CN107286041A - A kind of preparation method of N, N- diethylformamide - Google Patents
A kind of preparation method of N, N- diethylformamide Download PDFInfo
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- CN107286041A CN107286041A CN201610201184.7A CN201610201184A CN107286041A CN 107286041 A CN107286041 A CN 107286041A CN 201610201184 A CN201610201184 A CN 201610201184A CN 107286041 A CN107286041 A CN 107286041A
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- Prior art keywords
- diethylamine
- diethylformamides
- formic acid
- preparation
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- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 21
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 18
- 235000019253 formic acid Nutrition 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052593 corundum Inorganic materials 0.000 claims abstract description 9
- 229910001845 yogo sapphire Inorganic materials 0.000 claims abstract description 9
- 239000000047 product Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 239000003039 volatile agent Substances 0.000 claims description 4
- WNCAVNGLACHSRZ-KAMYIIQDSA-N Allithiamine Chemical compound C=CCSSC(/CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N WNCAVNGLACHSRZ-KAMYIIQDSA-N 0.000 claims description 2
- WNCAVNGLACHSRZ-UHFFFAOYSA-N Allithiamine Natural products C=CCSSC(CCO)=C(C)N(C=O)CC1=CN=C(C)N=C1N WNCAVNGLACHSRZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000013019 agitation Methods 0.000 claims description 2
- 239000004005 microsphere Substances 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 claims description 2
- 229960000344 thiamine hydrochloride Drugs 0.000 claims description 2
- 235000019190 thiamine hydrochloride Nutrition 0.000 claims description 2
- 239000011747 thiamine hydrochloride Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000007791 liquid phase Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229920001986 Vinylidene chloride-vinyl chloride copolymer Polymers 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
- B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of N, the preparation method of N diethylformamides uses formic acid with diethylamine for raw material, formic acid is with diethylamine according to mol ratio 1:1, use Al2O3/VB1Complex catalyst system, reacted liquid phase mixture removes excessive formic acid and catalyst and micro diethylamine, then carries out rectification under vacuum in rectifying column, obtains the N that purity is more than 99.9%, N diethylformamides.The preparation method uses normal pressure reactor, distilling apparatus and rectifier unit, and is heated with microwave, shortens the reaction time, diethylamine conversion ratio is improved, product purity is high, and production cost is low, it is easy to operate, it can rapidly synthesize the N of high-quality, N diethylformamides.
Description
Technical field
The invention belongs to the preparation method of chemical products technical field of organic synthesis, more particularly to a kind of N, N- diethylformamide.
Background technology
With the emergence of new technology, fine chemical product plays more and more important in the development of national economy industry-by-industry
Effect.N, N- diethylformamide (vehicle economy F) be water white transparency low-density high boiling point polar organic solvent, with water and
The solution such as alcohol, ether, ketone, benzene, with very strong dissolubility, can dissolve many organic polymers, such as polyacrylonitrile, amino first
The high molecular polymerizations such as acetoacetic ester prepolymer, PVC, vinylidene chloride-vinyl chloride copolymer, polyvinyl formal, polyimides
Thing；Solvent, extractant are industrially commonly used for, is the fine solvent of synthetic crystal, metal-organic framework materials synthetic,
It is used as solvent of the novel absorbent refrigeration working medium to (R22-DEF), efficient solvent for lithium etc.；And in the middle of organic synthesis
Body, such as synthetic drug fumaric acid make radical protection reagent for sulphur good fortune Wei ester.
Along with the application study of DEF products, have between DEF and aromatic hydrocarbon molecule great dipole and dipole inducing action and
Electric charge transfer act on, the aromatic hydrocarbons liquid-crystal compounds by Material synthesis of electron level DEF can not only influence molecule polarity and
Geometric configuration, so as to influence the phase transition temperature of liquid crystal, can also make dipole moment direction and size, the dielectric anisotropy of molecule
Symbol and size etc. change, thus the liquid crystal material synthesized by intermediate of electron level DEF is in the work(of design synthesizing new
It can be played an important role in terms of material.There is relatively low viscosity due to the liquid crystal material synthesized by intermediate of electron level DEF, it is suitable
In birefringence, aobvious compared with wide liquid crystal phase temperature interval, excellent combination property, high, the big, armaticity of dipole moment of stability etc.
Advantage is write, is suitable for various high-grade liquid crystal display modes, as currently most the liquid crystal material intermediate of market potential, electronics
Level DEF is as a kind of excellent LCD material key intermediate products, and its synthesis technique, which turns into one, is worth the new problem of research.
The content of the invention
The purpose of the present invention is in view of the shortcomings of the prior art and provides a kind of N, the preparation method of N- diethylformamides, its profit
Reacted with diethylamine and formic acid, using composite catalyst system, this synthetic reaction condition is gentle, product purity is high and yield, reduction
Production cost, and simplify operating process.
In order to solve the above-mentioned technical problem, the present invention is accomplished by the following way：
The preparation method of a kind of N, N- diethylformamide, specifically includes following steps：
Step 1) formic acid is added into microwave reactor first, magnetic agitation is opened, diethylamine is added in microwave reactor
Even stirring mixed liquor；
Step 2) by catalyst salt allithiamine (abbreviation VB1) add step 1) and microwave reactor in, and with 40~400W
Power microwave be heated to after 30~50 DEG C, stirring reaction 30min, then temperature is heated with 100~600W power microwave
To after 90~100 DEG C, catalyst Al is added2O3Reaction 1~2 hour；
Step 3) after above-mentioned reaction terminates, first 90~100 DEG C of temperature of control distills out front-end volatiles at ambient pressure, and front-end volatiles are
The N that purity is 96~98%, N- diethylformamides are obtained in excessive formic acid and catalyst and micro diethylamine, distillation still
Crude product；
Step 4) N that comes out above-mentioned air-distillation, N- diethylformamides crude product again by rectification under vacuum, rectification under vacuum
Vacuum degree control is -0.05~-0.06mMPa, returns and evaporates than for 1:1~1:2, recovered (distilled) temperature is 90~100 DEG C, after rectification under vacuum
Obtain the N that purity is more than 99.9%, N- diethylformamides essence product.
It is preferred that, step 1) in formic acid and diethylamine according to mol ratio 1:1 ratio is mixed.
Further, step 2) in add the amount of thiamine hydrochloride for formic acid and diethylamine quality and 1%~5%；Al2O3For γ
Crystal-type aluminum oxide micro-sphere, granularity is less than 20 microns, 1.0~1.5cm of pore volume3/ g, addition be formic acid and diethylamine quality and
1~5%.
Compared with prior art, the device have the advantages that：
1st, N of the invention, the preparation method of N- diethylformamides have selected composite catalyst system Al2O3And VB1, catalysis effect
Rate is higher；γ-crystal type Al2O3It is the porous alumina solid of a class, the big (about 200~600m of specific surface area2/ g),
With very strong adsorption capacity and catalytic activity, VB1It is a kind of new catalyst of environmental protection, is widely used in all kinds of acyls
Change in reaction, by the way that the two is compounded, be effectively promoted the acetylization reaction process of formic acid and diethylamine, N, N- diethyl first
Acid amides high purity 99.9%；
2nd, the present invention is carried out under the conditions of microwave radiation, compared to conventional heating methods have reaction rate fast, high conversion rate,
The advantages of inside is heated, cleaned, saving, system is easy to control, with good prospects for commercial application；
3rd, the preparation method, input cost is small, and raw material is simple and easy to get, and operating condition is gentle, and its synthesis technique is simple, safety
Property is good.
Embodiment
The present invention is specifically described below by embodiment, it is necessary to it is pointed out here that be that the present embodiment is served only for the present invention
It is further described, but it is not intended that limiting the scope of the invention.The person skilled in the art in the field can basis
The content of the invention described above makes some nonessential modifications and adaptations.
Embodiment 1：
46 kilograms of technical grade formic acid (1.0kmol) is added the stainless steel microwave reaction with stirring, thermometer and reflux condenser
In device, 74 kilograms of technical grade diethylamine (1.0kmol) is slowly added under normal temperature into microwave reactor；By levigate 5 kilograms
Catalyst VB1Add stirring reaction in the above-mentioned microwave reactor equipped with reaction raw materials, controlling reaction temperature at 30~50 DEG C,
React after 30min, add 5 Kg of powder shape Al2O3And lifted reaction temperature to 90~100 DEG C react 1 hour；Treat anti-
After should being fully completed, 90~100 DEG C of distillations of temperature are controlled at ambient pressure, obtain N, the crude product of N- diethylformamides will
The crude product of N, N- diethylformamide is by rectification under vacuum, and the vacuum degree control of rectification under vacuum is -0.05~-0.06mMPa, is returned
Evaporate than for 1:1~1:2, recovered (distilled) temperature is 90~100 DEG C, obtains N, N- diethylformamide finished products.Collect product and analyze,
Diethylamine conversion ratio is 98.9%, N, and N- diethylformamide finished products purity is 99.93%.
Embodiment 2：
23 kilograms of technical grade formic acid (0.5kmol) add with stirring, thermometer, reflux condenser stainless steel microwave reaction
In device, 37 kilograms of technical grade diethylamine (0.5kmol) is slowly added under normal temperature into microwave reactor；By levigate 2.5 kilograms
Catalyst VB1Stirring reaction in the above-mentioned microwave reactor equipped with reaction raw materials is added, controlling reaction temperature is 30~50 DEG C,
React after 30min, add 2.5 Kg of powder shape Al2O3Lifted reaction temperature to 90~100 DEG C react 1.5 hours, treat
After reaction is fully completed, 90~100 DEG C of distillations of temperature are controlled at ambient pressure, obtain N, the crude product of N- diethylformamides will
The thick production of N, N- diethylformamide is by rectification under vacuum, and the vacuum degree control of rectification under vacuum is -0.05~-0.06mMPa, returns and evaporates
Than for 1:1~1:2, recovered (distilled) temperature is 90~100 DEG C, obtains N, N- diethylformamide finished products.Collect product and analyze, two
Ethamine conversion ratio 99.8%, N, N- diethylformamide finished products purity 99.99%.
Embodiment 3：
13.8 kilograms of technical grade formic acid (0.3kmol) is added the stainless steel microwave with stirring, thermometer, reflux condenser anti-
Answer in device, be slowly added to 22.2 kilograms of technical grade diethylamine (0.3kmol) under normal temperature into microwave reactor；By levigate 1.5
Kilogram catalyst VB1Add stirring reaction in the above-mentioned microwave reactor equipped with reaction raw materials, controlling reaction temperature for 30~
50 DEG C, react after 30min, add 1.5 Kg of powder shape Al2O3And it is small to 90~100 DEG C of reactions 2 to lift reaction temperature
When；After question response is fully completed, 90~100 DEG C of distillations of temperature are controlled at ambient pressure, N, the thick production of N- diethylformamides is obtained
Product, by N, the crude products of N- diethylformamides by rectification under vacuum, the vacuum degree control of rectification under vacuum for -0.05~
- 0.06mMPa, returns and evaporates than for 1:1~1:2, recovered (distilled) temperature is 90~100 DEG C, obtains N, N- diethylformamide finished products.Receive
Collection product is simultaneously analyzed, diethylamine conversion ratio 99.9%, N, N- diethylformamide finished products purity 99.99%.
Described above is only embodiments of the present invention, is stated again, for those skilled in the art,
Without departing from the principles of the invention, some improvement can also be carried out to the present invention, these improvement are also included in right of the present invention will
In the protection domain asked.
Claims (4)
1. the preparation method of a kind of N, N- diethylformamide, it is characterised in that：Specifically include following steps：
Step 1) formic acid is added into microwave reactor first, magnetic agitation is opened, diethylamine is added in microwave reactor
Even stirring mixed liquor；
Step 2) catalyst salt allithiamine is added into step 1) microwave reactor in, and added with 40~400W power microwave
Heat is to 30~50 DEG C, after stirring reaction 30min, then temperature is heated to after 90~100 DEG C with 100~600W power microwave,
Add catalyst Al2O3Reaction 1~2 hour；
Step 3) after above-mentioned reaction terminates, first 90~100 DEG C of temperature of control distills out front-end volatiles at ambient pressure, and front-end volatiles are
The N that purity is 96~98%, N- diethylformamides are obtained in excessive formic acid and catalyst and micro diethylamine, distillation still
Crude product；
Step 4) N that comes out above-mentioned air-distillation, N- diethylformamides crude product again by rectification under vacuum, rectification under vacuum
Vacuum degree control is -0.05~-0.06mMPa, returns and evaporates than for 1:1~1:2, recovered (distilled) temperature is 90~100 DEG C, after rectification under vacuum
Obtain the N that purity is more than 99.9%, N- diethylformamides essence product.
2. a kind of N according to claim 1, the preparation method of N- diethylformamides, it is characterised in that：The step 1)
In formic acid and diethylamine according to mol ratio 1:1 ratio is mixed.
3. a kind of N according to claim 1, the preparation method of N- diethylformamides, it is characterised in that：The step 2)
The middle amount for adding thiamine hydrochloride for formic acid and diethylamine quality and 1%~5%.
4. a kind of N according to claim 1, the preparation method of N- diethylformamides, it is characterised in that：The Al2O3For
γ crystal-type aluminum oxide micro-spheres, granularity is less than 20 microns, 1.0~1.5cm of pore volume3/ g, addition be formic acid and diethylamine quality and
1~5%.
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| CN201610201184.7A CN107286041A (en) | 2016-04-01 | 2016-04-01 | A kind of preparation method of N, N- diethylformamide |
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| 江涛: "具有生物活性的N-（2-嘧啶基）苯甲酰胺类化合物的合成研究", 《中国优秀博硕士学位论文全文数据库（硕士） 工程科技I辑》 * |
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