CN108017506B - Method for preparing 1-chloronaphthalene - Google Patents
Method for preparing 1-chloronaphthalene Download PDFInfo
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- CN108017506B CN108017506B CN201610927193.4A CN201610927193A CN108017506B CN 108017506 B CN108017506 B CN 108017506B CN 201610927193 A CN201610927193 A CN 201610927193A CN 108017506 B CN108017506 B CN 108017506B
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- chloronaphthalene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a novel method for preparing 1-chloronaphthalene. The operation process of the invention is as follows: naphthalene is adopted to react with chlorine in the presence of a solvent and a catalyst, the reaction temperature is 50-80 ℃, and the reaction pressure is normal pressure, so that a reaction solution is obtained. The technical condition is that the solvent adopts kerosene; the catalyst is one or more of ferric sulfide, ferrous sulfide and copper sulfide; the reaction temperature is 50-80 ℃; the reaction time is 2-3 hours. The method for preparing 1-chloronaphthalene of the invention ensures that the naphthalene conversion rate is 100 percent, the 1-chloronaphthalene content in the reaction solution is more than 90 percent, the reaction is carried out at normal temperature and normal pressure, and the effects of saving energy consumption and improving the conversion rate are achieved.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a novel method for preparing 1-chloronaphthalene.
Background
The 1-chloronaphthalene is a chemical with wide application, is mainly used as a medical intermediate, can also be used as an organic solvent, a gas chromatography stationary liquid, an analytical reagent, a bactericide and a mildew preventive, and can be used as a wood preservative
1-chloronaphthalene is generally obtained by direct chlorination of naphthalene: the chlorination reaction takes zinc, iron and the like as catalysts, and the ratio of naphthalene to chlorine is 1: 0.84 to 1.17 percent, the dosage of the catalyst is 0.4 to 0.5 percent of the weight of the naphthalene, the chlorine introducing time is 3 to 6 hours, the reaction temperature is 90 to 95 ℃, the average yield of the 1-chloronaphthalene is 81.7, and the product purity is 96 after secondary fractionation. Or using iodine as catalyst, reacting in solvent chlorobenzene at 60-70 deg.C, introducing chlorine for 6h to end the reaction. The direct chlorination method can simultaneously generate 2-chloronaphthalene which accounts for about 2-20, the boiling points of the two isomers are similar (the boiling point of the 2-chloronaphthalene is 264-. The small-amount production can also be obtained by diazotizing and replacing the menaphthylamine.
The yield of the 1-chloronaphthalene production process is below 85 percent, and the production of the 1-chloronaphthalene is influenced for a long time due to the low yield.
Disclosure of Invention
(1) Technical problem to be solved
The prior production process has the defects of low reaction yield and more impurities.
(2) Technical scheme
A method for preparing 1-chloronaphthalene, characterized by: in the presence of a solvent, adding a metal sulfide as a catalyst into naphthalene serving as a raw material at the temperature of-5-80 ℃, and introducing chlorine gas to react for 1-5 hours to obtain a reaction solution containing 1-chloronaphthalene.
Further, the solvent of the invention adopts kerosene; the catalyst is one or more of ferric sulfide, ferrous sulfide and copper sulfide; the catalyst weight was 1% (Wt) of naphthalene; the reaction temperature is 50-80 ℃; the reaction time is 2-3 hours.
(3) Advantageous effects
The method for preparing 1-chloronaphthalene of the invention ensures that the naphthalene conversion rate is 100 percent, the 1-chloronaphthalene content in the reaction solution is more than 90 percent, the reaction is carried out at normal temperature and normal pressure, and the effects of saving energy consumption and improving the conversion rate are achieved.
Detailed Description
The present invention is further illustrated by the following examples, but is not limited to these examples.
Example 1
30g of naphthalene and 50ml of kerosene are stirred, chlorine is introduced, the reaction temperature is 55 ℃, 0.3g of iron sulfide is adopted as a catalyst, the reaction pressure is normal pressure, the reaction time is 160 minutes, the reaction solution analysis shows that the conversion rate of the naphthalene is 100 percent, and the content of the 1-chloronaphthalene in the reaction solution is 91.2 percent.
Example 2
30g of naphthalene and 60ml of kerosene are stirred, chlorine is introduced, the reaction temperature is 50 ℃, 0.3g of ferrous sulfide is adopted as a catalyst, the reaction pressure is normal pressure, the reaction time is 135 minutes, the reaction solution is analyzed, the naphthalene conversion rate is 100 percent, and the content of 1-chloronaphthalene in the reaction solution is 92.5 percent.
Example 3
30g of naphthalene and 70ml of kerosene are stirred, chlorine is introduced, the reaction temperature is 65 ℃, 0.3g of copper sulfide is adopted as a catalyst, the reaction pressure is normal pressure, the reaction time is 170 minutes, the reaction solution is analyzed, the naphthalene conversion rate is 100 percent, and the content of 1-chloronaphthalene in the reaction solution is 91.6 percent.
Example 4
30g of naphthalene and 60ml of kerosene are stirred, chlorine is introduced, the reaction temperature is 75 ℃, the catalyst adopts 0.15g of iron sulfide and 0.15g of copper sulfide, the reaction pressure is normal pressure, the reaction time is 180 minutes, the reaction solution is analyzed, the conversion rate of the naphthalene is 100 percent, and the content of the 1-chloronaphthalene in the reaction solution is 90.3 percent.
Example 5
30g of naphthalene and 50ml of kerosene are stirred, chlorine is introduced, the reaction temperature is 80 ℃, 0.15g of ferrous sulfide and 0.15g of copper sulfide are adopted as catalysts, the reaction pressure is normal pressure, the reaction time is 155 minutes, the reaction solution is analyzed, the naphthalene conversion rate is 100 percent, and the content of 1-chloronaphthalene in the reaction solution is 90.8 percent.
The above examples show that: the 1-chloronaphthalene prepared under the condition of the invention has the naphthalene conversion rate of 100 percent and the 1-chloronaphthalene content in the reaction liquid of more than 90 percent.
Claims (5)
1. A method for preparing 1-chloronaphthalene, which is characterized by comprising the following steps: adding a metal sulfide as a catalyst into raw material naphthalene in the presence of a solvent at the temperature of-5-80 ℃, and introducing chlorine gas to react for 1-5 hours to obtain a reaction solution containing 1-chloronaphthalene; the solvent adopts kerosene, and the catalyst adopts one or more of ferric sulfide, ferrous sulfide and copper sulfide.
2. The method of claim 1 wherein the catalyst is present in an amount of 1% (Wt) based on naphthalene.
3. The method for preparing 1-chloronaphthalene according to claim 1, wherein the temperature is 50 to 80 ℃.
4. The method for preparing 1-chloronaphthalene according to claim 1, wherein the reaction time is 2 to 3 hours.
5. The method for producing 1-chloronaphthalene according to any one of claims 1 to 4, wherein the naphthalene conversion in the reaction is 100%, and the 1-chloronaphthalene content in the reaction solution is 90% or more.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610927193.4A CN108017506B (en) | 2016-10-31 | 2016-10-31 | Method for preparing 1-chloronaphthalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610927193.4A CN108017506B (en) | 2016-10-31 | 2016-10-31 | Method for preparing 1-chloronaphthalene |
Publications (2)
| Publication Number | Publication Date |
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| CN108017506A CN108017506A (en) | 2018-05-11 |
| CN108017506B true CN108017506B (en) | 2021-03-19 |
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| CN201610927193.4A Active CN108017506B (en) | 2016-10-31 | 2016-10-31 | Method for preparing 1-chloronaphthalene |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5312846A (en) * | 1976-07-21 | 1978-02-04 | Ihara Chem Ind Co Ltd | Chlorination of side chain of 2-methylnaphthaliene |
| CN1210129A (en) * | 1997-08-28 | 1999-03-10 | 徐德坤 | Recovery of carbon, chlorhydric acid, bleaching liquid and gas from waste chloronaphthalene oil |
| CN1257059A (en) * | 1999-12-28 | 2000-06-21 | 眭晓晗 | Catalytic preparation process of toluene monochloride |
| CN1274527A (en) * | 1999-05-19 | 2000-11-29 | 烟台福联生物化学有限公司 | Technological process for producing wax-dissolving penetrant |
| CN103819307A (en) * | 2014-02-12 | 2014-05-28 | 葫芦岛锦化化工工程设计有限公司 | Method for preparing chlorobenzene, p-dichlorobenzene and o-dichlorobenzene in benzene chlorination |
-
2016
- 2016-10-31 CN CN201610927193.4A patent/CN108017506B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5312846A (en) * | 1976-07-21 | 1978-02-04 | Ihara Chem Ind Co Ltd | Chlorination of side chain of 2-methylnaphthaliene |
| CN1210129A (en) * | 1997-08-28 | 1999-03-10 | 徐德坤 | Recovery of carbon, chlorhydric acid, bleaching liquid and gas from waste chloronaphthalene oil |
| CN1274527A (en) * | 1999-05-19 | 2000-11-29 | 烟台福联生物化学有限公司 | Technological process for producing wax-dissolving penetrant |
| CN1257059A (en) * | 1999-12-28 | 2000-06-21 | 眭晓晗 | Catalytic preparation process of toluene monochloride |
| CN103819307A (en) * | 2014-02-12 | 2014-05-28 | 葫芦岛锦化化工工程设计有限公司 | Method for preparing chlorobenzene, p-dichlorobenzene and o-dichlorobenzene in benzene chlorination |
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| CN108017506A (en) | 2018-05-11 |
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