Preparation method of 5-norborn-2-enyl methyl chloroacetate
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A technology of norbornene methyl ester, applied in the field of preparation of norbornene methyl chloroacetate, can solve the problem of wasting raw materials
Inactive Publication Date: 2014-01-01
NANKAI UNIV
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[0002] At present, the by-product C in the petrochemical production process 5 The distillate has not been rationally utilized so far, and it is mainly burned as fuel, wasting a lot of precious raw materials, which is a pity
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Embodiment 1
[0023] A preparation method of norbornene methyl chloroacetate, the steps are as follows:
[0024] 1) Take 2.5mL (18.6mmol) of dicyclopentadiene and 3.0mL (44.1mmol) of allyl alcohol, add it to a 10mL tubular reactor, freeze it with liquid nitrogen until it is completely solidified, and then slowly melt it with nitrogen gas , repeat this cycle step 2 times to completely remove the air that may be dissolved in it, then freeze until solidified, vacuumize to 339Pa and seal the tube;
[0025] 2) Put the sealed tube into a constant temperature oil bath, slowly heat up to 150°C and react for 8 hours, then transfer the product in the tube into a round bottom flask, and distill under reduced pressure to 399Pa at room temperature to evaporate excess allyl in the system Alcohol, and then under reduced pressure, slowly warming up to 89 ° C, the collected fractions of colorless liquid is 5-hydroxymethyl-2-norbornene (NBCH 2 OH);
[0026] 3) Add 10mL of pure α-chloroacetyl chloride, 15mL...
Embodiment 2
[0030] A preparation method of norbornene methyl chloroacetate, the steps are as follows:
[0031] 1) Take 2.5mL (18.6mmol) of dicyclopentadiene and 3.0mL (44.1mmol) of allyl alcohol, add it to a 50mL reactor, freeze it with liquid nitrogen until it is completely solidified, then slowly melt it with nitrogen gas, repeat This cycle step is 3 times to completely remove the air that may be dissolved therein, then freeze until solidified, and then close the reactor after vacuuming to 339Pa;
[0032] 2) Put the reactor into a constant temperature oil bath, slowly heat up to 190°C and react for 10 hours, then transfer the product in the reactor into a round bottom flask, reduce the pressure to 399Pa at room temperature and distill off the excess olefin in the system Propanol, under reduced pressure, then slowly warming up to 89 ° C, the collected fractions are colorless liquids that are 5-hydroxymethyl-2-norbornene (NBCH 2 OH);
[0033] 3) Add 10mL of pure α-chloroacetyl chloride,...
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Abstract
A preparation method of 5-norborn-2-enyl methyl chloroacetate comprises the following steps: 1, repeatedly carrying out liquid nitrogen cooling solidification and nitrogen introduction thawing in a reactor to remove dissolved air; 2, heating the reactor for a reaction, and carrying out reduced pressure distillation for steaming out excess allyl alcohol to obtain 5-hydroxymethyl-2-norbornene; 3, adding alpha-chloroacetyl chloride, N,N-dimethylaniline and acetone, and adding 5-hydroxymethyl-2-norbornene in nitrogen in a dropwise manner under stirring for a reaction; and 4, sequentially washing with dilute hydrochloric acid, a saturated sodium carbonate solution and distilled water, allowing to stand, separating an oil layer, carrying out reduced pressure fractionation, and collecting a 115-120DEG C fraction to prepare the 5-norborn-2-enyl methyl chloroacetate. The preparation method has the advantages of simple technology, simple operation, easy implementation, and high product purity, and the 5-norborn-2-enyl methyl chloroacetate can be used as high-molecular benzylation reagent synthesis monomer and an atom transfer radical polymerization reaction initiator.
Description
technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of norbornene methyl chloroacetate. Background technique [0002] At present, the by-product C in the petrochemical production process 5 The distillate has not been rationally utilized so far, and is mainly burned as fuel, wasting a lot of valuable raw materials, which is a pity. C 5 The distillate contains 15-17% cyclopentadiene and dicyclopentadiene, which can be used to synthesize polymer materials with excellent properties. It is the latest progress in the field of polymer synthesis in recent years to synthesize cycloalkene-based macromonomers from cycloolefins as starting materials through living anionic polymerization, and then to synthesize copolymers through living ring-opening disproportionation polymerization (ROMP). However, living anionic polymerization is quite demanding on operating techniques, while the atom transfer radical liv...
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