CN102702169B - Method for preparing light stabilizer 3-dodecyl-1(1,2,2,6,6-pentamethyl piperidyl)-2,5-dipyrrolidone - Google Patents

Method for preparing light stabilizer 3-dodecyl-1(1,2,2,6,6-pentamethyl piperidyl)-2,5-dipyrrolidone Download PDF

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CN102702169B
CN102702169B CN 201210202394 CN201210202394A CN102702169B CN 102702169 B CN102702169 B CN 102702169B CN 201210202394 CN201210202394 CN 201210202394 CN 201210202394 A CN201210202394 A CN 201210202394A CN 102702169 B CN102702169 B CN 102702169B
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dodecyl
pentamethyl
piperidyl
pyrroles
photostabilizer
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CN102702169A (en
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王树清
王歆然
孙冬兵
杜承贤
田新荣
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Nantong Huikang International Trade Co. Ltd.
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Nantong Huikang International Enterprise Co Ltd
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Abstract

The invention discloses a method for preparing a light stabilizer 3-dodecyl-1(1,2,2,6,6-pentamethyl piperidyl)-2,5-dipyrrolidone. The method comprises the following step of: reacting 1,2,2,6,6-pentamethyl piperidyl amine and dodecyl succinic anhydride serving as raw materials in the presence of a catalyst and a solvent to obtain the 3-dodecyl-1(1,2,2,6,6-pentamethyl piperidyl)-2,5-dipyrrolidone. The 3-dodecyl-1(1,2,2,6,6-pentamethyl piperidyl)-2,5-dipyrrolidone is synthesized, the separation and purification processes are simple, reaction time is short, the yield of the product is over 92 percent, the purity of the product is high, energy consumption is low, environmental pollution is light, cost is low, and the method is an ideal process for implementing industrial production.

Description

Photostabilizer 3-dodecyl-1-(1,2,2,6,6-pentamethyl-piperidyl)-pyrroles-2, the preparation method of 5-dioxane ketone
Technical field
The present invention relates to a kind of photostabilizer 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-pyrroles-2, the preparation method of 5-dioxane ketone.
Background technology
3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-pyrroles-2,5-dioxane ketone is the hindered amine type light stabilizer of lower molecular weight high-efficiency low-toxicity, product is not volatile during high temperature process.Good with most industry solvent phase dissolubility, have superior polymer intermiscibility, be applicable to the polyethylene flat filament, injection moulding and rotational moulding, sheet material; Polypropylene screen, flat filament, injection moulding, polyoxymethylene, ASA, ABS, HIPS, SAN, PVC is hard, soft goods, and the goods such as PMMA and PUR are specially adapted to liquid color enriched material.It and resin have good consistency and dispersiveness.Its molecular formula is C 26H 48N 2O 2, molecular weight is 420.64, molecular structural formula:
Its outward appearance is liquid of vicidity, though 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-pyrroles-2,5-dioxane ketone has application, but the report of relevant its synthetic method is few, and we are with reference to the theory of organic synthesis, adopt dodecyl succinic anhydride and 1,2,2,6,6-pentamethyl-piperylhydrazine is raw material, and ammonium molybdate is that catalyzer has synthesized 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, experimental result shows, it is fast that the method has speed of response, and the reaction times is short, the reaction preference advantages of higher.
Summary of the invention
The objective of the invention is in order to overcome above deficiency, provide the high 3-dodecyl-1 of a kind of product yield (1,2,2,6,6-pentamethyl-piperidyl)-pyrroles-2, the preparation method of 5-dioxane ketone.
The present invention is achieved through the following technical solutions: a kind of photostabilizer 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2, the preparation method of 5-dioxane ketone, with 1,2,2,6,6-pentamethyl-piperylhydrazine, dodecyl succinic anhydride is raw material, carries out condensation reaction under the condition that catalysts and solvents exists, described 1,2,2,6,6-pentamethyl-piperylhydrazine, dodecyl succinic anhydride, the usage ratio of catalysts and solvents is 1:1.58-4.73:0.01-0.11:1.75-5.87 by mass, and temperature of reaction is 110-125 ℃, reaction times is 3-6h, and stopped reaction adds 1,2,2,6, the water that 6-pentamethyl-piperylhydrazine total mass is 2.35 times, wash, the mixed solution after the washing carries out reflux and divides water, activated carbon decolorizing, filter, desolvation namely gets photostabilizer 3-dodecyl-1 (1,2 again, 2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone.
Further improvement of the present invention is: described catalyzer is ammonium molybdate or Sodium orthomolybdate or potassium molybdate, preferred ammonium molybdate.
Further improvement of the present invention is: described solvent is sherwood oil or normal hexane or normal heptane, preferred sherwood oil.
The present invention compared with prior art has the following advantages: the present invention synthesizes 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, the separating-purifying process is simple, reaction times is short, and product yield reaches more than 92%, and product purity is higher, less energy consumption, environmental pollution is little, and cost is low, is the comparatively ideal technique that realizes suitability for industrialized production.
Embodiment:
In order to deepen the understanding of the present invention, the invention will be further described below in conjunction with embodiment, and following examples only are used for explaining the present invention, do not consist of the restriction to protection domain of the present invention.
The present invention shows a kind of photostabilizer 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2, the preparation method's of 5-dioxane ketone embodiment, with 1,2,2,6,6-pentamethyl-piperylhydrazine, dodecyl succinic anhydride is raw material, carries out condensation reaction under the condition that catalysts and solvents exists, described 1,2,2,6,6-pentamethyl-piperylhydrazine, dodecyl succinic anhydride, the usage ratio of catalysts and solvents is 1:1.58-4.73:0.01-0.11:1.75-5.87 by mass, and temperature of reaction is 110-125 ℃, reaction times is 3-6h, and stopped reaction adds 1,2,2,6, the water that 6-pentamethyl-piperylhydrazine total mass is 2.35 times, wash, the rear mixed solution of washing carries out reflux and divides water, activated carbon decolorizing, filter, desolvation namely gets photostabilizer 3-dodecyl-1 (1,2 again, 2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone.Catalyzer is ammonium molybdate or Sodium orthomolybdate or potassium molybdate, and the preferred ammonium molybdate of catalyzer of the present invention, solvent are sherwood oil or normal hexane or normal heptane, the preferred sherwood oil of solvent of the present invention.
Embodiment 1:
In the four-hole reaction flask of electric mixer, reflux exchanger and thermometer is housed, add successively 1,2,2,6,6-pentamethyl-piperylhydrazine 17.0g, dodecyl succinic anhydride 40.2g, catalyzer 0.4g, solvent 50g starts agitator, during 110-125 ℃ of temperature of control, control reaction times 3-8h is behind the stopped reaction, the water that adds 40g is washed, reflux is divided water, and activated carbon decolorizing filters, desolvation again, namely get photostabilizer 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, product yield reaches 92.46%.
Embodiment 2:
In the four-hole reaction flask of electric mixer, reflux exchanger and thermometer is housed, add successively 1,2,2,6,6-pentamethyl-piperylhydrazine 17.0g, dodecyl succinic anhydride 53.7g, catalyzer 0.4g, solvent 50g starts agitator, during 110-125 ℃ of temperature of control, control reaction times 3-6h is behind the stopped reaction, the water that adds 40g is washed, reflux is divided water, and activated carbon decolorizing filters, desolvation again, namely get photostabilizer 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, product yield reaches 92.83%.
Embodiment 3:
In the four-hole reaction flask of electric mixer, reflux exchanger and thermometer is housed, add successively 1,2,2,6,6-pentamethyl-piperylhydrazine 17.0g, dodecyl succinic anhydride 32.2g, catalyzer 1.0g, solvent 50g starts agitator, during 110-125 ℃ of temperature of control, control reaction times 3-6h is behind the stopped reaction, the water that adds 40g is washed, reflux is divided water, and activated carbon decolorizing filters, desolvation again, namely get photostabilizer 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, product yield reaches 92.11%.
Embodiment 4:
In the four-hole reaction flask of electric mixer, reflux exchanger and thermometer is housed, add successively 1,2,2,6,6-pentamethyl-piperylhydrazine 17.0g, dodecyl succinic anhydride 67.1g, catalyzer 0.4g, solvent 50g starts agitator, during 110-125 ℃ of temperature of control, control reaction times 3-6h is behind the stopped reaction, the water that adds 40g is washed, reflux is divided water, and activated carbon decolorizing filters, desolvation again, namely get photostabilizer 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, product yield reaches 93.09%.
Embodiment 5:
In the four-hole reaction flask of electric mixer, reflux exchanger and thermometer is housed, add successively 1,2,2,6,6-pentamethyl-piperylhydrazine 17.0g, dodecyl succinic anhydride 48.3g, catalyzer 0.6g, solvent 70g starts agitator, during 110-125 ℃ of temperature of control, control reaction times 3-6h is behind the stopped reaction, the water that adds 40g is washed, reflux is divided water, and activated carbon decolorizing filters, desolvation again, namely get photostabilizer 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, product yield reaches 92.74%.
The present invention synthesizes 3-dodecyl-1 (1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, the separating-purifying process is simple, reaction times is short, and product yield reaches more than 92%, and product purity is higher, less energy consumption, environmental pollution is little, and cost is low, is the comparatively ideal technique that realizes suitability for industrialized production.

Claims (5)

1. photostabilizer 3-dodecyl-1-(1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2, the preparation method of 5-dioxane ketone, it is characterized in that: with 1,2,2,6,6-pentamethyl-piperylhydrazine, dodecyl succinic anhydride is raw material, carries out amination reaction and prepare 3-dodecyl-1-(1 in the presence of catalysts and solvents, 2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone, described catalyzer are ammonium molybdate or Sodium orthomolybdate or potassium molybdate, the temperature of described amination reaction is 110-125 ℃, and the time of amination reaction is 3-6h, after reaction finishes, add 1,2,2, the water that 6,6-pentamethyl-piperylhydrazine total mass is 2.35 times is washed, mixing solutions after the washing carries out reflux and divides water, decolour with gac, after the filtration, desolvation again, namely get photostabilizer 3-dodecyl-1-(1,2,2,6,6-pentamethyl-piperidyl)-and pyrroles-2,5-dioxane ketone.
2. photostabilizer 3-dodecyl-1-(1,2,2 according to claim 1,6,6-pentamethyl-piperidyl)-and pyrroles-2, the preparation method of 5-dioxane ketone, it is characterized in that: 1,2,2,6, the usage ratio of 6-pentamethyl-piperylhydrazine, dodecyl succinic anhydride, catalyzer, solvent is by mass: 1,2,2,6,6-pentamethyl-piperylhydrazine: dodecyl succinic anhydride: catalyzer: solvent=1:1.58-4.73:0.01-0.11:1.75-5.87.
3. photostabilizer 3-dodecyl-1-according to claim 1 and 2 (1,2,2,6,6-pentamethyl-piperidyl)-pyrroles-2, the preparation method of 5-dioxane ketone is characterized in that: described catalyzer is ammonium molybdate.
4. photostabilizer 3-dodecyl-1-according to claim 1 and 2 (1,2,2,6,6-pentamethyl-piperidyl)-pyrroles-2, the preparation method of 5-dioxane ketone is characterized in that: described solvent is sherwood oil or normal hexane or normal heptane.
5. photostabilizer 3-dodecyl-1-according to claim 4 (1,2,2,6,6-pentamethyl-piperidyl)-pyrroles-2, the preparation method of 5-dioxane ketone is characterized in that: described solvent is sherwood oil.
CN 201210202394 2012-06-19 2012-06-19 Method for preparing light stabilizer 3-dodecyl-1(1,2,2,6,6-pentamethyl piperidyl)-2,5-dipyrrolidone Expired - Fee Related CN102702169B (en)

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JPH0717759B2 (en) * 1986-07-28 1995-03-01 旭電化工業株式会社 Propylene resin molded product
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