CN103193724B - A kind of UV light absorber 2, the preparation method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol - Google Patents
A kind of UV light absorber 2, the preparation method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol Download PDFInfo
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Abstract
The invention discloses a kind of UV light absorber 2, the preparation method of 2 ˊ-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, after o-Nitraniline diazotization, with 2,2 '-methylene radical two (4-TBP) carries out coupled reaction, carry out reduction ring-closure reaction again, obtain product 2,2 ˊ-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol.The present invention's o-Nitraniline, 2; 2 '-methylene radical two (4-TBP) is Material synthesis 2; 2 ˊ-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, separating-purifying process is simple, and the reaction times is short; product yield is high; obtain product purity high, energy consumption is low, and environmental pollution is little; cost is low, is applicable to large-scale industrial and produces.
Description
Technical field
The present invention relates to a kind of UV light absorber 2, the preparation method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol.
Background technology
UV light absorber 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is a kind of macromolecular material effective UV light absorbers.Volatility is very low, good with the consistency of many polymkeric substance, be applicable to acrylate, polyester, polycarbonate, polyoxymethylene, polymeric amide, polyolefine, styrenic polymer, elastomerics, tackiness agent etc., be specially adapted to the processing and the aging condition that need high density, low volatility and good consistency.
At present, the domestic disclosed research report of synthetic method about 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is few.Now with 2,2 '-methylene radical two (4-TBP), o-Nitraniline are raw material, 2 have been synthesized, 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol through diazotization, coupling, reduction closed loop and acidification reaction.It is short that this method has the reaction times, and temperature of reaction is low, and aftertreatment is simple, the feature that product yield is higher.
Summary of the invention
The object of the present invention is to provide the UV light absorber 2 that a kind of product yield is high, the preparation method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol.
Technical solution of the present invention is:
A kind of UV light absorber 2, the preparation method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, o-Nitraniline obtains Compound II per through diazotization reaction, Compound II per and 2,2 '-methylene radical two (4-TBP) carries out coupled reaction and obtains compound III, compound III and reductive agent carry out reduction ring-closure reaction and obtain compound IV, compound IV obtains 2 after carrying out acidification reaction, 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol.
Structural formula and each step reaction formula of described Compound I, Compound II per, compound III and compound IV are as follows:
diazotization reaction
coupled reaction
reduction ring-closure reaction
acidification reaction
Described 2, the preparation method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, comprising:
Steps A: diazotization reaction
First mixed by the mixing solutions of o-Nitraniline with water and hydrochloric acid, then drip the mixing solutions of Sodium Nitrite and water, wherein the mass ratio of water and hydrochloric acid is 10:1-3, the mass ratio of Sodium Nitrite and water is 1:1-3, reaction 1-3 hour, temperature of reaction 0-3 DEG C, obtain the solution containing Compound II per;
Step B: coupled reaction
2,2 '-methylene radical two (4-TBP) first adds in buck, the weight ratio of water and alkali is 10:1-3, drips the solution of the steps A gained of 50% weight, then after the alkali adding quality 1-3 part, continue the solution of the steps A gained dripping residue 50% weight, dropping terminates rear reaction 2-6 hour, temperature of reaction 0-3 DEG C, adds water and hydrochloric acid and carries out acid out suction filtration and dry and obtain compound III, the weight ratio of water and hydrochloric acid is 10:0.7-2.5, and alkali is sodium carbonate or salt of wormwood;
Step C: reduction ring-closure reaction
Slowly compound III is added in the mixing solutions of water and alkali, and then add reductive agent in batches and carry out the solution that reduction reaction obtains containing compound IV, add reductive agent again, temperature of reaction 60-80 DEG C, terminates rear continuation reaction 3-6h, pours in trash ice rapidly by reaction solution, the solution containing compound IV is obtained after cooling, wherein the mass ratio of water and alkali is 10:1-4, and alkali is sodium hydroxide or potassium hydroxide, and reductive agent is hydrazine hydrate, thiourea peroxide or vat powder;
Step D: acidification reaction
The mixing solutions of water and acid is slowly dripped in the solution of step C, carry out acidification reaction and generate 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is also separated out, suction filtration obtains 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, wherein the weight ratio of water and acid is 10:1-3.5, and acid is hydrochloric acid, sulfuric acid;
Raw materials quality is than being o-Nitraniline: Sodium Nitrite: 2,2 '-methylene radical two (4-TBP): reductive agent: hydrochloric acid=1:0.5-0.8:1.2-1.7:3.1-4.7:0.25-0.5.
Described 2, in the steps A of the synthetic method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, the water consumption of 1g o-Nitraniline is 3-10g.
Described 2, be directly used in next step reaction after the reacting liquid filtering in the steps A of the synthetic method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol.
Described 2, in the step B of the synthetic method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, the sodium carbonate amount of 1g o-Nitraniline is 1-3g, and hydrochloric acid consumption is 0.7-2.5g.
The coupling compound III of described 2, the step B of the synthetic method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is directly used in next step reaction without the need to purifying.
In process of cooling after the reduction reaction of described 2, the step C of the synthetic method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol terminates, cooling temperature is not less than 0 DEG C.
The present invention is with 2,2 '-methylene radical two (4-TBP), o-Nitraniline are Material synthesis 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, and separating-purifying process is simple, reaction times is short, product yield is high, makes the yield of product reach more than 92%, obtains product purity higher, energy consumption reduces, environmental pollution is little, and cost is low, is the comparatively ideal technique realizing preparation of industrialization.
embodiment:
In order to deepen the understanding of the present invention, below in conjunction with embodiment, the invention will be further described, and this embodiment only for explaining the present invention, does not form limiting the scope of the present invention.
A kind of UV light absorber 2, the preparation method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, with 3-(3,5-di-tert-butyl-hydroxy phenyl)] methyl propionate, 1, the pyridine of 4-butyleneglycol is raw material, 2 have been synthesized, 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol through diazotization, coupling, reduction closed loop and acidification reaction.O-Nitraniline, Sodium Nitrite, 2, the usage ratio of 2 '-methylene radical two (4-TBP), reductive agent is by mass: o-Nitraniline: Sodium Nitrite: 2,2 '-methylene radical two (4-TBP): reductive agent: hydrochloric acid=1:0.5 ~ 0.8:1.2 ~ 1.7:3.1 ~ 4.7:0.25-0.5.
Embodiment 1:
Be o-Nitraniline in mass ratio: Sodium Nitrite: 2,2 '-methylene radical two (4-TBP): reductive agent: hydrochloric acid=1:0.55:1.3:3.4:0.3 reacts as follows:
In the aqueous hydrochloric acid prepared, vigorous stirring, then slowly adds 41.4g o-Nitraniline, after stirred at ambient temperature 30min, cools the temperature to 0-3 DEG C.Take Sodium Nitrite, be dissolved in 25g water, slowly drip above-mentioned solution, and temperature of reaction is remained on 0-3 DEG C, drip rear continuation reaction 2h, obtain the faint yellow diazonium salt solution containing Compound II per.
Take 2,2 '-methylene radical two (4-TBP), in 500mL flask, adds water and sodium carbonate, vigorous stirring, cools the temperature to 0-3 DEG C, slowly drips the diazonium salt solution of half amount wherein; Add the sodium carbonate of equivalent after dripping off again, continue the diazonium salt solution slowly dripping second half amount, drip rear continuation reaction 3h, and make temperature remain on 0-3 DEG C.By its acid out, suction filtration, pickling, oven dry after reaction terminates, obtain compound III.
In 250mL there-necked flask, add water and sodium hydroxide, vigorous stirring, slowly add above-claimed cpd III, temperature is risen to 70 DEG C simultaneously, add hydrazine hydrate in batches, about 30min adds, and temperature is risen to 80 DEG C, continues reaction 4h.After question response terminates, rapidly reaction solution is poured in trash ice, after cooling, obtain the solution containing compound IV.
To containing slowly dripping hydrochloric acid soln in the solution of compound IV by its acidifying, and rapid stirring, generate 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is also separated out, suction filtration, oven dry, product yield is 92.63%, HPLC detection level >=99%.
Embodiment 2:
Be o-Nitraniline in mass ratio: Sodium Nitrite: 2,2 '-methylene radical two (4-TBP): reductive agent: hydrochloric acid=1:0.65:1.4:3.7:0.35 reacts as follows:
In the aqueous hydrochloric acid prepared, vigorous stirring, then slowly adds 41.4g o-Nitraniline, after stirred at ambient temperature 30min, cools the temperature to 0-3 DEG C.Take Sodium Nitrite, be dissolved in 26.9g water, slowly drip above-mentioned solution, and temperature of reaction is remained on 0-3 DEG C, drip rear continuation reaction 3h, obtain the faint yellow diazonium salt solution containing Compound II per.
Take 2,2 '-methylene radical two (4-TBP), in 500mL flask, adds water and sodium carbonate, vigorous stirring, cools the temperature to 0-3 DEG C, slowly drips the diazonium salt solution of half amount wherein; Add the sodium carbonate of equivalent after dripping off again, continue the diazonium salt solution slowly dripping second half amount, drip rear continuation reaction 4h, and make temperature remain on 0-3 DEG C.By its acid out, suction filtration, pickling, oven dry after reaction terminates, obtain compound III.
In 250mL there-necked flask, add water and sodium hydroxide, vigorous stirring, slowly add above-claimed cpd III, temperature is risen to 70 DEG C simultaneously, add hydrazine hydrate in batches, about 30min adds, and temperature is risen to 80 DEG C, continues reaction 3h.After question response terminates, rapidly reaction solution is poured in trash ice, after cooling, obtain the solution containing compound IV.
To containing slowly dripping hydrochloric acid soln in the solution of compound IV by its acidifying, and rapid stirring, generate 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is also separated out, suction filtration, oven dry, product yield is 93.05%, HPLC detection level >=99%.
Embodiment 3:
Be o-Nitraniline in mass ratio: Sodium Nitrite: 2,2 '-methylene radical two (4-TBP): reductive agent: hydrochloric acid=1:0.7:1.5:4:0.4 reacts as follows:
In the aqueous hydrochloric acid prepared, vigorous stirring, then slowly adds 41.4g o-Nitraniline, after stirred at ambient temperature 30min, cools the temperature to 0-3 DEG C.Take Sodium Nitrite, be dissolved in 29g water, slowly drip above-mentioned solution, and temperature of reaction is remained on 0-3 DEG C, drip rear continuation reaction 3h, obtain the faint yellow diazonium salt solution containing Compound II per.
Take 2,2 '-methylene radical two (4-TBP), in 500mL flask, adds water and sodium carbonate, vigorous stirring, cools the temperature to 0-3 DEG C, slowly drips the diazonium salt solution of half amount wherein; Add the sodium carbonate of equivalent after dripping off again, continue the diazonium salt solution slowly dripping second half amount, drip rear continuation reaction 4h, and make temperature remain on 0-3 DEG C.By its acid out, suction filtration, pickling, oven dry after reaction terminates, obtain compound III.
In 250mL there-necked flask, add water and sodium hydroxide, vigorous stirring, slowly add above-claimed cpd III, temperature is risen to 70 DEG C simultaneously, add hydrazine hydrate in batches, about 30min adds, and temperature is risen to 80 DEG C, continues reaction 4h.After question response terminates, rapidly reaction solution is poured in trash ice, after cooling, obtain the solution containing compound IV.
To containing slowly dripping hydrochloric acid soln in the solution of compound IV by its acidifying, and rapid stirring, generate 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is also separated out, suction filtration, oven dry, product yield is 92.81%, HPLC detection level >=99%.
Embodiment 4:
Be o-Nitraniline in mass ratio: Sodium Nitrite: 2,2 '-methylene radical two (4-TBP): reductive agent: hydrochloric acid=1:0.75:1.5:4.2:0.45 reacts as follows:
In the aqueous hydrochloric acid prepared, vigorous stirring, then slowly adds 41.4g o-Nitraniline, after stirred at ambient temperature 30min, cools the temperature to 0-3 DEG C.Take Sodium Nitrite, be dissolved in 31g water, slowly drip above-mentioned solution, and temperature of reaction is remained on 0-3 DEG C, drip rear continuation reaction 2h, obtain the faint yellow diazonium salt solution containing Compound II per.
Take 2,2 '-methylene radical two (4-TBP), in 500mL flask, adds water and sodium carbonate, vigorous stirring, cools the temperature to 0-3 DEG C, slowly drips the diazonium salt solution of half amount wherein; Add the sodium carbonate of equivalent after dripping off again, continue the diazonium salt solution slowly dripping second half amount, drip rear continuation reaction 6h, and make temperature remain on 0-3 DEG C.By its acid out, suction filtration, pickling, oven dry after reaction terminates, obtain compound III.
In 250mL there-necked flask, add water and sodium hydroxide, vigorous stirring, slowly add above-claimed cpd III, temperature is risen to 70 DEG C simultaneously, add hydrazine hydrate in batches, about 30min adds, and temperature is risen to 80 DEG C, continues reaction 5h.After question response terminates, rapidly reaction solution is poured in trash ice, after cooling, obtain the solution containing compound IV.
To containing slowly dripping hydrochloric acid soln in the solution of compound IV by its acidifying, and rapid stirring, generate 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is also separated out, suction filtration, oven dry, product yield is 93.37%, HPLC detection level >=99%.
Embodiment 5:
Be o-Nitraniline in mass ratio: Sodium Nitrite: 2,2 '-methylene radical two (4-TBP): reductive agent: hydrochloric acid=1:0.7:1.7:4.5:0.5 reacts as follows:
In the aqueous hydrochloric acid prepared, vigorous stirring, then slowly adds 41.4g o-Nitraniline, after stirred at ambient temperature 30min, cools the temperature to 0-3 DEG C.Take Sodium Nitrite, be dissolved in 29g water, slowly drip above-mentioned solution, and temperature of reaction is remained on 0-3 DEG C, drip rear continuation reaction 3h, obtain the faint yellow diazonium salt solution containing Compound II per.
Take 2,2 '-methylene radical two (4-TBP), in 500mL flask, adds water and sodium carbonate, vigorous stirring, cools the temperature to 0-3 DEG C, slowly drips the diazonium salt solution of half amount wherein; Add the sodium carbonate of equivalent after dripping off again, continue the diazonium salt solution slowly dripping second half amount, drip rear continuation reaction 5h, and make temperature remain on 0-3 DEG C.By its acid out, suction filtration, pickling, oven dry after reaction terminates, obtain compound III.
In 250mL there-necked flask, add water and sodium hydroxide, vigorous stirring, slowly add above-claimed cpd III, temperature is risen to 70 DEG C simultaneously, add hydrazine hydrate in batches, about 30min adds, and temperature is risen to 80 DEG C, continues reaction 6h.After question response terminates, rapidly reaction solution is poured in trash ice, after cooling, obtain the solution containing compound IV.
To containing slowly dripping hydrochloric acid soln in the solution of compound IV by its acidifying, and rapid stirring, generate 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is also separated out, suction filtration, oven dry, product yield is 92.09%, HPLC detection level >=99%.
The present invention is with 2,2 '-methylene radical two (4-TBP), o-Nitraniline are Material synthesis 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, and separating-purifying process is simple, reaction times is short, product yield is high, makes the yield of product reach more than 92%, obtains product purity higher, energy consumption reduces, environmental pollution is little, and cost is low, is the comparatively ideal technique realizing preparation of industrialization.
Claims (1)
1. a UV light absorber 2, the preparation method of 2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, it is characterized in that: o-Nitraniline diazotization reaction is obtained Compound II per, the structural formula of described Compound II per is
, described Compound II per and 2,2 '-methylene radical two (4-TBP) carries out coupled reaction and obtains compound III, and the structural formula of described compound III is
, described compound III is carried out reduction ring-closure reaction and is obtained compound IV, and the structural formula of described compound IV is
, compound IV is carried out acidification reaction and is obtained Compound I, and described Compound I is target product 2,2'-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, and structural formula is
;
Concrete grammar step comprises:
Steps A: diazotization reaction
First mixed by the mixing solutions of o-Nitraniline with water and hydrochloric acid, then drip the mixing solutions of Sodium Nitrite and water, wherein the mass ratio of water and hydrochloric acid is 10:1-3, the mass ratio of Sodium Nitrite and water is 1:1-3, reaction 1-3 hour, temperature of reaction 0-3 DEG C, obtain the solution containing Compound II per;
Step B: coupled reaction
2,2 '-methylene radical two (4-TBP) first adds in buck, the weight ratio of water and alkali is 10:1-3, drip the solution of the steps A gained of 50% weight, then after the alkali adding quality 1-3 part, continue the solution of the steps A gained dripping residue 50% weight, dropping terminates rear reaction 2-6 hour, temperature of reaction 0-3 DEG C, add water and hydrochloric acid and carry out acid out suction filtration and dry and obtain compound III, the weight ratio of water and hydrochloric acid is 10:0.7-2.5; Alkali is sodium carbonate or salt of wormwood;
Step C: reduction ring-closure reaction
Slowly compound III is added in the mixing solutions of water and alkali, and then add reductive agent in batches and carry out the solution that reduction reaction obtains containing compound IV, add reductive agent again, temperature of reaction 60-80 DEG C, reaction 3-6h is continued after terminating, pour in trash ice by reaction solution rapidly, obtain the solution containing compound IV after cooling, wherein the mass ratio of water and alkali is 10:1-4; Alkali is sodium hydroxide or potassium hydroxide; Reductive agent is hydrazine hydrate, thiourea peroxide or vat powder;
Step D: acidification reaction
The mixing solutions of water and hydrochloric acid is slowly dripped in the solution of step C, carry out acidification reaction and generate 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol is also separated out, suction filtration obtains 2,2 '-methylene radical two [6-(2H-benzotriazole-2-the base)-4-tertiary butyl] phenol, wherein the weight ratio of water and hydrochloric acid is 10:1-3.5; Raw materials quality is than being o-Nitraniline: Sodium Nitrite: 2,2 '-methylene radical two (4-TBP): reductive agent: hydrochloric acid=1:0.5-0.8:1.2-1.7:3.1-4.7:0.25-0.5.
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| US5808086A (en) * | 1996-07-31 | 1998-09-15 | Johoku Chemical Co., Ltd. | Process for preparing bis (2-hydroxyphenyl-3-benztriazole) methanes |
| WO2002012202A2 (en) * | 2000-08-03 | 2002-02-14 | Ciba Specialty Chemicals Holdings Inc. | Processes for the preparation of benzotriazole uv absorbers |
| CN1599777A (en) * | 2001-12-05 | 2005-03-23 | 西巴特殊化学品控股有限公司 | Organic solvent-free process for the preparation of 2-(2-nitrophenylazo)phenols |
| CN101497562A (en) * | 2009-02-24 | 2009-08-05 | 南通惠康国际企业有限公司 | Method for producing light-stability agent benzophenone |
| CN102295613A (en) * | 2010-06-25 | 2011-12-28 | 吉林师范大学 | Method for preparing 2-(2'-hydroxyl 5'-tert-octyl phenyl)benzotriazole |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5808086A (en) * | 1996-07-31 | 1998-09-15 | Johoku Chemical Co., Ltd. | Process for preparing bis (2-hydroxyphenyl-3-benztriazole) methanes |
| WO2002012202A2 (en) * | 2000-08-03 | 2002-02-14 | Ciba Specialty Chemicals Holdings Inc. | Processes for the preparation of benzotriazole uv absorbers |
| CN1599777A (en) * | 2001-12-05 | 2005-03-23 | 西巴特殊化学品控股有限公司 | Organic solvent-free process for the preparation of 2-(2-nitrophenylazo)phenols |
| CN101497562A (en) * | 2009-02-24 | 2009-08-05 | 南通惠康国际企业有限公司 | Method for producing light-stability agent benzophenone |
| CN102295613A (en) * | 2010-06-25 | 2011-12-28 | 吉林师范大学 | Method for preparing 2-(2'-hydroxyl 5'-tert-octyl phenyl)benzotriazole |
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