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Preparation method of 1-(2-furyl)-2-propyne-1-ol

A technology of acetylene alcohol and furfuryl, which is applied in the field of chemical synthesis, can solve the problems that the catalyst cannot be used mechanically, the product yield is reduced, and the feasibility is low, so as to avoid a large amount of basic magnesium chloride waste salt and reduce the cost of raw and auxiliary materials

Active Publication Date: 2019-02-26
SHANDONG NHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Eur.J.Org.Chem. 2014,4663-4670 discloses furfural and acetylene in Bu 4 NOH / H 2 In the O / DMSO catalytic system, furfuryl acetylene alcohol was synthesized by reaction at 5±2°C. Although the yield was 86%, in this system, the amount of solvent DMSO was 33.7 times (mass fraction) that of the raw material, and the product was produced by Purified by column chromatography, without involving other purification methods, the feasibility in production is very low
[0011] (2) The catalyst cannot be applied mechanically, or the product yield will decrease significantly after applying it mechanically

Method used

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  • Preparation method of 1-(2-furyl)-2-propyne-1-ol
  • Preparation method of 1-(2-furyl)-2-propyne-1-ol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1 A kind of preparation method of furfuryl acetylene alcohol

[0048] Include the following steps:

[0049] (1) Add catalyst

[0050] The aqueous solution of reaction catalyst 18-crown (ether)-6 and KBr is added in the reactor; wherein 18-crown (ether)-6 2.77g (0.01mol), KBr1.39g (0.012mol), water 39.56g (2.2mol ).

[0051] (2) Add acetylene solution

[0052] Add compressed and cooled liquefied acetylene solution to the reactor; control the temperature of the reactor to 5-10°C and the pressure to 0.5MPa;

[0053] The acetylene solution is a mixed solution of acetylene and methylamine, wherein the mass of methylamine is 3514.03g (113.14mol), and the mass of acetylene is 327.34g (12.57mol).

[0054] (3) Add furfural solution

[0055] The plunger pump will add the furfural solution of the reaction raw material into the reaction in about 5 minutes, and continue to keep warm for 5 minutes;

[0056] The furfural solution is a mixture of furfural and xylene, w...

Embodiment 2

[0063] Embodiment 2 A kind of preparation method of furfuryl acetylene alcohol

[0064] Include the following steps:

[0065] (1) Add catalyst

[0066] Add the reaction catalyst 18-crown (ether)-6 and the aqueous solution of KBr to the reaction kettle, wherein KBr1.17g (0.01mol), 18-crown (ether)-6 3.39g (0.01mol), water 56.51g (3.14mol ).

[0067] (2) Add acetylene solution

[0068] Add the compressed and cooled liquefied acetylene solution to the reactor, and control the temperature of the reactor to 25-30°C and the pressure to 1MPa;

[0069] The acetylene solution is a mixed solution of acetylene and methylamine, the quality of methylamine is 1859.2g (59.86mol), and the quality of acetylene is 222.67g (8.55mol).

[0070] (3) Add furfural solution

[0071] Use a high-pressure plunger pump to add the furfural solution of the reaction raw material into the reaction kettle in about 5 minutes, and continue to keep warm for 22 minutes.

[0072] The furfural solution is a mi...

Embodiment 3

[0079] Embodiment 3 A kind of preparation method of furfuryl acetylene alcohol

[0080] Include the following steps:

[0081] (1) Add catalyst

[0082] Add the reaction catalyst 15-crown (ether)-5 and the aqueous solution of NaI to the reaction kettle; wherein NaI2.11g (0.014mol), 15-crown (ether)-5 2.78g (0.01mol), water 55.68g (3.09mol ).

[0083] (2) Add acetylene solution

[0084] Add compressed and cooled liquefied acetylene solution into the reactor, control the temperature of the reactor to 5-10°C, and the pressure to 1.5MPa;

[0085] The acetylene solution is a mixed solution of acetylene and methylamine, wherein the mass of methylamine is 1177.75g (37.92mol), and the mass of acetylene is 109.71g (4.21mol).

[0086] (3) Add furfural solution

[0087] Use a high-pressure plunger pump to feed the furfural solution of the reaction raw material; add the reaction in about 5 minutes, and continue to keep warm for 17 minutes.

[0088] The furfural solution is a mixture ...

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Abstract

The invention provides a preparation method of 1-(2-furyl)-2-propyne-1-ol. Raw materials are acetylene and furfural; a catalyst is a composite catalyst formed by crown ether and alkali metal salt. Water and methylbenzene / ethylbenzene / xylene are used as solvents and combined with the specific catalyst and other reaction conditions, the raw material conversion rate is 85%-95%, and the product yieldis 87.7%-93.5%; layered recycling and reuse of the catalyst after flash evaporation are realized on the premise that the reaction yield is increased, the reaction and reuse yield is not decreased obviously, the reaction conversion rate is 83%-95% and the reaction yield is 86%-92% after continuous reuse in eight batches; the dosage of solvents is reduced.

Description

technical field [0001] The invention discloses a preparation method of 1-(2-furyl)-2-propyn-1-ol, an important intermediate of ethyl maltol, and belongs to the technical field of chemical synthesis. Background technique [0002] Ethyl maltol is an ideal food additive that is safe, non-toxic, widely used, effective, and used in a very small amount. Efficacy agent, which has a significant effect on improving and enhancing the flavor of food, sweetens sweets, and has antibacterial and antiseptic properties, which can prolong the storage period of food. Ethyl maltol is a white crystalline powder with a fragrant aroma. No matter it is crystal or powder, it will keep its sweet fragrance after being dissolved in the solution, and the solution is relatively stable. [0003] The chemical name of ethyl maltol is: 2-ethyl-3-hydroxy-4H-pyrone (3-hydroxy-2-methyl [0004] -4H-pyran-4-one) It is a white needle-like or white crystalline powder, melting point 89 ~ 93 ℃, easily soluble in...

Claims

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Application Information

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IPC IPC(8): C07D307/42
CPCC07D307/42Y02P20/584
Inventor 马啸朱全东张相如鲁光银何博李传鹏田路飞郭金博于明黄珊珊
Owner SHANDONG NHU PHARMA
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