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Synthesizing method of oriental fruit moth sex pheromone 8(Z/E)-dodecylene-1-alcohol acetate

A technology of pear borer pheromone and dodecene, which is applied in the field of chemical synthesis of insect sex pheromones, can solve the problems of difficult acquisition of raw materials and solvents, easy residue, harsh reaction conditions, etc., and achieve high activity of attracting small borer worms , High product yield and easy access to raw materials

Inactive Publication Date: 2010-12-08
PHEROBIO TECHNOLOGY CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the preparation of DMSO sodium salt requires a certain temperature, it is difficult to control during the operation, it is very easy to explode, and it is very easy to generate sulfur-containing by-products that remain in the target product
[0014] There are many reports on the synthesis of sex pheromones of the pear borer moth, but most of them have the disadvantages that raw materials and solvents are not easy to obtain, the route is too long, the reaction conditions are harsh, and the total yield is low. In addition, at present, the Witting reaction is used to prepare the pear borer moth. The method of sex pheromone intermediate 8(Z / E)-dodecen-1-alcohol, all will utilize DMSO sodium salt in the reaction process, this method easily remains sulfur-containing by-products, and the reaction is difficult to control
Therefore, there is currently no suitable method for the large-scale preparation of 8(Z / E)-dodecen-1-ol

Method used

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  • Synthesizing method of oriental fruit moth sex pheromone 8(Z/E)-dodecylene-1-alcohol acetate
  • Synthesizing method of oriental fruit moth sex pheromone 8(Z/E)-dodecylene-1-alcohol acetate
  • Synthesizing method of oriental fruit moth sex pheromone 8(Z/E)-dodecylene-1-alcohol acetate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Under nitrogen protection, 5kg (10.64moL) 8-hydroxyoctyltriphenylphosphine salt dissolved in 7.5L organic solvent (2.5L DMF and 5L toluene) was cooled to 0°C in the reactor, and 415g (10.64moL )NaNH 2 Add to the reaction kettle in batches, and continue to react for 30 minutes after the dropwise addition to make it fully react; take 510g (12.75moL) NaH (content 60%) and add it to the reaction kettle in batches, stir until the system is dark red, slowly add 770g (10.68moL) ) with the n-butyraldehyde diluted with 7.5L organic solvent (2.5L DMF and 5L toluene), the dropwise addition is completed, and the reaction is continued until the crimson color fades away, and the reaction ends. Pour the reaction solution into ice water to inactivate, adjust the pH to neutral with hydrochloric acid, extract with hexane, dry, concentrate the organic phase, and distill the crude product under reduced pressure to obtain the target product 8(Z / E)-dodecen-1-ol 1.8kg, this step yield is 92%...

Embodiment 2

[0036] Under nitrogen protection, 5kg (10.64moL) 8-hydroxyoctyltriphenylphosphine salt dissolved in 10L organic solvent (2.5L DMF and 7.5L benzene) was cooled to 0°C in the reactor, and 415g (10.64moL )NaNH 2Add to the reaction kettle in batches, and continue to react for 60 minutes after the dropwise addition to make it fully react; take 640g (16moL) NaH (content 60%) and add it to the reaction kettle in batches, stir until the system appears dark red, slowly add 840g (11.65moL) With n-butyraldehyde diluted with 10L organic solvent (2.5L DMF and 7.5L toluene), the dropwise addition is completed, and the reaction is continued until the crimson color fades, and the reaction ends. Pour the reaction solution into ice water to inactivate, adjust the pH to neutral with hydrochloric acid, extract with hexane, dry, concentrate the organic phase, and distill the crude product under reduced pressure to obtain the target product 8(Z / E)-dodecen-1-ol 1.82kg, this step yield is 93%. Acco...

Embodiment 3

[0039] Under the protection of argon, weigh 498g (12.76moL) NaNH 2 Add 6kg (12.76moL) 8-hydroxyoctyltriphenylphosphine salt dissolved in 15L organic solvent (3L DMF and 12L hexane) in batches to the reactor, control the temperature not to exceed 15°C, and react for 1h. Take 1.02kg (25.5moL) NaH (content 60%) and continue to add it to the above reaction kettle in batches to disperse it, stir until the system turns dark red, then cool the reaction solution to -15°C, and slowly add 1.1kg (15.26 mol) dilute n-butyraldehyde with 15L organic solvent (3L DMF and 12L hexane), after the dropwise addition is complete, continue to maintain the reaction until the deep red color fades, and the reaction ends. Pour the reaction solution into ice water to inactivate, adjust the pH to neutral with hydrochloric acid, extract with hexane, dry, concentrate the organic phase, and distill the crude product under reduced pressure to obtain the target product 8(Z / E)-dodecen-1-ol 2.176kg, this step y...

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Abstract

The invention relates to the field of chemical synthesis of inset sex pheromone, in particular to a synthesizing method of oriental fruit moth sex pheromone 8(Z / E)-dodecylene-1-alcohol acetate. The method comprises the following steps of: reacting 8-hydroxy octyl triphenylphosphine salt with strong base to generate corresponding sodium alcoholate salt; continuously reacting the sodium alcoholate salt with the strong base to generate ylide reagent; performing Witting reaction on the ylide reagent with n-butanal under the action of mixed solvent of large-polar solvent and small-polar solvent to obtain the important midbody 8(Z / E)-dodecylene-1-alcohol of inset sex pheromone, and then acetylizing to obtain the 8(Z / E)-dodecylene-1-alcohol acetate. The synthesizing method has easily obtained materials, simple operation, common-use solvent, good selectivity and high activity for inducing inset sex pheromone, and the proportion of Z / E-8-dodecylene-1-alcohol acetate is as high as 95:5. The invention is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis of insect sex pheromones, in particular, the invention relates to a synthesis method of the sex pheromone 8(Z / E)-dodecen-1-ol acetate of the pear borer moth. Background technique [0002] Grapholitha molesta is a worldwide fruit tree pest, also known as pear moth, oriental fruit beetle, referred to as pear molesta, which mainly damages pears, apples, peaches, hawthorns, apricots, cherries and other fruit trees. For many years, chemical pesticides have been the main method of controlling pear borer-eating insects, and their drug resistance develops rapidly and causes serious environmental pollution. The sex pheromone of the pear borer has the advantages of high activity, non-toxicity, strong specificity, convenient use, and no harm to natural enemies. It has a good luring effect on the pear borer and is an effective biological control method. The research on pheromones for pest control is attract...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/08
Inventor 孙凤霞崔艮中马四国刘翠微
Owner PHEROBIO TECHNOLOGY CO LTD
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