CN101774957B - Process for synthesizing beta-carotene - Google Patents
Process for synthesizing beta-carotene Download PDFInfo
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- CN101774957B CN101774957B CN 201010104562 CN201010104562A CN101774957B CN 101774957 B CN101774957 B CN 101774957B CN 201010104562 CN201010104562 CN 201010104562 CN 201010104562 A CN201010104562 A CN 201010104562A CN 101774957 B CN101774957 B CN 101774957B
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- 238000000034 method Methods 0.000 title claims abstract description 18
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(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)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 title abstract description 7
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene 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=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 title abstract description 7
- 235000013734 beta-carotene Nutrition 0.000 title abstract description 7
- 239000011648 beta-carotene Substances 0.000 title abstract description 7
- 229960002747 betacarotene Drugs 0.000 title abstract description 7
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(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\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 title abstract description 7
- 230000002194 synthesizing effect Effects 0.000 title abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims description 25
- -1 carbon SULPHOSUCCINIC ACID ESTERs Chemical class 0.000 claims description 10
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 8
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N penta-1,3-diene Chemical compound CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- 150000001340 alkali metals Chemical class 0.000 claims 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229940043279 diisopropylamine Drugs 0.000 claims 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000012530 fluid Substances 0.000 abstract 3
- AYODHZHFDRRQEZ-UHFFFAOYSA-N 2,7-dimethylocta-2,4,6-trienedial Chemical compound O=CC(C)=CC=CC=C(C)C=O AYODHZHFDRRQEZ-UHFFFAOYSA-N 0.000 abstract 1
- CTVCHHZNFHCCNP-UHFFFAOYSA-K [C+4].[C+4].[C+4].[C+4].[C+4].CC=CC=C.[O-]P([O-])([O-])=O Chemical compound [C+4].[C+4].[C+4].[C+4].[C+4].CC=CC=C.[O-]P([O-])([O-])=O CTVCHHZNFHCCNP-UHFFFAOYSA-K 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 229940045997 vitamin a Drugs 0.000 description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 235000019155 vitamin A Nutrition 0.000 description 2
- 239000011719 vitamin A Substances 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a process for synthesizing beta-carotene, comprising the following steps: mixing 5-10% of organic secondary amine by volume, 10-15% of organic alkane by volume and 75-85% of methanol by volume or ethanol to obtain reaction push fluid; dissolving 2,4-pentadiene pentacarbon phosphate and 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde in the reaction push fluid according to the molar ratio of 2-2.2:1; and preserving the reaction temperature to be negative 10-0 DEG C and adding alkali compound in the reaction push fluid of the last step for reacting so as to obtain the beta-carotene. The process for synthesizing the beta-carotene has the advantages that the yield of the beta-carotene is high, reaching 85%, the used raw materials are cheaper, the synthesis cost is low, the posttreatment is simple, the solvent can be recovered and used, and the production operation is convenient.
Description
Technical field
The present invention relates to a kind of organic synthesis technique, particularly a kind of synthesis technique of β-Hu Luobusu.
Background technology
β-Hu Luobusu (β-Carotene), be a kind of important non-vitamin a source carrotenoid, also be a kind of inhibitor, have detoxification, be to safeguard the indispensable nutrient substance of HUMAN HEALTH.β-Hu Luobusu anticancer, preventing cardiovascular disease, cataract and anti-oxidant on remarkable function is arranged, can also prevent by the aging and old and feeble multiple degenerative disorders that causes, of many uses.
Chemosynthesis Recent study for β-Hu Luobusu is continuous always, and domestic production mainly is starting raw material with the vitamin A, and is synthetic for it, Lu Yu, clock sturdy pines, Chen Baoren; " synthesizing of β-Hu Luobusu "; University Of Nanchang's journal (version of science); The 19th rolls up the May nineteen ninety-five third phase; Zhou Yunjiu, Wang Fengyun, Jiang Yujuan, Sun Changan, " β-Hu Luobusu study on the synthesis "; The Heilungkiang medical science; The 21st rolls up in August, 1998 the 4th phase; Marvin's is prosperous, Hu Siping, Chen Chunfeng, Bai Yalong, Shen Runbo, " oxidative coupling prepares β-Hu Luobusu "; Chinese Journal of Pharmaceuticals; 2008 the 39th the 3rd phases of volume, wait and done play-by-play.Because it is starting raw material that this route is used expensive vitamin A, production cost is very high.
Germany BASF AG adopts the synthetic β-Hu Luobusu of 2C15+C10, and is specific as follows:
This route produces a by product triphenylphosphinc oxide, and triphenylphosphinc oxide is water insoluble, mixes with product, is difficult to handle, and recycle and need use phosgene, if not reclaiming the triphenylphosphinc oxide cost can significantly increase, production is restricted at home.
US4916250 has reported another route, and is specific as follows:
Summary of the invention
In order to overcome the problems referred to above, the present invention provides a kind of synthesizing technique for beta-carotene of high yield.
The technical scheme that the present invention taked is:
A kind of synthesis technique of β-Hu Luobusu may further comprise the steps:
1) be that organic secondary amine of 5～10%, organic alkane of 10～15%, 75～85% methyl alcohol or ethanol mix and obtains reaction and promote liquid with volume percent;
2) by 2～2.2: 1 mol ratio, with 2,4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs and 2,7-dimethyl--2,4,6-sarohornene-1,8-dialdehyde are dissolved in reaction and promote in the liquid;
3) keep temperature of reaction at-10～0 ℃, in the reaction promotion liquid of a last step, add basic cpd, reaction obtains β-Hu Luobusu.
Preferably, the carbonatoms of organic alkane is 5～8.
Preferably, 2, the mol ratio of 4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs and basic cpd is 1: 1～1: 2.
Preferably, 2,7-dimethyl--2,4,6-sarohornene-1, the 8-dialdehyde promotes that with reaction the mass volume ratio of liquid is 8～15: 100.
The yield of this synthesis technique β-Hu Luobusu is high, can reach 85%, and the raw material of selecting for use is comparatively cheap, and synthetic cost is low; Aftertreatment is simple, and solvent can recovery set usefulness, operation convenient for production.
Description of drawings
Fig. 1 is embodiment 1 a finished product β-Hu Luobusu
1The H-NMR spectrogram.
Embodiment
Below in conjunction with instance, further specify the present invention.
Embodiment 1
1) with 5 milliliters of diethylamine, 10 milliliters of hexanes, 85 milliliters methanol mixed, obtains reaction and promote liquid;
2) with content be 95% 2,2 of 4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs 35.8 grams (0.1 mole), 8.2 grams (0.05 mole), 7-dimethyl--2,4,6-sarohornene-1,8-dialdehyde are dissolved in reaction and promote in the liquid;
3) be cooled to 0 ℃, the sodium tert-butoxide of 11.5 grams (0.12 mole) divided add reaction for three times and promote in the liquid, each 10 minutes at interval, add continued reaction 5 hours, filtration drying then, the β-Hu Luobusu yield is about 85%.
Embodiment 2
1) with 8 milliliters of methylethyl amine, 15 milliliters of heptane, 77 milliliters methanol mixed, obtains reaction and promote liquid;
2) with content be 95% 2,2 of 4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs 35.8 grams (0.1 mole), 8.2 grams (0.05 mole), 7-dimethyl--2,4,6-sarohornene-1,8-dialdehyde are dissolved in reaction and promote in the liquid;
3) be cooled to-2 ℃, 6.5 gram (0.12 mole) sodium methylates divided add reaction for three times and promote in the liquid, each 10 minutes at interval, add continued reaction 4.5 hours, filtration drying then, the β-Hu Luobusu yield is about 74%.
Embodiment 3
1) with 7 milliliters of methylethyl amine, 11 milliliters of heptane, 82 milliliters methanol mixed, obtains reaction and promote liquid;
2) with content be 95% 2,2 of 4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs 39.4 grams (0.11 mole), 8.2 grams (0.05 mole), 7-dimethyl--2,4,6-sarohornene-1,8-dialdehyde are dissolved in reaction and promote in the liquid;
3) be cooled to-4 ℃, 8.8 gram (0.22 mole) sodium hydroxide divided add reaction for three times and promote in the liquid, each 10 minutes at interval, add continued reaction 5 hours, filtration drying then, the β-Hu Luobusu yield is about 60%.
Embodiment 4
1) 10 milliliters of methylethyl amine, 15 milliliters of heptane, 75 milliliters ethanol are mixed, obtain reaction and promote liquid;
2) with content be 95% 2,2 of 4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs 35.8 grams (0.1 mole), 8.2 grams (0.05 mole), 7-dimethyl--2,4,6-sarohornene-1,8-dialdehyde are dissolved in reaction and promote in the liquid;
3) be cooled to-8 ℃, the sodium hydroxide of 4 grams (0.1 mole) and 1.08 gram (0.02 mole) sodium methylates divided add reaction for three times and promote in the liquid, each 10 minutes at interval, add continued reaction 4 hours, filtration drying then, the β-Hu Luobusu yield is about 70%.
1) with 8 milliliters of diisopropylamines, 10 milliliters of pentanes, 82 milliliters methanol mixed, obtains reaction and promote liquid;
2) with content be 95% 2,2 of 4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs 71.6 grams (0.2 mole), 15 grams (0.09 mole), 7-dimethyl--2,4,6-sarohornene-1,8-dialdehyde are dissolved in reaction and promote in the liquid;
3) be cooled to-10 ℃, 4.8 gram (0.2 mole) sodium hydrides divided add reaction for three times and promote in the liquid, each 10 minutes at interval, add continued reaction 5 hours, filtration drying then, the β-Hu Luobusu yield is about 76%.
In this synthesis technique, reaction promotes the effect of liquid to be to build a kind of reaction environment, puies forward highly basic solubleness as much as possible, makes reactant in this kind environment, suppress production of by-products, increases the output of kind of product, thereby reaches the purpose that improves yield.
The effect of basic cpd is to make reactant to produce carbanion, and the Wittig-Horner reaction takes place.The alkalescence of basic cpd is strong more, promotes that in reaction the solubleness in the liquid is big more, and it is good more to react.After adding alkali, temperature of reaction system can violent raise, for control reaction temperature in the scope that requires, alkali is criticized adding.Be that branch adds for 3 times among the embodiment, but and do not mean that other adding mode in batches is inadvisable.
Fig. 1 is embodiment 1 finished product
1The H-NMR spectrogram, its hydrogen spectrum belongs to as follows:
1H-NMR：(CDCl
3)：
6.6733～6.6203(4H，m)，6.3678～6.2415(2H，d)，
6.1590～6.1126(6H，m)，2.0193(4H，s)，1.9715
(12H，s)，1.7182(6H，s)，1.6149～1.4663(4H，d)
1.0290 (12H s), is characterized by β-Hu Luobusu.
Claims (7)
1. the synthesis technique of a β-Hu Luobusu may further comprise the steps:
1) be that organic secondary amine of 5～10%, organic alkane of 10～15%, 75～85% methyl alcohol or ethanol mix and obtains reaction and promote liquid with volume percent;
2) by the mol ratio of 2～2.2:1, with 2,4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs and 2,7-dimethyl--2,4,6-sarohornene-1,8-dialdehyde are dissolved in reaction and promote in the liquid;
3) keep temperature of reaction at-10～0 ℃, in the reaction promotion liquid of a last step, add basic cpd, reaction obtains β-Hu Luobusu;
Wherein, organic secondary amine is selected from diethylamine, dipropyl amine, methylethyl amine, diisopropylamine; The carbonatoms of organic alkane is 5～8; 2,7-dimethyl--2,4,6-sarohornene-1, the 8-dialdehyde promotes that with reaction the mass volume ratio of liquid is 8～15:100.
2. the synthesis technique of a kind of β-Hu Luobusu according to claim 1, it is characterized in that: basic cpd is an alkali metal cpd.
3. the synthesis technique of a kind of β-Hu Luobusu according to claim 2, it is characterized in that: alkali metal cpd is selected from alkali-metal hydrogenate, oxyhydroxide, organic alcoholate.
4. the synthesis technique of a kind of β-Hu Luobusu according to claim 3, it is characterized in that: alkali-metal organic alcoholate is selected from alkali-metal methylate, trimethyl carbinol thing.
5. the synthesis technique of a kind of β-Hu Luobusu according to claim 1 is characterized in that: 2, and the mol ratio of 4-pentadiene 15 carbon SULPHOSUCCINIC ACID ESTERs and basic cpd is 1:1～2.
6. the synthesis technique of a kind of β-Hu Luobusu according to claim 1 is characterized in that: basic cpd adds the continued reaction 4 ~ 5 hours that finishes.
7. the synthesis technique of a kind of β-Hu Luobusu according to claim 1 is characterized in that: basic cpd repeatedly adds in batches.
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