CN111116398B - Method for preparing naphthol AS-LC by micro-channel continuous method - Google Patents
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- CN111116398B CN111116398B CN202010030229.5A CN202010030229A CN111116398B CN 111116398 B CN111116398 B CN 111116398B CN 202010030229 A CN202010030229 A CN 202010030229A CN 111116398 B CN111116398 B CN 111116398B
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- 238000000034 method Methods 0.000 title claims abstract description 16
- QIHKTBRNOLQDGQ-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(NC(=O)C=2C(=CC3=CC=CC=C3C=2)O)=C1OC QIHKTBRNOLQDGQ-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000011437 continuous method Methods 0.000 title claims abstract description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims abstract description 13
- YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims description 24
- 239000000523 sample Substances 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000012295 chemical reaction liquid Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- -1 3-hydroxy-2-naphthoic acid chlorobenzene Chemical compound 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000004321 preservation Methods 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000012488 sample solution Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000007112 amidation reaction Methods 0.000 abstract description 2
- 238000001256 steam distillation Methods 0.000 abstract description 2
- 238000010924 continuous production Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- AQYMRQUYPFCXDM-UHFFFAOYSA-N 3-hydroxy-n-(2-methoxyphenyl)naphthalene-2-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O AQYMRQUYPFCXDM-UHFFFAOYSA-N 0.000 description 1
- FBLAHUMENIHUGG-UHFFFAOYSA-N 3-hydroxy-n-(2-methylphenyl)naphthalene-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O FBLAHUMENIHUGG-UHFFFAOYSA-N 0.000 description 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920006052 Chinlon® Polymers 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- JPVZLJWGZYHBDD-UHFFFAOYSA-N chlorobenzene;trichlorophosphane Chemical compound ClP(Cl)Cl.ClC1=CC=CC=C1 JPVZLJWGZYHBDD-UHFFFAOYSA-N 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- NXIGDUAONGBUKR-UHFFFAOYSA-N n-(2-ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O NXIGDUAONGBUKR-UHFFFAOYSA-N 0.000 description 1
- XWLUFINGMMDFPD-UHFFFAOYSA-N naphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=CC2=C1.C1=CC=C2C(O)=CC=CC2=C1 XWLUFINGMMDFPD-UHFFFAOYSA-N 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Abstract
The invention discloses a method for preparing naphthol AS-LC by a micro-channel continuous method, belonging to the technical field of organic synthesis. The method comprises the following specific steps: and (2) enabling a chlorobenzene solution containing 2-hydroxy-3-naphthoic acid and phosphorus trichloride and a chlorobenzene solution containing 2,5-dimethoxy-4-chloroaniline to enter a microchannel reactor through a metering pump, carrying out amidation reaction at 90-150 ℃, enabling the reaction materials to stay in the reactor for 20-80 s, collecting effluent of the microchannel reactor, and carrying out steam distillation, washing, filtering and the like to obtain the naphthol AS-LC. The method provided by the invention has the advantages of greatly shortened reaction time, simple process, easy operation, high safety, high-yield continuous production, less side reaction and high product quality, and is particularly suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of organic synthesis application, and particularly relates to a method for preparing naphthol AS-LC by a microchannel continuous method.
Background
The Naphthol is commonly called Naphthol (Naphthol) and a primer, and is a component of the ice dyeing dye. Is an important dye intermediate, is mainly used for producing organic pigment and is used for dyeing and printing cotton fibers, viscose fibers and partial synthetic fibers. In printing, a naphthol is used as a primer to perform a coupling reaction with a diazonium salt of a chromophore on a cellulose fiber to form an insoluble azo dye and fix the azo dye to the fiber. A naphthol is often coupled with different chromanium salts to form different azo dyes having different shades and fastnesses. Most varieties of the naphthol are formed by condensing 3-hydroxy-2-naphthoic acid and different arylamines after acyl chlorination, and the derivatives of carbazole, dibenzofuran and anthracene are also included. Such AS naphthol AS-LC, naphthol AS-PH, naphthol AS-OL, naphthol AS-D, etc.
The naphthol AS-LC is also called 3-hydroxy-2-naphthoyl- (4 ' -chloro-2 ',5' -bis-methoxy) aniline, is mainly used for dyeing cotton, viscose fiber, silk, chinlon and terylene, is not generally used for printing, is a base for dyeing orange-yellowish brown, is developed by common yellow base GC and orange base GC, has high affinity to cotton, and is an intermediate for preparing organic pigment. There are two main methods for synthesizing naphthol AS-LC, acid method and sodium salt method. However, the existing synthesis method has the problems of long reaction time, large raw material consumption and serious pollution, and the application of the existing synthesis method is greatly limited. Therefore, a novel, green and high-yield preparation process needs to be developed and designed.
Compared with the traditional batch kettle type reactor, the microchannel reactor has the following characteristics: (1) The microchannel reactor is a special microfabricated reactor, and the characteristic dimension of the microchannel reactor is between dozens of microns and hundreds of microns, so that the diffusion distance between reactants is greatly shortened, the mass transfer speed is high, and the reactants can be fully mixed in a short time in the flowing process. (2) The specific surface area of the microchannel is generally 5000 to 50000 m 2 m -3 The microchannel has large specific surface area, provides more convection heat transfer spaces, can instantly release a large amount of reaction heat to be timely removed even if the reaction is violent in exothermic reaction, maintains the reaction temperature in a safe range, and ensures the safety of the experiment. (3) The microchannel reactor can improve the selectivity of products, obtain high-quality products, reduce the cost, generate few environmental pollutants in the reaction process, and basically have no pollution in a laboratory, thereby being a technical platform for synthesizing and researching new substances and being environment-friendly. (4) The microchannel reactor can be used together with a modern analytical instrument, such as GC, GC-MS, HPLC, LC-MS and NMR, so that the speed of the research synthetic route and the accuracy of the experiment are greatly improved. (5) Various catalysts can be fixed in the micro-channel of the chip to obtain a micro-catalytic bed with high specific surface area, and the catalytic efficiency is improved. (6) When the synthesis reaction is carried out in the microchannel reactor, the reaction conditions such as reactant proportion, reaction time, flow rate and the like can be accurately controlled by a metering pump, and the reaction conditions such as temperature, pressure and the like are integrated by temperature controlAnd (5) controlling the machine. (7) The micro-fluidic chip has the characteristics of high flux, large scale, parallelism and the like, so that the integration and parallel operation of a plurality of or a large number of micro-reactors are possible, the efficiency of synthesizing new substances and screening new medicines is improved, the research cost is greatly reduced, and although the volume of the equipment is smaller, the annual flux can reach 200 to 2000 t/a in a continuous mode.
Therefore, on the basis of producing the naphthol AS-LC by the traditional acid method batch type reaction kettle, the microchannel reactor is used for improving and further optimizing the process, the problem of product selectivity is solved, the yield is greatly improved, and large-batch products with excellent quality are obtained.
Disclosure of Invention
In order to solve the technical problem, the invention provides a method for preparing naphthol AS-LC by a micro-channel continuous method.
A method for preparing naphthol AS-LC by a microchannel continuous method comprises the following steps:
step 1, dissolving 3-hydroxy-2-naphthoic acid in anhydrous chlorobenzene, and heating to 60 ℃ to obtain a chlorobenzene solution of 3-hydroxy-2-naphthoic acid;
dripping a phosphorus trichloride chlorobenzene solution into a 3-hydroxy-2-naphthoic acid chlorobenzene solution by using a constant-pressure dropping funnel, wherein the dripping temperature is 40-120 ℃, the dripping time is 0.5-2 hours, and the heat preservation reaction is 2~4 hours to obtain a sample liquid A;
step 2, adding 2,5-dimethoxy-4-chloroaniline into anhydrous chlorobenzene, and heating until the anhydrous chlorobenzene is completely dissolved to obtain a sample liquid B;
and 3, enabling the sample liquid A and the sample liquid B to enter the microchannel reactor through a metering pump, and controlling the flow rate of the sample liquid A by controlling the flow rate of the metering pump to accurately control the reaction feeding ratio: controlling the flow rate of the sample liquid B at 0.1-2.5 mL/min: carrying out amidation reaction at 90-150 ℃ under 0.1-2.5 mL/min, keeping the reaction material in the reactor for 20-80 s, and collecting the effluent of the microchannel reactor;
and step 4, adding sodium carbonate into the effluent to adjust the pH value to 8, distilling by using water vapor to remove chlorobenzene, washing by using water, filtering, and drying to obtain the naphthol AS-LC.
Wherein the molar ratio of 2,5-dimethoxy-4-chloroaniline, 3-hydroxy-2-naphthoic acid and phosphorus trichloride is 1.
The microchannel reactor in the step 3 is a polytetrafluoroethylene tube microchannel reactor, and the inner diameter of the microreactor is 50-1000 micrometers.
The steam distillation time in the step 4 is 2~5 hours, and the yield is 92 to 98 percent.
The invention has the beneficial effects that:
the microchannel reactor used in the invention is a continuous-flow microchannel reactor, the reaction time is shortened from original 5 hours to dozens of seconds to dozens of minutes at present, the microchannel reactor has high heat transfer efficiency, simple operation and high safety, small inner diameter and large specific surface area, raw materials in the microchannel reactor obtain extremely high yield and product quality, and the microchannel reactor can be continuously reacted in parallel to realize multiple times of amplification without amplification effect.
Drawings
FIG. 1 is a flow chart of microchannel reaction.
Detailed Description
The invention will be further described with reference to specific examples, but the invention is not limited thereto.
Example 1
Step 1, adding 20 g of 3-hydroxy-2-naphthoic acid into a 500 mL three-necked bottle, adding anhydrous chlorobenzene 50 mL, heating to 60 ℃ to obtain a 3-hydroxy-2-naphthoic acid solution;
mixing 7 g phosphorus trichloride with 20 mL chlorobenzene, slowly dripping the mixture into a chlorobenzene solution of 3-hydroxy-2-naphthoic acid by using a constant-pressure dropping funnel for 1 hour, and carrying out heat preservation reaction for 2 hours to prepare a sample solution A;
step 2, weighing 20 g of 2, 5-dimethoxy-4-chloroaniline, adding chlorobenzene 70 mL, and heating until the materials are completely dissolved to obtain sample liquid B;
and 3, enabling the sample liquid A and the sample liquid B to enter the microchannel reactor through a metering pump, and controlling the flow rate of the sample liquid A by controlling the flow rate of the metering pump to accurately control the reaction feeding ratio: 1.5 mL/min, controlling the flow rate of sample liquid B: 1.5 mL/min, heating the reactor to 120 ℃ before feeding, uniformly mixing reaction liquid in the reactor, keeping the reaction liquid for 40 s, and collecting the effluent liquid of the microchannel reactor;
and step 4, adding sodium carbonate into the effluent to adjust the pH value to 8, distilling the effluent by using water vapor to remove the solvent, washing the effluent by using water, filtering the effluent, and drying the effluent to obtain white solid powder with the yield of 96.1 percent.
Example 2
Step 1, adding 20 g of 3-hydroxy-2-naphthoic acid into a 500 mL three-necked bottle, adding anhydrous chlorobenzene 50 mL, heating to 60 ℃ to obtain a chlorobenzene solution of 3-hydroxy-2-naphthoic acid;
mixing 8 g phosphorus trichloride with 20 mL chlorobenzene, slowly dripping the mixture into a chlorobenzene solution of 3-hydroxy-2-naphthoic acid by using a constant-pressure dropping funnel for 1 hour, and carrying out heat preservation reaction for 2 hours to prepare a sample solution A;
step 2, weighing 20 g of 2, 5-dimethoxy-4-chloroaniline, adding chlorobenzene 70 mL, and heating until the materials are completely dissolved to obtain sample liquid B;
and 3, enabling the sample liquid A and the sample liquid B to enter the microchannel reactor through a metering pump, and controlling the flow rate of the sample liquid A by controlling the flow rate of the metering pump to accurately control the reaction feeding ratio: 1.2 mL/min, control sample liquid B flow rate: 1.2 mL/min, heating the reactor to 120 ℃ before feeding, uniformly mixing reaction liquid in the reactor, keeping the reaction liquid for 55 s, and collecting effluent liquid of the microchannel reactor;
and step 4, adding sodium carbonate into the effluent to adjust the pH value to 8, distilling the effluent by using water vapor to remove the solvent, washing the effluent by using water, filtering the effluent, and drying the effluent to obtain white solid powder with the yield of 97.5 percent.
Claims (1)
1. A method for preparing naphthol AS-LC by a microchannel continuous method is characterized by comprising the following steps:
step 1, adding 20 g of 3-hydroxy-2-naphthoic acid into a 500 mL three-necked bottle, adding anhydrous chlorobenzene 50 mL, and heating to 60 ℃ to obtain a 3-hydroxy-2-naphthoic acid chlorobenzene solution;
mixing 8 g phosphorus trichloride with 20 mL chlorobenzene, slowly dripping the mixture into a chlorobenzene solution of 3-hydroxy-2-naphthoic acid by using a constant-pressure dropping funnel for 1 hour, and carrying out heat preservation reaction for 2 hours to prepare a sample solution A;
step 2, weighing 20 g of 2, 5-dimethoxy-4-chloroaniline, adding chlorobenzene 70 mL, and heating until the materials are completely dissolved to obtain sample liquid B;
and 3, enabling the sample liquid A and the sample liquid B to enter the microchannel reactor through a metering pump, and controlling the flow rate of the sample liquid A by controlling the flow rate of the metering pump to accurately control the reaction feeding ratio: 1.2 mL/min, controlling the flow rate of sample liquid B: 1.2 mL/min, heating the reactor to 120 ℃ before sample injection, uniformly mixing reaction liquid in the reactor, keeping the reaction liquid for 55 s, and collecting effluent liquid of the microchannel reactor;
the microchannel reactor in the step 3 is a polytetrafluoroethylene tube microchannel reactor, and the inner diameter of the microreactor is 50 to 1000 micrometers;
and step 4, adding sodium carbonate into the effluent to adjust the pH value to 8, distilling the effluent by using water vapor to remove the solvent, washing the effluent by using water, filtering the effluent, and drying the effluent to obtain white solid powder with the yield of 97.5 percent.
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| CN113307745A (en) * | 2021-04-06 | 2021-08-27 | 湖北浩元材料科技有限公司 | Production method and system of naphthol AS series products |
| CN113666842A (en) * | 2021-09-23 | 2021-11-19 | 河北凯威恒诚制药有限公司 | Continuous flow teriflunomide preparation process |
| CN113801025B (en) * | 2021-10-18 | 2023-08-25 | 南京先进生物材料与过程装备研究院有限公司 | Method for carrying out reductive amination reaction by adopting microchannel reaction device |
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| CN104447392A (en) * | 2014-11-28 | 2015-03-25 | 济宁阳光化学有限公司 | Preparation method of naphthol AS |
| CN104844470A (en) * | 2015-03-23 | 2015-08-19 | 江苏华益科技有限公司 | Synthesis process of novel green naphthol chromophore type products |
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| CN104447392A (en) * | 2014-11-28 | 2015-03-25 | 济宁阳光化学有限公司 | Preparation method of naphthol AS |
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