CN106187677A - A kind of method and application preparing senior fat primary alcohol mixture with cerosin - Google Patents
A kind of method and application preparing senior fat primary alcohol mixture with cerosin Download PDFInfo
- Publication number
- CN106187677A CN106187677A CN201610573043.8A CN201610573043A CN106187677A CN 106187677 A CN106187677 A CN 106187677A CN 201610573043 A CN201610573043 A CN 201610573043A CN 106187677 A CN106187677 A CN 106187677A
- Authority
- CN
- China
- Prior art keywords
- cerosin
- saponification
- primary alcohol
- alcohol mixture
- alkali
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of method and application preparing senior fat primary alcohol mixture with cerosin, after described method includes dissolving cerosin organic solvent, alkali, phase transfer catalyst work under carry out the step of saponification, and saponification liquid is decoloured, recrystallization extracts the step of product；Wherein, described phase transfer catalyst is Polyethylene Glycol, adding Polyethylene Glycol in reaction system and can improve reaction yield, the temperature of the saponification of the present invention is less than 100 DEG C, and the response time is less than 100min, the reduction of temperature, the shortening of time can save the energy, reducing entreprise cost, and i.e. can get product through saponification and post processing two-step reaction, process is simple, easy to operate, beneficially industrialized production.
Description
Technical field
The present invention relates to medical material production technical field, particularly relate to one and prepare senior fat primary alcohol mixing with cerosin
The method of thing and application.
Background technology
Cerosin is the waxiness on a kind of sugarcane epidermis, and Caulis Sacchari sinensis, after squeezing, is attached to the cerosin of sugarcane epidermis, except remaining in
Outside bagasse part person, the cerosin of about 40% flows in juice, and the most about 95% is adsorbed by filter mud during filtration.Therefore, sugar refinery
Filter mud be the main source of cerosin.
Policosanol (also known as many twenty alcohol) is skies that the effective ingredient extracted from cerosin is made, containing 8 kinds of primary aliphatic alcohols
So chemicals, chemical formula is CH3(CH2)nCH2OH, chain length is from 24 to 34 carbon atoms.Many twenty alcohol have can suppress cholesterol
Synthesis, improve low density lipoprotein, LDL (LDL) blood clearance, effectively reduce low-density lipoprotein cholesterol (LDL-C) level,
Improve the effects such as HDL-C (HDL-C) level, substantially suppression platelet aggregation, be one safely and effectively, more
Easy-tolerated novel lipid lowering agent.
Chinese patent CN1100744C discloses a kind of method being produced senior fat primary alcohol mixture by cerosin: by cerosin
Homogeneous saponification 1-3h in butanol solution, acidifying, separate organic facies, adding calcium hydroxide and activated carbon decolorizing, filter, reclaim butanol
To dry, obtain crude product, then use ethanol decolorization recrystallization, add dichloroethanes and process, filter, dry to constant weight, obtain senior for 60-65 DEG C
Primary fat alcohol mixture.This patent first generates corresponding carboxylate and senior fat primary alcohol through saponification, and then acidifying obtains
Carboxylic acid and senior fat primary alcohol, the carboxylic acid generated with reaction in calcium hydroxide is carboxylic acid calcium salt, i.e. operation course is saponification, acid
Change, neutralize, crystallize, complex process, and butanol boils up till 117 DEG C, there is the defect that energy resource consumption is big during industrialized production.
Chinese patent CN102795960B discloses the scale preparation side of a kind of high-purity octacosanol, triacontanol
Method, belongs to the comprehensive utilization of animals and plants wax.The method comprises the following steps successively: calcium oxide or calcium hydroxide by weight ratio
And mix with water, then it is 200-250 DEG C in temperature and reacts 8-10h with native paraffin that cooling obtains solid product；Extract with ethanol again
Take, temperature 70-78 DEG C, time 1-2h, it is thus achieved that long-chain fatty alcohol；Then by gained long-chain fatty alcohol vacuum be 5-20Pa,
Temperature is 175-270 DEG C of prefractionation 10-12h, collects the fraction of 175-270 DEG C；Carry out pillar molecular distillation again, obtain corresponding
Octacosanol or triacontanol.This patent saponification temperature is high, and the response time is long.
In sum, the existing method preparing senior fat primary alcohol mixing for raw material with cerosin also exists the response time
Long, reaction temperature is high, and operating process is complicated, is unfavorable for the defect of industrialized production, it is therefore proposed that one is suitable for industry metaplasia
The method produced is highly significant.
Summary of the invention
It is an object of the invention to provide a kind of method preparing senior fat primary alcohol mixture with cerosin, the method has work
Skill is simple, and time-consumingly few, reaction temperature is low, low cost and other advantages.
To achieve these goals, the present invention adopts the following technical scheme that
A kind of method preparing senior fat primary alcohol mixture with cerosin, after cerosin is dissolved with organic solvent,
Alkali, phase transfer catalyst effect under carry out the step of saponification.
The present invention carries out the fusion method of report in saponification, with prior art again and dissolves cerosin phase after first being dissolved by cerosin
Ratio, cerosin dissolves more abundant in a solvent, and the alkali in system can be brought in organic facies by the addition of phase transfer catalyst,
Cerosin can be fully contacted with alkali, and saponification is more complete, and yield is higher.
The phase transfer catalyst that the present invention uses is preferably Polyethylene Glycol, and further preferred molecular weight is the poly-of 200-2000
Ethylene glycol, most preferably PEG400, Macrogol 600, polyethylene glycol-800, cetomacrogol 1000, polyethylene glycol 1500
In one or more.Compared with the Polyethylene Glycol of high molecular (such as 4000-20000), the present invention uses low-molecular-weight (200-
2000) Polyethylene Glycol has more preferable dissolubility in organic solvent, and catalysis activity is higher.
In a particular embodiment, Macrogol 600, or polyethylene glycol 200, or Polyethylene Glycol can such as be used
400, or cetomacrogol 1000, or the mixture of PEG400 and Macrogol 600 etc. is as phase transfer catalyst.Poly-second
The link of glycols can be folded into helical form chain slidably, and it can be with the alkali metal in reaction reagent, alkaline earth gold
Belonging to and generate stable coordination compound, now, oxygen atom is positioned at inner side, forms 7～8 oxygen atoms and is in conplane false shape ring knot
Structure, the most curved side stretching in plane of remaining oxygen atom, it is dissolved in organic facies, so that nucleopilic reagent is exposed out, is allowed to have
Higher reactivity.
The consumption of phase transfer catalyst can be added according to general knowledge known in this field, and currently preferred addition is alkali
The 1-6%, more preferably 2-3% of mole.
The present invention is dissolved the organic solvent of cerosin and is preferably employed chloralkane kind solvent or alcohols solvent, and alcohols solvent is preferred
Use the alcohol of carbon number 1-4.
Specifically, in dichloromethane, chloroform, dichloroethanes, methanol, ethanol, normal propyl alcohol, n-butyl alcohol can be used
Kind, the present invention most preferably uses dichloromethane and ethanol as reaction dissolvent, and this kind solvent has the splendid energy dissolving cerosin
Power.The consumption of organic solvent is advisable can be completely dissolved cerosin, and the consumption of the preferred organic solvent of the present invention is 2-8L/kg sugarcane
Wax.
Described alkali can use the inorganic base that saponification is conventional, and the preferred described alkali of the present invention is selected from sodium hydroxide, hydroxide
One or more in potassium, calcium hydroxide, in a particular embodiment, such as, can individually use sodium hydroxide, or use hydrogen
The mixture of calcium oxide and sodium hydroxide is as alkali.It is further preferred that the 0.1-0.3 that the consumption of described alkali is cerosin weight
Times.
Cerosin of the present invention can be crude cane wax or refined after cerosin.
Carry out the reaction system of saponification can also contain the optional addO-on therapy that water, i.e. water are saponification, add
When adding water, the addition of water is preferably 1-3 times of alkali weight.
When reaction system does not contains water, alkali and phase transfer catalyst are directly added in the cerosin after dissolving；
When in reaction system containing water, first alkali dissolution can be formed in water alkali liquor, then phase transfer catalyst be added alkali liquor
Middle formation mixed solution, finally adds this mixed solution in the cerosin after dissolving.
The condition of described saponification is: in 40-80 DEG C of stirring reaction 30-100min.The rotating speed wherein stirred is preferably
100-300rpm。
Specifically, the operation of described saponification is: use the ratio of 2-8L organic solvent according to every kg cerosin, with molten
Cerosin is dissolved by agent, and the Polyethylene Glycol of the alkali and the 1-6% accounting for alkali mole that are subsequently adding cerosin weight 0.05-0.3 times turns mutually
Shifting catalyst, in 40-80 DEG C of stirring reaction 30-100min.
The present invention carries out the temperature of saponification and is 40-80 DEG C cerosin, and the response time is 30-100min, and in reaction
Water be can addO-on therapy, reaction system is near homogeneously, and reaction temperature, response time are below prior art, and stable yield exists
About 30%, there is production cost low, save the advantage of the energy, be extremely suitable for industrialized production.
Method of the present invention also includes the step that the reactant liquor after saponification carries out post processing, described post processing
For: washing reactant liquor with water, separate organic facies, after decolouring described organic facies with activated carbon, recycling design, to doing to obtain crude product, is used
Ethanol carries out recrystallization to described crude product and get final product.
Wherein, described decolouring is: add the activated carbon accounting for cerosin weight 2%-5% in organic facies, in 70-80 DEG C of decolouring
30-50min。
Described recrystallization is: add the ratio of 5-20mL ethanol in every gram of crude product, addition ethanol in described crude product, and in
55-78 DEG C of dissolving, is cooled to room temperature, stands crystallize and get final product.
The ethanol preferred volume concentration that recrystallization uses is the ethanol water of 90%-100%.
Specifically, the operation of described post processing is: washes the reactant liquor after saponification with water, isolates organic facies,
In organic facies, add the activated carbon accounting for cerosin weight 2%-5%, in 70-80 DEG C of stirring decolouring 30-50min, then remove and have
Machine solvent obtains the crude product being dried；The ratio of 5-20mL ethanol is added in every gram of crude product, addition ethanol in described crude product, and in
55-78 DEG C of dissolving, is cooled to room temperature, stands crystallize and i.e. obtains sterling.
Preferably, when reaction dissolvent uses ethanol, after reaction terminates, after recyclable partial solvent, directly carry out once
Crystallization operation；Carrying out secondary recrystallization with ethanol the most again, product purity is higher.
The present invention also provides for the senior fat primary alcohol mixture using any one method above-mentioned to prepare.
Preferably, described senior fat primary alcohol mixture contains the 1-tetracosanol of 0.5-1.5%wt, 5-10%wt
1-hexacosanol, 1-5%wt heptacosanol, the 1-octacosanol of 60-75%wt, the 1-melissane of 5-15%wt
Alcohol, the 1-n-Dotriacontanol of 3-8%wt.
It is further preferred that described senior fat primary alcohol mixture contains the 1-tetracosanol of 0.5-1%wt, 6-
The 1-hexacosanol of 8%wt, 2-4%wt heptacosanol, the 1-octacosanol of 65-72%wt, the 1-tri-of 7-11%wt
Ten alkanols, the 1-n-Dotriacontanol of 3-6%wt.
The present invention also provide for senior fat primary alcohol that any one method above-mentioned prepares preparation treatment blood fat reducing and/
Or the application in anticholesteremic agent.
When specifically applying, can described senior fat primary alcohol mixture be main active, be prepared into medicine
Compositions.Or add pharmaceutically acceptable carrier and/or adjuvant, be prepared into preparation commonly used in the art, as tablet,
Capsule, granule, pill, injection etc..Wherein, described carrier, adjuvant dawn known to those skilled in the art, the present invention couple
This does not do restriction further.
First cerosin is dissolved by the present invention with organic solvent, and then saponification occurs under the effect of phase transfer catalyst
Generate senior fat primary alcohol mixture, dissolve cerosin with existing employing fusion method, do not use phase transfer catalyst to compare, have
Saponification temperature is low, and the response time is short, the advantage that yield is high.The reduction of reaction temperature, the shortening in response time, it is possible to save
The energy, reduces entreprise cost.The present invention i.e. can get product through saponification and post processing two-step reaction, and process is simple, behaviour
Facilitate, beneficially industrialized production.
On the basis of meeting common sense in the field, above-mentioned each optimum condition, can be mutually combined, obtain the present invention each preferably
Embodiment.
Detailed description of the invention
Following example are used for illustrating the present invention, but are not limited to the scope of the present invention.The raw material that the present invention relates to or
The most commercially available acquisition of reagent, the operation related to is this area routine techniques means.
Embodiment 1
A kind of method preparing senior fat primary alcohol mixture with cerosin, weighs 100Kg cerosin and is dissolved in 300L dichloromethane
In join in retort, 20Kg sodium hydroxide is dissolved in 30Kg water, 9Kg Macrogol 600 is dissolved in sodium hydroxide solution
In, join together in retort, controlling mixing speed is 180 revs/min, in 40 DEG C of back flow reaction 100min.Saponification is tied
Shu Hou, releases reactant liquor, uses 120L distilled water to wash organic facies, stratification in three times, takes lower organic layer.To organic layer
Middle addition 3Kg activated carbon reflux decolour 40min, filtered while hot, recycling design, obtain crude product 34.9Kg.Use 95% ethanol
170.5L dissolves crude product under conditions of heating-up temperature is 70 DEG C, after all dissolving, stops heating, is cooled to room temperature, stands
Crystallize, is dried to obtain senior fat primary alcohol mixture 31.4Kg, and yield is 31.4%.
Embodiment 2
A kind of method preparing senior fat primary alcohol mixture with cerosin, weighs 100Kg cerosin and is dissolved in 300L n-butyl alcohol
Join in retort, 22Kg potassium hydroxide is dissolved in 22Kg water, 6.3Kg polyethylene glycol-800 is dissolved in sodium hydroxide solution
In, join together in retort, controlling mixing speed is 180 revs/min, reacts 100min in 80 DEG C.After saponification terminates,
Release reactant liquor, use 120L distilled water to wash organic facies, stratification in three times, take lower organic layer.Add in organic layer
Enter 3Kg activated carbon reflux decolour 40min, filtered while hot, recycling design, obtain crude product 32.7Kg.Adding with 95% ethanol 157L
Hot temperature dissolves crude product under conditions of being 70 DEG C, after all dissolving, stops heating, is cooled to room temperature, stand crystallize, is dried
To senior fat primary alcohol mixture 29.9Kg, yield is 29.9%.
Embodiment 3
A kind of method preparing senior fat primary alcohol mixture with cerosin, weighs 100Kg cerosin and is dissolved in 400L ethanol and adding
Entering in retort, 16Kg sodium hydroxide, 4.8Kg PEG400 are joined together in retort, mixing speed is 180
Rev/min, 79 DEG C of backflow 100min.After saponification terminates, release reactant liquor, regulate Ph with the hydrochloric acid of 1mol/l the most neutral, to
Wherein add 3.5Kg activated carbon reflux decolour 40min, filtered while hot, the 1/4 of recycling design to original volume, stand crystallize and obtain
Crude product 33.1Kg.Under conditions of heating-up temperature is 70 DEG C, dissolve crude product with 95% ethanol 165.5L, after all dissolving, stop
Heating, is cooled to room temperature, stands crystallize, is dried to obtain senior fat primary alcohol mixture 30.1Kg, and yield is 30.1%.
Embodiment 4
A kind of method preparing senior fat primary alcohol mixture with cerosin, weighs 100Kg cerosin and is dissolved in 300L dichloromethane
In join in retort, 20Kg potassium hydroxide is dissolved in 20Kg water, joins anti-together with 7.14Kg cetomacrogol 1000
Answering in tank, mixing speed is 220 revs/min, 40 DEG C of backflow 100min.After saponification terminates, releasing reactant liquor, filtered while hot,
150L distilled water is used to wash organic facies in three times.Isolate organic facies, be added thereto to 2.5Kg activated carbon reflux decolour
40min, filtered while hot, recycling design, obtain crude product 31.5Kg.With dehydrated alcohol 148L under conditions of heating-up temperature is 70 DEG C
Dissolve crude product, after all dissolving, stop heating, be cooled to room temperature, stand crystallize, be dried to obtain senior fat primary alcohol mixture
27.8Kg, yield is 27.8%.
Embodiment 5
A kind of method preparing senior fat primary alcohol mixture with cerosin, weighs 100Kg refined cane wax and is dissolved in 300L dichloro
Methane joins in retort, 20Kg sodium hydroxide is dissolved in 10Kg water, 2.5Kg Macrogol 600 is dissolved in hydroxide
In sodium solution, joining together in retort, controlling mixing speed is 180 revs/min, in 40 DEG C of back flow reaction 100min.Saponification
After reaction terminates, release reactant liquor, use 120L distilled water to wash organic facies, stratification in three times, take lower organic layer.To
Organic layer adds 3Kg activated carbon reflux decolour 40min, filtered while hot, recycling design, obtains crude product 55.4Kg.Use 95% second
Alcohol 170.5L dissolves crude product under conditions of heating-up temperature is 70 DEG C, after all dissolving, stops heating, is cooled to room temperature, quiet
Putting crystallize, be dried to obtain senior fat primary alcohol mixture 51.6Kg, yield is 51.6%.
Comparative example 1
Weigh 100Kg cerosin and join in retort, in 110-115 DEG C of melting, 20Kg sodium hydroxide is dissolved in 200L water
In, join in retort, mixing speed is 180 revs/min, 100 DEG C of backflow 3h.After saponification terminates, release reactant liquor, cold
But to room temperature, add 300L chloroform each many twenty alcohol of 100L extraction in three times, merge organic facies, be added thereto to 3Kg activated carbon
Reflux decolour 40min, filtered while hot, recycling design, obtain crude product 24.9Kg.It is 70 with 95% ethanol 124.5L in heating-up temperature
Dissolve crude product under conditions of DEG C, after all dissolving, stop heating, be cooled to room temperature, stand crystallize, be dried to obtain higher aliphatic
Primary alcohol mixture 21.4Kg, yield is 21.4%.
Comparative example 2
A kind of method preparing senior fat primary alcohol mixture with cerosin, weighs 100Kg cerosin and is dissolved in 300L dichloromethane
In join in retort, 20Kg sodium hydroxide is dissolved in 30Kg water, 9Kg Macrogol 4000 is dissolved in sodium hydroxide solution
In, join together in retort, controlling mixing speed is 180 revs/min, in 40 DEG C of back flow reaction 100min.Saponification is tied
Shu Hou, releases reactant liquor, uses 120L distilled water to wash organic facies, stratification in three times, takes lower organic layer.To organic layer
Middle addition 3Kg activated carbon reflux decolour 40min, filtered while hot, recycling design, obtain crude product 25.5Kg.Use 95% ethanol
122.4L dissolves crude product under conditions of heating-up temperature is 70 DEG C, after all dissolving, stops heating, is cooled to room temperature, stands
Crystallize, is dried to obtain senior fat primary alcohol mixture 22.1Kg, and yield is 22.1%.
Comparative example 3
A kind of method with cerosin system times senior fat primary alcohol mixture, weighs 100Kg cerosin and is dissolved in 300L dichloromethane
In join in retort, 20Kg sodium hydroxide is dissolved in 30Kg water, 9Kg PEG20000 is dissolved in sodium hydroxide molten
In liquid, joining together in retort, controlling mixing speed is 180 revs/min, in 40 DEG C of back flow reaction 100min.Saponification
After end, release reactant liquor, use 120L distilled water to wash organic facies, stratification in three times, take lower organic layer.To organic
Add 3Kg activated carbon reflux decolour 40min, filtered while hot, recycling design in Ceng, obtain crude product 24.3Kg.Use 95% ethanol
116.6L dissolves crude product under conditions of heating-up temperature is 70 DEG C, after all dissolving, stops heating, is cooled to room temperature, stands
Crystallize, is dried to obtain senior fat primary alcohol mixture 20.9Kg, and yield is 20.9%.
Comparative example 4
A kind of method with cerosin system times senior fat primary alcohol mixture, weighs 100Kg cerosin and is dissolved in 300L dichloromethane
In join in retort, 20Kg sodium hydroxide is dissolved in 30Kg water, 9Kg18 hat 6 is dissolved in sodium hydroxide solution, together
Joining in retort, controlling mixing speed is 180 revs/min, in 40 DEG C of back flow reaction 100min.After saponification terminates, put
Go out reactant liquor, use 120L distilled water to wash organic facies, stratification in three times, take lower organic layer.Add in organic layer
3Kg activated carbon reflux decolour 40min, filtered while hot, recycling design, obtain crude product 34.1Kg.Adding with 95% ethanol 170.5L
Hot temperature dissolves crude product under conditions of being 70 DEG C, after all dissolving, stops heating, is cooled to room temperature, stand crystallize, is dried
To senior fat primary alcohol mixture 30.9Kg, yield is 30.9%.
Comparative example 5
A kind of method preparing senior fat primary alcohol mixture with cerosin, weighs 100Kg cerosin and is dissolved in 300L dichloromethane
In join in retort, 5Kg sodium hydroxide is dissolved in 30Kg water, 750g Macrogol 600 is dissolved in sodium hydroxide solution
In, join together in retort, controlling mixing speed is 180 revs/min, in 40 DEG C of back flow reaction 100min.Saponification is tied
Shu Hou, releases reactant liquor, uses 120L distilled water to wash organic facies, stratification in three times, takes lower organic layer.To organic layer
Middle addition 3Kg activated carbon reflux decolour 40min, filtered while hot, recycling design, obtain crude product 7.96Kg.With 95% ethanol 38.2L
Under conditions of heating-up temperature is 70 DEG C, dissolves crude product, after all dissolving, stops heating, be cooled to room temperature, stand crystallize, dry
Dry obtaining senior fat primary alcohol mixture 7.53Kg, yield is 7.53%.
Using gas chromatography and formula calculated as below to measure embodiment 1-5, in comparative example 1-5 product, each component contains
Amount, result is as shown in table 1:
Chromatographic condition: chromatographic column: InertCap 5MS/NP (30m × 0.25mm, 0.25 μm)；Detector: hydrogen flame ion
Change detector；Detector temperature 280 DEG C；Injector temperature: 250 DEG C；Column temperature rise program: column oven initial temperature is 60 DEG C of guarantors
Per minute it is warming up to 280 DEG C with 8 DEG C after holding 1min, keeps 10min；Carrier gas: helium；Flow velocity: 3mL/min；Sample size 1 μ L.
The quantitative analysis of each alcohol content
Accurately weigh the 1-octacosanol standard sample of 25mg in 50mL volumetric flask, add a small amount of chloroform, place temperature
In water, dissolve under ultrasound wave, about 10min, be cooled to room temperature, constant volume.Draw respectively 1mL, 2mL, 3mL, 4mL, 5mL, 6mL in
In 10mL volumetric flask, add chloroform constant volume, draw 1 μ l sample detection respectively, with the quality of 1-octacosanol as abscissa, with
Chromatographic peak area is that vertical coordinate prepares standard curve.
The quantitative analysis method of other each alcohol content is identical with the quantitative analysis method of 1-octacosanol.
A. policosanol yield (%)=[(many twenty alcohol weight × total alcohol content)/cerosin weight] × 100；
B. the summation of total alcohol content (%)=each alcohol content
The detection method of the most each alcohol content
Table 1 embodiment 1-5, comparative example 1-5 experimental result
It can be seen from the results above that use the method for the present invention can obtain senior fat primary alcohol mixing with high yield
Thing, during with crude cane wax for raw material, yield is between 27.8%-31.4%, and during with refined cane wax for raw material, yield is 51.6%,
Yield higher than other comparative examples.Although the yield of comparative example 4 is 30.9%, but crown ether is expensive, and toxicity is relatively big, is not suitable for
In industrialized production.
Effect test
High lipid food: normal diet 83%, Adeps Sus domestica 10%, egg yolk 5%, cholesterol 1.6%, propylthiouracil
0.2%, cholate 0.2%.
Gavage solution: empirically require to be configured to respective concentration with 2% sodium carboxymethyl cellulose by many twenty alcohol, lovastatin
Suspension.
Choose the purebred rat of Wistar, 90, male and female half and half, cleaning grade, body weight 160～180g.By these 90 before experiment
The purebred rat of Wistar feed normal feedstuff under standard laboratory atmosphere, fasting 12h posterior orbit venous blood collection, prepare serum, survey
(high density lipoprotein gallbladder is solid for the fixed TC (T-CHOL) of each group of rat blood serum, LDL-C (low-density lipoprotein cholesterol), HDL-C
Alcohol), TG (triglyceride).Purebred for Wistar rat is randomly divided into 2 groups, blank group (15), hyperlipidemia model group (75
Only).Blank group feed normal feedstuff feed 4 weeks, hyperlipidemia model group, with high lipid food feed 4 weeks, begin setting up rat drink
Feeding habits hyperlipemia model, fasting 12h posterior orbit venous blood collection measure respectively the serum of two groups of rats TC (T-CHOL),
LDL-C (low-density lipoprotein cholesterol), HDL-C (HDL-C), TG (triglyceride).
In 5-12 week, hyperlipidemia model group (75) being randomly divided into 5 groups, often group 15, one group is that many twenty alcohol A groups (use
The product that embodiment 1 prepares), one group is many twenty alcohol B groups (using the product that embodiment 2 prepares), and one group is many twenty
Alcohol C group (uses the product that embodiment 5 prepares), and one group is lovastatin group, and one group is policosanol sheet group, is feeding for 5 groups
While raising normal feedstuff, add and press the corresponding medicine of rat body weight, and weigh weekly a body weight, to facilitate administration, be administered
Mode is gavage, and dose is the many twenty alcohol 6mg of every Kg body weight every day, lovastatin group every Kg every day body weight 6mg, policosanol sheet group
Dose is every Kg body weight 6mg every day.After 12nd week terminates, the blood sampling of fasting 12h orbital vein measures TC (total gallbladder of the serum of rat
Sterin), LDL-C (low-density lipoprotein cholesterol), HDL-C (HDL-C), TG (triglyceride), result is such as
Shown in table 2:
Table 2 results of animal contrasts
TC: T-CHOL；LDL-C: low-density lipoprotein cholesterol；HDL-C: HDL-C；TG: glycerol
Three esters.
Indices data all represent with mmol/l, representMany twenty alcohol A groups, many twenty alcohol B groups, many twenty alcohol C groups, Lip river
Cut down statin group, each group data of policosanol sheet group compare with hyperlipidemia model group that there were significant differences property (P < 0.05), hyperlipidemia model
The property (P < 0.05) that compares with blank group that there were significant differences.
From the results shown in Table 2: gained high fatty alcohol of the present invention is reducing T-CHOL, low density lipoprotein, LDL gallbladder
Sterin and glycerol aspect are better than lovastatin, and HDL-C has a notable rising, and lovastatin increasing high density
The effect of lipoprotein cholesterol is the most inconspicuous.And reducing T-CHOL, low density lipoprotein, LDL with marketed drugs policosanol sheet
Cholesterol and glycerol aspect, and high density lipoprotein increasing cholesterol has close effect.
Although, used general explanation, detailed description of the invention and test, the present invention made detailed retouching
Stating, but on the basis of the present invention, can make some modifications or improvements it, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Scope.
Claims (10)
1. the method preparing senior fat primary alcohol mixture with cerosin, it is characterised in that include cerosin organic solvent
After dissolving, under the effect of alkali and phase transfer catalyst, carry out the step of saponification.
Method the most according to claim 1, it is characterised in that: described phase transfer catalyst is Polyethylene Glycol；Preferably molecule
Amount is the Polyethylene Glycol of 200-2000, further preferably uses PEG400, Macrogol 600, polyethylene glycol-800, poly-second
Glycol 1000, one or more in polyethylene glycol 1500.
Method the most according to claim 1 and 2, it is characterised in that: the consumption of described phase transfer catalyst is described alkali
The 1-6% of mole, preferably 2-3%.
Method the most according to claim 3, it is characterised in that: described organic solvent is selected from alkyl chloride hydro carbons or carbon number
One or more in the alcohols solvent of 1～4；It is preferably dichloromethane or ethanol；It is further preferred that described organic solvent
Consumption is 2-8L/kg cerosin.
5. according to the method described in claim 1 or 2 or 4, it is characterised in that: described alkali is selected from sodium hydroxide, potassium hydroxide, hydrogen
One or more in calcium oxide, it is preferable that the consumption of described alkali is 0.05-0.3 times of cerosin weight.
Method the most according to claim 5, it is characterised in that: reaction system also includes that water, the consumption of described water are alkali weight
0.3-0.7 times of amount.
7. according to the method described in claim 1 or 2 or 4 or 6, it is characterised in that: the condition of described saponification is: in 40-
80 DEG C of stirring reaction 30-100min.
Method the most according to claim 7, it is characterised in that also include the reactant liquor after saponification is carried out post processing
Step, described post processing is: washes reactant liquor with water, separates organic facies, with activated carbon to described organic facies decolour after, reclaim
Solvent to obtain crude product to dry, with ethanol described crude product is carried out recrystallization and get final product；
Preferably, described recrystallization is: add the ratio of 5-20mL ethanol in every gram of crude product, adds ethanol in described crude product,
And in 55-78 DEG C of dissolving, it is cooled to room temperature, stand crystallize and get final product.
9. the senior fat primary alcohol mixture that the method described in any one of claim 1-8 prepares.
10. the senior fat primary alcohol mixture that the method described in any one of claim 1-8 prepares is at preparation treatment fall blood
Application in fat and/or anticholesteremic agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610573043.8A CN106187677B (en) | 2016-07-19 | 2016-07-19 | A kind of method and application preparing senior fat primary alcohol mixture with cerosin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610573043.8A CN106187677B (en) | 2016-07-19 | 2016-07-19 | A kind of method and application preparing senior fat primary alcohol mixture with cerosin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106187677A true CN106187677A (en) | 2016-12-07 |
| CN106187677B CN106187677B (en) | 2019-03-26 |
Family
ID=57494690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610573043.8A Active CN106187677B (en) | 2016-07-19 | 2016-07-19 | A kind of method and application preparing senior fat primary alcohol mixture with cerosin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106187677B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110872207A (en) * | 2019-11-21 | 2020-03-10 | 武义县震威生物科技有限公司 | Production process for extracting high-carbon alcohol from natural wax and production line thereof |
| CN111840321A (en) * | 2020-09-08 | 2020-10-30 | 山西凯瑞森生物科技有限公司 | Polyunsaturated fatty acid calcium zinc ferrous magnesium composite preparation and preparation method and application thereof |
| CN117986089A (en) * | 2024-02-02 | 2024-05-07 | 广州绿徽新材料研究院有限公司 | Preparation method of ultra-high purity nanoscale octacosanol dispersoid |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1074435A (en) * | 1992-01-15 | 1993-07-21 | 国家科学研究中心 | By the method that makes mixture of higher aliphatic alcohols in the sugar-cane wax |
| CN1084844A (en) * | 1992-09-29 | 1994-04-06 | 达尔马实验室有限公司 | Higher primary aliphatic alcohols mixture, its method and pharmaceutical application thereof of producing by sugar-cane wax |
| CN1321627A (en) * | 2000-04-30 | 2001-11-14 | 雷少华 | Method for extracting high-grade primary fat alcohol mixture by using cerosin |
| US20050131078A1 (en) * | 2003-01-31 | 2005-06-16 | Unigen Pharmaceuticals, Inc. | Polycosanols from ericerus pela wax |
| CN101475876A (en) * | 2008-01-02 | 2009-07-08 | 上海中远化工有限公司 | Preparation of rice bran wax calcium soap |
| CN101870637A (en) * | 2009-04-25 | 2010-10-27 | 中山百灵生物技术有限公司 | Technology for extracting and preparing policosanol |
-
2016
- 2016-07-19 CN CN201610573043.8A patent/CN106187677B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1074435A (en) * | 1992-01-15 | 1993-07-21 | 国家科学研究中心 | By the method that makes mixture of higher aliphatic alcohols in the sugar-cane wax |
| CN1030763C (en) * | 1992-01-15 | 1996-01-24 | 国家科学研究中心 | Method for obtaining a mixture of higher aliphatic alcohols from sugar cane wax |
| CN1084844A (en) * | 1992-09-29 | 1994-04-06 | 达尔马实验室有限公司 | Higher primary aliphatic alcohols mixture, its method and pharmaceutical application thereof of producing by sugar-cane wax |
| CN1321627A (en) * | 2000-04-30 | 2001-11-14 | 雷少华 | Method for extracting high-grade primary fat alcohol mixture by using cerosin |
| US20050131078A1 (en) * | 2003-01-31 | 2005-06-16 | Unigen Pharmaceuticals, Inc. | Polycosanols from ericerus pela wax |
| CN101475876A (en) * | 2008-01-02 | 2009-07-08 | 上海中远化工有限公司 | Preparation of rice bran wax calcium soap |
| CN101870637A (en) * | 2009-04-25 | 2010-10-27 | 中山百灵生物技术有限公司 | Technology for extracting and preparing policosanol |
Non-Patent Citations (1)
| Title |
|---|
| 陆绍荣 等: "三相转移催化提取三十烷醇及其应用研究", 《化学研究与应用》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110872207A (en) * | 2019-11-21 | 2020-03-10 | 武义县震威生物科技有限公司 | Production process for extracting high-carbon alcohol from natural wax and production line thereof |
| CN111840321A (en) * | 2020-09-08 | 2020-10-30 | 山西凯瑞森生物科技有限公司 | Polyunsaturated fatty acid calcium zinc ferrous magnesium composite preparation and preparation method and application thereof |
| CN117986089A (en) * | 2024-02-02 | 2024-05-07 | 广州绿徽新材料研究院有限公司 | Preparation method of ultra-high purity nanoscale octacosanol dispersoid |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106187677B (en) | 2019-03-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101293811B (en) | Method for preparing advanced alkanol mixture with Chinese insect wax | |
| CN101386562A (en) | Method for preparing policosanol mixture by nonsolvent reduction method | |
| CN106187677A (en) | A kind of method and application preparing senior fat primary alcohol mixture with cerosin | |
| CN101845362B (en) | Method for gathering oleic acid from tea-seed oil | |
| CN101607977B (en) | Method for extracting and purifying natural phytosterol from oil deodorization distillate residual oil and technique thereof | |
| CN102757988A (en) | Preparation method of 1,3-dioleoyl-2-palmitoyl triglyceride | |
| CN102827213B (en) | A kind of method being prepared sucrose fatty ester by discarded animal-plant oil | |
| CN102731608A (en) | Preparation method of tea saponin ester succinate surfactant and product thereof | |
| CN111961018B (en) | Preparation method of high-purity butylphthalide | |
| CN102516329A (en) | Gastrodin synthesizing method | |
| CN101701029A (en) | Method for extracting natural phytosterin from residual oil of vegetable fat deodorizing distillate | |
| CN102126941A (en) | Preparation method of euphorbia peplus plant extract for preparing antitumor medicament | |
| CN102876465A (en) | Method for preparing biodiesel by using kitchen waste oil | |
| CN102329272A (en) | Method for preparing quinocetone | |
| CN102093438A (en) | Process for synthesizing sucrose polyester by using rotating film transesterification flow reactor | |
| CN104672291A (en) | Preparation method of gallate phytosterol ester | |
| CN102212092A (en) | Preparation method for high-purity jasminoidin | |
| CN109294735A (en) | A kind of ethyl ester type fish oil refining processing technology | |
| CN101575340B (en) | Preparation method of ketorolac tromethamine | |
| CN101538306A (en) | Preparation method of phytosterin ester rich in oleic acid | |
| CN1687239A (en) | Method for preparing crystal of lycopene and concentrate | |
| CN100334103C (en) | Method for extracting phytosterol acetate from vegetable oil asphalt | |
| CN1580030A (en) | Method for synthesizing conjugated linoleic acid | |
| CN109134237B (en) | Production method of conjugated linoleic acid | |
| CN108753467A (en) | Using gutter oil as the method for raw material coproduction solid alcohol and epoxy gutter oil |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |