CN100371313C - Process For Preparing O-Trifluoromethyl Aniline - Google Patents PDF

26/12/2020 CN100371313C - Process for preparing o-trifluoromethyl aniline - Google Patents
Patents
Process for preparing o-tri uoromethyl aniline
Abstract
CN100371313C
The present invention relates to a method for preparing o-tri uoromethyl aniline. Toluene tri uoride
China
is used as raw material and reacts to generate a mixture of meta-chlorobenzotri uoride and Granted Patent
isomers thereof through cyclization chlorination, and then, the obtained mixture is nitri ed to
generate a mixture of 2-nitro-5-chlorobenzotri uoride and isomers thereof. Finally, the obtained Download PDF Find Prior Art Similar
nitri ed mixture reacts to generate a mixture of three isomers with o-tri uoromethyl aniline as a
main component though catalytic hydrogenation and hydrogenolysis dechlorination, and the Other languages: Chinese
mixture is recti ed to obtain pure o-tri uoromethyl aniline. The method of the present invention has
Inventor: 王千杰
the characteristics of short synthetic route, advanced technology, high yield, favourable effect,
simple and convenient industrialized production, etc.
Worldwide applications
2004 CN
Application CNB2004100169586A events
2004-03-12 Application led by 浙江省东阳市巍华化工有限

公司
2004-03-12 Priority to CNB2004100169586A
2005-09-14 Publication of CN1666974A
2008-02-27 Application granted
2008-02-27 Publication of CN100371313C
Info: Patent citations (2), Cited by (4), Legal events, Similar

documents, Priority and Related Applications
External links: Espacenet, Global Dossier, Discuss
https://patents.google.com/patent/CN100371313C/en 1/13
Claims (7) Hide Dependent
1. the preparation method of an o-tri uoromethyl aniline is a raw material with the phenyl uoroform, comprises three-step reaction and corresponding technological process:
1. in the presence of iron powder or ferric chloride catalyst, phenyl uoroform and chlorine initial ring chlorination reaction, obtain with meta-chlorobenzotri uoride be main
content the neighbour,, to three kinds of mixture of isomers;
2. with the meta-chlorobenzotri uoride and the mixture of isomers thereof of the rst step cyclization gained, in the presence of the vitriol oil, with nitrosonitric acid generation
nitration reaction, obtaining with 2-nitro-5-chlorobenzotri uoride is the multiple mixture of isomers of main content;
3. 2-nitro-5-chlorobenzotri uoride that the second step nitration reaction is obtained is the multiple mixture of isomers of main content, in
Granted
the presence
Patent of solvent, catalyzer
and acid binding agent, with hydrogen generation catalytic hydrogenation-hydrogenolysis dechlorination reaction, generation with o-tri uoromethyl aniline be main content the
neighbour,, to three kinds of mixture of isomers, through distillation, obtain pure o-tri uoromethyl aniline, simultaneously, also obtain the m-tri uoromethyl aniline of a part;
Wherein catalyst system therefor is 5% Pd/C, and consumption is counted 0.8～2g with the 1mol nitration product; Used acid binding agent is the magnesium powder, and its
consumption is counted 0.5～0.502mol with the 1mol nitration product.
2. the preparation method of o-tri uoromethyl aniline according to claim 1, the catalyst consumption that it is characterized in that encircling chlorination reaction is 1
～5% of a phenyl uoroform molar percentage, temperature of reaction is 0 ℃～40 ℃.
3. the preparation method of o-tri uoromethyl aniline according to claim 1 and 2, the temperature that it is characterized in that nitration reaction is 10 ℃～50 ℃.
4. the preparation method of o-tri uoromethyl aniline according to claim 1 and 2 is characterized in that in catalytic hydrogenation-hydrogenolysis dechlorination
reaction, solvent for use is an aqueous methanol.
5. the preparation method of o-tri uoromethyl aniline according to claim 3 is characterized in that in catalytic hydrogenation-hydrogenolysis dechlorination reaction,
solvent for use is an aqueous methanol.
6. according to the preparation method of claim 1 or 2 or 5 described o-tri uoromethyl anilines, it is characterized in that catalytic hydrogenation-hydrogenolysis
dechlorination reaction temperature is 40 ℃～80 ℃, reaction pressure is 0.5～1.0MPa.
7. the preparation method of o-tri uoromethyl aniline according to claim 3 is characterized in that catalytic hydrogenation-hydrogenolysis dechlorination reaction
temperature is 40 ℃～80 ℃, and reaction pressure is 0.5～1.0MPa.
Description
The preparation method of o-tri uoromethyl aniline
Technical eld
The present invention relates to a kind of preparation method of product, the hydrogenolysis dechlorination technology of chlorine atom on especially a kind of
preparation method of o-tri uoromethyl aniline and the aromatic ring.
Background technology
O-tri uoromethyl aniline is a kind of important organic synthesis intermediate, is mainly used in the synthetic of dyestuff and agricultural chemicals.For example o-
tri uoromethyl aniline can be used for synthesizing acyl dihydroxy-benzene azoic dyestuff, and this dyestuff is used for polyole ne, and the particularly dyeing of
polypropylene fabric can produce strong vivid tone, and fast colours, and is colour-fast.O-tri uoromethyl aniline can be used for synthetic N-alkyl diphenyl aminated
compounds for another example, and this compound can be used for making and belong to agent and sterilant extremely.
Preparation about o-tri uoromethyl aniline; people such as Forbes are raw material with m-tri uoromethyl aniline; through acylations, nitrated, hydrolysis, diazotization,
Granted Patent
take off ve steps reaction such as diazo and make adjacent nitro-tri uoromethyl toluene, in the presence of the Raney nickel catalyzer, carry out catalytic
hydrogenation then and then obtain o-tri uoromethyl aniline.People such as Maginnity P.M. have also made o-tri uoromethyl aniline with same synthetic route, and just
the nal step reduction reaction adopts the method for chemical reduction.In addition, disclosed patent had announced once also that with Raney nickel or
palladium/charcoal be catalyzer, with yellow soda ash, triethylamine etc. is acid binding agent, and 2-tri uoromethyl-4-chloroaniline is carried out the hydrogenolysis
dechlorination or 2-nitro-5-chlorobenzotri uoride is carried out catalytic hydrogenation preparing o-tri uoromethyl aniline.People such as Henry C.L. were raw material
with the o-tri uoromethyl phenyl isocyanate once, prepared o-tri uoromethyl aniline with the hydro uoric acid reaction via o-tri uoromethyl phenyl amino formyl
uoride.But the above method for preparing o-tri uoromethyl aniline, the synthetic route that has is oversize, and the raw material that has is di cult to obtain, and the
Technology that has is not good enough, all is not a kind of ideal production method.
Summary of the invention
It is longer to the invention solves the existing in prior technology synthetic route, and raw material is not easy to obtain, the technical problem of grade that Technology
is not good enough, provide a kind of convenience, economy, can be for the preparation method of the o-tri uoromethyl aniline of suitability for industrialized
production.
Above-mentioned technical purpose of the present invention solves by the following technical programs: a kind of preparation method of o-tri uoromethyl aniline is a
raw material with the phenyl uoroform, comprises three-step reaction and corresponding technological process:
1. in the presence of iron powder or ferric chloride catalyst, phenyl uoroform and chlorine initial ring chlorination reaction, obtain with meta-chlorobenzotri uoride be
main content the neighbour,, to three kinds of mixture of isomers;
2. with the meta-chlorobenzotri uoride and the mixture of isomers thereof of the rst step cyclization gained, in the presence of the vitriol oil, with nitrosonitric acid
generation nitration reaction, obtaining with 2-nitro-5 chlorobenzotri uoride is the multiple mixture of isomers of main content;
3. 2-nitro-5-chlorine three that the second step nitration reaction is obtained is tied up the multiple mixture of isomers that toluene is main content, in the presence of
solvent, catalyzer, acid binding agent, with hydrogen generation catalytic hydrogenation-hydrogenolysis dechlorination reaction, generation with o-tri uoromethyl aniline
be main content the neighbour,, to three kinds of mixture of isomers, through distillation, obtain pure o-tri uoromethyl aniline, simultaneously, can also obtain the m-
tri uoromethyl aniline of a part.
Method of the present invention is to be raw material with the phenyl uoroform, in the presence of iron powder or iron trichloride, generates meta-
chlorobenzotri uoride and mixture of isomers thereof through the ring chlorination reaction.Then this mixture is carried out nitration reaction and generate 2-nitro-5-
chlorobenzotri uoride and mixture of isomers thereof.At last, the resulting mixture of nitration reaction is carried out catalytic hydrogenation-hydrogenolysis
dechlorination reaction in the presence of Pd/carbon catalyst and magnesium powder, generate with o-tri uoromethyl aniline be main content the neighbour,, to three
kinds of mixture of isomers.This mixture is carried out rectifying just can obtain pure o-tri uoromethyl aniline.Be expressed as down with chemical equation:
The gordian technique that the present invention prepares o-tri uoromethyl aniline is to slough benzene chlorine in ring atom by hydrogenolysis, i.e. hydrogenolysis
dechlorination technology.Disclosed dechlorination method has multiple, and for example, people such as Bryce-Smith slough benzene chlorine in ring atom with
magnesium powder and Virahol and chlorobenzene reaction in the presence of naphthane.But be to use more dechlorination method still to adopt the method for
catalyzer hydrogenolysis, and the hydrogenolysis dechlorination all is to be catalyzer (making catalyzer with Raney nickel poisons easily) with palladium/charcoal
Granted
usually, with sodium hydroxide, yellow soda ash, sodium-acetate, triethylamine etc. is acid binding agent, need to use relatively large Pd/carbon Patent
catalyst in this way yet
make, dechlorination sometimes is also incomplete.Our the hydrogenolysis dechlorination technology of invention is solvent with the aqueous methanol, carries out the
hydrogenolysis dechlorination in the presence of Pd/carbon catalyst and magnesium powder, and the hydrogenolysis dechlorination only need use the Pd/carbon
catalyst of minute quantity just can reach good dechlorination effect in this way.Among the present invention, the magnesium powder is not only acid binding agent, is
used for the hydrogenchloride that generates in the absorption reaction, also participates in dechlorination reaction simultaneously.
As preferably, the preparation method of described o-tri uoromethyl aniline, the temperature of reaction of ring chlorination reaction is 0 ℃～40 ℃, reaction times is 7～
12 hours, used catalyzer is iron powder or iron trichloride in the reaction, and catalyst consumption is 1～3% (in phenyl uoroform, mol ratio).Whether reaction is
nished, and can determine by the gas chromatographic analysis to reaction solution.After the reaction, rush to remain in chlorine and hydrogen chloride gas in the
reaction solution, remove by lter catalyzer, ltrate rectifying with pressurized air.Collect meta-chlorobenzotri uoride and mixture of isomers cut thereof.
As preferably, the preparation method of described o-tri uoromethyl aniline, the temperature of reaction of nitration reaction are 10 ℃～50 ℃, and the reaction times is
2～5 hours.The consumption of 95% nitrosonitric acid is 1～1.2mol (in a 1mol chloro phenyl uoroform), the consumption of 98% the vitriol oil is 1.5～4mol (in a 1mol
chloro phenyl uoroform), after the nitration reaction, tell lower oor's spent acid, the upper strata nitration product washs with suitable quantity of water, and it is the
multiple mixture of isomers of main content that neutralization is with 2-nitro-5-chlorobenzotri uoride.
As preferably, the preparation method of described o-tri uoromethyl aniline, in catalytic hydrogenation-hydrogenolysis dechlorination reaction, solvent for use is an
aqueous methanol; Catalyst system therefor is 5%Pd/C, and consumption is 0.8～2g (in a 1mol chloro nitro-tri uoromethyl toluene); Used acid binding agent is the
magnesium powder, and its consumption is 0.5～0.502mol (in a 1mol chloro nitro-tri uoromethyl toluene); Temperature of reaction is 40 ℃～80 ℃, and reaction
pressure is 0.5～1.0Mpa, 2～4 hours reaction times.After reaction nished, cooling removed by lter catalyzer and remaining magnesium powder, and methyl alcohol is
reclaimed in the ltrate distillation, and cooling distillation residual solution is told lower oor's magnesium chloride brine, carries out rectifying after the upper strata
hydrogenation products washes with water, then can obtain pure o-tri uoromethyl aniline.
Therefore, the present invention have that synthetic route is short, technology is advanced, yield is high, effective, characteristics such as suitability for industrialized
production is simple and easy to do.
Embodiment
Below by speci c embodiment, and in conjunction with the accompanying drawings, technical scheme of the present invention is described in further detail.
The ring chlorination reaction:
Embodiment 1: in 1000 ml asks, drop into the 400g phenyl uoroform, the 10g iron trichloride, keeping temperature of reaction is 10～15 ℃, stirs down and feeds
chlorine 9 hours, and reaction is nished, catch up with chlorine residual in the reaction ask and hydrogen chloride gas with pressurized air, remove by lter catalyzer,
ltrate is through gas chromatographic analysis, and the content of each component is: 4.8% phenyl uoroform, 72.8% meta-chlorobenzotri uoride, 4.2%
chlorobenzotri uoride, 6.2% p-chloro benzo tri uoride-99,12% is polychloride.Recti cation process liquid is collected 120～130 ℃/0.04Mpa (vacuum tightness) cut, be
with meta-chlorobenzotri uoride be main content the neighbour,, to three kinds of mixture of isomers.
Embodiment 2-5 is with embodiment 1.
The principal reaction condition is to the quantized data table of reaction in uence in the table 1 ring chlorination reaction
Granted Patent
The nitration reaction of meta-chlorobenzotri uoride and mixture of isomers thereof:
Embodiment 1: in the 1000ml ask, drop into the vitriol oil of 210g, under the cold water cooling, drip the 104.4g nitrosonitric acid, under 10～15 ℃ of maintenance
temperature of reaction, drip 270.7g meta-chlorobenzotri uoride and mixture of isomers thereof, about 1 hour of dropping time.Drip and nish, reacted 2 hours down at
45～50 ℃, after having reacted, tell lower oor's spent acid, the upper strata nitration product is after water washing, neutralization, and being with 2-nitro-5-
chlorobenzotri uoride is the multiple mixture of isomers of main content, and content is 79.6%.
The principal reaction condition is to the quantized data table of reaction in uence in table 2 nitration reaction
Catalytic hydrogenation-hydrogenolysis dechlorination reaction:
Embodiment 1: in one liter autoclave, drop into 225g 2-nitro-5-chlorobenzotri uoride and mixture of isomers thereof, 600ml methyl alcohol, 1g Pd/C catalyzer, 12g
magnesium powder.Build kettle cover, catch up with in the autoclave air three times with nitrogen, use hydrogen exchange nitrogen again three times, pour hydrogen
then, pressure is 0.5～1.0MPa.Under 40～50 ℃ of temperature of reaction, reacted 40～60 minutes, reacted 1.5～2 hours down at 65～75 ℃ then.Reaction is nished,
cooling, and reaction solution is taken out in release, removes by lter Pd/C catalyzer and small portion of residual magnesium powder.Methyl alcohol is reclaimed in
the ltrate distillation, after the distillation residuum cools off slightly, tells the aqueous solution of lower oor's magnesium chloride.Distill after the upper strata
hydrogenation products washes with water, collect 80～100 ℃.The cut of (0.098MPa vacuum tightness), be the neighbour,, three kinds of mixture of isomers of p-
tri uoromethylaniline.Mixture is through gas chromatographic analysis, and the content of each isomer is: 92% o-tri uoromethyl aniline, and 5.5% m-tri uoromethyl
aniline, 0.7% is p-tri uoromethylaniline, 0.9% is dechlorination product not.
The principal reaction condition is to the quantized data table of reaction in uence in table 3 catalytic hydrogenation-hydrogenolysis dechlorination reaction
Patent Citations (2)
Publication number Priority date Publication date Assignee Title
US4387246A * 1980-12-12 1983-06-07 Rhone-Poulenc Industries Method of preparing orthotri uoromethyl aniline
US4469890A * 1983-09-07 1984-09-04 Monsanto Company Preparation of ortho-aminobenzotri uoride
Family To Family Citations Granted Patent
* Cited by examiner, † Cited by third party
Cited By (4)
Publication number Priority date Publication date Assignee Title
Family To Family Citations
CN100368378C * 2006-05-15 2008-02-13 南通市东昌化工有限公司 Production process of o-tri uoromethyl aniline
CN101182295B * 2007-12-14 2010-09-01 浙江工业大学 Method for synthesizing 2-amido-5-chlorobenzotri uoride
CN101538206B * 2009-04-27 2012-07-25 浙江工业大学 Method for processing and utilizing tri uoromethyl aniline distillation still
residue
CN103880686B * 2014-02-21 2015-03-25 江苏丰华化学工业有限公 Method for recycling wastes of tri uoromethyl phenylamine kettle residue
司
* Cited by examiner, † Cited by third party, ‡ Family to family citation
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Priority And Related Applications Granted Patent
Priority Applications (1)
Application Priority date Filing date Title
CNB2004100169586A 2004-03-12 2004-03-12 Process for preparing o-tri uoromethyl aniline
Applications Claiming Priority (1)
Application Filing date Title
CNB2004100169586A 2004-03-12 Process for preparing o-tri uoromethyl aniline
Legal Events
Date Code Title Description
2005-09-14 C06 Publication
2005-09-14 PB01 Publication
2007-03-07 C10 Entry into substantive examination
2007-03-07 SE01 Entry into force of request for substantive examination
2008-02-27 GR01 Patent grant
2008-02-27 C14 Grant of patent or utility model
2020-12-04 CP03 "change of name, title or address" Address after: 322109, No. 128, industrial road, Weishan Town, Jinhua, Zhejiang, Dongyang
Patentee after: Zhejiang Weihua Chemical Co.,Ltd.
Address before: 322109 Zhejiang city of Dongyang province Weishan Town Weihua
Chemical Co. Ltd.
Patentee before: ZHEJIANG PROVINCE DONGYANG CITY WEIHUA CHEMICAL Co.,Ltd.

Granted Patent
2020-12-04 TR01 Transfer of patent right Effective date of registration: 20201123
Address after: 312369 No.8, Beitang East Road, Shangyu economic and Technological
Development Zone, Hangzhou Bay, Shaoxing City, Zhejiang Province
Patentee after: Wei Zhejiang Huaxin materials Limited by Share Ltd.
Address before: 322109, No. 128, industrial road, Weishan Town, Jinhua, Zhejiang,
Dongyang
Patentee before: Zhejiang Weihua Chemical Co.,Ltd.
Concepts
machine-extracted Download Filter table
Name Image Sections Count Query match
2-(tri uoromethyl)aniline title,claims,abstract,description 35 0.000

F
NH2
manufacturing process title,abstract,description 5 0.000
mixtures claims,abstract,description 31 0.000
dechlorination reactions claims,abstract,description 24 0.000
hydrogenolysis reactions claims,abstract,description 20 0.000
Tri uorotoluene claims,abstract,description 10 0.000

F
4-chloro-1-nitro-2-(tri uoromethyl)benzene F F
claims,abstract,description 9 0.000
Granted Patent
Cl F
O
+
N
-
O
chlorination reactions claims,abstract,description 8 0.000
raw materials claims,abstract,description 8 0.000
ring formation reactions claims,abstract,description 3 0.000
chemical reactions claims,description 61 0.000
preparation methods claims,description 16 0.000
nitration reactions claims,description 15 0.000
powders claims,description 13 0.000
catalysts claims,description 10 0.000
catalytic claims,description 10 0.000
palladium claims,description 10 0.000
magnesium claims,description 9 0.000
Mg
products claims,description 8 0.000
acids claims,description 7 0.000
binding agents claims,description 7 0.000
chlorine claims,description Granted

7 Patent 0.000
methanol claims,description 7 0.000
OH
chlorine claims,description 6 0.000
distillation claims,description 6 0.000
solvents claims,description 6 0.000
Iron(III) chloride claims,description 5 0.000

Cl
Fe
Cl Cl
chlorine atom claims,description 5 0.000
Cl
3-(Tri uoromethyl)aniline claims,description 4 0.000
H2N F
hydrogen claims,description 4 0.000
iron claims,description 4 0.000

Granted Patent
methanol claims,description 4 0.000
methods claims,description 4 0.000
nitroso nitrate claims,description 4 0.000

O-
O
N+ O
N
oils claims,description 4 0.000
H H
Fe
palladium claims,description 3 0.000
corresponding claims,description 2 0.000

engineering processes abstract,description 9 0.000
catalytic hydrogenation reactions abstract,description 3 0.000
effects abstract,description 2 0.000
favourable abstract 1 0.000
Show all concepts from the description section
Granted Patent
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26/12/2020 CN100371313C - Process for preparing o-trifluoromethyl aniline - Google Patents

Process for preparing o-tri uoromethyl aniline

Application CNB2004100169586A events

2004-03-12 Application led by 浙江省东阳市巍华化工有限

2004-03-12 Priority to CNB2004100169586A

2005-09-14 Publication of CN1666974A

2008-02-27 Application granted

2008-02-27 Publication of CN100371313C

Info: Patent citations (2), Cited by (4), Legal events, Similar

External links: Espacenet, Global Dossier, Discuss

Claims (7) Hide Dependent

The preparation method of o-tri uoromethyl aniline

Summary of the invention

The ring chlorination reaction:

Embodiment 2-5 is with embodiment 1.

Embodiment 2-5 is with embodiment 1.

Catalytic hydrogenation-hydrogenolysis dechlorination reaction:

Embodiment 2-9 is with embodiment 1.

Patent Citations (2)

Publication number Priority date Publication date Assignee Title

US4469890A * 1983-09-07 1984-09-04 Monsanto Company Preparation of ortho-aminobenzotri uoride

Family To Family Citations Granted Patent

* Cited by examiner, † Cited by third party

Publication number Priority date Publication date Assignee Title

Family To Family Citations

CN100368378C * 2006-05-15 2008-02-13 南通市东昌化工有限公司 Production process of o-tri uoromethyl aniline

CN101182295B * 2007-12-14 2010-09-01 浙江工业大学 Method for synthesizing 2-amido-5-chlorobenzotri uoride

* Cited by examiner, † Cited by third party, ‡ Family to family citation

Publication Publication Date Title

KR100567039B1 2006-04-04 Process for preparation of formate esters

CN100480231C 2009-04-22 Process for preparing phenethylamine derivatives

US20070238901A1 2007-10-11 Process for preparing aniline Granted Patent

SK145293A3 1994-07-06 Method of preparation 4-aminodiphenylamine

CN102439062B 2013-07-03 Method for producing aliphatic polycarbonate

US6881864B2 2005-04-19 Production method of xylylenediamine

CN102070448B 2013-04-03 Method for preparing dimethyl succinate

CN101903366B 2012-09-05 Method for producing cis-rose oxide

CN101228102A 2008-07-23 (alkylphenyl)alkylcyclohexane and method for producing (alkylphenyl)alkylcyclohexane or alkylbiphenyl

CA2348893A1 2000-06-08 Process for preparing cross-bridged tetraaza macrocycles

US6140538A 2000-10-31 Process for preparing 4-aminodiphenylamines

CN101622223A 2010-01-06 Method for producing ethyleneamines

CN101691332B 2014-06-11 Method for preparing 4-amino diphenylamine by catalytic hydrogenation

TWI221833B 2004-10-11 E cient enantioselective addition reaction using organozinc reagent

KR100621310B1 2006-09-06 Method for preparing 4-aminodiphenylamine

JP4546958B2 2010-09-22 Method for producing 4-aminodiphenylamine

Priority And Related Applications Granted Patent

Priority Applications (1)

Application Priority date Filing date Title

CNB2004100169586A 2004-03-12 2004-03-12 Process for preparing o-tri uoromethyl aniline

Applications Claiming Priority (1)

Application Filing date Title

CNB2004100169586A 2004-03-12 Process for preparing o-tri uoromethyl aniline

Date Code Title Description

2005-09-14 C06 Publication

2005-09-14 PB01 Publication

2007-03-07 C10 Entry into substantive examination

2007-03-07 SE01 Entry into force of request for substantive examination

2008-02-27 GR01 Patent grant

2008-02-27 C14 Grant of patent or utility model

Patentee after: Zhejiang Weihua Chemical Co.,Ltd.

Patentee before: ZHEJIANG PROVINCE DONGYANG CITY WEIHUA CHEMICAL Co.,Ltd.

2020-12-04 TR01 Transfer of patent right Effective date of registration: 20201123

Patentee after: Wei Zhejiang Huaxin materials Limited by Share Ltd.