CN113264927B - Synthesis method of dibenzoxazole fluorescent whitening agent and derivative thereof - Google Patents
Synthesis method of dibenzoxazole fluorescent whitening agent and derivative thereof Download PDFInfo
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Abstract
The invention provides a method for synthesizing a dibenzoxazole fluorescent whitening agent and derivatives thereof by using sodium periodate as an oxidizing agent and using catechol compounds, ammonium acetate and aryldicarboxaldehyde. The method has the characteristics of mild reaction conditions, no need of strong acid, strong alkali or metal catalyst, simple raw materials and the like. Meanwhile, sodium periodate is used as an oxidant, iodate generated after the reaction is finished can be well recovered, and pollution of heavy metal to the environment is avoided. The method mainly solves the problems of metal residue and complex raw material sources in the synthesis of the dibenzoxazole fluorescent whitening agent and the derivatives thereof, provides great convenience for the synthesis and application research of the dibenzoxazole fluorescent whitening agent and the derivatives thereof, and has great application value.
Description
[ technical field ] A method for producing a semiconductor device
The invention relates to the field of organic synthesis, in particular to a method for synthesizing a dibenzoxazole fluorescent whitening agent and a derivative thereof.
[ background of the invention ]
The dibenzoxazole fluorescent whitening agent is widely used for whitening thermoplastics, fibers, coatings, printing paints and the like, so that the treated articles have obvious gorgeous effect. The existing commercial bis-benzoxazole fluorescent whitening agent comprises a fluorescent whitening agent OB with good heat resistance, light resistance and chlorine bleaching resistance, a fluorescent whitening agent EBF with the light fastness of 7-8 grades, Uvitex 1980 with excellent sublimation resistance, a fluorescent whitening agent 367 with an extremely high whitening effect and the like.
At present, the synthesis research around the dibenzoxazole fluorescent whitening agent is mainly realized by the condensation reaction of an aryl dicarboxylic acid derivative and an o-aminophenol compound, however, the environment which we rely on for survival is seriously polluted by the high reaction temperature and/or the stoichiometric amount of strong acid or strong base required by the process, and the application of the fluorescent whitening agent of the type can be effectively promoted by searching a new strategy of atom and step economy. Catechol, a common structural motif of various natural products, bioactive molecules and drugs (over 30 thousands of compounds containing catechol components), can be synthesized from benzene or glucose by microbial catalysis. The annual yield of catechol is more than 3.0 × 107Kilogram, preparation of Complex building blocks and work Using catechol as substrateThe synthesis of energy molecules is of great significance. [ reference: (a) yun, g.g. -z.z. dyestiffs and Coloration 2011,1.(b) Ling, y.; feng, x.; he, j.f. analysis AND TESTING techlology AND INSTRUMENTS 1995,2.(c) MA, j. -x.; CHEN, B. Applied Chemical Industry 2007,7.(d) Song Brilliant mushroom; d, yellow valuable; weekend sail plastic adjuvant 2016, 47.(e) Wu, q.; yuan, z.; yang, x.; hu, q.; zhang, m.; zhong, y.applied Chemical Industry 2010,6.(f) Liang, y. -f.; li, X.; wang, x.; zuo, m.; tang, c.; liang, y.; song, s.; jiao, n.j.am.chem.soc.2016,138,12271.(g) Chen, x.; ji, f.; zhao, y.; liu, y.; zhou, y.; chen, t.; yin, s.f.adv.synth.catl.2015, 357, 2924.(h) Sharghi, h.; aboonajmi, j.; aberi, M.J.org.chem.2020,85,6567
Based on the background, an effective method for synthesizing the dibenzoxazole fluorescent whitening agent and the derivatives thereof by using the simple and easily obtained catechol compounds, ammonium acetate and aryl diformaldehyde as raw materials under simple reaction conditions is developed, and the method has important significance.
[ summary of the invention ]
The invention aims to develop a method for synthesizing a dibenzoxazole fluorescent whitening agent and derivatives thereof in a nitrogen atmosphere by taking catechol compounds, ammonium acetate and aryldialdehyde compounds as raw materials and under the action of sodium periodate serving as an oxidant at a high conversion rate.
The purpose of the invention is realized by the following technical scheme:
a method for synthesizing a dibenzoxazole fluorescent whitening agent and a derivative thereof comprises the following steps: catechols, ammonium acetate, aryldicarbaldehyde, and sodium periodate (NaIO)4)。
The dibenzoxazole fluorescent whitening agent and the derivative thereof have the following structural formula (I):
in the structural formula, R is a substituent at any one or more positions on a benzene ring, and each R is independently selected from methyl, tert-butyl and methoxy; ar is one of phenyl, naphthyl and thienyl.
The catechol compound is selected from one of 3, 5-di-tert-butyl catechol, p-tert-butyl catechol, 4-tert-butyl-5-methyl catechol and 3-methoxy catechol.
The aryl diformaldehyde is selected from one of 2, 5-thiophene diformaldehyde, 1, 4-benzene dicarbaldehyde, 1, 3-benzene dicarbaldehyde and 1, 4-naphthalene diformaldehyde.
Preferably, the synthesis method of the dibenzoxazole fluorescent whitening agent and the derivatives thereof comprises the following steps: taking catechol compound, ammonium acetate, aryl dicarbaldehyde and NaIO4Mixing; and adding a solvent in the inert gas atmosphere, and reacting to obtain the dibenzoxazole fluorescent whitening agent and the derivative thereof.
Further preferably, the synthesis method of the dibenzoxazole fluorescent whitening agent and the derivative thereof comprises the following steps: taking catechol compound, ammonium acetate, aryl dicarbaldehyde and NaIO4Mixing; adding a solvent in an inert gas atmosphere, heating and stirring for reaction, cooling to room temperature after the reaction is finished, washing with saturated NaCl, extracting, distilling under reduced pressure and concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the dibenzoxazole fluorescent whitening agent and the derivative thereof.
More preferably, the synthesis method of the dibenzoxazole fluorescent whitening agent and the derivative thereof comprises the following steps: taking catechol compound, ammonium acetate, aryl dicarbaldehyde and NaIO4Placing in a reaction vessel, and mixing; adding a solvent in an inert gas atmosphere, heating and stirring for reaction, cooling to room temperature after the reaction is finished, washing with saturated NaCl, extracting with ethyl acetate, distilling under reduced pressure and concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the dibenzoxazole fluorescent whitening agent and the derivative thereof.
The catechol compound, ammonium acetate, aryl dicarbaldehyde and NaIO4The molar ratio of (2.8-3.2)):(3.8～4.2):1:(1.8～2.2)。
Preferably, the catechols, ammonium acetate, aryldicarbaldehydes, NaIO4The molar ratio of (3-3.2) to (4-4.2) to (1) to (2-2.2).
More preferably, the catechols, ammonium acetate, aryldicarbaldehydes, NaIO4The molar ratio of the two is 3:4:1:2
The solvent is at least one of N, N-dimethylformamide, 1, 2-dichloroethane, acetonitrile, chloroform and ethyl acetate.
The temperature of the reaction is 50-100 ℃.
Preferably, the temperature of the reaction is 80 to 100 ℃.
The reaction time is 3-4 h.
Preferably, the reaction time is 3 h.
The inert gas is any one or combination of nitrogen, argon and helium.
According to experimental research, the invention provides a synthesis method for preparing a dibenzoxazole fluorescent whitening agent and derivatives thereof from catechol compounds, ammonium acetate and aryldialdehyde by using sodium periodate as an oxidizing agent. The method has the characteristics of mild reaction conditions, no need of strong acid, strong alkali or metal catalyst, simple raw materials and the like. Meanwhile, sodium periodate is used as an oxidant, and iodate generated after the reaction is finished can be well recovered, so that the problems of environmental pollution caused by heavy metal and metal residue in products are solved.
[ brief description of the drawings ]
FIG. 1 shows a reaction formula for preparing dibenzoxazole fluorescent whitening agents and derivatives thereof.
[ detailed description ] embodiments
The synthesis method of the present invention is further described below with reference to the synthesis examples of the present invention, which should be construed as limiting the scope of the present invention.
Synthesis method of dibenzoxazole fluorescent whitening agent and derivative thereof, and preparation method of dibenzoxazole fluorescent whitening agent and derivative thereofThe preparation method comprises the following raw materials: catechols, ammonium acetate, aryldicarbaldehyde, and sodium periodate (NaIO)4)。
The dibenzoxazole fluorescent whitening agent and the derivative thereof have the following structural formula:
in one embodiment, in the formula, R is a substituent at any one or more positions on the phenyl ring, and each R is independently selected from methyl, tert-butyl, methoxy; ar is one of phenyl, naphthyl and thienyl.
In one embodiment, the catechol compound is selected from one of 3, 5-di-tert-butyl catechol, p-tert-butyl catechol, 4-tert-butyl-5-methyl catechol, and 3-methoxy catechol.
In one embodiment, the aryldicarbaldehyde is selected from one of 2, 5-thiophenedicarboxaldehyde, 1, 4-benzenedicarboxaldehyde, 1, 3-benzenedicarboxaldehyde, and 1, 4-naphthalenedicarboxaldehyde.
In one embodiment, a method for synthesizing a dibenzoxazole fluorescent whitening agent and a derivative thereof comprises the following steps: taking catechol compound, ammonium acetate, aryl dicarbaldehyde and NaIO4Mixing; adding a solvent in an inert gas atmosphere, heating and stirring for reaction, cooling to room temperature after the reaction is finished, washing with saturated NaCl, extracting, distilling under reduced pressure and concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the dibenzoxazole fluorescent whitening agent and the derivative thereof.
In one embodiment, a method for synthesizing a dibenzoxazole fluorescent whitening agent and a derivative thereof comprises the following steps: taking catechol compound, ammonium acetate, aryl dicarbaldehyde and NaIO4Placing in a reaction vessel, and mixing; adding a solvent in an inert gas atmosphere, heating and stirring for reaction, cooling to room temperature after the reaction is finished, washing with saturated NaCl, extracting with ethyl acetate, distilling under reduced pressure and concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the dibenzoxazineAzole fluorescent whitening agents and derivatives thereof.
In one embodiment, the catechols, ammonium acetate, aryldicarbaldehydes, naios4The molar ratio of (2.8-3.2) to (3.8-4.2) to (1.8-2.2) is as follows.
In one embodiment, the catechols, ammonium acetate, aryldicarbaldehydes, naios4The molar ratio of the two is 3:4:1 (2-2.2).
In one embodiment, the solvent is one of N, N-dimethylformamide, 1, 2-dichloroethane, acetonitrile, chloroform, ethyl acetate.
In one embodiment, the temperature of the reaction is from 50 to 100 ℃.
In one embodiment, the temperature of the reaction is 80-100 ℃.
In one embodiment, the reaction time is 3 to 4 hours.
In one embodiment, the reaction time is 3 hours.
In one embodiment, the inert gas is any one or combination of nitrogen, argon and helium.
According to experimental research, the invention provides a synthesis method for preparing a dibenzoxazole fluorescent whitening agent and derivatives thereof from catechol compounds, ammonium acetate and aryldialdehyde by using sodium periodate as an oxidizing agent. The method has the characteristics of mild reaction conditions, no need of strong acid, strong alkali or metal catalyst, simple raw materials and the like. The method mainly solves the problems that metal residues and raw materials are not easy to obtain in the synthesis of the dibenzoxazole fluorescent whitening agent and the derivatives thereof, and is specifically represented as follows: (1) the method comprises the following steps of taking a simple and easily obtained catechol compound, ammonium acetate and aryl-dicarbaldehyde as raw materials, and smoothly synthesizing a dibenzoxazole fluorescent whitening agent with excellent practicability and derivatives thereof under the oxidation of sodium periodate; (2) the reaction avoids the use of transition metal and additives, and completely avoids the problem of heavy metal residue in the product; (3) the iodate after the reaction is finished can be well recycled, so that the pollution caused by a reaction system is greatly reduced, and the atom economy of the reaction is improved. The characteristics lead the industrial synthesis of the dibenzoxazole fluorescent whitening agent and the derivatives thereof to have potential value, and provide great convenience for the synthesis and application research of the dibenzoxazole fluorescent whitening agent and the derivatives thereof.
The following are specific synthesis examples.
Synthesis example 1
As shown in figure 1 of the drawings, in which,
synthesis of optical brightener OB
Adding 0.2mmol of p-tert-butylcatechol, 0.6mmol of 2, 5-thiophenedicarboxaldehyde, 0.8mmol of ammonium acetate and 0.4mmol of NaIO into a reactor42.0mL EA. Continuously stirring for 3h at 100 ℃ in the nitrogen atmosphere, stopping reaction, cooling to room temperature, washing with saturated NaCl, extracting with ethyl acetate, distilling under reduced pressure, concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the target product with a yield of 77%.1H NMR(400MHz,CDCl3):δ7.87(s,2H),7.78(s,2H),7.44(q,J＝8.5Hz,4H),1.39(s,18H).13C{1H}NMR(101MHz,CDCl3):δ158.1,148.6, 148.5,141.9,133.3,130.0,123.4,116.6,109.7,34.9,31.7.
Synthesis example 2
Synthesis of 1, 4-bis (5, 7-di-tert-butylbenzo [ d ] oxazol-2-yl) naphthalene
Adding 0.2mmol of 2, 4-di-tert-butyl catechol, 0.6mmol of 1, 4-dinaphthyl aldehyde, 0.8mmol of ammonium acetate and 0.4mmol of NaIO into a reactor42.0mL EA. Continuously stirring for 3h at 100 ℃ in the nitrogen atmosphere, stopping reaction, cooling to room temperature, washing with saturated NaCl, extracting with ethyl acetate, distilling under reduced pressure, concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the target product with the yield of 63%.1H NMR(400MHz,CDCl3):δ9.65–9.61(m,2H),8.52(s,2H),8.00– 7.59(m,4H),7.41–7.39(m,2H),1.60(s,18H),1.44(s,18H).13C{1H}NMR (101MHz,CDCl3):δ161.5,148.0,146.5,142.6,133.8,131.2,128.1,127.8,127.0, 126.8,120.2,114.7,35.2,34.6,31.9,30.1.
Synthesis example 3
Synthesis of 1, 4-bis (5- (tert-butyl) benzo [ d ] oxazol-2-yl) naphthalene
Adding 0.2mmol of p-tert-butylcatechol, 0.6mmol of 1, 4-dinaphthyl aldehyde, 0.8mmol of ammonium acetate and 0.4mmol of NaIO into a reactor42.0mL EA. Continuously stirring for 3h at 100 ℃ in the nitrogen atmosphere, stopping reaction, cooling to room temperature, washing with saturated NaCl, extracting with ethyl acetate, distilling under reduced pressure, concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the target product with the yield of 71%.1H NMR(400MHz,CDCl3):δ9.64–9.56(m,2H),8.50(s,2H),7.87– 7.74(m,4H),7.70(s,2H),7.50(d,J＝8.3Hz,2H),1.44(s,18H).13C{1H}NMR (101MHz,CDCl3):δ161.9,150.5,150.0,139.9,131.2,128.1,127.9,126.9,126.8, 122.5,119.6,107.3,35.3,31.7.
Synthesis example 4
Synthesis of 1, 4-bis (5, 7-di-tert-butylbenzo [ d ] oxazol-2-yl) benzene
Adding 0.4mmol of p-tert-butylcatechol, 0.4mmol of 1, 4-diphenylformaldehyde, 0.8mmol of ammonium acetate and 0.8mmol of NaIO into a reactor44.0mL EA. Continuously stirring for 3h at 50 ℃ in the nitrogen atmosphere, stopping reaction, cooling to room temperature, washing with saturated NaCl, extracting with ethyl acetate, distilling under reduced pressure, concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the target product with the yield of 72%.1H NMR(400MHz,CDCl3):δ8.41(s,4H),7.69(s,2H),7.35(s,2H), 1.58(s,18H),1.41(s,18H).13C{1H}NMR(101MHz,CDCl3):δ161.6,148.1, 147.1,142.3,133.9,129.8,127.8,120.1,114.4,35.2,34.6,31.8,30.1.
Synthesis example 5
Synthesis of 1,3, 5-tris (5, 7-di-tert-butylbenzo [ d ] oxazol-2-yl) benzene
Adding 0.6mmol of p-tert-butylcatechol, 0.4mmol of 1, 4-dinaphthyl aldehyde, 1.2mmol of ammonium acetate and 1.2mmol of NaIO into a reactor44.0mL EA. Continuously stirring for 3h at 50 ℃ in the nitrogen atmosphere, stopping reaction, cooling to room temperature, washing with saturated NaCl, extracting with ethyl acetate, distilling under reduced pressure, concentrating to remove the solvent, drying, and separating the crude product by column chromatography to obtain the target product with the yield of 57%.1H NMR(400MHz,CDCl3):δ9.28(s,3H),7.77(s,3H),7.42(s,3H), 1.66(s,27H),1.46(s,27H).13C{1H}NMR(101MHz,CDCl3):δ160.8,148.1, 147.1,142.4,134.0,129.5,128.1,120.3,114.6,35.2,34.6,31.8,30.1。
Claims (5)
1. A method for synthesizing a dibenzoxazole fluorescent whitening agent and derivatives thereof is characterized in that the preparation raw materials of the dibenzoxazole fluorescent whitening agent and the derivatives thereof comprise: catechol compounds, ammonium acetate, aryl-dicarbaldehyde and sodium periodate; comprises the following steps: mixing catechol compound, ammonium acetate, aryl dicarbaldehyde and sodium periodate; adding a solvent in an inert gas atmosphere, heating and stirring for reaction, cooling to room temperature after the reaction is finished, washing with saturated NaCl, extracting, distilling under reduced pressure and concentrating to remove the solvent, drying, and separating a crude product by column chromatography to obtain the dibenzoxazole fluorescent whitening agent and derivatives thereof;
the catechol compound has the following structural formula:
the aryl dicarboxaldehyde has the following structural formula:
the dibenzoxazole fluorescent whitening agent and the derivative thereof have the following structural formula (I):
r is a substituent at any one or more positions on a benzene ring, and each R is independently selected from one of methyl, tert-butyl and methoxy; ar is one of phenyl, naphthyl and thienyl;
the solvent is one of N, N-dimethylformamide, 1, 2-dichloroethane, acetonitrile, chloroform and ethyl acetate;
the reaction temperature is 50-100 ℃; the reaction time is 3-4 h.
2. The method for synthesizing a bis-benzoxazole fluorescent whitening agent and derivatives thereof according to claim 1, wherein the catechol compound is one selected from the group consisting of 3, 5-di-tert-butyl catechol, p-tert-butyl catechol, 4-tert-butyl-5-methyl catechol, and 3-methoxy catechol.
3. The method for synthesizing bis-benzoxazole fluorescent whitening agent and its derivatives according to claim 1, wherein the aryldicarboxaldehyde is one selected from 2, 5-thiophenedicarboxaldehyde, 1, 4-benzenedicarboxaldehyde, 1, 3-benzenedicarboxaldehyde, and 1, 4-naphthalenedicarboxaldehyde.
4. The method for synthesizing bis-benzoxazole fluorescent whitening agent and derivatives thereof according to claim 1, wherein the molar ratio of the catechol compound, ammonium acetate, aryl dicarbaldehyde and sodium periodate is 2.8-3.2: 3.8-4.2: 1: 1.8-2.2.
5. The method for synthesizing bis-benzoxazole fluorescent whitening agents and derivatives thereof according to claim 1, wherein the inert gas is any one or combination of nitrogen, argon and helium.
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| US4017508A (en) * | 1974-07-01 | 1977-04-12 | Eastman Kodak Company | Benzoxazole ultraviolet stabilizers and their use in organic compositions |
| CN101143854A (en) * | 2006-09-15 | 2008-03-19 | 沈阳化工研究院 | Synthesis method for dibenzoxazole compounds |
| CN101516861A (en) * | 2006-10-09 | 2009-08-26 | 科莱恩金融(Bvi)有限公司 | Method for producing bisbenzoxazoles |
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