CN102234235A - Synthesis method of 5-chloro-2-methyl aniline - Google Patents
Synthesis method of 5-chloro-2-methyl aniline Download PDFInfo
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- CN102234235A CN102234235A CN2010101545816A CN201010154581A CN102234235A CN 102234235 A CN102234235 A CN 102234235A CN 2010101545816 A CN2010101545816 A CN 2010101545816A CN 201010154581 A CN201010154581 A CN 201010154581A CN 102234235 A CN102234235 A CN 102234235A
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- polysulfide
- aminotoluene
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Abstract
The invention discloses a synthesis method of 5-chloro-2-methyl aniline. The synthesis method comprises the following steps: dissolving a polysulfide in water, stirring, adding an ammonium salt, heating while controlling the temperature at 30-105 DEG C, and dropwisely adding 4-chloro-2-nitro-toluene for reaction; and separating out an organic phase after the reaction is finished, washing with water to be neutral, distilling the organic phase, and collecting fractions at 127-137 DEG C under the vacuum degree of 0.1 MPa to obtain 5-chloro-2-methyl aniline. The synthesis method of 5-chloro-2-methyl aniline disclosed by the invention has the advantages of high product yield, low production cost and high safety.
Description
Technical field
The present invention relates to a kind of synthetic method of 5-chloro-2-aminotoluene.
Background technology
5-chloro-2-aminotoluene is as the developer of cotton, silk and polyamide fabric dyeing and stamp.Be used to make rapidogen dye.Can directly synthesize the red basic KB of glacial dye in the dye industry, azoic coupling component (AS-KB).It still is a kind of important pesticide intermediate.In the prior art, the preparation of 5-chloro-2-aminotoluene mainly is a hydrogenating reduction and getting, and is expressed as follows with chemical equation:
Wherein X is a kind of among Ni, Gr, Pt, Pd, Co, Cr and the Rh.
The shortcoming of this method is that catalyzer is easily poisoned, and activation performance is poor, and yield only can reach 87%, and product cost is relatively also than higher.
Summary of the invention
The synthetic method that the purpose of this invention is to provide low, the safe 5-chloro-2-aminotoluene of a kind of yield height, production cost.
The synthetic method of 5-chloro-2-aminotoluene provided by the present invention comprises the steps:
Polysulfide is soluble in water, stir, add ammonium salt, heat up, temperature is controlled at 30～105 ℃, drips 4-chloro-2-nitrotoluene and reacts;
After reaction is finished, separate organic phase, be washed to neutrality, organic phase is distilled, and vacuum tightness 0.1MPa collects 127～137 ℃ of fractions, obtains 5-chloro-2-aminotoluene.
The synthetic method of 5-chloro-2-aminotoluene of the present invention, wherein: described polysulfide is sodium polysulphide, calcium polysulfide or ammonium polysulfide.
The synthetic method of 5-chloro-2-aminotoluene of the present invention, wherein: described ammonium salt is one or more in ammonium chloride, ammonium sulfate, monoammonium sulfate, ammonium nitrate, volatile salt, bicarbonate of ammonia, Neutral ammonium fluoride, ammonium iodide, the brometo de amonio.
The synthetic method of 5-chloro-2-aminotoluene of the present invention, wherein: the mol ratio of described 4-chloro-2-nitrotoluene, described ammonium salt and described polysulfide is (1～2): (0.4～0.6): (1～2).
The synthetic method of 5-chloro-2-aminotoluene of the present invention, do not use the X catalyst series, safe, production cost is low, product yield height, and help cleaner production control and resource circulation utilization in the commercial run.
Embodiment
Embodiment 1,
In 1000 milliliters the there-necked flask that mechanical stirring, reflux condensing tube, thermometer are housed, the sodium polysulphide of 50ml water and 1mol is added flask, mix objects system and add the 0.4mol brometo de amonio again, progressively drip 1mol 4-chloro-2-nitrotoluene after the intensification, temperature is controlled at 30 ℃, and following chemical reaction takes place system:
After reaction is finished, tell the organic phase on upper strata, be washed to neutrality, organic phase is distilled, and vacuum tightness 0.1MPa collects 127～137 ℃ of fractions, 139.8 grams.
With 5-chloro-2-aminotoluene is standard substance, gas chromatographic analysis.Analytical results as shown in Table 1 and Table 2.
Table 1.5-chloro-2-aminotoluene standard stratographic analysis result
| Peak number | Retention time (min) | Peak height |
| 1 | 4.162 | 259.355 |
| 2 | 7.393 | 231.450 |
| 3 | 20.533 | 81989.234 |
| 4 | 23.202 | 210.259 |
Table 2. fraction stratographic analysis result
| Peak number | Retention time (min) | Peak height |
| 1 | 4.143 | 198.537 |
| 2 | 7.345 | 146.002 |
| 3 | 20.347 | 74959.906 |
| 4 | 23.095 | 107.322 |
5-chloro-2-aminotoluene purity is 99.78% in the fraction, calculates yield 98.80% with 4-chloro-2-nitrotoluene.
Embodiment 2,
In 1000 milliliters the there-necked flask that mechanical stirring, reflux condensing tube, thermometer are housed, the sodium polysulphide of 50ml water and 2mol is added flask, mix objects system and add 0.5mol ammonium chloride again, progressively drip 1mol 4-chloro-2-nitrotoluene after the intensification, temperature is controlled at 105 ℃, and following chemical reaction takes place system:
After reaction is finished, tell the organic phase on upper strata, be washed to neutrality, organic phase is distilled, and vacuum tightness 0.1MPa collects 127～137 ℃ of fractions, 140 grams.
With 5-chloro-2-aminotoluene is standard substance, gas chromatographic analysis.Analytical results is shown in table 3 and table 4.
Table 3.5-chloro-2-aminotoluene standard stratographic analysis result
| Peak number | Retention time (min) | Peak height |
| 1 | 4.162 | 259.355 |
| 2 | 7.393 | 231.450 |
| 3 | 20.533 | 81989.234 |
| 4 | 23.202 | 210.259 |
Table 4. fraction stratographic analysis result
| Peak number | Retention time (min) | Peak height |
| 1 | 4.192 | 196.464 |
| 2 | 7.360 | 147.445 |
| 3 | 20.498 | 74979.356 |
| 4 | 23.124 | 105.250 |
5-chloro-2-aminotoluene purity is 99.78% in the fraction, calculates yield 98.94% with 4-chloro-2-nitrotoluene.
Embodiment 3,
In 1000 milliliters the there-necked flask that mechanical stirring, reflux condensing tube, thermometer are housed, the sodium polysulphide of 50ml water and 1mol is added flask, mix objects system and add the 0.6mol monoammonium sulfate again, progressively drip 2mol 4-chloro-2-nitrotoluene after the intensification, temperature is controlled at 60 ℃, and following chemical reaction takes place system:
After reaction is finished, tell the organic phase on upper strata, be washed to neutrality, organic phase is distilled, and vacuum tightness 0.1MPa collects 127～137 ℃ of fractions, 281.5 grams.
With 5-chloro-2-aminotoluene is standard substance, gas chromatographic analysis.Analytical results is shown in table 5 and table 6.
Table 5.5-chloro-2-aminotoluene standard stratographic analysis result
| Peak number | Retention time (min) | Peak height |
| 1 | 4.162 | 259.355 |
| 2 | 7.393 | 231.450 |
| 3 | 20.533 | 81989.234 |
| 4 | 23.202 | 210.259 |
Table 6. fraction stratographic analysis result
| Peak number | Retention time (min) | Peak height |
| 1 | 4.203 | 189.452 |
| 2 | 7.440 | 142.748 |
| 3 | 20.687 | 74988.240 |
| 4 | 23.256 | 103.001 |
5-chloro-2-aminotoluene purity is 99.78% in the fraction, calculates yield 98.47% with 4-chloro-2-nitrotoluene.
Above embodiment is described preferred implementation of the present invention; be not that scope of the present invention is limited; design under the prerequisite of spirit not breaking away from the present invention; various distortion and improvement that the common engineering technical personnel in this area make technical scheme of the present invention all should fall in the definite protection domain of claims of the present invention.
Claims (4)
1. the synthetic method of a 5-chloro-2-aminotoluene comprises the steps:
Polysulfide is soluble in water, stir, add ammonium salt, heat up, temperature is controlled at 30～105 ℃, drips 4-chloro-2-nitrotoluene and reacts;
After reaction is finished, separate organic phase, be washed to neutrality, organic phase is distilled, and vacuum tightness 0.1MPa collects 127～137 ℃ of fractions, obtains 5-chloro-2-aminotoluene.
2. synthetic method according to claim 1 is characterized in that: described polysulfide is sodium polysulphide, calcium polysulfide or ammonium polysulfide.
3. synthetic method according to claim 1 and 2 is characterized in that: described ammonium salt is one or more in ammonium chloride, ammonium sulfate, monoammonium sulfate, ammonium nitrate, volatile salt, bicarbonate of ammonia, Neutral ammonium fluoride, ammonium iodide, the brometo de amonio.
4. synthetic method according to claim 3 is characterized in that: the mol ratio of described 4-chloro-2-nitrotoluene, described ammonium salt and described polysulfide is (1～2): (0.4～0.6): (1～2).
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| CN2010101545816A CN102234235A (en) | 2010-04-23 | 2010-04-23 | Synthesis method of 5-chloro-2-methyl aniline |
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| CN2010101545816A CN102234235A (en) | 2010-04-23 | 2010-04-23 | Synthesis method of 5-chloro-2-methyl aniline |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804203A (en) * | 2014-02-27 | 2014-05-21 | 江苏省激素研究所股份有限公司 | Synthetic method of 3-chloro-2-methylaniline |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1067370A (en) * | 1992-03-24 | 1992-12-30 | 孙国平 | Noise disease therapeutic appliance with decrease of noise functions |
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2010
- 2010-04-23 CN CN2010101545816A patent/CN102234235A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1067370A (en) * | 1992-03-24 | 1992-12-30 | 孙国平 | Noise disease therapeutic appliance with decrease of noise functions |
Non-Patent Citations (3)
| Title |
|---|
| 张振华: "5_硝基_2_甲氧基苯胺的合成", 《邵阳师范高等专科学校学报》, vol. 21, no. 2, 30 April 1999 (1999-04-30), pages 38 - 39 * |
| 张若蘅 等: "2_4_二硝基苯胺用硫化碱选择还原的研究", 《大连工学院学报》, vol. 24, no. 2, 30 June 1985 (1985-06-30), pages 71 - 75 * |
| 张荣成 等: "芳香族硝基化合物还原制芳胺生产工艺评析", 《IM &P 化工矿物与加工 》, no. 8, 31 August 2000 (2000-08-31), pages 30 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804203A (en) * | 2014-02-27 | 2014-05-21 | 江苏省激素研究所股份有限公司 | Synthetic method of 3-chloro-2-methylaniline |
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Application publication date: 20111109 |