CN108658779A - A method of utilizing aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters - Google Patents

A method of utilizing aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters Download PDF

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CN108658779A
CN108658779A CN201810818225.6A CN201810818225A CN108658779A CN 108658779 A CN108658779 A CN 108658779A CN 201810818225 A CN201810818225 A CN 201810818225A CN 108658779 A CN108658779 A CN 108658779A
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aspergillus niger
extraction
acid dimethyl
acetone
dimethyl esters
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李祝
张素
冉江
肖洋
唐婧红
张钦语
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Guizhou University
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Guizhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/16—Separation; Purification; Stabilisation; Use of additives

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  • Preparation Of Compounds By Using Micro-Organisms (AREA)
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Abstract

The invention discloses a kind of methods using 5 nitroisophthalic acid dimethyl ester of aspergillus niger separation and Extraction, it is that aspergillus niger extracting solution is made with acetone extraction in the conidia powder of aspergillus niger, and medicinal extract is made after concentrating aspergillus niger extracting solution, 5 nitroisophthalic acid dimethyl esters are can be prepared by after medicinal extract is chromatographed；The aspergillus niger is aspergillus niger xj, and preserving number is：CCTCC NO：M 206021, it is entitled：Aspergillus niger xj (Aspergillus niger xj).The characteristics of present invention prepares 5 nitroisophthalic acid dimethyl esters and belongs to a kind of biological source, and cheap and easy to get with substrate, extraction process is simple, easy, and production process is environmentally friendly, dissolvent residual is few, pollution is low, culture substrate is easy to get.

Description

A method of utilizing aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters
Technical field
It is especially a kind of to utilize aspergillus niger point the present invention relates to a kind of method of extraction 5- nitroisophthalic acid dimethyl esters Method from extraction 5- nitroisophthalic acid dimethyl esters.
Background technology
Aspergillus niger (Aspergillus niger) belongs to a Common Species in fungi, can be in wider temperature and pH It survives, is distributed widely in grain all over the world, plant product and soil under range and lower humidity.Aspergillus niger conduct Generally accepted safety (GRAS) strain of U.S. Food and Drug Administration (U.S.FDA) certification, is widely used in industrial life Organic acid, enzyme are produced, there is huge market potential value.Aspergillus Niger citric acid, gluconic acid, gallic acid, oxalic acid etc., production It is mainly amylase, catalase, cellulase, pectase, acid protease in terms of enzyme.Moreover, the crowd of aspergillus niger More metabolites all have a variety of significant application values.
5- nitroisophthalic acid dimethyl esters, also known as 5- nitros dimethylisophthalate, molecular formula C10H7NO6, English name Referred to as Dimethyl5-nitroisophthalate (DM-NIP).5- nitroisophthalic acid dimethyl esters are a kind of fine chemistry industries Intermediate is mainly used for the industries such as medicine, film, fiber, leather, it is also possible to make the developer of medical X-film, complementary color inhibits Agent etc..
5- nitroisophthalic acid dimethyl esters have the advantages that water solubility is big, viscosity is small, osmotic pressure is low etc., can be used to synthesize and examine Disconnected medication Iothalamic Acid can also be used to synthesis nonionic X- for radiographies such as angiocarpy, abdominal aorta, renal plevis, the cerebrovasculars CT contrast agent Iohexols.Preparation about 5- nitroisophthalic acid dimethyl esters is very early it has been reported that industrially prepared at present Mainly by 5- nitroisophthalic acids (5-Nitro-iso-phthalate, NIP) and methanol in H2SO4In the presence of be esterified and obtain, Biological source there is no to report.
Invention content
The object of the present invention is to provide a kind of sides using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters Method.The present invention prepares 5- nitroisophthalic acid dimethyl esters and belongs to a kind of biological source, cheap and easy to get with substrate, extracts work The characteristics of skill is simple, easy, and production process is environmentally friendly, dissolvent residual is few, pollution is low, culture substrate is easy to get.
Technical scheme of the present invention：A method of using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, It is aspergillus niger extracting solution to be made with acetone extraction in the conidia powder of aspergillus niger, and medicinal extract is made after aspergillus niger extracting solution is concentrated, It can be prepared by 5- nitroisophthalic acid dimethyl esters after medicinal extract is chromatographed；The aspergillus niger is aspergillus niger xj, and preserving number is： CCTCC NO：M 206021, it is entitled：Aspergillus niger xj (Aspergillus niger xj), (preservation address：Wuhan, China is military Chinese university).
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, the method specific steps It is as follows：
1) preparation of medicinal extract：Aspergillus niger spore powder is obtained into aspergillus niger extracting solution with acetone extraction, and the extracting solution is concentrated, Obtain medicinal extract；
2) silica gel column chromatography：Silica gel column chromatography is obtained with petroleum ether wet method dress post, the medicinal extract acetone in step (1) is molten Agent dissolving and and silica gel mixed sample, volatilize dry method loading after solvent；Use petroleum ether：Acetone gradient elution, Fractional Collections eluent are thin Tracing detection is analysed layer by layer, merges same composition, concentration；
3) reversed column chromatography：Polarity moderate enriched fractions acetone solvent dissolving and silica gel mixed sample, are waved in selecting step (2) Reversed silicagel column in wet method, is used in combination pure water after dry solvent：Acetone gradient elution, Fractional Collections eluent, thin-layer chromatography tracking Detection merges same composition, concentration；
4) Sephadex LH-20 gel filtration chromatographies：By in step (3) at the preferable enriched fractions chloroform of property：Methanol Weight ratio is 1:1 solvent dissolving, upper chloroform：Methanol weight ratio is 1:1 gel column, uses chloroform：Methanol elutes, and collects elution Liquid, thin-layer chromatography tracing detection merge same composition, are concentrated to give target crude product；
5) silica gel column chromatography again：Target crude product in step (4) is subjected to silicagel column processing again；Hexamethylene is used in combination：Third Ketone elutes, and collects eluent, and thin-layer chromatography tracing detection merges same composition, and TLC chromatographies are shown as one-component, and concentration is dry The dry micro-yellow powder that obtains is to get 5- nitroisophthalic acid dimethyl esters.
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters in the step 1), is By aspergillus niger spore powder acetone with 1：4 weight ratio is extracted 3 times under the conditions of 50-100 DEG C of temperature, pressure 0-1.0MPa Aspergillus niger extracting solution, time are each 3h.
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, the concentration refer to using Rotary Evaporators revolving to organic solvent under conditions of 40-60 DEG C of temperature, pressure are 0.04-0.06MPa volatilizes.
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, it is described with silica gel mixed sample in Silica gel size be 200-300 mesh.
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, it is described in step 2) Use petroleum ether：Acetone gradient elution is successively by petroleum ether：Acetone=1:0、40:1、20:1、10:1、5:1、2:1、1:1 and 0:1 It is eluted.
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, it is described in step 3) Use pure water：Acetone gradient elution is successively by pure water：Acetone=100：0、90:10、80:20、70:30、60:40、50: 50、40:60、30:70、20:80、10:90、0:100 are eluted.
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, it is described in step 4) Use chloroform：Methanol elution is by chloroform：Methanol=1：1 is eluted.
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, it is described in step (5) Use hexamethylene：Acetone elution is by hexamethylene：Acetone=3：1 is eluted.
Method above-mentioned using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters is washed in the elution The flow velocity of de- agent is 15mL/min.
Beneficial effects of the present invention
Compared with prior art：
1, the present invention prepares 5- nitroisophthalic acid dimethyl esters using the conidia powder of aspergillus niger, and it is next to belong to a kind of biology Source can provide a new way to solve 5- nitroisophthalic acid dimethyl esters source.
2, the conidia powder of aspergillus niger (Aspergillus niger xj) of the invention is from the horse's mouth, and substrate is cheap and easy to get； And to the wide adaptation range of the natural environmental conditions such as temperature, pH, extraction process is simple, easy, is also easy to cultivate and preserve.
3, in production process of the present invention, separating and extracting process is simple, reproducible, process environmental protection, and dissolvent residual is few and easy Recycling, reduces the consumption of the energy and the discharge of exhaust gas, greatly reduces environmental pollution.
The identification of aspergillus niger (Aspergillusnigerxj) extract 5- nitroisophthalic acid dimethyl esters：
1. the preparation of sample
After taking above-mentioned gained micro-yellow powder to sieve with 100 mesh sieve, using EI-MS to the sample and 5- nitroisophthalic acids Dimethyl ester standard specimen carries out wave spectrum analysis analysis
2. EI-MS analysis conditions
Mass Spectrometry Conditions：Ion source is the sources EI；230 DEG C of ion source temperature；150 DEG C of quadrupole rod temperature；Electron energy 70eV；Hair 34.6 μ A of radio stream；Multiplier voltage 1624V；280 DEG C of interface temperature；29~500amu of mass range；The solvent delay time： 5.0min。
3. conclusion：It is detected by EI-MS, is obtained from aspergillus niger (Aspergillus niger xj) conidia powder separation and Extraction Sample Rf values it is consistent with standard items, the monomeric compound be 5- nitroisophthalic acid dimethyl esters, structure be (Dimethyl 5-nitro-isophthalate).The result is shown in Figure 1.
Description of the drawings
Fig. 1 is the 5- nitroisophthalic acid dimethyl ester EI-MS mass spectral analysis figures of the method for the present invention extraction.
Fig. 2 is the structural formula of the 5- nitroisophthalic acid dimethyl esters EI-MS of the method for the present invention extraction.
Specific implementation mode
With reference to embodiment, the present invention is further illustrated, but is not intended as the foundation limited the present invention.
The embodiment of the present invention
Embodiment 1：A method of using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, steps are as follows：
1) preparation of medicinal extract：By aspergillus niger spore powder acetone with 1：4 weight ratio, in 75 DEG C of temperature, pressure 0.5MPa Under the conditions of extract 3 times aspergillus niger extracting solution, the time be each 3h, and by the extracting solution using Rotary Evaporators in temperature 50 DEG C, pressure rotate and volatilized to organic solvent under conditions of being 0.05MPa, obtain medicinal extract；
2) silica gel column chromatography：Silica gel column chromatography is obtained with petroleum ether wet method dress post, the medicinal extract acetone in step (1) is molten Agent is dissolved and the silica gel mixed sample with size for 250 mesh, volatilizes dry method loading after solvent；Petroleum ether is pressed successively：Acetone=1:0、40: 1、20:1、10:1、5:1、2:1、1:1 and 0:1 is eluted, Fractional Collections eluent, thin-layer chromatography tracing detection, is merged identical Component uses Rotary Evaporators to be rotated to organic solvent under conditions of temperature 50 C, pressure is 0.05MPa and volatilizes；
3) reversed column chromatography：The moderate enriched fractions acetone solvent dissolving of polarity and size are 250 mesh in selecting step (2) Silica gel mixed sample, volatilize after solvent reversed silicagel column in wet method, and press pure water successively：Acetone=100：0、90:10、80:20、 70:30、60:40、50:50、40:60、30:70、20:80、10:90、0:100 are eluted, Fractional Collections eluent, thin layer Analyse tracing detection, merge same composition, use Rotary Evaporators rotated under conditions of temperature 50 C, pressure is 0.05MPa to Organic solvent volatilizes；
4) Sephadex LH-20 gel filtration chromatographies：By in step (3) at the preferable enriched fractions chloroform of property：Methanol Weight ratio is 1:1 solvent dissolving, upper chloroform：Methanol weight ratio is 1:1 gel column, by chloroform：Methanol=1：1 is washed It is de-, collect eluent, thin-layer chromatography tracing detection merges same composition, use Rotary Evaporators temperature 50 C, pressure for Revolving is volatilized to organic solvent under conditions of 0.05MPa, obtains target crude product；
5) silica gel column chromatography again：Target crude product in step (4) is subjected to silicagel column processing again；And press hexamethylene：Third Ketone=3：1 is eluted, and eluent is collected, and thin-layer chromatography tracing detection merges same composition, and TLC chromatographies are shown as single group Point, be concentrated and dried micro-yellow powder to get 5- nitroisophthalic acid dimethyl esters.
In above-mentioned steps, when elution, the flow velocity of eluant, eluent is 15mL/min.
Embodiment 2：A method of using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, steps are as follows：
1) preparation of medicinal extract：By aspergillus niger spore powder acetone with 1：4 weight ratio, in temperature 50 C, pressure 0MPa items Extracted under part 3 times aspergillus niger extracting solution, the time be each 3h, and by the extracting solution using Rotary Evaporators 40 DEG C of temperature, Pressure is rotated under conditions of being 0.04MPa and is volatilized to organic solvent, obtains medicinal extract；
2) silica gel column chromatography：Silica gel column chromatography is obtained with petroleum ether wet method dress post, the medicinal extract acetone in step (1) is molten Agent is dissolved and the silica gel mixed sample with size for 200 mesh, volatilizes dry method loading after solvent；Petroleum ether is pressed successively：Acetone=1:0、40: 1、20:1、10:1、5:1、2:1、1:1 and 0:1 is eluted, Fractional Collections eluent, thin-layer chromatography tracing detection, is merged identical Component uses Rotary Evaporators to be rotated to organic solvent under conditions of 40 DEG C of temperature, pressure is 0.04MPa and volatilizes；
3) reversed column chromatography：The moderate enriched fractions acetone solvent dissolving of polarity and size are 200 mesh in selecting step (2) Silica gel mixed sample, volatilize after solvent reversed silicagel column in wet method, and press pure water successively：Acetone=100：0、90:10、80:20、 70:30、60:40、50:50、40:60、30:70、20:80、10:90、0:100 are eluted, Fractional Collections eluent, thin layer Analyse tracing detection, merge same composition, use Rotary Evaporators rotated under conditions of 40 DEG C of temperature, pressure is 0.04MPa to Organic solvent volatilizes；
4) Sephadex LH-20 gel filtration chromatographies：By in step (3) at the preferable enriched fractions chloroform of property：Methanol Weight ratio is 1:1 solvent dissolving, upper chloroform：Methanol weight ratio is 1:1 gel column, by chloroform：Methanol=1：1 is washed It is de-, collect eluent, thin-layer chromatography tracing detection merges same composition, use Rotary Evaporators 40 DEG C of temperature, pressure for Revolving is volatilized to organic solvent under conditions of 0.04MPa, obtains target crude product；
5) silica gel column chromatography again：Target crude product in step (4) is subjected to silicagel column processing again；And press hexamethylene：Third Ketone=3：1 is eluted, and eluent is collected, and thin-layer chromatography tracing detection merges same composition, and TLC chromatographies are shown as single group Point, be concentrated and dried micro-yellow powder to get 5- nitroisophthalic acid dimethyl esters.
In above-mentioned steps, when elution, the flow velocity of eluant, eluent is 15mL/min.
Embodiment 3：A method of using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, steps are as follows：
1) preparation of medicinal extract：By aspergillus niger spore powder acetone with 1：4 weight ratio, in 100 DEG C of temperature, pressure 1.0MPa Under the conditions of extract 3 times aspergillus niger extracting solution, the time be each 3h, and by the extracting solution using Rotary Evaporators in temperature 60 DEG C, pressure rotate and volatilized to organic solvent under conditions of being 0.06MPa, obtain medicinal extract；
2) silica gel column chromatography：Silica gel column chromatography is obtained with petroleum ether wet method dress post, the medicinal extract acetone in step (1) is molten Agent is dissolved and the silica gel mixed sample with size for 300 mesh, volatilizes dry method loading after solvent；Petroleum ether is pressed successively：Acetone=1:0、40: 1、20:1、10:1、5:1、2:1、1:1 and 0:1 is eluted, Fractional Collections eluent, thin-layer chromatography tracing detection, is merged identical Component uses Rotary Evaporators to be rotated to organic solvent under conditions of temperature 60 C, pressure is 0.06MPa and volatilizes；
3) reversed column chromatography：The moderate enriched fractions acetone solvent dissolving of polarity and size are 300 mesh in selecting step (2) Silica gel mixed sample, volatilize after solvent reversed silicagel column in wet method, and press pure water successively：Acetone=100：0、90:10、80:20、 70:30、60:40、50:50、40:60、30:70、20:80、10:90、0:100 are eluted, Fractional Collections eluent, thin layer Analyse tracing detection, merge same composition, use Rotary Evaporators rotated under conditions of temperature 60 C, pressure is 0.06MPa to Organic solvent volatilizes；
4) Sephadex LH-20 gel filtration chromatographies：By in step (3) at the preferable enriched fractions chloroform of property：Methanol Weight ratio is 1:1 solvent dissolving, upper chloroform：Methanol weight ratio is 1:1 gel column, by chloroform：Methanol=1：1 is washed It is de-, collect eluent, thin-layer chromatography tracing detection merges same composition, use Rotary Evaporators temperature 60 C, pressure for Revolving is volatilized to organic solvent under conditions of 0.06MPa, obtains target crude product；
5) silica gel column chromatography again：Target crude product in step (4) is subjected to silicagel column processing again；And press hexamethylene：Third Ketone=3：1 is eluted, and eluent is collected, and thin-layer chromatography tracing detection merges same composition, and TLC chromatographies are shown as single group Point, be concentrated and dried micro-yellow powder to get 5- nitroisophthalic acid dimethyl esters.
In above-mentioned steps, when elution, the flow velocity of eluant, eluent is 15mL/min.

Claims (10)

1. a kind of method using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, it is characterised in that：It is by black song Aspergillus niger extracting solution is made with acetone extraction in mould conidia powder, and medicinal extract is made after aspergillus niger extracting solution is concentrated, by medicinal extract layer It can be prepared by 5- nitroisophthalic acid dimethyl esters after analysis；The aspergillus niger is aspergillus niger xj, and preserving number is：CCTCC NO：M 206021, it is entitled：Aspergillus niger xj (Aspergillus niger xj).
2. the method according to claim 1 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：The method is as follows：
1) preparation of medicinal extract：Aspergillus niger spore powder is obtained into aspergillus niger extracting solution with acetone extraction, and the extracting solution is concentrated, must be soaked Cream；
2) silica gel column chromatography：Silica gel column chromatography is obtained with petroleum ether wet method dress post, the medicinal extract acetone solvent in step (1) is molten Solve and and silica gel mixed sample, volatilize dry method loading after solvent；Use petroleum ether：Acetone gradient elution, Fractional Collections eluent, thin layer Tracing detection is analysed, same composition, concentration are merged；
3) reversed column chromatography：Polarity moderate enriched fractions acetone solvent dissolving and silica gel mixed sample, volatilize molten in selecting step (2) Reversed silicagel column in wet method, is used in combination pure water after agent：Acetone gradient elution, Fractional Collections eluent, thin-layer chromatography tracing detection, Merge same composition, concentration；
4) Sephadex LH-20 gel filtration chromatographies：By in step (3) at the preferable enriched fractions chloroform of property：Methanol weight Than being 1:1 solvent dissolving, upper chloroform：Methanol weight ratio is 1:1 gel column, uses chloroform：Methanol elutes, and collects eluent, Thin-layer chromatography tracing detection merges same composition, is concentrated to give target crude product；
5) silica gel column chromatography again：Target crude product in step (4) is subjected to silicagel column processing again；Hexamethylene is used in combination：Acetone is washed It is de-, eluent is collected, thin-layer chromatography tracing detection merges same composition, and TLC chromatographies are shown as one-component, are concentrated and dried Micro-yellow powder is to get 5- nitroisophthalic acid dimethyl esters.
3. the method according to claim 2 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：It is by aspergillus niger spore powder acetone with 1 in the step 1)：4 weight ratio, in 50-100 DEG C of temperature, pressure 0- Aspergillus niger extracting solution is extracted 3 times to obtain under the conditions of 1.0MPa, the time is each 3h.
4. the method according to claim 2 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：The concentration refers to that Rotary Evaporators is used to be rotated under conditions of 40-60 DEG C of temperature, pressure is 0.04-0.06MPa It is volatilized to organic solvent.
5. the method according to claim 2 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：The size with the silica gel in silica gel mixed sample is 200-300 mesh.
6. the method according to claim 2 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：In step 2), described uses petroleum ether：Acetone gradient elution is successively by petroleum ether：Acetone=1:0、40:1、20: 1、10:1、5:1、2:1、1:1 and 0:1 is eluted.
7. the method according to claim 2 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：In step 3), described uses pure water：Acetone gradient elution is successively by pure water：Acetone=100：0、90:10、 80:20、70:30、60:40、50:50、40:60、30:70、20:80、10:90、0:100 are eluted.
8. the method according to claim 2 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：In step 4), described uses chloroform：Methanol elution is by chloroform：Methanol=1：1 is eluted.
9. the method according to claim 2 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：In step (5), described uses hexamethylene：Acetone elution is by hexamethylene：Acetone=3：1 is eluted.
10. the method according to claim 2 using aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters, special Sign is：In the elution, the flow velocity of eluant, eluent is 15mL/min.
CN201810818225.6A 2018-07-24 2018-07-24 A method of utilizing aspergillus niger separation and Extraction 5- nitroisophthalic acid dimethyl esters Pending CN108658779A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110343032A (en) * 2019-08-31 2019-10-18 贵州大学 A kind of method of separation and Extraction 5- pentadecyl resorcinol

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110343032A (en) * 2019-08-31 2019-10-18 贵州大学 A kind of method of separation and Extraction 5- pentadecyl resorcinol
CN110343032B (en) * 2019-08-31 2022-01-04 贵州大学 Method for separating and extracting 5-pentadecyl resorcinol

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Application publication date: 20181016