CN116120159A - Extraction method of cinnamaldehyde - Google Patents
Extraction method of cinnamaldehyde Download PDFInfo
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- CN116120159A CN116120159A CN202310199112.3A CN202310199112A CN116120159A CN 116120159 A CN116120159 A CN 116120159A CN 202310199112 A CN202310199112 A CN 202310199112A CN 116120159 A CN116120159 A CN 116120159A
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- cinnamaldehyde
- chlorophyll
- volatilize
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- citrate
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- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 title claims abstract description 100
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 title claims abstract description 99
- 229940117916 cinnamic aldehyde Drugs 0.000 title claims abstract description 99
- 238000000605 extraction Methods 0.000 title claims abstract description 57
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 42
- 239000010630 cinnamon oil Substances 0.000 claims abstract description 24
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 24
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims abstract description 22
- 239000004698 Polyethylene Substances 0.000 claims abstract description 21
- 229920001519 homopolymer Polymers 0.000 claims abstract description 21
- 229920000573 polyethylene Polymers 0.000 claims abstract description 21
- 241000723347 Cinnamomum Species 0.000 claims abstract description 19
- 235000017803 cinnamon Nutrition 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 19
- 230000003647 oxidation Effects 0.000 claims abstract description 18
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 229930002875 chlorophyll Natural products 0.000 claims abstract description 15
- 235000019804 chlorophyll Nutrition 0.000 claims abstract description 15
- 239000000843 powder Substances 0.000 claims abstract description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 5
- 238000002791 soaking Methods 0.000 claims abstract description 5
- 239000003921 oil Substances 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 239000011261 inert gas Substances 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 239000003963 antioxidant agent Substances 0.000 claims description 18
- 230000003078 antioxidant effect Effects 0.000 claims description 18
- 239000002310 Isopropyl citrate Substances 0.000 claims description 9
- SKHXHUZZFVMERR-UHFFFAOYSA-L isopropyl citrate Chemical group CC(C)OC(=O)CC(O)(C([O-])=O)CC([O-])=O SKHXHUZZFVMERR-UHFFFAOYSA-L 0.000 claims description 9
- 235000019300 isopropyl citrate Nutrition 0.000 claims description 9
- 229930002865 chlorophyll c2 Natural products 0.000 claims description 8
- QDRBYWCRXZZVLY-KXVZLLGWSA-L chlorophyll c2 Chemical compound N12[Mg]N3C4=C5C(C(=O)OC)C(=O)C4=C(C)C3=CC(C(=C3C)C=C)=N\C3=C/C2=C(C=C)C(C)=C1\C=C/1C(C)=C(\C=C\C(O)=O)C5=N\1 QDRBYWCRXZZVLY-KXVZLLGWSA-L 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- 230000001976 improved effect Effects 0.000 abstract description 12
- 238000006482 condensation reaction Methods 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 8
- 238000011282 treatment Methods 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 21
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 10
- 230000003064 anti-oxidating effect Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 229930002868 chlorophyll a Natural products 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- -1 citric acid ester Chemical class 0.000 description 3
- 238000004925 denaturation Methods 0.000 description 3
- 230000036425 denaturation Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VZWGRQBCURJOMT-UHFFFAOYSA-N Dodecyl acetate Chemical compound CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- KKVZAVRSVHUSPL-GQCTYLIASA-N Cassiastearoptene Chemical compound COC1=CC=CC=C1\C=C\C=O KKVZAVRSVHUSPL-GQCTYLIASA-N 0.000 description 1
- 244000037364 Cinnamomum aromaticum Species 0.000 description 1
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
- 235000021511 Cinnamomum cassia Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000218195 Lauraceae Species 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- KKVZAVRSVHUSPL-UHFFFAOYSA-N o-methoxycinnamic aldehyde Natural products COC1=CC=CC=C1C=CC=O KKVZAVRSVHUSPL-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008093 supporting effect Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/86—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/022—Refining
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/025—Recovery by solvent extraction
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/027—Recovery of volatiles by distillation or stripping
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention relates to the field of natural raw material extraction, in particular to a method for extracting cinnamaldehyde, which comprises the following steps: s1, soaking cinnamon leaf powder in a solvent, performing ultrasonic treatment, condensing steam generated in the ultrasonic treatment process, and separating oil from water to obtain cinnamon oil; s2, adding a difficult-to-volatilize oxidation-preventing treating agent into the cinnamon oil, mixing, and then introducing inert gas for rectification separation to obtain cinnamaldehyde; the mass ratio of the difficult-to-volatilize oxidation preventing treating agent to the cinnamon oil is (2-4) 100; the non-volatile oxidation preventing treating agent comprises citric acid, citrate, mercaptan-polyethylene glycol-mercaptan linear homopolymer and chlorophyll. The cinnamaldehyde extracted by the method is not easy to oxidize and undergo self-condensation reaction, and the cinnamaldehyde is not easy to lose efficacy or denature, so that the extraction rate and purity of the cinnamaldehyde are improved.
Description
Technical Field
The invention relates to the field of natural raw material extraction, in particular to a method for extracting cinnamaldehyde.
Background
Cinnamon (Cinnamomum cassia) belongs to Lauraceae plants, has the advantages of being spicy, sweet and hot in taste, and has the effects of tonifying fire, supporting yang, inducing fire, returning to origin, dispelling cold, relieving pain and the like, is a plant material for both medicine and food published by the ministry of health of China, and is rich in cinnamon oil in branches, leaves, flowers, fruits and barks. The cinnamon oil is an aromatic essential oil with complex components, wherein more than 50 components are identified, the main component is cinnamaldehyde, and the cinnamon oil also contains a small amount of o-methoxy cinnamaldehyde, benzaldehyde, coumarin, lauryl acetate and the like. The cinnamyl aldehyde has good fragrance-holding effect, can be used as a fragrance-mixing raw material in fragrance mixing to ensure that the fragrance of main perfume is more fragrant, has antibacterial effect, can be used as a natural food preservative, and can be widely applied to the aspects of perfume, pharmacy, daily chemicals, food processing and the like.
At present, the extraction of cinnamaldehyde from cinnamon mainly adopts steam distillation extraction, aqueous enzymatic extraction and supercritical CO 2 And (5) extracting. Because the extraction time of the cinnamaldehyde by steam distillation is long, the temperature is high, and the cinnamaldehyde is a heat-sensitive liquid and heated at high temperature for a long time, the cinnamaldehyde can be oxidized and undergo self-condensation reaction, and the cinnamaldehyde is easy to lose efficacy or denature, so that the extraction rate of the cinnamaldehyde is reduced. The water-enzyme method for extracting cinnamaldehyde needs to control the reaction temperature to achieve the optimal activity of enzyme, and has high cost. Supercritical CO 2 The extraction is carried out to extract the cinnamaldehyde, the equipment requirement is high, and the cost is high.
Therefore, there is a need to develop a method for extracting cinnamaldehyde with low cost and high extraction rate.
Disclosure of Invention
In order to improve the extraction rate of cinnamaldehyde, the application provides an extraction method of cinnamaldehyde.
In a first aspect, the present application provides a method for extracting cinnamaldehyde, which is implemented by adopting the following technical scheme:
the extraction method of the cinnamaldehyde comprises the following steps:
s1, soaking cinnamon leaf powder in a solvent, performing ultrasonic treatment, condensing steam generated in the ultrasonic treatment process, and separating oil from water to obtain cinnamon oil;
s2, adding a difficult-to-volatilize oxidation-preventing treating agent into the cinnamon oil, mixing, and then introducing inert gas for rectification separation to obtain cinnamaldehyde; the mass ratio of the difficult-to-volatilize oxidation preventing treating agent to the cinnamon oil is (2-4) 100; the non-volatile oxidation preventing treating agent comprises citric acid, citrate, mercaptan-polyethylene glycol-mercaptan linear homopolymer and chlorophyll.
By adopting the technical scheme, the difficult-to-volatilize anti-oxidation treatment agent consisting of citric acid, citric acid ester, mercaptan-polyethylene glycol-mercaptan linear homopolymer and chlorophyll is difficult to volatilize, and the purity of cinnamaldehyde cannot be reduced when the treatment agent is added into cinnamon oil, has better reducibility, and can inhibit the oxidation of the cinnamaldehyde and the self-condensation reaction, so that the extraction rate and purity of the cinnamaldehyde are improved.
Preferably, the mass ratio of the citric acid, the citrate, the mercaptan-polyethylene glycol-mercaptan linear homopolymer to the chlorophyll is 1 (2-3) (0.1-0.15) (0.03-0.05).
More preferably, the mass ratio of the citric acid, the citrate, the thiol-polyethylene glycol-thiol linear homopolymer and the chlorophyll is 1:2.5:0.15:0.04.
By adopting the technical scheme, the difficult-to-volatilize oxidation-preventing treating agent which is prepared by mixing citric acid, citric acid ester, mercaptan-polyethylene glycol-mercaptan linear homopolymer and chlorophyll according to the mass ratio of 1:2.5:0.15:0.04 can better inhibit the oxidation of cinnamaldehyde and the self-condensation reaction, and can improve the extraction rate and purity of the cinnamaldehyde.
Preferably, the citrate is isopropyl citrate.
By adopting the technical scheme, the isopropyl citrate contains free carboxyl, and has hydrogen bond interaction with-SH and-OH in the thiol-polyethylene glycol-thiol linear homopolymer, so that the reducibility of the thiol-polyethylene glycol-thiol linear homopolymer in the difficult-to-volatilize anti-oxidation treatment agent can be improved, and the oxidation of cinnamaldehyde can be better inhibited, so that the extraction rate and purity of the cinnamaldehyde are improved.
Preferably, the chlorophyll is chlorophyll c2.
By adopting the technical scheme, the chlorophyll c2 has more carbon-carbon unsaturated double bonds, improves the reducibility of the anti-oxidation treatment agent which is difficult to volatilize, reduces the invalidation or denaturation of the cinnamaldehyde, and further improves the extraction rate and purity of the cinnamaldehyde.
Preferably, the mass ratio of the difficult-to-volatilize anti-oxidation treatment agent to the cinnamon oil is 3:100.
Preferably, in the step S1, the power of the ultrasonic treatment is 80-100W, and the time of the ultrasonic treatment is 2-3h.
Preferably, the solvent is formed by mixing ethanol and ethyl acetate according to the mass ratio of (3-5): 1.
The extraction method of the cinnamaldehyde avoids the use of toxic reagents such as methanol, benzene and the like, has no residue of harmful solvents and is safer to use. And the solvent compounded by ethanol and ethyl acetate is beneficial to the dissolution of cinnamaldehyde in the cinnamon leaf powder, so that the extraction rate and concentration of the cinnamaldehyde in the cinnamon oil are improved.
Preferably, the particle size of the cinnamon leaf powder is 50-100 meshes.
The cinnamon leaf powder has smaller particle size, is beneficial to reducing the dosage of solvent, is beneficial to dissolving out active ingredients in the cinnamon leaves by subsequent ultrasonic treatment, and improves the content of the active ingredients in the cinnamon oil.
In summary, the present application has the following beneficial effects:
1. the application adopts the difficult-to-volatilize oxidation-resistant treating agent composed of citric acid, citric acid ester, mercaptan-polyethylene glycol-mercaptan linear homopolymer and chlorophyll, has difficult volatility, can not reduce the purity of cinnamaldehyde when being added into cinnamon oil, has better reducibility, can inhibit the cinnamaldehyde from being oxidized and undergoing self-condensation reaction, thereby improving the extraction rate and purity of the cinnamaldehyde.
2. The application preferably adopts isopropyl citrate containing free carboxyl, has hydrogen bond interaction with-SH and-OH in the thiol-polyethylene glycol-thiol linear homopolymer, and can improve the reducibility of the thiol-polyethylene glycol-thiol linear homopolymer in the difficult-to-volatilize oxidation preventing treatment agent, thereby improving the extraction rate and purity of cinnamaldehyde.
3. Chlorophyll c2 is preferably adopted, carbon-carbon unsaturated double bonds are more, the reducibility of the volatilizable anti-oxidation treatment agent is improved, the invalidation or denaturation of cinnamaldehyde is reduced, and the extraction rate and purity of the cinnamaldehyde are further improved.
4. The solvent compounded by the ethanol and the ethyl acetate avoids the use of toxic reagents such as methanol, benzene and the like, has no residue of harmful solvents, is safer to use, and is favorable for dissolving out the cinnamaldehyde in the cinnamon leaf powder, thereby improving the extraction rate and concentration of the cinnamaldehyde in the cinnamon oil.
Detailed Description
The present application is described in further detail below with reference to examples.
Preparation example
Preparation examples 1 to 7 provide a hardly volatile oxidation-preventing treatment agent, and preparation example 1 is given as an example.
The preparation method of the difficult-to-volatilize oxidation-preventing treating agent provided in preparation example 1 comprises the following preparation steps:
100g of citric acid, 200g of tri-n-butyl citrate, 10g of thiol-polyethylene glycol-thiol linear homopolymer (purchased from Ontario novel carbon materials, changzhou Co., ltd.) and 3g of chlorophyll a are uniformly mixed to obtain the anti-oxidation treatment agent which is difficult to volatilize.
Preparation examples 2 to 5 differ from preparation example 1 only in that: the quality of the raw materials for preparing the anti-oxidation treatment agent which is difficult to volatilize is different, and the quality is shown in a table 1.
TABLE 1 preparation examples 1-5 quality/g of raw materials for preparing the hardly volatile antioxidant treatment agent
Preparation 6 differs from preparation 5 only in that: the equal mass of tri-n-butyl citrate is replaced by isopropyl citrate.
Preparation 7 differs from preparation 6 only in that: chlorophyll a and other mass is replaced by chlorophyll c2.
Preparation of comparative example
Comparative example 1 was prepared, differing from preparation example 1 only in that: the linear thiol-polyethylene glycol-thiol homopolymer is replaced by chlorophyll a.
Comparative example 2 was prepared, differing from preparation example 1 only in that: chlorophyll a is replaced by linear thiol-polyethylene glycol-thiol homopolymer.
Preparation comparative example 3 provides a hardly volatile treatment agent, which is prepared by the following steps:
100g of citric acid and 200g of tri-n-butyl citrate are uniformly mixed to obtain the treatment agent which is difficult to volatilize.
Examples
Examples 1 to 14 provide a method for extracting cinnamaldehyde, and the following will take example 1 as an example.
The extraction method of cinnamaldehyde provided in the embodiment 1 comprises the following steps:
s11, taking 0.1kg of cinnamon leaf powder with the particle size of 50 meshes, placing the cinnamon leaf powder into 2kg of a solvent formed by mixing ethanol and ethyl acetate according to the mass ratio of 3:1, and soaking for 5 hours to obtain a raw material liquid;
s12, putting the raw material liquid generated in the step S11 into a reaction kettle of an ultrasonic processor, adding reclaimed water of a water collecting tank into the reaction kettle by a pump, moving back and closing an upper end socket of the reaction kettle, connecting a steam outlet pipe, introducing steam into the reaction kettle from a steam inlet pipe at the bottom end of the reaction kettle for heating, setting the power of ultrasonic treatment to be 80W, the time of ultrasonic treatment to be 3h, boiling the cinnamon raw material by the steam in the ultrasonic treatment process to obtain mixed steam, and conveying the mixed steam to a secondary condenser through a steam outlet pipe at the top of the reaction kettle for secondary condensation to obtain condensate;
s13, adding condensate generated in the step S12 into a three-stage oil-water separator to perform three-stage oil-water separation, and collecting cinnamon oil through an oil collecting tank;
s2, adding a difficult-to-volatilize antioxidant treatment agent (derived from preparation example 1) into the cinnamon oil obtained in the step S13, uniformly mixing, adding nitrogen into a rectifying tower at a flow rate of 0.2L/min for 10min, and controlling the rectifying temperature: and (3) separating at 160 ℃ in the tower kettle and with the vacuum degree of a rectifying tower of 6.65kPa to obtain the cinnamaldehyde product.
The cinnamaldehyde product obtained in example 1 was examined to have an extraction rate of 2.68% and a purity of 98.2%.
Examples 2-3 differ from example 1 only in that: the amounts of the nonvolatile antioxidant treatment agents are different (see Table 2 in detail), and the influence of the amounts of the nonvolatile antioxidant treatment agents on the extraction rate of cinnamaldehyde is shown in Table 2.
TABLE 2 examples 1-3 difficult to volatilize antioxidant treatment dosage and Effect
| Examples | Example 1 | Example 2 | Example 3 |
| Dosage of antioxidant treating agent difficult to volatilize | 4％ | 3％ | 2％ |
| Extraction rate of cinnamaldehyde | 2.68％ | 2.67％ | 2.62％ |
| Purity of cinnamaldehyde | 98.2％ | 98.4％ | 98.8％ |
As is clear from Table 2, the amount of the hardly volatile antioxidant is increased from 2% to 3% by weight of the total amount of cinnamon oil, the extraction rate of cinnamaldehyde is increased by 0.05%, the extraction rate of cinnamaldehyde is increased from 3% to 4%, the extraction rate of cinnamaldehyde is increased by less, only 0.01%, the purity of cinnamaldehyde is slightly decreased as the amount of the hardly volatile antioxidant is increased, and the more the amount of the hardly volatile antioxidant is, the higher the cost is from the viewpoint of economic cost. Therefore, considering comprehensively that the dosage of the difficult-to-volatilize oxidation-preventing treatment agent in the embodiment 2 is 3% of the total mass of the cinnamon oil.
Examples 4-9 differ from example 2 only in that: the sources of the difficult-to-volatilize antioxidant treatment agents are different (specifically shown in table 3), and the influence of the sources of the difficult-to-volatilize antioxidant treatment agents on the extraction rate of cinnamaldehyde is shown in table 3.
TABLE 3 sources of difficult-to-volatilize antioxidant treatments of examples 2, 4-9 and their effects
From the experimental data of comparative examples 2 and 4 to 7, it is known that the anti-oxidation treatment agent with the corresponding content of example 7, that is, the anti-oxidation treatment agent with the corresponding content of citric acid, citrate, thiol-polyethylene glycol-thiol linear homopolymer and chlorophyll mixed according to the mass ratio of 1:2.5:0.15:0.04, improves the extraction rate and purity of cinnamaldehyde, and can inhibit the oxidation of cinnamaldehyde and inhibit the self-condensation reaction of cinnamaldehyde.
The experimental data of comparative examples 7 and 8 show that, in example 8, isopropyl citrate is adopted, in example 7, tri-n-butyl citrate is adopted, and the extraction rate and purity of the isopropyl citrate corresponding to cinnamaldehyde are higher, because tri-n-butyl citrate does not contain free carboxyl, and isopropyl citrate contains free carboxyl, hydrogen bond interaction exists between the isopropyl citrate and-SH and-OH in thiol-polyethylene glycol-thiol linear homopolymer, the reducibility of the difficult-to-volatilize oxidation preventing treatment agent can be improved, and the oxidation of cinnamaldehyde can be better inhibited.
As can be seen from the experimental data of comparative examples 8 and 9, in example 8, chlorophyll a is adopted, in example 9, chlorophyll c2 is adopted, and in example 9, the extraction rate and purity of cinnamaldehyde are higher, because the content of carbon-carbon unsaturated double bonds in chlorophyll c2 is greater than that in chlorophyll a, so that the reducibility of chlorophyll c2 is stronger than that of chlorophyll a, the reducibility of the anti-oxidation treatment agent which is difficult to volatilize is improved, and the failure or denaturation of cinnamaldehyde is further reduced.
Example 10 differs from example 9 only in that: in the step S12, the power of the ultrasonic treatment is 100W, and the time of the ultrasonic treatment is 2h.
The cinnamaldehyde product obtained in detection example 10 had an extraction rate of 2.80% and a purity of 98.7%.
From the experimental data of examples 9 and 10, it is understood that the extraction rate of cinnamaldehyde at 100W of ultrasonic treatment power was 0.02% lower than that at 100W of ultrasonic treatment power, because the loss of cinnamaldehyde occurs at higher ultrasonic power, resulting in a decrease in extraction rate.
Example 11 differs from example 9 only in that: in the step S11, the particle size of the cinnamon leaf powder is 100 meshes.
The cinnamaldehyde product obtained in detection example 11 had an extraction rate of 2.84% and a purity of 98.8%.
From the experimental data of examples 9 and 11, it is apparent that the particle size of example 11 is 100 mesh, the particle size is small, and the ultrasonic treatment is performed after the cinnamon leaf powder is soaked in the solvent, so that the ultrasonic treatment time can be shortened, and the extraction rate and extraction efficiency of cinnamaldehyde can be improved.
Example 12 differs from example 11 only in that: in the step S11, the solvent is formed by mixing ethanol and ethyl acetate according to a mass ratio of 5:1.
Example 13 differs from example 11 only in that: in the step S11, the solvent is ethanol.
Example 14 differs from example 11 only in that: in the step S11, the solvent is ethyl acetate.
The extraction rate and purity of cinnamaldehyde in the cinnamaldehyde products obtained in examples 12 to 14 were measured, and the specific results are shown in Table 4.
TABLE 4 Experimental data for examples 12-14
| Examples | Example 12 | Example 13 | Example 14 |
| Extraction rate of cinnamaldehyde | 2.85％ | 2.83％ | 2.76％ |
| Purity of cinnamaldehyde | 98.9％ | 98.8％ | 98.6％ |
Table 4 examines the influence of the solvent type on the extraction rate of cinnamaldehyde, and from the experimental data of examples 11 to 14, it is known that the extraction rate of cinnamaldehyde can be improved by using the solvent compounded by ethanol and ethyl acetate, because the solvent compounded by ethanol and ethyl acetate is favorable for dissolving out cinnamaldehyde in cinnamon leaf powder, and the concentration of cinnamaldehyde in cinnamon oil is improved.
Comparative example
Comparative example 1 differs from example 3 only in that: the hardly volatile antioxidant treatment agent was derived from the preparation of comparative example 1.
Comparative example 2 differs from example 3 only in that: the less volatile antioxidant treatment was derived from preparation comparative example 2.
Comparative example 3 differs from example 3 only in that: the nonvolatile antioxidant treatment agent was replaced with the nonvolatile treatment agent (derived from preparation comparative example 3).
The extraction rate and purity of cinnamaldehyde in the cinnamaldehyde products obtained in comparative examples 1 to 3 were measured, and specific results are shown in Table 5.
TABLE 5 comparative examples 1-3 experimental data
| Comparative example | Comparative example 1 | Comparative example 2 | Comparative example 3 |
| Extraction rate of cinnamaldehyde | 2.53％ | 2.48％ | 2.31％ |
| Purity of cinnamaldehyde | 98.1％ | 98％ | 97.3％ |
As can be seen from comparing the data of comparative example 3 and example 3 in table 5, the present application improves the extraction rate and purity of cinnamaldehyde by using the less volatile antioxidant, because the less volatile antioxidant can inhibit the oxidation of cinnamaldehyde and can also inhibit the self-condensation reaction of cinnamaldehyde.
Comparing the data of comparative examples 1-2 and example 3 in table 5, it can be seen that the application adopts the difficult-to-volatilize oxidation preventing treatment agent consisting of citric acid, citrate, thiol-polyethylene glycol-thiol linear homopolymer and chlorophyll, and the thiol-polyethylene glycol-thiol linear homopolymer and chlorophyll synergistically act to remarkably improve the reducibility of the difficult-to-volatilize oxidation preventing treatment agent, and inhibit the oxidation of cinnamaldehyde, thereby improving the extraction rate and purity of cinnamaldehyde.
The extraction method of cinnamaldehyde provided in comparative example 4 comprises the following steps:
taking 0.1kg of cinnamon leaf powder with the particle size of 50 meshes, soaking the cinnamon leaf powder in 2kg of ethanol for 5 hours, performing ultrasonic treatment again, wherein the power of the ultrasonic treatment is 75W, the time of the ultrasonic treatment is 30min, and the interval time of the ultrasonic treatment is 5s/3s, obtaining an ultrasonic solution, removing the ethanol in the ultrasonic solution, and performing steam distillation extraction for 1 hour to obtain a cinnamaldehyde product.
The cinnamaldehyde product obtained in comparative example 4 was examined to have an extraction rate of 2.38% and a purity of 97.6%.
Experimental data of comparative examples 1-14 and comparative example 4 effectively relieve the problem that cinnamaldehyde is oxidized and subjected to self-condensation reaction due to long extraction time and high temperature in the process of extracting the cinnamaldehyde by steam distillation, and improve the extraction rate of the cinnamaldehyde.
The present embodiment is merely illustrative of the present application and is not intended to be limiting, and those skilled in the art, after having read the present specification, may make modifications to the present embodiment without creative contribution as required, but is protected by patent laws within the scope of the claims of the present application.
Claims (9)
1. The extraction method of the cinnamaldehyde is characterized by comprising the following steps of:
s1, soaking cinnamon leaf powder in a solvent, performing ultrasonic treatment, condensing steam generated in the ultrasonic treatment process, and separating oil from water to obtain cinnamon oil;
s2, adding a difficult-to-volatilize oxidation-preventing treating agent into the cinnamon oil, mixing, and then introducing inert gas for rectification separation to obtain cinnamaldehyde; the mass ratio of the difficult-to-volatilize oxidation preventing treating agent to the cinnamon oil is (2-4) 100; the non-volatile oxidation preventing treating agent comprises citric acid, citrate, mercaptan-polyethylene glycol-mercaptan linear homopolymer and chlorophyll.
2. The extraction method of cinnamaldehyde according to claim 1, wherein the mass ratio of citric acid, citrate, thiol-polyethylene glycol-thiol linear homopolymer to chlorophyll is 1 (2-3) (0.1-0.15) (0.03-0.05).
3. The method for extracting cinnamaldehyde according to claim 2, wherein the mass ratio of citric acid, citrate, thiol-polyethylene glycol-thiol linear homopolymer and chlorophyll is 1:2.5:0.15:0.04.
4. The method for extracting cinnamaldehyde according to claim 1, wherein the citrate is isopropyl citrate.
5. The method for extracting cinnamaldehyde according to claim 1, wherein the chlorophyll is chlorophyll c2.
6. The method for extracting cinnamaldehyde according to claim 1, wherein the mass ratio of the difficult-to-volatilize antioxidant treating agent to the cinnamon oil is 3:100.
7. The method according to claim 1, wherein in the step S1, the power of the ultrasonic treatment is 80-100W, and the time of the ultrasonic treatment is 2-3h.
8. The method for extracting cinnamaldehyde according to claim 1, wherein the solvent is formed by mixing ethanol and ethyl acetate according to a mass ratio of (3-5): 1.
9. The method for extracting cinnamaldehyde according to claim 1, wherein the particle size of the cinnamon leaf powder is 50-100 mesh.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8503470D0 (en) * | 1984-02-09 | 1985-03-13 | Colgate Palmolive Co | Stabilising of cinnamic aldehyde |
| KR20030033282A (en) * | 2001-10-19 | 2003-05-01 | (주)허벤텍 | Extract of Cinnamomi cortex containing Cinnamaldehyde |
| CN109608322A (en) * | 2019-02-01 | 2019-04-12 | 广东工业大学 | A kind of extracting method of cinnamic acid |
| CN113501751A (en) * | 2021-08-18 | 2021-10-15 | 南宁市和昇香料香精有限公司 | Method for preparing high-purity cinnamaldehyde by efficiently rectifying and purifying cinnamon oil |
| CN114304585A (en) * | 2021-12-30 | 2022-04-12 | 武汉能迈科实业有限公司 | Preparation method of cinnamaldehyde not easy to oxidize |
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- 2023-03-03 CN CN202310199112.3A patent/CN116120159A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8503470D0 (en) * | 1984-02-09 | 1985-03-13 | Colgate Palmolive Co | Stabilising of cinnamic aldehyde |
| KR20030033282A (en) * | 2001-10-19 | 2003-05-01 | (주)허벤텍 | Extract of Cinnamomi cortex containing Cinnamaldehyde |
| CN109608322A (en) * | 2019-02-01 | 2019-04-12 | 广东工业大学 | A kind of extracting method of cinnamic acid |
| CN113501751A (en) * | 2021-08-18 | 2021-10-15 | 南宁市和昇香料香精有限公司 | Method for preparing high-purity cinnamaldehyde by efficiently rectifying and purifying cinnamon oil |
| CN114304585A (en) * | 2021-12-30 | 2022-04-12 | 武汉能迈科实业有限公司 | Preparation method of cinnamaldehyde not easy to oxidize |
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