CN101979377B - Method for saponifying lutein grease - Google Patents
Method for saponifying lutein grease Download PDFInfo
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- CN101979377B CN101979377B CN 201010290052 CN201010290052A CN101979377B CN 101979377 B CN101979377 B CN 101979377B CN 201010290052 CN201010290052 CN 201010290052 CN 201010290052 A CN201010290052 A CN 201010290052A CN 101979377 B CN101979377 B CN 101979377B
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- saponification
- xenthophylls
- grease
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- reaction
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- 239000004519 grease Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 21
- 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 abstract description 30
- 235000012680 lutein Nutrition 0.000 title abstract description 21
- 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 abstract description 21
- 239000001656 lutein Substances 0.000 title abstract description 21
- 229960005375 lutein Drugs 0.000 title abstract description 21
- 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 abstract description 21
- 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 abstract description 21
- 238000007127 saponification reaction Methods 0.000 claims abstract description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 17
- 241000282326 Felis catus Species 0.000 claims description 17
- 230000031709 bromination Effects 0.000 claims description 12
- 238000005893 bromination reaction Methods 0.000 claims description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 10
- -1 triethyl tertiary butyl Chemical group 0.000 claims description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 6
- 238000005660 chlorination reaction Methods 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 abstract description 5
- 239000003945 anionic surfactant Substances 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000004945 emulsification Methods 0.000 abstract description 2
- 239000003093 cationic surfactant Substances 0.000 abstract 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 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 description 9
- 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 description 9
- 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 description 9
- 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 description 9
- 235000010930 zeaxanthin Nutrition 0.000 description 9
- 239000001775 zeaxanthin Substances 0.000 description 9
- 229940043269 zeaxanthin Drugs 0.000 description 9
- 239000003643 water by type Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 4
- 240000000785 Tagetes erecta Species 0.000 description 3
- 235000012311 Tagetes erecta Nutrition 0.000 description 3
- 235000003595 Tagetes minuta Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Abstract
The invention discloses a method for saponifying lutein grease, which comprises the following steps of: mixing the lutein grease, water and a strong base, and adding a cationic surfactant before or during saponification reaction. Therefore, an anionic surfactant palmitate generated in the saponification reaction process is unexpectedly deactivated, reaction solution does not get viscous and still has relatively higher liquidity, the saponification reaction can be more quickly and completely performed, and ordinarily can be finished after 7 to 8 hours, and the extent of the reaction is as high as 85 to 99 percent. In the method, by controlling the amount of the cationic surfactant, the reaction solution obtained by the reaction has a certain emulsification effect, can be directly sprayed and dried, effectively reduces energy consumption and saves the production cost.
Description
Technical field
The present invention relates to a kind of method for saponification of xenthophylls grease.
Background technology
Xenthophylls is to belong to carotenoid, extensively is present in the plants such as vegetables, flowers, fruit, and in Flower of Aztec Marigold, content is very high especially, and institute's xenthophylls of selling mostly obtains for extracting after saponification in Flower of Aztec Marigold in the market.The Flower of Aztec Marigold Lutein mainly exists with its palmitinic acid diester form.
The method for saponification of xenthophylls grease has a variety of.Traditional method for saponification is that the xenthophylls grease is heated to 60～80 ℃ in buck, and saponification obtains the monomer (lutein and a small amount of zeaxanthin) of xenthophylls.The palmitate generated due to this saponification reaction is a kind of anion surfactant, and continuous emulsion reaction liquid makes the reaction solution very thickness that becomes, and directly affects the speed of saponification reaction, causes the saponification time elongation, and impurity increases, and saponification is incomplete.The method for saponification of traditional xenthophylls grease, its saponification time reaches 12～24 hours, and the degree of saponification reaction only has 70～80%.In order to overcome this shortcoming, US5648564, CN1436774, CN1463966, CN 1603308, in the disclosed technology such as CN101168522, carry out the saponification of xenthophylls grease in lower aliphatic alcohols, avoid producing palmitate, thereby make reaction carry out more smoothly; Also have in water and a large amount of organic solvent and react saponification, the palmitate generated with a large amount of organic solvent dilutings.And, in fodder industry, directly carry out spray agent after requiring the xenthophylls saponification to complete.Therefore in organic solvent, the product of saponification also needs to remove organic solvent, then adds thinner and emulsifying agent carries out emulsification, spray agent.So not only can make energy consumption increase, also virtually extend production sequence, more seriously likely cause in product existing organic residue, affect the security of product.
Summary of the invention
The purpose of this invention is to provide a kind of method of carrying out smoothly the saponification of xenthophylls grease in water-poor phase.
The technical solution used in the present invention is:
A kind of method for saponification of xenthophylls grease, comprise xenthophylls grease, water mixing, highly basic and cats product mixed, and heats afterwards saponification and get final product.
A kind of method for saponification of xenthophylls grease comprises xenthophylls grease, water is mixed and the highly basic mixing that the heating saponification, add cats product in the process of saponification.
Preferably, the add-on of water is 30～50% of xenthophylls oil quality.
Highly basic is at least one in NaOH, KOH, and preferred, the add-on of highly basic is 11～13% of xenthophylls oil quality.
Cats product is preferably brometo de amonio type cats product, be preferably at least one in Tetrabutyl amonium bromide, tetrabutylammonium chloride, trimethylammonium tertiary butyl bromination ammonium, trimethylammonium tertiary butyl chlorination ammonium, dimethyl diethyl brometo de amonio, triethyl tertiary butyl bromination ammonium, the add-on of cats product is preferably 1.5～2.5% of xenthophylls oil quality.
The inventive method by adding cats product in reactant, brometo de amonio type cats product particularly, unexpectedly can make the anion surfactant palmitate inactivation generated in the saponification reaction process, the reaction solution thickness that can not become, mobility is still better, make saponification reaction can be more fast, carry out more completely, generally at 7～8 hours, can complete saponification reaction, level of response is up to 85～99%.By controlling the amount of cats product, the reaction solution after can making to have reacted has certain emulsifying effectiveness, can directly carry out spraying drying, has effectively reduced energy consumption, has saved production cost.
Embodiment
A kind of method for saponification of xenthophylls grease, comprise xenthophylls grease, water mixing, highly basic and cats product mixed, and heats afterwards saponification and get final product.
A kind of method for saponification of xenthophylls grease comprises xenthophylls grease, water is mixed and the highly basic mixing that the heating saponification, add cats product in the process of saponification.
Preferably, the add-on of water is 30～50% of xenthophylls oil quality.As those skilled in the art's basic general knowledge, also can reasonably regulate the add-on of water.
Highly basic is at least one in NaOH, KOH, and preferred, the add-on of highly basic is 11～13% of xenthophylls oil quality.As those skilled in the art's basic general knowledge, also can reasonably regulate the add-on of highly basic, and mix and use different highly basic.
Cats product is preferably brometo de amonio type cats product, be preferably at least one in Tetrabutyl amonium bromide, tetrabutylammonium chloride, trimethylammonium tertiary butyl bromination ammonium, trimethylammonium tertiary butyl chlorination ammonium, dimethyl diethyl brometo de amonio, triethyl tertiary butyl bromination ammonium, the add-on of cats product is preferably 1.5～2.5% of xenthophylls oil quality.Those skilled in the art, also can as the case may be, carry out suitable adjustment to its add-on.
Below in conjunction with embodiment, further illustrate the present invention.
Embodiment 1
Get the xenthophylls grease of 100 grams, add the KOH of 30 gram deionized waters and 11 grams, the Tetrabutyl amonium bromide of 1.5 grams, be heated to 80 ℃ of reactions 7 hours, and total lutein content is 93.3% (HPLC), and lutein accounts for 88.5%, and zeaxanthin accounts for 4.8%.The also not saponification of grease of surplus 0.7% (HPLC).
Embodiment 2
Get the xenthophylls grease of 100 grams, add the NaOH of 50 gram deionized waters and 13 grams, the trimethylammonium tertiary butyl bromination ammonium of 2.5 grams, be heated to 60 ℃ of reactions 8 hours, and total lutein content is 93.0% (HPLC), and lutein accounts for 88.2%, and zeaxanthin accounts for 4.8%.The also not saponification of grease of surplus 1% (HPLC).
Embodiment 3
Get the xenthophylls grease of 100 grams, add the NaOH of 30 gram deionized waters and 11 grams, the tetrabutylammonium chloride of 1.5 grams, be heated to 80 ℃ of reactions 7 hours, and total lutein content is 80.3% (HPLC), and lutein accounts for 75.8%, and zeaxanthin accounts for 4.5%.The also not saponification of grease of surplus 13.7% (HPLC).
Embodiment 4
Get 100 gram xenthophylls greases, add the KOH of 40 gram deionized waters and 13 grams, the trimethylammonium tertiary butyl chlorination ammonium of 2 grams, be heated to 70 ℃ of reactions 7 hours, and total lutein content is 81.3% (HPLC), and lutein accounts for 76.9%, and zeaxanthin accounts for 4.4%.The also not saponification of grease of surplus 12.7% (HPLC).
Embodiment 5
Get the xenthophylls grease of 100 grams, add the KOH of 30 gram deionized waters and 12 grams, the dimethyl diethyl brometo de amonio of 1.5 grams, be heated to 80 ℃ of reactions 7 hours, and total lutein content is 82.5% (HPLC), and lutein accounts for 78.5%, and zeaxanthin accounts for 4.0%.The also not saponification of grease of surplus 12.5% (HPLC).
Embodiment 6
Get the xenthophylls grease of 100 grams, add the KOH of 30 gram deionized waters and 12 grams, the triethyl tertiary butyl bromination ammonium of 2 grams, be heated to 60 ℃ of reactions 7 hours, and total lutein content is 85.5% (HPLC), and lutein accounts for 80.5%, and zeaxanthin accounts for 5.0%.The also not saponification of grease of surplus 8.5% (HPLC).
Embodiment 7
Get the xenthophylls grease of 100 grams, add 35 gram deionized waters and 7 gram KOH, 5 gram NaOH, be heated to 65 ℃ and carry out saponification reaction, add 1 gram triethyl tertiary butyl bromination ammonium, 1 gram dimethyl diethyl brometo de amonio in reaction process, saponification finishes reaction after 7 hours.Total lutein content is 93.6% (HPLC), and lutein accounts for 89.6%, and zeaxanthin accounts for 4%.The also not saponification of grease of surplus 0.4% (HPLC).
Embodiment 8
Get the xenthophylls grease of 100 grams, add 35 gram deionized waters and 5 gram KOH, 8 gram NaOH, be heated to 75 ℃ and carry out saponification reaction, add 0.5 gram triethyl tertiary butyl bromination ammonium, 1 gram dimethyl diethyl brometo de amonio, 0.5 gram Tetrabutyl amonium bromide in reaction process, saponification finishes reaction after 7.5 hours.Total lutein content is 92.5% (HPLC), and lutein accounts for 88%, and zeaxanthin accounts for 4.5%.The also not saponification of grease of surplus 1.6% (HPLC).
Claims (2)
1. the method for saponification of an xenthophylls grease, mix xenthophylls grease, water, highly basic and cats product, and heat afterwards saponification and get final product, wherein,
The add-on of water is 30～50% of xenthophylls oil quality;
Highly basic is at least one in NaOH, KOH, and add-on is 11～13% of xenthophylls oil quality;
Cats product is at least one in Tetrabutyl amonium bromide, tetrabutylammonium chloride, trimethylammonium tertiary butyl bromination ammonium, trimethylammonium tertiary butyl chlorination ammonium, dimethyl diethyl brometo de amonio, triethyl tertiary butyl bromination ammonium, and add-on is 1.5～2.5% of xenthophylls oil quality;
The temperature of saponification is 60～80 ℃.
2. the method for saponification of an xenthophylls grease, mix xenthophylls grease, water and highly basic, and the heating saponification is added cats product in the process of saponification; Wherein,
The add-on of water is 30～50% of xenthophylls oil quality;
Highly basic is at least one in NaOH, KOH, and add-on is 11～13% of xenthophylls oil quality;
Cats product is at least one in Tetrabutyl amonium bromide, tetrabutylammonium chloride, trimethylammonium tertiary butyl bromination ammonium, trimethylammonium tertiary butyl chlorination ammonium, dimethyl diethyl brometo de amonio, triethyl tertiary butyl bromination ammonium, and add-on is 1.5～2.5% of xenthophylls oil quality;
The temperature of saponification is 60～80 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010290052 CN101979377B (en) | 2010-09-20 | 2010-09-20 | Method for saponifying lutein grease |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010290052 CN101979377B (en) | 2010-09-20 | 2010-09-20 | Method for saponifying lutein grease |
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| Publication Number | Publication Date |
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| CN101979377A CN101979377A (en) | 2011-02-23 |
| CN101979377B true CN101979377B (en) | 2013-12-25 |
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Families Citing this family (2)
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| CN108813616A (en) * | 2018-07-05 | 2018-11-16 | 河北东之星生物科技股份有限公司 | A method of preparing lutein water-soluble microemulsion |
| CN111068621B (en) * | 2019-12-10 | 2022-12-20 | 大连工业大学 | Fe 3 O 4 Preparation method and application of @ DA/GO magnetic nanoparticles |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1723799A (en) * | 2005-07-21 | 2006-01-25 | 青岛赛特香料有限公司 | Method for preparing food additives-xanthophyll made from xanthophyll resin |
| CN101130512A (en) * | 2007-08-31 | 2008-02-27 | 陕西天润植物化工有限公司 | Method for producing xanthophyll |
| CN101139312A (en) * | 2007-05-08 | 2008-03-12 | 陈吉华 | Method for preparing free lutein having high saponification ratio |
| CN101514177A (en) * | 2009-03-13 | 2009-08-26 | 沈阳药科大学 | Method for extracting lutein from marigold particles |
-
2010
- 2010-09-20 CN CN 201010290052 patent/CN101979377B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1723799A (en) * | 2005-07-21 | 2006-01-25 | 青岛赛特香料有限公司 | Method for preparing food additives-xanthophyll made from xanthophyll resin |
| CN101139312A (en) * | 2007-05-08 | 2008-03-12 | 陈吉华 | Method for preparing free lutein having high saponification ratio |
| CN101130512A (en) * | 2007-08-31 | 2008-02-27 | 陕西天润植物化工有限公司 | Method for producing xanthophyll |
| CN101514177A (en) * | 2009-03-13 | 2009-08-26 | 沈阳药科大学 | Method for extracting lutein from marigold particles |
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