CN102659767A - Preparation method for light stabilizer and intermediate 4-glycidyl-1,2,2,6,6-pentamethylpeperidine - Google Patents
Preparation method for light stabilizer and intermediate 4-glycidyl-1,2,2,6,6-pentamethylpeperidine Download PDFInfo
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- CN102659767A CN102659767A CN2012101470715A CN201210147071A CN102659767A CN 102659767 A CN102659767 A CN 102659767A CN 2012101470715 A CN2012101470715 A CN 2012101470715A CN 201210147071 A CN201210147071 A CN 201210147071A CN 102659767 A CN102659767 A CN 102659767A
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- pentamethyl
- piperidines
- photostabilizer
- epoxypropyl
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Abstract
The invention discloses a preparation method for a light stabilizer and an intermediate 4-glycidyl-1,2,2,6,6-pentamethylpeperidine. 4-allyloxy-1,2,2,6,6-pentamethylpeperidine, hypohalous acid and alkali are taken as raw materials, and the light stabilizer and the intermediate 4-glycidyl-1,2,2,6,6-pentamethylpeperidine are prepared in the presence of a catalyst. The light stabilizer and the intermediate 4-glycidyl-1,2,2,6,6-pentamethylpeperidine are prepared from the 4-allyloxy-1,2,2,6,6-pentamethylpeperidine, hypohalous acid and alkali, the separation and purification processes are simple, the reaction time is short, the product yield is high, which is more than 90 percent, the cost is low, and the method is an ideal process for industrial production.
Description
Technical field
The present invention relates to a kind of photostabilizer and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines.
Background technology
Photostabilizer and midbody 4-epoxypropyl-1,2,2,6,6-pentamethyl-piperidines is novel hindered amine light stabilizer, can prolong the duration of service that various plastic cement and coating shine out of doors.In use, the course of processing, can not produce smell with polymer, can not influence the original color of material yet.Also can be used as the midbody of photostabilizer, the compound that contains the structure of hindered amine that can the synthetic macromolecule amount.4-epoxypropyl-1,2,2,6,6-pentamethyl-piperidines and most of industrial solvent intermiscibility are good, have superior polymer intermiscibility, in order to prevent the destruction of UV-light, solve the degradation problem under the sun exposure with photostabilizer.Concerning the polymkeric substance of the easy photodegradation of great majority, hindered amine light stabilizer is a kind of stablizer efficiently.Because the regeneration characteristics of photostabilizer and the low-molecular-weight stablizer characteristics of typicalness make the hindered amines stablizer can have the light and heat stability of long duration, can be used for Vilaterm, Vestolen PP 7052, industrial coating etc., its light stabilising effect is good.Its molecular formula is C
13H
25NO
2, molecular weight: 227.3, molecular structural formula:
Outward appearance is colourless or light yellow thick liquid, boiling point>350.
Because the raw material 4-allyloxy-1,2,2,6 that adopts, 6-pentamethyl-piperidines is difficult for directly carrying out epoxidation reaction, must adopt other method.Photostabilizer and midbody 4-epoxypropyl-1,2,2,6, the compound method of 6-pentamethyl-piperidines is a 4-allyloxy-1; 2,2,6,6-pentamethyl-piperidines and hypochlorous acid carry out two key addition reactions, generate 4-(2 '-chloro-propyl alcohol) base-1; 2,2,6,6-pentamethyl-piperidines, intermediate generate 4-epoxypropyl-1 with alkali reaction again; 2,2,6,6-pentamethyl-piperidines.
Summary of the invention
The object of the present invention is to provide high photostabilizer of a kind of product yield and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines.
Technical solution of the present invention is:
A kind of photostabilizer and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines, present method adopts 4-allyloxy-1; 2,2,6,6-pentamethyl-piperidines, hypohalous acid carry out hypohalous acid prepared in reaction 4-(2 '-chloro-hydroxypropyl)-1,2 in the presence of catalyzer; 2,6,6-pentamethyl-piperidines, after reaction was accomplished, the reaction solution standing demix fell moisture; In remaining mixed solution, add alkali, make it carry out de-hydrogen halide, reaction is filtered after finishing, and the material after the filtration is used SX, tells organic layer; Get organic phase, organic phase is carried out reflux divide water, decolour, filter, after the filtration mixed solution is heated, make the solvent release mixed solution with gac; Promptly get photostabilizer and midbody 4-epoxypropyl-1,2,2,6,6-pentamethyl-piperidines; Wherein, 4-allyloxy-1,2,2,6; The usage ratio of 6-pentamethyl-piperidines, hypohalous acid, catalyzer, alkali, solvent is counted by quality: 4-allyloxy-1,2,2,6,6-pentamethyl-piperidines: hypohalous acid: catalyzer: alkali: solvent=1:0.37-1.55:0.02-0.55:0.18-0.85:1.77-5.07.Described hypohalous acid is hypochlorous acid or hypobromous acid or hypoiodous acid, preferred hypochlorous acid; Described catalyzer is 4-propyl bromide or Tetrabutyl amonium bromide or cetyl trimethylammonium bromide, preferred 4-propyl bromide; Described alkali is sodium hydroxide or Pottasium Hydroxide or calcium hydroxide, preferably calcium hydroxide; Described solvent is sherwood oil or toluene or YLENE, preferred sherwood oil; The temperature of said hypochlorination's reaction is 35-50 ℃, and the dehydrochlorination reaction temperature is 70-95 ℃, and hypochlorination's reaction times is 4-8h, and the dehydrochlorination reaction time is 5-8.5h.
The present invention compared with prior art has the following advantages: the present invention is with 4-allyloxy-1,2,2,6; 6-pentamethyl-piperidines, hypohalous acid, alkali are synthetic photostabilizer of raw material and midbody 4-epoxypropyl-1,2,2,6; 6-pentamethyl-piperidines, it is simple to separate purification process, and the reaction times is short, and product yield is high; Reach more than 90%, less energy consumption, cost is low, is the comparatively ideal technology that realizes suitability for industrialized production.
Embodiment:
In order to deepen to understanding of the present invention, will combine embodiment that the present invention is made further detailed description below, the following example only is used to explain the present invention, does not constitute the qualification to protection domain of the present invention.
A kind of photostabilizer and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines, present method adopts 4-allyloxy-1; 2,2,6,6-pentamethyl-piperidines, hypohalous acid carry out hypohalous acid prepared in reaction 4-(2 '-chloro-hydroxypropyl)-1,2 in the presence of catalyzer; 2,6,6-pentamethyl-piperidines, after reaction was accomplished, the reaction solution standing demix fell moisture; In remaining mixed solution, add alkali, make it carry out de-hydrogen halide, reaction is filtered after finishing, and the material after the filtration is used SX, tells organic layer; Get organic phase, organic phase is carried out reflux divide water, decolour, filter, after the filtration mixed solution is heated, make the solvent release mixed solution with gac; Promptly get photostabilizer and midbody 4-epoxypropyl-1,2,2,6,6-pentamethyl-piperidines; Wherein, 4-allyloxy-1,2,2,6; The usage ratio of 6-pentamethyl-piperidines, hypohalous acid, catalyzer, alkali, solvent is counted by quality: 4-allyloxy-1,2,2,6,6-pentamethyl-piperidines: hypohalous acid: catalyzer: alkali: solvent=1:0.37-1.55:0.02-0.55:0.18-0.85:1.77-5.07.Described hypohalous acid is hypochlorous acid or hypobromous acid or hypoiodous acid, preferred hypochlorous acid; Described catalyzer is 4-propyl bromide or Tetrabutyl amonium bromide or cetyl trimethylammonium bromide, preferred 4-propyl bromide; Described alkali is sodium hydroxide or Pottasium Hydroxide or calcium hydroxide, preferably calcium hydroxide; Described solvent is sherwood oil or toluene or YLENE, preferred sherwood oil; The temperature of said hypochlorination's reaction is 35-50 ℃, and the dehydrochlorination reaction temperature is 70-95 ℃, and hypochlorination's reaction times is 4-8h, and the dehydrochlorination reaction time is 5-8.5h.
Embodiment 1:
In the four-hole boiling flask of the 250mL that stirring is housed, add 4-allyloxy-1,2,2; 6,6-pentamethyl-piperidines 21.1g, hypochlorous acid 8.2g, catalyzer 3g, agitator; Make the mixed solution in the flask carry out hypochlorination's reaction, control hypochlorination temperature of reaction is 35-50 ℃, and hypochlorination's reaction times is 4-8h, after reaction is accomplished; The reaction solution standing demix falls moisture, in remaining mixed solution, adds calcium hydroxide 11.1g; Make it carry out dehydrochlorination reaction, when control dehydrochlorination reaction temperature was 70-95 ℃, the dehydrochlorination reaction time was 5-8.5h.Reaction is filtered after finishing, and the material after the filtration is used the 50mL SX, tells organic layer; Organic phase is carried out reflux divide water, decolour, filter, after the filtration mixed solution is heated with gac; Make the solvent release mixed solution, promptly get photostabilizer and midbody 4-epoxypropyl-1,2,2; 6,6-pentamethyl-piperidines, product yield are 90.85%.
Embodiment 2:
In the four-hole boiling flask of the 250mL that stirring is housed, add 4-allyloxy-1,2,2; 6,6-pentamethyl-piperidines 21.1g, hypochlorous acid 13.1g, catalyzer 3g, agitator; Make the mixed solution in the flask carry out hypochlorination's reaction, control reaction temperature is 35-50 ℃, and the reaction times is 4-8h, after reaction is accomplished; The reaction solution standing demix falls moisture, in remaining mixed solution, adds calcium hydroxide 11.1g; Make it carry out dehydrochlorination reaction, when control dehydrochlorination reaction temperature was 70-95 ℃, the reaction times was 5-8.5h.Reaction is filtered after finishing, and the material after the filtration is used the 50mL SX, tells organic layer; Organic phase is carried out reflux divide water, decolour, filter, after the filtration mixed solution is heated with gac; Make the solvent release mixed solution, promptly get photostabilizer and midbody 4-epoxypropyl-1,2,2; 6,6-pentamethyl-piperidines, product yield are 91.12%.
Embodiment 3:
In the four-hole boiling flask of the 250mL that stirring is housed, add 4-allyloxy-1,2,2; 6,6-pentamethyl-piperidines 21.1g, hypochlorous acid 13.1g, catalyzer 5g, agitator; Make the mixed solution in the flask carry out hypochlorination's reaction, control reaction temperature is 35-50 ℃, and the reaction times is 4-8h, after reaction is accomplished; The reaction solution standing demix falls moisture, in remaining mixed solution, adds calcium hydroxide 11.1g; Make it carry out dehydrochlorination reaction, when control dehydrochlorination reaction temperature was 70-95 ℃, the reaction times was 5-8.5h.Reaction is filtered after finishing, and the material after the filtration is used the 50mL SX, tells organic layer; Organic phase is carried out reflux divide water, decolour, filter, after the filtration mixed solution is heated with gac; Make the solvent release mixed solution, promptly get photostabilizer and midbody 4-epoxypropyl-1,2,2; 6,6-pentamethyl-piperidines, product yield are 91.85%.
Embodiment 4:
In the four-hole boiling flask of the 250mL that stirring is housed, add 4-allyloxy-1,2,2; 6,6-pentamethyl-piperidines 21.1g, hypochlorous acid 15.8g, catalyzer 3g, agitator; Make the mixed solution in the flask carry out hypochlorination's reaction, control reaction temperature is 35-50 ℃, and the reaction times is 4-8h, after reaction is accomplished; The reaction solution standing demix falls moisture, in remaining mixed solution, adds calcium hydroxide 14.8g; Make it carry out dehydrochlorination reaction, when control dehydrochlorination reaction temperature was 70-95 ℃, the reaction times was 5-8.5h.Reaction is filtered after finishing, and the material after the filtration is used the 50mL SX, tells organic layer; Organic phase is carried out reflux divide water, decolour, filter, after the filtration mixed solution is heated with gac; Make the solvent release mixed solution, promptly get photostabilizer and midbody 4-epoxypropyl-1,2,2; 6,6-pentamethyl-piperidines, product yield are 92.31%.
Embodiment 5:
In the four-hole boiling flask of the 250mL that stirring is housed, add 4-allyloxy-1,2,2; 6,6-pentamethyl-piperidines 21.1g, hypochlorous acid 15.8g, catalyzer 5g, agitator; Make the mixed solution in the flask carry out hypochlorination's reaction, control reaction temperature is 35-50 ℃, and the reaction times is 4-8h, after reaction is accomplished; The reaction solution standing demix falls moisture, in remaining mixed solution, adds calcium hydroxide 9.6g; Make it carry out dehydrochlorination reaction, when control dehydrochlorination reaction temperature was 70-95 ℃, the reaction times was 5-8.5h.After reaction finished, the material after the filtration was used the 50mL SX, tells organic layer, organic phase is carried out reflux divide water; Decolour with gac, filter, after the filtration mixed solution is heated, make the solvent release mixed solution; Promptly get photostabilizer and midbody 4-epoxypropyl-1,2,2; 6,6-pentamethyl-piperidines, product yield are 90.92%.
The present invention is with 4-allyloxy-1,2,2,6; 6-pentamethyl-piperidines, hypohalous acid, alkali are synthetic photostabilizer of raw material and midbody 4-epoxypropyl-1,2,2,6; 6-pentamethyl-piperidines, it is simple to separate purification process, and the reaction times is short, and product yield is high; Reach more than 90%, less energy consumption, cost is low, is the comparatively ideal technology that realizes suitability for industrialized production.
Claims (10)
1. photostabilizer and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: adopt 4-allyloxy-1; 2,2,6,6-pentamethyl-piperidines, hypohalous acid carry out hypohalous acid prepared in reaction 4-(2 '-chloro-hydroxypropyl)-1,2 in the presence of catalyzer; 2,6,6-pentamethyl-piperidines, after reaction was accomplished, the reaction solution standing demix fell moisture; In remaining mixed solution, add alkali, make it carry out de-hydrogen halide, reaction is filtered after finishing, and the material after the filtration is used SX, tells organic layer; Get organic phase, organic phase is carried out reflux divide water, decolour, filter, after the filtration mixed solution is heated, make the solvent release mixed solution with gac; Promptly get photostabilizer and midbody 4-epoxypropyl-1,2,2,6,6-pentamethyl-piperidines; Wherein, 4-allyloxy-1,2,2,6; The usage ratio of 6-pentamethyl-piperidines, hypohalous acid, catalyzer, alkali, solvent is counted by quality: 4-allyloxy-1,2,2,6,6-pentamethyl-piperidines: hypohalous acid: catalyzer: alkali: solvent=1:0.37-1.55:0.02-0.55:0.18-0.85:1.77-5.07.
2. according to said photostabilizer of claim 1 and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: said hypohalous acid is hypochlorous acid or hypobromous acid or hypoiodous acid.
3. according to said photostabilizer of claim 2 and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: said hypohalous acid is a hypochlorous acid.
4. according to said photostabilizer of claim 1 and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: said catalyzer is 4-propyl bromide or Tetrabutyl amonium bromide or cetyl trimethylammonium bromide.
5. according to said photostabilizer of claim 4 and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: said catalyzer is a 4-propyl bromide.
6. according to said photostabilizer of claim 1 and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: said alkali is sodium hydroxide or Pottasium Hydroxide or calcium hydroxide.
7. according to said photostabilizer of claim 6 and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: said alkali is calcium hydroxide.
8. according to said photostabilizer of claim 1 and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: said solvent is sherwood oil or toluene or YLENE.
9. said according to Claim 8 photostabilizer and midbody 4-epoxypropyl-1,2,2,6, the preparation method of 6-pentamethyl-piperidines is characterized in that: said solvent is a sherwood oil.
10. according to said photostabilizer of claim 1 and midbody 4-epoxypropyl-1,2,2; 6; The preparation method of 6-pentamethyl-piperidines is characterized in that: the temperature of said hypochlorination's reaction is 35-50 ℃, and the dehydrochlorination reaction temperature is 70-95 ℃; The time of hypochlorination's reaction is 4-8h, and the dehydrochlorination reaction time is 5-8.5h.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114775918A (en) * | 2022-04-12 | 2022-07-22 | 广东安拓普聚合物科技有限公司 | Roof photovoltaic waterproof coiled material and preparation method thereof |
| CN115557935A (en) * | 2022-10-17 | 2023-01-03 | 南通大学 | Preparation method of hindered amine light stabilizer |
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| CN1066064A (en) * | 1991-04-24 | 1992-11-11 | 黑蒙特股份公司 | The preparation method of hindered amine as light stabilizer |
| US5457204A (en) * | 1993-07-13 | 1995-10-10 | Ciba-Geigy Corporation | Tetraalkyl-4-(2,3-epoxypropoxy) piperidine compounds as stabilizers |
| US5521282A (en) * | 1993-07-13 | 1996-05-28 | Ciba-Geigy Corporation | Polyethers containing hindered amine side chains as stabilizers |
| CN101973927A (en) * | 2010-10-26 | 2011-02-16 | 南通惠康国际企业有限公司 | Preparation method of light stabilizer 4-allyloxy-2,2,6,6-tetramethylpiperidine |
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Patent Citations (5)
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| US4537923A (en) * | 1982-06-17 | 1985-08-27 | Ciba Geigy Corporation | Polyalkylpiperidinesulfonic acid esters |
| CN1066064A (en) * | 1991-04-24 | 1992-11-11 | 黑蒙特股份公司 | The preparation method of hindered amine as light stabilizer |
| US5457204A (en) * | 1993-07-13 | 1995-10-10 | Ciba-Geigy Corporation | Tetraalkyl-4-(2,3-epoxypropoxy) piperidine compounds as stabilizers |
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| CN101973927A (en) * | 2010-10-26 | 2011-02-16 | 南通惠康国际企业有限公司 | Preparation method of light stabilizer 4-allyloxy-2,2,6,6-tetramethylpiperidine |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114775918A (en) * | 2022-04-12 | 2022-07-22 | 广东安拓普聚合物科技有限公司 | Roof photovoltaic waterproof coiled material and preparation method thereof |
| CN114775918B (en) * | 2022-04-12 | 2022-10-21 | 广东安拓普聚合物科技有限公司 | Roof photovoltaic waterproof coiled material and preparation method thereof |
| CN115557935A (en) * | 2022-10-17 | 2023-01-03 | 南通大学 | Preparation method of hindered amine light stabilizer |
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