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Synthesis method of 3-methyl-2-en-4-yn pentanol through acid ionic liquid catalysis

A technology of acidic ionic liquid and synthesis method, applied in the field of green chemistry, can solve the problems of undisclosed specific methods of catalyst recovery and regeneration, unreachable yield, environmental pollution, etc., and achieve less by-products, simple post-treatment, and high yield. high rate effect

Active Publication Date: 2016-01-27
SHANGYU NHU BIOCHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the catalytic transposition of 3-methyl-1-ene-4-yne-3-pentanol to 3-methyl-2-en-4-ynepentanol is mainly completed by acid catalysis, and the most common one is sulfuric acid As an acid catalyst, the pH is controlled within the range of 2 to 5, but using sulfuric acid as a catalyst will produce a large amount of waste acid water after the reaction is completed, causing serious environmental pollution
[0006] Also have related literature (CN102046571A) to report and be used for catalyzing this reaction with acidic ion exchange resin as acid catalyst in addition, although it is reported in this patent that this type of catalyst can be reused, there is no specific method for disclosing catalyst recovery and regeneration, and If the catalyst is simply filtered, then washed twice with diisopropyl ether and reused, it is found that the yield is greatly reduced, and it is far from the yield recorded in the examples.

Method used

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  • Synthesis method of 3-methyl-2-en-4-yn pentanol through acid ionic liquid catalysis
  • Synthesis method of 3-methyl-2-en-4-yn pentanol through acid ionic liquid catalysis
  • Synthesis method of 3-methyl-2-en-4-yn pentanol through acid ionic liquid catalysis

Examples

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Effect test

Embodiment 1-12

[0049]The synthesis steps of ionic liquid IL1-IL9 are as follows: N-methylimidazole, pyridine, N-methylpyrrole are equal to excess chlorobutane and refluxed in toluene for 48 hours, and the obtained chloride salts are respectively mixed with CH 3 COOK, KHSO 4 , Potassium p-toluenesulfonate, Potassium tetrafluoroborate, Potassium hexafluorophosphate, etc. for ion exchange reaction, the obtained product is filtered and desolubilized, CH 2 Cl 2 The structural formulas of IL1-IL9 and IL13-IL15 obtained by extraction and vacuum drying are as follows:

[0050]

Embodiment 13-15

[0052] The synthesis steps of ionic liquid IL10-IL12 are as follows: N-methyl-2-pyrrolidone, acetic acid, concentrated sulfuric acid, and p-toluenesulfonic acid were heated and reacted for 2 hours at a molar ratio of 1:1, and the product was washed three times with ethyl acetate after cooling , through vacuum drying, the product N-methylpyrrolidone acetate IL10, N-methylpyrrolidone bisulfate IL11, N-methylpyrrolidone p-toluenesulfonate IL12, the structural formula is as follows:

[0053]

Embodiment 16-33

[0055] Embodiment 16-33 has investigated under the action of different catalysts, 3-methyl-1-ene-4-yne-3-pentanol catalytic transposition generates 3-methyl-2-ene-4-ynylpentanol, the steps as follows:

[0056] Add 100g of 98% 3-methyl-1-en-4-yne-3-pentanol, 100ml of water, 100ml and 50g of protonic acid catalyst or ionic liquid in a 500ml flask, and keep the temperature of the material at about 50-60°C. Stir the reaction for 4~6h. GC tracks the progress of the reaction. After the reaction is complete, the reaction system is evacuated and rotary evaporated. The evaporated liquid is separated from the water layer, and the oil layer is washed with saturated Na 2 CO 3 Wash with aqueous solution for 1 to 2 times to obtain the crude product, and then obtain high content of E-3-methyl-2-ene-4-ynylpentanol and Z-3-methyl-2-ene-4-ynylpentanol . The ionic liquid phase is washed with an organic solvent and recycled. The results of each group of reactions are listed in Table 1. In or...

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Abstract

The present invention discloses a synthesis method of 3-methyl-2-en-4-yn pentanol through acid ionic liquid catalysis. The synthesis method comprises that in the presence of water and an acid ionic liquid, 3-methyl-1-en-4-yn-3-pentanol is subjected to an isomerization reaction, and post-treatment is performed after completing the reaction to obtain the 3-methyl-2-en-4-yn pentanol. According to the present invention, with the synthesis method, the defects of the traditional 3-methyl-1-en-4-yn-3-pentanol catalytic translocation process can be overcome, the reaction conditions can be alleviated, the yield of the reaction can be improved, the catalyst circulation application can be achieved, the wastewater production can be reduced, and the environment is effectively improved.

Description

technical field [0001] The invention belongs to the field of green chemistry, and specifically relates to the application of ionic liquids in the catalytic transposition of 3-methyl-1-ene-4-yne-3-pentanol to generate 3-methyl-2-ene-4-ynylpentanol . Background technique [0002] The double bond and substituent migration of allyl compounds is a very common organic reaction, often called allylic rearrangement. Allyl alcohol, especially allyl tertiary alcohol, can undergo isomerization under the action of acid catalysis. The mechanism of this isomerization reaction is the 1,3-migration of hydroxyl group and the corresponding double bond displacement. [0003] In the field of production of vitamins and other related products, the allyl alcohol transposition It has attracted special attention from chemical researchers, mainly because it produces two isomers after rearrangement of allyl alcohol: (Z)-3-methyl-2-ene-4-ynylpentanol (CAS: 6153- 05-5) and (E)-3-methyl-2-en-4-ynylpent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C33/048C07C29/56B01J31/02B01J31/04
Inventor 田金金吴兴华王刚杨舵郑兆祥单国红杨梢烽
Owner SHANGYU NHU BIOCHEM IND
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