CN110054561A - A kind of oxidative decoloration technique of long-chain biatomic acid - Google Patents
A kind of oxidative decoloration technique of long-chain biatomic acid Download PDFInfo
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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Abstract
The present invention provides a kind of oxidative decoloration technique of long-chain biatomic acid, the technique mainly includes following technique: long-chain biatomic acid crude product being dissolved in solvent, potassium permanganate oxidation decoloration is added, one of active carbon, atlapulgite, diatomite or a variety of are added after decoloration, filtering, obtains clear liquid.Its own only generates the manganese dioxide solid of slightly solubility after potassium permanganate is added, there is no the generation of liquid phase by-product, organic solvent composition will not be changed, cooperated with active carbon etc., decolorizing effect chemically can be played with physics double angle, a small amount of be added can play unexpected effect.
Description
Technical field
The present invention relates to the refining methds of long-chain biatomic acid made from biological fermentation process, and in particular to a kind of long-chain biatomic acid
Oxidative decoloration technique.
Background technique
Long-chain biatomic acid (Long chain dicarboxylic acids), which refers to, contains 10 or more carbon atoms in carbochain
Aliphatic dicarboxylic acid (abbreviation DCn), including saturation and unsaturated dicarboxylic are that a kind of have important and extensive industrial use
Fine chemical product is that fine perfumery, high performance nylon engineering plastics, high-grade nylon hot-melt adhesive, high temperature are synthesized in chemical industry
The important foundation of dielectric, advanced paint and coating, senior lubricant, cold-resistant plasticizer, resin, medicine and pesticide etc. is former
Material.Since the potentiality to be exploited of the downstream product of long-chain biatomic acid is wide, the demand of long-chain biatomic acid will constantly be increased both at home and abroad
Add, market potential is very big.
Bioanalysis (fermentation method) production long-chain biatomic acid is the microbial technique of 1970s rise in petrochemical industry
The application in field.Its main feature is that utilizing the distinctive oxidability of microorganism and extracellular microbial using petroleum resources abundant as raw material
The effect of interior enzyme aoxidizes two methyl at long-chain normal alkane both ends respectively at normal temperatures and pressures, and a step adds four oxygen atoms, raw
At the various long-chain biatomic acids of respective chain length；Bioanalysis production long-chain biatomic acid overcomes simple chemical synthesis process and plant
The various deficiencies of object oil-breaking preparation method open new approach for the mass production of long-chain biatomic acid.With chemical synthesis side
Method is compared, and bioanalysis production long carbochain biatomic acid possesses indubitable advantage, at home and abroad by most attention.Bioanalysis is not
The serial long carbochain biatomic acid monomer of even C22 can be only provided from C9 to C18, and chemical synthesis institute can be produced not
Fertile long-chain biatomic acid (long-chain biatomic acid of such as C13 or more), is greatly expanded binary acid in the application of industrial circle.
Bioanalysis prepares long-chain biatomic acid mild condition, simple process.But fermentation liquid be containing binary acid, residual alkane,
Emulsion, thallus, culture medium and various metabolites mixture.Remaining some pigments, nitrogen compound in extraction purification,
Influence polymerization.Long-chain biatomic acid extracts mainly with solvent processing and water process in industrial production.Its decolorization is mainly in water
It neutralizes and is carried out in solvent.
Product is reduced using long-chain biatomic acid mono-salt crystallization processes in patent CN1255483A (publication date 2000-06-07)
The impurity contents such as middle protein and pigment prepare long-chain biatomic acid product of the total acid content greater than 99%, white in appearance.This method
It needs to be acidified repeatedly, the engineering issues such as tiny, sad filter that mono-salt crystallographic property is poor, and there are particles, difficult washing are fine to operating
Degree requires high；And mono-salt solubility is larger, binary acid yield is lower.
In patent CN1351006A (publication date 2002-05-29) using the technique that primary acidification and primary melting are decolourized come
Reduce the impurity contents such as protein, organic pigment in product.Used adsorbent is active carbon, atlapulgite etc..This method
It needs to melt binary acid crude, mailland reaction easily occurs under high temperature, reproducibility group is made to react, influence product, and
Product yield is lower, and melting energy consumption is high, is unsuitable for industrialized production.
Then patent CN102010318A (publication date 2011-04-13) is acidified in water phase using decolourizing twice or repeatedly
Method, can remove some pigments, improve mixed dibasic acid purity.The disadvantage is that: the twice or multiple active carbon of the process requirement
Decoloration, causes a large amount of loss yields of binary acid relatively low, cost is excessively high.
Oxidation technology is long-chain biatomic acid decoloration process commonly used in the prior art, patent CN103497100A (publication date
Long-chain biatomic acid water phase dual-stage method of purification is proposed in 2014-01-08), at pH5-9, oxidizer after heating, shielding two
First acid carboxyl is reacted with reducing impurity, and for heating and temperature control at 80~100 DEG C, oxidant is sodium hypochlorite or ozone, oxidation
Acidification obtains long-chain biatomic acid afterwards.It is raw that patent CN104844441A (publication date 2015-08-19) provides a kind of pair of long-chain biatomic acid
The method that waste-long-chain mixed dibasic acid (also referred to as mixed dibasic acid) in production extracts.This method, which first passes through, to be added
Alkali adjusts pH, and cooling is precipitated and obtains intermediate after dissolution, then after being dissolved, and oxidant is added and is aoxidized, oxidant used
For ozone and/or hydrogen peroxide.It is finally acidified to obtain long-chain biatomic acid.The invention passes through secondary precipitation in water phase and oxidation work
Skill is used in combination, and obtains the mixed dibasic acid finished product of high quality, and white color is high-quality, high carbon number binary acid (C16 or more two
First acid) content is low.
Also there is the method decolourized in organic phase, patent CN101985416A (publication date 2011-03-16) is molten by binary acid
In the above acetic acid solvent of 90% concentration, active carbon decoloring is added in acetic acid, destainer is crystallized, polymer grade long-chain binary is obtained
Acid.The technique only uses active carbon, mainly utilizes activated carbon adsorption property, is difficult to remove to some small molecule substances containing double bond.
In terms of existing method, adoptable discoloration method can be divided mainly into be taken off for oxidizing decoloration and activated carbon adsorption
Color, two methods can be used in water phase, and oxidant used is ozone, sodium hypochlorite or hydrogen peroxide.Ozone oxidation effect is good,
But it needs special equipment to generate, has pollution to environment；Sodium hypochlorite and hydrogen peroxide are aqueous solution state, and the efficient oxidation ability is poor,
And transport and storage are dangerous；Use activated carbon adsorption in organic phase, only physical removal ability, according to sodium hypochlorite or
The water that hydrogen peroxide introduces can change solvent composition.
Summary of the invention
The present invention provides a kind of oxidation of long-chain biatomic acid for the deficiency of long-chain biatomic acid decoloration process in prior art
The key step of decoloration process, the technique is as follows:
Long-chain biatomic acid crude product is dissolved in solvent, potassium permanganate is added, adds active carbon, atlapulgite, diatom
One of soil is a variety of, and filtering obtains clear liquid.
Heretofore described long-chain biatomic acid is azelaic acid, decanedioic acid, eleven carbon diacids, dodecanedicarboxylic acid, 13
Carbon dicarboxylic acid, tetradecane diacid, pentadecane binary acid, 16-dicarboxylic acid, seventeen carbon diacids, octadecane diacid or 9-
One of eight carbon diacid of alkene-ten or a variety of mixtures.
Heretofore described long-chain biatomic acid crude product can be directly acidified by long-chain biatomic acid fermentation liquid prepared by bioanalysis
It precipitates and is isolated；The long-chain biatomic acid fermentation liquid of bioanalysis preparation passes through certain processing, such as active carbon decoloring, film mistake
It filters out and obtains filtrate after the methods of bacterium, then acid precipitation and be isolated；Alternatively, the long-chain biatomic acid fermentation of bioanalysis preparation
The direct acid precipitation of liquid and separate after, using washing or high temperature water process after obtain.
Heretofore described long-chain biatomic acid crude product can also originate from fermentation, be discharged in subtractive process rich in long-chain two
The waste liquid of first acid, for example, obtained in long-chain biatomic acid product extraction process, include but is not limited to that long-chain biatomic acid recrystallization is female
The long-chain biatomic acid mixture obtained after liquid is dry, in another example long-chain biatomic acid sewage treatment plant precipitates what accumulation obtained for a long time
Long-chain biatomic acid precipitating.
Heretofore described long-chain biatomic acid fermentation liquid be obtain after Production of Long Chain Dicarboxylic Acids Through Micro-Biological Fermen it is more
Phase mixture is also possible to long-chain biatomic acid comprising moisture, fermentation substrate remnants, long-chain biatomic acid salt, thallus and other impurity
After fermentation, to fermentation liquid by handling, remove in fermentation liquid in addition to long-chain biatomic acid salt it is one or more kinds of its
Its component reduces the multiphase mixture (i.e. the treatment fluid of fermentation liquid) obtained after its content.
Heretofore described solvent includes one or more in C11-C13 alkane, methanol, ethyl alcohol, acetic acid or ethyl acetate
Mixture.According to solubility of the binary acid in different solvents, mass ratio is according to long-chain biatomic acid crude product: solvent=1:1.5-
1:10, preferably crude product: solvent=1:2-1:5.
The oxidative decoloration temperature of heretofore described long-chain biatomic acid oxidative decoloration technique is 30-95 DEG C, preferably 50-90
DEG C, the oxidative decoloration time is 0.5-6h, preferably 0.5-3h, further preferably 0.5-2h.
The additional amount of heretofore described potassium permanganate is the 0.02%-5% of long-chain biatomic acid crude product quality, preferably
0.05%-3%, further preferably 0.1%-2%.
In the present invention on the one hand the addition of active carbon, atlapulgite, diatomite is played in drainage long-chain biatomic acid crude product not
Molten object effect, the more adsorbable impurity molecule that can not be aoxidized of another aspect.Adsorbent or filter aid additional amount need to be according to products
Quality requirement adjustment is the 0.2%-20%, preferably 0.5%-10% of binary acid crude product quality.
By gained clear liquid decrease temperature crystalline, washs, is dried to obtain long-chain biatomic acid finished product.
The beneficial effects of the present invention are: it is easy to operate, simply add a small amount of potassium permanganate；Long-chain biatomic acid and impurity
It is in organic solvent in dissolved state, oxidation effectiveness is good；It is solid that the manganese dioxide that its own only generates slightly solubility is added in potassium permanganate
Body is generated without liquid phase by-product, will not change organic solvent composition, such as water content.And in contrast, ozone is added, there is life
At the possibility of peroxide, there are certain safety risks.Sodium hypochlorite, hydrogen peroxide are all industrially aqueous solution states, inherently
A large amount of water are introduced, dicyandiamide solution is caused to change.Potassium permanganate is added, cooperates with active carbon etc., it can chemically and object
Reason double angle plays decolorizing effect, and a small amount of be added can play unexpected effect.
Specific embodiment
Analyzing detecting method:
1, binary acid gas chromatographic detection:
Using standard dyadic acid sample as compareing, with reference to fatty acid in GB5413.27-2010 infant food and dairy products
Measurement.
2, determination of total nitrogen content:
Using Kjeldahl's method.
3, determination of light transmittance:
Binary acid sample is dissolved into the sodium-salt aqueous solution of weight concentration 5%, then UV detects the light transmittance under 430nm.
Comparative example 1
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid, first using obtaining filtrate after film filtration sterilization method, and by its acid precipitation and filter, dry after obtain 12
Carbon dicarboxylic acid is acidified crude product.According to crude product: binary acid crude is added to the acetum of 96% concentration by solvent=1:3 ratio
In, stirring, 90 DEG C of dissolutions are added 1% active carbon decoloring 1h of crude product quality, are filtered until clear.Slow cooling crystallizes to 30 DEG C,
Filtering, 1 times of amount acetic acid washing of crude product quality, 5 times of amount washings, 105 DEG C of dry 4h obtain finished product.
Comparative example 2
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid adds 3% active carbon decoloring first using filtrate is obtained after film filtration sterilization method, and by its acid precipitation
And filter, dry after obtain dodecanedicarboxylic acid acidification crude product.And solvent refining is used according to embodiment 30.By subtractive process crystalline substance
Mother liquor after body separation is evaporated, and obtains the heavy constituent rich in long-chain biatomic acid.According to heavy constituent: solvent=1:4 ratio is by binary
Acid crude is added in the ethanol solution of 97% concentration, stirring, 88 DEG C of dissolutions, and the active carbon decoloring 1h of heavy constituent quality 5% is added,
It is filtered until clear.Slow cooling crystallizes to 30 DEG C, and filtering, 1 times of amount acetic acid of crude product quality washs, 5 times of amounts washings, 95 DEG C of dryings
4h obtains finished product.
Comparative example 3
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid, first using obtaining filtrate after film filtration sterilization method, and by its acid precipitation and filter, dry after obtain 12
Carbon dicarboxylic acid is acidified crude product.According to crude product: binary acid crude is added to the acetum of 96% concentration by solvent=1:5 ratio
In, the sodium hypochlorite (effective chlorine 13%) of crude product quality 5% is added in stirring, 60 DEG C of dissolutions, and add crude product quality 1% is living
Property carbon decoloring 2h, is filtered until clear.Slow cooling crystallizes to 30 DEG C, and filtering, 1 times of amount acetic acid of crude product quality washs, 5 times of amount water
It washes, 105 DEG C of dry 4h obtain finished product.
Comparative example 4
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid adds 3% active carbon decoloring first using filtrate is obtained after film filtration sterilization method, and by its acid precipitation
And filter, dry after obtain dodecanedicarboxylic acid acidification crude product.And solvent refining is used according to embodiment 30.By subtractive process crystalline substance
Mother liquor after body separation is evaporated, and obtains the heavy constituent rich in long-chain biatomic acid.According to heavy constituent: solvent=1:3 ratio is by binary
Acid crude is added in the ethyl acetate solution of 97% concentration, stirring, and the hydrogen peroxide of heavy constituent quality 5% is added in 88 DEG C of dissolutions,
The 5% active carbon decoloring 1h for adding heavy constituent quality, is filtered until clear.Slow cooling crystallizes to 30 DEG C, filters, crude product quality
1 times of amount acetic acid washing, 5 times of amount washings, 95 DEG C of dry 4h obtain finished product.
Embodiment 1
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid, first using obtaining filtrate after film filtration sterilization method, and by its acid precipitation and filter, dry after obtain 12
Carbon dicarboxylic acid is acidified crude product.According to crude product: binary acid crude is added to the acetum of 96% concentration by solvent=1:3 ratio
In, 0.15% potassium permanganate of crude product quality is added in stirring, 90 DEG C of dissolutions, adds 1% active carbon decoloring of crude product quality
1h is filtered until clear.Slow cooling crystallizes to 30 DEG C, and filtering, 1 times of amount acetic acid washing of crude product quality, 5 times of amount washings, 105 DEG C dry
Dry 4h, obtains finished product.
Embodiment 2
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid adds 3% active carbon decoloring first using filtrate is obtained after film filtration sterilization method, and by its acid precipitation
And filter, dry after obtain dodecanedicarboxylic acid acidification crude product.And solvent refining is used according to embodiment 30.By subtractive process crystalline substance
Mother liquor after body separation is evaporated, and obtains the heavy constituent rich in long-chain biatomic acid.According to heavy constituent: solvent=1:4 ratio is by binary
Acid crude is added in the ethanol solution of 97% concentration, stirring, and 0.8% permanganic acid of heavy constituent quality is added in 88 DEG C of dissolutions
Potassium is added 1% active carbon decoloring 1h of crude product quality, is filtered until clear.Slow cooling crystallizes to 30 DEG C, filters, crude product quality 1
Amount acetic acid washing again, 5 times of amounts washings, 95 DEG C of dry 4h obtain finished product.
Embodiment 3
According to 5 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 13 carbon two are obtained
First acid fermentation liquid, first using obtaining filtrate after film filtration sterilization method, and by its acid precipitation and filter, dry after obtain 13
Carbon dicarboxylic acid is acidified crude product.According to crude product: binary acid crude is added to the ethanol solution of 95% concentration by solvent=1:3 ratio
In, 0.2% potassium permanganate of crude product quality is added in stirring, 60 DEG C of dissolutions, adds the 2% diatomite stirring of crude product quality
2h is filtered until clear.Slow cooling crystallizes to 30 DEG C, and filtering, 1 times of amount acetic acid washing of crude product quality, 5 times of amount washings, 105 DEG C dry
Dry 4h, obtains finished product.
Embodiment 4
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid adds 3% active carbon decoloring first using filtrate is obtained after film filtration sterilization method, and by its acid precipitation
And filter, dry after obtain dodecanedicarboxylic acid acidification crude product.And solvent refining is used according to embodiment 30.By subtractive process crystalline substance
Mother liquor after body separation is evaporated, and obtains the heavy constituent rich in long-chain biatomic acid.According to heavy constituent: solvent=1:4 ratio is by binary
Acid crude is added in the ethyl acetate solution of 97% concentration, stirring, and 0.8% height of heavy constituent quality is added in 88 DEG C of dissolutions
Potassium manganate is added 1% active carbon decoloring 1h of crude product quality, is filtered until clear.Slow cooling crystallizes to 30 DEG C, filters, crude product
1 times of amount acetic acid washing of quality, 5 times of amount washings, 95 DEG C of dry 4h obtain finished product.
Embodiment 5
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid adds 3% active carbon decoloring first using filtrate is obtained after film filtration sterilization method, and by its acid precipitation
And filter, dry after obtain dodecanedicarboxylic acid acidification crude product.And solvent refining is used according to embodiment 30.By subtractive process crystalline substance
Mother liquor after body separation is evaporated, and obtains the heavy constituent rich in long-chain biatomic acid.According to heavy constituent: solvent=1:5 ratio is by binary
Acid crude is added in the acetum of 97% concentration, stirring, and 2% potassium permanganate of heavy constituent quality is added in 88 DEG C of dissolutions
1.5h is reacted, 1% active carbon decoloring 1h of crude product quality is added, is filtered until clear.Slow cooling crystallizes to 30 DEG C, filters, slightly
1 times of amount acetic acid washing of quality, 5 times of amount washings, 95 DEG C of dry 4h obtain finished product.
Embodiment 6
According to 4 fermentation process of patent document CN1570124A (publication date 2005-01-26) embodiment, 12 carbon two are obtained
First acid fermentation liquid adds 3% active carbon decoloring first using filtrate is obtained after film filtration sterilization method, and by its acid precipitation
And filter, dry after obtain dodecanedicarboxylic acid acidification crude product.And solvent refining is used according to embodiment 30.By subtractive process crystalline substance
Mother liquor after body separation is evaporated, and obtains the heavy constituent rich in long-chain biatomic acid.According to heavy constituent: solvent=1:4 ratio is by binary
Acid crude is added in the methanol solution of 97% concentration, stirring, and 2% potassium permanganate of heavy constituent quality is added in 78 DEG C of dissolutions
1h is reacted, 1% active carbon decoloring 2h of crude product quality is added, is filtered until clear.Slow cooling crystallizes to 30 DEG C, filters, crude product
1 times of amount acetic acid washing of quality, 5 times of amount washings, 95 DEG C of dry 4h obtain finished product.
The comparison of 1 product quality of table
In table 1, embodiment 1, embodiment 3 and comparative example 1, comparative example 3 are compared, by embodiment 2 and comparative example 2 into
Row compares, and embodiment 4-6 and comparative example 4 is compared it is found that product translucency is available aobvious using potassium permanganate oxidation
It writes under raising or equal conditions, the dosages such as active carbon can be greatly decreased, save the cost.
Although the preferred embodiments of the invention, those skilled in the art has been disclosed in order to illustrate the present invention
Member can be the present invention it should be appreciated that in the case where not departing from present inventive concept defined by claims and range
Various modifications, addition and replacement out.
Claims (6)
1. a kind of oxidative decoloration technique of long-chain biatomic acid, which is characterized in that the oxidative decoloration technique will be the following steps are included: will
Long-chain biatomic acid crude product is dissolved in solvent, and potassium permanganate is added, adds one of active carbon, atlapulgite, diatomite
Or it is a variety of, filtering obtains clear liquid.
2. the oxidative decoloration technique of long-chain biatomic acid as described in claim 1, the long-chain biatomic acid is azelaic acid, the last of the ten Heavenly stems two
Acid, eleven carbon diacids, dodecanedicarboxylic acid, tridecanyldicarboxylic acid, tetradecane diacid, pentadecane binary acid, 16 carbon two
One of first acid ,-ten eight carbon diacid of seventeen carbon diacids, octadecane diacid or 9- alkene or a variety of mixtures.
3. the oxidative decoloration technique of long-chain biatomic acid as described in claim 1, the solvent include C11-C13 alkane, methanol,
One or more mixture in ethyl alcohol, acetic acid or ethyl acetate, mass ratio are long-chain biatomic acid crude product: solvent=1:1.5-1:
10, preferably crude product: solvent=1:2-1:5.
4. the oxidative decoloration technique of long-chain biatomic acid as described in claim 1, the oxidative decoloration temperature of the oxidative decoloration technique
Degree is 30-95 DEG C, and preferably 50-90 DEG C, the oxidative decoloration time is 0.5-6h, preferably 0.5-3h, further preferably 0.5-
2h。
5. the oxidative decoloration technique of long-chain biatomic acid as described in claim 1, the additional amount of the potassium permanganate is long-chain two
The 0.02%-5% of first acid crude quality, preferably 0.05%-3%, further preferably 0.1%-2%.
6. the oxidative decoloration technique of long-chain biatomic acid as described in claim 1, the active carbon, atlapulgite or diatomite
Additional amount is the 0.2%-20%, preferably 0.5%-10% of long-chain biatomic acid crude product quality.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113493378A (en) * | 2020-04-01 | 2021-10-12 | 上海凯赛生物技术股份有限公司 | Long-chain dicarboxylic acid product and refining process thereof |
| CN114426479A (en) * | 2020-10-10 | 2022-05-03 | 中国石油化工股份有限公司 | Method and device for refining long-chain dicarboxylic acid |
| CN114525311A (en) * | 2020-10-31 | 2022-05-24 | 中国石油化工股份有限公司 | Method and device for preparing long-chain dicarboxylic acid by fermentation |
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| CN113493378A (en) * | 2020-04-01 | 2021-10-12 | 上海凯赛生物技术股份有限公司 | Long-chain dicarboxylic acid product and refining process thereof |
| CN114426479A (en) * | 2020-10-10 | 2022-05-03 | 中国石油化工股份有限公司 | Method and device for refining long-chain dicarboxylic acid |
| CN114525311A (en) * | 2020-10-31 | 2022-05-24 | 中国石油化工股份有限公司 | Method and device for preparing long-chain dicarboxylic acid by fermentation |
| CN114525311B (en) * | 2020-10-31 | 2023-07-28 | 中国石油化工股份有限公司 | Method and device for preparing long-chain dibasic acid through fermentation |
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