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Method for preparing 1,3-methyl glycol by catalytic hydrogenation of 3-hydroxy propionic ester

A hydroxypropionate, propylene glycol technology, applied in the preparation of hydroxyl compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problem of low production efficiency, unstable toxicity of acrolein, affecting the service life and stability of catalysts, etc. question

Active Publication Date: 2011-03-02
SHANGHAI HUAYI ENERGY CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

US5,770,776, US5,723,389, US5,731,478, US5,777,182 etc. have described oxirane hydroformylation, and this technique has shortcomings such as catalyst selection and improvement difficulties, complicated reactor structure; US6,232,511 and US6,140543 hydration and hydrogenation of acrolein to synthesize 1,3-propanediol has been described. The disadvantage of this method is that the raw material acrolein is extremely unstable and highly toxic
Above-mentioned two kinds of method numbers all need to be intermediate synthesis step through 3-hydroxy propionaldehyde, and there are following problems: because the instability of aldehyde self forms oligomer and generates acetal etc., brings difficulty to hydrogenation process, makes final The quality of the product is reduced; especially in order to suppress the formation of acetal, etc., it needs to be carried out in a very low concentration range of raw materials, and the production efficiency is not high
In addition, due to the use of alkali metal salts as precipitating agents in the catalyst preparation process, it is necessary to adopt cumbersome steps and consume a large amount of deionized water to wash and remove the alkali metal ions in the precursor of the catalyst precursor, even if the catalyst is washed repeatedly. The content of alkali metal ions is still maintained at a relatively high level (200-500ppm, JP2004-34021). It is these alkali metal ions remaining in the catalyst that make the active components easy to sinter, which seriously affects the service life and stability of the catalyst.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] 10.0g Cu(NO 3 ) 2 ·3H 2 O was dissolved in 75ml of distilled water and the aqueous solution obtained was added dropwise with ammonia water under stirring. After the precipitation occurred, continue to add ammonia water and wait for the precipitation to dissolve to obtain dark blue solution A. Dissolve Cu(NO in 100ml of distilled water. 3 ) 2 ·3H 2 O 20.0g, Zn(NO 3 ) 2 ·6H 2 O16.7g made solution B. Mix solutions A and B under stirring at 20°C, and keep the temperature for 2 hours, add 25 ml of 0.5M ammonium hypophosphite aqueous solution, stir and react for 18 hours, then add silica sol aqueous solution (produced by Qingdao Ocean Chemical Factory, ammonia Stable type, silicon dioxide content 25-26%, particle size 10-20nm) 26.3g, raise the temperature to 85°C, continue stirring for 6 hours for aging. After filtering and drying at 120°C for 12 hours, the powder is pressed into shape, crushed and sieved again to select particles with a size of 40-80 mesh, and roaste...

Embodiment 2

[0016] 10.0g Cu(NO 3 ) 2 ·3H 2 O was dissolved in 75ml of distilled water and the aqueous solution obtained was added dropwise with ammonia water under stirring state. After the precipitation occurred, continue to add ammonia water and wait for the precipitation to dissolve to obtain dark blue solution A. Dissolve Cu(NO in 50ml of distilled water. 3 ) 2 ·3H 2 O 10.0g, Zn(NO 3 ) 2 ·6H 2 O 8.7g made solution B. Mix solutions A and B under stirring conditions at 35°C, and keep the temperature to continue the reaction for 17 hours, add 25ml of 0.5M ammonium hypophosphite aqueous solution, stir and react for 3 hours, then add 35.2g of ammonia-stable silica sol, and raise the temperature to Up to 55°C, continue stirring for 18 hours for aging. After filtering and drying at 120°C for 12 hours, the powder is pressurized and shaped, crushed and sieved again to select particles with a size of 40 to 80 meshes, and roasted at 850°C for 18 hours to obtain the hydrogenation catalyst...

Embodiment 3

[0018] 10.0g Cu(NO 3 ) 2 ·3H 2 O was dissolved in 75ml of distilled water and the aqueous solution obtained was added dropwise with ammonia water under stirring state. After the precipitation occurred, continue to add ammonia water and wait for the precipitation to dissolve to obtain dark blue solution A. Dissolve Cu(NO in 50ml of distilled water. 3 ) 2 ·3H 2 O 10.0g, Zn(NO 3 ) 2 ·6H 2 O 8.7g made solution B. Mix solutions A and B under stirring at 15°C, and keep the temperature to continue the reaction for 10 hours, add 25ml of 0.5M ammonium hypophosphite aqueous solution, stir and react for 3 hours, then add 35.2g of ammonia-stable silica sol, and raise the temperature to Up to 55°C, continue stirring for 18 hours for aging. After filtering and drying at 120°C for 12 hours, press the powder into shape, crush and sieve again to select particles with a size of 40 to 80 meshes, and roast at 850°C for 18 hours to obtain the hydrogenation catalyst of the present invention...

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PUM

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Abstract

The invention discloses a method for preparing 1, 3-propanediol through 3-hydroxy propionate hydrogenation, which comprises two procedures: firstly, preparing hydrogenation catalyst: adding ammonium salt solution in copper salt solution reacting and generating complex, mixing the complex solution and the solution with copper salt and zinc salt under temperature and stirring conditions, adding ammonium hypophosphite solution and catalyst formed via gel by filtering, drying, forming and roasting, the gel is formed via silica sol by aging; then filling catalyst finished product in fixed bed reactor, warming up the reactor slowly while feeding mixed gas of H2 and N2 or argon, pumping in the mix of 3-hydroxy propionate hydrogenation and fatty alcohol solvent can generate target product 1, 3-propanediol with high selection; materials can be returned to the reactor directly or through separation, so as to improve the reaction yield at the reactor outlet. The invention has the advantages of high stability, high activity, high selectivity, and good industrial application value.

Description

technical field [0001] The invention relates to the technical field of organic chemical industry, in particular to a method for preparing 1,3-propanediol by hydrogenating 3-hydroxypropionate. technical background [0002] 1,3-propanediol is an important organic chemical raw material, widely used in polymer production, such as thermoplastic polyurethane, copolyether, polytrimethylene terephthalate (PTT), etc., especially 1,3-propanediol and p- The PTT polyester fiber obtained by polymerizing methyl phthalate has more excellent properties than polyester materials synthesized by other diols, and has broad development prospects. In addition, 1,3-propanediol can also be used as organic synthesis intermediates such as solvents, antifreeze agents, protective agents and synthetic medicines. [0003] In the prior art, there are two main industrial production routes of 1,3-propanediol: the hydroformylation of ethylene oxide to synthesize 3-hydroxypropanal, the method of hydrogenating...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C31/20C07C29/149
Inventor 吕志果赵正康郭振美应于舟杨菊群张旭红冯看卡
Owner SHANGHAI HUAYI ENERGY CHEM