CN106977439A - A kind of isomerization method of lutein - Google Patents
A kind of isomerization method of lutein Download PDFInfo
- Publication number
- CN106977439A CN106977439A CN201710178784.0A CN201710178784A CN106977439A CN 106977439 A CN106977439 A CN 106977439A CN 201710178784 A CN201710178784 A CN 201710178784A CN 106977439 A CN106977439 A CN 106977439A
- Authority
- CN
- China
- Prior art keywords
- acid
- lutein
- isomerization method
- zeaxanthin
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 title claims abstract description 76
- 235000012680 lutein Nutrition 0.000 title claims abstract description 46
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 title claims abstract description 46
- 239000001656 lutein Substances 0.000 title claims abstract description 46
- 229960005375 lutein Drugs 0.000 title claims abstract description 46
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 title claims abstract description 46
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000006317 isomerization reaction Methods 0.000 title claims abstract description 20
- JKQXZKUSFCKOGQ-JLGXGRJMSA-N (3R,3'R)-beta,beta-carotene-3,3'-diol Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-JLGXGRJMSA-N 0.000 claims abstract description 30
- JKQXZKUSFCKOGQ-LQFQNGICSA-N Z-zeaxanthin Natural products C([C@H](O)CC=1C)C(C)(C)C=1C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC1=C(C)C[C@@H](O)CC1(C)C JKQXZKUSFCKOGQ-LQFQNGICSA-N 0.000 claims abstract description 30
- QOPRSMDTRDMBNK-RNUUUQFGSA-N Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCC(O)C1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C QOPRSMDTRDMBNK-RNUUUQFGSA-N 0.000 claims abstract description 30
- JKQXZKUSFCKOGQ-LOFNIBRQSA-N all-trans-Zeaxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C JKQXZKUSFCKOGQ-LOFNIBRQSA-N 0.000 claims abstract description 30
- 235000010930 zeaxanthin Nutrition 0.000 claims abstract description 30
- 239000001775 zeaxanthin Substances 0.000 claims abstract description 30
- 229940043269 zeaxanthin Drugs 0.000 claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 11
- -1 high conversion rate Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000002608 ionic liquid Substances 0.000 claims abstract description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- LFDGRWDETVOGDT-UHFFFAOYSA-N 1h-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 4
- QNZRVYCYEMYQMD-UHFFFAOYSA-N copper;pentane-2,4-dione Chemical compound [Cu].CC(=O)CC(C)=O QNZRVYCYEMYQMD-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- 235000011150 stannous chloride Nutrition 0.000 claims description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 claims description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical group [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 3
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 3
- 229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000001119 stannous chloride Substances 0.000 claims description 3
- 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 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- LRCPOJGBEQAERD-UHFFFAOYSA-M [P].[Br-].C(CCC)[P+](CCCC)(CCCC)CCCC Chemical compound [P].[Br-].C(CCC)[P+](CCCC)(CCCC)CCCC LRCPOJGBEQAERD-UHFFFAOYSA-M 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- RTQMYJXQIDQHMH-UHFFFAOYSA-N iron;propan-2-one Chemical compound [Fe].CC(C)=O RTQMYJXQIDQHMH-UHFFFAOYSA-N 0.000 claims 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 239000000047 product Substances 0.000 abstract description 7
- 239000012043 crude product Substances 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 description 5
- 238000004040 coloring Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 150000002658 luteins Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKUSWAGOKUGEDX-UHFFFAOYSA-N C(CCC)Br(CCCC)(CCCC)CCCC Chemical compound C(CCC)Br(CCCC)(CCCC)CCCC OKUSWAGOKUGEDX-UHFFFAOYSA-N 0.000 description 1
- 235000005881 Calendula officinalis Nutrition 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 240000000785 Tagetes erecta Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- DPSGOVRFPJKNRW-UHFFFAOYSA-N [Br-].C(C)[PH2+]CCCC Chemical compound [Br-].C(C)[PH2+]CCCC DPSGOVRFPJKNRW-UHFFFAOYSA-N 0.000 description 1
- AHIBWURJLGCHAY-UHFFFAOYSA-N [S].C1=CC=CC=C1 Chemical compound [S].C1=CC=CC=C1 AHIBWURJLGCHAY-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of isomerization method of lutein, comprise the following steps：Lutein is scattered in a solvent, acid or/and ionic liquid are added, metal salt catalyst is added, catalytic reaction is carried out, obtains zeaxanthin.The isomerization method of the present invention can obtain high content zeaxanthin, high conversion rate, product purity is high, and crude product Lutein content can be down to less than 8%, zeaxanthin is converted into zeaxanthin up to more than 80%, for lutein and provides a kind of economically viable process route.
Description
Technical field
The present invention relates to a kind of isomerization method of lutein.
Background technology
Lutein is a member in carotenoid family, is widely present in the natural plants such as marigold, banana and corn and works as
In.In nature, lutein and zeaxanthin typically exist jointly, and they are widely used in the yolk of poultry, skin and subcutaneous
Skin and the meat coloring of fat coloring, fish and shellfish, used also as food additives.Research shows, maize
Confrontation yellow deposition is more sensitive, and more preferably, application prospect is more preferable, but the content of zeaxanthin will be much in natural plants for coloring effect
Less than lutein.
It is well known that isomerization reaction occurs under strong base catalyst for lutein can generate zeaxanthin.PCT Publication
Described in WO96/02594 and lutein isomer is melted into zeaxanthin in strong alkali solution under conditions of a kind of temperature-control pressure-control
Method, inorganic base used is alkali metal hydroxide, calcium hydroxide, sodium carbonate or ammonium hydroxide, and organic base is ethamine, second
Hydramine or morpholine, only with water as solvent, the conversion ratio of this method Lutein is very low, and only only 10%~20%.
Therefore, it is necessary to develop a kind of new lutein isomer method.
The content of the invention
It is an object of the invention to provide a kind of isomerization method of lutein.
The technical solution used in the present invention is：
A kind of isomerization method of lutein, comprises the following steps：Lutein is scattered in a solvent, add acid or/and ion
Liquid, adds metal salt catalyst, carries out catalytic reaction, obtains zeaxanthin.
Described solvent is n-hexane, dichloromethane, hexamethylene, petroleum ether, ethyl acetate, acetone, benzene, toluene, diformazan
At least one of benzene, methanol, ethanol, water.
Described lutein, the mass volume ratio of solvent are 1g：（10~30）mL.
Described acid is at least one of organic acid, inorganic acid, and addition is the 0.1%~5% of lutein quality.
Described organic acid is in formic acid, acetic acid, propionic acid, ethanedioic acid, p-methyl benzenesulfonic acid, trifluoromethanesulfonic acid, benzene sulfonic acid
At least one, described inorganic acid is at least one of sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, perchloric acid, hydrobromic acid, hydroiodic acid.
Described ionic liquid is pyrrole hydrochloride, trimethylamine hydrochloride, triethylamine hydrochloride, tetrabutyl phosphonium bromide phosphorus, three
At least one of butyl ethyl phosphonium bromide, N- hexyl pyridines hexafluorophosphate, N- hexyl pyridinium tetrafluoroborate salt, addition is
The 0.1%~5% of lutein quality.
Described metal salt catalyst is at least one of Cu-series catalyst, Fe-series catalyst, and addition is lutein
The 0.05%~1% of quality.
Described Cu-series catalyst is acetylacetone copper, copper sulphate, copper acetate, cuprous iodide, stannous chloride, cuprous bromide
At least one of.
Described Fe-series catalyst is at least one of iron chloride, ferric acetyl acetonade, carbonyl iron, ferric sulfate.
Described catalytic reaction is carried out at 30 DEG C~80 DEG C, and the reaction time is 5~12 hours.
The beneficial effects of the invention are as follows：The isomerization method of the present invention can obtain high content zeaxanthin, high conversion rate,
Product purity is high, and the crude product Lutein content prepared can be down to less than 8%, zeaxanthin up to more than 80%,
Zeaxanthin, which is converted into, for lutein provides a kind of economically viable process route.
Embodiment
A kind of isomerization method of lutein, comprises the following steps：Lutein is scattered in a solvent, add acid or/and
Ionic liquid, adds metal salt catalyst, carries out catalytic reaction, obtains zeaxanthin.
It is preferred that, described solvent is n-hexane, dichloromethane, hexamethylene, petroleum ether, ethyl acetate, acetone, benzene, first
At least one of benzene, dimethylbenzene, methanol, ethanol, water.
It is preferred that, described lutein, the mass volume ratio of solvent are 1g：（10~30）mL.
It is preferred that, described acid is at least one of organic acid, inorganic acid, addition for lutein quality 0.1%~
5%。
It is preferred that, described organic acid is formic acid, acetic acid, propionic acid, ethanedioic acid, p-methyl benzenesulfonic acid, trifluoromethanesulfonic acid, benzene sulphur
At least one of acid, described inorganic acid be in sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid, perchloric acid, hydrobromic acid, hydroiodic acid at least
It is a kind of.
It is preferred that, described ionic liquid is pyrrole hydrochloride, trimethylamine hydrochloride, triethylamine hydrochloride, tetrabutyl bromine
Change at least one of phosphorus, tributyl ethyl phosphonium bromide phosphorus, N- hexyl pyridines hexafluorophosphate, N- hexyl pyridinium tetrafluoroborate salt,
Addition is the 0.1%~5% of lutein quality.
It is preferred that, described metal salt catalyst is at least one of Cu-series catalyst, Fe-series catalyst, and addition is
The 0.05%~1% of lutein quality.
It is preferred that, described Cu-series catalyst is acetylacetone copper, copper sulphate, copper acetate, cuprous iodide, stannous chloride,
At least one of cuprous bromide.
It is preferred that, described Fe-series catalyst is at least one of iron chloride, ferric acetyl acetonade, carbonyl iron, ferric sulfate.
It is preferred that, described catalytic reaction is carried out at 30 DEG C~80 DEG C, and the reaction time is 5~12 hours.
The present invention is made further explanation and description with reference to specific embodiment.
Embodiment 1：
10g lutein is dissolved in 200mL petroleum ethers, 0.01g pyrrole hydrochlorides is added, adds 0.005g acetylacetone coppers, is risen
Temperature is to 60 DEG C, and stirring reaction 8 hours obtains high content zeaxanthin.
After tested, the high content zeaxanthin product Lutein content is 7.2%, and zeaxanthin is 88.3%.
Embodiment 2：
10g lutein is dissolved in the mixed solution that 200mL n-hexanes and 100mL water are constituted, 0.1g acetic acid is added, adds
0.05g stannous chlorides, are warming up to 68 DEG C, stirring reaction 10 hours obtains high content zeaxanthin.
After tested, the high content zeaxanthin product Lutein content is 12%, and zeaxanthin is 84.5%.
Embodiment 3：
10g lutein is dissolved in 150mL dichloromethane, 0.5g propionic acid is added, adds 0.1g copper sulphate, be warming up to 30 DEG C, stir
Reaction 12 hours is mixed, high content zeaxanthin is obtained.
After tested, the high content zeaxanthin product Lutein content is 19.4%, and zeaxanthin is 78%.
Embodiment 4：
10g lutein is dissolved in 100mL petroleum ethers, 0.2g phosphoric acid is added, adds 0.05g ferric acetyl acetonades, be warming up to 80 DEG C,
Stirring reaction 12 hours, obtains high content zeaxanthin.
After tested, the high content zeaxanthin product Lutein content is 20%, and zeaxanthin is 76.5%.
Embodiment 5：
10g lutein is dissolved in 100mL petroleum ethers, 0.1g triethylamine hydrochlorides is added, adds 0.05g ferric acetyl acetonades, is risen
Temperature is to 78 DEG C, and stirring reaction 5 hours obtains high content zeaxanthin.
After tested, the high content zeaxanthin product Lutein content is 7.8%, and zeaxanthin is 89.5%.
Note：Lutein in embodiment 1~5 is the method purifying that commercially available lutein is provided according to patent US5780693
, wherein lutein content is 93%, and zeaxanthin is 6.1%.
Above-described embodiment is preferably embodiment, but embodiments of the present invention are not by above-described embodiment of the invention
Limitation, other any Spirit Essences without departing from the present invention and the change made under principle, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (10)
1. a kind of isomerization method of lutein, it is characterised in that：Comprise the following steps：Lutein is scattered in a solvent, plus
Enter acid or/and ionic liquid, add metal salt catalyst, carry out catalytic reaction, obtain zeaxanthin.
2. isomerization method according to claim 1, it is characterised in that：Described solvent is n-hexane, dichloromethane, ring
At least one of hexane, petroleum ether, ethyl acetate, acetone, benzene,toluene,xylene, methanol, ethanol, water.
3. isomerization method according to claim 1, it is characterised in that：Described lutein, the mass volume ratio of solvent
For 1g：（10~30）mL.
4. isomerization method according to claim 1, it is characterised in that：Described acid be organic acid, inorganic acid in extremely
Few one kind, addition is the 0.1%~5% of lutein quality.
5. isomerization method according to claim 4, it is characterised in that：Described organic acid be formic acid, acetic acid, propionic acid,
At least one of ethanedioic acid, p-methyl benzenesulfonic acid, trifluoromethanesulfonic acid, benzene sulfonic acid, described inorganic acid is sulfuric acid, hydrochloric acid, phosphoric acid,
At least one of nitric acid, perchloric acid, hydrobromic acid, hydroiodic acid.
6. isomerization method according to claim 1, it is characterised in that：Described ionic liquid is pyrrole hydrochloride, three
Methylamine hydrochloride, triethylamine hydrochloride, tetrabutyl phosphonium bromide phosphorus, tributyl ethyl phosphonium bromide phosphorus, N- hexyl pyridines hexafluorophosphate, N-
At least one of hexyl pyridinium tetrafluoroborate salt, addition is the 0.1%~5% of lutein quality.
7. isomerization method according to claim 1, it is characterised in that：Described metal salt catalyst is catalyzed for copper system
At least one of agent, Fe-series catalyst, addition are the 0.05%~1% of lutein quality.
8. isomerization method according to claim 7, it is characterised in that：Described Cu-series catalyst be acetylacetone copper,
At least one of copper sulphate, copper acetate, cuprous iodide, stannous chloride, cuprous bromide.
9. isomerization method according to claim 7, it is characterised in that：Described Fe-series catalyst is iron chloride, acetyl
At least one of acetone iron, carbonyl iron, ferric sulfate.
10. isomerization method according to claim 1, it is characterised in that：Described catalytic reaction is at 30 DEG C~80 DEG C
Carry out, the reaction time is 5~12 hours.
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| CN108586306A (en) * | 2018-05-23 | 2018-09-28 | 华东理工大学 | A method of lutein and zeaxanthin are detached using ionic liquid strengthening extraction |
| CN110143904A (en) * | 2019-06-26 | 2019-08-20 | 班磊 | A kind of preparation method of semi-synthetic astaxanthin intermediate zeaxanthin |
| CN117483002A (en) * | 2023-11-01 | 2024-02-02 | 西安岳达生物科技股份有限公司 | Catalyst composition, preparation method of zeaxanthin ester and zeaxanthin ester |
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| CN110143904A (en) * | 2019-06-26 | 2019-08-20 | 班磊 | A kind of preparation method of semi-synthetic astaxanthin intermediate zeaxanthin |
| CN110143904B (en) * | 2019-06-26 | 2021-07-27 | 班磊 | Preparation method of zeaxanthin as intermediate of semi-synthetic astaxanthin |
| CN117483002A (en) * | 2023-11-01 | 2024-02-02 | 西安岳达生物科技股份有限公司 | Catalyst composition, preparation method of zeaxanthin ester and zeaxanthin ester |
| CN117483002B (en) * | 2023-11-01 | 2026-01-30 | 西安岳达生物科技股份有限公司 | Catalyst composition, preparation method of zeaxanthin ester and zeaxanthin ester |
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Denomination of invention: Isomerization method of xanthophyll Effective date of registration: 20200107 Granted publication date: 20181002 Pledgee: Bank of China, Limited by Share Ltd, Guangzhou, Panyu branch Pledgor: Guangzhou Wisdom Bio-Technology Co., Ltd. Registration number: Y2020440000002 |
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