CN108117492A - A kind of method for preparing N- ethyl-N hydroxyethyl aniline - Google Patents
A kind of method for preparing N- ethyl-N hydroxyethyl aniline Download PDFInfo
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- CN108117492A CN108117492A CN201711388266.8A CN201711388266A CN108117492A CN 108117492 A CN108117492 A CN 108117492A CN 201711388266 A CN201711388266 A CN 201711388266A CN 108117492 A CN108117492 A CN 108117492A
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- ethyl
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- hydroxyethyl aniline
- aniline
- ethylaniline
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- 238000000034 method Methods 0.000 title claims abstract description 25
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 title claims description 25
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-ethyl-N-phenylamine Natural products CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims abstract description 36
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000010438 heat treatment Methods 0.000 claims abstract description 20
- 229960003080 taurine Drugs 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 5
- 238000010792 warming Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 238000007599 discharging Methods 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical class OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 abstract description 4
- 230000001681 protective effect Effects 0.000 abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 1
- KEDLMUMBOSGJTL-UHFFFAOYSA-N n-ethylaniline Chemical compound [CH2]CNC1=CC=CC=C1 KEDLMUMBOSGJTL-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000006227 byproduct Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- -1 N-ethylaniline-chlorethanol Chemical compound 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- KJESGYZFVCIMDE-UHFFFAOYSA-N 1-chloroethanol Chemical compound CC(O)Cl KJESGYZFVCIMDE-UHFFFAOYSA-N 0.000 description 4
- 208000005156 Dehydration Diseases 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 125000001340 2-chloroethyl group Chemical class [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- AUXJVUDWWLIGRU-UHFFFAOYSA-N CCCC(CO1)OC1=O Chemical compound CCCC(CO1)OC1=O AUXJVUDWWLIGRU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000013532 laser treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of methods for preparing N ethyl n hydroxyethylanilines.This method is using N ethyl aniline, ethylene oxide as raw material, and under solvent-free conditions, under the catalysis of taurine, ramped heating schedule directly synthesizes N ethyl n hydroxyethylanilines, and cooling discharging obtains finished product.This method raw material is easy to get, Atom economy is good, reaction condition is mild, it is environmentally protective, be simple and efficient, suitable for industrialized production.
Description
Technical field
The present invention relates to chemosynthesis technical field, more particularly to a kind of method for preparing N- ethyl-N hydroxyethyl aniline.
Background technology
N- ethyl-N hydroxyethyl aniline is a kind of very important organic intermediate, is widely used in dyestuff, pigment, coloured silk
The industrial circles such as color developer.N- ethyl-N hydroxyethyls aniline can be used for preparing the wearproof paint of laser treatment；It can be used as not
The curing agent of saturated resin, the cross linking agent of Polyester Paint；It is also used as anti-corrosion of metal protective agent.Its ethoxy can greatly improve dye
The dispersion performance in synthetic fibers is expected, in addition, hydroxyl can be made a variety of through ammonolysis, esterification, acetylation, chlorination, dehydration contracting platform
Aniline series derivates and dyestuff intermediate.In short, the purposes of N- ethyl-N hydroxyethyl aniline is very extensive, with the product
Purposes is continually developed, it will become a very promising, very big fine chemical product of market capacity.
The synthetic method of N- ethyl-N hydroxyethyl aniline has following several：
1st, N-ethylaniline-chlorethanol method
N-ethylaniline and chlorethanol are in intensive polar solvent, in the presence of an inorganic base, in 120-130 DEG C of reaction, receive
Rate 90%, but the Waste water is bigger, product must be purified using the method for vacuum distillation.
2nd, N-ethylaniline-carbonic acid ethylene method
Using N-ethylaniline, carbonic acid ethylene ester as raw material, reacted under 170 DEG C, the catalysis of lithium chloride and synthesize product.Carbon
Sour ethylene ester is produced by ethylene oxide and carbon dioxide as raw material.
3rd, N- hydroxyethylanilines-method of acetic acid
Matthias Beller etc. report N- hydroxyethylanilines and acetic acid at 160 DEG C, condition existing for 60bar hydrogen
Under, ruthenium complex catalysis, 18 prepared when small N- ethyl-N hydroxyethyls aniline (J.Am.Chem.Soc.2015,137,
13580-13587).This method, because using high pressure hydrogen, there are great security risks, and the reaction time is also long, receive
Rate only has 70% or so.
4th, N- hydroxyethylanilines-chloroethanes method
N- hydroxyethylanilines are dissolved in intensive polar solvent, in Na3PO4In the presence of KI, chloroethanes gas is passed through,
100 DEG C, product, yield 98% is obtained by the reaction under 3atm.
5th, N-ethylaniline-epoxyethane method
5.1N- ethyl aniline and gaseous ethylene oxide directly add under the catalytic action of acetic acid in temperature for 150-160 DEG C
Into being made, in the technical process, acetic acid is easy to the by-product with product generation esterification, not only influences catalytic effect, but also generates it
Its impurity.
5.2N- ethyl aniline and gaseous ethylene oxide are in ZnCl2-H2Under O catalytic action, react 2h at 60 DEG C or so and obtain
Product, yield 93% or so.There are many this method side reaction, and crude product is more miscellaneous, need to carry out vacuum distillation purification.
5.3N- ethyl aniline and gaseous ethylene oxide NaH2PO4Make catalyst, be made in 150-155 DEG C of reaction, yield
For 88%.
5.4N- ethyl aniline and gaseous ethylene oxide prepare N- ethyl-N- hydroxyls with catalyst is made to toluene sulfuric acid zinc and water
Ethyl aniline, product yield is up to 92.0%.
From the above, it can be seen that current production N- ethyl-N hydroxyethyls aniline is mainly with N-ethylaniline and chloroethene
Alcohol is raw material, back flow reaction or reacts production under high temperature, high pressure with ethylene oxide under normal pressure.Using chlorethanol as original
Material, reaction time is long, and chlorethanol dosage is big, high energy consumption, and " three wastes " processing is difficult, and is raw material with chlorethanol, and two is intermolecular
Hydrogen chloride is removed, Atom economy is also bad；Using ethylene oxide as raw material, it is easy to generate N- polyoxyethylene by-products, also
The etherate of two molecular dehydrations may be generated, catalyst is made using organic acid, can also generate ester by-products, these by-products
All have an impact to the performance of product.
The content of the invention
The object of the present invention is to provide a raw material is easy to get, reaction condition is mild, environmentally protective, the synthesis N- that is simple and efficient
The new method of ethyl-N hydroxyethyl aniline, to solve, environmental pollution present in existing production method is big, is asked more than by-product etc.
Topic.
N- ethyl-N hydroxyethyl aniline is synthesized as the direct addition of raw material using N-ethylaniline and ethylene oxide, is to best suit
Atom economy, but catalyst is generally done using inorganic or organic acid, it is acid too strong, it is easy to generate N- polyoxy second
The etherate of alkenes by-product and two molecular dehydrations makees catalyst using organic acid, can also generate ester by-products, these by-products
Object all has an impact the performance of product.
Taurine is a kind of sulfur-containing amino acid, is the important nutrient of people and animal, is widespread in nature.Ox
The pH value of sulfonic acid is 4.1-5.6, it is synthesized N- second by the present invention for N-ethylaniline and ethylene oxide for the direct addition of raw material
In the reaction of base-N- hydroxyethylanilines, dosage is few, and catalytic effect is very good.
Technical solution of the present invention：
A kind of method for preparing N- ethyl-N hydroxyethyl aniline, includes the following steps：
1) using N-ethylaniline, ethylene oxide as raw material, under solvent-free conditions, under the catalysis of taurine, program liter
Temperature heating, directly synthesizes N- ethyl-N hydroxyethyl aniline；
2) it is after reaction, to be cooled to environment temperature, it discharges to get product.
Preferably, the amount ratio of the substance of step 1) ethylene oxide and N-ethylaniline is 1.00-1.05.
Preferably, catalyst used in step 1) is taurine.
Preferably, in step 1) taurine additive amount be N-ethylaniline quality 0.5%-1%.
Preferably, reaction temperature is 100-150 DEG C in step 1), reaction time 2-6h.
It is further preferred that the reaction temperature in step 1) is 120-140 DEG C, reaction time 3-4h.
Preferably, the reaction temperature in step 1) uses temperature programming, and heating rate is 1.0-1.5 DEG C/min.
It is further preferred that the temperature programming in step 1) is to 90-110 DEG C.
Beneficial effects of the present invention：
The present invention makees catalyst using the taurine mild, nature is widely present, with N-ethylaniline, ethylene oxide
N- ethyl-N hydroxyethyl aniline is synthesized for the direct addition of raw material, there is following beneficial effect：
1st, taurine pH value is 4.1-5.6, and performance is mild, without N- polyoxyethylenes by-product and the ether of two molecular dehydrations
Compound is generated with ester by-products.
2nd, excellent catalytic effect, taurine dosage is few, and the additive amount of taurine is the 0.5%-1% of N-ethylaniline quality,
Even if a small amount of brings product into, also have no impact to product.
3rd, conversion ratio and yield can reach more than 99%, and product purity can reach more than 99.5 %.
4th, temperature programming is to 90-110 DEG C or so, after reaction triggers, because being exothermic reaction, you can stops heating, fully
Using the heat for reacting itself releasing, reaction is allowed to continue, save energy consumption.
5th, because reaction is Atom economy, and any solvent, product need not be added in without the generation of other by-products
It can be without purification.
6th, taurine is a kind of sulfur-containing amino acid, is widely present in organism including people, is people and animal
Important nutrient is widespread in nature, environmental-friendly.
7th, any solvent is not added, and chemical reaction efficiency is high, and the utilization rate of reaction kettle is also high, saves recycling and the place of solvent
Reason, will not be there are the volatilization of solvent, and entire production process can accomplish to discharge without " three wastes ", environmentally protective.
Description of the drawings
The nuclear magnetic resonance map for the N- ethyl-N hydroxyethyl aniline that Fig. 1 embodiments 1 obtain.
Specific embodiment
With reference to embodiment, the invention will be further described, but the scope of protection of present invention is not limited to implement
The scope of example statement.
Embodiment 1
Autoclave is purged with nitrogen, under nitrogen protection, adds in the N-ethylaniline of 121g (1mol), 44g's (1mol)
Ethylene oxide, 1.2g (9.6mmol) taurine, closes high pressure kettle cover, and tightens, and heating is opened, with 1 DEG C/min heating rate liters
Temperature stops heating to 90 DEG C, and reaction temperature is warming up to 100 DEG C of reaction 6h, after the completion of reaction, is cooled to 40 DEG C, discharging obtains N-
Ethyl-N hydroxyethyl aniline 162g, yield 98.2%.1H NMR(400MHz,CDCl3) δ 7.21 (t, J=4.0Hz, 2H), 5.76
(d, J=4.0Hz, 2H), 5.70 (t, J=4.0Hz, 1H), 3.75 (s, 2H), 3.43-3.48 (m, 4H), 2.05 (s, 1H),
1.13 (t, J=4.0Hz, 3H).
Embodiment 2
Autoclave is purged with nitrogen, under nitrogen protection, adds in the N-ethylaniline of 121g (1mol), 46.2g
The ethylene oxide of (1.05mol), 0.6g (4.8mmol) taurine, closes high pressure kettle cover, and tightens, open heating, with 1.5 DEG C/
Min heating rates are warming up to 110 DEG C, stop heating, and reaction temperature is warming up to 140 DEG C of reaction 2h, after the completion of reaction, is cooled to 40
DEG C, discharging obtains N- ethyl-N hydroxyethyl aniline 163.4g, yield 99%.
Embodiment 3
Autoclave is purged with nitrogen, under nitrogen protection, adds in the N-ethylaniline of 121g (1mol), 46.2g
The ethylene oxide of (1.05mol), 0.91g (7.3mmol) taurine, closes high pressure kettle cover, and tightens, and heating is opened, with 1.3
DEG C/min heating rates are warming up to 100 DEG C, stop heating, reaction temperature is warming up to 130 DEG C of reaction 3.5h, cold after the completion of reaction
But to 40 DEG C, discharging obtains N- ethyl-N hydroxyethyl aniline 163.8g, yield 99.3%.
Embodiment 4
Autoclave is purged with nitrogen, under nitrogen protection, adds in the N-ethylaniline of 121g (1mol), 45.3g
The ethylene oxide of (1.03mol), 1.0g (8.0mmol) taurine, closes high pressure kettle cover, and tightens, open heating, with 1.1 DEG C/
Min heating rates are warming up to 105 DEG C, stop heating, and reaction temperature is warming up to 136 DEG C of reaction 3.2h, after the completion of reaction, is cooled to
40 DEG C, discharging obtains N- ethyl-N hydroxyethyl aniline 163.7g, yield 99.2%.
Embodiment 5
Autoclave is purged with nitrogen, under nitrogen protection, adds in the N-ethylaniline of 24.2kg (200mol), 8.9kg
The ethylene oxide of (202mol), 242g (1.9mol) taurine, closes high pressure kettle cover, and tightens, and heating is opened, with 1 DEG C/min
Heating rate is warming up to 102 DEG C, stops heating, and reaction temperature is warming up to 133 DEG C of reaction 4.0h, after the completion of reaction, is cooled to 40
DEG C, discharging obtains N- ethyl-N hydroxyethyl aniline 32.8kg, yield 99.4%.
The above embodiments are only the preferred technical solution of the present invention, and are not construed as the limitation for the present invention, this Shen
Please in embodiment and embodiment in feature in the case where there is no conflict, can mutually be combined.The protection model of the present invention
Enclosing should be with the technical solution of claim record, the equivalent substitution side of technical characteristic in the technical solution recorded including claim
Case is protection domain.Equivalent substitution i.e. within this range is improved, also within protection scope of the present invention.
Claims (8)
- A kind of 1. method for preparing N- ethyl-N hydroxyethyl aniline, it is characterised in that include the following steps：1) using N-ethylaniline, ethylene oxide as raw material, under solvent-free conditions, under the catalysis of taurine, temperature programming adds Heat directly synthesizes N- ethyl-N hydroxyethyl aniline；2) it is after reaction, to be cooled to environment temperature, it discharges to get product.
- 2. the method that application according to claim 1 directly synthesizes N- ethyl-N hydroxyethyl aniline, it is characterised in that：Step The amount ratio of the substance of rapid 1) ethylene oxide and N-ethylaniline is 1.00-1.05.
- 3. the method that application according to claim 1 directly synthesizes N- ethyl-N hydroxyethyl aniline, it is characterised in that：Step It is rapid 1) in used catalyst be taurine.
- 4. the method that application according to claim 1 directly synthesizes N- ethyl-N hydroxyethyl aniline, it is characterised in that：Step It is rapid 1) in taurine additive amount be N-ethylaniline quality 0.5%-1%.
- 5. the method that application according to claim 1 directly synthesizes N- ethyl-N hydroxyethyl aniline, it is characterised in that：Step It is rapid 1) in reaction temperature be 100-150 DEG C, reaction time 2-6h.
- 6. the method that application according to claim 5 directly synthesizes N- ethyl-N hydroxyethyl aniline, it is characterised in that：Step It is rapid 1) in reaction temperature be 120-140 DEG C, reaction time 3-4h.
- 7. the method that application according to claim 1 directly synthesizes N- ethyl-N hydroxyethyl aniline, it is characterised in that：Step It is rapid 1) in reaction temperature using temperature programming, heating rate is 1.0-1.5 DEG C/min.
- 8. the method that application according to claim 7 directly synthesizes N- ethyl-N hydroxyethyl aniline, it is characterised in that：Step It is rapid 1) in temperature programming be warming up to 90-110 DEG C.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590574A (en) * | 2019-10-09 | 2019-12-20 | 绍兴君泰纺织科技有限公司 | Preparation method of organic intermediate N-ethyl-N-beta-hydroxypropyl m-toluidine |
| CN110590573A (en) * | 2019-09-23 | 2019-12-20 | 武汉奥克特种化学有限公司 | Preparation method of high-purity N-ethyl-N-hydroxyethyl-m-toluidine |
| CN113444019A (en) * | 2021-08-02 | 2021-09-28 | 浙江闰土染料有限公司 | Preparation method of N-cyanoethyl-N-acetoxyethylaniline |
-
2017
- 2017-12-20 CN CN201711388266.8A patent/CN108117492A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590573A (en) * | 2019-09-23 | 2019-12-20 | 武汉奥克特种化学有限公司 | Preparation method of high-purity N-ethyl-N-hydroxyethyl-m-toluidine |
| CN110590573B (en) * | 2019-09-23 | 2022-09-23 | 武汉奥克特种化学有限公司 | Preparation method of high-purity N-ethyl-N-hydroxyethyl-m-toluidine |
| CN110590574A (en) * | 2019-10-09 | 2019-12-20 | 绍兴君泰纺织科技有限公司 | Preparation method of organic intermediate N-ethyl-N-beta-hydroxypropyl m-toluidine |
| CN113444019A (en) * | 2021-08-02 | 2021-09-28 | 浙江闰土染料有限公司 | Preparation method of N-cyanoethyl-N-acetoxyethylaniline |
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