CN108409637A - A kind of light stabilizer intermediate N- butyl -2,2, the preparation process of 6,6- tetramethyl -4- piperidinamines - Google Patents
A kind of light stabilizer intermediate N- butyl -2,2, the preparation process of 6,6- tetramethyl -4- piperidinamines Download PDFInfo
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- CN108409637A CN108409637A CN201810378003.7A CN201810378003A CN108409637A CN 108409637 A CN108409637 A CN 108409637A CN 201810378003 A CN201810378003 A CN 201810378003A CN 108409637 A CN108409637 A CN 108409637A
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- tetramethyl
- butyl
- piperidinamines
- light stabilizer
- butylamine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
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- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention discloses a kind of light stabilizer intermediate N butyl 2,2,6, the preparation process of 6 tetramethyl, 4 piperidinamine, triacetonamine is dissolved in excessive n-butylamine, under the action of metallic catalyst, logical hydrogen heating direct taps into row hydro-reduction amination and target product N butyl 2 is made, 2,6,6 tetramethyl, 4 piperidinamine.This technological process is simple, and any reaction medium is not added, and production capacity is big, and by-product is few, main material triacetonamine high conversion rate, and excessive auxiliary material n-butylamine is recyclable to be applied mechanically again.
Description
Technical field
The invention belongs to hindered amine light stabilizer fields, and in particular to a kind of light stabilizer intermediate N- butyl -2,2,6,
The preparation process of 6- tetramethyl -4- piperidinamines.
Background technology
Hindered amine light stabilizer intermediate N butyl -2,2,6,6- tetramethyl -4- piperidinamines be currently on the market be in great demand or
The most direct material of the light stabilizer 119 and light stabilizer 2020 that supply falls short of demand, its production capacity and cost also directly determine
The production capacity and cost of light stabilizer 119 and light stabilizer 2020.Light stabilizer 119 is acidproof low alkalinity currently on the market
The best light stabilizer of energy effect, and light stabilizer 2020 has high thermal stability and photostability, it may have it is very excellent
Plastics intermiscibility, addition will not influence the processing performances of plastics in the plastic, and outstanding is to apply to compile in plastic spinning
Knit industry.Therefore, this patent proposes a kind of novel synthesis light stabilizer intermediate N- butyl -2,2,6,6- tetramethyl -4-
The technique of piperidinamine, its value be exactly in order to higher efficiency, the production hindered amine light of lower cost and duration
Stablize 119 and 2020.
Invention content
The present invention provides a kind of light stabilizer intermediate N- butyl -2,2, the preparation works of 6,6- tetramethyl -4- piperidinamines
Skill, technological process is simple, and any reaction medium is not added, and production capacity is big, and by-product is few, main material triacetonamine high conversion rate, mistake
Auxiliary material n-butylamine is recyclable applies mechanically again for amount.
To solve the above-mentioned problems, the technical solution adopted in the present invention is such, a kind of light stabilizer intermediate N-
Butyl -2,2, the preparation process of 6,6- tetramethyl -4- piperidinamines, triacetonamine is dissolved in excessive n-butylamine, in metal catalytic
Under the action of agent, logical hydrogen heating direct taps into row hydro-reduction amination and target product N- butyl -2,2,6,6- tetramethyl -4- is made
Piperidinamine.
Preferably, in step 1), the mass ratio of triacetonamine and n-butylamine is 1:0.7~1.5；Further preferably 1:
0.9~1.0.
Specifically include following steps：
1) metallic catalyst is added in reactor, adds triacetonamine and n-butylamine, be sealed and carry out nitrogen displacement
Hydrogen is replaced again；
2) it after replacement completion, is passed through hydrogen to pressure and reaches 0.6~5.0MPa, start to warm up and stir, until 80~150
DEG C, heat-insulation pressure keeping reacts 2-8h；
3) after the reaction was complete, cooling, nitrogen displacing hydrogen filters, and filtrate carries out rectifying and can be obtained N- butyl -2,2,
6,6- tetramethyl -4- piperidinamines.
Preferably, in step 1), the metallic catalyst is Raney's nickel or skeleton cobalt, the dosage of metallic catalyst and three
The mass ratio of acetone amine is 0.1~0.4：1；Further preferably 0.2~0.25：1.
Preferably, in step 2), reaction Hydrogen Vapor Pressure is 0.8~1.5MP, and reaction temperature is 100~120 DEG C, when reaction
Between be 3-5h.
Preferably, in step 3), the filter residue for filtering gained is back to recycling in step 1).
In step 3), the filtrate for filtering gained is recycled to obtain n-butylamine to be back in step 1) and is applied mechanically through rectifying.
Advantageous effect：1, any reaction medium is not used in this technique, is directly added into reaction raw materials and catalyst, reduce at
This, while production capacity is also increased, and by-product is few, main material triacetonamine high conversion rate, only remains target product after reaction
With excessive n-butylamine, and excessive auxiliary material n-butylamine is recyclable applies mechanically again.
2, technological process is simple, and required equipment is few, easy to operation.
3, this technique unit consumption is low, easy post-processing, and the yield in the unit interval is high.
Figure of description
Fig. 1 is the gas chromatographic detection collection of illustrative plates of 1 reaction solution of embodiment；(wherein, n-butylamine, triacetonamine and butyl -2 N-,
It is respectively 2.763min, 7.107min and 11.143min that 2,6,6- tetramethyl -4- piperidinamines, which correspond to retention time)；
Fig. 2 is the gas chromatographic detection collection of illustrative plates of reaction solution of the embodiment 1 after rectifying；(N- butyl -2,2,6,6- tetramethyls
It is 11.527min that base -4- piperidinamines, which correspond to retention time)；
Fig. 3 is gas chromatographic detection collection of illustrative plates (wherein, isobutanol, n-butylamine, triacetonamine and the N- fourths of comparative example reaction solution
Base -2,2, it is respectively 2.423min, 2.707min that 6,6- tetramethyl -4- piperidinamines, which correspond to retention time, 7.190min and
12.110min)；
Fig. 4 is gas chromatographic detection collection of illustrative plates (N- butyl -2,2,6, the 6- tetramethyls-of reaction solution of the comparative example after rectifying
It is 11.410min that 4- piperidinamines, which correspond to retention time)；
Specific implementation mode
In order to deepen the understanding of the present invention, below in conjunction with embodiment, the invention will be further described, the embodiment
It is only used for explaining the present invention, be not intended to limit the scope of the present invention..
Embodiment 1
In the autoclave of 3L, the triacetonamine of 1000g and the n-butylamine of 700g is added, the catalyst of 100g, nitrogen is added
Gas and hydrogen are replaced respectively, after be passed through hydrogen pressure made in kettle to reach 0.6MP, start to warm up and stir, until 80 DEG C, and maintain in kettle
Hydrogen Vapor Pressure is not less than 0.6MP, and after reacting 8 hours, sample detection is qualified, and cooling filtering, filtrate rectifying steams excessive positive fourth
Amine, continue rectifying can be obtained purity be 99.2% N- butyl -2,2,6,6- tetramethyl -4- piperidinamines 1303g (, yield is
95.3%.
Embodiment 2
In the autoclave of 3L, the triacetonamine of 1000g and the n-butylamine of 800g is added, the catalyst of 150g, nitrogen is added
Gas and hydrogen are replaced respectively, after be passed through hydrogen pressure made in kettle to reach 0.8MP, start to warm up and stir, until 90 DEG C, and maintain in kettle
Hydrogen Vapor Pressure is not less than 0.8MP, and after reacting 6 hours, sample detection is qualified, and cooling filtering, filtrate rectifying steams excessive positive fourth
Amine continues rectifying and can be obtained N- butyl -2,2 that purity is 99.3%, 6,6- tetramethyl -4- piperidinamine 1312g, and yield is
95.9%.
Embodiment 3
In the autoclave of 3L, the triacetonamine of 1000g and the n-butylamine of 900g is added, the catalyst of 250g, nitrogen is added
Gas and hydrogen are replaced respectively, after be passed through hydrogen pressure made in kettle to reach 0.9MP, start to warm up and stir, until 100 DEG C, and maintain kettle
Interior Hydrogen Vapor Pressure is not less than 0.9MP, and after reaction 5 hours, sample detection is qualified, cooling filtering, filtrate rectifying, steam it is excessive just
Butylamine continues rectifying and can be obtained N- butyl -2,2 that purity is 99.3%, 6,6- tetramethyl -4- piperidinamine 1332g, and yield is
97.4%.
Embodiment 4
In the autoclave of 4L, the triacetonamine of 1000g and the n-butylamine of 1000g is added, the catalyst of 300g, nitrogen is added
Gas and hydrogen are replaced respectively, after be passed through hydrogen pressure made in kettle to reach 1.0MP, start to warm up and stir, until 105 DEG C, and maintain kettle
Interior Hydrogen Vapor Pressure is not less than 1.0MP, after reacting 4.5 hours, sample detection qualified (gas chromatographic detection the result is shown in Figure 1, analysis
The results are shown in Table 2, can be seen that by Fig. 1 and table 1, and triacetonamine residual only 0.1232% in reaction solution, thus says after reaction
Bright triacetonamine has almost reacted), cooling filtering, filtrate rectifying steams excessive n-butylamine, continues rectifying and can be obtained purity
For 99.9% N- butyl -2,2, (gas chromatographic detection result is shown in Fig. 2, analysis knot to 6,6- tetramethyl -4- piperidinamines 1324g
Fruit is as shown in table 2), yield 96.8%.
Table 1
Table 2
Embodiment 5
In the autoclave of 4L, the triacetonamine of 1000g and the n-butylamine of 1100g is added, the catalyst of 350g, nitrogen is added
Gas and hydrogen are replaced respectively, after be passed through hydrogen pressure made in kettle to reach 1.2MP, start to warm up and stir, until 105 DEG C, and maintain kettle
Interior Hydrogen Vapor Pressure is not less than 1.2MP, and after reaction 4 hours, sample detection is qualified, cooling filtering, filtrate rectifying, steam it is excessive just
Butylamine continues rectifying and can be obtained N- butyl -2,2 that purity is 99.5%, 6,6- tetramethyl -4- piperidinamine 1305g, and yield is
95.4%.
Embodiment 6
In the autoclave of 4L, the triacetonamine of 1000g and the n-butylamine of 1400g is added, the catalyst of 400g, nitrogen is added
Gas and hydrogen are replaced respectively, after be passed through hydrogen pressure made in kettle to reach 2.5MP, start to warm up and stir, until 125 DEG C, and maintain kettle
Interior Hydrogen Vapor Pressure is not less than 2.5MP, and after reacting 2.5 hours, sample detection is qualified, and cooling filtering, filtrate rectifying steams excessive
N-butylamine continues rectifying and can be obtained N- butyl -2,2 that purity is 99.6%, 6,6- tetramethyl -4- piperidinamine 1316g, yield
It is 96.2%.
Embodiment 7
In the autoclave of 4L, the triacetonamine of 1000g and the n-butylamine of 1500g is added, the catalyst of 400g, nitrogen is added
Gas and hydrogen are replaced respectively, after be passed through hydrogen pressure made in kettle to reach 3.5MP, start to warm up and stir, until 125 DEG C, and maintain kettle
Interior Hydrogen Vapor Pressure is not less than 3.5MP, and after reaction 2 hours, sample detection is qualified, cooling filtering, filtrate rectifying, steam it is excessive just
Butylamine continues rectifying and can be obtained N- butyl -2,2 that purity is 99.4%, 6,6- tetramethyl -4- piperidinamine 1324g, and yield is
96.8%.
Comparative example
In the autoclave of 4L, the triacetonamine of 1000g and the n-butylamine of 1000g is added, it is molten to add 500g isopropanols
The catalyst of 150g is added in agent, and nitrogen and hydrogen are replaced respectively, after be passed through hydrogen pressure made in kettle to reach 0.8MP, start to warm up simultaneously
Stirring, until 90 DEG C, and Hydrogen Vapor Pressure in kettle is maintained to be not less than 0.8MP, and after reacting 5 hours, (gas chromatographic detection after sample detection
As a result see Fig. 3, analysis result is as shown in table 3, can be seen that by Fig. 3 and table 3, and triacetonamine remains 0.374%, by-product 2,
2,6,6- tetramethyl -4- piperidine alcohols, corresponding retention time are 7.963min, and content up to 4.451%), filter by cooling, filtrate essence
It evaporates, steams solvent isobutanol and excessive n-butylamine, continue rectifying and remove 2,2,6,6- tetramethyl -4- piperidine alcohols of by-product, i.e.,
N- butyl -2,2 that purity is 97.09% can be obtained, (gas chromatographic detection result is shown in figure to 6,6- tetramethyl -4- piperidinamines 1216g
4, analysis result is as shown in table 4), yield 88.9%.
Table 3
Table 4
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
With within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention god.
Claims (9)
1. a kind of light stabilizer intermediate N- butyl -2,2, the preparation process of 6,6- tetramethyl -4- piperidinamines, which is characterized in that
Triacetonamine is dissolved in excessive n-butylamine, under the action of metallic catalyst, logical hydrogen heating direct taps into row hydro-reduction amine
Change and target product N- butyl -2,2,6,6- tetramethyl -4- piperidinamines are made.
2. a kind of light stabilizer intermediate N- butyl -2,2 according to claim 1, the system of 6,6- tetramethyl -4- piperidinamines
Standby technique, which is characterized in that the mass ratio of triacetonamine and n-butylamine is 1:0.7~1.5.
3. a kind of light stabilizer intermediate N- butyl -2,2 according to claim 2, the system of 6,6- tetramethyl -4- piperidinamines
Standby technique, which is characterized in that step 1）In, the mass ratio of triacetonamine and n-butylamine is 1:0.9~1.0.
4. a kind of light stabilizer intermediate N- butyl -2,2 according to claim 1, the system of 6,6- tetramethyl -4- piperidinamines
Standby technique, which is characterized in that specifically include following steps：
1）Metallic catalyst is added in reactor, triacetonamine and n-butylamine are added, is sealed and carries out nitrogen displacement hydrogen again
Gas is replaced；
2）After replacement completion, it is passed through hydrogen to pressure and reaches 0.6~5.0MPa, start to warm up and stir, until 80~150 DEG C, it protects
2-8h is reacted in warm pressurize；
3）After the reaction was complete, cooling, nitrogen displacing hydrogen filters, and filtrate carries out rectifying, steams excessive n-butylamine and is returned
After receipts, continues rectifying and can be obtained N- butyl -2,2,6,6- tetramethyl -4- piperidinamines.
5. a kind of light stabilizer intermediate N- butyl -2,2 according to claim 4, the system of 6,6- tetramethyl -4- piperidinamines
Standby technique, which is characterized in that step 1）In, the metallic catalyst is Raney's nickel or skeleton cobalt, the dosage of metallic catalyst
Mass ratio with triacetonamine is 0.1~0.4：1.
6. a kind of light stabilizer intermediate N- butyl -2,2 according to claim 5, the system of 6,6- tetramethyl -4- piperidinamines
Standby technique, which is characterized in that the dosage of metallic catalyst and the mass ratio of triacetonamine are 0.2~0.25：1.
7. a kind of light stabilizer intermediate N- butyl -2,2 according to claim 4, the system of 6,6- tetramethyl -4- piperidinamines
Standby technique, which is characterized in that step 2）In, reaction Hydrogen Vapor Pressure is 0.8~1.5MP, and reaction temperature is 100~120 DEG C, reaction
Time is 3-5h.
8. a kind of light stabilizer intermediate N- butyl -2,2 according to claim 4, the system of 6,6- tetramethyl -4- piperidinamines
Standby technique, which is characterized in that step 3）In, the filter residue for filtering gained is back to step 1）Middle recycling.
9. a kind of light stabilizer intermediate N- butyl -2,2 according to claim 4, the system of 6,6- tetramethyl -4- piperidinamines
Standby technique, which is characterized in that step 3）In, the filtrate for filtering gained recycles to obtain n-butylamine and is back to step 1 through rectifying）Middle set
With.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110317162A (en) * | 2019-07-26 | 2019-10-11 | 宿迁联盛科技股份有限公司 | Tetramethyl piperidine amine is continuously synthesizing to method and synthesizer |
| CN110922353A (en) * | 2019-11-07 | 2020-03-27 | 宿迁联盛科技股份有限公司 | Piperidine Schiff base synthesis and hydrogenation reduction method |
| EP3660001A1 (en) | 2018-11-27 | 2020-06-03 | Evonik Operations GmbH | Improved method for preparing triacetone diamine and its derivatives |
| US10807954B2 (en) | 2018-12-07 | 2020-10-20 | Evonik Operations Gmbh | Method for preparing triacetone amine |
| CN112239458A (en) * | 2020-10-20 | 2021-01-19 | 利安隆(天津)新材料科技有限公司 | Hindered amine light stabilizer intermediate and preparation method of hindered amine light stabilizer |
| CN113880752A (en) * | 2021-10-13 | 2022-01-04 | 江苏富比亚化学品有限公司 | Synthesis process of N-butyl-2, 2,6, 6-tetramethyl-4-piperidylamine |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3660001A1 (en) | 2018-11-27 | 2020-06-03 | Evonik Operations GmbH | Improved method for preparing triacetone diamine and its derivatives |
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| CN112239458A (en) * | 2020-10-20 | 2021-01-19 | 利安隆(天津)新材料科技有限公司 | Hindered amine light stabilizer intermediate and preparation method of hindered amine light stabilizer |
| CN113880752A (en) * | 2021-10-13 | 2022-01-04 | 江苏富比亚化学品有限公司 | Synthesis process of N-butyl-2, 2,6, 6-tetramethyl-4-piperidylamine |
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Application publication date: 20180817 |