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A kind of synthetic method of pentanediol and a kind of synthetic method based on lactic acid conversion to prepare biomass baseline linear pentadiene

A synthesis method, pentadiene technology, applied in the direction of condensation preparation of carbonyl compounds, carbon-based compound preparation, hydroxyl compound preparation, etc., can solve the problems of linear pentadiene with little industrial value, low catalytic efficiency, poor process flexibility, etc. , to achieve good conversion effect, easy raw materials and catalysts, and simple operation

Active Publication Date: 2022-07-12
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

The biological fermentation method involves bioengineering (metabolism, fermentation process), genetic technology (genetic modification), etc. Although the conditions are mild, the process is complicated, the efficiency is low, and the process flexibility is poor.
And in the field of catalytic transformation of biomass, so far, only three routes can prepare 1,3-pentadiene: (1) furfural is converted into methyl tetrahydrofuran through methyl furan, and finally dehydration obtains 1,3-pentadiene (RubberChemistryand Technology, 1945, 18, 284–285; ACS Catalysis, 2017, 7, 5248-5256), this method has a long route, low yield (<30%), and high material and energy consumption; Xylitol is used as a raw material, deoxygenation and dehydration (DODH) under the action of formic acid, and then deep deoxygenation to obtain linear pentadiene, the yield is not more than 51.8%. DODH is the key to this route. Formic acid is both a catalyst and a reactant. As a catalyst , formic acid catalyzed xylitol dehydration and DODH are in a competitive relationship, resulting in low catalytic efficiency, and the lack of reducing agent in the DODH system, so the yield is low (Green Chemistry, 2017, 19, 638–642); Ketone / formaldehyde is used as raw material, which is first condensed to obtain linear hydroxy ketone, then hydrogenated to 1,3-pentanediol, and then dehydrated to convert to linear pentadiene. The chemical environment is different, and the hydrogen on the methylene is more active under the reaction conditions, which leads to the reaction tends to generate nonlinear hydroxy ketones, and finally generates isoprene, so the industrial value of this route for preparing linear pentadiene is not great

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  • A kind of synthetic method of pentanediol and a kind of synthetic method based on lactic acid conversion to prepare biomass baseline linear pentadiene
  • A kind of synthetic method of pentanediol and a kind of synthetic method based on lactic acid conversion to prepare biomass baseline linear pentadiene
  • A kind of synthetic method of pentanediol and a kind of synthetic method based on lactic acid conversion to prepare biomass baseline linear pentadiene

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[0086] The invention provides a kind of synthetic method of pentanediol, comprising the following steps:

[0087] 1) The mixed solution after mixing pentanedione, a hydrogenation catalyst and an organic solvent is subjected to a hydrogenation reaction to obtain pentanediol in an atmosphere containing hydrogen.

[0088] In principle, the present invention has no special restrictions on the amount of the hydrogenation catalyst, and those skilled in the art can select and adjust according to practical application needs, product requirements and quality requirements. For efficiency, the concentration of the hydrogenation catalyst in the mixed solution is preferably 1-30 mg / ml, more preferably 6-25 mg / ml, and more preferably 11-20 mg / ml.

[0089] In principle, the present invention does not limit the amount of pentanedione in the mixed solution. Those skilled in the art can select and adjust according to practical application needs, product requirements and quality requirements. Th...

Embodiment 1

[0205] (1) reaction of lactic acid condensation to prepare pentanedione:

[0206] Weigh 2.0g of sodium bicarbonate to prepare 5ml of solution, add 5g of MgO under stirring, let stand for 12h, and dry at 120°C for 10h. Before use, MgO was calcined at 550 °C for 4 h to obtain a condensation catalyst. Weigh 1.5 g of the catalyst and put it into the fixed-bed reactor; before the reaction, the catalyst is at 550 ° C, and the treatment time is preferably 3 h; during the reaction, the feed rate of raw materials is 0.06 ml / min, the flow rate of nitrogen gas is 60 ml / min, and the reaction temperature is 380 °C. The yield of the obtained pentanedione was 73%, and the conversion rate of the raw material was 89%.

[0207] (2) pentanedione hydrogenation to produce pentanediol reaction:

[0208] will Al 2 O 3 After the carrier was calcined at 500°C for 5h, 3.0g was weighed into a beaker, 3ml of chloroplatinic acid solution was added, stirred for 10min, left to stand overnight, dried in...

Embodiment 2

[0212] (1) reaction of lactic acid condensation to prepare pentanedione:

[0213]Weigh 1.8g potassium bicarbonate and configure it into 5ml solution, add 5g Al under stirring condition 2 O 3 , stand for 12h, and dry at 120°C for 10h. Al before use 2 O 3 It was calcined at 600°C for 5h to obtain a condensation catalyst. Weigh 2.0 g of the catalyst and load it into the fixed-bed reactor; before the reaction, the catalyst is kept at 500 ° C, and the treatment time is preferably 4 h; during the reaction, the feed rate of raw materials is 0.08 ml / min, the flow rate of nitrogen gas is 60 ml / min, and the reaction temperature is 300 °C. The yield of pentanedione obtained was 62%, and the conversion rate of raw materials was 93%.

[0214] (2) pentanedione hydrogenation to produce pentanediol reaction:

[0215] ZrO 2 After the carrier was calcined at 500°C for 5h, 3.0g was weighed into a beaker, 3ml of cerium nitrate solution was added, the loading of cerium nitrate was controll...

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Abstract

The invention provides a method for synthesizing pentanediol, which comprises the following steps. The mixed solution obtained by mixing pentanedione, a hydrogenation catalyst and an organic solvent is subjected to hydrogenation reaction to obtain pentanediol in an atmosphere containing hydrogen. . The present invention can utilize the cheap and readily available bulk bio-based chemical lactic acid to obtain pentanediol and further obtain linear pentadiene. The raw materials in the present invention are derived from renewable resources, and the linear pentadiene is obtained by (1) condensation of lactic acid to produce pentanedione, (2) hydrogenation of pentanedione to produce pentanediol, and (3) dehydration of pentanediol. The present invention prepares linear pentadiene, especially 1,3-pentadiene through the process route of condensation, hydrogenation and dehydration of lactic acid. The invention provides a green and sustainable method for synthesizing linear pentadiene based on the conversion of bio-based chemicals. The method has simple operation, short process, no harsh experimental conditions, easy preparation of raw materials and catalysts, and large scale. Synthetic foreground.

Description

technical field [0001] The invention belongs to the technical field of conversion and synthesis of bio-based chemicals, relates to a method for synthesizing pentanediol and a method for synthesizing linear pentadiene, in particular to a method for synthesizing pentanediol and a method for preparing raw materials based on lactic acid conversion Method for the synthesis of substance-based linear pentadiene. Background technique [0002] Linear diene compounds are widely used in polymer materials, cosmetics, fragrances, pesticides and other fields. Linear pentadiene mainly includes 1,3-pentadiene and 1,4-pentadiene. In addition to being used in the synthesis of polyolefin materials, 1,3-pentadiene is mainly used as a curing agent, such as methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylcyclohexene, tetracarboxylic acid, etc., and can also be used in Synthetic leaf alcohol is used to make fragrances, and 1,3-pentadiene is also used in the productio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/145C07C31/20C07C1/24C07C11/173C07C11/20C07C45/45C07C49/12C07C49/14B01J23/42B01J23/63B01J23/89
CPCC07C29/145C07C1/24C07C45/455B01J23/42B01J23/63B01J23/8926C07C31/20C07C11/173C07C11/20C07C49/12C07C49/14Y02P20/584
Inventor 白晨曦祁彦龙冯瑞林代全权崔龙
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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