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Method for preparing alpha-phenethyl alcohol by catalyzing acetophenone hydrogenation with supported amorphous alloy

An amorphous alloy and phenylethyl alcohol technology, which is applied in the field of synthesis of spices and pharmaceutical intermediates, can solve the problems of unfavorable catalyst strength, unfavorable large-scale industrial production, weak interaction between active components and carriers, etc.

Inactive Publication Date: 2019-10-25
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patent CN107999082A provides a copper-based acetophenone hydrogenation catalyst that improves activity, selectivity and prolongs service life by adding auxiliary salt compounds. The conversion rate of acetophenone can still be kept above 98% after 2000 hours of reaction, but the catalyst Rare earth metals such as La and Ce need to be added during the preparation process, and the cost is high
EP1701877B1 uses alkali metals and alkaline earth metals to modify copper-silicon hydrogenation catalysts, which limits the generation of by-products such as ethylbenzene. The silicon source is added in the form of fumed silica or diatomaceous earth, resulting in weak interaction between the active component and the carrier. Bad for catalyst strength
CN108043414A proposes a preparation method of a copper-based catalyst for acetophenone liquid-phase hydrogenation to α-phenylethanol, which significantly suppresses side reactions such as hydrogenolysis and improves catalytic activity and selectivity, but the catalyst needs to be fed with different proportions before use H 2 , N 2 The mixed gas is activated, and the operation is cumbersome
Amorphous Ni-Sn-B / SiO prepared by chemical reduction method was reported in Chinese patent CN1557545A 2 Catalyzing the hydrogenation of acetophenone to α-phenylethanol, the selectivity can reach up to 97.5%. However, the nickel-based amorphous alloy catalyst is easily oxidized and deactivated, and is not easy to store; and my country's nickel resources only account for 3.7% of the world's total reserves. The source price is relatively high, which is not conducive to large-scale industrial production

Method used

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  • Method for preparing alpha-phenethyl alcohol by catalyzing acetophenone hydrogenation with supported amorphous alloy
  • Method for preparing alpha-phenethyl alcohol by catalyzing acetophenone hydrogenation with supported amorphous alloy

Examples

Experimental program
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Effect test

Embodiment 1

[0017] (1) Roast 20-80 mesh silica gel carrier in a muffle furnace at 550°C for 5 hours, add a certain amount of saturated CuCl 2 2H 2 O solution was impregnated with an equal volume for 2 h, and then dried under vacuum at 100 °C. In an ice-water bath, 2M NaOH solution of sodium borohydride was slowly added dropwise onto the silica gel carrier impregnated with copper chloride, and stirred until no bubbles were released. The obtained catalyst was washed with distilled water, soaked with ethanol and stored in a closed container for future use. In the catalyst prepared in this embodiment, the active component copper accounts for 30% by mass percentage.

[0018] (2) In a 50mL stainless steel autoclave, sequentially add 10mL ethanol, 3g acetophenone and 0.9g supported Cu-B / SiO prepared in step (1) 2 Amorphous alloy catalyst. Seal the autoclave and pass in nitrogen gas to test for leaks, and then replace it 4 to 5 times to remove the air in the autoclave. Add hydrogen to set th...

Embodiment 2～13

[0020] (1) Calcinate different carrier materials in a muffle furnace at 550 °C for 5 h, add a certain amount of saturated Cu(CH 3 COO) 2 ·H 2 O and Ni(CH 3 COO) 2 4H 2 The mixed solution of O was impregnated with equal volume for 8h, and then dried under vacuum at 110℃. While stirring in an ice-water bath, 2M NaOH solution of potassium borohydride was slowly added dropwise onto the support containing copper and nickel, and reacted until no bubbles were released. The obtained catalyst was washed with distilled water, soaked with ethanol, and put into a closed container for later use. In the catalyst prepared in this embodiment, the active component copper nickel accounts for 10% by mass percentage. The catalyst Cu / (Cu+Ni) atomic ratio, B / (Cu+Ni) atomic ratio and carrier selection during the preparation process are listed in Table 1.

[0021] (2) In a 50 mL stainless steel autoclave, 10 mL of solvent ethanol, 3 g of acetophenone and 0.9 g of the supported Cu-Ni-B amorphou...

Embodiment 14

[0025] (1) Roast 20-60 mesh silica gel in a muffle furnace at 550°C for 5 hours, add a certain amount of saturated NiCl 2 ·6H 2 O solution was impregnated with equal volume for 24h, and then vacuum dried at 120°C. At room temperature, slowly drop 2M potassium borohydride NaOH solution onto the activated carbon impregnated with nickel chloride, and stir until no bubbles are released. The obtained catalyst was washed with distilled water, soaked with ethanol, and put into a closed container for later use. In the catalyst that present embodiment makes, by mass percentage, active component nickel accounts for 40%

[0026] (2) Prepare α-phenylethanol by hydrogenation in the same method and condition as in Example 1 step (2), the catalyst is changed to 0.9g amorphous Ni-B / SiO 2, The result of hydrogenation was 96.3% conversion of acetophenone and 60.6% selectivity of α-phenylethanol.

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Abstract

The invention belongs to the technical field of chemical engineering and in particular relates to a method for preparing alpha-phenethyl alcohol by catalyzing acetophenone hydrogenation with a supported amorphous alloy. An amorphous alloy catalyst consists of copper, nickel, boron and a porous carrier material Z, wherein the copper mainly exists in a mode of a Cu-Ni-B amorphous alloy. The preparation method comprises the following step: reducing active components, namely copper and nickel, into a carrier through BH4-. The catalyst is low in raw material price and safe to use, is applied to reactions for preparing phenethyl alcohol through acetophenone hydrogenation, and has good stability and selectivity when being compared with a conventional nickel-based catalyst; and when the acetophenone conversion rate is up to 98% or greater, the selectivity of alpha-phenethyl is up to 97%, and the activity of the catalyst after 300 hours of reactions is still maintained at a high level.

Description

technical field [0001] The invention relates to the technical field of synthesis of spices and pharmaceutical intermediates, in particular to a method for preparing α-phenethyl alcohol by catalyzing the hydrogenation of acetophenone by a supported Cu-Ni-B amorphous alloy. Background technique [0002] Aromatic alcohols are important chemical products for the manufacture of medicines and synthetic fragrances. α-phenylethyl alcohol is the most representative compound among aromatic alcohols, and it is an important intermediate in drug synthesis. For example, in the synthesis of ibuprofen, a non-steroidal antipyretic and analgesic drug, α-phenylethyl alcohol is important Raw materials; it is widely used in fragrance production for aroma reconciliation, and it is used as the main component of various essential oils because of its floral fragrance. An effective method for the synthesis of α-phenylethanol is generally to convert acetophenone into phenylethanol by hydrogenation re...

Claims

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Application Information

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IPC IPC(8): B01J23/755B01J37/02B01J37/16C07C29/141C07C33/22
CPCB01J23/755B01J37/0201B01J37/16C07C29/141C07C33/22Y02P20/52
Inventor 吕志果王娇媚郭振美张超张述英程曦
Owner QINGDAO UNIV OF SCI & TECH
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