CN1106370C - Preparation of oil soluble tea polyphenol derivative used as edible oil antioxidant - Google Patents
Preparation of oil soluble tea polyphenol derivative used as edible oil antioxidant Download PDFInfo
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- CN1106370C CN1106370C CN00113162A CN00113162A CN1106370C CN 1106370 C CN1106370 C CN 1106370C CN 00113162 A CN00113162 A CN 00113162A CN 00113162 A CN00113162 A CN 00113162A CN 1106370 C CN1106370 C CN 1106370C
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- 239000003921 oil Substances 0.000 title claims abstract description 57
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 32
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 26
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 18
- 239000008157 edible vegetable oil Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 15
- 241001122767 Theaceae Species 0.000 title abstract description 17
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 230000008707 rearrangement Effects 0.000 claims abstract description 8
- 238000005917 acylation reaction Methods 0.000 claims abstract description 5
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 88
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 56
- 235000019198 oils Nutrition 0.000 claims description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 28
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 26
- 239000007864 aqueous solution Substances 0.000 claims description 24
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 230000003252 repetitive effect Effects 0.000 claims description 15
- 238000005201 scrubbing Methods 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 10
- -1 ester acyl chlorides Chemical class 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 238000006722 reduction reaction Methods 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 6
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 claims description 5
- 235000005074 zinc chloride Nutrition 0.000 claims description 5
- 239000011592 zinc chloride Substances 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 238000006462 rearrangement reaction Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 3
- 244000270834 Myristica fragrans Species 0.000 claims description 3
- 235000009421 Myristica fragrans Nutrition 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000001702 nutmeg Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 2
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 244000269722 Thea sinensis Species 0.000 claims 8
- 230000003647 oxidation Effects 0.000 abstract description 12
- 238000007254 oxidation reaction Methods 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 235000013305 food Nutrition 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 5
- 230000009467 reduction Effects 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000006179 O-acylation Effects 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000000295 fuel oil Substances 0.000 abstract 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 14
- 238000007670 refining Methods 0.000 description 14
- 230000008676 import Effects 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- 235000010265 sodium sulphite Nutrition 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 9
- 235000006708 antioxidants Nutrition 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000004519 grease Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 240000008415 Lactuca sativa Species 0.000 description 4
- 235000012045 salad Nutrition 0.000 description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 229910001448 ferrous ion Inorganic materials 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000000852 hydrogen donor Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229930014669 anthocyanidin Natural products 0.000 description 1
- 150000001452 anthocyanidin derivatives Chemical class 0.000 description 1
- 235000008758 anthocyanidins Nutrition 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000002019 anti-mutation Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000019261 food antioxidant Nutrition 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 230000035764 nutrition Effects 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
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- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to a preparation method of an oil soluble tea polyphenol derivative used as an edible oil antioxidant. The method is characterized in that the method adopts the raw materials of water soluble tea polyphenol, acyl chloride of six to thirty carbons, an acylation catalyst, a rearrangement auxiliary agent, a reducer, etc. The water soluble tea polyphenol is decatalyzed, desalted, washed, dehydrated and dried through chemical reactions, such as O-acylation, rearrangement, reduction, etc., namely, a fat long chain is introduced in a molecular structure of the water soluble tea polyphenol so that the tea polyphenol can have oil solubility on the premise for keeping the oxidation resisting characteristic. A product of the oil soluble tea polyphenol derivative has optimal solubility in heavy oil foods and edible oil, and has the excellent oxidation resisting characteristic.
Description
The present invention relates to a kind of alkyl derivative preparation method of the polyhydroxy-benzene as oxidation inhibitor, particularly as the preparation of oil soluble tea polyphenol derivative of edible oil antioxidant.
Tea-polyphenol has another name called tea tannin, the platymiscium polyphenols, according to GB8313-87, tea-polyphenol is meant the general name that produces the phenolic compound of combined reaction in the Aqua Folium Camelliae sinensis extractive substance with ferrous ion, tea-polyphenol class material is the essential substance of decision tealeaves local flavor and quality, being again a kind of good natural oxidation inhibitor, also is to the active material of the pharmacological action of tealeaves.In recent years, the development and use of tea-polyphenol and derivative thereof have caused the personages' of each side such as domestic and international Tea Science, medicine and pharmacology and grocery trade very big concern.Company in the tea-polyphenol molecular structure or o-phenyl phenol base have the activity of hydrogen donor, great reducing power is arranged, this just makes tea-polyphenol not only have stronger oxidation-resistance, and antibacterial in addition, press down enzyme, anticancer, anti-mutation, radioprotective, anti-ageing, remove a series of biologies and physiological and pharmacological activity such as human free radical and hypoglycemic.At present, the foodstuffs industry forward of China is natural, nutrition, health care, meticulous direction develop, have 2 of big toxic side effect, the use in foodstuffs industry of the oxidation inhibitor of 6-toluene di-tert-butyl phenol (BHT), the chemosynthesis such as (BHA) of tertiary butyl-4-hydroxy phenylmethylether has been subjected to very big restriction.The phenolic hydroxyl group of tea-polyphenol has the activity of hydrogen donor, great resistance of oxidation is arranged, it is a kind of food antioxidant of Nantural non-toxic, by the approval of the national foodstuff additive technical committee for standardization (TCST) and the Ministry of Health, classify GB2760-86 " foodstuff additive use hygienic standard " (nineteen ninety amendments) as.
The oxidation inhibitor that tea-polyphenol is made grease and oleaginous food at field of food is aspect one that studies at most at present.The result shows that the tea-polyphenol of interpolation 0.02% has just produced good antioxygenation to salad oil.Compare with blank sample, when preserving 10 days under 65 ℃ of conditions, tea-polyphenol is 88% to the inhibiting rate of salad oil peroxide value, and BHA is 44% to the inhibiting rate of salad oil peroxide value; Tea-polyphenol has better antioxidant effect than BHA to salad oil.In addition, tea-polyphenol all has the oxidation-resistance of excellence to fish oil, to refining rape seed oil, to lard.Many research has drawn consistent conclusion: tea-polyphenol has showed more natural oxidation inhibitor V
E, stronger antioxygenation such as synthetic oxidation inhibitor BHA, as the oxidation inhibitor of foodstuffs industry, the quality guaranteed period 3-6 that can prolong grease and oleaginous food doubly, the synthetic oxidation inhibitor of complete alternative life-time service, its Application Prospect is very wide.
Although tea-polyphenol has above-mentioned fabulous oxidation-resistance and good bio-physiological activity, can be applicable to food, daily use chemicals, medicine and other fields, still be in theoretical research stage at present mostly, really be not used for suitability for industrialized production.Especially as the antioxidant of food oils, still fail so far to use on a large scale at oil prodution industry.One of the main reasons is its solvability soluble in water, as to be insoluble in oil.To be example as greasy antioxidant, when studying tea-polyphenol at present, generally be earlier tea-polyphenol to be dissolved in dehydrated alcohol to greasy antioxygenation, add in the grease again.Although played antioxygenation; but after the ethanol evaporation; the part tea-polyphenol is the crystal form precipitation again and separates out from grease; not only influence the outward appearance of oil; and the mouthfeel that residual ethanol also can influence oil also has the patent report of preparation oil-soluble tea polyphenol at present, but mostly adopts the organic solvent be difficult for removing, and the active phenolic hydroxyl group in esterification (or acidylate) back remains little; the anti-oxidant activity loss of product is bigger, and this will certainly make the antioxidant property of product descend.
Purpose of the present invention is intended to overcome above-mentioned deficiency of the prior art; by with water miscible tea-polyphenol through chemical reactions such as 0-acidylate, rearrangement, reduction; in the tea-polyphenol molecular structure, introduce fatty long-chain, have oil-soluble preparation of oil soluble tea polyphenol derivative as edible oil antioxidant thereby provide under a kind of prerequisite that keeps the tea-polyphenol anti-oxidation characteristics.
Content of the present invention is: a kind of preparation of oil soluble tea polyphenol derivative as edible oil antioxidant is characterized in that being made up of the following step:
(1) acylation reaction: 100 parts of (weight, back are together) tea-polyphenol, 50～500 parts of acyl chlorides, 0.05～10 part of catalyzer adding belt stirrer, thermometer, gas are imported and exported in the reactor of mouth, logical nitrogen, heating is also stirred, be warming up to and react under 50～180 ℃ till the system homogeneous transparent, be cooled to room temperature;
(2) rearrangement reaction: reset auxiliary agent with 10～400 parts and add in the reactant, heat and be stirred to and solidify, place baking oven 100～180 ℃ of insulations 0.5～5 hour again, be cooled to room temperature, add 100～1000 parts of pH＜2 acid/aqueous solution and 100～1000 parts of extraction agents again, the phase of anhydrating is divided in the back that stirs, and extraction agent is used the acid of pH＜2/aqueous solution repetitive scrubbing 5 times mutually;
(3) reduction reaction: add 50～500 parts of 20% reductive agent/aqueous solution in above-mentioned product and stirred 5～72 hours, extraction agent is washed with water to neutrality mutually, removes extraction agent and promptly makes product, and product is transparent thick liquid of light brown or light brown powder.
In the content of the present invention: described tea-polyphenol is meant the general name that produces the phenolic compound of combined reaction in the tealeaves solvent extractive substance with ferrous ion, comprises four big class materials such as catechin, flavonoid compound, anthocyanidin, phenolic acid.
In the described acylation reaction of content of the present invention: acyl chlorides is 80～250 parts preferably, and catalyzer is 0.5～5 part preferably; In the described rearrangement reaction: reset auxiliary agent and be 80～200 parts preferably, acid/aqueous solution is 100400 parts preferably, and extraction agent is 100～200 parts preferably; In the described reduction reaction: 20% reductive agent/aqueous solution is 150～300 parts.
In the content of the present invention: described acyl chlorides is at least a in the acyl chlorides of the acyl chlorides of valeryl chloride, caproyl chloride, oenanthyl chloro, capryl(yl)chloride, certain herbaceous plants with big flowers acyl chlorides, lauroyl chloride, nutmeg acyl chlorides, palmityl chloride, stearic acid chloride, soft ester acyl chlorides, oleic acyl chlorides, linoleic acyl chlorides, coconut oil and/or oleic acid.
In the content of the present invention: described catalyzer is at least a in tosic acid, boron trifluoride diethyl etherate, sulfuric acid and/or the phosphoric acid.
In the content of the present invention: described rearrangement agent is Zinc Chloride Anhydrous and/or aluminum trichloride (anhydrous).
In the content of the present invention: described extraction agent is at least a in ether, sherwood oil and/or the hexanaphthene.
In the content of the present invention: described reductive agent is at least a in zinc powder, the sulfurous gas aqueous solution, S-WAT, sodium bisulfite and/or the Sulfothiorine.
In the content of the present invention: described acid is at least a in hydrochloric acid, sulfuric acid and/or the phosphoric acid.
The oil soluble tea polyphenol derivative edible oil antioxidant that the present invention makes is transparent thick liquid of light brown or sundown pressed powder.Raw material according to employing is different with proportioning, can obtain the product of different performance, can be used as the oxidation inhibitor of animal grease and Vegetable oil lipoprotein.
Compare with existing basic technology, the present invention has following characteristics:
(1) making principle is: tea-polyphenol behind chemical reactions such as O-acidylate, rearrangement, reduction again through remove catalyzer, desalt, wash dehydration, drying gets oil soluble tea polyphenol derivative.The O-acidylate is to realize by the phenolic hydroxyl group effect dehydrochlorination of the acyl chlorides of higher fatty acid and tea-polyphenol; reset that the acyl rearrangement then make part that the O-acidylate takes place is close to the tea-polyphenol molecular structure to have on the active position of nucleophilic and phenolic hydroxyl group is discharged, the reductive purpose be make tea-polyphenol deposit or in building-up process oxidized quinoid construction recovery be phenolic hydroxyl group.This method solves the problem that it is insoluble in oil from the chemical structure and the chemical property of tea-polyphenol itself, and has guaranteed the active content of phenolic hydroxyl groups of oil soluble tea polyphenol derivative on the basis of O-acidylate to greatest extent through methods such as rearrangement, reduction;
(2) the gained oil soluble tea polyphenol derivative can be dissolved in the grease with arbitrary ratio, and can keep original color of oil product and transparency, has the antioxygen freshening effect simultaneously;
(3) can prepare the oil soluble tea polyphenol derivative edible oil antioxidant of different performance by adopting different acyl chlorides and tea-polyphenol;
(4) the series unit reaction is implemented easily, and raw material sources are extensive, and cost is lower, and higher performance is arranged, and is easy to apply, and remarkable economic efficiency and social benefit are arranged.
Below by embodiment the present invention is further described in detail.
Embodiment 1 adds tea-polyphenol 100g, certain herbaceous plants with big flowers acyl chlorides 200g, tosic acid 1g in the 1000ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 100 ℃ till the system homogeneous transparent.Add the 200g aluminum chloride, heat and be stirred to and solidify, 100 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 400ml aqueous hydrochloric acid (PH＜2) and 100ml ether, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 500ml and stirred 24 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is the transparent thick liquid of light brown.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 8.3meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration P0V after 10 days.
Embodiment 2 adds tea-polyphenol 10kg, caproyl chloride 15kg, phosphatase 11 00ml in the 100L reactor that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 80 ℃ till the system homogeneous transparent.Add the 20kg aluminum chloride, heat and be stirred to and solidify, 100 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 40kg aqueous hydrochloric acid (PH＜2) and 10L ether, divide the phase of anhydrating after stirring, after sherwood oil is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 30L and stirred 5 hours, ether is washed with water to neutrality mutually, remove oil and get product, product is the light brown transparent liquid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 12.6meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 3 adds tea-polyphenol 100g, nutmeg acyl chlorides 220g, tosic acid 1.5g in the 1000ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 130 ℃ till the system homogeneous transparent.Add the 80g aluminum chloride, heat and be stirred to and solidify, 100 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 400ml aqueous hydrochloric acid (PH＜2) and 100ml ether, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 500ml and stirred 24 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is the light brown solid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 8.9meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 4 adds tea-polyphenol 100g, oleic acyl chlorides 150g, tosic acid 2g in the 1000ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 120 ℃ till the system homogeneous transparent.Add the 50g aluminum chloride, heat and be stirred to and solidify, 130 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 500ml aqueous hydrochloric acid (PH＜2) and 80ml ether, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 400ml and stirred 36 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is the sundown solid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 7.3meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 5 imports and exports tea-polyphenol 10g, linoleic acyl chlorides 20g, boron trifluoride diethyl etherate 0.5ml adding belt stirrer, thermometer, gas in the 100ml there-necked flask of mouth, logical nitrogen, stirring is also started in heating, in reacting under 80 ℃ till the system homogeneous transparent.Add the 10g aluminum chloride, heat and be stirred to and solidify, 130 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 40ml aqueous hydrochloric acid (PH＜2) and 15ml sherwood oil, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 50ml and stirred 72 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is a light brown viscous liquid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 8.7meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 6 adds tea-polyphenol 10g, caproyl chloride 10g, sulfuric acid 1ml in the 100ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 50 ℃ till the system homogeneous transparent.Add the 20g aluminum chloride, heat and be stirred to and solidify, 160 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 40ml aqueous hydrochloric acid (PH＜2) and 10ml sherwood oil, divide the phase of anhydrating after stirring, after sherwood oil is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium thiosulfate solution 50ml and stirred 12 hours, ether is washed with water to neutrality mutually, remove oil and get product, product is the light brown transparent liquid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 13.3meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 7 adds tea-polyphenol 100g, capryl(yl)chloride 200g, tosic acid 1.5g in the 1000ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 130 ℃ till the system homogeneous transparent.Add the 200g Zinc Chloride Anhydrous, heat and be stirred to and solidify, 100 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 400ml aqueous hydrochloric acid (PH＜2) and 100ml ether, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 200ml and stirred 24 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is the light brown solid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 9.8meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 8 adds tea-polyphenol 100g, stearic acid acyl chlorides 250g, tosic acid 2g in the 1000ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 120 ℃ till the system homogeneous transparent.Add the 100g Zinc Chloride Anhydrous, heat and be stirred to and solidify, 110 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 400ml aqueous hydrochloric acid (PH＜2) and 100ml ether, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 500ml and stirred 64 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is the sundown solid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 6.8meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 9 adds tea-polyphenol 100g, oleic acyl chlorides 180g, tosic acid 2g in the 1000ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 120 ℃ till the system homogeneous transparent.Add the 100g aluminum chloride, heat and be stirred to and solidify, 130 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 400ml aqueous hydrochloric acid (PH＜2) and 100ml ether, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 500ml and stirred 24 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is the sundown solid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 6.8meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 10 adds tea-polyphenol 100g, oleic acyl chlorides 180g, tosic acid 2g in the 1000ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 120 ℃ till the system homogeneous transparent.Add the 100g aluminum chloride, heat and be stirred to and solidify, 130 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 400ml aqueous hydrochloric acid (PH＜2) and 100ml ether, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 500ml and stirred 18 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is the sundown solid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 8.0meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 11 adds acyl chlorides 10g, the phosphatase 11 ml of tea-polyphenol 10g, coconut oil in the 100ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 120 ℃ till the system homogeneous transparent.Add the 20g Zinc Chloride Anhydrous, heat and be stirred to and solidify, 100 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 40ml aqueous hydrochloric acid (PH＜2) and 10ml ether, divide the phase of anhydrating after stirring, after sherwood oil is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 50ml and stirred 36 hours, ether is washed with water to neutrality mutually, remove oil and get product, product is the light brown transparent solid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 7.8meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 12 adds tea-polyphenol 100g, caproyl chloride 50g, tosic acid 0.5g in the 500ml there-necked flask that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 100 ℃ till the system homogeneous transparent.Add the 100g aluminum chloride, heat and be stirred to and solidify, 100 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 200ml aqueous hydrochloric acid (PH＜2) and 100ml ether, divide the phase of anhydrating after stirring, after ether is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 200ml and stirred 12 hours, ether is washed with water to neutrality mutually, remove ether and get product, product is the transparent thick liquid of light brown.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 8.5meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
Embodiment 13 adds tea-polyphenol 10kg, stearyl chloride 95kg, tosic acid 0.1kg in the 500L reactor that belt stirrer, thermometer, gas import and export mouthful, and logical nitrogen heats and starts stirring, in reacting under 80 ℃ till the system homogeneous transparent.Add the 30kg aluminum chloride, heat and be stirred to and solidify, 100 ℃ are incubated 1 hour in baking oven, are cooled to room temperature, add 100kg aqueous hydrochloric acid (PH＜2) and 100L ether, divide the phase of anhydrating after stirring, after sherwood oil is used aqueous hydrochloric acid (PH＜2) repetitive scrubbing 5 times mutually, add 20% sodium sulfite aqueous solution 150L and stirred 24 hours, ether is washed with water to neutrality mutually, remove oil and get product, product is the light brown transparent liquid.The commercially available hand label refining rape seed oil that adds this product of 200ppm is 11.6meq/kg (not adding this product contrast oil sample is 33.1meq/kg) at 60 ℃ of following constant temperature vibration POV after 10 days.
The invention is not restricted to the foregoing description, content of the present invention is described all can be implemented and the good effect of tool.
Claims (8)
1. preparation of oil soluble tea polyphenol derivative as edible oil antioxidant is characterized in that being made up of the following step:
(1) acylation reaction: 100 parts of (weight, back are together) tea-polyphenol, 50～500 parts of acyl chlorides, 0.05～10 part of catalyzer adding belt stirrer, thermometer, gas are imported and exported in the reactor of mouth, logical nitrogen, heating is also stirred, be warming up to and react under 50～180 ℃ till the system homogeneous transparent, be cooled to room temperature;
(2) rearrangement reaction: reset auxiliary agent with 10～400 parts and add in the reactant, heat and be stirred to and solidify, place baking oven 100～180 ℃ of insulations 0.5～5 hour again, be cooled to room temperature, add 100～1000 parts of pH＜2 acid/aqueous solution and 100～1000 parts of extraction agents again, the phase of anhydrating is divided in the back that stirs, and extraction agent is used the acid of pH＜2/aqueous solution repetitive scrubbing 5 times mutually;
(3) reduction reaction: add 50～500 parts of 20% reductive agent/aqueous solution in above-mentioned product and stirred 5～72 hours, extraction agent is washed with water to neutrality mutually, removes extraction agent and promptly makes product, and product is transparent thick liquid of light brown or light brown powder.
2. by the preparation of oil soluble tea polyphenol derivative of the described edible oil antioxidant of claim 1, it is characterized in that:
In the described acylation reaction: acyl chlorides is 80～250 parts, and catalyzer is 0.5～5 part;
In the described rearrangement reaction: resetting auxiliary agent is 80～200 parts, and acid/aqueous solution is 100～400 parts; Extraction agent is 100～200 parts;
In the described reduction reaction: 20% reductive agent/aqueous solution is 150～300 parts.
3. by the preparation of oil soluble tea polyphenol derivative of claim 1 or 2 described edible oil antioxidants, it is characterized in that: described acyl chlorides is at least a in the acyl chlorides of the acyl chlorides of valeryl chloride, caproyl chloride, oenanthyl chloro, capryl(yl)chloride, certain herbaceous plants with big flowers acyl chlorides, lauroyl chloride, nutmeg acyl chlorides, palmityl chloride, stearic acid chloride, soft ester acyl chlorides, oleic acyl chlorides, linoleic acyl chlorides, coconut oil and/or oleic acid.
4. by the preparation of oil soluble tea polyphenol derivative of claim 1 or 2 described edible oil antioxidants, it is characterized in that: described catalyzer is at least a in tosic acid, boron trifluoride diethyl etherate, sulfuric acid and/or the phosphoric acid.
5. by the preparation of oil soluble tea polyphenol derivative of claim 1 or 2 described edible oil antioxidants, it is characterized in that: described rearrangement agent is Zinc Chloride Anhydrous and/or aluminum trichloride (anhydrous).
6. by the preparation of oil soluble tea polyphenol derivative of claim 1 or 2 described edible oil antioxidants, it is characterized in that: described extraction agent is at least a in ether, sherwood oil and/or the hexanaphthene.
7. by the preparation of oil soluble tea polyphenol derivative of claim 1 or 2 described edible oil antioxidants, it is characterized in that: described reductive agent is at least a in zinc powder, the sulfurous gas aqueous solution, S-WAT, sodium bisulfite and/or the Sulfothiorine.
8. by the preparation of oil soluble tea polyphenol derivative of claim 1 or 2 described edible oil antioxidants, it is characterized in that: described acid is at least a in hydrochloric acid, sulfuric acid and/or the phosphoric acid.
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| CN103082036A (en) * | 2012-12-31 | 2013-05-08 | 浙江工业大学 | Oil-soluble bamboo leaf flavonoid derivative and application thereof |
| CN105273011A (en) * | 2014-07-11 | 2016-01-27 | 马井芳 | Preparation method for tea polyphenol oil-soluble derivative used as anti-oxidant for edible oil |
| CN106004972A (en) * | 2016-07-15 | 2016-10-12 | 昆山贝康儿童用品有限公司 | Foldable baby stroller carriage |
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| CN1197786A (en) * | 1997-11-06 | 1998-11-04 | 汪叔雄 | Oil-soluble tea polyphenol and its preparation |
| CN1231277A (en) * | 1999-01-18 | 1999-10-13 | 余姚市四明茶叶生物制品有限公司 | Fat-soluble tea polyphenol and esterfication method productive process thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1197786A (en) * | 1997-11-06 | 1998-11-04 | 汪叔雄 | Oil-soluble tea polyphenol and its preparation |
| CN1231277A (en) * | 1999-01-18 | 1999-10-13 | 余姚市四明茶叶生物制品有限公司 | Fat-soluble tea polyphenol and esterfication method productive process thereof |
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| CN101775335B (en) * | 2010-01-14 | 2012-06-20 | 云南大学 | Method for prolonging storage life of Jatropha curcas oil or fuel oil mixed by Jatropha curcas oil and petroleum diesel |
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