CN101570507A - Preparation process of bis (n-octyloxy-2, 2,6, 6-tetramethylpiperidyl) sebacate - Google Patents
Preparation process of bis (n-octyloxy-2, 2,6, 6-tetramethylpiperidyl) sebacate Download PDFInfo
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- CN101570507A CN101570507A CNA2008100254267A CN200810025426A CN101570507A CN 101570507 A CN101570507 A CN 101570507A CN A2008100254267 A CNA2008100254267 A CN A2008100254267A CN 200810025426 A CN200810025426 A CN 200810025426A CN 101570507 A CN101570507 A CN 101570507A
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- Prior art keywords
- octane
- octyloxy
- sebacate
- bis
- tetramethyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- -1 bis (n-octyloxy-2, 2,6, 6-tetramethylpiperidyl) sebacate Chemical compound 0.000 title claims abstract description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 20
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000005516 engineering process Methods 0.000 claims description 8
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 5
- 239000004611 light stabiliser Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 2
- GMMWDNXVZHDCMW-UHFFFAOYSA-N decanedioic acid;2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1.CC1(C)CCCC(C)(C)N1.OC(=O)CCCCCCCCC(O)=O GMMWDNXVZHDCMW-UHFFFAOYSA-N 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 238000011160 research Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229920005669 high impact polystyrene Polymers 0.000 description 2
- 239000004797 high-impact polystyrene Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 1
- 235000005291 Rumex acetosa Nutrition 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002103 nanocoating Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Abstract
The invention relates to a preparation process of a hindered amine light stabilizer, in particular to a process for preparing bis (n-octyloxy-2, 2,6, 6-tetramethylpiperidyl) sebacate by taking bis (2, 2,6, 6-tetramethylpiperidine) sebacate, 70 percent of tert-butyl hydroperoxide and n-octane as basic raw materials and adding a certain amount of catalyst. The method is characterized in that the molar ratio of 70% of tert-butyl hydroperoxide to bis (2, 2,6, 6-tetramethylpiperidine) sebacate is not less than 7: 1, preferably 7-10: 1; adding catalyst, reflux reacting in sufficient n-octane solvent, and distilling to eliminate most of n-octane to obtain the product. The invention has the advantages of no three wastes basically in the production process, simple reaction operation and convenient industrial production.
Description
Technical field
The present invention relates to a kind of preparation technology of hindered amine as light stabilizer, specifically be a kind of with sebacic acid two (2,2,6, the 6-tetramethyl piperidine) ester and 70% tertbutyl peroxide and octane are that basic raw material adds the two (n-octyloxies-2 of a certain amount of Preparation of Catalyst, 2,6,6-tetramethyl-piperidyl) technology of sebate.
Background technology
Two (n-octyloxy-2,2,6,6-tetramethyl-piperidyl) sebate is a kind of non-alkaline hindered amine as light stabilizer product of N-substituted alcoxyl based structures, can be widely used in High Impact Polystyrene (HIPS), family expenses plastics film and coating products.Hindered amine light stabilizer (HALS) becomes the main flow of photostabilizer consumption market in the synthetic material auxiliary agent, dominate in world's photostabilizer market comsupton structure because its superior performance has replaced traditional photostabilizer kind.Along with the fundamental research of photostabilizer and deepening continuously of applied research, the range of application of HA LS constantly enlarges.At present, the application of HALS has been contained in the various fields such as plastic sheeting for farm use, engineering plastics, fiber, high-molecular coating, artificial carpet and outdoor various plastics, since phase late 1970s, Mitsui company and former Switzerland Ciba-Geigy company have released since the Tinuvin700 first, HALS is the research focus in Photostabilised field always, its efficiently mechanism of light stabilizer be the problem that the various countries investigator pays close attention to always.
The research of China HALS is started in 1974, and first releases multifunctional type HALS kind GW-540 the Shaanxi chemical institute, and many subsequently research units adopt and develop and copy the strategy that external leading brand combines voluntarily and add the research and development ranks in succession.Imitated SanolLS-744 of Beijing auxiliary chemicals institute and SanolLS-770 are named capital-5 and capital-6, and wherein applied range, the influence with capital 6 is big.The PDS that Chinese Academy of Sciences's chemistry is released is the aggretion type HALS of independent development.China HALS manufacturer mainly contains Hua Shan auxiliary reagent factory, Beijing (now being Beijin Tiangang Auxiliary Co., Ltd.), Shanxi chemical research institute, chemical plant, Ruian, Shanghai Petroleum Chemical Engineering Institute and chemistry institute of the Chinese Academy of Sciences.
At present, China HALS manufacturing enterprise scale is less than normal, and production of less types can not adapt to the development of the polymeric material industry of domestic rapid growth.Each enterprise all starts with from the production of triacetonamine, certainly will cause macro effect low, and has the of less types of excellent properties among the HALS that produces, and the ability to ward off risks is poor, and along with the raising of environmental protection and hygienic standard, the some of them kind will be eliminated gradually.
Because traditional HALS is alkalescence, has limited its range of application, be not suitable for acid environments for use such as Halogen and sulphur resin, acid coating, acid Synergist S-421 95 such as it.Be the expanded application field, the method that reduces alkalescence is to replace free amino, and substituting group is alkyl, oxygen base and acyloxy etc.Two (n-octyloxy-2,2,6,6-tetramethyl-piperidyl) sebates that company now releases are exactly to replace the hydrogen atom on the nitrogen with-OC8H17, become the amidogen ether that is obstructed on the structure, and it can mix mutually with acidic medium.
Summary of the invention
The technical issues that need to address of the present invention are exactly to replace hydrogen atom on the nitrogen with-OC8H17, become the amidogen ether that is obstructed on the structure, and reaction process is simple, the yield height.
Two (n-octyloxy-2 of the present invention, 2,6, the 6-tetramethyl-piperidyl) preparation technology of sebate is characterized in that 70% tertbutyl peroxide: sebacic acid two (2,2,6, the 6-tetramethyl piperidine) mol ratio of ester 〉=7: 1, adding catalyzer is abundant back flow reaction under the solvent at the q.s octane, distillation is removed most of octane and is got product.Because t-butyl hydrogen peroxide is a liquid, so control easily, compare safety with the mode that drips, the dropping time is 6 hours usually.
As preferably, described 70% tertbutyl peroxide: the mol ratio of two (2,2,6, the 6-tetramethyl piperidine) esters of sebacic acid is 7～10: 1.Experimental results show that to be less than this ratio, reaction can not be complete, and product color is poor.
As preferably, described solvent octane: the mol ratio of two (2,2,6, the 6-tetramethyl piperidine) esters of sebacic acid is 25～20: 1, experimental results show that to be less than this ratio that speed of response is slow.
Advantage of the present invention is that speed of response is very fast relatively, and product color is good, and reaction process is simple, the industrial equipment less investment, and also reaction does not have three wastes generation substantially.
Embodiment
Example 1
In the four-hole boiling flask that reflux exchanger, water trap are housed, add sebacic acid two (2,2,6, the 6-tetramethyl piperidine) ester 76 grams, 450 milliliters of octanes add little amount of catalyst, stirring is warmed up to 115 ℃, drip 70% t-butyl hydrogen peroxide, 140 grams, dripped off in 6 hours, water trap is constantly told the water of generation.Drip off and refluxed 5 hours, cooling is filtered, the elimination catalyzer, and filtrate adds 10 gram activated carbon again stirring at room 30 minutes, refilters, and the mother liquor underpressure distillation boils off octane and gets faint yellow finished product 93 grams, yield 80%.
Example 2
In the four-hole boiling flask that reflux exchanger, water trap are housed, add sebacic acid two (2,2,6, the 6-tetramethyl piperidine) ester 76 grams, 450 milliliters of octanes add little amount of catalyst, stirring is warmed up to 115 ℃, drip 70% t-butyl hydrogen peroxide, 100 grams, dripped off in 6 hours, water trap is constantly told the water of generation.Drip off and refluxed 5 hours, cooling is filtered, the elimination catalyzer, and filtrate adds 10 gram activated carbon again stirring at room 30 minutes, refilters, and the mother liquor underpressure distillation boils off octane and gets sorrel finished product 87 grams, yield 75%.
Claims (3)
1, a kind of two (n-octyloxy-2,2,6,6-tetramethyl-piperidyl) preparation technology of sebate, it is characterized in that with sebacic acid two (2,2,6,6-tetramethyl piperidine) ester and 70% tertbutyl peroxide and octane are basic raw material, 70% tertbutyl peroxide: sebacic acid two (2,2,6,6-tetramethyl piperidine) mol ratio of ester 〉=7: 1; Adding catalyzer is abundant back flow reaction under the solvent at the q.s octane, and distillation is removed most of octane and got product.
2, the preparation technology of two (n-octyloxy-2,2,6,6-tetramethyl-piperidyl) sebates according to claim 1 is characterized in that 70% tertbutyl peroxide: the mol ratio of two (2,2,6, the 6-tetramethyl piperidine) esters of sebacic acid is 7～10: 1.
3, the preparation technology of two (n-octyloxy-2,2,6,6-tetramethyl-piperidyl) sebates according to claim 1 and 2 is characterized in that the solvent for use octane: the mol ratio of two (2,2,6, the 6-tetramethyl piperidine) esters of sebacic acid is 25～20: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100254267A CN101570507A (en) | 2008-04-28 | 2008-04-28 | Preparation process of bis (n-octyloxy-2, 2,6, 6-tetramethylpiperidyl) sebacate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100254267A CN101570507A (en) | 2008-04-28 | 2008-04-28 | Preparation process of bis (n-octyloxy-2, 2,6, 6-tetramethylpiperidyl) sebacate |
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| Publication Number | Publication Date |
|---|---|
| CN101570507A true CN101570507A (en) | 2009-11-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008100254267A Pending CN101570507A (en) | 2008-04-28 | 2008-04-28 | Preparation process of bis (n-octyloxy-2, 2,6, 6-tetramethylpiperidyl) sebacate |
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| Country | Link |
|---|---|
| CN (1) | CN101570507A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702174A (en) * | 2012-06-19 | 2012-10-03 | 南通惠康国际企业有限公司 | Method for preparing light stabilizer tri(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-oxy-piperidyl)-1,3,5-triazine |
| CN103012251A (en) * | 2013-01-07 | 2013-04-03 | 南通惠康国际企业有限公司 | Preparation method of hindered amine light stabilizer intermediate compound 1-octoxy-2,2,6,6-tetramethyl-4-hydroxypiperidine |
| CN106699639A (en) * | 2016-12-22 | 2017-05-24 | 甘肃省化工研究院 | Synthesis method of light stabilizer HS-112 |
| CN107573280A (en) * | 2017-08-28 | 2018-01-12 | 新秀化学（烟台）有限公司 | A kind of synthetic method of double (piperidyl of 12,2,6,6 tetramethyl of octyloxy 4) sebacates |
| CN107721910A (en) * | 2017-08-28 | 2018-02-23 | 新秀化学（烟台）有限公司 | A kind of production technology of double (piperidyl of 12,2,6,6 tetramethyl of alkoxy 4) alkyl acid esters |
| CN107903207A (en) * | 2017-12-19 | 2018-04-13 | 烟台新秀化学科技股份有限公司 | It is double（2,2,6,6 tetramethyl-piperidyl of n-octyloxy）The post treatment method of sebacate |
| 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 |
| CN111056991A (en) * | 2019-12-16 | 2020-04-24 | 兰州精细化工有限责任公司 | Refining and purifying method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
-
2008
- 2008-04-28 CN CNA2008100254267A patent/CN101570507A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102702174A (en) * | 2012-06-19 | 2012-10-03 | 南通惠康国际企业有限公司 | Method for preparing light stabilizer tri(1-cyclohexyloxy-2,2,6,6-tetramethyl-4-oxy-piperidyl)-1,3,5-triazine |
| CN102702174B (en) * | 2012-06-19 | 2015-08-12 | 如东金康泰化学有限公司 | The preparation method of photostabilizer three (1-cyclohexyloxy-2,2,6,6-tetramethyl--4-oxygen base-piperidyl)-1,3,5-triazines |
| CN103012251A (en) * | 2013-01-07 | 2013-04-03 | 南通惠康国际企业有限公司 | Preparation method of hindered amine light stabilizer intermediate compound 1-octoxy-2,2,6,6-tetramethyl-4-hydroxypiperidine |
| CN103012251B (en) * | 2013-01-07 | 2015-01-07 | 南通大学 | Preparation method of hindered amine light stabilizer intermediate compound 1-octoxy-2,2,6,6-tetramethyl-4-hydroxypiperidine |
| CN106699639A (en) * | 2016-12-22 | 2017-05-24 | 甘肃省化工研究院 | Synthesis method of light stabilizer HS-112 |
| CN107573280A (en) * | 2017-08-28 | 2018-01-12 | 新秀化学（烟台）有限公司 | A kind of synthetic method of double (piperidyl of 12,2,6,6 tetramethyl of octyloxy 4) sebacates |
| CN107721910A (en) * | 2017-08-28 | 2018-02-23 | 新秀化学（烟台）有限公司 | A kind of production technology of double (piperidyl of 12,2,6,6 tetramethyl of alkoxy 4) alkyl acid esters |
| CN107573280B (en) * | 2017-08-28 | 2020-10-27 | 烟台新秀化学科技股份有限公司 | Synthesis method of bis (1-octyloxy-2, 2, 6, 6-tetramethyl-4-piperidyl) sebacate |
| CN107903207A (en) * | 2017-12-19 | 2018-04-13 | 烟台新秀化学科技股份有限公司 | It is double（2,2,6,6 tetramethyl-piperidyl of n-octyloxy）The post treatment method of sebacate |
| 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 |
| CN111056991A (en) * | 2019-12-16 | 2020-04-24 | 兰州精细化工有限责任公司 | Refining and purifying method of bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate |
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