The synthetic method of 3-hydroxypropionate

A technology of hydroxypropionate and synthesis method, applied in chemical instruments and methods, carbon monoxide or formate reaction preparation, organic compound/hydride/coordination complex catalyst, etc., can solve the selection of 3-hydroxypropionate It can increase the activity, improve the stability, and improve the conversion rate.

Active Publication Date: 2018-10-23
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The technical problem to be solved by this invention is the low selectivity problem of 3-hydroxypropionate in the prior art, and a kind of synthetic method of new 3-hydroxypropionate is provided, and this method has the selectivity of 3-hydroxypropionate Advantages of high sex

Method used

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  • The synthetic method of 3-hydroxypropionate
  • The synthetic method of 3-hydroxypropionate
  • The synthetic method of 3-hydroxypropionate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] 1. Synthetic Ligand A

[0038]

[0039] Add 1312mg (10mmol) tripropargylamine, 2988mg (36mmol) allyl azide, 250mg (1mmol) copper sulfate hydrate (CuSO 4 ·5H 2 (0), 200mg (1mmol) sodium ascorbate, 40mL tert-butanol and 10mL water, the system was replaced with nitrogen three times, and reacted at 60°C for 24 hours under nitrogen atmosphere. After the reaction was completed, 100 mL of water was added, and the solution was extracted several times with dichloromethane. The organic phases were combined, dried, concentrated, and finally separated by column chromatography to obtain 1900 mg of light yellow solid which was Ligand A.

[0040] 2. Synthesis of methyl 3-hydroxypropionate

[0041] 342mg (1.0mmol) of Co 2 (CO) 8 Dissolve in 740 mmol of methanol, add 3.0 mmol of ligand A, and stir at room temperature for 2 hours. The catalyst solution was transferred to a 100 mL reactor, and the reactor was purged three times with nitrogen, and 50 mmol of ethylene oxide and carb...

Embodiment 2

[0044] 1. Synthetic Ligand B

[0045]

[0046] According to the experimental process of Example 1, with 1312mg (10mmol) tripropargyl amine, 3564mg (36mmol) allyl azide, 375mg (1.5mmol) copper sulfate hydrate (CuSO 4 ·5H 2 O), 300mg (1.5mmol) sodium ascorbate is raw material, synthesizes and obtains 1712mg brown solid and is ligand B.

[0047] 2. Synthesis of methyl 3-hydroxypropionate

[0048] 342mg (1.0mmol) of Co 2 (CO) 8Dissolve in 740 mmol of methanol, add 3.0 mmol of ligand B, and stir at room temperature for 2 hours. The catalyst solution was transferred to a 100 mL reactor, and the reactor was purged three times with nitrogen, and 50 mmol of ethylene oxide and carbon monoxide were added to make the system pressure 4.0 MPa, and the reaction was carried out at 50° C. for 4 hours. The kettle body was fully cooled to 0°C, and the pressure was slowly released to normal pressure. The reactor was purged three times with nitrogen, and the sampling analysis showed that t...

Embodiment 3

[0051] 1. Synthetic Ligand C

[0052]

[0053] According to the experimental process of Example 1, with 1312mg (10mmol) tripropargylamine, 4284mg (36mmol) phenyl azide, 250mg (1mmol) copper sulfate hydrate (CuSO 4 ·5H 2 O), 200mg (1mmol) sodium ascorbate is raw material, synthesizes and obtains 2196mg white solid and is ligand C.

[0054] 2. Synthesis of methyl 3-hydroxypropionate

[0055] 342mg (1.0mmol) of Co 2 (CO) 8 Dissolve in 740 mmol of methanol, add 3.0 mmol of ligand C, and stir at room temperature for 2 hours. The catalyst solution was transferred to a 100 mL reactor, and the reactor was purged three times with nitrogen, and 50 mmol of ethylene oxide and carbon monoxide were added to make the system pressure 4.0 MPa, and the reaction was carried out at 50° C. for 4 hours. The kettle body was fully cooled to 0°C, slowly released to normal pressure, purged the reactor three times with nitrogen, and sampled and analyzed, the results showed that the conversion ra...

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Abstract

The invention relates to a synthesis method of 3-hydroxy propionate. The method mainly solves the problem that the selectivity of the 3-hydroxy propionate in the prior art is low. The synthesis method of the 3-hydroxy propionate comprises the following steps: i, enabling the ligand as shown in the formula (I) to perform the complexing reaction with cobalt carbonyl in a solvent to obtain a catalyst solution, wherein the solvent is the alcohol or the solvent containing the alcohol; R1 to R3 are independently selected from one of alkyl or alkenyl, aryl or substituted aryl, and heterocyclo, and R1 to R3 independently contain 1 to 6 carbon atoms; ii, adding ethylene oxide and carbon monoxide in the catalyst solution, reacting to obtain the 3-hydroxy propionate. The technical scheme well solves the technical problem, and can be used for the industrial production of the 3-hydroxy propionate. The the formula (I) is shown in the description.

Description

technical field [0001] The invention relates to a method for synthesizing 3-hydroxypropionate. Background technique [0002] 1,3-Propanediol is an important organic fine chemical, which can be used as a raw material for the production of antifreeze, plasticizer, preservative and emulsifier, and is also widely used in industries such as food, cosmetics and pharmaceuticals. Its most important The application is to synthesize polytrimethylene terephthalate (PTT) polyester fiber as a monomer. Compared with the commonly used polyethylene terephthalate (PET) fiber, PTT fiber has light resistance, less water absorption, and stable It has excellent properties such as good resistance, and at the same time has the advantages of good resilience, easy biodegradation and little environmental pollution. It has a wide range of application prospects and is the focus of current research and development. [0003] 3-Hydroxypropionate is an important intermediate in the synthesis of 1,3-propan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/37C07C69/675B01J31/22C07D401/14
CPCB01J31/1815B01J2531/0219B01J2531/0238C07C67/37C07D401/14C07C69/675
Inventor 刘波吕建刚金照生李晓明周海春
Owner CHINA PETROLEUM & CHEM CORP
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