Synthesis method of 1-propyl-[4-(4 '-butylphenylazo)] azobenzene
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A kind of technology of butylbenzene azo group and synthetic method, applied in directions such as organic chemistry
Pending Publication Date: 2022-04-12
烟台丰鲁精细化工有限责任公司
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[0003] At present, there are no literature and patent reports on the synthesis method of 1-propyl-[4-(4'-butylphenylazo)]azobenzene
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Embodiment 1
[0042] (1) Intermediate 1: Preparation of 4-nitro-nitrosobenzene (M1):
[0043]
[0044] Add 126 g of potassium hydrogen persulfate and 1000 g of water into the three-necked flask, stir in an ice bath and cool down to 15°C. Add 36 g of 4-nitroaniline into the bottle, react at 40° C. for 2 hours, and there is no raw material point detected by TLC. Suction filter the filter cake back into the bottle, add 126 g of dichloromethane and stir wash for 30 minutes, suction filter, and dry the filter cake to obtain yellow flaky solid 4-nitro-nitrosobenzene (M1), with a yield of 80%.
[0045] (2) Preparation of 4-n-butyl-4'-nitroazobenzene (M2):
[0046]
[0047] Add 25g of M1 to the three-necked flask, then add a mixed solution of 26.2g of 4-n-butylaniline and 785g of acetic acid, and stir overnight at 40°C. TLC detects that there is no raw material point, and the reaction is stopped. Pour the reaction solution into a three-necked flask, add 1000 g of water, and precipitate a b...
Embodiment 2
[0058] (1) Intermediate 1: Preparation of 4-nitro-nitrosobenzene (M1):
[0059]
[0060] Add 189 g of potassium hydrogen persulfate and 1500 g of water into the three-necked flask, stir in an ice bath and cool down to 15°C. Add 54 g of 4-nitroaniline to the bottle, react at 40° C. for 2 hours, and there is no raw material point detected by TLC. Suction filter the filter cake back into the bottle, add 189g of dichloromethane and stir wash for 30 minutes, suction filter, and dry the filter cake to obtain yellow flaky solid 4-nitro-nitrosobenzene (M1), with a yield of 80.5%.
[0061] (2) Preparation of 4-n-butyl-4'-nitroazobenzene (M2):
[0062]
[0063] Add 37.5g of M1 to the three-necked flask, and then add a mixed solution of 39.3g of 4-n-butylaniline and 1177g of acetic acid, and stir overnight at 40°C for reaction. TLC detects that there is no raw material point, and the reaction is stopped. The reaction solution was poured into a three-necked flask, and 1500 g of w...
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Abstract
The invention relates to a synthesis method of 1-propyl-[4-(4 '-butylphenylazo)] azobenzene. The synthesis method comprises the following steps: carrying out a reaction on potassium hydrogen persulfate and 4-nitroaniline to obtain 4-nitro-nitrosobenzene, carrying out a reaction on the 4-nitro-nitrosobenzene, 4-n-butylaniline and acetic acid, and carrying out post-treatment to obtain 4-n-butyl-4'-nitro azobenzene; the preparation method comprises the following steps: dissolving 4-n-butyl-4 '-nitroazobenzene in DMF (Dimethyl Formamide), and reducing by hydrazine hydrate to obtain 4-n-butyl-4'-aminoazobenzene; the preparation method comprises the following steps: stirring 4-n-butyl-4 '-aminoazobenzene, concentrated hydrochloric acid and water, dropwise adding a sodium nitrite solution, dropwise adding a propylaniline glacial acetic acid solution, reacting, and performing post-treatment to obtain the 1-propyl-[4-(4'-butylphenylazo)] azobenzene. The synthesis method of the 1-propyl-[4-(4 '-butylphenylazo)] azobenzene is reasonable in process design, low in raw material cost, easy in purification treatment, high in yield and suitable for small-batch production.
Description
technical field [0001] The invention relates to a synthesis method of 1-propyl-[4-(4'-butylphenylazo)]azobenzene, which belongs to the technical field of organic synthesis. Background technique [0002] Azo dyes are the earliest dyes used in the "guest-host" effect due to their molecular structure characteristics and modifiability, and have been widely used in liquid crystal color displays. The preparation method of azo dye is simple, and it has good optical properties, thermal stability and solubility after mixing with liquid crystal, which is of great significance for improving the quality and performance of liquid crystal display. At present, the research on azo dyes focuses on increasing the width of the absorption spectrum of azo dyes in liquid crystals; improving the dichroism and order parameters of dyes; enhancing the solubility and photostability of dyes in liquid crystals, etc. The absorption wavelength of the structure of 1-propyl-[4-(4'-butylphenylazo)]azobenzen...
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