CN106045868A - Method for producing dimethyl aminoterephthalate through catalytic hydrogenation - Google Patents
Method for producing dimethyl aminoterephthalate through catalytic hydrogenation Download PDFInfo
- Publication number
- CN106045868A CN106045868A CN201610401448.3A CN201610401448A CN106045868A CN 106045868 A CN106045868 A CN 106045868A CN 201610401448 A CN201610401448 A CN 201610401448A CN 106045868 A CN106045868 A CN 106045868A
- Authority
- CN
- China
- Prior art keywords
- dmt
- dimethyl terephthalate
- catalyst
- production method
- nitroterephthalic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for producing dimethyl aminoterephthalate through catalytic hydrogenation. Dimethyl nitroterephthalate is dissolved in isopropanol, the materials are added to a hydrogenation kettle, a catalyst is added, hydrogen is introduced, and dimethyl aminoterephthalate is obtained through cooling, centrifugation and drying after hydrogenation. The raw material conversion rate reaches 100%, the product is white powder, the chromatographic purity is 99% or higher, and the yield can be 95% or higher.
Description
Technical field
The invention belongs to catalytic hydrogenation production field, particularly disclose a kind of 2-nitroterephthalic's dimethyl ester hydrogenation
Prepare the production method of 2-amino dimethyl terephthalate (DMT).
Background technology
2-amino dimethyl terephthalate (DMT) is a kind of important industrial chemicals, for medicine and dyestuff, motion-picture color glue
Sheet intermediate.2-amino dimethyl terephthalate (DMT) is to be obtained through reduction by 2-nitroterephthalic's dimethyl ester.It is conventional raw
Production. art has iron powder reducing method, sodium sulfide reducing method and catalytic hydrogenation method.Although iron powder reducing method technology maturation, raw material is easy to get,
Technique is simple, but labour protection condition is poor, and the environmental pollution that iron cement causes is serious.Sodium sulfide reducing method is also a kind of relatively conventional
Reducing process, this technological reaction mild condition, it is easy to control, but relatively costly, wastewater flow rate is big, and damage ratio is more serious.At 2-ammonia
In the kinds of processes route of base dimethyl terephthalate (DMT), catalytic hydrogenation process owing to process is simple, advantages of environment protection and
Receive much concern, be a green production technology.This technique is to use catalytic hydrogenation.
Summary of the invention
The present invention is directed to deficiency present in existing production technology, with isopropanol as solvent, 2-nitroterephthalic two
Methyl ester catalyst under, react with hydrogen under 80-100 DEG C and 0.3-2.5MPa, after completing, catalyst leached, fall
Temperature crystallization, filtration drying obtains 2-amino dimethyl terephthalate (DMT).Wherein said catalyst is the precious metal catalyst of independent research
Agent, the consumption of catalyst is the 0.05%-20% of raw material 2-nitroterephthalic's dimethyl ester quality；Gained 2-amino is to benzene
Dicarboxylic acid dimethyl ester chromatographic purity more than 99.5%.
2-nitroterephthalic's dimethyl ester Hydrogenation described in the present invention is for the side of 2-amino dimethyl terephthalate (DMT)
Method, its feature include following some:
(1) reaction is reacted in the presence of an organic, and the kind of organic solvent is isopropanol；
(2) used catalyst is the noble metal catalyst of independent research, reusable edible, low interpolation, and height is applied mechanically, low cost
；
(3) reaction condition is gentle, temperature 80-100 DEG C, and pressure about 0.3-2.5MPA can complete reaction；
(4) reaction yield is high, low cost, and no waste discharge alleviates ambient pressure.
Detailed description of the invention:
Below by specific embodiment, the present invention will be further elaborated, it should be appreciated that, the description below be only for
The explanation present invention, does not limit its content.
Following embodiment, as a example by our company's laboratory equlpment, elaborates the technical process of the present invention, used mainly
Raw material is: 2-nitroterephthalic's dimethyl ester (technical grade, 99%), hydrogen (technical grade, 99.9%), isopropanol (industry
Level 99%), noble metal catalyst (is made by oneself), and capital equipment used is: reduction kettle (2m), measuring tank (2m), filter
(accurate).
Embodiment 1
As a example by 200 kilograms of 2-nitroterephthalic's dimethyl esters, used catalyst is self-control catalyst, uses in production process
The total amount of catalyst is 0.1-3%(0.2-6 kilogram of raw material), isopropanol total amount is 8 times (1600 kilograms) of raw material, in hydrogenation
Before, the order that 2-nitroterephthalic's dimethyl ester, isopropanol and catalyst put into still is as follows:
1,2-nitroterephthalic's dimethyl ester 200 kilograms, 1600 kilograms of addition reactors of isopropanol, gas displacement.
2, being passed through hydrogen, hydrogenation starts, and controlling reaction temperature is 80 ± 5 DEG C, and control reaction pressure is 0.3-1.0
Mpa。
3, reaction terminates filtering catalyst, and filtrate is cooled to 20 degrees Celsius of crystallization below, filtration drying, obtains finished product 2-ammonia
Base dimethyl terephthalate (DMT).
4, the product prepared according to the method described above is analyzed, and the conversion ratio of 2-nitroterephthalic's dimethyl ester is
The selectivity of 100%, 2-amino dimethyl terephthalate (DMT) is 99.6%, and 2-amino dimethyl terephthalate (DMT) content is 99.9%,
Yield is 96.5%.
Embodiment 2:
Produce as a example by 2-amino dimethyl terephthalate (DMT) by 200 kilograms of 2-nitroterephthalic's dimethyl esters, in production process
The catalyst used is noble metal catalyst (making by oneself), and consumption is that the 0.1-3%(0.2-6 of 2-nitroterephthalic's dimethyl ester is public
Jin), isopropanol total amount is 8 times (1600 kilograms) of raw material, when producing continuously, 2-nitroterephthalic's dimethyl ester, isopropyl
Alcohol and catalyst are to add according to the order of (), for investigating the stability of technique, are carried out continuously five experiments, and its result is table
1 is as follows:
Reaction condition: temperature 80 ± 5 DEG C, pressure 0.3-1.0Mpa, ph7-8.
Finding out from table, 2-nitroterephthalic's dimethyl ester conversion ratio is 100%, 2-amino dimethyl terephthalate (DMT)
Selectivity more than 99.5%, finished product content is more than 99.7%, and yield is more than 97%.
Embodiment 3:
Produce as a example by 2-amino dimethyl terephthalate (DMT) by 200 kilograms of 2-nitroterephthalic's dimethyl esters, in production process
Use catalyst is noble metal catalyst, and consumption is 0.1-3%(0.2-6 kilogram of 2-nitroterephthalic's dimethyl ester), isopropyl
Alcohol total amount is 8 times (1600 kilograms) of raw material, when producing continuously, reacts according to the production technology of embodiment 1, different
Be that catalyst is circulated and applies mechanically.The reaction of each still terminates, and after the complete catalyst of filter pressing, enters in reactor by catalyst blowback,
Add the catalyst of 0.1-0.5 kilogram, through the recycled of row catalyst.After catalyst starts to apply mechanically, the addition of raw catelyst
Amount is greatly reduced, the most original 5%-25%, greatly reduces cost, and through a large amount of productive experiments, this catalyst can be applied mechanically continuously
More than ten times.
In order to reduce catalyst amount, cost-effective, now having carried out catalyst according to the method for embodiment 2 applies mechanically experiment,
Every time add that the amount of raw catelyst is the 0.1%(the most original catalyst usage amount of nitro compounds 10%), apply mechanically five times continuously, result
It is shown in Table 2.
Reaction condition: temperature 80 ± 5 DEG C, pressure 0.3-0.6Mpa, ph7-8.
Finding out from table, 2-nitroterephthalic's dimethyl ester conversion ratio is 100%, 2-amino dimethyl terephthalate (DMT)
Selectivity more than 99.5%, finished product content is more than 99.7%, and yield is more than 97%, basically identical with the result do not applied mechanically,
But the consumption of catalyst and production cost can significantly decline.
Execute example 4:
As a example by 200 kilograms of 2-amino dimethyl terephthalate (DMT)s, used catalyst is noble metal catalyst, makes in production process
It is 0.1-3%(0.2-6 kilogram of raw material by the total amount of catalyst), isopropanol total amount is 8 times (1600 kilograms) of raw material, at hydrogen
Before change, the order that 2-nitroterephthalic's dimethyl ester, isopropanol and catalyst put into still is as follows:
1,2-nitroterephthalic's dimethyl ester 200 kilograms, 1600 kilograms of addition reactors of isopropanol, gas displacement.
2, being passed through hydrogen, hydrogenation starts, and controlling reaction temperature is 80 ± 5 DEG C, and control reaction pressure is 0.3-
1.0Mpa。
3, reaction terminates, and catalyst is recovered by filtration, and the catalyst of recovery recycles.
4, filtrate passes through decrease temperature crystalline, and filtration drying obtains finished product 2-amino dimethyl terephthalate (DMT).
5, the filtrate that crystallization and filtration goes out, through decompression distillation and concentration, separates out crystallization further, adds inorganic before it is concentrated
Class antioxidant, to prevent the 2-amino dimethyl terephthalate (DMT) in solution from aoxidizing.The isopropanol concentrated is different with distill out
Propanol, adds hydriding reactor, is circulated and applies mechanically, it is to avoid environmental pollution and the wasting of resources.
6, the product prepared according to the method described above is analyzed, and the conversion ratio of 2-nitroterephthalic's dimethyl ester is
The selectivity of 100%, 2-amino dimethyl terephthalate (DMT) is 99.6%, and 2-amino dimethyl terephthalate (DMT) content is 99.9%,
Yield is 96.5%.
Along with repeating of above-mentioned production stage, catalyst and water carry out the substantial amounts of work applied mechanically and reuse
Make, it is to avoid environmental pollution and the wasting of resources.
Claims (7)
1. catalytic hydrogenation produces a production method for 2-amino dimethyl terephthalate (DMT), with 2-nitroterephthalic two
Methyl ester is raw material, it is characterised in that: 2-nitroterephthalic's dimethyl ester in the presence of a catalyst, at 80-100 DEG C and 0.3-
Reacting with hydrogen under 2.5MPa, with isopropanol as solvent, after completing, decrease temperature crystalline obtains 2,4-dichloro-5-isopropoxy aniline.
2. the production method of 2-amino dimethyl terephthalate (DMT) as claimed in claim 1, it is characterised in that: described catalysis
Agent is the noble metal catalyst of independent research, and the consumption of catalyst is raw material 2-nitroterephthalic's dimethyl ester quality
0.05%-20%.
3. the production method of the 2-amino dimethyl terephthalate (DMT) as described in claim 1, it is characterised in that: reaction temperature
It it is 80 DEG C-100 DEG C.
4. the production method of the 2-amino dimethyl terephthalate (DMT) as described in claim 1, it is characterised in that: reaction pressure
For 0.3-2.5MPa.
5. the production method of the 2-amino dimethyl terephthalate (DMT) as described in claim 1-4, it is characterised in that: 2-nitro
Dimethyl terephthalate (DMT), hydrogen, catalyst enter reactor, are with isopropanol as solvent reaction.
6. the production method of the 2-amino dimethyl terephthalate (DMT) as described in claim 1-5, it is characterised in that: gained 2-
Amino dimethyl terephthalate (DMT) chromatographic purity more than 99.5%.
7. the production method of the 2-amino dimethyl terephthalate (DMT) as described in claim 1-5, it is characterised in that: gained
2-amino dimethyl terephthalate (DMT) chromatographic purity more than 99%, conversion ratio 100%, yield more than 95%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610401448.3A CN106045868A (en) | 2016-06-10 | 2016-06-10 | Method for producing dimethyl aminoterephthalate through catalytic hydrogenation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610401448.3A CN106045868A (en) | 2016-06-10 | 2016-06-10 | Method for producing dimethyl aminoterephthalate through catalytic hydrogenation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106045868A true CN106045868A (en) | 2016-10-26 |
Family
ID=57171261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610401448.3A Pending CN106045868A (en) | 2016-06-10 | 2016-06-10 | Method for producing dimethyl aminoterephthalate through catalytic hydrogenation |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106045868A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104072403A (en) * | 2014-06-24 | 2014-10-01 | 成都大学 | Method for preparing compound UNC1215 |
-
2016
- 2016-06-10 CN CN201610401448.3A patent/CN106045868A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104072403A (en) * | 2014-06-24 | 2014-10-01 | 成都大学 | Method for preparing compound UNC1215 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108101850B (en) | Method for improving quality of 5-acetoacetylaminobenzimidazolone | |
| CN110105220B (en) | Method for preparing m-phenylenediamine from meta-oil | |
| CN107746380B (en) | Industrial production method of 2-amino-4-acetamino anisole | |
| CN113429295A (en) | Method for preparing m-phenylenediamine by continuous catalytic hydrogenation based on fixed bed microreactor | |
| CN104529794B (en) | The preparation method of Boscalid intermediate 2-(4-chlorphenyl) aniline | |
| CN104447366A (en) | Preparation method of high-purity 2-amino-3, 5-dibromobenzaldehyde | |
| CN103508967A (en) | Preparation method of benzotriazole ultraviolet absorbent UV-P | |
| CN106045868A (en) | Method for producing dimethyl aminoterephthalate through catalytic hydrogenation | |
| CN106995382A (en) | A kind of method of catalytic hydrogenation production 3- methyl-PABA | |
| CN109180501B (en) | Synthetic method of 4, 4' -diaminodiphenyl ether | |
| CN106995392A (en) | A kind of method of catalytic hydrogenation production M acid | |
| CN101607917B (en) | Production method of high-quality p-aminophenol | |
| CN109336825A (en) | A method of improving 5-Amino-2-benzimidazolinone quality | |
| CN113149911B (en) | Preparation method of high-purity 5-aminobenzimidazole ketone | |
| CN104926599A (en) | Method for preparing high-purity 4,4'-bis(chloromethyl)-1,1'-biphenyl under novel solvent system | |
| CN112694407A (en) | Production and preparation method of 2-methyl-4-isopropyl aniline | |
| CN111004141B (en) | New method for synthesizing nintedanib intermediate 2-chloro-N-methyl-N- (4-nitrophenyl) acetamide | |
| CN110590585B (en) | Process for preparing benzocaine by solvent-free hydrogenation | |
| CN109761841B (en) | Preparation process of spectrum-grade formamide | |
| CN109734645B (en) | Synthetic process of isatin | |
| CN109384654B (en) | Method for producing ethylene glycol mono-tert-butyl ether | |
| CN112939843A (en) | Synthesis method of N-hydroxymethyl-3, 4,5, 6-tetrahydrophthalimide | |
| CN113248355B (en) | Preparation method of p-chlorobenzaldehyde | |
| CN112574007B (en) | Novel cyclohexylimine ionic liquid and method for catalyzing synthesis of butyl citrate and bisphenol F | |
| CN108218712A (en) | A kind of preparation method of meta nitro aniline |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20161026 |