. CBG has also been reported in journal of pharmacology in the United kingdom to have a mild anti-tumour effect in the treatment of prostate cancer cells. In 2006, Danru discovered the antidepressant effect of CBG for the first time in the experiment of mice.
THCV, the medical value of THCV: has anticonvulsive, weight reducing, and neuroprotective effects. Animal experiments conducted by researchers in burkholdham saxavir, uk have demonstrated that THCV has an anticonvulsant effect and a study paper published in the C4 laboratory, arizona, usa has shown that it has a metabolic reduction effect. In addition, researchers have reported that cannabis with high THCV levels may help reduce some short-term memory and speech dysfunction.
However, at present, only two CBG, CBDV, CBD and THCV can be prepared simultaneously, and conditions in the preparation process are different, so that when one or two components are prepared, other components are destroyed as waste materials together with Tetrahydrocannabinol (THC), which causes resource waste, and the process also has the risk of repeated investment. Therefore, it is objectively needed to develop a method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp, which has the advantages of simple process operation, high recovery rate, environmental friendliness, high investment benefit and realization of large-scale production.
Disclosure of Invention
In order to solve the problems in the background art, the invention aims to provide the method for simultaneously preparing the CBG, the CBDV, the CBD and the THCV from the industrial hemp, which has the advantages of simple process operation, high recovery rate, environmental friendliness, high investment benefit and realization of large-scale production.
The invention relates to a method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp, which comprises the following steps:
crushing raw materials: crushing industrial hemp flowers and leaves into flower and leaf powder, wherein the particle size of the flower and leaf powder is 10-40 meshes;
drying: baking the flower and leaf powder obtained by crushing in the step one, wherein the baking temperature is 100-130 ℃, and the baking is carried out until the weight loss is more than 7%;
③ leaching: feeding the flower and leaf powder baked in the second step and ethanol according to a solid-to-liquid ratio of 1: 8-12, wherein the mass concentration of the ethanol is 80-85%; then extracting at 18-28 ℃ for 1.5-4 h, concentrating under the conditions of pressure of 0.04-0.07 Mpa and temperature of 50-70 ℃ after extraction is finished until the specific gravity is 0.94-0.95, and then freezing the concentrated solution at-20-40 ℃ for 1-3 h;
fourthly, filtering: filtering the concentrated solution frozen in the third step, collecting filtrate, extracting the filtrate for 2-4 times by using normal hexane with the volume being 1-2 times that of the filtrate after filtering, collecting a normal hexane layer after extraction, and recovering the solvent to obtain a hemp extract;
molecular distillation: and (4) carrying out three times of molecular distillation on the hemp extract prepared in the step (iv), wherein the process conditions of the first time of molecular distillation are as follows: feeding the hemp extract at 60-120 ℃, distilling at 120-130 ℃, keeping the vacuum degree at 1-10 Pa, condensing at 50-130 ℃, and collecting a first molecular distillation light phase after distillation; the process conditions of the second molecular distillation are as follows: the feeding temperature of the first molecular distillation light phase is 60-120 ℃, the distillation temperature is 130-140 ℃, the vacuum degree is 1-10 Pa, the condensation temperature is 50-130 ℃, and the second molecular distillation light phase is collected after distillation; the technological conditions of the third molecular distillation are as follows: the feeding temperature of the second molecular distillation light phase is 60-120 ℃, the distillation temperature is 130-145 ℃, the vacuum degree is 1-10 Pa, the condensation temperature is 80-100 ℃, and the third molecular distillation light phase is collected after distillation and is rich in CBG, CBDV, CBD and THCV oil;
sixthly, chromatographic column separation: dissolving the CBG, CBDV, CBD and THCV oil obtained by distillation in the fifth step by using ethanol with the mass concentration of 60%, then carrying out wet loading on the oil for chromatographic column separation, wherein the loading amount is 1-3% of the volume of the separation material in the chromatographic column, then sequentially eluting the separation material of the chromatographic column by using ethanol with the mass concentration of 60%, ethanol with the mass concentration of 62%, ethanol with the mass concentration of 65-70%, ethanol with the mass concentration of 75% and ethanol with the mass concentration of 75-80%, then eluting the chromatographic column by using ethanol with the mass concentration of 95% for next separation, respectively collecting the eluates after the ethanol with the mass concentration of 60%, ethanol with the mass concentration of 62%, ethanol with the mass concentration of 65-70% and ethanol with the mass concentration of 75% after the elution is finished, and respectively concentrating the eluates to obtain a CBG crystal, a CBDV crystal, a CBD crystal and;
and (b) recrystallizing: dissolving the CBG crystal, the CBDV crystal, the CBD crystal and the THCV oil respectively with ethanol, then recrystallizing at the temperature of-5 to-10 ℃, washing the separated crystals respectively with water, and drying to obtain the finished products of the CBG crystal, the CBDV crystal, the CBD crystal and the THCV crystal.
Further, in the third step, a filter with 500-600 meshes is adopted for filtering.
Further, in the step (sixthly), the separation material in the chromatographic column is a silica gel material or a macroporous adsorption resin material, and preferably, the particle size of the silica gel material or the macroporous adsorption resin material is 200-400 meshes.
Further, in the step sixthly, the amount of ethanol with a mass concentration of 60% is 2 column volumes, the amount of ethanol with a mass concentration of 62% is 2 column volumes, the amount of ethanol with a mass concentration of 65-70% is 2 column volumes, the amount of ethanol with a mass concentration of 75-80% is 3 column volumes, and the amount of ethanol with a mass concentration of 95% is 2 column volumes.
Further, in the step (viii), the mass concentration of the ethanol is 80 to 90%.
The raw material and reagent used in the invention are cheap and easy to obtain, the cost is low, the adopted operation and method are simple and easy to advance, the requirement on personnel is low, the solvent usage amount is small, the equipment requirement is not high, and the used solvent is mostly ethanol and water, thereby not only reducing the influence on environment and operators and the condition of solvent residue in the product, but also ensuring that the content of the target product in the obtained product is very high, for example, the purity of CBD after recrystallization can reach more than 99.7 percent, the purity of CBDV can reach more than 98 percent, the purity of CBG can reach more than 95 percent, the purity of THCV can reach more than 96.2 percent, meanwhile, the process method can also thoroughly remove and destroy the psychotoxic component THC in the hemp, and the product safety is high. The method solves the problems of the prior art, is more environment-friendly, has higher recovery rate of CBG, CBDV, CBD and THCV, has high investment benefit, and can realize large-scale production.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to be limiting in any way, and any modifications or alterations based on the teachings of the present invention are intended to fall within the scope of the present invention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains, as the following abbreviations and their corresponding materials appear in the present invention: CBDV is cannabidivarin, CBD is cannabidiol, CBG is cannabigerol, THCV is tetrahydrocannabivarin, and THC is tetrahydrocannabinol.
Example 1:
the method for simultaneously preparing CBG, CBDV, CBD, THCV from industrial hemp described in example 1 includes the following steps:
crushing raw materials: crushing industrial hemp flowers and leaves into flower and leaf powder, wherein the granularity of the flower and leaf powder is 40 meshes;
drying: baking the flower and leaf powder obtained by crushing in the step I at the baking temperature of 130 ℃ until the weight loss is more than 7%;
③ leaching: feeding the flower and leaf powder roasted in the second step and ethanol according to the solid-to-liquid ratio of 1:12, wherein the mass concentration of the ethanol is 80%; extracting at 18 deg.C for 1.5 hr, concentrating under 0.04Mpa at 50 deg.C until the specific gravity is 0.94, and freezing at-20 deg.C for 1 hr;
fourthly, filtering: filtering the concentrated solution frozen in the third step by using a 500-mesh filter, collecting filtrate, extracting the filtrate for 2 times by using normal hexane with the volume being 1 time that of the filtrate after filtering, collecting a normal hexane layer after extraction, and recovering the solvent to obtain a hemp extract;
molecular distillation: and (4) carrying out three times of molecular distillation on the hemp extract prepared in the step (iv), wherein the process conditions of the first time of molecular distillation are as follows: feeding hemp extract at 60 deg.C, distilling at 120 deg.C under 1Pa, condensing at 50 deg.C, and collecting the first molecular distillation light phase; the process conditions of the second molecular distillation are as follows: the feeding temperature of the first molecular distillation light phase is 60 ℃, the distillation temperature is 130 ℃, the vacuum degree is 1Pa, the condensation temperature is 50 ℃, and the second molecular distillation light phase is collected after distillation; the technological conditions of the third molecular distillation are as follows: the feeding temperature of the second molecular distillation light phase is 60 ℃, the distillation temperature is 130 ℃, the vacuum degree is 1Pa, the condensation temperature is 80 ℃, and the third molecular distillation light phase is collected after distillation and is rich in CBG, CBDV, CBD and THCV oil;
sixthly, chromatographic column separation: dissolving the CBG, CBDV, CBD and THCV oil obtained by distillation in the fifth step by using ethanol with the mass concentration of 60%, then carrying out wet loading on the oil to carry out chromatographic column separation, wherein the loading amount is 1% of the volume of the separation material in the chromatographic column, the separation material in the chromatographic column is a silica gel material, the granularity of the silica gel material is 200 meshes, then sequentially eluting the separation material of the chromatographic column by using ethanol with the mass concentration of 60%, ethanol with the mass concentration of 62%, ethanol with the mass concentration of 65%, ethanol with the mass concentration of 75% and ethanol with the mass concentration of 76%, and then eluting the chromatographic column by using ethanol with the mass concentration of 95% for next separation, wherein the ethanol with the mass concentration of 60% is 2 column volumes, the ethanol with the mass concentration of 62% is 2 column volumes, the ethanol with the mass concentration of 65% is 2 column volumes, the ethanol with the mass concentration of 75% is 2 column volumes, and the ethanol with the mass concentration of 756% is 3 column volumes, the using amount of ethanol with the mass concentration of 95% is 2 column volumes, after elution is finished, eluents with the mass concentrations of 60% ethanol, 62% ethanol, 65% and 76% ethanol after separation are respectively collected, and then the eluents are respectively concentrated, so that CBG crystals, CBDV crystals, CBD crystals and THCV crystals can be respectively obtained;
and (b) recrystallizing: dissolving the CBG crystal, the CBDV crystal, the CBD crystal and the THCV oil respectively by using ethanol, putting the mass concentration of the ethanol at 80 percent under the temperature condition of minus 5 ℃ for recrystallization, washing the precipitated crystals respectively by using water, and drying to obtain finished products of the CBG crystal, the CBDV crystal, the CBD crystal and the THCV crystal.
In the embodiment 1, the raw material and reagents used are cheap and easy to obtain, the cost is low, the adopted operation and method are simple and easy to advance, the requirement on personnel is low, the usage amount of the solvent is small, the requirement on equipment is not high, and most of the used solvent is ethanol and water, so that the influence on the environment and the operators and the condition of solvent residue in the product are reduced, the content of the target product in the obtained product is very high, 10kg of flower leaf powder is fed through HPLC (high performance liquid chromatography), the purity of CBD after recrystallization is 99.72%, and the yield is 52.3%; the purity of CBDV is 98.63%, and the yield is 50.32%; the purity of CBG is 96.42 percent, and the yield is 51.2 percent; the THCV has the purity of 96.57 percent and the yield of 49.67 percent, and the determination results show that the purity and the yield of each product prepared by the method are high, the yield is high, and the large-scale production can be realized.
Example 2:
the method for simultaneously preparing CBG, CBDV, CBD, THCV from industrial hemp described in example 2 includes the following steps:
crushing raw materials: crushing industrial hemp flowers and leaves into flower and leaf powder, wherein the granularity of the flower and leaf powder is 25 meshes;
drying: baking the flower and leaf powder obtained by crushing in the step I at the baking temperature of 120 ℃ until the weight loss is more than 7%;
③ leaching: feeding the flower and leaf powder roasted in the step II and ethanol according to the solid-to-liquid ratio of 1:10, wherein the mass concentration of the ethanol is 82.5%; extracting at 25 deg.C for 13 hr, concentrating under 0.06Mpa at 60 deg.C until the specific gravity is 0.945, and freezing at-30 deg.C for 2 hr;
fourthly, filtering: filtering the concentrated solution frozen in the third step by using a 550-mesh filter, collecting filtrate, extracting the filtrate for 3 times by using normal hexane with the volume 1.5 times that of the filtrate after filtering, collecting a normal hexane layer after extraction, and recovering the solvent to obtain a hemp extract;
molecular distillation: and (4) carrying out three times of molecular distillation on the hemp extract prepared in the step (iv), wherein the process conditions of the first time of molecular distillation are as follows: feeding the hemp extract at 90 deg.C, distilling at 125 deg.C under 6Pa, condensing at 100 deg.C, and collecting the first molecular distillation light phase; the process conditions of the second molecular distillation are as follows: the feeding temperature of the first molecular distillation light phase is 90 ℃, the distillation temperature is 135 ℃, the vacuum degree is 7Pa, the condensation temperature is 100 ℃, and the second molecular distillation light phase is collected after distillation; the technological conditions of the third molecular distillation are as follows: the feeding temperature of the second molecular distillation light phase is 100 ℃, the distillation temperature is 140 ℃, the vacuum degree is 6Pa, the condensation temperature is 90 ℃, and the third molecular distillation light phase is collected after distillation and is rich in CBG, CBDV, CBD and THCV oil;
sixthly, chromatographic column separation: dissolving the CBG, CBDV, CBD and THCV oil obtained by distillation in the fifth step by using ethanol with the mass concentration of 60%, then carrying out wet loading on the oil to carry out chromatographic column separation, wherein the loading amount is 2% of the volume of the separation material in the chromatographic column, the separation material in the chromatographic column is a macroporous adsorption resin material, the granularity of the macroporous adsorption resin material is 300 meshes, then sequentially eluting the separation material of the chromatographic column by using ethanol with the mass concentration of 60%, ethanol with the mass concentration of 62%, ethanol with the mass concentration of 68%, ethanol with the mass concentration of 75% and ethanol with the mass concentration of 77%, and then eluting the chromatographic column by using ethanol with the mass concentration of 95% for next separation, wherein the ethanol with the mass concentration of 60% is 2 column volumes, the ethanol with the mass concentration of 62% is 2 column volumes, the ethanol with the mass concentration of 68% is 2 column volumes, the ethanol with the mass concentration of 75% is 2 column volumes, and the ethanol with the mass concentration of 77% is 3 column volumes, the using amount of ethanol with the mass concentration of 95% is 2 column volumes, after elution is finished, eluents with the mass concentrations of 60% ethanol, 62% ethanol, 68% ethanol and 75% ethanol after separation are respectively collected, and then the eluents are respectively concentrated to respectively obtain CBG crystals, CBDV crystals, CBD crystals and THCV crystals;
and (b) recrystallizing: dissolving the CBG crystal, the CBDV crystal, the CBD crystal and the THCV oil respectively by using ethanol, putting the mass concentration of the ethanol at 85 percent under the temperature condition of 8 ℃ below zero for recrystallization, washing the precipitated crystals respectively by using water, and drying to obtain finished products of the CBG crystal, the CBDV crystal, the CBD crystal and the THCV crystal.
In the embodiment 2, the raw material and reagents used are cheap and easy to obtain, the cost is low, the adopted operation and method are simple and easy to advance, the requirement on personnel is low, the usage amount of the solvent is small, the requirement on equipment is not high, and most of the used solvent is ethanol and water, so that the influence on the environment and the operators and the condition of solvent residue in the product are reduced, the content of the target product in the obtained product is very high, 10kg of flower leaf powder is fed through HPLC (high performance liquid chromatography), the purity of CBD after recrystallization is 99.84%, and the yield is 53.6%; the purity of CBDV is 99.1%, and the yield is 53.1%; the purity of CBG is 97.54%, and the yield is 49.67%; the THCV has the purity of 96.84 percent and the yield of 50.71 percent, and the determination results show that the purity and the yield of each product prepared by the method are high, the yield is high, and the large-scale production can be realized.
Example 3:
the method for simultaneously preparing CBG, CBDV, CBD, THCV from industrial hemp described in this example 3 includes the following steps:
crushing raw materials: crushing industrial hemp flowers and leaves into flower and leaf powder, wherein the granularity of the flower and leaf powder is 40 meshes;
drying: baking the flower and leaf powder obtained by crushing in the step I at the baking temperature of 130 ℃ until the weight loss is more than 7%;
③ leaching: feeding the flower and leaf powder roasted in the second step and ethanol according to the solid-to-liquid ratio of 1:12, wherein the mass concentration of the ethanol is 85%; extracting at 28 deg.C for 4 hr, concentrating under 0.07Mpa at 70 deg.C until the specific gravity is 0.95, and freezing at-40 deg.C for 3 hr;
fourthly, filtering: filtering the concentrated solution frozen in the third step by using a 600-mesh filter, collecting filtrate, extracting the filtrate for 4 times by using n-hexane with the volume 2 times that of the filtrate after filtering, collecting an n-hexane layer after extraction, and recovering the solvent to obtain a hemp extract;
molecular distillation: and (4) carrying out three times of molecular distillation on the hemp extract prepared in the step (iv), wherein the process conditions of the first time of molecular distillation are as follows: feeding hemp extract at 120 deg.C, distilling at 130 deg.C under vacuum degree of 10Pa, condensing at 130 deg.C, and distilling to collect the first molecular distillation light phase; the process conditions of the second molecular distillation are as follows: the feeding temperature of the first molecular distillation light phase is 120 ℃, the distillation temperature is 140 ℃, the vacuum degree is 10Pa, the condensation temperature is 130 ℃, and the second molecular distillation light phase is collected after distillation; the technological conditions of the third molecular distillation are as follows: the feeding temperature of the second molecular distillation light phase is 120 ℃, the distillation temperature is 145 ℃, the vacuum degree is 10Pa, the condensation temperature is 100 ℃, and the third molecular distillation light phase is collected after distillation and is rich in CBG, CBDV, CBD and THCV oil;
sixthly, chromatographic column separation: dissolving the CBG, CBDV, CBD and THCV oil obtained by distillation in the fifth step by using ethanol with the mass concentration of 60%, then carrying out wet loading on the oil to carry out chromatographic column separation, wherein the loading amount is 3% of the volume of the separation material in the chromatographic column, the separation material in the chromatographic column is a silica gel material, the granularity of the silica gel material is 400 meshes, then sequentially eluting the separation material of the chromatographic column by using ethanol with the mass concentration of 60%, ethanol with the mass concentration of 62%, ethanol with the mass concentration of 70%, ethanol with the mass concentration of 75% and ethanol with the mass concentration of 80%, and then eluting the chromatographic column by using ethanol with the mass concentration of 95% for next separation, wherein the ethanol with the mass concentration of 60% is 2 column volumes, the ethanol with the mass concentration of 62% is 2 column volumes, the ethanol with the mass concentration of 70% is 2 column volumes, the ethanol with the mass concentration of 75% is 2 column volumes, and the ethanol with the mass concentration of 80% is 3 column volumes, the using amount of ethanol with the mass concentration of 95% is 2 column volumes, after elution is finished, eluents with the mass concentrations of 60% ethanol, 62% ethanol, 70% ethanol and 75% ethanol after separation are respectively collected, and then the eluents are respectively concentrated to respectively obtain CBG crystals, CBDV crystals, CBD crystals and THCV crystals;
and (b) recrystallizing: dissolving the CBG crystal, the CBDV crystal, the CBD crystal and the THCV oil respectively by using ethanol, then recrystallizing the mixture at the temperature of minus 10 ℃ after the mass concentration of the ethanol is 90 percent, washing the separated crystals respectively by using water, and then drying the crystals to obtain finished products of the CBG crystal, the CBDV crystal, the CBD crystal and the THCV crystal.
In this embodiment 3, the raw material and reagents used in the method are cheap and easily available, the cost is low, the adopted operation and method are simple and easy to advance, the requirement on personnel is low, the usage amount of the solvent is small, the requirement on equipment is not high, and most of the used solvent is ethanol and water, so that the influence on the environment and the operators and the condition of solvent residue in the product are reduced, the content of the target product in the obtained product is very high, 10kg of flower and leaf powder is fed through HPLC determination, the purity of CBD after recrystallization is 99.83%, and the yield is 51.12%; the purity of CBDV is 98.94%, and the yield is 49.68%; the purity of CBG is 97.12 percent, and the yield is 48.62 percent; the THCV has the purity of 97.25 percent and the yield of 4.39 percent, and the determination results show that the purity and the yield of each product prepared by the method are high, the yield is high, and the large-scale production can be realized.
Claims (6)
1. A method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp, which is characterized by comprising the following steps:
crushing raw materials: crushing industrial hemp flowers and leaves into flower and leaf powder, wherein the particle size of the flower and leaf powder is 10-40 meshes;
drying: baking the flower and leaf powder obtained by crushing in the step one, wherein the baking temperature is 100-130 ℃, and the baking is carried out until the weight loss is more than 7%;
③ leaching: feeding the flower and leaf powder baked in the second step and ethanol according to a solid-to-liquid ratio of 1: 8-12, wherein the mass concentration of the ethanol is 80-85%; then extracting at 18-28 ℃ for 1.5-4 h, concentrating under the conditions of pressure of 0.04-0.07 Mpa and temperature of 50-70 ℃ after extraction is finished until the specific gravity is 0.94-0.95, and then freezing the concentrated solution at-20-40 ℃ for 1-3 h;
fourthly, filtering: filtering the concentrated solution frozen in the third step, collecting filtrate, extracting the filtrate for 2-4 times by using normal hexane with the volume being 1-2 times that of the filtrate after filtering, collecting a normal hexane layer after extraction, and recovering the solvent to obtain a hemp extract;
molecular distillation: and (4) carrying out three times of molecular distillation on the hemp extract prepared in the step (iv), wherein the process conditions of the first time of molecular distillation are as follows: feeding the hemp extract at 60-120 ℃, distilling at 120-130 ℃, keeping the vacuum degree at 1-10 Pa, condensing at 50-130 ℃, and collecting a first molecular distillation light phase after distillation; the process conditions of the second molecular distillation are as follows: the feeding temperature of the first molecular distillation light phase is 60-120 ℃, the distillation temperature is 130-140 ℃, the vacuum degree is 1-10 Pa, the condensation temperature is 50-130 ℃, and the second molecular distillation light phase is collected after distillation; the technological conditions of the third molecular distillation are as follows: the feeding temperature of the second molecular distillation light phase is 60-120 ℃, the distillation temperature is 130-145 ℃, the vacuum degree is 1-10 Pa, the condensation temperature is 80-100 ℃, and the third molecular distillation light phase is collected after distillation and is rich in CBG, CBDV, CBD and THCV oil;
sixthly, chromatographic column separation: dissolving the CBG, CBDV, CBD and THCV oil obtained by distillation in the fifth step by using ethanol with the mass concentration of 60%, then carrying out wet loading on the oil for chromatographic column separation, wherein the loading amount is 1-3% of the volume of the separation material in the chromatographic column, then sequentially eluting the separation material of the chromatographic column by using ethanol with the mass concentration of 60%, ethanol with the mass concentration of 62%, ethanol with the mass concentration of 65-70%, ethanol with the mass concentration of 75% and ethanol with the mass concentration of 75-80%, then eluting the chromatographic column by using ethanol with the mass concentration of 95% for next separation, respectively collecting the eluates after the ethanol with the mass concentration of 60%, ethanol with the mass concentration of 62%, ethanol with the mass concentration of 65-70% and ethanol with the mass concentration of 75% after the elution is finished, and respectively concentrating the eluates to obtain a CBG crystal, a CBDV crystal, a CBD crystal and;
and (b) recrystallizing: dissolving the CBG crystal, the CBDV crystal, the CBD crystal and the THCV oil respectively with ethanol, then recrystallizing at the temperature of-5 to-10 ℃, washing the separated crystals respectively with water, and drying to obtain the finished products of the CBG crystal, the CBDV crystal, the CBD crystal and the THCV crystal.
2. The method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp according to claim 1, wherein in the third step, the filter with 500-600 meshes is adopted.
3. The method for simultaneously preparing CBG, CBDV, CBD, THCV from industrial hemp according to claim 1, wherein in step (sixty), the separation material in the chromatographic column is silica gel material or macroporous absorption resin material.
4. The method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp according to claim 3, wherein the particle size of the silica gel material or the macroporous absorption resin material is 200-400 meshes.
5. The method for simultaneously preparing CBG, CBDV, CBD, THCV from industrial hemp according to claim 1, wherein in the step (c), the amount of ethanol with mass concentration of 60% is 2 column volumes, the amount of ethanol with mass concentration of 62% is 2 column volumes, the amount of ethanol with mass concentration of 65-70% is 2 column volumes, the amount of ethanol with mass concentration of 75-80% is 3 column volumes, and the amount of ethanol with mass concentration of 95% is 2 column volumes.
6. The method for simultaneously preparing CBG, CBDV, CBD, THCV from industrial hemp according to claim 1, wherein the mass concentration of ethanol in step (b) is 80-90%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010852203.9A CN112062658A (en) | 2020-08-21 | 2020-08-21 | Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010852203.9A CN112062658A (en) | 2020-08-21 | 2020-08-21 | Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112062658A true CN112062658A (en) | 2020-12-11 |
Family
ID=73660639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010852203.9A Pending CN112062658A (en) | 2020-08-21 | 2020-08-21 | Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112062658A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112939742A (en) * | 2021-04-14 | 2021-06-11 | 龙麻(上海)医药研发有限责任公司 | Method for extracting and purifying cannabinoid |
| CN115385780A (en) * | 2022-08-26 | 2022-11-25 | 晨光生物科技集团股份有限公司 | Sub-cannabidiol crystal polymorphic substance as well as preparation method and application thereof |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106278828A (en) * | 2016-08-16 | 2017-01-04 | 云南汉素生物科技有限公司 | A kind of method extracting cannabidiol from industrial hemp floral leaf |
| CN109568389A (en) * | 2017-09-29 | 2019-04-05 | 汉义生物科技（北京）有限公司 | A kind of preparation method of high-purity cannabinoids extract |
| CN109574810A (en) * | 2017-09-29 | 2019-04-05 | 汉义生物科技（北京）有限公司 | Method that is a kind of while extracting CBD and CBDV |
| CN110066216A (en) * | 2019-04-30 | 2019-07-30 | 栾云鹏 | A kind of extraction separation method of cannabidiol |
| CN110317126A (en) * | 2019-07-02 | 2019-10-11 | 黑龙江康源生物科技有限公司 | A kind of method and system for extracting cannabidiol in industrial hemp with microwave-assisted Subcritical Water Extraction technology |
| CN110330409A (en) * | 2019-07-24 | 2019-10-15 | 汉义生物科技（北京）有限公司 | A kind of preparation method of industrial hemp extract |
| CN110423187A (en) * | 2019-08-22 | 2019-11-08 | 哈尔滨工业大学 | A kind of tunnel ultrasound and thermo-circulation distillation combination extraction cannabidiol (CBD) method |
| CN110437041A (en) * | 2019-08-22 | 2019-11-12 | 哈尔滨工业大学 | It is a kind of using industrial hemp as the preparation method of the cannabidiol of raw material |
| CN110467521A (en) * | 2019-08-22 | 2019-11-19 | 哈尔滨工业大学 | It is a kind of using industrial hemp as cannabidiol (CBD) isolation and purification method of raw material |
| CN110511119A (en) * | 2019-08-13 | 2019-11-29 | 云南飞久逍科技有限公司 | A kind of extracting method of cannabidiol |
| CN110642679A (en) * | 2019-08-27 | 2020-01-03 | 桂林莱茵生物科技股份有限公司 | Method for preparing cannabidiol and coproducing cannabis full spectrum oil |
| CN110878010A (en) * | 2019-12-16 | 2020-03-13 | 云南绿新生物药业有限公司 | Extraction and separation method of cannabigerol |
| CN111470953A (en) * | 2020-04-24 | 2020-07-31 | 西安蓝晓科技新材料股份有限公司 | Method for extracting and separating high-purity cannabidiol from low-content industrial cannabis sativa leaves |
-
2020
- 2020-08-21 CN CN202010852203.9A patent/CN112062658A/en active Pending
Patent Citations (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106278828A (en) * | 2016-08-16 | 2017-01-04 | 云南汉素生物科技有限公司 | A kind of method extracting cannabidiol from industrial hemp floral leaf |
| CN106831353A (en) * | 2016-08-16 | 2017-06-13 | 云南汉素生物科技有限公司 | A kind of method that cannabidiol is extracted from hemp |
| CN109568389A (en) * | 2017-09-29 | 2019-04-05 | 汉义生物科技（北京）有限公司 | A kind of preparation method of high-purity cannabinoids extract |
| CN109574810A (en) * | 2017-09-29 | 2019-04-05 | 汉义生物科技（北京）有限公司 | Method that is a kind of while extracting CBD and CBDV |
| CN110066216A (en) * | 2019-04-30 | 2019-07-30 | 栾云鹏 | A kind of extraction separation method of cannabidiol |
| CN110317126A (en) * | 2019-07-02 | 2019-10-11 | 黑龙江康源生物科技有限公司 | A kind of method and system for extracting cannabidiol in industrial hemp with microwave-assisted Subcritical Water Extraction technology |
| CN110330409A (en) * | 2019-07-24 | 2019-10-15 | 汉义生物科技（北京）有限公司 | A kind of preparation method of industrial hemp extract |
| CN110511119A (en) * | 2019-08-13 | 2019-11-29 | 云南飞久逍科技有限公司 | A kind of extracting method of cannabidiol |
| CN110423187A (en) * | 2019-08-22 | 2019-11-08 | 哈尔滨工业大学 | A kind of tunnel ultrasound and thermo-circulation distillation combination extraction cannabidiol (CBD) method |
| CN110437041A (en) * | 2019-08-22 | 2019-11-12 | 哈尔滨工业大学 | It is a kind of using industrial hemp as the preparation method of the cannabidiol of raw material |
| CN110467521A (en) * | 2019-08-22 | 2019-11-19 | 哈尔滨工业大学 | It is a kind of using industrial hemp as cannabidiol (CBD) isolation and purification method of raw material |
| CN110642679A (en) * | 2019-08-27 | 2020-01-03 | 桂林莱茵生物科技股份有限公司 | Method for preparing cannabidiol and coproducing cannabis full spectrum oil |
| CN110878010A (en) * | 2019-12-16 | 2020-03-13 | 云南绿新生物药业有限公司 | Extraction and separation method of cannabigerol |
| CN111470953A (en) * | 2020-04-24 | 2020-07-31 | 西安蓝晓科技新材料股份有限公司 | Method for extracting and separating high-purity cannabidiol from low-content industrial cannabis sativa leaves |
Non-Patent Citations (1)
| Title |
|---|
| 吴雪辉: "茶油加工与综合利用技术", 广东科学技术出版社, pages: 158 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112939742A (en) * | 2021-04-14 | 2021-06-11 | 龙麻(上海)医药研发有限责任公司 | Method for extracting and purifying cannabinoid |
| CN112939742B (en) * | 2021-04-14 | 2023-07-28 | 龙麻(上海)医药研发有限责任公司 | Extraction and purification method of cannabinoid |
| CN115385780A (en) * | 2022-08-26 | 2022-11-25 | 晨光生物科技集团股份有限公司 | Sub-cannabidiol crystal polymorphic substance as well as preparation method and application thereof |
| CN115385780B (en) * | 2022-08-26 | 2024-02-27 | 晨光生物科技集团股份有限公司 | Secondary cannabidiol crystal polymorph and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109574810B (en) | Method for simultaneously extracting CBD and CBDV | |
| CN110642679B (en) | Method for preparing cannabidiol and coproducing cannabis full spectrum oil | |
| CN107011125A (en) | A kind of method for being enriched with cannabidiol | |
| CN110283048A (en) | The preparation method of cannabidiol crystal | |
| CN1974527B (en) | Process of preparing high purity chlorogenic acid and flavonid with eucommia leaf | |
| CN112062658A (en) | Method for simultaneously preparing CBG, CBDV, CBD and THCV from industrial hemp | |
| CN111978157A (en) | Method for extracting and purifying cannabidiol from industrial cannabis sativa | |
| WO2020165902A1 (en) | Method for synthesis of cannabis products | |
| CN103992224B (en) | A kind of method from extracting chlorogenic acid from Eucommia leaves | |
| CN111099970A (en) | Method for industrially extracting cannabidiol from industrial cannabis sativa | |
| CN102442916A (en) | Method for extracting natural activated products from orange drops | |
| CN110423187A (en) | A kind of tunnel ultrasound and thermo-circulation distillation combination extraction cannabidiol (CBD) method | |
| CN112010738B (en) | Industrial method for producing cannabinoid compound by utilizing chromatographic separation | |
| CN112661613A (en) | Method for industrial clean production of cannabidiol CBD broad-spectrum oil | |
| CN110922376A (en) | Method for producing high-purity tetrahydrocannabinol by chromatography | |
| CN101982471B (en) | Technological process for extracting aucubin from fruits of eucommia ulmoides oliver | |
| CN102718774B (en) | Method for preparing artemisinin | |
| CN112661612A (en) | Method for large-scale preparation of high-purity CBD through post-decarboxylation and supercritical extraction | |
| CN111848358A (en) | Method for preparing high-purity cannabidiol by combining macroporous resin enrichment with dynamic axial compression column system | |
| CN112939742B (en) | Extraction and purification method of cannabinoid | |
| CN111848362A (en) | Method for preparing high-purity cannabidiol by combining ultrasonic extraction with dynamic axial compression column system | |
| CN104086467A (en) | Method for preparing sulforaphene by adopting solvent extraction method and molecular distillation method | |
| CN101311186A (en) | Process for preparing tripterine | |
| CN103408402A (en) | Method for extracting high-purity resveratrol from grape seed | |
| CN102432419B (en) | Method for extracting and separating beta-elemene from Eupatorium adenophorum |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20201211 |
|
| RJ01 | Rejection of invention patent application after publication |