CN114436820A - Preparation method and application of dodecanedioic acid seed crystal - Google Patents
Preparation method and application of dodecanedioic acid seed crystal Download PDFInfo
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- CN114436820A CN114436820A CN202210063486.8A CN202210063486A CN114436820A CN 114436820 A CN114436820 A CN 114436820A CN 202210063486 A CN202210063486 A CN 202210063486A CN 114436820 A CN114436820 A CN 114436820A
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- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 title claims abstract description 267
- 239000013078 crystal Substances 0.000 title claims abstract description 178
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000000498 ball milling Methods 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 36
- 238000002425 crystallisation Methods 0.000 claims abstract description 12
- 230000008025 crystallization Effects 0.000 claims abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 65
- 238000001816 cooling Methods 0.000 claims description 35
- 238000003756 stirring Methods 0.000 claims description 27
- 238000001035 drying Methods 0.000 claims description 23
- 238000000227 grinding Methods 0.000 claims description 22
- 230000001788 irregular Effects 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002002 slurry Substances 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 238000000967 suction filtration Methods 0.000 claims description 11
- 239000012065 filter cake Substances 0.000 claims description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 238000007873 sieving Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 2
- 239000012046 mixed solvent Substances 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 51
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- 239000000047 product Substances 0.000 description 38
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 21
- 238000003828 vacuum filtration Methods 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 238000005029 sieve analysis Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910001220 stainless steel Inorganic materials 0.000 description 10
- 239000010935 stainless steel Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- 239000010431 corundum Substances 0.000 description 4
- 229910052593 corundum Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
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- 239000010453 quartz Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000004831 Hot glue Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
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- 238000004886 process control Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000010900 secondary nucleation Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 241000402754 Erythranthe moschata Species 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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Images
Classifications
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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
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- 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
Abstract
The invention relates to the technical field of dodecanedioic acid crystallization, and discloses a preparation method and application of a dodecanedioic acid seed crystal. The method prepares the dodecanedioic acid seed crystal through mechanical ball milling, the process for preparing the seed crystal is simple, the energy consumption is low, the obtained seed crystal has uniform particle size distribution, the recovery rate can reach 90 percent, and the particle size of the seed crystal is 48-150 mu m; the crystal seed is used for induced crystallization to produce a product, the crystal grain size is larger, the average grain size of the crystal reaches 321.56 mu m, the crystal form is more uniform, and the product meets the requirements of the European and American markets on dustless and low pulverization of the product outlet.
Description
(I) the technical field
The invention relates to the technical field of dodecanedioic acid crystallization, in particular to a preparation method of dodecanedioic acid seed crystals and application of the dodecanedioic acid seed crystals prepared by the method in preparation of regular dodecanedioic acid crystals.
(II) background of the invention
The long-chain dicarboxylic acid is straight-chain dicarboxylic acid containing more than 10 carbon atoms, and is an important fine chemical product. Is the main raw material for synthesizing special products such as musk-T, copolyamide hot melt adhesive, nylon engineering plastics and the like. The long-chain dicarboxylic acid is used as a basic raw material to produce and synthesize fine chemical products such as high-grade spice musk, high-grade nylon rubber, high-temperature electrolyte, high-grade hot melt adhesive, cold-resistant plasticizer, high-grade lubricating oil, high-grade paint, coating and the like, and the method is widely applied to the fields of chemical industry, light industry, pesticide, medicine, liquid crystal materials and the like. Wherein the dodecanedioic acid (DC)12) Is an important raw material for synthesizing high-performance nylon engineering plastics, high-grade hot melt adhesives and high-grade paints and coatings.
At present, the production method of dodecanedioic acid mainly comprises a chemical synthesis method and a biological catalysis method, and the chemical synthesis method has the problems of complex process, harsh conditions, serious environmental pollution, low product yield, high production cost and the like, so that the biological catalysis method for specifically oxidizing saturated alkane substrates by using industrial microorganisms becomes a main method for industrially producing the dodecanedioic acid, and the method has the advantages of mild process conditions, environmental friendliness, economy, high efficiency and the like. The method has the disadvantages that in the production process of dodecanedioic acid by using biocatalysis, the secondary nucleation phenomenon generated by crystal collision exists in the important unit operation-crystallization process of product extraction and refining, and the phenomenon causes that the grain diameter of a crystal product is small and the crystal form is not uniform. Finally, the product has the problems of powdering, easy caking and the like, and the synthesis requirement of downstream high-end products at home and abroad is difficult to meet. The method carries out industrial induced crystallization by using proper seed crystals (mother crystals), can effectively control secondary nucleation (particularly contact nucleation), and realizes the aim of improving the crystal habit of products. The invention discloses a preparation method of a dodecanedioic acid seed crystal and application of the dodecanedioic acid seed crystal to an induced crystallization process. The product produced by the technology has large crystal grain diameter and more uniform crystal form.
Disclosure of the invention
The invention aims to provide a preparation method and application of a dodecanedioic acid seed crystal, which solve the problems in the prior art, obtain a product with larger crystal particle size and more uniform crystal form and meet the requirements of high-end product production in Europe and America on dustless and low pulverization of a product outlet.
The invention provides a preparation method of a dodecanedioic acid seed crystal, which comprises the following steps:
mechanically ball-milling irregular dodecanedioic acid crystals A for 20-60 min at a ball-material ratio of 2-5: 1 (preferably 2-3: 1) and a ball-milling rotation speed of 200-400 r/min (preferably 200-250 r/min) at room temperature, and sieving with a 100-300-mesh sieve to obtain dodecanedioic acid seed crystals with the particle size of 48-150 mu m; the diameter of the grinding ball used for the mechanical ball milling is 0.1-20mm (preferably 8 mm). The ball material ratio refers to the mass ratio of the grinding ball to the irregular dodecanedioic acid crystal A.
Preferably, the mechanical ball milling adopts a high-energy planetary ball mill, wherein the ball milling tank is made of stainless steel, the grinding balls are made of stainless steel, corundum or quartz, and the diameter of the grinding balls is 8 mm.
The purity of the irregular dodecanedioic acid crystal A is more than or equal to 99 percent.
The invention also provides application of the dodecanedioic acid seed crystal prepared by the method in preparation of a regular dodecanedioic acid crystal.
The invention provides two application methods:
1. the application is as follows: stirring and dissolving irregular dodecanedioic acid B in an organic solvent B at 70-90 ℃ to obtain a supersaturated dodecanedioic acid solution, preserving the temperature for 30-60 min, cooling to 38-44 ℃, adding the dodecanedioic acid seed crystal, cooling to room temperature to completely separate out the crystal, carrying out suction filtration (vacuum filtration under 0.08 MPa) on the obtained crystal slurry, and drying the obtained filter cake to obtain the regular dodecanedioic acid crystal; the mass ratio of the dodecanedioic acid seed crystal to the irregular dodecanedioic acid B is 0.25-1: 100 (preferably 0.5-1: 100, most preferably 0.5: 100).
Preferably, the organic solvent B is mainly C1-2Alcohols (methanol, ethanol), C1-2Saturated organic acids (formic acid, acetic acid), esters (ethyl acetate, butyl acetate), ethers (diethyl ether), ketones (acetone), and mixtures thereof. Acetic acid is particularly preferred.
Preferably, the stirring speed is 200-300 r/min.
Preferably, the suction filtration is carried out under the condition of vacuum filtration at 0.08MPa until no liquid flows out.
Preferably, the drying temperature is 60-100 ℃, more preferably 80-90 ℃, such as 85 ℃.
2. The application is as follows: stirring and dissolving irregular dodecanedioic acid C in an organic solvent C at 70-90 ℃ to obtain a supersaturated dodecanedioic acid solution, keeping the temperature for 30-60 min (preferably 60min), cooling to 38-44 ℃, adding the dodecanedioic acid seed crystal, standing at a constant temperature for crystallization for 0-120min (wherein 0 is infinitely close to 0 but not 0, preferably 40-120min, most preferably 120min), cooling to room temperature to completely precipitate crystals, carrying out suction filtration on the obtained crystal slurry, and drying the obtained filter cake to obtain the regular dodecanedioic acid crystals; the mass ratio of the dodecanedioic acid seed crystal to the irregular dodecanedioic acid C is 0.25-1: 100 (preferably 0.5-1: 100, most preferably 0.5: 100).
The irregular dodecanedioic acid A, B, C is only used for distinguishing the dodecanedioic acid added at different stages, and has no other meaning.
Preferably, the organic solvent C is mainly C1-2Alcohols (methanol, ethanol), C1-2Saturated organic acids (formic acid, acetic acid), esters (ethyl acetate, butyl acetate), ethers (diethyl ether), ketones (acetone), and mixtures thereof. Acetic acid is particularly preferred. The organic solvent B, C is used only to distinguish the organic solvent from the different methods and has no other meaning.
Preferably, the stirring speed is 200-300 r/min.
Preferably, the suction filtration is carried out under the condition of vacuum filtration at 0.08MPa until no liquid flows out.
The room temperature is 25-30 ℃.
Preferably, the drying temperature is 60-100 ℃, more preferably 80-90 ℃, such as 85 ℃.
The invention specifically provides a preparation method of a regular dodecanedioic acid crystal, which comprises the following steps:
(1) mechanically ball-milling irregular dodecanedioic acid crystals A for 20-60 min at a ball-material ratio of 2-5: 1 (preferably 2-3: 1) and a ball-milling rotation speed of 200-400 r/min (preferably 200-250 r/min) at room temperature, and sieving with a 100-300-mesh sieve to obtain dodecanedioic acid seed crystals with the particle size of 48-150 mu m; the diameter of the grinding ball used for the mechanical ball milling is 0.1-20mm (preferably 8 mm);
(2) stirring and dissolving irregular dodecanedioic acid B in an organic solvent B at 70-90 ℃ to obtain a supersaturated dodecanedioic acid solution, preserving heat for 30-60 min, cooling to 38-44 ℃, adding the dodecanedioic acid seed crystal in the step (1), cooling to room temperature to completely separate out crystals, carrying out suction filtration on the obtained crystal slurry (vacuum suction filtration under 0.08 MPa), and drying the obtained filter cake to obtain the regular dodecanedioic acid crystals; the mass ratio of the dodecanedioic acid seed crystal to the irregular dodecanedioic acid B is 0.25-1: 100 (preferably 0.5-1: 100, most preferably 0.5: 100).
Preferably, the mechanical ball milling in step (1) adopts a high-energy planetary ball mill, wherein the ball milling tank is made of stainless steel, the grinding balls are made of stainless steel, corundum or quartz, and the diameter of the grinding balls is 8 mm.
The purity of the irregular dodecanedioic acid crystal A in the step (1) is more than or equal to 99%.
Preferably, the organic solvent B in the step (2) is mainly C1-2Alcohols (methanol, ethanol), C1-2Saturated organic acids (formic acid, acetic acid), esters (ethyl acetate, butyl acetate), ethers (diethyl ether), ketones (acetone), and mixtures thereof. Acetic acid is particularly preferred.
Preferably, the stirring speed of the step (2) is 200-300 r/min.
Preferably, the suction filtration in the step (2) is carried out under the condition of vacuum filtration at 0.08MPa until no liquid flows out.
Preferably, the drying temperature in the step (2) is 60-100 ℃, more preferably 80-90 ℃, such as 85 ℃.
The invention also specifically provides a preparation method of the regular dodecanedioic acid crystal, which comprises the following steps:
1) mechanically ball-milling irregular dodecanedioic acid crystals A for 20-60 min at a ball-material ratio of 2-5: 1 (preferably 2-3: 1) and a ball-milling rotation speed of 200-400 r/min (preferably 200-250 r/min) at room temperature, and sieving with a 100-300-mesh sieve to obtain dodecanedioic acid seed crystals with the particle size of 48-150 mu m; the diameter of the grinding ball used for the mechanical ball milling is 0.1-20mm (preferably 8 mm);
2) stirring and dissolving irregular dodecanedioic acid C in an organic solvent C at 70-90 ℃ to obtain a supersaturated dodecanedioic acid solution, keeping the temperature for 30-60 min (preferably 60min), cooling to 38-44 ℃, putting the dodecanedioic acid seed crystal in the step 1), standing at a constant temperature for growing crystals for 0-120min (wherein 0 is infinitely close to 0 but not 0, preferably 40-120min, and most preferably 120min), cooling to room temperature to completely precipitate crystals, carrying out suction filtration on the obtained crystal slurry, and drying the obtained filter cake to obtain the regular dodecanedioic acid crystals; the mass ratio of the dodecanedioic acid seed crystal to the irregular dodecanedioic acid C is 0.25-1: 100 (preferably 0.5-1: 100, most preferably 0.5: 100).
Preferably, the mechanical ball milling in step 1) adopts a high-energy planetary ball mill, wherein the ball milling tank is made of stainless steel, the grinding balls are made of stainless steel, corundum or quartz, and the diameter of the grinding balls is 8 mm.
The purity of the irregular dodecanedioic acid crystal A in the step 1) is more than or equal to 99%.
Preferably, the organic solvent C in step 2) is mainly C1-2Alcohols (methanol, ethanol), C1-2Saturated organic acids (formic acid, acetic acid), esters (ethyl acetate, butyl acetate), ethers (diethyl ether), ketones (acetone), and mixtures thereof. Acetic acid is particularly preferred.
Preferably, the stirring speed in the step 2) is 200-300 r/min.
Preferably, the suction filtration in the step 2) is carried out under the condition of vacuum filtration at 0.08MPa until no liquid flows out.
Preferably, the drying temperature in the step 2) is 60-100 ℃, more preferably 80-90 ℃, such as 85 ℃.
Compared with the prior art, the invention has the following beneficial effects:
1. the method has good refining effect on the dodecanedioic acid raw materials with different grain diameters. In the process of grinding solid materials by using the planetary high-energy ball mill, if no ball milling process control agent is added, powder is easy to be accumulated and hardened at the bottom of a ball milling tank, and serious agglomeration, wall adhesion and ball adhesion phenomena occur, so that the powder recovery rate is too low. Under the condition that no ball milling process control agent is added, the powder recovery rate can reach about 90 percent, and the crystal seed preparation method is simple in process, low in energy consumption and good in practicability.
2. Compare in traditional spontaneous nucleation crystallization, the induced crystallization operation adds the dodecatomic acid seed crystal to the supersaturated solution that is in the metastable zone, and the stable of induced solute molecule on the plus crystal nucleus is appeared, has controlled crystal nucleus quantity, has reduced the cladding volume of the inside impurity of crystal, has obtained the great and more even dodecatomic acid product of crystal form of particle size. The average grain diameter of the crystal is 321.56 μm, and the product is more in line with the requirements of dustless and low pulverization of the product outlet in European and American markets.
(IV) description of the drawings
FIG. 1: the comparative figures of the crystal forms of dodecanedioic acid of example 5 and comparative example 1 (non-induced crystallization) of the present application are shown.
FIG. 2: comparative picture of appearance between product of example 14 and dodecanedioic acid product (cat # 22221080737)
(V) detailed description of the preferred embodiments
The present invention will be described in further detail with reference to the following examples. It should not be understood that the scope of the above-described subject matter of the present invention is limited to the following examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
In the following examples 1 to 3, the dodecanedioic acid product with the purity of not less than 99% was sieved by using standard sample sieves of 30, 40, 80 and 100 meshes respectively, and dodecanedioic acid samples (with average particle diameters of 460 μm, 280 μm and 160 μm) with different mesh ranges (30 to 40 meshes, 40 to 80 meshes and 80 to 100 meshes) were obtained and used for mechanical ball milling.
The dodecanedioic acid products, as well as the dodecanedioic acid products in examples 4 to 14 and comparative examples, are all purchased from Shandong Guiyuan Biotech Co., Ltd. (product number: 22221080737), and the purity is not less than 99%.
In examples 1-3, a series of different mesh intervals (100-120 mesh, 120-150 mesh and 200-300 mesh) were passed through a standard sample separation sieve of 100, 120, 150, 200 and 300 mesh to obtain seed crystals of different particle sizes.
In examples 4 to 14 below, the average particle size of dodecanedioic acid crystals was measured by a sieve analysis method using a standard sample sieve of 40, 60, 100, 120, or 200 mesh. In the sieve analysis method, a sample is passed through a series of standard sieves having different mesh numbers, and the sample is sieved into a plurality of particle sizes, which are then weighed, respectively, to obtain a particle size distribution represented by mass fraction. The average particle size of the dodecanedioic acid crystal is calculated according to the following formula:
L＝∑LiVi
in the formula: l is the average particle size of the crystal particles, μm; l isiIs the average grain diameter of each classification interval of the standard sieve, mu m; viIs the mass fraction,%, of crystals in each classification interval. Note: l is1The average grain size is 40-60 meshes, and the average grain size is 352.5 mu m; l is2The average particle size is in the range of 60-100 meshes, and the average particle size is 215 mu m; l is3The average particle size is within the range of 100-120 meshes, and the average particle size is 137.5 mu m; l is4Has an average particle diameter of 120 to 200 mesh, and has an average particle diameter of 100 μm.
Example 1:
under the condition of room temperature, 4g of dodecanedioic acid with purity of more than or equal to 99% and average grain diameter of 460 microns and grinding balls are directly subjected to mechanical ball milling by adopting a mechanical ball milling equipment high-energy planetary ball mill (pulveresette 7, the material of a ball milling tank is stainless steel, the material of the grinding balls is stainless steel, and the diameter of the grinding balls is 8 mm); the ball-material ratio of the mechanical ball milling is 3:1, the rotating speed of the ball mill is 250r/min, and the ball milling time is 60 min; and taking out the ball-milled dodecadibasic acid seed crystal, recovering to obtain 3.5g of powder, wherein the recovery rate of the powder is 87.5%, and obtaining the seed crystal with the particle size of 120-150 mu m by using a 100-120 target standard sample sieve.
Example 2:
under the condition of room temperature, 4g of dodecanedioic acid with the purity of more than or equal to 99 percent and the average grain diameter of 280 mu m and grinding balls are directly subjected to mechanical ball milling by adopting a mechanical ball milling device high-energy planetary ball mill (the material of a ball milling tank is stainless steel; the material of the grinding balls is corundum, and the diameter of the grinding balls is 8 mm); the ball-material ratio of the mechanical ball milling is 3:1, the rotating speed of the ball mill is 200r/min, and the ball milling time is 30 min; and taking out the ball-milled dodecadibasic acid seed crystals, recovering to obtain 3.7g of powder, wherein the recovery rate of the powder is 92.5%, and obtaining the seed crystals with the particle size of 106-120 mu m by using a 120-150-target standard sample sieve.
Example 3:
under the condition of room temperature, 4g of dodecanedioic acid with the purity of more than or equal to 99 percent and the average grain diameter of 160 mu m and grinding balls are directly subjected to mechanical ball milling by adopting a mechanical ball milling device high-energy planetary ball mill (the material of a ball milling tank is stainless steel; the material of the grinding balls is quartz, and the diameter of the grinding balls is 8 mm); the ball-material ratio of the mechanical ball milling is 2:1, the rotating speed of the ball mill is 250r/min, and the ball milling time is 20 min; and taking out the ball-milled dodecadibasic acid seed crystal, recovering to obtain 3.6g of powder, wherein the recovery rate of the powder is 90%, and obtaining the seed crystal with the particle size of 48-75 mu m by using a 200-300-target standard sample sieve.
Example 4:
16g of dodecanedioic acid product and 200mL of 99% acetic acid by volume are mixed in a 250mL three-neck flask, stirred and heated to over 70 ℃ to completely dissolve the dodecanedioic acid, and the stirring speed is 200 r/min. Maintaining the temperature of more than 70 ℃ for 60min, cooling to 44 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the embodiment 2, standing at a constant temperature for crystal growth for 80min, cooling to room temperature after the crystal growth is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry under 0.08MPa until no liquid flows out, taking a filter cake, and drying the filter cake at 85 ℃ to obtain 13.1g of white crystalline dodecanedioic acid, wherein the crystal yield is 81.8%, and the product particle size is measured by adopting a sieve analysis method to obtain the dodecanedioic acid crystal particles with the average particle size of 281.08 microns.
Example 5:
16g of dodecanedioic acid product and 200mL of 99% acetic acid by volume are mixed in a 250mL three-neck flask, stirred and heated to over 70 ℃ to completely dissolve the dodecanedioic acid, and the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 42 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the embodiment 2, standing at a constant temperature for crystal growth for 80min, cooling to room temperature after the crystal growth is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 13.0g of white crystalline dodecanedioic acid, wherein the crystal yield is 81.3%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method to obtain 321.56 mu m.
Example 6:
16g of dodecanedioic acid product and 200mL of 99% acetic acid by volume are mixed in a 250mL three-neck flask, stirred and heated to over 70 ℃ to completely dissolve the dodecanedioic acid, and the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 40 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the embodiment 2, standing at a constant temperature for crystal growth for 80min, cooling to room temperature after the crystal growth is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 12.9g of white crystalline dodecanedioic acid, wherein the crystal yield is 80.3%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method and is 302.29 microns.
Example 7:
mixing 16g of dodecanedioic acid product with 200mL of acetic acid with the volume concentration of 99% in a 250mL three-neck flask, stirring and heating to more than 70 ℃ to completely dissolve the dodecanedioic acid, wherein the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 38 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the embodiment 2, standing at a constant temperature for crystal growth for 80min, cooling to room temperature after the crystal growth is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 12.5g of white crystalline dodecanedioic acid, wherein the crystal yield is 78.3%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method and is 254.41 micrometers.
Example 8:
16g of dodecanedioic acid product and 200mL of 99% acetic acid by volume are mixed in a 250mL three-neck flask, stirred and heated to over 70 ℃ to completely dissolve the dodecanedioic acid, and the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 42 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the embodiment 3, standing at a constant temperature for crystal growth for 80min, cooling to room temperature after the crystal growth is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 13.5g of white crystalline dodecanedioic acid, wherein the crystal yield is 84.4%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method to obtain 300.97 mu m.
Example 9:
16g of dodecanedioic acid product and 200mL of 99% acetic acid by volume are mixed in a 250mL three-neck flask, stirred and heated to over 70 ℃ to completely dissolve the dodecanedioic acid, and the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 42 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the example 1, standing at a constant temperature for crystal growth for 80min, cooling to room temperature after the crystal growth is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 11.5g of white crystalline dodecanedioic acid, wherein the crystal yield is 71.9%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method and is 304.42 microns.
Example 10:
mixing 16g of the dodecanedioic acid product and 200mL of 99% acetic acid by volume in a 250mL three-neck flask, stirring and heating to above 70 ℃ to completely dissolve the crude dodecanedioic acid product, wherein the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 42 ℃, adding 0.04g of the dodecanedioic acid crystal seeds prepared in the example 2, standing at a constant temperature for crystal growth for 80min, cooling to room temperature after the crystal growth is finished to completely separate out the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 12.9g of white crystalline dodecanedioic acid, wherein the crystal yield is 80.9%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method and is 307.16 microns.
Example 11:
mixing 16g of the dodecanedioic acid product and 200mL of 99% acetic acid by volume in a 250mL three-neck flask, stirring and heating to above 70 ℃ to completely dissolve the crude dodecanedioic acid product, wherein the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 42 ℃, adding 0.16g of the dodecanedioic acid crystal seeds prepared in the example 2, standing at a constant temperature for crystal growth for 80min, cooling to room temperature after the crystal growth is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 13.2g of white crystalline dodecanedioic acid, wherein the crystal yield is 82.3%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method and is 312.38 microns.
Example 12:
16g of dodecanedioic acid and 200mL of 99% acetic acid by volume are mixed in a 250mL three-neck flask, stirred and heated to over 70 ℃ to completely dissolve the crude dodecanedioic acid, and the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, then cooling to 42 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the embodiment 2, directly cooling to room temperature without growing crystals to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, and drying at 85 ℃ to obtain 12.6g of white crystalline dodecanedioic acid, wherein the crystal yield is 78.8%, and the product particle size is determined by adopting a sieve analysis method to obtain the dodecanedioic acid crystal particles with the average particle size of 289.28 microns.
Example 13:
mixing 16g of the dodecanedioic acid product and 200mL of 99% acetic acid by volume in a 250mL three-neck flask, stirring and heating to above 70 ℃ to completely dissolve the crude dodecanedioic acid product, wherein the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 42 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the embodiment 2, standing at a constant temperature for crystal growth for 40min, cooling to room temperature after the crystal growth is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 12.9g of white crystalline dodecanedioic acid, wherein the crystal yield is 80.4%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method and is 303.99 microns.
Example 14:
mixing 16g of the dodecanedioic acid product and 200mL of 99% acetic acid by volume in a 250mL three-neck flask, stirring and heating to above 70 ℃ to completely dissolve the crude dodecanedioic acid product, wherein the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to 42 ℃, adding 0.08g of the dodecanedioic acid crystal seeds prepared in the embodiment 2, standing at a constant temperature for growing crystals for 120min, cooling to room temperature after the crystal growing is finished to completely separate the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry at 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 13.3g of white crystalline dodecanedioic acid, wherein the crystal yield is 82.9%, and the average particle size of the dodecanedioic acid crystal particles is determined by a sieve analysis method and is 330.00 microns.
Comparative example 1 (non-induced crystallization):
16g of dodecanedioic acid product and 200mL of 99% acetic acid by volume are mixed in a 250mL three-neck flask, stirred and heated to over 70 ℃ to completely dissolve the dodecanedioic acid, and the stirring speed is 200 r/min. Maintaining the temperature above 70 ℃ for 60min, cooling to room temperature to completely separate out the dodecanedioic acid crystals, carrying out vacuum filtration on crystal slurry under 0.08MPa until no liquid flows out, drying at 85 ℃ to obtain 11.6g of white crystalline dodecanedioic acid, wherein the crystal yield is 72.5%, and the average particle size of the dodecanedioic acid crystal particles is 215.10 mu m by measuring the particle size of the product by a sieve analysis method.
TABLE 1 Effect of examples 1 to 3 of the present invention
TABLE 2, effects of examples 4 to 14 of the present invention
Claims (10)
1. A preparation method of a dodecanedioic acid seed crystal is characterized by comprising the following steps:
mechanically ball-milling irregular dodecanedioic acid crystals A for 20-60 min at a ball-material ratio of 2-5: 1 and a ball-milling rotation speed of 200-400 r/min at room temperature, and sieving with a 100-300-mesh sieve to obtain dodecanedioic acid seed crystals; the diameter of the grinding ball used for the mechanical ball milling is 0.1-20 mm.
2. Use of a dodecanedioic acid seed crystal prepared by the method of claim 1 for preparing a regular dodecanedioic acid crystal.
3. The use according to claim 2, characterized in that the use is: stirring and dissolving irregular dodecanedioic acid B in an organic solvent B at 70-90 ℃ to obtain a supersaturated dodecanedioic acid solution, preserving the temperature for 30-60 min, cooling to 38-44 ℃, adding the dodecanedioic acid seed crystal, cooling to room temperature to completely separate out the crystal, carrying out suction filtration on the obtained crystal slurry, and drying the obtained filter cake to obtain the regular dodecanedioic acid crystal; the mass ratio of the dodecanedioic acid seed crystal to the irregular dodecanedioic acid B is 0.25-1: 100.
4. use according to claim 3, characterized in that: the organic solvent B is C1-2Alcohol, C1-2One or more than two mixed solvents of saturated organic acid, ethyl acetate, butyl acetate, ether and acetone.
5. The use of claim 4, wherein: the organic solvent B is acetic acid.
6. The use according to claim 2, characterized in that the use is: stirring and dissolving irregular dodecanedioic acid C in an organic solvent C at 70-90 ℃ to obtain a supersaturated dodecanedioic acid solution, preserving heat for 30-60 min, cooling to 38-44 ℃, adding the dodecanedioic acid seed crystal, standing at a constant temperature for crystallization for 0-120min, cooling to room temperature to completely separate out crystals, carrying out suction filtration on the obtained crystal slurry, and drying the obtained filter cake to obtain the regular dodecanedioic acid crystals; the mass ratio of the dodecanedioic acid seed crystal to the irregular dodecanedioic acid C is 0.25-1: 100.
7. the use of claim 6, wherein: the organic solvent C is C1-2Alcohol, C1-2One or more than two mixed solvents of saturated organic acid, ethyl acetate, butyl acetate, ether and acetone.
8. The use of claim 7, wherein: the organic solvent C is acetic acid.
9. The use of claim 6, wherein: the time for standing and growing the crystal at constant temperature is 40-120 min.
10. The use of claim 9, wherein: the drying temperature is 60-100 ℃.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329224A (en) * | 2011-09-13 | 2012-01-25 | 淮安清江石油化工有限责任公司 | Method for purifying dodecanedioic acid |
| KR20170036231A (en) * | 2015-09-24 | 2017-04-03 | 롯데케미칼 주식회사 | Purifying method of dodecanedioic acid |
| CN107382709A (en) * | 2017-07-05 | 2017-11-24 | 天津大学 | A kind of aqueous crystallization method of refined SL-AH |
| CN108084015A (en) * | 2017-12-23 | 2018-05-29 | 淄博广通化工有限责任公司 | The process for refining and purifying of dodecanedioic acid |
| CN111848388A (en) * | 2019-04-29 | 2020-10-30 | 中国科学院微生物研究所 | Crystals of dodecanedioic acid and preparation method thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329224A (en) * | 2011-09-13 | 2012-01-25 | 淮安清江石油化工有限责任公司 | Method for purifying dodecanedioic acid |
| KR20170036231A (en) * | 2015-09-24 | 2017-04-03 | 롯데케미칼 주식회사 | Purifying method of dodecanedioic acid |
| CN107382709A (en) * | 2017-07-05 | 2017-11-24 | 天津大学 | A kind of aqueous crystallization method of refined SL-AH |
| CN108084015A (en) * | 2017-12-23 | 2018-05-29 | 淄博广通化工有限责任公司 | The process for refining and purifying of dodecanedioic acid |
| CN111848388A (en) * | 2019-04-29 | 2020-10-30 | 中国科学院微生物研究所 | Crystals of dodecanedioic acid and preparation method thereof |
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