CN107365290A - The method that Malania Oleifera Oil prepares pentadacanolide - Google Patents
The method that Malania Oleifera Oil prepares pentadacanolide Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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Abstract
This application discloses the method that a kind of Malania Oleifera Oil in chemosynthesis technical field prepares pentadacanolide, comprise the following steps：Step 1: molecular distillation；Step 2: saponification filter wash；Step 3: recrystallization：Start dissolved to crystallize three times；Crystallization for the first time is using ether as solvent, and second of crystallization is by the use of acetone as solvent, and third time crystallization is by the use of petroleum ether as solvent, and by carrying out repeated recrystallize to aliphatic acid, final arrives pure white needle-like crystals nervonic acid；Step 4: ozonisation reduction；Step 5: esterification；Step 6: ring gathers, pentadacanolide is obtained.The present invention prepares pentadacanolide using the nervonic acid of high purity more than 95%, and because the purity of nervonic acid is high, impurity is less, is gathered by the ozonisation, reduction and ring of the nervonic acid to high-purity, is advantageous to obtain the pentadacanolide of high-purity.
Description
Technical field
The present invention relates to chemosynthesis technical field, and in particular to a kind of method that Malania Oleifera Oil prepares pentadacanolide.
Background technology
Malania oleifera, scientific name Malania oleifera et Lee, also known as after mountain paulownia fruit, Tieghemella heckelii Pierre, wild paulownia, kalimeris etc..It is blue or green
Dermatological department, woody Chang Green tallow trees.Tree trunk is straight, up to 20 meters, and tree-walk oval leaf, oblate spheroid tree fruit, is grown in 500- up to 40 centimetres
In 1640 meters of fertile Limestone Mountain mixed forests of moistening.South China production tung oil area town and country can be used as greening-tree, landscape tree, oil
Material tree plant.Autumn and winter harvest fruit, and frying eats into Malania Oleifera Oil and makees iundustrial oil.Tree trunk matter is close preferably to make timber.
Soap thing content is not 4% to Malania Oleifera Oil in Malania Oleifera Oil grease；Tetracosenoic acid, content 67%；Containing oleic acid
(12%) and the acid such as micro capric acid, laurate, myristic acid, palmitic acid, undeterminate composition are 14%.
Wherein tetracosenoic acid, also known as nervonic acid, molecular structural formula：H3(CH2)7CH=CH (CH2)13COOH, Yi Zhongbai
Color crystallizes, and relative molecular mass 366.6, can be dissolved in alcohol, not soluble in water, 39~40 DEG C of fusing point.It is manufacture pentadacanolide
Raw material, pentadacanolide, Cycloentadenolde, it is present in angelica levisticum Baillon root oil, molecular formula, C15H28O2, molecular weight
For 240.39, colourless liquid to white, needle-shaped crystals.With excellent young musk odor, fragrance is strong, persistently strong.36 DEG C of fusing point
More than, 280 DEG C of boiling point, it is dissolved in 6 volume ethanols or the ethanol of same volume 90% or oily spices.Main application is the various perfume (or spice) of modulation
The fixastive of material, to allocate the daily chemical essences such as perfumed soap, soap, detergent.In general chemistry preparation method is azelaic acid etc. through multistep
Suddenly 15 hydroxy-pentadecanoic acids are made, polymerize through decompression, circulated depolymerization and obtain.
Prior art prepares pentadacanolide also having using Malania Oleifera Oil, but is all first to isolate nervonic acid, existing
There is technology such as Hao Xuya to use urea adduct method to garlic in " the separating-purifying research of nervonic acid in Malania Oleifera Oil " paper
Nervonic acid in fruit oil is separated, and urea adduct method is dissolved urea in organic solvent, when adding aliphatic acid, urea
It is intermolecular that hexahedral structure is formed with hydrogen bond, spiral helicine inclusion compound framework is formed, because the diameter of saturated fatty acid is less than
The free space of framework, in crystallization process, the saturated fatty acid of straight chain or monounsaturated fat enter in framework, by urea
Inclusion, form inclusion compound and separate out.And polyunsaturated fatty acid is not easy by urea clathrate, based on above-mentioned principle, you can by unsaturation
Aliphatic acid (ester) separates with saturated fatty acid (ester), i.e., in Malania Oleifera Oil when, inclusion removes the aliphatic acid of the low-carbon such as oleic acid, from
And nervonic acid is isolated, and then pentadacanolide is prepared, the content of nervonic acid is only 65% in the crude product nervonic acid of extraction, other
Impurity is more, if directly to produce exaltolide, can produce more accessory substances, influences the yield of reaction.
The content of the invention
The invention is intended to provide a kind of method that pentadacanolide is prepared using Malania Oleifera Oil, solves the system of prior art
The problem of Preparation Method rate of recovery is low, and accessory substance is more.
The technical scheme is that the method that Malania Oleifera Oil prepares pentadacanolide, comprises the following steps：
Step 1: molecular distillation：Malania Oleifera Oil is first subjected to molecular distillation, vapo(u)rizing temperature is 150 DEG C, and distillation pressure is
11Pa, light component and heavy constituent are obtained, take light component standby；
Step 2: saponification filter wash：A, saponification：The alkali lye that concentration is 10% is added into retort, afterwards by Malania Oleifera Oil
Add in retort, stirring, be passed through and be steam heated to 70~80 DEG C, persistently add alkali lye, disappeared to fluid, reaction generation nerve
Acid sodium-salt saponification liquor；；B, oil removing：Saponification liquor cools down, and adds ether and neural acid sodium-salt saponification liquor is extracted, stand, separate upper strata
Ether solution, ether is reclaimed, Residual oil is discarded, stays saponification saline solution；C, acid out：Saponification saline solution is added to acid out tank, stirs and is added dropwise
The sulfuric acid that concentration is 10% is 6~7 to pH, separates out white and mixes acid out liquid；D, acid filtering：Mixing acid out liquid is put into and is covered with filter cloth
Filter pocket in, filtering reaction generation sodium sulphate remove wastewater disposal basin, filtrate is mixed acid, with hot wash mixed acid, is then air-dried
It is standby afterwards；
Step 3: recrystallization：A, ether dissolved：Acid will be mixed to be added in the ether of 3 times of weight, be dissolved as ether acid
Liquid, suction strainer go out immiscible acid (1), and ether acid solution, which is cooled at -10~-5 DEG C, to be crystallized, and suction strainer goes out brilliant sour (2), and ether mother liquor steams recovery
Ether, stay and steam spent acid (3)；B, acetone dissolved：Brilliant acid (2) is added in 3 times of weight acetones, is dissolved as acetone acid solution, suction strainer goes out
Immiscible acid (4), acetone acid solution, which is cooled at -10~-5 DEG C, to be crystallized, and suction strainer goes out brilliant sour (5), and acetone mother liquor steams recovery acetone, stays steaming
Spent acid (6)；C, petroleum ether dissolved：Brilliant acid (5) is added in 3 times of weight petroleum ethers, is dissolved as petroleum ether acid solution, suction strainer goes out insoluble
Sour (7), petroleum ether acid solution, which is cooled at -10~-5 DEG C, to be crystallized, and suction strainer goes out brilliant sour (8), and petroleum ether mother liquor steams recovery petroleum ether, stayed
Steam spent acid (9)；
Step 4: ozonisation reduction：A, ozonize：The crystalline substance acid 8 in step 3 is taken to be added to together with ethanol and petroleum ether
Stirred in ozone generator, solution temperature is down to 0 DEG C, and logical 3~4h of ozone obtains ozonizing feed liquid；B, reduce：Sodium hydroxide is molten
Liquid and tetrahydroborate potassium solution mixed preparing reducing solution, the reducing solution prepared are maintained the temperature at 20 DEG C, and ozone material is added dropwise
Liquid, obtain reducing feed liquid；C, liquid separation：Reduction feed liquid to be put into separator, stratification, upper strata is fluid, and lower floor is aqueous,
Fluid is distilled to obtain ethanol, petroleum ether and nonyl alcohol, and aqueous is sent into acid out groove, and the sulfuric acid for adding 10% separates out crystal, filters off salt
Liquid, hot wash air-dry that to obtain hydroxy-pentadecanoic acid standby；
Step 5: esterification：A, react：Hydroxy-pentadecanoic acid in methanol, the concentrated sulfuric acid and step 4 is added into reactor together
In, stirring, logical vapour heating simultaneously maintains the temperature at 70 DEG C, and 3~4h is reacted under infinite reflux；B, distill：Stop flowing back, steam methanol-water
Azeotropic liquid, 5% sodium carbonate liquor washing deacidification is added, with hot wash solution, layering stands, removes the wash water of bottom, stay
The thick ester in top is standby；C, recrystallize：Add ethanol and dissolve thick ester, filter insoluble matter, recrystallized at 0 DEG C, crystal is separated out, by crystalline substance
It is standby that body obtains hydroxy-pentadecanoic acid methacrylate powder after air-drying；
Step 6: ring gathers：A, react：Hydroxy-pentadecanoic acid methyl esters in dimethylbenzene and p-methyl benzenesulfonic acid and step 5 is added
Into the poly- tank of ring, stirring, reaction temperature is increased to 105 DEG C, flow back 20~25h of lower reaction, stops after steaming methanol-water azeotropic liquid
Only heat, b, neutralize separation：Add in 5% sodium carbonate liquor and wash, blowing adds water washing into separator, is layered quiet
Put, remove bottom saline solution, stay top dimethylbenzene lactones liquid standby；C, distill：Dimethylbenzene lactones liquid is sent into distillation still and distilled,
It is evaporated under reduced pressure after steaming dimethylbenzene under 128 DEG C and 133pa, it is standby obtains pentadacanolide crude product；D, recrystallize：By ring 15
Lactone crude product is added in the ethanol of 2 times of pentadacanolide crude product amounts, filtering, is crystallized at 0 DEG C, is separated out after crystal air-dries and is obtained
To pentadacanolide.
The working principle and beneficial effect of the present invention：The present invention uses the malania oleifera rich in nervonic acid as raw material, and is directed to
Tradition extraction from malania oleifera separates existing above mentioned problem during nervonic acid, using the first garlic after molecular distillation
Fruit oil separating heavy and light component, light component saponification generation saponification liquor, then saponification liquor is removed into the not miscellaneous oil of soap, by adding
Enter sulfuric acid acid out into fatty acid mixed, obtain pure mixing-in fat acid crystal after being air-dried by hot wash after filtering, afterwards
Start dissolved to crystallize three times；Crystallization for the first time is tied using ether as solvent, second of crystallization by the use of acetone as solvent, third time
Crystalline substance is by the use of petroleum ether as solvent, and by carrying out repeated recrystallize to aliphatic acid, final arrives pure white needle-like crystals brilliant sour 8
(nervonic acid), through gas chromatographic analysis, the purity of nervonic acid is more than 90%.Recycle the nervonic acid of high purity more than 95%
Pentadacanolide is prepared, because the purity of nervonic acid is high, impurity is less, passes through the ozonisation of the nervonic acid to high-purity, reduction
Gather with ring, be advantageous to obtain the pentadacanolide of high-purity.The process solvent for use, it is low boiling point, easy reclaim reagent, is free of
Heavy metal and the difficult pollutant removed, repeat and utilize, reduce environmental pollution, reduce production cost.
Further, the crystallization temperature in the step 3 is -5 DEG C.Crystallize at such a temperature, the purity of nervonic acid can carry
It is high by 3%.
Further, during the step 3 petroleum ether dissolved, 10% absolute ethyl alcohol is added in petroleum ether and mixed
Petroleum ether acid solution, brilliant acid 5 is added in the mixing petroleum ether acid solution of 3 times of weight afterwards, is cooled at -5 DEG C and crystallizes.Add anhydrous
Crystallized at such a temperature after ethanol, the purity of nervonic acid can improve 5%.
Brief description of the drawings
Fig. 1 is the schematic flow sheet for the method that Malania Oleifera Oil of the present invention prepares pentadacanolide.
Embodiment
Below by embodiment, the present invention is further detailed explanation：
Embodiment 1：The method that Malania Oleifera Oil prepares pentadacanolide, reaction equation are as follows：
As shown in figure 1, comprise the following steps：
Step 1: molecular distillation：Malania Oleifera Oil is first subjected to molecular distillation, vapo(u)rizing temperature is 150 DEG C, and distillation pressure is
11Pa, light component and heavy constituent are obtained, take its light component standby：
Step 2: saponification filter wash：A, saponification：The sodium hydroxide that concentration is 10% is added into retort, afterwards by step
One light component is added in retort, stirring, is passed through and is steam heated to 70~80 DEG C, persistently adds the hydroxide that concentration is 10%
Sodium, disappeared to a large amount of fluid, reaction generates neural acid sodium-salt saponification liquor, now the pH=8 of solution；B, oil removing：Saponification liquor cools down,
Soap oil is not miscellaneous in addition ether extraction saponification liquid, stands, and separates upper strata ether solution, reclaims ether, discards Residual oil, stay saponification salt
Liquid；C, acid out：Saponification saline solution is added to acid out tank, the sulfuric acid that dropwise addition concentration is 10% under stirring to pH is 6~7, is separated out white
Color contamination and acid out liquid；D, acid filtering：Acid out liquid will be mixed to be put into the filter pocket for being covered with filter cloth, metabisulfite solution is filtered off and remove wastewater disposal basin,
Collect standby after mixing acid heat water washing air-dries；
Step 3: recrystallization：A, ether dissolved：Mix sour be added in the ether of 3 times of weight and be dissolved as ether acid solution, inhale
Immiscible acid 1 is filtered out, ether acid solution, which is cooled at -5 DEG C, to be crystallized, and suction strainer goes out brilliant acid 2, and ether mother liquor steams recovery ether, stays ether female
Liquid spent acid 3；B, acetone dissolved：Brilliant acid 2, which is added in 3 times of weight acetones, is dissolved as acetone acid solution, and suction strainer goes out immiscible acid 4, acetone
Acid solution, which is cooled at -5 DEG C, to be crystallized, and suction strainer goes out brilliant acid 5, and acetone mother liquor steams recovery acetone；Stay acetone mother liquor spent acid 6；C, petroleum ether
Dissolved：10% absolute ethyl alcohol is added in petroleum ether and obtains mixing petroleum ether acid solution, brilliant acid 5 is added to 3 times of weights afterwards
In the mixing petroleum ether acid solution of amount, suction strainer goes out immiscible acid 7, and petroleum ether acid solution, which is cooled at -5 DEG C, to be crystallized, and suction strainer goes out brilliant acid 8, oil
Ether mother liquor steams recovery petroleum ether, stays petroleum ether spent acid 9；
Step 4: ozonisation reduction：A, ozonize：Take the crystalline substance acid 8 of the 21.6kg in step 3 and 20kg ethanol and
20kg petroleum ether is added in ozone generator together to be stirred, and solution temperature is down to 0 DEG C, and logical 3~4h of ozone is ozonized
Feed liquid；B, reduce：By 3kg10% sodium hydroxide solution and 3.8kg tetrahydroborate potassium solution mixed preparing reducing solution, prepare
Good reducing solution is maintained the temperature at 20 DEG C, and ozonisation feed liquid is added dropwise, and obtains reducing feed liquid；C, liquid separation：Will reduction feed liquid put to
In separator, stratification, upper strata is fluid, and lower floor is aqueous, and fluid distills at 80 DEG C obtains ethanol and petroleum ether, solution
Continue to be evaporated under reduced pressure, distilled at 95~100 DEG C, under 1600Pa and obtain nonyl alcohol；Aqueous is sent into acid out groove, adds 10% sulphur
Acid out goes out crystal, filters off saline solution, the air-dried hydroxy-pentadecanoic acid that obtains of hot wash is standby, yield 65%；
Step 5: esterification：A, react：The hydroxyl of the methanol that 4 times are measured, the 25.6kg in the 1kg concentrated sulfuric acid and step 4
Pentadecanoic acid is added in reactor together, stirring, and logical vapour heating simultaneously maintains the temperature at 70 DEG C, and 3~4h is reacted under infinite reflux；B, steam
Evaporate：Stop flowing back, steam methanol-water azeotropic liquid, add 5% sodium carbonate liquor washing deacidification, it is quiet with hot wash solution, layering
Put, remove the wash water of bottom, stay the thick ester in top standby；C, recrystallize：Add ethanol and dissolve thick ester, insoluble matter is filtered, at 0 DEG C
Recrystallization, separate out standby, the yield 75% that obtains hydroxy-pentadecanoic acid methyl esters after crystal air-dries；
Step 6: ring gathers：A, react：By the 20.2kg in 40kg dimethylbenzene and 1kg p-methyl benzenesulfonic acid and step 5
Hydroxy-pentadecanoic acid methyl esters is standby to be added in the poly- tank of ring, is stirred, and temperature is increased into 105 DEG C, and flow back 20~25h of lower reaction, steams
Stop heating after methanol-water azeotropic liquid, b, neutralize separation：Add 5% sodium carbonate liquor in and wash, blowing into separator,
Add water washing, layering is stood, and is removed bottom saline solution, is stayed top dimethylbenzene lactones liquid standby；C, distill：Dimethylbenzene lactones liquid is sent
Enter in distillation still and distill, be evaporated under reduced pressure after steaming dimethylbenzene under 128 DEG C and 133pa, it is standby to obtain pentadacanolide crude product；d、
Recrystallization：Pentadacanolide crude product is added in the ethanol of 2 times of pentadacanolide crude product amounts, filters, crystallized at 0 DEG C,
Separate out after crystal air-dries and obtain 15.6kg pentadacanolide, yield 85%.
100g Malania Oleifera Oil is chosen as experimental raw, is entered respectively using urea adduct method and embodiments of the invention 1
Row experiment contrast is analyzed, and conclusion is as follows：
Table 1 is that purity and the rate of recovery are analyzed
Referring to above-mentioned purity and rate of recovery value, the purity of the nervonic acid of embodiments of the invention 1 is far above of the prior art
The nervonic acid purity of urea adduct method, therefore when subsequent reactions prepare pentadacanolide, the yield of embodiment 1 is higher, its yield
Minimum value be more than comparative example peak.
Above-described is only embodiments of the invention, and the general knowledge such as known concrete structure and characteristic is not made herein in scheme
Excessive description., without departing from the structure of the invention, can be with it should be pointed out that for those skilled in the art
Several modifications and improvements are made, these should also be considered as protection scope of the present invention, and these are implemented all without the influence present invention
Effect and practical applicability.The scope of protection required by this application should be based on the content of the claims, in specification
The records such as embodiment can be used for the content for explaining claim.
Claims (3)
1. the method that Malania Oleifera Oil prepares pentadacanolide, it is characterised in that comprise the following steps：
Step 1: molecular distillation：Malania Oleifera Oil is first subjected to molecular distillation, vapo(u)rizing temperature is 150 DEG C, distillation pressure 11Pa,
Light component and heavy constituent are obtained, takes light component standby；
Step 2: saponification filter wash：A, saponification：The alkali lye that concentration is 10% is added into retort, is afterwards added Malania Oleifera Oil anti-
Answer in tank, stir, be passed through and be steam heated to 70 ~ 80 DEG C, persistently add alkali lye, disappeared to fluid, reaction generates neural acid sodium-salt
Saponification liquor；；B, oil removing：Saponification liquor cools down, and adds ether and neural acid sodium-salt saponification liquor is extracted, stand, separate upper strata ether solution,
Ether is reclaimed, Residual oil is discarded, stays saponification saline solution；C, acid out：Saponification saline solution is added to acid out tank, stirs and concentration is added dropwise and be
10% sulfuric acid is 6 ~ 7 to pH, separates out white and mixes acid out liquid；D, acid filtering：Mixing acid out liquid is put into the filter pocket for being covered with filter cloth
In, the sodium sulphate of filtering reaction generation removes wastewater disposal basin, and filtrate is mixed acid, standby after then air-drying with hot wash mixed acid；
Step 3: recrystallization：A, ether dissolved：Acid will be mixed to be added in the ether of 3 times of weight, ether acid solution is dissolved as, inhales
Immiscible acid (1) is filtered out, ether acid solution, which is cooled at -10 ~ -5 DEG C, to be crystallized, and suction strainer goes out brilliant sour (2), and ether mother liquor steams recovery ether,
Stay and steam spent acid (3)；B, acetone dissolved：Brilliant acid (2) is added in 3 times of weight acetones, is dissolved as acetone acid solution, suction strainer goes out immiscible acid
（4）, acetone acid solution, which is cooled at -10 ~ -5 DEG C, to be crystallized, and suction strainer goes out brilliant acid（5）, acetone mother liquor steams recovery acetone, stays steaming spent acid
（6）；C, petroleum ether dissolved：Brilliant acid (5) is added in 3 times of weight petroleum ethers, is dissolved as petroleum ether acid solution, suction strainer goes out immiscible acid
(7), petroleum ether acid solution is cooled at -10 ~ -5 DEG C and crystallized, and suction strainer goes out brilliant sour (8), and petroleum ether mother liquor steams recovery petroleum ether, stays steaming
Spent acid (9)；
Step 4: ozonisation reduction：A, ozonize：The crystalline substance acid 8 in step 3 is taken to be added to ozone together with ethanol and petroleum ether
Stirred in generator, solution temperature is down to 0 DEG C, and logical 3 ~ 4h of ozone obtains ozonizing feed liquid；B, reduce：Sodium hydroxide solution and four
Potassium borohydrid solution mixed preparing reducing solution, the reducing solution prepared are maintained the temperature at 20 DEG C, and ozonisation feed liquid is added dropwise, obtains
Reduce feed liquid；C, liquid separation：Reduction feed liquid is put into separator, stratification, upper strata is fluid, and lower floor is aqueous, and fluid steams
Evaporate to obtain ethanol, petroleum ether and nonyl alcohol, aqueous is sent into acid out groove, and the sulfuric acid for adding 10% separates out crystal, filters off saline solution, hot water
It is standby that laundry air-dry obtains hydroxy-pentadecanoic acid；
Step 5: esterification：A, react：Hydroxy-pentadecanoic acid in methanol, the concentrated sulfuric acid and step 4 is added in reactor together, stirred
Mix, logical vapour heating simultaneously maintains the temperature at 70 DEG C, and 3 ~ 4h is reacted under infinite reflux；B, distill：Stop flowing back, steam methanol-water azeotropic
Liquid, 5% sodium carbonate liquor washing deacidification is added, with hot wash solution, layering stands, removes the wash water of bottom, stay top thick
Ester is standby；C, recrystallize：Add ethanol and dissolve thick ester, filter insoluble matter, recrystallized at 0 DEG C, separate out crystal, crystal is air-dried
After to obtain hydroxy-pentadecanoic acid methacrylate powder standby；
Step 6: ring gathers：A, react：Hydroxy-pentadecanoic acid methyl esters in dimethylbenzene and p-methyl benzenesulfonic acid and step 5 is added to ring
In poly- tank, stir, reaction temperature is increased to 105 DEG C, flow back 20 ~ 25h of lower reaction, stops adding after steaming methanol-water azeotropic liquid
Heat, b, neutralize separation：Add in 5% sodium carbonate liquor and wash, blowing adds water washing into separator, and layering stands, gone
Except bottom saline solution, stay top dimethylbenzene lactones liquid standby；C, distill：Dimethylbenzene lactones liquid is sent into distillation still and distilled, is steamed
It is evaporated under reduced pressure after dimethylbenzene under 128 DEG C and 133pa, it is standby obtains pentadacanolide crude product；D, recrystallize：By pentadacanolide
Crude product is added in the ethanol of 2 times of pentadacanolide crude product amounts, filtering, is crystallized at 0 DEG C, is separated out after crystal air-dries and is obtained ring
Omega-pentadecanolide.
2. the method that Malania Oleifera Oil according to claim 1 prepares pentadacanolide, it is characterised in that：In the step 3
Crystallization temperature be -5 DEG C.
3. the method that Malania Oleifera Oil according to claim 2 prepares pentadacanolide, it is characterised in that：The step 3 stone
During oily ether dissolved, 10% absolute ethyl alcohol is added in petroleum ether and obtains mixing petroleum ether acid solution, brilliant acid 5 is added to 3 afterwards
In the mixing petroleum ether acid solution of times weight, it is cooled at -5 DEG C and crystallizes.
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| CN1349988A (en) * | 2001-09-03 | 2002-05-22 | 广西大学 | Exaltolide preparing process from garlic oil |
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Application publication date: 20171121 |