CN112602785A - Fat-soluble natural antioxidant and preparation method and application thereof - Google Patents
Fat-soluble natural antioxidant and preparation method and application thereof Download PDFInfo
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- CN112602785A CN112602785A CN202011300363.9A CN202011300363A CN112602785A CN 112602785 A CN112602785 A CN 112602785A CN 202011300363 A CN202011300363 A CN 202011300363A CN 112602785 A CN112602785 A CN 112602785A
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- fat
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- natural antioxidant
- tar
- dimethoxyphenol
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- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 61
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000011269 tar Substances 0.000 claims abstract description 27
- QSZCGGBDNYTQHH-UHFFFAOYSA-N 2,3-dimethoxyphenol Chemical class COC1=CC=CC(O)=C1OC QSZCGGBDNYTQHH-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 10
- 235000013305 food Nutrition 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 methoxyphenol compound Chemical class 0.000 claims description 16
- IFNDEOYXGHGERA-UHFFFAOYSA-N 2-methoxy-5-methylphenol Chemical compound COC1=CC=C(C)C=C1O IFNDEOYXGHGERA-UHFFFAOYSA-N 0.000 claims description 10
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 2,4-dimethoxyphenol Chemical compound COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 claims description 8
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 8
- CHWNEIVBYREQRF-UHFFFAOYSA-N 4-Ethyl-2-methoxyphenol Chemical compound CCC1=CC=C(O)C(OC)=C1 CHWNEIVBYREQRF-UHFFFAOYSA-N 0.000 claims description 8
- 241000196324 Embryophyta Species 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 claims description 6
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 claims description 5
- LXUHYMCTFZFCCV-UHFFFAOYSA-N 3,5-dimethoxy-2-methylphenol Chemical compound COC1=CC(O)=C(C)C(OC)=C1 LXUHYMCTFZFCCV-UHFFFAOYSA-N 0.000 claims description 5
- BNMCPQJHABZPMJ-UHFFFAOYSA-N 4,5-dimethoxy-2-methylphenol Chemical compound COC1=CC(C)=C(O)C=C1OC BNMCPQJHABZPMJ-UHFFFAOYSA-N 0.000 claims description 5
- 235000017166 Bambusa arundinacea Nutrition 0.000 claims description 5
- 235000017491 Bambusa tulda Nutrition 0.000 claims description 5
- 235000015334 Phyllostachys viridis Nutrition 0.000 claims description 5
- 239000011425 bamboo Substances 0.000 claims description 5
- 239000011297 pine tar Substances 0.000 claims description 5
- 229940068124 pine tar Drugs 0.000 claims description 5
- CAWZFQGJUGEKFU-UHFFFAOYSA-N 5-ethyl-2-methoxyphenol Chemical compound CCC1=CC=C(OC)C(O)=C1 CAWZFQGJUGEKFU-UHFFFAOYSA-N 0.000 claims description 4
- 244000025254 Cannabis sativa Species 0.000 claims description 4
- 239000010902 straw Substances 0.000 claims description 4
- 239000011276 wood tar Substances 0.000 claims description 4
- 244000082204 Phyllostachys viridis Species 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 6
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000002440 industrial waste Substances 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000004064 recycling Methods 0.000 abstract description 2
- 239000002641 tar oil Substances 0.000 abstract description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 10
- 239000004258 Ethoxyquin Substances 0.000 description 8
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 8
- 235000019285 ethoxyquin Nutrition 0.000 description 8
- 229940093500 ethoxyquin Drugs 0.000 description 8
- 239000004519 grease Substances 0.000 description 6
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 5
- 235000010388 propyl gallate Nutrition 0.000 description 5
- 239000000473 propyl gallate Substances 0.000 description 5
- 229940075579 propyl gallate Drugs 0.000 description 5
- 241001330002 Bambuseae Species 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- 230000000711 cancerogenic effect Effects 0.000 description 3
- 231100000315 carcinogenic Toxicity 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 3
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004263 Guaiac resin Substances 0.000 description 2
- 229920000932 Gum guaicum Polymers 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000003064 anti-oxidating effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000021466 carotenoid Nutrition 0.000 description 2
- 150000001747 carotenoids Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019278 guaiac resin Nutrition 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000010384 tocopherol Nutrition 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- 229960001295 tocopherol Drugs 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- AZJQQNWSSLCLJN-UHFFFAOYSA-N 2-ethoxyquinoline Chemical compound C1=CC=CC2=NC(OCC)=CC=C21 AZJQQNWSSLCLJN-UHFFFAOYSA-N 0.000 description 1
- YBMTWYWCLVMFFD-UHFFFAOYSA-N 3-methylbutyl 3,4,5-trihydroxybenzoate Chemical compound CC(C)CCOC(=O)C1=CC(O)=C(O)C(O)=C1 YBMTWYWCLVMFFD-UHFFFAOYSA-N 0.000 description 1
- RPWFJAMTCNSJKK-UHFFFAOYSA-N Dodecyl gallate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 RPWFJAMTCNSJKK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 244000302661 Phyllostachys pubescens Species 0.000 description 1
- 235000003570 Phyllostachys pubescens Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000010386 dodecyl gallate Nutrition 0.000 description 1
- 239000000555 dodecyl gallate Substances 0.000 description 1
- 229940080643 dodecyl gallate Drugs 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000010387 octyl gallate Nutrition 0.000 description 1
- 239000000574 octyl gallate Substances 0.000 description 1
- NRPKURNSADTHLJ-UHFFFAOYSA-N octyl gallate Chemical compound CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 NRPKURNSADTHLJ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/06—Preservation of finished products
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/06—Preservation of finished products
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention provides a fat-soluble natural antioxidant and a preparation method and application thereof, belonging to the technical field of industrial waste liquid recycling. The preparation method of the fat-soluble natural antioxidant provided by the invention comprises the following steps: heating and rectifying tar which is a byproduct generated when the plant material is charred until the total mass content of methoxyphenol compounds and dimethoxyphenol compounds in the obtained fraction is more than or equal to 60%, and collecting the fraction to obtain a fat-soluble natural antioxidant; the temperature of the heating rectification is 240-280 ℃. The invention takes the tar oil by-product produced in the process of burning the plant material as the raw material to prepare the fat-soluble natural antioxidant, has wide raw material source, low price and low production cost, and can be widely produced and used; the fat-soluble natural antioxidant prepared by the invention contains methoxyphenol and dimethoxyphenol compounds, has excellent oxidation resistance, can be used for oxidation resistance of foods and daily chemical products, and is most suitable for being used as a feed antioxidant.
Description
Technical Field
The invention relates to the technical field of industrial waste liquid recycling, in particular to a fat-soluble natural antioxidant and a preparation method and application thereof.
Background
The fat-soluble antioxidant is a substance which is uniformly distributed in the grease, can well play an antioxidation role on the grease and the food containing the grease and can prevent the oxidation rancidity of the grease and the food containing the grease. The fat-soluble antioxidants are divided into two categories of artificially synthesized fat-soluble antioxidants and natural fat-soluble antioxidants. Most of the antioxidants currently used in various countries are synthesized artificially, and Butyl Hydroxyanisole (BHA), dibutyl hydroxytoluene (BHT), Propyl Gallate (PG), Ethoxyquinoline (EMQ), tert-butylhydroquinone (TBHQ), and the like are widely used. The natural fat-soluble antioxidant includes guaiac resin, tocopherol mixed concentrate, carotenoid, etc.
However, BHA is suspected of being carcinogenic, and in 1986, FAO/WHO also reported that large doses of BHA were carcinogenic in rat forestomach and caused esophageal hyperplasia in pigs and dogs. However, in 1989, when the FAO/WHO was reevaluated, it was thought that the rat forestomach was carcinogenic only at particularly high doses (20g/kg), and had no deleterious effects on pigs and dogs. Since the human has no anterior stomach, ADI value is set to 0-0.5 mg/kg, and the ADI is allowed to be used in food. BHT has the suspicion of inhibiting the activity of human respiratory enzymes. The FDA in the united states was once banned, and countries greece, turkey, etc. were banned. Other safety can be ensured as proved by later reasons, and the ADI value is reduced to 0-0.3mg/kg for continuous use. The feed formula contains a large amount of unsaturated fatty acid ester, and only fat-soluble antioxidants can be used. BHT is a white crystalline particle, and even if it is finely ground, in a premix or a compound feed composed of a mixture of BHT and easily oxidizable components in the feed, each component is still a single particle, and therefore, BHT cannot sufficiently exert an antioxidant effect, which is a key reason why BHT cannot sufficiently exert its effect. PG cannot be used alone in feed due to its high price and low solubility in oil and fat. In addition to propyl gallate, octyl gallate, isoamyl gallate, dodecyl gallate and the like, are substantially similar to PG. The disadvantage of EMQ is that the color change of EMQ is too fast and too big, when used in large amount in premix, the EMQ color is deepened rapidly, which is often mistaken for the quality change of feed, and is substantially caused by the color change of EMQ, and the EMQ color does not affect the quality of feed, which is also an important reason that EMQ is not willing to be added in food. Furthermore, the antioxidant effect of EMQ on certain oils is not ideal. TBHQ has better antioxidant effect than BHA and BHT, but has higher price and is difficult to accept in feed. Natural antioxidants such as guaiac resin, tocopherol mixed concentrate, carotenoids, etc. are more expensive and have hardly been applied in feeds. Therefore, the fat-soluble natural antioxidant with excellent oxidation resistance and low preparation cost has important significance.
A great amount of tar is produced as a byproduct in the burning of carbon, active carbon and the like by various plant materials, such as wood tar, bamboo tar, straw tar, grass tar and the like, and the tar is black and smelly and seriously pollutes the environment when being discharged at will. To date, no report has been made on the use of tar for the preparation of fat-soluble antioxidants.
Disclosure of Invention
The invention aims to provide a fat-soluble natural antioxidant, a preparation method and application thereof.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a preparation method of a fat-soluble natural antioxidant, which comprises the following steps:
heating and rectifying tar which is a byproduct generated when the plant material is charred until the total mass content of methoxyphenol compounds and dimethoxyphenol compounds in the obtained fraction is more than or equal to 60%, and collecting the fraction to obtain a fat-soluble natural antioxidant;
the temperature of the heating rectification is 240-280 ℃.
Preferably, the tar comprises wood tar, pine tar, bamboo tar, straw tar or grass tar.
Preferably, the pressure of the heated rectification is 760 mmHg.
Preferably, the temperature of the heating rectification is 250-260 ℃.
Preferably, the heating rectification is performed by using high-temperature heat conduction oil.
Preferably, the total mass content of the methoxyphenol compounds and the dimethoxyphenol compounds in the fraction is detected by GC-MS.
The fat-soluble natural antioxidant prepared by the preparation method in the technical scheme comprises a methoxyphenol compound and a dimethoxyphenol compound, wherein the methoxyphenol compound comprises one or more of 2-methoxy-5-methylphenol, 2-methoxy-5-ethylphenol, 2-methoxy-4-ethylphenol and 4-vinyl-2-methoxyphenol, and the dimethoxyphenol compound comprises 2, 6-dimethoxyphenol, 2, 4-dimethoxyphenol, 4, 5-dimethoxy-2-methylphenol and 3, 5-dimethoxy-2-methylphenol.
The invention provides application of the fat-soluble natural antioxidant in the technical scheme in food, daily chemical products and feed.
The invention provides a preparation method of a fat-soluble natural antioxidant, which comprises the following steps: heating and rectifying tar which is a byproduct generated when the plant material is charred until the total mass content of methoxyphenol compounds and dimethoxyphenol compounds in the obtained fraction is more than or equal to 60%, and collecting the fraction to obtain a fat-soluble natural antioxidant; the temperature of the heating rectification is 240-280 ℃. The invention takes the tar oil by-product produced in the process of burning the plant material as the raw material to prepare the fat-soluble natural antioxidant, has wide raw material source, low price and low production cost, and can be widely produced and used; the fat-soluble natural antioxidant prepared by the invention contains methoxyphenol and dimethoxyphenol compounds, is easy to dissolve in grease, has excellent antioxidant performance, can be used for the antioxidation of foods and daily chemical products, and is most suitable for being used as a feed antioxidant.
The invention realizes the full utilization of the tar which is the byproduct in the charcoal burning of the plant material, and avoids the environmental pollution of the tar.
Detailed Description
The invention provides a preparation method of a fat-soluble natural antioxidant, which comprises the following steps:
heating and rectifying tar which is a byproduct generated when the plant material is charred until the total mass content of methoxyphenol compounds and dimethoxyphenol compounds in the obtained fraction is more than or equal to 60%, and collecting the fraction to obtain a fat-soluble natural antioxidant;
the temperature of the heating rectification is 240-280 ℃.
In the present invention, unless otherwise specified, all the starting materials required for the preparation are commercially available products well known to those skilled in the art.
In the invention, the tar by-produced in the process of burning the plant material is preferably a commercial product, and the tar preferably comprises wood tar, pine tar, bamboo tar, straw tar or grass tar.
In the present invention, the thermal distillation is preferably performed in a distillation column, and the distillation column is not particularly limited in the present invention, and may be a distillation column known in the art.
In the present invention, the pressure of the thermal distillation is preferably 760 mmHg.
In the invention, the temperature of the heating rectification is 240-280 ℃, preferably 250-260 ℃, and more preferably 255 ℃. The heating rectification is preferably carried out by using high-temperature heat conduction oil, the high-temperature heat conduction oil is not particularly limited by the invention, and the high-temperature heat conduction oil can be a commercially available product well known in the field, and in the embodiment of the invention, the type of the high-temperature heat conduction oil is specifically IOTA-255A.
The total mass content of the methoxyphenol compounds and the dimethoxyphenol compounds in the fractions is preferably detected by GC-MS. In the present invention, the conditions for the GC-MS detection are preferably: sample inlet temperature 240 ℃, detector temperature 250 ℃, temperature rise program: the temperature is increased to 200 ℃ at the speed of 10 ℃/min at the initial 100 ℃, and the temperature is preserved for 50 min.
The process for collecting the fractions is not particularly limited in the present invention, and may be performed according to a process well known in the art.
The fat-soluble natural antioxidant prepared by the preparation method in the technical scheme comprises a methoxyphenol compound and a dimethoxyphenol compound, wherein the methoxyphenol compound comprises one or more of 2-methoxy-5-methylphenol, 2-methoxy-5-ethylphenol, 2-methoxy-4-ethylphenol and 4-vinyl-2-methoxyphenol, and the dimethoxyphenol compound comprises 2, 6-dimethoxyphenol, 2, 4-dimethoxyphenol, 4, 5-dimethoxy-2-methylphenol and 3, 5-dimethoxy-2-methylphenol.
In the fat-soluble natural antioxidant prepared by the invention, the total mass content of the methoxyl phenolic compound and the dimethoxyl phenolic compound is more than or equal to 60 percent, and the fat-soluble antioxidant has higher quality.
The invention provides application of the fat-soluble natural antioxidant in the technical scheme in food, daily chemical products and feed. The method of the present invention is not particularly limited, and the method may be applied according to a method known in the art.
The technical solution of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Putting 1000 kg of bamboo tar byproduct generated by charring of moso bamboos produced by Fujian Sanming into a heating kettle of a rectifying tower, performing heating rectification by using high-temperature heat conduction oil (type IOTA-255A) under the conditions of pressure of 760mmHg and temperature of 240-280 ℃ to obtain 434 kg of fraction, namely fat-soluble natural antioxidant (marked as A), detecting the components of the fat-soluble natural antioxidant by using GC-MS (conditions are that the injection port temperature is 240 ℃, the detector temperature is 250 ℃, the temperature rising program is initial 100 ℃, the temperature rises to 200 ℃ at 10 ℃/min, the temperature is kept for 50min), calculating according to peak area, and preparing the fat-soluble natural antioxidant A containing 12.5% of 2-methoxy-5-methylphenol, 8.6% of 2-methoxy-5-ethylphenol, 15.7% of 4-vinyl-2-methoxyphenol and 17.9% of 2, 6-dimethoxyphenol, 19.0 percent of 4, 5-dimethoxy-2-methylphenol and 3.13 percent of 3, 5-dimethoxy-2-methylphenol, namely the total mass content of the methoxyphenol and the dimethoxyphenol in the prepared fat-soluble natural antioxidant A is 76.83 percent.
Performance testing
Evaluation of antioxidant effect: carrying out an experiment by using mixed oil obtained by mixing lard oil and soybean oil according to the volume ratio of 1:1, taking 40 250mL beakers (numbered), processing 2 parallel samples in each beaker, and taking an average value of results; fat-soluble natural antioxidant A was added in an amount of 0.1% in each treatment. All beakers were placed at 50 ℃ and the peroxide number (POV) and TBA (optical density) of the mixed oil were measured every other day, while blank (i.e., no fat-soluble natural antioxidant A was added) and commercially available ethoxyquin were used as a comparison, and the results are shown in tables 1 and 2.
TABLE 1 peroxide number (POV) (unit: mg/kg) data for fat-soluble natural antioxidant A prepared in example 1
| Time | Blank control group | Ethoxyquin | Fat-soluble natural antioxidant A |
| Initiation of | 4.52 | 4.95 | 4.66 |
| Day one | 4.91 | 5.08 | 5.23 |
| The next day | 5.95 | 7.24 | 6.99 |
| The third day | 8.03 | 9.03 | 8.71 |
| The fourth day | 12.77 | 11.12 | 9.90 |
TABLE 2 TBA (unit: absorbance/kg) data of the fat-soluble natural antioxidant A prepared in example 1
| Time | Blank control group | Ethoxyquin | Fat-soluble natural antioxidant A |
| Initiation of | 323.22 | 336.75 | 324.75 |
| Day one | 357.45 | 348.06 | 344.59 |
| The next day | 687.11 | 363.66 | 398.60 |
| The third day | 892.74 | 558.39 | 476.83 |
| The fourth day | 1047.9 | 675.85 | 561.28 |
As can be seen from tables 1 and 2, the fat-soluble antioxidant of the present invention has more excellent antioxidant effect compared to the blank and ethoxyquin.
Example 2
Putting 1000 kg of pine tar byproduct generated during the charring of pine produced by Fujiande chemical into a heating kettle of a rectifying tower, performing heating rectification by using high-temperature heat conduction oil (IOTA-255A) under the conditions of pressure of 760mmHg and temperature of 240-280 ℃ to obtain 358 kg of fraction, namely fat-soluble natural antioxidant (marked as B), detecting the components by GC-MS (the conditions are that the injection port temperature is 240 ℃, the detector temperature is 250 ℃, the temperature rising program is initial 100 ℃, the temperature rises to 200 ℃ at the rate of 10 ℃/min, and the temperature is kept for 50min), calculating according to peak areas, and preparing the fat-soluble natural antioxidant B containing 10.3% of 2-methoxy-5-methylphenol, 8.2% of 2-methoxy-4-ethylphenol, 14.5% of 4-vinyl-2-methoxyphenol and 18.4% of 2, 4-dimethoxyphenol, 6.2 percent of 4, 5-dimethoxy-2-methylphenol and 5.91 percent of 3, 5-dimethoxy-2-methylphenol. In the prepared fat-soluble natural antioxidant B, the total mass content of the methoxyphenol and the dimethoxyphenol is 63.51 percent.
Performance testing
The fat-soluble natural antioxidant B prepared in example 2 was tested for its antioxidant effect according to the above-mentioned performance test method in example 1, while blank (i.e., without adding the fat-soluble natural antioxidant B) and commercial ethoxyquin were used as a comparison, and the results are shown in tables 3 and 4.
TABLE 3 peroxide number (POV) (unit: mg/kg) data for fat-soluble natural antioxidant B prepared in example 2
| Time | Blank control group | Ethoxyquin | Fat-soluble natural antioxidant B |
| Initiation of | 4.63 | 4.82 | 4.75 |
| Day one | 4.99 | 5.01 | 5.34 |
| The next day | 5.92 | 7.34 | 6.87 |
| The third day | 8.24 | 9.25 | 8.93 |
| The fourth day | 12.96 | 11.01 | 10.21 |
TABLE 4 TBA (unit: absorbance/kg) data of fat-soluble natural antioxidant B prepared in example 2
| Time | Blank control group | Ethoxyquin | Fat-soluble natural antioxidant B |
| Initiation of | 325.56 | 338.74 | 335.83 |
| Day one | 358.20 | 350.12 | 346.70 |
| The next day | 689.91 | 373.44 | 396.38 |
| The third day | 899.79 | 561.35 | 483.49 |
| The fourth day | 1059.92 | 682.56 | 552.33 |
As can be seen from tables 3 and 4, the fat-soluble antioxidant prepared from pine tar has more excellent antioxidant effect, as compared with the blank and ethoxyquin.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (8)
1. The preparation method of the fat-soluble natural antioxidant is characterized by comprising the following steps:
heating and rectifying tar which is a byproduct generated when the plant material is charred until the total mass content of methoxyphenol compounds and dimethoxyphenol compounds in the obtained fraction is more than or equal to 60%, and collecting the fraction to obtain a fat-soluble natural antioxidant;
the temperature of the heating rectification is 240-280 ℃.
2. The method of claim 1, wherein the tar comprises wood tar, pine tar, bamboo tar, straw tar, or grass tar.
3. The production method according to claim 1, wherein the pressure of the thermal rectification is 760 mmHg.
4. The preparation method according to claim 1, wherein the temperature of the heated rectification is 250-260 ℃.
5. The production method according to claim 1 or 4, characterized in that the thermal distillation is performed using high-temperature thermal oil.
6. The method according to claim 1, wherein the total mass content of the methoxyphenol compound and the dimethoxyphenol compound in the fraction is measured by GC-MS.
7. The fat-soluble natural antioxidant prepared by the preparation method of any one of claims 1 to 6 comprises a methoxyphenol compound and a dimethoxyphenol compound, wherein the methoxyphenol compound comprises one or more of 2-methoxy-5-methylphenol, 2-methoxy-5-ethylphenol, 2-methoxy-4-ethylphenol and 4-vinyl-2-methoxyphenol, and the dimethoxyphenol compound comprises 2, 6-dimethoxyphenol, 2, 4-dimethoxyphenol, 4, 5-dimethoxy-2-methylphenol and 3, 5-dimethoxy-2-methylphenol.
8. The use of the fat-soluble natural antioxidant according to claim 7 in foods, daily use chemicals and feeds.
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