CN101768104B - Method for producing light stabilizer sebacic acid (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) diester - Google Patents
Method for producing light stabilizer sebacic acid (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) diester Download PDFInfo
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- CN101768104B CN101768104B CN2010100172029A CN201010017202A CN101768104B CN 101768104 B CN101768104 B CN 101768104B CN 2010100172029 A CN2010100172029 A CN 2010100172029A CN 201010017202 A CN201010017202 A CN 201010017202A CN 101768104 B CN101768104 B CN 101768104B
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- pentamethyl
- piperidyl
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 title claims abstract description 51
- -1 1, 2, 2, 6, 6-pentamethyl-4-piperidyl Chemical group 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 239000004611 light stabiliser Substances 0.000 title abstract description 3
- 150000005690 diesters Chemical class 0.000 title abstract 4
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 229940014772 dimethyl sebacate Drugs 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 13
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 230000035484 reaction time Effects 0.000 claims abstract description 10
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical class CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims description 20
- 238000001556 precipitation Methods 0.000 claims description 8
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 7
- 238000012544 monitoring process Methods 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000002585 base Substances 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
- 239000000203 mixture Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- XULIXFLCVXWHRF-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidine Chemical class CN1C(C)(C)CCCC1(C)C XULIXFLCVXWHRF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018487 Ni—Cr Inorganic materials 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- OSYQOBUUFRGFNG-UHFFFAOYSA-N Sebacic acid monomethyl ester Chemical class COC(=O)CCCCCCCCC(O)=O OSYQOBUUFRGFNG-UHFFFAOYSA-N 0.000 description 1
- 229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines 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
- YHEPZZFDBQOSSN-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate;1-o-methyl 10-o-(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound COC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1.C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 YHEPZZFDBQOSSN-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 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
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011973 solid acid Substances 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
- 229920006305 unsaturated polyester Polymers 0.000 description 1
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- Hydrogenated Pyridines (AREA)
Abstract
The invention discloses a method for producing a light stabilizer sebacic acid (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) diester. In the method, dimethyl sebacate, 1, 2, 2, 6, 6-pentamethyl-4-hydroxypiperidines serves as the raw material and reaction is carried out in the presence of solvent and catalyst at certain temperature to obtain sebacic acid (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) diester. In the invention, the dimethyl sebacate, 1, 2, 2, 6, 6-pentamethyl-4-hydroxypiperidines serve as raw materials for synthesizing sebacic acid (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) diester, active carbon loaded tetraisopropyl titanate catalyst is employed; as a result, separation and purification process is simplified, the reaction time is short, product yield is more than 97%, the catalyst can be repeatedly used; in addition, the method of the invention features high purity of obtained product, reduced energy consumption, little environmental pollution, low cost, thus being an ideal technology for industrialized production.
Description
Technical field:
The present invention relates to the working method of a kind of photostabilizer sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester.
Background technology:
Sebacic acid two (1,2,2,6,6-pentamethyl--4-hydroxy piperidine base) ester is the hindered amine type light stabilizer of lower molecular weight, low alkalinity, high-efficiency low-toxicity, 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, product is not volatile during high temperature process.Good with most of industrial solvent intermiscibilities, have superior polymer intermiscibility, this product is coating and printing ink photostabilizer; Can be used for vinylformic acid and polyurethane paint, prevent that effectively coating from tanning by the sun generation foaming down and peel off on the top layer, also can be used for rubber-emulsion paint, alkyd paint, epoxy-based lacquers etc.; With various coating good consistency is arranged; With benzotriazole category UV light absorber UV-327, UV-326, UV-9 synergistic effect is arranged, also be applicable to polymkeric substance such as polyolefine, unsaturated polyester, polymethylmethacrylate, be specially adapted to urethane; This product has significant anti-photooxidation (sun-proof) effect that wears out; Particularly the resistance to weathering to Vestolen PP 7052 and high density polyethylene(HDPE) can be superior far beyond general UV light absorber and quencher (nickel chromium triangle compound), is particularly useful for thick product, and is 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, plastics such as p-poly-phenyl ethene, HIPS, ABS resin and urethane are also effective, can be used for Vestolen PP 7052, impact-resistant modified Vestolen PP 7052 (TPO), EPDM; PS, impact-resistant polystyrene, ABS, SAN, ASA; Also can be used for urethane, polymeric amide, polyacetal etc., its light stabilising effect is good.Its chemical name is: sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester;
Molecular formula: C
30H
56O
4N
2Molecular weight: 508.75
Molecular structural formula:
Physico-chemical property: outward appearance is colourless or light yellow liquid, boiling point＞350 ℃.
At present, adopt the domestic disclosed research report of activated carbon supported tetra isopropyl titanate catalysis sebacic acid two (1,2,2,6,6-pentamethyl--4-hydroxy piperidine base) ester compound method few; And domesticly have only research photostabilizer UV-292 [two (1,2,2,6,6-pentamethyl-piperidines alcohol) sebates and single (1,2; 2,6,6-pentamethyl-piperidines alcohol) mixture of sebacic acid methyl esters] the research report, this institute obtain two (1,2; 2,6,6-pentamethyl-piperidines alcohol) sebate and single (1,2,2; 6,6-pentamethyl-piperidines alcohol) the mixture color of sebacic acid methyl esters is darker, and temperature of reaction is high, and the aftertreatment technology more complicated is not suitable for suitability for industrialized production.According to reported in literature, adopt Lewis acid, alkali etc. for catalyzer carries out transesterification reaction, the catalyzer corrosive equipment, the pollution that aftertreatment produces is big, poor product quality.Adopt the solid acid catalyst catalyzed transesterification, little though product and catalyzer are easily separated to corrosion on Equipment property, the recyclable utilization of catalyzer, selectivity is with active low.
Summary of the invention:
The object of the present invention is to provide the working method of the high photostabilizer sebacic acid two of a kind of product yield (1,2,2,6,6-pentamethyl--4-piperidyl) ester.
Technical solution of the present invention is:
The working method of a kind of photostabilizer sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester; Be with dimethyl sebacate and 1,2,2,6,6-pentamethyl--4-hydroxy piperidine is a raw material; Under the condition of solvent and catalyzer existence, solvent is sherwood oil or YLENE, is heated to certain temperature, and reaction makes sebacic acid two (1; 2,2,6,6-pentamethyl--4-piperidyl) ester; Said catalyzer is activated carbon supported tetra isopropyl titanate.
Dimethyl sebacate, 1,2,2; 6, the usage ratio of 6-pentamethyl--4-hydroxy piperidine, catalyzer, solvent is counted by quality: dimethyl sebacate: 1,2; 2,6,6-pentamethyl--4-hydroxy piperidine: catalyzer: solvent=1: 1.4～2.2: 0.03～0.15: 1.6～2.0.
With dimethyl sebacate, 1,2,2,6; 6-pentamethyl--4-hydroxy piperidine is a raw material, under the condition of solvent and catalyzer existence, carries out transesterification reaction, and reaction is filtered, washed after finishing; Tell organic layer, in the organic layer solution of telling, dewater, decolouring, precipitation get sebacic acid two (1,2; 2,6,6-pentamethyl--4-piperidyl) ester.The temperature of said reaction is 100～120 ℃, and the reaction times is 2h.
The present invention is with dimethyl sebacate, 1,2,2,6, and 6-pentamethyl--4-hydroxy piperidine is a raw material synthesis of sebacic acid two (1; 2,2,6,6-pentamethyl--4-piperidyl) ester, adopt activated carbon supported tetra isopropyl titanate catalyzer; Simplified the separation purification process, the reaction times is short, and product yield is high, and catalyzer can be reused repeatedly, and the yield of product is reached more than 97%; It is higher to obtain product purity, and energy consumption reduces, and environmental pollution is little, and cost is low, is the comparatively ideal technology that realizes suitability for industrialized production.
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.
Embodiment:
A kind of photostabilizer sebacic acid two (1,2,2,6; 6-pentamethyl--4-piperidyl) working method of ester is with dimethyl sebacate, 1,2,2; 6,6-pentamethyl--4-hydroxy piperidine is a raw material, under the condition of solvent and catalyzer existence, carries out transesterification reaction at a certain temperature and makes sebacic acid two (1; 2,2,6,6-pentamethyl--4-piperidyl) ester.Dimethyl sebacate, 1,2,2; 6, the usage ratio of 6-pentamethyl--4-hydroxy piperidine, catalyzer, solvent is counted by quality: dimethyl sebacate: 1,2; 2,6,6-pentamethyl--4-hydroxy piperidine: catalyzer: solvent=1: 1.4～2.2: 0.03～0.15: 1.6～2.0.The catalyzer of said transesterification reaction is activated carbon supported tetra isopropyl titanate, and this catalyzer can be reused 4～8 times.
Embodiment 1:
In the four-hole boiling flask of the 250mL that TM is housed, add sherwood oil 40g, dimethyl sebacate 23.0g, 1; 2,2,6,6-pentamethyl--4-hydroxy piperidine 35.12g; Catalyzer 1.2g loads onto prolong, agitator; When being warming up to 100-120 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 2h (using the gc monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, precipitation get sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester, and product yield is 97.01%.
Embodiment 2:
In the four-hole boiling flask of the 250mL that TM is housed, add sherwood oil 40g, dimethyl sebacate 23.0g, 1; 2,2,6,6-pentamethyl--4-hydroxy piperidine 50.6g; Catalyzer 1.2g loads onto prolong, agitator; When being warming up to 100-120 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 2h (using the gc monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, precipitation get sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester, and product yield is 98.73%.
Embodiment 3:
In the four-hole boiling flask of the 250mL that TM is housed, add sherwood oil 40g, dimethyl sebacate 23.0g, 1; 2,2,6,6-pentamethyl--4-hydroxy piperidine 36.83g; Catalyzer 1.2g loads onto prolong, agitator; When being warming up to 100-120 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 2h (using the gc monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, precipitation get sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester, and product yield is 97.63%.
Embodiment 4:
In the four-hole boiling flask of the 250mL that TM is housed, add sherwood oil 40g, dimethyl sebacate 23.0g, 1; 2,2,6,6-pentamethyl--4-hydroxy piperidine 46.0g; Catalyzer 1.2g loads onto prolong, agitator; When being warming up to 100-120 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 2h (using the gc monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, precipitation get sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester, and product yield is 97.91%.
Embodiment 5:
In the four-hole boiling flask of the 250mL that TM is housed, add YLENE 40g, dimethyl sebacate 23.0g, 1,2,2,6,6-pentamethyl--4-hydroxy piperidine 41.4g, catalyzer 1.4g, this catalyzer are the 4th repeated use.Load onto prolong, agitator when being warming up to 100-120 ℃, constantly steams the methyl alcohol of generation in the reaction process, reaction times 2h (using the gc monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, precipitation get sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester, and product yield is 97.55%.
Embodiment 6:
In the four-hole boiling flask of the 250mL that TM is housed, add YLENE 40g, dimethyl sebacate 23.0g, 1; 2,2,6,6-pentamethyl--4-hydroxy piperidine 32.25g; Catalyzer 1.6g loads onto prolong, agitator; When being warming up to 100-120 ℃, constantly steam the methyl alcohol of generation in the reaction process, reaction times 2h (using the gc monitoring reaction).After reaction finishes, filter, wash, collect organic phase, organic phase dewaters, decolouring, precipitation get sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester, and product yield is 98.34%.
Claims (2)
1. the working method of a photostabilizer sebacic acid two (1,2,2,6,6-pentamethyl--4-piperidyl) ester; It is characterized in that: with dimethyl sebacate, 1,2,2,6,6-pentamethyl--4-hydroxy piperidine is a raw material; Under the condition of solvent and catalyzer existence, 100～120 ℃ of reactions down, the reaction times is 2h, and reaction is filtered, washed after finishing; Tell organic layer, in the organic layer solution of telling, dewater, decolouring, precipitation get sebacic acid two (1,2,2,6; 6-pentamethyl--4-piperidyl) ester, said solvent is a sherwood oil, the catalyzer of said transesterification reaction is activated carbon supported tetra isopropyl titanate, said dimethyl sebacate, 1; 2,2,6, the usage ratio of 6-pentamethyl--4-hydroxy piperidine, catalyzer, solvent is counted by quality: dimethyl sebacate: 1; 2,2,6,6-pentamethyl--4-hydroxy piperidine: catalyzer: solvent=1: 1.4～2.2: 0.03～0.15: 1.6～2.0.
2. the working method of photostabilizer sebacic acid two according to claim 1 (1,2,2,6,6-pentamethyl--4-piperidyl) ester, it is characterized in that: the catalyzer of said transesterification reaction can be reused 4～8 times.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010100172029A CN101768104B (en) | 2010-01-04 | 2010-01-04 | Method for producing light stabilizer sebacic acid (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) diester |
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| CN2010100172029A CN101768104B (en) | 2010-01-04 | 2010-01-04 | Method for producing light stabilizer sebacic acid (1, 2, 2, 6, 6-pentamethyl-4-piperidyl) diester |
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| CN101768104B true CN101768104B (en) | 2012-07-25 |
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| DE102016212379A1 (en) | 2016-07-07 | 2018-01-11 | Evonik Degussa Gmbh | Process for the preparation of an N-methyl-substituted triacetoneamine compound |
| CN110396060A (en) * | 2019-07-12 | 2019-11-01 | 西安工业大学 | A kind of light stabilizer and preparation method thereof containing double hindered piperidine bases |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4021432A (en) * | 1971-11-30 | 1977-05-03 | Ciba-Geigy Corporation | Piperidine derivatives |
| CN1347937A (en) * | 2000-10-09 | 2002-05-08 | 奇钛科技有限公司 | Composition containing piperidine derivative |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4021432A (en) * | 1971-11-30 | 1977-05-03 | Ciba-Geigy Corporation | Piperidine derivatives |
| CN1347937A (en) * | 2000-10-09 | 2002-05-08 | 奇钛科技有限公司 | Composition containing piperidine derivative |
Non-Patent Citations (6)
| Title |
|---|
| 􀦞 |
| 􁟤 |
| 􁟤􀦞.《中国博士学位论文》.2009,33-38. * |
| .《中国博士学位论文》.2009,33-38. |
| 刘军生.受阻胺类光稳定剂Tinuvin765的合成工艺研究.《广州化工》.2009,第37卷(第3期),136-138. * |
| 邓义.受阻胺类光稳定剂的设计、合成及表征􀧜 * |
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