CN106432114A - Method for synthesizing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine - Google Patents
Method for synthesizing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine Download PDFInfo
- Publication number
- CN106432114A CN106432114A CN201610876523.1A CN201610876523A CN106432114A CN 106432114 A CN106432114 A CN 106432114A CN 201610876523 A CN201610876523 A CN 201610876523A CN 106432114 A CN106432114 A CN 106432114A
- Authority
- CN
- China
- Prior art keywords
- triazine
- diphenyl
- sym
- reaction
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 0 C[C@](*C=CCC(C)=C)C(NCC/C1=C\C*C/C=C(\C)/C1)=NC(O)=NC Chemical compound C[C@](*C=CCC(C)=C)C(NCC/C1=C\C*C/C=C(\C)/C1)=NC(O)=NC 0.000 description 3
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a method for synthesizing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine. The method comprises the following steps: step 1: 2-chloro-4,6-diphenyl-1,3,5-sym-triazine is prepared from cyanuric chloride and benzene in an organic solvent through an alkylation reaction; step 2: 2-chloro-4,6-diphenyl-1,3,5-sym-triazine obtained through the reaction is subjected to an alkylation reaction directly with resorcinol without separation, and 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine is synthesized. The method for synthesizing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine is simple to operate and low in cost, is cleaner compared with the conventional method and can reduce great consumption of power, labor and raw materials, and the reaction yield is increased by 10% compared with the conventional process.
Description
Technical field
The invention belongs to organic chemical synthesis technical field, be specifically related to a kind of synthesis 2-(2,4-dihydroxy phenyls）-4,
The method of 6-diphenyl-1,3,5-s-triazine.
Background technology
2-(2,4-dihydroxy phenyl）-4,6-diphenyl-1,3,5-s-triazine is of triazine-based ultraviolet absorbent
Important intermediate, such as the 2-(2-hydroxyl-4-Hexyloxy-phenyl being synthesized by it）-4,6-diphenyl-1,3,5-s-triazine（UV-
1577）Being a kind of efficient ultra-violet absorber, it has higher absorption efficiency and relatively low color and luster and higher processing
Stability, has wide application in some polymeric materials.
At present, 2-(2,4-dihydroxy phenyls）The synthetic method of-4,6-diphenyl-1,3,5-s-triazine mainly has several as follows
Kind：
1st, alkylation process
The method is first to react with benzene using alchlor as catalyst, Cyanuric Chloride, and reaction completes after treatment, to separate
To 2-chloro-4,6-diphenyl-1,3,5-s-triazine, then with resorcin reaction, with alchlor as catalyst, generate 2-
(2,4-dihydroxy phenyl）-4,6-diphenyl-1,3,5-s-triazine.The building-up process of the method is as shown below：
The first step：
Second step：
The method production stage is many, the catalyst AlCl of use3Consumption is big, and post-reaction treatment results in substantial amounts of spent acidic
Water.
2nd, Grignard
The method is reacted with grignard reagent reacting with Cyanuric Chloride and is completed after treatment, isolated 2-chloro-4,6-diphenyl-1,
3,5-s-triazine, then with resorcin reaction, with alchlor as catalyst, generate 2-(2,4-dihydroxy phenyls）-4,6-
Diphenyl-1,3,5-s-triazine.The building-up process of the method is as shown below：
The first step：
Second step：
The method has extraordinary selectivity, and shortcoming is that condition requires harshness, needs to ensure the condition of anhydrous and oxygen-free, and molten
In agent removal process, there is the potential safety hazards such as the blast that peroxide causes.
Other are also just like indirect alkylation method, patent US5705643 of patent JP9059263A and EP0497734A1 employing
Becoming around-France etc. with US5478935 uses, generally there is the shortcomings such as synthesis step is longer in these methods.
From the point of view of from the above, more ripe is to pay gram alkylation process and schematized version.
Content of the invention
The technical problem to be solved is to provide for a kind of yield height, operating procedure is few, pollute little 2-(2,4-
Dihydroxy phenyl）The synthetic method of-4,6-diphenyl-1,3,5-s-triazine.
For solving above-mentioned technical problem, the technical solution adopted in the present invention is as follows：
A kind of synthesis 2-(2,4-dihydroxy phenyl）-4,6-diphenyl-1, the method for 3,5-s-triazine, comprise the steps：
1st, Cyanuric Chloride and benzene are in organic solvent, prepare 2-chloro-4,6-diphenyl-1,3,5-s-triazine through alkylated reaction；
2nd, reacting the 2-chloro-4 obtaining, 6-diphenyl-1,3,5-s-triazine without isolation, are directly alkylated with resorcinol
2-(2,4-dihydroxy phenyl is synthesized）-4,6-diphenyl-1,3,5-s-triazine.
In step 1, described organic solvent is the mixed solvent of ethyl acetate and chlorobenzene；Described organic mixed solvent
In, the volume ratio of ethyl acetate and chlorobenzene is 1:1～10, preferably 1:4～6, most preferably 1:5.
In step 2, what reaction obtained contains 2-chloro-4, and 6-diphenyl-1, the reactant liquor of 3,5-s-triazine is not treated, directly
Connect and rise to uniform temperature and add resorcinol to be alkylated 2-(2,4-dihydroxy phenyl is synthesized）-4,6-diphenyl-1,
3,5-s-triazine, after reaction completes, post-treated obtain target product.
Reaction equation is as follows：
Beneficial outcomes：2-(the 2,4-dihydroxy phenyl of the present invention）-4,6-diphenyl-1, the synthetic method of 3,5-s-triazine, work
Skill route is short, low cost, and waste water is few.Two-step reaction in original technique is realized by one kettle way, decreases operating procedure, subtract
Lack catalyst AlCl3Usage amount 1/3, and then decrease the generation of acid waste water.With former conventional alkylation process, more clearly
Clean, and reaction yield more common alkylation process raising 10%.
Detailed description of the invention：
Embodiment 1：
In the 250mL four-hole boiling flask being furnished with mechanical agitation, thermometer, tail gas absorbing system, add chlorobenzene and the 20mL of 100mL
Ethyl acetate, be then sequentially added into 18.4g（0.1mol）Cyanuric Chloride, 40.0g（0.3mol）Alchlor, under stirring, fall
Temperature, to 18-22 DEG C, then drips 15.6g（0.2mol）Benzene, dropping finishes, and after keeping reaction 4h, is warming up to 60-70 DEG C, in batches
Add 11.0g（0.1mol）Resorcinol.Reaction finishes, and inclines reactant liquor such as the tetra-mouthfuls of reaction bulbs of 500mL equipped with 100mL water
In, the lower hydrolysis of stirring, ethyl acetate and chlorobenzene are reclaimed in then intensification azeotropic distillation, after finishing, cooling, filter, be washed to neutrality,
Obtain 2-(2,4-dihydroxy phenyl）-4,6-diphenyl-1, the crude product of 3,5-s-triazine, recrystallize light with toluene and petroleum ether
Yellow solid 22.2g, yield 65.0%.
Embodiment 2：
Identical with embodiment 1 method, except that add 90mL chlorobenzene and 30mL ethyl acetate, finally give 2-(2,4-
Dihydroxy phenyl）-4,6-diphenyl-1,3,5-s-triazine 21.4g, yield 62.7%.
Embodiment 3：
Identical with embodiment 1 method, except that add 80mL chlorobenzene and 40mL ethyl acetate, finally give 2-(2,4-
Dihydroxy phenyl）-4,6-diphenyl-1,3,5-s-triazine 21.0g, yield 61.5%.
Claims (4)
1. a synthesis 2-(2,4-dihydroxy phenyl）-4,6-diphenyl-1, the method for 3,5-s-triazine, it is characterised in that the party
Method comprises the steps：
（1）Cyanuric Chloride and benzene in organic solvent, prepare 2-chloro-4,6-diphenyl-1,3,5-s-triazine through alkylated reaction；
（2）The 2-chloro-4 that reaction obtains, 6-diphenyl-1, without isolation, direct and resorcinol carries out alkyl to 3,5-s-triazine
Change and 2-(2,4-dihydroxy phenyl is synthesized）-4,6-diphenyl-1,3,5-s-triazine.
2. synthesis 2-(2,4-dihydroxy phenyl according to claim 1）The side of-4,6-diphenyl-1,3,5-s-triazine
Method, it is characterised in that step（1）In, described organic solvent is mixed solvent：Ethyl acetate and chlorobenzene.
3. synthesis 2-(2,4-dihydroxy phenyl according to claim 1）The side of-4,6-diphenyl-1,3,5-s-triazine
Method, it is characterised in that step（1）In, the volume ratio of described organic mixed solvent ethyl acetate and chlorobenzene is 1:1～10.
4. synthesis 2-(2,4-dihydroxy phenyl according to claim 1）The side of-4,6-diphenyl-1,3,5-s-triazine
Method, it is characterised in that step（2）In, reaction obtain contain 2-chloro-4,6-diphenyl-1, the reactant liquor of 3,5-s-triazine without
Process, directly rise to uniform temperature and add resorcinol to be alkylated 2-(2,4-dihydroxy phenyls are synthesized）-4,6-two
Phenyl-1,3,5-s-triazine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610876523.1A CN106432114A (en) | 2016-10-09 | 2016-10-09 | Method for synthesizing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610876523.1A CN106432114A (en) | 2016-10-09 | 2016-10-09 | Method for synthesizing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106432114A true CN106432114A (en) | 2017-02-22 |
Family
ID=58173231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610876523.1A Pending CN106432114A (en) | 2016-10-09 | 2016-10-09 | Method for synthesizing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106432114A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108727288A (en) * | 2018-07-04 | 2018-11-02 | 中昊(大连)化工研究设计院有限公司 | Alkylation process synthesizes the new process of the chloro- 4,6- diphenyl -1,3,5- s-triazine of 2- |
| CN109180597A (en) * | 2018-09-03 | 2019-01-11 | 中昊(大连)化工研究设计院有限公司 | A kind of preparation method of 2- (2,4- dihydroxy phenyl) -4,6- diphenyl -1,3,5- triazine |
| CN116143715A (en) * | 2023-02-28 | 2023-05-23 | 江苏极易新材料有限公司 | Synthesis method of 2- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -5-n-hexyloxyphenol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130120211A (en) * | 2012-04-25 | 2013-11-04 | 박치상 | Manufacturing method of pet resin that contains uv stabilizer |
| WO2016053662A1 (en) * | 2014-09-30 | 2016-04-07 | Transitions Optical, Inc. | Ultraviolet light absorbers |
-
2016
- 2016-10-09 CN CN201610876523.1A patent/CN106432114A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130120211A (en) * | 2012-04-25 | 2013-11-04 | 박치상 | Manufacturing method of pet resin that contains uv stabilizer |
| WO2016053662A1 (en) * | 2014-09-30 | 2016-04-07 | Transitions Optical, Inc. | Ultraviolet light absorbers |
Non-Patent Citations (2)
| Title |
|---|
| ZHONG H.L.ET AL.: "New Optoelectronic Materials Based on Bitriazines: Synthesis and Properties", 《ORGANIC LETTERS》 * |
| 安方: "紫外线吸收剂2,4- 二( 3′, 5′- 二甲苯基) - 6-( 2′- 羟基- 4′- 辛氧基) 苯基- 1,3,5 三嗪的合成", 《塑料助剂》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108727288A (en) * | 2018-07-04 | 2018-11-02 | 中昊(大连)化工研究设计院有限公司 | Alkylation process synthesizes the new process of the chloro- 4,6- diphenyl -1,3,5- s-triazine of 2- |
| CN109180597A (en) * | 2018-09-03 | 2019-01-11 | 中昊(大连)化工研究设计院有限公司 | A kind of preparation method of 2- (2,4- dihydroxy phenyl) -4,6- diphenyl -1,3,5- triazine |
| CN116143715A (en) * | 2023-02-28 | 2023-05-23 | 江苏极易新材料有限公司 | Synthesis method of 2- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -5-n-hexyloxyphenol |
| CN116143715B (en) * | 2023-02-28 | 2023-11-24 | 江苏极易新材料有限公司 | Synthesis method of 2- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) -5-n-hexyloxyphenol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2697192A1 (en) | Method for preparation of ketoxime compound and method for preparation of alkoxy-amine hydrochloride | |
| CN106432114A (en) | Method for synthesizing 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-1,3,5-sym-triazine | |
| CN110372620A (en) | A kind of preparation method of ultraviolet absorbing agent UV-1600 intermediate | |
| JP2023029877A (en) | Methods for preparation of 1,3-benzodioxole heterocyclic compounds | |
| CN103130657A (en) | Synthetic method of 2-chloro-4-aminophenol | |
| CN103254147B (en) | A kind of preparation method of D-Su-Type-2--(dichloromethyl)-4,5-dihydro-5-[p-(methylsulfonyl) phenyl]-4-oxazole methyl alcohol | |
| CN104529935B (en) | Method for synthesizing ethyl 2-(3-aldehyde-4-isobutyloxyphenyl)-4-methylthiazole-5-formate | |
| Davod et al. | One-pot synthesis of 14-aryl-14 h-dibenzo [a, j] xanthene derivatives catalyzed by nano-alumina sulfuric acid through solvent-free conditions | |
| CN102199073A (en) | Method for preparing 4,4'-dihydroxydiphenylmethane | |
| CN102040572B (en) | Production method of benzofuranone | |
| CN109503343B (en) | Preparation method of photoinitiator 184 | |
| CN101747284A (en) | Method for preparing antioxidant | |
| CN103588765A (en) | Synthesis method for azilsartan medoxomil or salt thereof, intermediate of azilsartan medoxomil or salt thereof and synthesis method for intermediate | |
| CN103588729A (en) | Synthetic method of 1-(biphenyl-4-yl)-2-methyl-2-morpholinopropan-1-one | |
| CN111099975A (en) | Preparation method of 5-bromo-2-chloro-4' -ethoxy benzophenone | |
| KR20180016425A (en) | Improved Process for Making Diaryl Sulfones | |
| CN102675148B (en) | Preparation method of hydroxybenzyl cyanide | |
| CN108203385B (en) | Method for preparing 3- (4-fluoro-2-nitrophenyl) acetone | |
| CN102603547A (en) | New synthesis process of 1-amino-2-acetylanthraquinone and derivatives thereof | |
| CN112624921A (en) | Synthesis method and application of 1-hydroxymethyl cyclopropyl acetic acid | |
| CN101845055B (en) | Method for purifying dichloromethyl phenylsilane by chemical coordination effect | |
| CN104262085A (en) | New synthetic method of 4-halogenated phenylacetylene | |
| CN102010364B (en) | Preparation method for terpene maleimide | |
| CN111285757B (en) | Method for cyclizing pseudo ionone | |
| CN111303172A (en) | Method for preparing etodolac methyl ester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170222 |