CN102702174A - Method for preparing light stabilizer tri(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-oxy-piperidyl)-1,3,5-triazine - Google Patents
Method for preparing light stabilizer tri(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-oxy-piperidyl)-1,3,5-triazine Download PDFInfo
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- CN102702174A CN102702174A CN2012102023761A CN201210202376A CN102702174A CN 102702174 A CN102702174 A CN 102702174A CN 2012102023761 A CN2012102023761 A CN 2012102023761A CN 201210202376 A CN201210202376 A CN 201210202376A CN 102702174 A CN102702174 A CN 102702174A
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- China
- Prior art keywords
- tetramethyl
- piperidyl
- oxygen base
- cyclohexyloxy
- triazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 239000004611 light stabiliser Substances 0.000 title abstract description 3
- 238000000034 method Methods 0.000 title abstract 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 230000001590 oxidative effect Effects 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 28
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 18
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 13
- 150000000182 1,3,5-triazines Chemical class 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 6
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 6
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical group O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 6
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 claims description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- 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 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000009413 insulation Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229920001617 Vinyon Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for preparing a light stabilizer tri(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-oxy-piperidyl)-1,3,5-triazine. The method comprises the following step of: reacting cyanuric chloride, 2,2,6,6-tetramethyl-4-piperidinol and alkali serving as raw materials in the presence of a catalyst to obtain the tri(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-oxy-piperidyl)-1,3,5-triazine. The tri(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-oxy-piperidyl)-1,3,5-triazine is prepared from tri(2,2,6,6-tetramethyl-4-oxy-piperidyl)-1,3,5-triazine, cyclohexane and an oxidant serving as the raw materials, the separation and purification processes are simple, reaction time is short, the yield of the product is over 95 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
Technical field
The present invention relates to the preparation method of a kind of photostabilizer three (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines.
Background technology
Three (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines.It is the hindered amine type light stabilizer of high-efficiency low-toxicity low alkalinity.Good with most of industrial solvent intermiscibilities, have superior polymer intermiscibility, be applicable to Vestolen PP 7052, vinyon and fibre product.Its molecular formula is C
48H
84O
6N
3, molecular weight: 841.23, molecular structural formula:
Its outward appearance is the white solid powder.Three (1-cyclohexyloxy-2,2,6,6-tetramethyl-s-4-oxygen base-piperidyl)-1,3; Though the 5-triazine early has application, but about three (1-cyclohexyloxy-2,2,6,6-tetramethyl-s-4-oxygen base-piperidyl)-1; 3, the synthetic domestic literature report of 5-triazine is few, therefore studies three (1-cyclohexyloxies-2,2; 6,6-tetramethyl--4-oxygen base-piperidyl)-preparation method of 1,3,5-triazines has important industrial application value.
Summary of the invention
The object of the present invention is to provide a kind of environmental pollution little, cost is low, the preparation method of the photostabilizer three that product yield is high (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines.
Technical solution of the present invention is:
A kind of photostabilizer three (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3; The preparation method of 5-triazine is with three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1; 3,5-triazine, hexanaphthene, tertbutyl peroxide are raw material, and reaction makes three (1-cyclohexyloxies-2,2 under the condition that catalyzer exists; 6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines; Said catalyzer is sodium hydroxide or Pottasium Hydroxide or sodium hydride, preferred sodium hydroxide.Said catalyzer is molybdic oxide or Vanadium Pentoxide in FLAKES or chromium sesquioxide or tungstic oxide or Manganse Dioxide, preferred molybdic oxide.
Three (2,2,6; 6-tetramethyl--4-oxygen base-piperidyl)-and 1,3,5-triazines, hexanaphthene, tertbutyl peroxide, catalyst consumption ratio count by quality: three (2; 2,6,6-tetramethyl--4-oxygen base-piperidyl)-1; 3,5-triazine: hexanaphthene: tertbutyl peroxide: catalyzer=1:6.16 ~ 12.32:1.98 ~ 4.12:0.007 ~ 0.05.
With three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3; 5-triazine, hexanaphthene, tertbutyl peroxide are raw material, under the condition that catalyzer exists, oxidizing reaction take place, and reaction removes by filter catalyzer after finishing, and the organic phase after the filtration is carried out underpressure distillation; Distill out the hexanaphthene of hexanaphthene total amount 50%, be cooled to 8-10 ℃ then, crystallization is filtered, and promptly gets three (1-cyclohexyloxies-2; 2,6,6-tetramethyl--4-oxygen base-piperidyl)-the 1,3,5-triazines product.The temperature of said oxidizing reaction is 85-100 ℃.The time of said oxidizing reaction is 12-20h.
The present invention compared with prior art has the following advantages: the present invention synthesizes three (1-cyclohexyloxy-2,2,6,6-tetramethyl-s-4-oxygen base-piperidyl)-1; 3, the 5-triazine, it is simple to separate purification process, and the reaction times is short; Product yield reaches more than 95%, and product purity is higher, less energy consumption; Environmental pollution is little, and 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, this embodiment only is used to explain the present invention, does not constitute the qualification to protection domain of the present invention.
With three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3; 5-triazine, hexanaphthene, tertbutyl peroxide are raw material, under the condition that catalyzer exists, oxidizing reaction take place, and reaction removes by filter catalyzer after finishing, and the organic phase after the filtration is carried out underpressure distillation; Distill out the hexanaphthene of hexanaphthene total amount 50%, be cooled to 8-10 ℃ then, crystallization is filtered, and promptly gets three (1-cyclohexyloxies-2; 2,6,6-tetramethyl--4-oxygen base-piperidyl)-the 1,3,5-triazines product.The temperature of said oxidizing reaction is 85-100 ℃.The time of said oxidizing reaction is 12-20h.Said catalyzer is sodium hydroxide or Pottasium Hydroxide or sodium hydride, preferred sodium hydroxide.Said catalyzer is molybdic oxide or Vanadium Pentoxide in FLAKES or chromium sesquioxide or tungstic oxide or Manganse Dioxide, preferred molybdic oxide.
Embodiment 1:
In the four-hole boiling flask of 500mL, add three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1; 3,5-triazine 54.7g, hexanaphthene 336.6g, catalyzer 0.4g after the dissolving, loads onto reflux condensing tube, TM fully; Agitator drips 85-100 ℃ of tertbutyl peroxide 108.1g controlled oxidation temperature of reaction in the 10h, insulation reaction 2-10h, and reaction removes by filter catalyzer after finishing; Organic phase after the filtration is carried out underpressure distillation, distills out the hexanaphthene and the by product trimethyl carbinol of hexanaphthene total amount 50%, is cooled to 8-10 ℃ then, crystallization; Filter, promptly get three (1-cyclohexyloxy-2,2,6; 6-tetramethyl--4-oxygen base-piperidyl)-and the 1,3,5-triazines product, product yield is 95.01%.
Embodiment 2:
In the four-hole boiling flask of 500mL, add three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1; 3,5-triazine 54.7g, hexanaphthene 420.8g, catalyzer 0.6g after the dissolving, loads onto reflux condensing tube, TM fully; Agitator drips 85-100 ℃ of tertbutyl peroxide 108.1g controlled oxidation temperature of reaction in the 10h, insulation reaction 2-10h, and reaction removes by filter catalyzer after finishing; Organic phase after the filtration is carried out underpressure distillation, distills out the hexanaphthene and the by product trimethyl carbinol of hexanaphthene total amount 50%, is cooled to 8-10 ℃ then, crystallization; Filter, promptly get three (1-cyclohexyloxy-2,2,6; 6-tetramethyl--4-oxygen base-piperidyl)-and the 1,3,5-triazines product, product yield is 96.25%.
Embodiment 3:
In the four-hole boiling flask of 500mL, add three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1; 3,5-triazine 54.7g, hexanaphthene 673.3g, catalyzer 1.5g after the dissolving, loads onto reflux condensing tube, TM fully; Agitator drips 85-100 ℃ of tertbutyl peroxide 108.1g controlled oxidation temperature of reaction in the 10h, insulation reaction 2-10h, and reaction removes by filter catalyzer after finishing; Organic phase after the filtration is carried out underpressure distillation, distills out the hexanaphthene and the by product trimethyl carbinol of hexanaphthene total amount 50%, is cooled to 8-10 ℃ then, crystallization; Filter, promptly get three (1-cyclohexyloxy-2,2,6; 6-tetramethyl--4-oxygen base-piperidyl)-and the 1,3,5-triazines product, product yield is 96.47%.
Embodiment 4:
In the four-hole boiling flask of 500mL, add three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1; 3,5-triazine 54.7g, hexanaphthene 336.6g, catalyzer 0.8g after the dissolving, loads onto reflux condensing tube, TM fully; Agitator drips 85-100 ℃ of tertbutyl peroxide 162.2g controlled oxidation temperature of reaction in the 10h, insulation reaction 2-10h, and reaction removes by filter catalyzer after finishing; Organic phase after the filtration is carried out underpressure distillation, distills out the hexanaphthene and the by product trimethyl carbinol of hexanaphthene total amount 50%, is cooled to 8-10 ℃ then, crystallization; Filter, promptly get three (1-cyclohexyloxy-2,2,6; 6-tetramethyl--4-oxygen base-piperidyl)-and the 1,3,5-triazines product, product yield is 95.78%.
Embodiment 5:
In the four-hole boiling flask of 500mL, add three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1; 3,5-triazine 54.7g, hexanaphthene 420.8g, catalyzer 1.0g after the dissolving, loads onto reflux condensing tube, TM fully; Agitator drips 85-100 ℃ of tertbutyl peroxide 135.2g controlled oxidation temperature of reaction in the 10h, insulation reaction 2-10h, and reaction removes by filter catalyzer after finishing; Organic phase after the filtration is carried out underpressure distillation, distills out the hexanaphthene and the by product trimethyl carbinol of hexanaphthene total amount 50%, is cooled to 8-10 ℃ then, crystallization; Filter, promptly get three (1-cyclohexyloxy-2,2,6; 6-tetramethyl--4-oxygen base-piperidyl)-and the 1,3,5-triazines product, product yield is 96.61%.
The present invention synthesizes three (1-cyclohexyloxy-2,2,6,6-tetramethyl-s-4-oxygen base-piperidyl)-1; 3, the 5-triazine, it is simple to separate purification process, and the reaction times is short; Product yield reaches more than 95%, and product purity is higher, less energy consumption; Environmental pollution is little, and cost is low, is the comparatively ideal technology that realizes suitability for industrialized production.
Claims (5)
1. the preparation method of a photostabilizer three (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines; It is characterized in that: with three (2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3; 5-triazine, hexanaphthene, tertbutyl peroxide are raw material, under the condition that catalyzer exists, oxidizing reaction take place, and reaction removes by filter catalyzer after finishing, and the organic phase after the filtration is carried out underpressure distillation; Distill out the hexanaphthene of hexanaphthene total amount 50%, be cooled to 8-10 ℃ then, crystallization is filtered, and promptly gets three (1-cyclohexyloxies-2; 2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines.
2. photostabilizer three according to claim 1 (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1; 3, the 5-triazine is characterized in that: said three (2,2; 6,6-tetramethyl--4-oxygen base-piperidyl)-1,3; 5-triazine, hexanaphthene, tertbutyl peroxide, catalyst consumption ratio are counted by quality: three (2,2,6; 6-tetramethyl--4-oxygen base-piperidyl)-and 1,3,5-triazines: hexanaphthene: tertbutyl peroxide: catalyzer=1:6.16 ~ 12.32:1.98 ~ 4.12:0.007 ~ 0.05.
3. photostabilizer three according to claim 1 and 2 (1-cyclohexyloxy-2,2,6; 6-tetramethyl--4-oxygen base-piperidyl)-1; 3, the 5-triazine is characterized in that: said catalyzer is molybdic oxide or Vanadium Pentoxide in FLAKES or chromium sesquioxide or tungstic oxide or Manganse Dioxide.
4. according to the preparation method of the said photostabilizer three of claim 3 (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines, it is characterized in that: said catalyzer is a molybdic oxide.
5. according to the preparation method of the said photostabilizer three of claim 1 (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines, it is characterized in that: the temperature of said oxidizing reaction is 85-100 ℃, and the time of oxidizing reaction is 12-20h.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348525A (en) * | 2015-10-19 | 2016-02-24 | 北京天罡助剂有限责任公司 | Low-alkalinity polymeric hindered amine light stabilizing agent and preparation method thereof |
| WO2020259195A1 (en) * | 2019-06-25 | 2020-12-30 | 北京天罡助剂有限责任公司 | Polymeric polymer sterically hindered amine and preparation method therefor |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101570507A (en) * | 2008-04-28 | 2009-11-04 | 大丰市天生化学工业有限公司 | Process for preparing bi-(n-octyloxy-2,2,6,6-tetramethyl-piperidyl) diester sebacate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101570507A (en) * | 2008-04-28 | 2009-11-04 | 大丰市天生化学工业有限公司 | Process for preparing bi-(n-octyloxy-2,2,6,6-tetramethyl-piperidyl) diester sebacate |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348525A (en) * | 2015-10-19 | 2016-02-24 | 北京天罡助剂有限责任公司 | Low-alkalinity polymeric hindered amine light stabilizing agent and preparation method thereof |
| WO2020259195A1 (en) * | 2019-06-25 | 2020-12-30 | 北京天罡助剂有限责任公司 | Polymeric polymer sterically hindered amine and preparation method therefor |
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Denomination of invention: Preparation of tris (1-cyclohexoxy-2,2,6,6-tetramethyl-4-oxy-piperidinyl) - 1,3,5-triazine Effective date of registration: 20200922 Granted publication date: 20150812 Pledgee: Jiangsu Zhangjiagang rural commercial bank Limited by Share Ltd. Nantong branch Pledgor: RUDONG JINKANGTAI CHEMICAL Co.,Ltd. Registration number: Y2020320000195 |
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Date of cancellation: 20230804 Granted publication date: 20150812 Pledgee: Jiangsu Zhangjiagang rural commercial bank Limited by Share Ltd. Nantong branch Pledgor: RUDONG JINKANGTAI CHEMICAL CO.,LTD. Registration number: Y2020320000195 |
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Denomination of invention: Preparation method of light stabilizer tris (1-cyclohexoxy-2,2,6,6-tetramethyl-4-oxy-piperidinyl) -1,3,5-triazine Effective date of registration: 20230809 Granted publication date: 20150812 Pledgee: Jiangsu Zhangjiagang rural commercial bank Limited by Share Ltd. Nantong branch Pledgor: RUDONG JINKANGTAI CHEMICAL CO.,LTD. Registration number: Y2023320000413 |