CN111072446A - Preparation method of alkyl cyclohexyl bromobenzene - Google Patents
Preparation method of alkyl cyclohexyl bromobenzene Download PDFInfo
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- CN111072446A CN111072446A CN201911412858.8A CN201911412858A CN111072446A CN 111072446 A CN111072446 A CN 111072446A CN 201911412858 A CN201911412858 A CN 201911412858A CN 111072446 A CN111072446 A CN 111072446A
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- temperature
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- alkylcyclohexylbenzene
- bromine
- bromobenzene
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- -1 alkyl cyclohexyl bromobenzene Chemical compound 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 18
- 239000012074 organic phase Substances 0.000 claims abstract description 11
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 9
- 238000009835 boiling Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 3
- 239000004305 biphenyl Substances 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- 239000007800 oxidant agent Substances 0.000 claims abstract 2
- 230000001590 oxidative effect Effects 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 4
- 239000007858 starting material Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 238000005070 sampling Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- APEHSYGALPMZGD-UHFFFAOYSA-N 1-bromo-2-cyclohexyl-3-propylbenzene Chemical compound C(CC)C=1C(=C(C=CC1)Br)C1CCCCC1 APEHSYGALPMZGD-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- LBURVXAKPYCBBK-UHFFFAOYSA-N 1-bromo-2-cyclohexyl-3-ethylbenzene Chemical compound C(C)C=1C(=C(C=CC=1)Br)C1CCCCC1 LBURVXAKPYCBBK-UHFFFAOYSA-N 0.000 description 3
- GEPBEZWRRNVONZ-UHFFFAOYSA-N 1-cyclohexyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C1CCCCC1 GEPBEZWRRNVONZ-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- MZYNSMBCBNFIHC-UHFFFAOYSA-N 1-bromo-2-cyclohexyl-3-pentylbenzene Chemical compound C(CCCC)C=1C(=C(C=CC1)Br)C1CCCCC1 MZYNSMBCBNFIHC-UHFFFAOYSA-N 0.000 description 2
- PPKHLPLHAGPKOJ-UHFFFAOYSA-N 1-cyclohexyl-2-pentylbenzene Chemical compound C(CCCC)C1=C(C=CC=C1)C1CCCCC1 PPKHLPLHAGPKOJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- QJHIURZXZVAQPR-UHFFFAOYSA-N 1-cyclohexyl-2-propylbenzene Chemical compound CCCC1=CC=CC=C1C1CCCCC1 QJHIURZXZVAQPR-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
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Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of alkyl cyclohexyl bromobenzene, which comprises the following steps: one of alkyl cyclohexyl benzene, alkyl dicyclohexyl benzene and biphenyl is used as a raw material, bromine is used as a bromine source for a synthesis reaction, an oxidant is used as a catalyst, a synthesis product is washed to be neutral by water to obtain a crude organic phase, then a solvent is added into the crude organic phase, the temperature is raised to a boiling state and flows back, and finally the temperature is reduced and filtered to obtain the product.
Description
Technical Field
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method of alkyl cyclohexyl bromobenzene.
Background
In recent years, with the rapid development of liquid crystal display technology, the demand for liquid crystal display materials is expanding, and alkyl cyclohexyl bromobenzene is an important liquid crystal intermediate.
In the prior art, a conventional method for producing alkyl cyclohexyl bromobenzene is shown in figure 1, and alkyl cyclohexyl bromobenzene is synthesized by mainly using alkyl cyclohexyl benzene and bromine as raw materials and iron powder as a catalyst.
The method has the advantages of large bromine consumption, high cost, low yield of 40-60 percent,
therefore, the prior art is subject to further improvement and development.
Disclosure of Invention
In order to solve the problems, a preparation method of alkyl cyclohexyl bromobenzene is provided.
The invention provides the following technical scheme:
a preparation method of alkyl cyclohexyl bromobenzene comprises the following steps: one of alkyl cyclohexyl benzene, alkyl dicyclohexyl benzene and biphenyl is used as a raw material, bromine is used as a bromine source for a synthesis reaction, a synthetic product is washed to be neutral to obtain a crude organic phase, then a solvent is added into the crude organic phase, the temperature is raised to a boiling state and the mixture flows back, and finally the temperature is reduced and the product is obtained after filtration.
Preferably, during the synthesis reaction, the molar ratio of the raw material to bromine is 1: 0.5-1: 0.6.
preferably, the catalyst is H2O2NaClO, NaBrO and HNO3In the above step, the molar addition amount of the catalyst was 0.5 times the amount of the raw material.
Preferably, the reaction temperature is controlled between 0 and 20 ℃ and the reaction time is controlled between 4 and 6 hours during the synthesis reaction.
Preferably, the solvent is any one of methanol, ethanol and acetone, and the weight of the added solvent is 2 times of that of the crude organic phase.
Preferably, the temperature is raised to boiling state and the mixture is refluxed for 1 h.
Preferably, the temperature is reduced to 0 ℃ or lower after refluxing, and then filtration is performed.
Has the advantages that:
the preparation method of the alkyl cyclohexyl bromobenzene can effectively reduce the consumption of bromine and the cost, simultaneously improves the yield to more than 80 percent, does not generate hydrogen bromide waste gas and iron mud solid waste in the production process, and is popularized and used.
Drawings
FIG. 1 is a diagram of the chemical reaction equation for the preparation of alkylcyclohexylbenzene of the prior art;
FIG. 2 is a diagram of the chemical reaction scheme for the preparation of alkylcyclohexylbenzene in accordance with the present invention;
FIG. 3 is a diagram of the chemical reaction scheme for the preparation of ethylcyclohexylbromobenzene in specific example 1 of the present invention;
FIG. 4 is a diagram of the chemical reaction scheme for the preparation of propylcyclohexylbromobenzene in specific example 2 of the present invention;
FIG. 5 is a diagram of the chemical reaction scheme for the preparation of pentylcyclohexylbromobenzene in specific example 3 of the present invention.
Wherein R is C1～C9Linear alkyl group of (1).
Detailed Description
In order to make the technical solutions of the present invention better understood, the following description of the technical solutions of the present invention with reference to the accompanying drawings of the present invention is made clearly and completely, and other similar embodiments obtained by a person of ordinary skill in the art without any creative effort based on the embodiments in the present application shall fall within the protection scope of the present application. In addition, directional terms such as "upper", "lower", "left", "right", etc. in the following embodiments are directions with reference to the drawings only, and thus, the directional terms are used for illustrating the present invention and not for limiting the present invention.
The following are specific examples of the present invention:
specific example 1: preparation of ethylcyclohexylbromobenzene (see FIG. 3 for a specific reaction equation)
Putting 188g of ethyl cyclohexylbenzene and 17g of hydrogen peroxide into a 500ml three-neck flask, stirring and cooling to below 20 ℃, adding 80g of bromine into a constant-pressure dropping funnel, keeping the temperature, slowly dropping, keeping the temperature for 2 hours after dropping, keeping the temperature for 2 hours, and sampling and detecting the bromine to be qualified (the ethyl cyclohexylbenzene is less than 2%, the heat is not qualified, keeping the temperature continuously, and sampling and detecting the bromine once every 1 hour);
adding H into the bottle2O, standing and layering after stirring, and repeating until the pH value is 7;
adding absolute ethyl alcohol with the mass being 2 times of that of the organic phase in the bottle, stirring and heating to boil, keeping boiling and refluxing for 1 hour, cooling to 0 ℃, performing suction filtration, and repeating once again.
Adding the filter cake into a flask, heating until the white solid begins to melt, stirring until the white solid is completely melted, heating, vacuumizing, and drying to obtain 218.4g of colorless liquid product (HPLC GC is 99.3%)
Theoretical yield: 268g of ethylcyclohexylbromobenzene
The yield was 218.4/268%
Specific example 2: preparation of propylcyclohexyl bromobenzene (see FIG. 4 for a specific reaction equation)
Putting 202g of ethyl cyclohexylbenzene and 37.2g of sodium hypochlorite into a 500ml three-neck flask, stirring and cooling to 20 ℃, adding 80g of bromine into a constant-pressure dropping funnel, slowly dropping the bromine at a constant temperature, keeping the temperature for 2 hours after dropping is finished, and keeping the temperature for 2 hours until the sampling detection is qualified (the content of propyl cyclohexylbenzene is less than 2 percent, the temperature is not qualified, keeping the temperature continuously, and sampling and detecting once every 1 hour);
adding H into the bottle2O, standing and layering after stirring, and repeating until the pH value is 7;
adding absolute ethyl alcohol with the mass 2 times of that of the organic phase in the bottle, stirring and heating to boil, keeping boiling and refluxing for 1h, cooling to 0 ℃, performing suction filtration, and repeating once again.
Adding the filter cake into a flask, heating until the white solid begins to melt, stirring until the white solid is completely melted, heating, vacuumizing, and drying to obtain 231.3g (HPLC GC ═ 99.6%)
Theoretical yield: 282g of propylcyclohexyl bromobenzene
The yield was 231.3/282 ═ 100%: 82.0%
Specific example 3: preparation of Pentylcyclohexylbromobenzene (see FIG. 5 for a specific reaction equation)
Putting 230g of pentylcyclohexylbenzene and 59.5g of sodium hypobromite into a 500ml three-neck flask, stirring and cooling to 20 ℃, adding 80g of bromine into a constant-pressure dropping funnel, slowly dropping the bromine at a constant temperature, keeping the temperature for 2 hours after dropping, keeping the temperature for 2 hours, and keeping the temperature for qualified sampling detection (the pentylcyclohexylbenzene is less than 2 percent, the temperature is not qualified, keeping the temperature continuously, and sampling and detecting once every 1 hour);
adding H into the bottle2O, standing and layering after stirring, and repeating until the pH value is 7;
adding absolute ethyl alcohol with the mass 2 times of that of the organic phase in the bottle, stirring and heating to boil, keeping boiling and refluxing for 1h, cooling to 0 ℃, performing suction filtration, and repeating once again.
Adding the filter cake into a flask, heating until the white solid begins to melt, stirring until the white solid is completely melted, heating, vacuumizing, and drying to obtain 259.4g (99.2% GC for HPLC)
Theoretical yield: 310g of propylcyclohexylbromobenzene
The yield is 259.4/310 × 100% ═ 83.7%
The quality and yield of the product synthesized according to the above examples 1-3 are shown in table 1:
table 1: the process of the invention can synthesize the product with high quality and yield
| Example numbering | Product appearance | Yield of | HPLC content |
| Example 1 | Colourless liquid | 81.5％ | 99.3％ |
| Example 2 | White solid | 82％ | 99.6％ |
| Example 3 | White solid | 83.7％ | 99.2％ |
The present invention has been described in detail, and it should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention.
Claims (9)
1. A preparation method of alkyl cyclohexyl bromobenzene is characterized by comprising the following steps: one of alkyl cyclohexyl benzene, alkyl dicyclohexyl benzene and biphenyl is used as a raw material, bromine is used as a bromine source for synthesis reaction, an oxidant is used as a catalyst, a synthetic product is washed to be neutral by water to obtain a crude organic phase, then a solvent is added into the crude organic phase, the temperature is raised to a boiling state and the mixture flows back, and finally the temperature is lowered and the product is obtained after filtration.
2. The method for preparing alkylcyclohexyl bromobenzene as claimed in claim 1, wherein during the synthesis reaction, the molar ratio of raw material to bromine is 1: 0.5-1: 0.6.
3. the method for preparing alkylcyclohexylbenzene according to claim 1, wherein the catalyst is H2O2NaClO, NaBrO and HNO3One kind of (1).
4. The method for preparing alkylcyclohexylbenzene according to claim 3, wherein the molar addition amount of the catalyst is 0.5 times the molar amount of the starting material.
5. The method for preparing alkylcyclohexylbenzene according to claim 1, wherein the reaction temperature is controlled at 0-20 ℃ and the reaction time is controlled at 4-6 hours during the synthesis reaction.
6. The method for preparing alkylcyclohexylbenzene according to claim 1, wherein the solvent is any one of methanol, ethanol and acetone.
7. The method for preparing alkylcyclohexylbenzene according to claim 1, wherein the weight of the added solvent is 2 times of that of the crude organic phase.
8. The method for preparing alkylcyclohexylbenzene according to claim 1, wherein the temperature is raised to boiling and the reflux is carried out for 1 hour.
9. The method for preparing alkylcyclohexyl bromobenzene as claimed in claim 1, wherein the temperature is reduced to below 0 ℃ after refluxing for filtration.
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| CN201911412858.8A CN111072446A (en) | 2019-12-31 | 2019-12-31 | Preparation method of alkyl cyclohexyl bromobenzene |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5654493A (en) * | 1995-08-26 | 1997-08-05 | Hoechst Aktiengesellschaft | Process for preparing 4-bromophenyl alkyl ethers |
| US20050137431A1 (en) * | 2003-12-15 | 2005-06-23 | Bedekar Ashutosh V. | Process for eco-friendly synthesis of bromobenzene |
| CN102603497A (en) * | 2012-03-06 | 2012-07-25 | 蚌埠中实化学技术有限公司 | 1-alkoxy-4-[4-(4-alkyl cyclohexyl) phenyl]-2, 3-difluorobenzene and synthetic method thereof |
| CN103483153A (en) * | 2013-08-30 | 2014-01-01 | 烟台海川化学制品有限公司 | Preparation method of trans-4,4'-(1-bromophenyl)-cyclohexanol |
| CN103525429A (en) * | 2013-08-30 | 2014-01-22 | 晶美晟光电材料（南京）有限公司 | Liquid crystal compound and preparation method thereof as well as liquid crystal mixture containing liquid crystal compound and application of liquid crystal mixture |
-
2019
- 2019-12-31 CN CN201911412858.8A patent/CN111072446A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5654493A (en) * | 1995-08-26 | 1997-08-05 | Hoechst Aktiengesellschaft | Process for preparing 4-bromophenyl alkyl ethers |
| US20050137431A1 (en) * | 2003-12-15 | 2005-06-23 | Bedekar Ashutosh V. | Process for eco-friendly synthesis of bromobenzene |
| CN102603497A (en) * | 2012-03-06 | 2012-07-25 | 蚌埠中实化学技术有限公司 | 1-alkoxy-4-[4-(4-alkyl cyclohexyl) phenyl]-2, 3-difluorobenzene and synthetic method thereof |
| CN103483153A (en) * | 2013-08-30 | 2014-01-01 | 烟台海川化学制品有限公司 | Preparation method of trans-4,4'-(1-bromophenyl)-cyclohexanol |
| CN103525429A (en) * | 2013-08-30 | 2014-01-22 | 晶美晟光电材料（南京）有限公司 | Liquid crystal compound and preparation method thereof as well as liquid crystal mixture containing liquid crystal compound and application of liquid crystal mixture |
Non-Patent Citations (1)
| Title |
|---|
| 唐培堃等: "《精细有机合成化学及工艺学》", 30 November 1993, 天津大学出版社 * |
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