1,4-dihydro-3,5-lauryl alcohol ester diacetate-2,6-dimethyl pyridine synthesis method

A technology of lutidine and a synthesis method, which is applied in the field of 1,4-dihydropyridine derivative synthesis, can solve the problems of large environmental pollution, low reaction yield and product purity, and is difficult to store, and achieves reduction of production cost, The effect of high reaction yield and product purity

Active Publication Date: 2018-07-20
CHANGZHOU YONGHE FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The disadvantages of this method are: (1) diketene has a strong lachrymatory property, and is extremely volatile and difficult to store
(2) The reaction yield and product purity are low
(3) A large amount of amine-containing wastewater will be produced, which will pollute the environment and is not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0019] The DHP synthesis method of the present embodiment has the following steps:

[0020] ①Add 400kg lauryl alcohol and 1000kg methyl acetoacetate into the reaction kettle, stir and raise the temperature to 160±5°C, and keep it warm at this temperature until the reaction is complete, and recover the methanol generated during the reaction.

[0021] After the reaction, the reaction system was first cooled to 90±5°C, then the excess methyl acetoacetate was evaporated under reduced pressure, and then the temperature was lowered to below 60°C to obtain 558kg of orange-brown transparent liquid, which was ready for use. The distilled methyl acetoacetate is recycled to the next batch.

[0022] ②Add 120kg of water, 100kg of methanol (50kg of which comes from the methanol recovered in step ①), 165.6kg of urotropine, 45.6kg of ammonium acetate and 558kg of orange-brown transparent liquid obtained in step ① into the reactor in turn, and then heat up to reflux Insulate the reaction unti...

Embodiment 2～ Embodiment 5）

[0025] The DHP synthesis method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0026] Table 1

[0027]

Embodiment 6）

[0029] The step of the DHP synthetic method of the present embodiment 1. is with embodiment 1, and step 2. is as follows:

[0030] Add 40kg of water, 165kg of methanol (50kg of which comes from the methanol recovered in step ①), 90.3kg of formaldehyde, 210.0kg of ammonium acetate and 558kg of orange-brown transparent liquid obtained in step ① into the reaction kettle in turn, and then heat up to reflux and keep warm until the reaction is complete .

[0031] After the reaction, cool down to 65-70°C, first add 500kg of water, then add 1200kg of toluene, stir and let it stand, cool the organic phase to 30°C, suction filter, centrifuge, and dry to obtain 525kg of light yellow DHP. The purity was 98.2% (HPLC), and the two-step total yield was 91.6%.

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Abstract

The invention discloses a 1,4-dihydro-3,5-lauryl alcohol ester diacetate-2,6-dimethyl pyridine synthesis method. The 1,4-dihydro-3,5-lauryl alcohol ester diacetate-2,6-dimethyl pyridine synthesis method comprises the following specific steps: 1, enabling lauryl alcohol and methyl acetoacetate to react to obtain n-dodecyl acetoacetate; 2, enabling the n-dodecyl acetoacetate to react with urotropinor formaldehyde and ammonium acetate to obtain the 1,4-dihydro-3,5-lauryl alcohol ester diacetate-2,6-dimethyl pyridine. The synthesis method uses the lauryl alcohol and the methyl acetoacetate to react to obtain the n-dodecyl acetoacetate, the production of amine wastewater is avoided compared with the reaction between the laurinol and ketene dimer, so that the synthesis method is a green production process, the problem of instability of the reaction material is also solved, and particularly, the synthesis method is higher in reaction yield and production purity and is suitable for industrialproduction.

Description

technical field [0001] The invention belongs to the technical field of synthesis of 1,4-dihydropyridine derivatives, and in particular relates to a synthesis method of 1,4-dihydro-3,5-diacetate lauryl-2,6-lutidine. Background technique [0002] 1,4-dihydro-3,5-diacetate lauryl-2,6-lutidine (also known as 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate Didodecanyl acid, CAS No. 36265-41-5, molecular formula C 33 h 59 NO 4 ) is an antioxidant with excellent performance, mainly used in PVC, PE and other plastics. [0003] At present, the method of synthesizing the compound is to first react lauryl alcohol (also known as lauryl alcohol) with diketene in the presence of amine catalysts to obtain n-dodecyl acetoacetate, and then react with urotropine or formaldehyde and amines Substances (ammonia / ammonium acetate / ammonium bicarbonate, etc.) are reacted. [0004] The disadvantages of this method are: (1) diketene has a strong lachrymatory property, and is extremely volatile...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/90
CPCC07D211/90Y02P20/582
Inventor 姜友林许晓春栾永勤陆海峰万海阳严明亮
Owner CHANGZHOU YONGHE FINE CHEM
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