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A kind of preparation method of 5-hydroxyl-1-tetralone

A technology of tetralone and dihydroxynaphthalene, applied in the field of preparation of nano-microsphere-metal composite catalyst and 5-hydroxy-1-tetralone, can solve the problems of difficult synthesis, poor selectivity, no Mention and other issues to achieve the effect of easy regeneration, reducing the loss of raw materials and energy, and regular and orderly appearance

Active Publication Date: 2019-08-06
HANGZHOU LUPU BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing preparation method, hydroxy-1-tetralone can be prepared by oxidizing the raw material 1,2,3,4-tetrahydro-1-naphthalene, but the reaction needs to be carried out in the presence of peroxide; 5-hydroxymethyl-1-tetralone can be obtained by hydrolysis of 5-hydroxymethyl-1-tetralone, but the reaction raw material 5-hydroxymethyl-1-tetralone itself is not easy to synthesize
[0003] The method for preparing 5-hydroxyl-1-tetralone by reducing 1,5-binaphthol is relatively common, among which there is one Russian document [Russian Journal of Organic Chemistry 2000,36,1474] and one Russian Chinese patents respectively report Lewis acid reduction [Russian patent 2356883, 2009], but the reaction process needs to use a large amount of aluminum trichloride and aluminum tribromide, and neither the paper nor the patent mentions which reducing agent to use
Catalyzed hydrogenation reduction by metal palladium or nickel, the reaction is feasible and the process is relatively green, but, because the raw material 1,5-binaphthol and the product 5-hydroxyl-1-tetralone are prone to excessive reduction reaction under catalytic hydrogenation conditions , so the selectivity of the reaction process is poor, and the yield does not exceed 60%.

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preparation example Construction

[0029] The present invention provides the preparation method of nano microsphere-metal composite catalyst described in the above scheme, comprising the following steps:

[0030] SiO 2 The nanospheres were soaked in the palladium salt solution to obtain the soaked SiO 2 Palladium salt solution of nano-microspheres;

[0031] will be soaked with SiO 2 The palladium salt solution of the nanospheres was heated to dryness to obtain SiO 2 Nano microsphere-palladium salt complex;

[0032] The SiO 2 The nanometer microsphere-palladium salt complex is reduced by hydrogen to obtain the nanometer microsphere-metal composite catalyst.

[0033] In the present invention, SiO 2 The nanospheres were soaked in the palladium salt solution to obtain the soaked SiO 2 Palladium Salt Solution of Nanospheres. The present invention to the SiO 2 There is no special requirement for the source of the nanospheres, and they can be prepared using methods well known to those skilled in the art. In s...

Embodiment 1

[0054] SiO 2 Preparation of nanosphere seeds:

[0055] Weigh 0.1756g of arginine into a 250mL round bottom flask, add 170.05g of deionized water, stir to dissolve, add 10.4139g of tetraethyl silicate, raise the temperature to 70°C, keep the speed at 460rpm, and put a stopper on the top of the flask , stirred in an oil bath at 70°C for 24 hours. After the reaction, it was transferred to a hydrothermal kettle with a polytetrafluoroethylene liner of 1000 mL, and heated in an oven at 100°C for 20 hours. Then transfer it to a crystallization dish and put it in an oven to dry at 100°C. After drying, put it into a muffle furnace and bake it at 600°C for 4 hours to obtain SiO 2 Nano-microsphere seeds, the product is in the form of translucent filaments.

[0056] 200nm SiO 2 Preparation of microspheres:

[0057] Weigh 41.4 g of deionized water into a 250 mL round bottom flask, add 0.1360 g of seed solution, 133.6 g of ethanol, and 0.2613 g of arginine, stir and dissolve at room te...

Embodiment 2

[0065] (1) 5%Pd / SiO 2 Preparation of 200nm microsphere catalyst:

[0066] Take by weighing the 200 nanometers of SiO that embodiment 1 prepares 2 2.0 grams of nanospheres, add 10 grams containing 167 mg of PdCl 2 solution, after soaking for 0.5h, the mixture was heated and stirred until dry, and the obtained SiO 2 The nanosphere-palladium salt complex was cooled to room temperature, and finally the dried SiO 2 The nanosphere-palladium salt complex was reduced by hydrogen at 350°C for 4 hours to prepare a nanosphere-metal composite catalyst with a Pd loading of 5% (5%Pd / SiO 2 200 nm microsphere catalyst).

[0067] 200 nm SiO using SEM 2 Nanospheres were observed, and the results were as follows figure 1 shown, according to figure 1 It can be seen that the obtained SiO 2 The nano-microspheres have a uniform particle size and are in the form of white flakes.

[0068] The obtained 5%Pd / SiO 2 200 nanometer microsphere catalyst was observed, and the obtained results are as...

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Abstract

The invention provides a nanosphere-metal composite catalyst. The nanosphere-metal composite catalyst is prepared from SiO2 nanospheres and Pd metal particles loaded on the surfaces of the SiO2 nanospheres. The nanosphere-metal composite catalyst provided by the invention has higher catalytic activity and selectivity and can catalyze hydrogenation reaction by high efficiency. The invention also provides a preparation method of the catalyst; the catalyst can be prepared by an impregnation method, the preparation method is simple, the operation is easy and the cost is low; the nanosphere-metal composite catalyst provided by the invention is utilized to catalyze hydrogenation reaction of 1,5-dihydroxynaphthalene, the reaction selectivity is high and the yield of 5-hydroxyl-1-tetralone is high.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical intermediates, in particular to a nanometer microsphere-metal composite catalyst and a preparation method thereof, and a preparation method of 5-hydroxyl-1-tetralone. Background technique [0002] 5-Hydroxy-1-tetralone is an important pharmaceutical intermediate, which is widely used in the synthesis of medicines such as levobunolol hydrochloride. In the existing preparation method, hydroxy-1-tetralone can be prepared by oxidizing the raw material 1,2,3,4-tetrahydro-1-naphthalene, but the reaction needs to be carried out in the presence of peroxide; 5-hydroxymethyl-1-tetralone can be obtained by hydrolysis of 5-hydroxymethyl-1-tetralone, but the reaction raw material 5-hydroxymethyl-1-tetralone itself is not easy to synthesize. [0003] The method for preparing 5-hydroxyl-1-tetralone by reducing 1,5-binaphthol is relatively common, among which there is one Russian document [Russian Journal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J23/44B01J35/08B01J37/10B01J37/18C07C49/747C07C45/00
CPCB01J23/44B01J35/0013B01J35/08B01J37/10B01J37/18C07C45/006C07C2602/10C07C49/747
Inventor 徐伟明冯冬祥项佳运沈鸿云
Owner HANGZHOU LUPU BIOTECH CO LTD
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