WO2014121427A1 - Procédé d'élimination d'impuretés à base d'azote aminé organique dans des acides binaires à chaîne longue produits par un procédé microbiologique - Google Patents

Procédé d'élimination d'impuretés à base d'azote aminé organique dans des acides binaires à chaîne longue produits par un procédé microbiologique Download PDF

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WO2014121427A1
WO2014121427A1 PCT/CN2013/001408 CN2013001408W WO2014121427A1 WO 2014121427 A1 WO2014121427 A1 WO 2014121427A1 CN 2013001408 W CN2013001408 W CN 2013001408W WO 2014121427 A1 WO2014121427 A1 WO 2014121427A1
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long
dibasic acid
organic amine
amine nitrogen
chain dibasic
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PCT/CN2013/001408
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English (en)
Chinese (zh)
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徐杰
王强
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Xu Jie
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/44—Polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
    • C12P7/6409—Fatty acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency
    • Y02P20/133—Renewable energy sources, e.g. sunlight

Definitions

  • the present invention relates to a method for removing organic amine nitrogen impurities from a long-chain dibasic acid produced by microbial fermentation oxidation of normal paraffins, that is, a technical category of separation and purification of chemical products.
  • a long-chain dibasic acid is an organic compound containing two carboxyl groups at both ends of a normal alkane group. It is used as a raw material for basic organic chemicals and has a wide range of uses. At present, its application is expanding to a wider scope.
  • long-chain dibasic acids we are used to refer to molecular features that contain 8 - 18 carbons.
  • the raw material produced therefrom is derived from a corresponding carbon number of normal paraffins obtained from liquid paraffin.
  • the corresponding process technology has a correspondingly high cost, and the by-product pair
  • the environment has an impact.
  • the normal paraffin is biooxidized by a specific yeast to obtain a long-chain dibasic acid, and the method has mild reaction conditions and good product selectivity. It is currently the main process technology choice for large-scale production.
  • the indicators are not up to the requirements, and some people have done work on the refining techniques of these first products, but the minimum organic amine nitrogen content is not less than 25 ⁇ ⁇ . Moreover, the application of these methods has high investment, high process operation cost and high energy consumption.
  • the present invention provides a method for removing organic amine nitrogen impurities from a long-chain dibasic acid produced by microbial fermentation of normal paraffins.
  • the object of the present invention is to provide a method for removing organic amine nitrogen impurities from a long-chain dibasic acid produced by a microbial method, which mainly uses acetone or methyl ethyl ketone as a solvent to remove oxidative oxidation by microorganisms.
  • An organic amine nitrogen compound in a long chain dibasic acid produced by an alkane to a level below 12 ppm to charge The method meets the requirements of the low organic amine nitrogen content which can be applied, and the method has low energy consumption and simple process, and has good compatibility with microbial fermentation oxidation of normal paraffin to produce long-chain dibasic acid process, and the method involves
  • the main heat source can be provided by a solar collector.
  • a method for removing organic amine nitrogen impurities from a long-chain dibasic acid produced by a microbial method according to the present invention which is obtained by microbial fermentation of a long-chain dibasic acid produced by oxidizing n-decane.
  • Organic amine nitrogen impurities, the specific operation is as follows:
  • [0007] a. A long-chain dibasic acid obtained by fermenting a normalized terpene hydrocarbon by a mutagenized strain of Candida tropicalis, dissolved in acetone or methyl ethyl ketone liquid after distillation, and dissolved at normal temperature and pressure.
  • the initial product of the dibasic acid [0008] b, the solution formed by dissolving the initial product in step a, filtering with a filter medium having a filtration precision of 0.1-50 ⁇ ⁇ , retaining the filtrate, and the filter residue is a remover;
  • 0009] c the filtered filtrate, in a heating evaporator, concentrated by distillation, the distilled acetone or methyl ethyl ketone vapor condensation and recycling;
  • the concentrated mother liquor will be precipitated with dibasic acid crystals, filtered to receive solid phase material, and after being cleaned by clean air, a long-chain dibasic acid product is obtained.
  • step d The filtered mother liquor in step d is returned to the heating evaporator for recycling.
  • the heat source and heat energy required to heat the evaporator in step d are supplied from the solar collector.
  • the invention relates to a method for removing organic amine nitrogen impurities in a long-chain dibasic acid produced by microbial fermentation oxidation of normal paraffins, which introduces acetone or methyl ethyl ketone liquid which is condensed after distillation into two
  • the first acid of the dibasic acid is placed in the container, and the introduced acetone or methyl ethyl ketone liquid is here to be combined with the preliminary product to be purified, and the preliminary product is dissolved.
  • the distillation is carried out under normal pressure, that is, acetone or methyl ethyl ketone is effectively evaporated, and the vaporized acetone or methyl ethyl ketone vapor is collected and condensed after the condensed liquid is collected and reused.
  • the mother liquor which is evaporated out of acetone or methyl ethyl ketone, a certain amount of dibasic acid crystals precipitates after reaching a supersaturated concentration due to an increase in the concentration of the dibasic acid contained therein.
  • the mother liquor containing a certain amount (5-20% w/w) of precipitated crystals is taken out, and the extracted mother liquor is effectively filtered, and the solid matter filtered out is purified by a clean air to obtain a refined long-chain dibasic acid. product.
  • the filtered mother liquor is returned to the heating evaporator and concentrated to evaporate acetone or butyl.
  • the ketone is recycled.
  • the heat source energy of the solar collector collected in the heating evaporator can be used for evaporation, the atmospheric boiling point of the evaporated acetone or methyl ethyl ketone and the heat source collected by the solar collector. The energy is well matched and the process can be carried out continuously.
  • the strain used in the present invention is a mutagenized strain of Candida tropicalis, which is entrusted to the Chinese Industrial Microbial Culture Collection and Management Center to purchase the Candida tropicalis strain No. 20962. The mutagenized strain after the change.
  • Candida tropicalis The Latin name of Candida tropicalis is: Candida tropicalis, the physiological properties of Candida tropicalis are as follows:
  • assimilation carbon source glucose +, galactose +, L-sorbose -, sucrose +, maltose +, cellobiose +, trehalose +, lactose -, melibiose -, raffinose -, pine Trisaccharide+, inulin-, soluble starch+, D-xylose+, L-arabinose+, D-arabinose-, D-ribose-, L-rhamnose-, ethanol+, glycerol+, red peony Alcohol-, ribitol+, sweet alcohol-, D-mannitol+, D-sorbitol+, inositol-, succinic acid+.
  • Morphological characteristics cream white, wrinkled, plum-like; when liquid culture, most of them are single ovoid cells.
  • the steps of the long-chain dibasic acid initial product are:
  • Wort medium 12 Brix wort, 2% agar
  • Seed medium each component is potassium dihydrogen phosphate 5.0-6.0g, sodium chloride 1.0-1.5g, magnesium sulfate heptahydrate 0.5-l. Og, sucrose 15.0-25.0g, corn syrup 1.0-2.0g , yeast extract 1.0-2.0g, urea 2.5-3.0g, vitamin B10.1-0.3g, normal paraffin C8-C1840-50ml, pure water 1000ml;
  • each component is sodium dihydrogen phosphate 2.0-3.0 g, dipotassium hydrogen phosphate 5.0-6.0 g, Ammonium sulfate 2.0-3.
  • Og sodium chloride 1.0-1.5g, yeast extract 0.5-1.0g, magnesium sulfate heptahydrate 0.5-1.
  • Og agar 15.0-20.0g, n-hydroxyl nC8- nC1820- 50ml, Pure water 1000ml, pH7.0;
  • each component is sodium dihydrogen phosphate 2.0-3.0 g, dipotassium hydrogen phosphate 5.0-6.0 g, sodium chloride 1.0-1.5 g, yeast extract 0.5-1.0 g, ammonium sulfate 2.0- 3. Og, magnesium sulfate heptahydrate 0.5-1.0g, agar 15.0-20.0g, sucrose 15, 0-20.0g, pure water 1000ml, pH7.0;
  • each component is sucrose 15.0-20.0g, sodium dihydrogen phosphate 2.0-3.0g, dipotassium hydrogen phosphate 5.0-6.0g, sodium chloride 1.0-1.5g, magnesium sulfate heptahydrate 0.5- 1.0g, yeast extract 0.5-1.0g, urea 1.5-2.0g, agar 15.0-20.0g, n-alkane nC8-nCl 820-50ml, pure water 1000ml, pH 7.5, phenol red indicator 1%;
  • Fermentation medium each component is potassium dihydrogen phosphate 5.0-6.0g, sodium chloride 1.0-1.5g, magnesium sulfate heptahydrate 0.5-1.0g, sucrose 15.0-25.0g, corn syrup 1.0-2.0g, Yeast extract 1.0-2.0g, anhydrous sodium acetate 3.0-4.0g, urea 2.0-3.0g, vitamin B10.1-0.3g, ammonium sulfate 2.0-3.0g, acrylic acid 0.001-0.002g, n-alkane nC8- nC18300 - 400ml, 1000ml of pure water;
  • the Candida tropicalis strain is inserted into the slope of the wort medium, cultured in an incubator at a temperature of 28-34'C for 24-48 hours, and 15 ml of sterile water is added to the inclined surface, and the sterile inoculating loop is used.
  • the cells were scraped into a sterile glass beaded 250 ml flask, shaken for 30 minutes to fully disintegrate the cells, and 10 ml of the bacterial suspension was taken in a 50 ml sterile flask and irradiated with cobalt 60 ⁇ -ray.
  • the irradiation dose is 0.5-0.7KGy
  • the irradiated bacterial suspension is serially diluted
  • the wort plate is coated, and cultured in the incubator at a temperature of 28-34 ° C for 36-72 hours with the control plate to select the transradian.
  • the selected single colonies are inoculated on a plate containing the screening medium III, and cultured in an incubator at a temperature of 28-34 ° C for 36-72 hours to select a tropical R. cerevisiae with a large R value. a strain, wherein R is the area of acid production by colony/colon area; [0034] Verification of Candida tropicalis mutagenized strains
  • the obtained mutagenized strain of Candida tropicalis is inoculated into a seed culture medium by a conventional method for seed culture, and then the cultured seed is inoculated into a fermentation medium for acid-producing culture, and finally in a reactor of 20 m 3
  • the medium is normalized with undecane alkane as a substrate, and cultured at a temperature of 29 ° C, aeration of 0.6-1.6 VVM (m3 air / m3 fermentation broth ⁇ ! ⁇ ) for 144 hours, fermentation test, post-fermentation and post-treatment Get the first product of undecane dibasic acid.
  • Wort medium 12 Brix wort, 2% agar
  • each component is potassium dihydrogen phosphate 5.0-6.
  • Og sodium chloride 1.0-1.5g, magnesium sulfate heptahydrate 0.5-1.
  • Og sucrose 15.0-25.
  • Og corn syrup 1.0- 2.
  • Og yeast extract 1.0-2.0g, urea 2.5-3.0g, vitamin B10.1-0.3g, normal terpene hydrocarbon C8-C1840- 50ml, pure water 1000ml;
  • each component is sodium dihydrogen phosphate 2.0-3.0 g, dipotassium hydrogen phosphate 5.0-6.0 g, ammonium sulfate 2.0-3.0 g, sodium chloride 1.0-1.5 g, yeast extract 0.5- 1.0 g, magnesium sulfate heptahydrate 0.5-1.0 g, agar 15.0-20.0 g, n-alkane nC8-nC1820-50 ml, pure water 1000 ml, pH 7.0;
  • each component is sodium dihydrogen phosphate 2.0-3.0 g, dipotassium hydrogen phosphate 5.0-6.0 g, sodium chloride 1.0-1.5 g, yeast extract 0.5-1.0 g, ammonium sulfate 2.0- 3.0g, magnesium sulfate heptahydrate 0.5-1.0g, agar 15.0-20.0g, sucrose 15.0-20.0g, pure water 1000ml, pH7.0;
  • each component is sucrose 15.0-20.0g, sodium dihydrogen phosphate 2.0-3.0g, dipotassium hydrogen phosphate 5.0-6.0g, sodium chloride 1.0-1.5g, magnesium sulfate heptahydrate 0.5- 1.0g, yeast extract 0.5-1.0g, urea 1.5-2.0g, agar 15.0-20.0g, n-alkane nC8-nC1820-50ml, pure water 1000ml, pH 7.5, phenol red indicator 1%;
  • Fermentation medium each component is 5.0-6.0 g potassium dihydrogen phosphate, 1.0-1.5 g sodium chloride, 0.5-1.0 g magnesium sulfate heptahydrate, 15.0-25.0 g sucrose, 1.0-2.0 g corn syrup, Yeast extract 1.0-2.0g, anhydrous sodium acetate 3.0-4.0g, urea 2.0-3.0g, vitamin B10.1-0.3g, ammonium sulfate 2.0-3.0g, acrylic acid 0.001-0.002g, n-alkane nC8- nC18300 ⁇ 400ml, pure water 1000ml; [0045] Mutagenesis of Candida tropicalis:
  • the Candida tropicalis strain is inserted into the slope of the wort medium, cultured in a temperature incubator for 24-48 hours, 15 ml of sterile water is added to the inclined surface, and the bacteria are scraped into the sterile inoculation loop.
  • 15 ml of sterile water is added to the inclined surface, and the bacteria are scraped into the sterile inoculation loop.
  • the cells were shaken for 30 minutes, and 10 ml of the bacterial suspension was pipetted into a 50 ml sterile flask and irradiated with cobalt 60 ⁇ -ray. The irradiation dose was 0. 5-0.
  • the irradiated bacterial suspension was serially diluted, and coated with a wort plate, and incubated with the control plate for 36-72 hours in an incubator at a temperature of 28-34 'C, and selected after irradiation.
  • a single colony with a survival rate of 10-40»/» in the selected plate is inoculated in a one-to-one correspondence to the plate containing the screening medium I and the plate containing the screening medium II at a temperature of 28-34. Incubate in an incubator for 36-72 hours, select a single colony of Candida tropicalis that does not grow on the screening medium I plate and grow vigorously on the screening medium II plate;
  • the selected single colonies are inoculated on a plate containing the screening medium III, and cultured in an incubator at a temperature of 28-34 ° C for 36-72 hours to select a tropical R. cerevisiae with a large R value.
  • a strain wherein R is the area of acid production by colony/colon area;
  • the obtained mutagenized strain of Candida tropicalis is inoculated into a seed culture medium for seed culture according to a conventional method, and the cultured seed is inoculated into a fermentation medium for acid-producing culture, and finally in a reactor of 20 m 3
  • the medium is normalized with undecane alkane as a substrate, and the fermentation is carried out for 144 hours at a temperature of 29 ° C and aeration of 0. 6-1. 6VVM (m3 air/m3 fermentation broth. min). Processing the first product of undecane dibasic acid;
  • a using a mutagenized strain of Candida tropicalis to ferment oxidized n-alkane to obtain a long-chain dibasic acid initial product, using acetone or methyl ethyl ketone liquid condensed after distillation, dissolved at normal temperature and pressure The initial product of the dibasic acid;
  • b the solution formed by dissolving the initial product in step a, filtering with a filter medium having a filtration precision of 0.1 ⁇ m, retaining the filtrate, and the filter residue is a remover;
  • the concentrated mother liquor will be precipitated with dibasic acid crystals, filtered to receive the solid phase After the substance is purged with clean air, the long-chain dibasic acid product is obtained, and the filtered mother liquor is returned to the heating evaporator for recycling.
  • the mutant strain of Candida tropicalis is fermented by oxidizing normal paraffin to obtain a long-chain dibasic acid preliminary product, which is carried out according to Example 1;
  • a a long-chain dibasic acid obtained by fermenting a normalized terpene hydrocarbon by a mutagenized strain of Candida tropicalis, using acetone or methyl ethyl ketone liquid which has been condensed after distillation, at normal temperature and pressure Dissolving the initial product of the dibasic acid;
  • b dissolving the solution formed after the initial product in step a, filtering with a filter medium of filtration precision ⁇ ⁇ ⁇ ⁇ , retaining the filtrate, and removing the residue as a remover;
  • the concentrated mother liquor will be precipitated with dibasic acid crystals, filtered to receive solid phase material, and after being purged with clean air, a long-chain dibasic acid product is obtained, filtered.
  • the mother liquor is returned to the heating evaporator for recycling.
  • a long-chain dibasic acid obtained by fermenting a normal paraffin by a mutagenized strain of Candida tropicalis is carried out according to Example 1;
  • a long-chain dibasic acid obtained by fermenting a normal paraffin by a mutagenized strain of Candida tropicalis, dissolved in acetone or methyl ethyl ketone liquid after distillation, and dissolved at normal temperature and pressure
  • the initial product of the dibasic acid [0064] b, the solution formed by dissolving the initial product in step a, filtering with a filter medium having a filtration precision of 30 ⁇ , retaining the filtrate, and the filter residue is a remover;
  • the concentrated mother liquor will be precipitated with dibasic acid crystals, filtered to receive solid phase material, and after purging with clean air, the long-chain dibasic acid product is obtained, filtered The mother liquor is returned to the heating evaporator for recycling.
  • a mutant strain of Candida tropicalis fermented a long-chain dibasic acid obtained by oxidizing normal paraffins Example 1 is carried out;
  • a a long-chain dibasic acid obtained by fermenting a normal paraffin by a mutagenized strain of Candida tropicalis, dissolved in acetone or methyl ethyl ketone liquid after distillation, and dissolved at normal temperature and pressure a preliminary product of a dibasic acid;
  • b a solution formed by dissolving the initial product in step a, filtering with a filter medium having a filtration precision of 50 ⁇ m, retaining the filtrate, and the filter residue is a remover;
  • the concentrated mother liquor will be precipitated with dibasic acid crystals, filtered to receive solid phase material, and after purging with clean air, the long-chain dibasic acid product is obtained, filtered The mother liquor is returned to the heating evaporator for recycling.

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Abstract

La présente invention concerne un procédé permettant d'éliminer des impuretés à base d'azote aminé organique dans des acides binaires à chaîne longue produits par un procédé microbiologique. Le procédé utilise principalement de l'acétone ou du butanone comme solvant pour éliminer des composés d'azote aminé organique dans des acides binaires à chaîne longue produits par l'intermédiaire de l'oxydation de n-alcanes via la fermentation microbienne, ce qui permet d'abaisseurs leurs concentrations en dessous des 12 ppm exigés, de répondre totalement à l'exigence cible proposée d'une faible teneur d'azote aminé organique par application ; dans le même temps, cette technique consomme peu d'énergie, est un procédé simple et est bien liée au procédé de production d'acides binaires à chaîne longue par le biais de l'oxydation de n-alcanes via la fermentation microbienne, et la principale source de chaleur impliquée dans la technique peut être fournie par l'intermédiaire d'un capteur solaire thermique.
PCT/CN2013/001408 2013-02-05 2013-11-18 Procédé d'élimination d'impuretés à base d'azote aminé organique dans des acides binaires à chaîne longue produits par un procédé microbiologique WO2014121427A1 (fr)

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CN104844442A (zh) * 2014-02-18 2015-08-19 上海凯赛生物技术研发中心有限公司 一种从溶剂母液中制备混合酸的方法
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