CN109627194A - A method of the synthesis chloro- toluenesulfonic acid of 2- amino -5- - Google Patents
A method of the synthesis chloro- toluenesulfonic acid of 2- amino -5- Download PDFInfo
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- CN109627194A CN109627194A CN201811627488.5A CN201811627488A CN109627194A CN 109627194 A CN109627194 A CN 109627194A CN 201811627488 A CN201811627488 A CN 201811627488A CN 109627194 A CN109627194 A CN 109627194A
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- chloro
- toluenesulfonic acid
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- amino
- nitro
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of methods for synthesizing the chloro- toluenesulfonic acid of 2- amino -5-, it is characterized by: the chloro- toluenesulfonic acid of reactant 2- nitro -5- is in gas phase, -- hydrogen gas, liquid -- solvent and solid phase -- catalytic hydrogenation reaction generation in Raney nickel three-phase system, the specific method is as follows: by mass percentage throwing into following ingredients in reaction kettle: the chloro- toluenesulfonic acid 15-20% of 2- nitro -5-;Catalyst 8-10%, dechlorination inhibitor 0.2-0.4%, solvent 70-76%；Starting stirring, and constantly high-purity hydrogen is passed through to reaction kettle, it is ensured that reacting kettle inner pressure is constant；Reaction temperature control is 75-85 DEG C;Pressure 2.5-3.5MPa;Speed of agitator 300-450rpm;Reaction time is 30-50min.Process flow simplifies, and the reaction time is short, and product yield improves, and production cost can be greatly reduced, and improves product quality, reduces " three wastes " discharge.
Description
Technical field
The invention belongs to chemical field more particularly to a kind of methods for synthesizing the chloro- toluenesulfonic acid of 2- amino -5-.
Background technique
The chloro- toluenesulfonic acid of 2- amino -5- (CLT acid) is a kind of important organic red pigment intermediate, can synthetic plastic
The color lakes organic pigments such as the red 36b of bright red, new treasured, bronze red c.The pigment is widely used in paint, coating, colored ink, rubber
With coloring plastic etc..CLT acid is one of the organic intermediate that annual consumption crosses ten thousand tons in the world.The most common synthesis side of CLT acid
Method is mainly traditional iron powder reducing method.
This method method has simple process, maturation, also can effectively avoid the generation of dechlorination side reaction, low for equipment requirements,
The advantages that enforceability is good, synthesis under normal pressure, but because lock out operation trouble, control point are more, the quality of product is unstable in production process
Fixed, difference is very big between batch, and iron ion has an impact the use of product in product, and the synthesis yield of product is low, the three wastes
Amount is big, which is unable to satisfy mass production and quantity-produced needs, is only applicable in the interruption autoclave production of batch.
Summary of the invention
It is an object of the invention to avoid the deficiencies in the prior art, a kind of synthesis 2- amino -5- chloro- toluenesulfonic acid is provided
Method.
To achieve the above object, the technical solution adopted by the present invention is that: a kind of synthesis 2- amino -5- chloro- toluenesulfonic acid
Method, it is characterised in that: the chloro- toluenesulfonic acid of reactant 2- nitro -5- is in gas phase -- hydrogen gas, liquid -- solvent and solid phase -- nickel
Catalytic hydrogenation reaction generates in catalyst three-phase system, and the specific method is as follows: by mass percentage throwing into following ingredients instead
It answers in kettle: the chloro- toluenesulfonic acid 15-20% of 2- nitro -5-;Catalyst 8-10%, dechlorination inhibitor 0.2-0.4%, solvent 70-76%；
Starting stirring, and 99.99% high-purity hydrogen is constantly passed through to reaction kettle, it is ensured that reacting kettle inner pressure is constant；Reaction temperature control
It is 75-85 DEG C;Pressure 2.5-3.5MPa;Speed of agitator 300-450rpm;Reaction time is 30-50min, and reaction terminates to obtain 2-
The chloro- toluenesulfonic acid product of amino -5-.
The Raney nickel is nickel-loaded or skeleton nickel.
The solvent is any one of methanol, ethyl alcohol, toluene, water.
The invention has the following advantages that process flow simplifies, the reaction time is short, and product yield improves, can be significantly
Production cost is reduced, product quality is improved, " three wastes " discharge is reduced, reaches clean manufacturing, energy-saving and emission-reduction, finally realize zero-emission
Production requirement；Good basic condition is created for the production upgrading of enterprise's downstream deep processed product.
Specific embodiment
The principles and features of the present invention are described below, and the given examples are served only to explain the present invention, is not intended to limit
Determine the scope of the present invention.
Embodiment 1:
Successively by 145 grams of the chloro- toluenesulfonic acid of 2- nitro -5-, 75.6 grams of skeleton nickel, 660 grams of methanol, 1.89 grams of dechlorination inhibitor
It puts into 1.5L autoclave (selecting self-priming stirring), packing factor 63%；Speed of agitator 350rpm；Reaction temperature 80
℃；Reaction pressure 2.5MPa；Mature reaction time 30min.Reaction process is constantly passed through 99.99% high-purity hydrogen to reaction kettle,
Ensure that reacting kettle inner pressure is constant.After measured, product yield reaches 93.5%.
Embodiment 2:
Successively by 148 grams of the chloro- toluenesulfonic acid of 2- nitro -5-, 75.6 grams of nickel-loaded, 660 grams of methanol, 1.89 grams of dechlorination inhibitor
It puts into 1.5L autoclave (selecting self-priming stirring), packing factor 63%；Speed of agitator 350rpm；Reaction temperature 80
℃；Reaction pressure 2.5MPa；Mature reaction time 30min.Reaction process is constantly passed through 99.99% high-purity hydrogen to reaction kettle,
Ensure that reacting kettle inner pressure is constant.After measured, product yield reaches 93.8%.
Claims (3)
1. a kind of method for synthesizing the chloro- toluenesulfonic acid of 2- amino -5-, it is characterised in that: the chloro- methylbenzene of reactant 2- nitro -5-
Sulfonic acid is in gas phase -- hydrogen gas, liquid -- solvent and solid phase -- catalytic hydrogenation reaction generation in Raney nickel three-phase system, it is specific square
Method is as follows:
Following ingredients are thrown into reaction kettle by mass percentage: the chloro- toluenesulfonic acid 15-20% of 2- nitro -5-;Catalyst 8-
10%, dechlorination inhibitor 0.2-0.4%, solvent 70-76%；Starting stirring, and constantly high-purity hydrogen is passed through to reaction kettle, it is ensured that it is anti-
Answer pressure in kettle constant；Reaction temperature control is 75-85 DEG C;Pressure 2.5-3.5MPa;Speed of agitator 300-450rpm;When reaction
Between be 30-50min, reaction terminate obtain the chloro- toluenesulfonic acid product of 2- amino -5-.
2. a kind of method for synthesizing the chloro- toluenesulfonic acid of 2- amino -5- according to claim 1, it is characterised in that: the nickel
Catalyst is nickel-loaded or skeleton nickel.
3. a kind of method for synthesizing the chloro- toluenesulfonic acid of 2- amino -5- according to claim 1, it is characterised in that: described molten
Agent is any one of methanol, ethyl alcohol, toluene, water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811627488.5A CN109627194A (en) | 2018-12-28 | 2018-12-28 | A method of the synthesis chloro- toluenesulfonic acid of 2- amino -5- |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811627488.5A CN109627194A (en) | 2018-12-28 | 2018-12-28 | A method of the synthesis chloro- toluenesulfonic acid of 2- amino -5- |
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| CN109627194A true CN109627194A (en) | 2019-04-16 |
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| CN201811627488.5A Pending CN109627194A (en) | 2018-12-28 | 2018-12-28 | A method of the synthesis chloro- toluenesulfonic acid of 2- amino -5- |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5721362A (en) * | 1980-07-11 | 1982-02-04 | Dainippon Ink & Chem Inc | Production of c-acid or its salt |
| CN101735073A (en) * | 2008-11-25 | 2010-06-16 | 南京理工大学 | Method for preparing chloroaniline by catalysis hydrogenation |
| CN101774930A (en) * | 2010-02-10 | 2010-07-14 | 江苏康恒化工有限公司 | Method for preparing m-chloro aniline |
| CN102050746A (en) * | 2009-10-28 | 2011-05-11 | 中国石油化工集团公司 | Method for preparing o-chloroaniline |
| CN102757352A (en) * | 2012-05-24 | 2012-10-31 | 江苏康恒化工有限公司 | Production process for preparing parachloroaniline by catalytic hydrogenation of para-nitrochlorobenzene |
| CN102964278A (en) * | 2012-11-27 | 2013-03-13 | 浙江秦燕化工有限公司 | Method for preparing CLT acid (2-amino-4-methyl-5-chlorobenzene sulfonic acid) by continuous catalytic hydrogenation reduction |
| CN104402774A (en) * | 2014-11-21 | 2015-03-11 | 浙江秦燕化工有限公司 | Method for preparing CLT acid through continuous catalytic hydrogenation reduction |
-
2018
- 2018-12-28 CN CN201811627488.5A patent/CN109627194A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5721362A (en) * | 1980-07-11 | 1982-02-04 | Dainippon Ink & Chem Inc | Production of c-acid or its salt |
| CN101735073A (en) * | 2008-11-25 | 2010-06-16 | 南京理工大学 | Method for preparing chloroaniline by catalysis hydrogenation |
| CN102050746A (en) * | 2009-10-28 | 2011-05-11 | 中国石油化工集团公司 | Method for preparing o-chloroaniline |
| CN101774930A (en) * | 2010-02-10 | 2010-07-14 | 江苏康恒化工有限公司 | Method for preparing m-chloro aniline |
| CN102757352A (en) * | 2012-05-24 | 2012-10-31 | 江苏康恒化工有限公司 | Production process for preparing parachloroaniline by catalytic hydrogenation of para-nitrochlorobenzene |
| CN102964278A (en) * | 2012-11-27 | 2013-03-13 | 浙江秦燕化工有限公司 | Method for preparing CLT acid (2-amino-4-methyl-5-chlorobenzene sulfonic acid) by continuous catalytic hydrogenation reduction |
| CN104402774A (en) * | 2014-11-21 | 2015-03-11 | 浙江秦燕化工有限公司 | Method for preparing CLT acid through continuous catalytic hydrogenation reduction |
Non-Patent Citations (1)
| Title |
|---|
| 郑建慧: "CLT酸绿色合成工艺的研究", 《中国优秀硕士论文全文数据库 工程科技I辑》 * |
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Application publication date: 20190416 |