CN103012251A - Preparation method of hindered amine light stabilizer intermediate compound 1-octoxy-2,2,6,6-tetramethyl-4-hydroxypiperidine - Google Patents
Preparation method of hindered amine light stabilizer intermediate compound 1-octoxy-2,2,6,6-tetramethyl-4-hydroxypiperidine Download PDFInfo
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- CN103012251A CN103012251A CN2013100046049A CN201310004604A CN103012251A CN 103012251 A CN103012251 A CN 103012251A CN 2013100046049 A CN2013100046049 A CN 2013100046049A CN 201310004604 A CN201310004604 A CN 201310004604A CN 103012251 A CN103012251 A CN 103012251A
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- tetramethyl
- hydroxy piperidine
- octyloxy
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- hindered amine
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 150000001412 amines Chemical class 0.000 title claims abstract description 16
- 239000004611 light stabiliser Substances 0.000 title claims abstract description 15
- MMKOHTDGXBBEAH-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-octoxypiperidin-4-ol Chemical compound CCCCCCCCON1C(C)(C)CC(O)CC1(C)C MMKOHTDGXBBEAH-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 title abstract description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 24
- -1 2,2,6,6-tetramethyl-4-hydroxypiperidine nitroxide free radical Chemical class 0.000 claims abstract description 21
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 239000012074 organic phase Substances 0.000 claims description 24
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000010992 reflux Methods 0.000 claims description 13
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical group O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 12
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 claims description 6
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 5
- 229960004643 cupric oxide Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 9
- 230000035484 reaction time Effects 0.000 abstract description 8
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000009835 boiling Methods 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229910018487 Ni—Cr Inorganic materials 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
Abstract
The invention discloses a preparation method of a hindered amine light stabilizer intermediate compound 1-octoxy-2,2,6,6-tetramethyl-4-hydroxypiperidine, which comprises the following step: in the presence of a catalyst, reacting 2,2,6,6-tetramethyl-4-hydroxypiperidine nitroxide free radical, n-octane and tert-butyl hydroperoxide used as raw materials, thus preparing the 1-octoxy-2,2,6,6-tetramethyl-4-hydroxypiperidine. According to the invention, the 1-octoxy-2,2,6,6-tetramethyl-4-hydroxypiperidine is synthesized by taking the 2,2,6,6-tetramethyl-4-hydroxypiperidine nitroxide free radical, the n-octane and the tert-butyl hydroperoxide as raw materials, so that the preparation method has the advantages of simple separation and purification process, short reaction time, product yield up to 92% or above, high product purity, low energy consumption, less environmental pollution and low cost, thereby being an ideal process for realizing industrial production.
Description
Technical field
The present invention relates to a kind of hindered amine light stabilizer intermediate 1-octyloxy-2,2,6, the preparation method of 6-tetramethyl--4-hydroxy piperidine.
Background technology
Hindered amine light stabilizer intermediate 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine are the liquid photostabilizer of the hindered amine type of low alkalinity, high-efficiency low-toxicity, can prolong the duration of service that various plastic cement and coating shine out of doors.Be the intermediate of two (1-octyloxy-2,2,6, the 6-tetramethyl--4-piperidyl) sebates of synthetic photostabilizer, can be used for emulsion paint, alkyd paint, epoxy-based lacquers etc.With various coating good consistency is arranged, with Benzotriazole Ultraviolet Stabilizer UV-327, UV-326, UV-9 has synergistic effect, also be applicable to polyolefine, unsaturated polyester, the polymkeric substance such as polymethylmethacrylate, be specially adapted to urethane, this product has significant anti-photooxidation (sun-proof) effect that wears out, particularly can be superior far beyond general UV light absorber and quencher (nickel chromium triangle compound) to the resistance to weathering of polypropylene and high density polyethylene(HDPE), be particularly useful for thick product, different with traditional ultraviolet absorbers, its effect and products thickness are irrelevant, therefore also are suitable for the product of high-specific surface area.Its advantage is its high efficiency, and simultaneously it and resin have good consistency and dispersiveness.In addition, the plastics such as p-poly-phenyl ethene, HIPS, ABS resin and urethane are also effective, can be used for polypropylene, impact-resistant modified polypropylene (TPO), EPDM, polystyrene, impact-resistant polystyrene, ABS, SAN, ASA, also can be used for urethane, polymeric amide, polyacetal etc., its light stabilising effect is good.Its molecular formula is C
17H
35O
2N, molecular weight: 287.5, molecular structural formula:
Its outward appearance is colourless liquid, boiling point〉350 ℃.
At present, the preparation 1-octyloxy-2,2,6 of bibliographical information, the method for 6-tetramethyl--4-hydroxy piperidine is few, and according to molecular structural formula, we have designed a kind of 1-octyloxy-2,2,6, the method for 6-tetramethyl--4-hydroxy piperidine compou nd synthesis.Adopt 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane are raw material, carry out the synthetic 1-octyloxy-2,2 of oxidizing reaction with tertbutyl peroxide in the presence of catalyzer, 6,6-tetramethyl--4-hydroxy piperidine, the catalyzer that the method adopts has high reactivity and highly selective, speed of response is fast, consumption is few, and product yield is high, and chemical stability is good, aftertreatment is simple, not the advantage such as etching apparatus.
Summary of the invention
The object of the present invention is to provide a kind of environmental pollution little, cost is low, the preparation hindered amine light stabilizer intermediate 1-octyloxy-2,2,6 that product yield is high, the method for 6-tetramethyl--4-hydroxy piperidine.
Technical solution of the present invention is:
A kind of hindered amine light stabilizer intermediate 1-octyloxy-2, the preparation method of 2,6,6-tetramethyl--4-hydroxy piperidine, with 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane and tertbutyl peroxide are raw material, reaction makes 1-octyloxy-2 under the condition that catalyzer exists, 2,6,6-tetramethyl--4-hydroxy piperidine; Described catalyzer is chromium sesquioxide or Manganse Dioxide or cupric oxide, excellent chromium sesquioxide.
2,2,6, the usage ratio of 6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide, catalyzer is by mass: 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical: octane: tertbutyl peroxide: catalyzer=1:4 ~ 5.35:1.45 ~ 2.25:0.015 ~ 0.12.
Be raw material with 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide, under the condition that catalyzer exists, react that reaction leaches catalyzer after finishing, and washes, and tells organic phase; Organic phase is carried out reflux water-dividing, decolouring again, and the organic phase that obtains is carried out desolventizing, namely gets 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine.The temperature of described reaction is 110 ~ 125 ℃.The time of described reaction is 6-12h.
The present invention compared with prior art has the following advantages: the present invention is with 2,2, and 6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide are the synthetic 1-octyloxy-2,2 of raw material, 6,6-tetramethyl--4-hydroxy piperidine, the separating-purifying process is simple, and the reaction times is short, the yield of product can reach more than 92%, product purity is high, and energy consumption is low, and environmental pollution is little, 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 this embodiment only is used for explaining the present invention, does not consist of the restriction to protection domain of the present invention.
A kind of hindered amine light stabilizer intermediate 1-octyloxy-2, the preparation method of 2,6,6-tetramethyl--4-hydroxy piperidine, with 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane and tertbutyl peroxide are raw material, reaction makes 1-octyloxy-2 under the condition that catalyzer exists, 2,6,6-tetramethyl--4-hydroxy piperidine; Described catalyzer is chromium sesquioxide or Manganse Dioxide or cupric oxide, excellent chromium sesquioxide.2,2,6, the usage ratio of 6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide, catalyzer is by mass: 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical: octane: tertbutyl peroxide: catalyzer=1:4 ~ 5.35:1.45 ~ 2.25:0.015 ~ 0.12.The temperature of described reaction is 110 ~ 125 ℃.The time of described reaction is 6-12h.
Be raw material with 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide, under the condition that catalyzer exists, react that reaction leaches catalyzer after finishing, and washes, and tells organic phase; Organic phase is carried out reflux water-dividing, decolouring again, and the organic phase that obtains is carried out desolventizing, namely gets 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine.
Embodiment 1:
In the four-hole boiling flask of 500mL, add 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical 34.3g, octane 147.5g, catalyzer 0.5g, tertbutyl peroxide 73.5g loads onto reflux condensing tube, thermometer, start agitator, 110-125 ℃ of control temperature, the reaction times is 6-12h, after reaction finishes, leach catalyzer, wash, tell organic phase; Organic phase is carried out reflux water-dividing, decolouring again, and the organic phase that obtains is carried out desolventizing, namely gets 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine product, and product yield is 92.13%.
Embodiment 2:
In the four-hole boiling flask of 500mL, add 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical 34.3g, octane 147.5g, catalyzer 0.5g, tertbutyl peroxide 73.5g loads onto reflux condensing tube, thermometer, start agitator, 110-125 ℃ of control temperature, the reaction times is 6-12h, after reaction finishes, leach catalyzer, wash, tell organic phase; Organic phase is carried out reflux water-dividing, decolouring again, and the organic phase that obtains is carried out desolventizing, namely gets 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine product, and product yield is 92.64%.
Embodiment 3:
In the four-hole boiling flask of 500mL, add 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical 34.3g, octane 164.6g, catalyzer 0.5g, tertbutyl peroxide 83.3g loads onto reflux condensing tube, thermometer, start agitator, 110-125 ℃ of control temperature, the reaction times is 6-12h, after reaction finishes, leach catalyzer, wash, tell organic phase; Organic phase is carried out reflux water-dividing, decolouring again, and the organic phase that obtains is carried out desolventizing, namely gets 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine product, and product yield is 92.95%.
Embodiment 4:
In the four-hole boiling flask of 500mL, add 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical 34.3g, octane 164.6g, catalyzer 1.0g, tertbutyl peroxide 83.3g loads onto reflux condensing tube, thermometer, start agitator, 110-125 ℃ of control temperature, the reaction times is 6-12h, after reaction finishes, leach catalyzer, wash, tell organic phase; Organic phase is carried out reflux water-dividing, decolouring again, and the organic phase that obtains is carried out desolventizing, namely gets 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine product, and product yield is 93.28%.
Embodiment 5:
In the four-hole boiling flask of 500mL, add 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical 34.3g, octane 183.5g, catalyzer 0.3g, tertbutyl peroxide 110.3g loads onto reflux condensing tube, thermometer, start agitator, 110-125 ℃ of control temperature, the reaction times is 6-12h, after reaction finishes, leach catalyzer, wash, tell organic phase; Organic phase is carried out reflux water-dividing, decolouring again, and the organic phase that obtains is carried out desolventizing, namely gets 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine product, and product yield is 92.56%.
The present invention is with 2,2, and 6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide are the synthetic 1-octyloxy-2,2 of raw material, 6,6-tetramethyl--4-hydroxy piperidine, the separating-purifying process is simple, and the reaction times is short, the yield of product can reach more than 92%, product purity is high, and energy consumption is low, and environmental pollution is little, cost is low, is the comparatively ideal technique that realizes suitability for industrialized production.
Claims (7)
1. hindered amine light stabilizer intermediate 1-octyloxy-2, the preparation method of 2,6,6-tetramethyl--4-hydroxy piperidine, it is characterized in that: be with 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide are raw material, reaction preparation 1-octyloxy-2 under the condition that catalyzer exists, 2,6,6-tetramethyl--4-hydroxy piperidine.
2. a kind of hindered amine light stabilizer intermediate 1-octyloxy-2,2 according to claim 1,6, the preparation method of 6-tetramethyl--4-hydroxy piperidine, it is characterized in that: with 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide are raw material, react under the condition that catalyzer exists, reaction leaches catalyzer after finishing, wash, tell organic phase; Organic phase is carried out reflux water-dividing, decolouring again, and the organic phase that obtains is carried out desolventizing, namely gets 1-octyloxy-2,2,6,6-tetramethyl--4-hydroxy piperidine.
3. a kind of hindered amine light stabilizer intermediate 1-octyloxy-2 according to claim 1 and 2,2, the preparation method of 6,6-tetramethyl--4-hydroxy piperidine is characterized in that: described 2,2, the usage ratio of 6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical, octane, tertbutyl peroxide, catalyzer is by mass: 2,2,6,6-tetramethyl--4-hydroxy piperidine nitroxyl free radical: octane: tertbutyl peroxide: catalyzer=1:4 ~ 5.35:1.45 ~ 2.25:0.015 ~ 0.12.
4. a kind of hindered amine light stabilizer intermediate 1-octyloxy-2,2,6 according to claim 1 and 2, the preparation method of 6-tetramethyl--4-hydroxy piperidine is characterized in that: described catalyzer is chromium sesquioxide or Manganse Dioxide or cupric oxide.
5. a kind of hindered amine light stabilizer intermediate 1-octyloxy-2,2,6 according to claim 4, the preparation method of 6-tetramethyl--4-hydroxy piperidine is characterized in that: described catalyzer is chromium sesquioxide.
6. a kind of hindered amine light stabilizer intermediate 1-octyloxy-2,2,6 according to claim 1 and 2, the preparation method of 6-tetramethyl--4-hydroxy piperidine is characterized in that: the temperature of described reaction is 110-125 ℃.
7. a kind of hindered amine light stabilizer intermediate 1-octyloxy-2,2,6 according to claim 1 and 2, the preparation method of 6-tetramethyl--4-hydroxy piperidine is characterized in that: the time of described reaction is 6-12h.
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Cited By (3)
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| CN110283116A (en) * | 2019-06-27 | 2019-09-27 | 绍兴瑞康生物科技有限公司 | A kind of novel hindered amine light stabilizer and preparation and application |
| CN110903237A (en) * | 2019-12-16 | 2020-03-24 | 兰州精细化工有限责任公司 | Preparation method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN114369057A (en) * | 2021-12-14 | 2022-04-19 | 利安隆凯亚(河北)新材料有限公司 | Hindered amine compound and application and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110283116A (en) * | 2019-06-27 | 2019-09-27 | 绍兴瑞康生物科技有限公司 | A kind of novel hindered amine light stabilizer and preparation and application |
| CN110283116B (en) * | 2019-06-27 | 2022-09-09 | 绍兴瑞康生物科技有限公司 | Hindered amine light stabilizer, preparation and application thereof |
| CN110903237A (en) * | 2019-12-16 | 2020-03-24 | 兰州精细化工有限责任公司 | Preparation method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
| CN114369057A (en) * | 2021-12-14 | 2022-04-19 | 利安隆凯亚(河北)新材料有限公司 | Hindered amine compound and application and preparation method thereof |
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