CN105732396A - P-phenylenediamine preparation method - Google Patents
P-phenylenediamine preparation method Download PDFInfo
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- CN105732396A CN105732396A CN201410747577.9A CN201410747577A CN105732396A CN 105732396 A CN105732396 A CN 105732396A CN 201410747577 A CN201410747577 A CN 201410747577A CN 105732396 A CN105732396 A CN 105732396A
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- phenylenediamine
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- propanol
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Abstract
The invention relates to the field of fine chemicals, and specifically relates to a method for preparing p-phenylenediamine. According to the method, palladium on carbon is adopted as a catalyst; 2-methyl-1-propanol, water and acetone are adopted as a mixed solvent; and p-phenylenediamine is prepared through p-nitroanilide catalytic hydrogenation. An alcohol solvent has the problems of high volatilization, high risk and high recovery loss. A water solvent has the problems of low solvent solubility and easy oxidation. With the method, the above problems are solved. The method is safe and environemnt-friendly, and is suitable for industrial production. The p-phenylenediamine provided by the invention has chromatography content higher than 99.9%. An average yield is higher than 99%.
Description
Technical field
The invention belongs to field of fine chemical, be specifically related to a kind of method preparing p-phenylenediamine.
Background technology
P-phenylenediamine (P-Phenylenediamine), it it is one of simplest aromatic diamines, also it is a kind of intermediate being widely used, can be used for producing azo dye, high molecular polymer, it is also possible in producing fur dyeing agent, rubber antioxidant and photo development agent, the production method of traditional p-phenylenediamine has two big classes: one is with paranitroanilinum for raw material, is generated the chemical reduction method of p-phenylenediamine by akali sulphide or iron powder reducing；Two is catalytic hydrogenation method.
In chemical reduction method, the shortcoming vulcanizing alkali process maximum is that waste water is many, containing p-phenylenediamine in waste water, processes costly；Iron powder reducing method produces a large amount of iron cement waste residues, environment is worked the mischief, processes also more difficult.Catalytic hydrogenation method also has two kinds of methods: one is with water for solvent, and the shortcoming of this technique is that product dissolubility in water is little, affects the speed of catalytic reaction, thus reducing the production capacity of equipment, and finished product easily aoxidizes, and outward appearance is affected；Two is with the alcohols of 1-10 carbon atom for solvent, carry out catalytic hydrogenation and prepare p-phenylenediamine, although this technique solves pollution problem and solubility, but owing to the activity of catalyst is higher, alcohols is inflammable thing, uses dangerous, during especially with Raney's nickel, danger is bigger, thus bringing potential safety hazard, loss simultaneously is big, increases the production cost of product.
Summary of the invention
It is an object of the invention to provide a kind of method preparing p-phenylenediamine, overcome simple with water or alcohols for solvent, dissolubility is little, product easily aoxidizes, and the shortcoming that there is potential safety hazard.
The described method preparing p-phenylenediamine, is with palladium carbon for catalyst, and with 2-methyl isophthalic acid-propanol, water, acetone for mixed solvent, paranitroanilinum catalytic hydrogenation prepares p-phenylenediamine.
Wherein, 2-methyl isophthalic acid-propanol, water, acetone volume ratio be 1:1:1.
The mass ratio of mixed solvent and paranitroanilinum is 1-3:1.Mixed solvent consumption is very few, and the concentration of reactant liquor becomes big, the phenomenon such as side reaction and catalyst activity reduction easily occurs, and consumption is too much, and equipment capacity reduces, energy resource consumption is increased, and cost increases.
Catalyst amount is the 0.1-2% of paranitroanilinum quality.Catalyst amount is the 0.1-2% of paranitroanilinum quality.Catalyst amount is very few, and catalytic capability reduces, and the response time extends, and the production cycle is long, and unit interval production capacity reduces；Consumption is too much, and cost dramatically increases.Catalyst is recyclable to be applied mechanically, and repeatable applies mechanically 10-20 time.
The present invention prepares the method for p-phenylenediamine and specifically adds mixed solvent, paranitroanilinum, catalyst in autoclave, seal, air in still is replaced with nitrogen, use hydrogen exchange nitrogen afterwards, open agitating heating, carry out hydrogenation reaction, react when no longer changing to Hydrogen Vapor Pressure and terminate, cooling, replaces hydrogen in still with nitrogen, obtains p-phenylenediamine after recycling design.
Beneficial effects of the present invention is as follows:
The invention solves alcoholic solvent high volatility, dangerous height, reclaim the difficult problem that loss is big, also overcome the deficiency little, oxidizable with water for Solvent Solubility, safety and environmental protection of the present invention simultaneously, be suitable for industrialized production.The p-phenylenediamine that the present invention produces, chromatographic content more than 99.9%, average yield more than 99%.
Detailed description of the invention
Below in conjunction with embodiment, the present invention will be further described.
Embodiment 1:
In 2000ml autoclave, add 241g paranitroanilinum, 100mL2-methyl isophthalic acid-propanol, 100mL water, 100mL acetone, 0.3g palladium-carbon catalyst, after airtight with nitrogen replace, each 5 times of hydrogen exchange, be warming up to 100 DEG C and carry out hydrogenation reaction, pressure reduces follow-up continuous logical hydrogen, until Hydrogen Vapor Pressure no longer declines, reaction terminates, and is down to room temperature, nitrogen is replaced 3 times, reclaim 2-methyl isophthalic acid-propanol, acetone, gas chromatographic analysis content 99.86%, yield 99.51%.
Embodiment 2:
In 2000ml autoclave, add 239g paranitroanilinum, 100mL2-methyl isophthalic acid-propanol, 100mL water, 100mL acetone, 3g Raney's nickel catalyst, after airtight with nitrogen replace, each 5 times of hydrogen exchange, be warming up to 120 DEG C and carry out hydrogenation reaction, pressure reduces follow-up continuous logical hydrogen, reaction, until Hydrogen Vapor Pressure no longer declines, reaction terminates, being down to room temperature, nitrogen is replaced 3 times, reclaims 2-methyl isophthalic acid-propanol, acetone, gas chromatographic analysis content 99.95%, yield 99.15%.
Embodiment 3:
In 2000ml autoclave, add 238g paranitroanilinum, 100mL2-methyl isophthalic acid-propanol, 100mL water, 100mL acetone, 0.3g platinum C catalyst, after airtight with nitrogen replace, each 5 times of hydrogen exchange, be warming up to 80 DEG C and carry out hydrogenation reaction, pressure reduces follow-up continuous logical hydrogen, until Hydrogen Vapor Pressure no longer declines, reaction terminates, and is down to room temperature, nitrogen is replaced 3 times, reclaim 2-methyl isophthalic acid-propanol, acetone, gas chromatographic analysis content 99.97%, yield 99.42%.
Claims (4)
1. the method preparing p-phenylenediamine, it is characterised in that: with palladium carbon for catalyst, with 2-methyl isophthalic acid-propanol, water, acetone for mixed solvent, paranitroanilinum catalytic hydrogenation prepares p-phenylenediamine.
2. the method preparing p-phenylenediamine according to claim 1, it is characterised in that: 2-methyl isophthalic acid-propanol, water, acetone volume ratio be 1:1:1.
3. the method preparing p-phenylenediamine according to claim 1, it is characterised in that: the mass ratio of mixed solvent and paranitroanilinum is 1-3:1.
4. the method preparing p-phenylenediamine according to claim 1, it is characterised in that: catalyst amount is the 0.1-2% of paranitroanilinum quality.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410747577.9A CN105732396A (en) | 2014-12-09 | 2014-12-09 | P-phenylenediamine preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410747577.9A CN105732396A (en) | 2014-12-09 | 2014-12-09 | P-phenylenediamine preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105732396A true CN105732396A (en) | 2016-07-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410747577.9A Withdrawn CN105732396A (en) | 2014-12-09 | 2014-12-09 | P-phenylenediamine preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105732396A (en) |
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2014
- 2014-12-09 CN CN201410747577.9A patent/CN105732396A/en not_active Withdrawn
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20160706 |