CN105037085A - Method for efficiently preparing policosanol from Chinese wax by two-stage process - Google Patents
Method for efficiently preparing policosanol from Chinese wax by two-stage process Download PDFInfo
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- CN105037085A CN105037085A CN201510404794.2A CN201510404794A CN105037085A CN 105037085 A CN105037085 A CN 105037085A CN 201510404794 A CN201510404794 A CN 201510404794A CN 105037085 A CN105037085 A CN 105037085A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
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Abstract
The invention discloses a method for efficiently preparing policosanol from Chinese wax by a two-stage process. The method comprises: under normal pressure, reacting a reducing agent with Chinese wax in a mass ratio of 1g to (0.05-0.3)g, wherein 2 mole of policosanol is generated by use of 1 mole of Chinese wax; after the reaction is ended, adding a cosolvent and water, and enabling the cosolvent and the water to generate hydrolysis reaction, wherein a mass/volume/volume ratio of reactants Chinese wax to cosolvent to water is equal to 1g to (2-5)mL to (0.5-3)mL; then, removing water-soluble reducing products by washing, precipitating reducing products which are insoluble in water to bottom, and removing the reducing products by filtering; regulating the pH value to be neutral by pickling, converting precipitates into soluble substances, and washing the precipitates once by use of water, thereby obtaining a policosanol mixture product. The method is good in continuity on industrial production, easy to operate, environmentally-friendly, and high in yield.
Description
Technical field
The present invention relates to chemical technology field, particularly relate to a kind of method that high triacontanol efficiently prepared by two-step approach Insect Wax.
Background technology
High triacontanol, also known as high fatty alcohol, is containing chain saturated monohydroxy alcohols more than 12 carbon atoms.Very extensive in the existence of occurring in nature, but exist with natural free fatty alcohol hardly, and be normally present in all living things with the form of wax ester.The wax ester being wherein rich in high triacontanol has: rice bran wax, sugar-cane wax, jowar wax, Insect Wax, beeswax, carnauba wax, Sunflower Receptacle wax, shellac wax, wool wax etc.The important physiologically active that high triacontanol has and good market outlook, make high triacontanol as natural product development and utilization, to become the popular domain of fine chemistry industry, medicine and the industry research such as agriculture.At present both at home and abroad about the study hotspot of high triacontanol be C22 ~ C36 alcohol mixture preparation, be separated and utilize technical study.
At present, mainly contain from the waxed method of getting high triacontanol mixture of natural biological:
(1) wax saponification decomposition in the basic conditions, after removing soap, can obtain the mixture of high fatty alcohol.
(2) namely wax carry out transesterification reaction through alcoholysis, according to the different boiling of reaction product, by the method for vacuum distilling, is separated different products, thus obtains the mixture of high fatty alcohol.
(3) wax is directly reduced to fatty alcohol through reductive agent, as under certain condition, with lithium aluminum hydride as reductive agent, the Insect Wax of a mole can be directly reduced to the high triacontanol of two moles.
(4) wax is hydrolyzed in acid condition, then leaches fatty alcohol through supercutical fluid.
(5) wax decomposes through enzyme, extracts fatty alcohol.
Wherein reduction method can be reduced into the wax of one mole the high triacontanol of two moles, so in above several method, the product yield of reduction method is the highest, can the biological wax stock of efficiency utilization.
Patent 200810058584.2 discloses the method being prepared high triacontanol mixture by Insect Wax, and feature produces high triacontanol with reductive agent reduction Insect Wax in organic solvent, and shortcoming is that the use of solvent adds production cost,
Patent 200810058866.2 improves the technique that Insect Wax reduction method produces high triacontanol, in reduction reaction process no longer with an organic solvent, reduce cost, but the purity of high triacontanol product is low, quality is unreliable, and the aftertreatment technology of reduction reaction waits to improve.
Summary of the invention
The object of the present invention is to provide a kind of cost low, technique is simple, and efficiently, purity is high, the preparation method of the high triacontanol mixture of good product quality.
The present invention adopts following technical scheme:
The method of high triacontanol efficiently prepared by two-step approach Insect Wax of the present invention, it is characterized in that: the concrete steps of described method are as follows:
A: reduction reaction: take Insect Wax in reactor, and add reductive agent wherein, mass ratio is: Insect Wax: reductive agent=1: 0.05 ~ 0.3, makes it react, oil bath temperature 100 ~ 150 DEG C, reaction times 20 ~ 40min with oil bath heating;
B: the dissolving of reaction mixture and hydrolysis reaction: in the reaction system that step A obtains, according to reactant Insect Wax: solubility promoter: water=1: 2 ~ 5: 0.5 ~ 3 (mass/volume/volume ratios, g: mL: mL), add solubility promoter and water, heating makes mixed system backflow 10 ~ 30min, reflux temperature 50 ~ 100 DEG C;
C: solvent recuperation: stop step B reflux course, changes prolong, installs condensate recycling device, continues heating, recycling design, obtains not containing the reaction mixture of solubility promoter;
D: washing: after solvent recuperation, according to Insect Wax: water=1: 5 ~ 10 (mass/volume ratios, in the reaction mixture that in step C obtain add water g: mL), reflux 5 ~ 10min, upper strata high triacontanol mixture and lower floor's washings is separated after cooling, aluminium hydroxide is precipitated as, filtered and recycled wherein bottom washings;
E: pickling: add the hydrochloric acid that massfraction is 10 ~ 30% in the high triacontanol mixture that D step obtains, add-on is Insect Wax: hydrochloric acid=1: 1 ~ 3 (mass/volume ratio, g: mL), mixture system potential of hydrogen is regulated to be neutral, reflux 10 ~ 20min, is separated upper strata high triacontanol mixture and lower aqueous layer after cooling;
F: washing: according to Insect Wax in the high triacontanol mixture that E step obtains: water=1: 5 ~ 10 (mass/volume ratios, add water g: mL), reflux 10 ~ 20min, is separated upper strata high triacontanol and lower layer of water after cooling, obtains high triacontanol mix product;
The washing water that G: wastewater treatment: D step produces contain water-soluble higher reduzate, and heating evaporates the water, and residuum solid is recycled, and in E step and F step waste water, residue is less, meets emission standard.
In steps A, described reductive agent is powder lithium aluminum hydride or granular hydrogenation aluminium lithium, is commercial products.
In steps A, preferred Insect Wax: reductive agent=1: 0.2, oil bath temperature 120 DEG C, reaction times 30min.
In step B, described solubility promoter is the one in ethanol, acetone, methylene dichloride, chloroform or ethyl acetate.
In step B, preferably according to reactant Insect Wax: solubility promoter: water=1: 3: 2 (mass/volume/volume ratio, g: mL: mL), add solubility promoter and water, heating makes mixed system backflow 20min, reflux temperature 80 DEG C.
In step D, preferably according to Insect Wax: water=1: add water, reflux 8min in the reaction mixture that 8 (mass/volume ratio, g: mL) obtain in step C.
In step e, preferred hydrochloric acid add-on is Insect Wax: hydrochloric acid=1: 2 (mass/volume ratio, g: mL), regulates mixture system potential of hydrogen to be neutral, reflux 15min.
In step F, according to Insect Wax in the high triacontanol mixture preferably obtained in E step: water=1: 8 (mass/volume ratio, g: mL) add water, reflux 15min.
Described hydromining tap water.
Positively effect of the present invention is as follows:
The method that high triacontanol efficiently prepared by two-step approach Insect Wax of the present invention makes reduction reaction still keep relatively gentle speed of reaction after reaction activity arrives, be easy to control, reduce requirement and the cost of production unit, whole technological process is simply compact, easy to operate, reaction conversion ratio is high, side reaction is few, and gained high triacontanol mixture purity is high, steady quality, the three wastes are few, are easy to suitability for industrialized production.High triacontanol mixture that method of the present invention obtains (mixture forms: 24,26,28,30 alkanols) product yield up to 85 ~ 95%, far away higher than the yield of saponification method 20 ~ 30%.
Embodiment
Below in conjunction with specific embodiment, the present invention is described further.
Embodiment 1
A: take 10g Insect Wax in reactor, and add reductive agent powder lithium aluminum hydride 0.5g wherein, 100 DEG C of heating in oil bath, after 20min, reaction terminates, and forms a large amount of foam.
B: in the reaction system that step A obtains, adds solubility promoter ethanol 20mL, water 5mL, 70 DEG C of backflow 10min.
After the backflow of C:B step mixture terminates, condensate recycling device is installed, continues heating, reclaim ethanol, obtain not containing the reaction mixture of solubility promoter.
D: in the mixture that step C obtains, add 50mL water, backflow 5min, is separated upper strata high triacontanol mixture and lower floor's washings after cooling, is precipitated as aluminium hydroxide, filtered and recycled bottom washings.
E: add the hydrochloric acid 10mL of 10% in the high triacontanol mixture that D step obtains, now mixture system potential of hydrogen is neutral, and reflux 10min is separated upper strata high triacontanol mixture and lower aqueous layer after cooling.
F: add water 50mL, reflux 10min in the high triacontanol mixture that E step obtains, is separated upper strata high triacontanol and lower layer of water after cooling, obtains high triacontanol mixture (mixture forms: 24,26,28,30 alkanols) product.High triacontanol yield up to 88%, far away higher than the yield of saponification method 20 ~ 30%.
The washing water that G: wastewater treatment: D step produces contain water-soluble higher reduzate, and heating evaporates the water, and residuum solid is recycled.
Embodiment 2
A: take Insect Wax 100g in reactor, and add reductive agent granular hydrogenation aluminium lithium 30g wherein, oil bath 150 DEG C of heating make it react, reaction times 30min.
B: in the reaction system that step A obtains, adds solubility promoter chloroform 300mL, water 100mL, is heated to 50 DEG C and makes mixed system backflow 20min.
C: stop step B reflux course, changes prolong, installs condensate recycling device, continues heating, recycling design chloroform, obtains not containing the reaction mixture of solubility promoter.
D: after solvent recuperation, adds 800mL water, reflux 8min in the reaction mixture that step C obtains, and is separated upper strata high triacontanol mixture and lower floor's washings after cooling, is precipitated as aluminium hydroxide, filtered and recycled wherein bottom washings.
E: the hydrochloric acid adding 200mL20% in the high triacontanol mixture that D step obtains, reflux 15min, be separated upper strata high triacontanol mixture and lower aqueous layer after cooling.
F: add 800mL water, reflux 15min in the high triacontanol mixture that E step obtains, is separated upper strata high triacontanol and lower layer of water after cooling, obtains high triacontanol mixture (mixture forms: 24,26,28,30 alkanols) product.High triacontanol yield up to 90%, far away higher than the yield of saponification method 20 ~ 30%.
The washing water that G: wastewater treatment: D step produces contain water-soluble higher reduzate, and heating evaporates the water, and residuum solid is recycled.
Embodiment 3
A: take 1kg Insect Wax in reactor, and add granular hydrogenation aluminium lithium reductive agent 300g wherein, make it react with oil bath heating, oil bath temperature 150 DEG C, reaction times 40min.
B: in the reaction system that step A obtains, add solubility promoter ethyl acetate 5L, water 3L, is heated to 70 DEG C and makes mixed system backflow 30min.
C: stop step B reflux course, changes prolong, installs condensate recycling device, continues 70 DEG C of heating, recycling design ethyl acetate, obtains not containing the reaction mixture of solubility promoter.
D: after solvent recuperation, adds 10L water, reflux 10min in the reaction mixture that step C obtains, and is separated upper strata high triacontanol mixture and lower floor's washings after cooling, is precipitated as aluminium hydroxide, filtered and recycled wherein bottom washings.
E: the hydrochloric acid adding 3L30% in the high triacontanol mixture that D step obtains, reflux 20min, be separated upper strata high triacontanol mixture and lower aqueous layer after cooling.
F: add 10L water, reflux 20min in the high triacontanol mixture that E step obtains, is separated upper strata high triacontanol and lower layer of water after cooling, obtains high triacontanol mixture (mixture forms: 24,26,28,30 alkanols) product.High triacontanol yield up to 92%, far away higher than the yield of saponification method 20 ~ 30%.
The washing water that G:D step produces contain water-soluble higher reduzate, and heating evaporates the water, and residuum solid is recycled.In E step and F step waste water, residue is less, meets emission standard, directly discharges.
Embodiment 4
A: take 10g Insect Wax in reactor, and add reductive agent powder lithium aluminum hydride 2g wherein, 120 DEG C of heating in oil bath, after 30min, reaction terminates, and forms a large amount of foam.
B: in the reaction system that step A obtains, adds solubility promoter ethanol 30mL, water 20mL, 80 DEG C of backflow 20min.
After the backflow of C:B step mixture terminates, condensate recycling device is installed, continues heating, reclaim ethanol, obtain not containing the reaction mixture of solubility promoter.
D: in the mixture that step C obtains, add 80mL water, backflow 8min, is separated upper strata high triacontanol mixture and lower floor's washings after cooling, is precipitated as aluminium hydroxide, filtered and recycled bottom washings.
E: add the hydrochloric acid 20mL of 10% in the high triacontanol mixture that D step obtains, now mixture system potential of hydrogen is neutral, and reflux 15min is separated upper strata high triacontanol mixture and lower aqueous layer after cooling.
F: add water 80mL, reflux 15min in the high triacontanol mixture that E step obtains, is separated upper strata high triacontanol and lower layer of water after cooling, obtains high triacontanol mixture (mixture forms: 24,26,28,30 alkanols) product.High triacontanol yield up to 95%, far away higher than the yield of saponification method 20 ~ 30%.
The washing water that G: wastewater treatment: D step produces contain water-soluble higher reduzate, and heating evaporates the water, and residuum solid is recycled.
Although illustrate and describe embodiments of the invention, for the ordinary skill in the art, be appreciated that and can carry out multiple change, amendment, replacement and modification to these embodiments without departing from the principles and spirit of the present invention, scope of the present invention is by claims and equivalents thereof.
Claims (8)
1. a method for high triacontanol efficiently prepared by two-step approach Insect Wax, it is characterized in that: the concrete steps of described method are as follows:
A: reduction reaction: take Insect Wax in reactor, and add reductive agent wherein, mass ratio is: Insect Wax: reductive agent=1: 0.05 ~ 0.3, makes it react, oil bath temperature 100 ~ 150 DEG C, reaction times 20 ~ 40min with oil bath heating;
B: the dissolving of reaction mixture and hydrolysis reaction: in the reaction system that step A obtains, according to reactant Insect Wax: solubility promoter: water=1: 2 ~ 5: 0.5 ~ 3 (mass/volume/volume ratios, g: mL: mL), add solubility promoter and water, heating makes mixed system backflow 10 ~ 30min, reflux temperature 50 ~ 100 DEG C;
C: solvent recuperation: stop step B reflux course, changes prolong, installs condensate recycling device, continues heating, recycling design, obtains not containing the reaction mixture of solubility promoter;
D: washing: after solvent recuperation, according to Insect Wax: water=1: 5 ~ 10 (mass/volume ratios, in the reaction mixture that in step C obtain add water g: mL), reflux 5 ~ 10min, upper strata high triacontanol mixture and lower floor's washings is separated after cooling, aluminium hydroxide is precipitated as, filtered and recycled wherein bottom washings;
E: pickling: add the hydrochloric acid that massfraction is 10 ~ 30% in the high triacontanol mixture that D step obtains, add-on is Insect Wax: hydrochloric acid=1: 1 ~ 3 (mass/volume ratio, g: mL), mixture system potential of hydrogen is regulated to be neutral, reflux 10 ~ 20min, is separated upper strata high triacontanol mixture and lower aqueous layer after cooling;
F: washing: according to Insect Wax in the high triacontanol mixture that E step obtains: water=1: 5 ~ 10 (mass/volume ratios, add water g: mL), reflux 10 ~ 20min, is separated upper strata high triacontanol and lower layer of water after cooling, obtains high triacontanol mix product;
The washing water that G: wastewater treatment: D step produces contain water-soluble higher reduzate, and heating evaporates the water, and residuum solid is recycled, and in E step and F step waste water, residue is less, meets emission standard.
2. the method for high triacontanol efficiently prepared by two-step approach Insect Wax as claimed in claim 1, and it is characterized in that: in steps A, described reductive agent is powder lithium aluminum hydride or granular hydrogenation aluminium lithium, is commercial products.
3. the method for high triacontanol efficiently prepared by two-step approach Insect Wax as claimed in claim 1, it is characterized in that: in steps A, Insect Wax: reductive agent=1: 0.2, oil bath temperature 120 DEG C, reaction times 30min.
4. the method for high triacontanol efficiently prepared by two-step approach Insect Wax as claimed in claim 1, and it is characterized in that: in step B, described solubility promoter is the one in ethanol, acetone, methylene dichloride, chloroform or ethyl acetate.
5. the method for high triacontanol efficiently prepared by two-step approach Insect Wax as claimed in claim 1, it is characterized in that: in step B, according to reactant Insect Wax: solubility promoter: water=1: 3: 2 (mass/volume/volume ratios, g: mL: mL), add solubility promoter and water, heating makes mixed system backflow 20min, reflux temperature 80 DEG C.
6. the method for high triacontanol efficiently prepared by two-step approach Insect Wax as claimed in claim 1, it is characterized in that: in step D, according to Insect Wax: water=1: add water, reflux 8min in the reaction mixture that 8 (mass/volume ratio, g: mL) obtain in step C.
7. the method for high triacontanol efficiently prepared by two-step approach Insect Wax as claimed in claim 1, it is characterized in that: in step e, hydrochloric acid add-on is Insect Wax: hydrochloric acid=1: 2 (mass/volume ratio, g: mL), mixture system potential of hydrogen is regulated to be neutral, reflux 15min.
8. the method for high triacontanol efficiently prepared by two-step approach Insect Wax as claimed in claim 1, it is characterized in that: in step F, according to Insect Wax in the high triacontanol mixture that E step obtains: water=1: 8 (mass/volume ratio, g: mL) add water, reflux 15min.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112500263A (en) * | 2020-12-07 | 2021-03-16 | 中国林业科学研究院资源昆虫研究所 | Method for preparing higher alkanol by reducing white wax with red aluminum under normal pressure |
CN112890172A (en) * | 2021-01-29 | 2021-06-04 | 中国林业科学研究院资源昆虫研究所 | Higher alkanol microcapsule, preparation method and application thereof in effervescent tablets |
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US5608122A (en) * | 1995-04-11 | 1997-03-04 | Metallgesellschaft Ag | Process for preparing wax esters and hydrogenation of wax esters to fatty alcohols |
CN101386562A (en) * | 2008-08-29 | 2009-03-18 | 中国林业科学研究院资源昆虫研究所 | Method for preparing policosanol mixture by nonsolvent reduction method |
WO2010103549A2 (en) * | 2009-03-12 | 2010-09-16 | Godavari Biorefineries Ltd | A method of obtaining policosanols from natural material |
CN103804125A (en) * | 2012-11-06 | 2014-05-21 | 中国林业科学研究院资源昆虫研究所 | Method for preparing policosanol through insect wax pressure reduction method |
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2015
- 2015-07-10 CN CN201510404794.2A patent/CN105037085A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US5608122A (en) * | 1995-04-11 | 1997-03-04 | Metallgesellschaft Ag | Process for preparing wax esters and hydrogenation of wax esters to fatty alcohols |
CN101386562A (en) * | 2008-08-29 | 2009-03-18 | 中国林业科学研究院资源昆虫研究所 | Method for preparing policosanol mixture by nonsolvent reduction method |
WO2010103549A2 (en) * | 2009-03-12 | 2010-09-16 | Godavari Biorefineries Ltd | A method of obtaining policosanols from natural material |
CN103804125A (en) * | 2012-11-06 | 2014-05-21 | 中国林业科学研究院资源昆虫研究所 | Method for preparing policosanol through insect wax pressure reduction method |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112500263A (en) * | 2020-12-07 | 2021-03-16 | 中国林业科学研究院资源昆虫研究所 | Method for preparing higher alkanol by reducing white wax with red aluminum under normal pressure |
CN112890172A (en) * | 2021-01-29 | 2021-06-04 | 中国林业科学研究院资源昆虫研究所 | Higher alkanol microcapsule, preparation method and application thereof in effervescent tablets |
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