CN1080278A - The preparation method of monochloro-o-dimethyl benzene - Google Patents
The preparation method of monochloro-o-dimethyl benzene Download PDFInfo
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- CN1080278A CN1080278A CN 92104637 CN92104637A CN1080278A CN 1080278 A CN1080278 A CN 1080278A CN 92104637 CN92104637 CN 92104637 CN 92104637 A CN92104637 A CN 92104637A CN 1080278 A CN1080278 A CN 1080278A
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- dimethyl benzene
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Abstract
The present invention is the preparation method who is prepared monochloro-o-dimethyl benzene by the o-Xylol direct chloro-substituted.
The present invention is raw material with the o-Xylol, is catalyzer with lewis' acids such as iron trichloride, aluminum chloride, butter of antimony, tin tetrachloride or iodine, iron etc., need not solvent, with the chlorine direct chloro-substituted, obtains the monochloro-o-dimethyl benzene of high yield.
Description
The present invention is the preparation method who is prepared monochloro-o-dimethyl benzene by the o-Xylol direct chloro-substituted.
Monochloro-o-dimethyl benzene is the raw material of monochloro for phthalic anhydride, itself is again sterilant and solvent.Chloro-benzoic anhydride can be used to prepare the aromatic series tetraprotic acid, and the latter is the monomer of polyimide, also can be used as epoxy curing agent simultaneously, and chloro-benzoic anhydride is again the raw material of dyestuff, medicine and flame-retardant plasticizer etc.
The chloro of o-Xylol can be divided into two classes, one class is with the chlorizating agent chlorination beyond the chlorine, this chlorizating agent has Acetyl Chloride 98Min. (J.Chem Soc.Perhin Transaction. II, 357(1976)) and iron trichloride (J Org.Chem, 26 759(1961)) etc.Another kind of is with the chlorine direct chloro-substituted, but report so far mostly carries out in to chlorine inert solvent, and these solvents have tetracol phenixin (Chem Ztg.103 1(1979)), German Patent 2,358,949,
η * 60 2140(1987) and acetic acid (J.Am.Chem Soc 79 4348(1957); J.Chem.Soc.4039(1960)) and Nitromethane 99Min. (J.Am Chem Soc, 86(6) 1055(1964)) etc.And also rare in the past be the research of main purpose to obtain monochloro-o-dimethyl benzene.
The purpose of this invention is to provide a kind of preparation method who prepares monochloro-o-dimethyl benzene, this method is raw material with the o-Xylol, is catalyzer with lewis' acid, iodine or iron, need not solvent, with the chlorine direct chloro-substituted to obtain monochloro-o-dimethyl benzene.
Catalyzer of the present invention has iron trichloride, aluminum chloride, butter of antimony, lewis' acid or iodine, iron etc. such as tin tetrachloride.Catalyst consumption is the 0.001-1% of o-Xylol, temperature of reaction is-and 20-50 ℃, best catalyst levels is 0.01-0.05%, best temperature of reaction is 10-40 ℃.
The preparation process of monochloro-o-dimethyl benzene of the present invention is, earlier o-Xylol is placed container, add catalyzer, chlorine feeds the reaction solution bottom through surge flask, and byproduct of reaction hydrogenchloride water absorbs, control reaction temperature is at-20-50 ℃, reaction 2hr is washed till weakly alkaline with product filtrate with saturated aqueous sodium carbonate, is washed till neutrality with saturated sodium-chloride water solution again, use dried over anhydrous sodium carbonate, promptly get product monochloro-o-dimethyl benzene once through yield more than 70%.
The present invention makes work simplification owing to do not need solvent with the chlorine direct chloro-substituted, monochloro-o-dimethyl benzene yield height, and by product is few, for the o-Xylol that reacts can reclaim use.
Embodiment provided by the invention is as follows:
Embodiment 1
The 130g o-Xylol is placed there-necked flask, add 0.65g(o-Xylol weight 0.5%) FERRIC CHLORIDE ANHYDROUS is catalyzer, chlorine feeds the reaction solution bottom with the speed of 2.5 bubble/seconds through surge flask, byproduct of reaction hydrogenchloride water absorbs, with the ice-water bath control reaction temperature is-20 ℃, and the reaction times is 2hr.Product filtrate is washed till weakly alkaline with saturated aqueous sodium carbonate, be washed till neutrality with saturated sodium-chloride water solution again, use dried over anhydrous sodium carbonate, get the 171g colourless liquid, survey when product proportion is 1.067(25 ℃), inhaling chlorine dose is 98%, gas chromatographic analysis o-Xylol content is 25.5%, monochloro-o-dimethyl benzene content is 70.2%, and many chloro-o-xylenes content is 4.3%.
Embodiment 2
Removing temperature of reaction is 20 ℃, reaction times is outside the 3hr, all the other are all with example 1, get the 171g colourless liquid, survey when product proportion is 1.053(25 ℃), inhaling chlorine dose is 98%, gas chromatographic analysis o-Xylol content is 11%, monochloro-o-dimethyl benzene content is 81.5%, and many chloro-o-xylenes content is 7.5%.
Embodiment 3
Divided by the 0.13g FERRIC CHLORIDE ANHYDROUS is catalyzer (o-Xylol weight 0.1%), temperature of reaction is 30 ℃, reaction times is outside the 3hr, all the other get the 167g colourless liquid all with example 1, survey when product proportion is 1.040(25 ℃), inhaling chlorine dose is 87%, gas chromatographic analysis o-Xylol content is 19.2%, and monochloro-o-dimethyl benzene content is 77.3%, and many chloro-o-xylenes content is 3.5%.
Embodiment 4
The 130g o-Xylol is placed there-necked flask, each add 0.65g(o-Xylol weight 1%) FERRIC CHLORIDE ANHYDROUS and aluminum trichloride (anhydrous) be catalyzer, chlorine feeds the reaction solution bottom with the speed of 2 bubble/seconds through surge flask, byproduct of reaction hydrogenchloride water absorbs, with the ice-water bath control reaction temperature is 30 ℃, and the reaction times is 2hr.With product filtrate with saturated aqueous sodium carbonate to weakly alkaline, be washed till neutrality with saturated sodium-chloride water solution again, use dried over anhydrous sodium carbonate, get the 168g colourless liquid, survey when product proportion is 1.037(25 ℃), inhaling chlorine dose is 88%, gas chromatographic analysis o-Xylol content is 20.4%, monochloro-o-dimethyl benzene content be 75.2%(wherein the 3-chloro-o-xylene be 30.7%, the 4-chloro-o-xylene is 44.5%), many chloro-o-xylenes content is 4.4%.
Embodiment 5
Removing temperature of reaction is 30 ℃, reaction times is 9hr, logical chlorine speed is outside 1 bubble/second, all the other get the 173g colourless liquid all with example 1, survey when product proportion is 1.067(25 ℃), inhaling chlorine dose is 100%, gas chromatographic analysis o-Xylol content is 9.2%, and monochloro-o-dimethyl benzene content is 81.5%, and many chloro-o-xylenes content is 7.5%.
Embodiment 6
With the product rectifying that embodiment 1-5 is obtained, the control reflux ratio is about 1: 6, gets 190-200 ℃ fraction, gets pure monochloro-o-dimethyl benzene.Can also add anhydrous sodium carbonate 1% with the micro-hydrogenchloride that neutralizes in washing back chloro crude product, the fraction of 120-140 ℃/400-500mmHg is got in underpressure distillation, gets pure monochloro-o-dimethyl benzene.
Claims (2)
1, a kind of preparation method of monochloro-o-dimethyl benzene, be that the employing o-Xylol is a raw material, the invention is characterized in lewis' acid, iodine or iron are catalyzer, need not solvent, with the chlorine direct chloro-substituted, catalyst consumption is 0.001～1% of an o-Xylol, best catalyst levels is 0.01-0.05%, temperature of reaction be-and 20-50 ℃, the temperature of reaction of the best is 10-40 ℃.
2, the preparation method of monochloro-o-dimethyl benzene as claimed in claim 1 is characterized in that the catalyzer lewis' acid is iron trichloride, aluminum chloride, butter of antimony, tin tetrachloride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 92104637 CN1033323C (en) | 1992-06-17 | 1992-06-17 | Preparation of monochloro-O-dimethyl benzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 92104637 CN1033323C (en) | 1992-06-17 | 1992-06-17 | Preparation of monochloro-O-dimethyl benzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1080278A true CN1080278A (en) | 1994-01-05 |
| CN1033323C CN1033323C (en) | 1996-11-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 92104637 Expired - Fee Related CN1033323C (en) | 1992-06-17 | 1992-06-17 | Preparation of monochloro-O-dimethyl benzene |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1060462C (en) * | 1997-12-22 | 2001-01-10 | 中国科学院上海有机化学研究所 | Method for prepn. of a, a'-fluorohalogenated xylene |
| CN102382221A (en) * | 2011-08-30 | 2012-03-21 | 广东华林化工有限公司 | Phellandrene resin production process |
| CN103408391A (en) * | 2013-09-02 | 2013-11-27 | 中盐常州化工股份有限公司 | Method for preparing chlorinated aromatic hydrocarbon by chloridizing alkyl aromatic hydrocarbon |
| CN104496744A (en) * | 2014-12-02 | 2015-04-08 | 柳州丰康泰科技有限公司 | Method for synthesizing p-Methylbenzyl chloride |
| CN107694346A (en) * | 2017-10-09 | 2018-02-16 | 山东日兴新材料股份有限公司 | A kind of preparation method of water process brominated polyphenylether anisotropic membrane |
| CN108752161A (en) * | 2018-07-16 | 2018-11-06 | 山东冠森高分子材料科技股份有限公司 | The method of synthesis of alpha-single chloro ortho-xylene in continuous flow micro passage reaction |
| CN113372228A (en) * | 2021-06-08 | 2021-09-10 | 浙江鼎龙科技股份有限公司 | Preparation method of 2-amino-6-chloro-4-nitrophenol |
| CN113563153A (en) * | 2021-08-25 | 2021-10-29 | 中化学科学技术研究有限公司 | Method for preparing monochloro-o-xylene by continuous chlorination of o-xylene |
Families Citing this family (1)
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| CN101914197B (en) * | 2010-08-11 | 2012-02-01 | 郑州大学 | Method for preparing high specific surface area adsorbent resin by photochlorination of dimethylbenzene |
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1992
- 1992-06-17 CN CN 92104637 patent/CN1033323C/en not_active Expired - Fee Related
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1060462C (en) * | 1997-12-22 | 2001-01-10 | 中国科学院上海有机化学研究所 | Method for prepn. of a, a'-fluorohalogenated xylene |
| CN102382221A (en) * | 2011-08-30 | 2012-03-21 | 广东华林化工有限公司 | Phellandrene resin production process |
| CN102382221B (en) * | 2011-08-30 | 2014-07-16 | 广东华林化工有限公司 | Phellandrene resin production process |
| CN103408391A (en) * | 2013-09-02 | 2013-11-27 | 中盐常州化工股份有限公司 | Method for preparing chlorinated aromatic hydrocarbon by chloridizing alkyl aromatic hydrocarbon |
| CN104496744A (en) * | 2014-12-02 | 2015-04-08 | 柳州丰康泰科技有限公司 | Method for synthesizing p-Methylbenzyl chloride |
| CN107694346A (en) * | 2017-10-09 | 2018-02-16 | 山东日兴新材料股份有限公司 | A kind of preparation method of water process brominated polyphenylether anisotropic membrane |
| CN107694346B (en) * | 2017-10-09 | 2020-11-06 | 山东日兴新材料股份有限公司 | Preparation method of brominated polyphenylene oxide asymmetric membrane for water treatment |
| CN108752161A (en) * | 2018-07-16 | 2018-11-06 | 山东冠森高分子材料科技股份有限公司 | The method of synthesis of alpha-single chloro ortho-xylene in continuous flow micro passage reaction |
| CN108752161B (en) * | 2018-07-16 | 2021-02-02 | 山东冠森高分子材料科技股份有限公司 | Method for synthesizing monochloro-o-xylene in continuous flow microchannel reactor |
| CN113372228A (en) * | 2021-06-08 | 2021-09-10 | 浙江鼎龙科技股份有限公司 | Preparation method of 2-amino-6-chloro-4-nitrophenol |
| CN113563153A (en) * | 2021-08-25 | 2021-10-29 | 中化学科学技术研究有限公司 | Method for preparing monochloro-o-xylene by continuous chlorination of o-xylene |
| CN113563153B (en) * | 2021-08-25 | 2024-01-23 | 中化学科学技术研究有限公司 | Method for preparing monochloro-ortho-xylene by continuous chlorination of ortho-xylene |
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| Publication number | Publication date |
|---|---|
| CN1033323C (en) | 1996-11-20 |
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