Synthesis method of photoinitiator FMT intermediate

A synthesis method and photoinitiator technology, applied in chemical recycling, organic chemistry, etc., can solve the problems of high price, insufficient yield, complicated production process, etc., and achieve the effects of cost saving, simple operation and low cost

Active Publication Date: 2020-05-29
江苏笃行致远新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Literature (Cancer Biology & Therapy, 2009,8 (5), 458-465) and literature (Chemical Reagent, 2014, 36 (3), 265-267) have all reported the method that uses acetic acid as solvent and catalyst, and the former exists production process relatively Complicated, the yield is not high enough (75-80%), and because acetic acid cannot be recovered, the discharge of waste water and waste acid is relatively large; although the latter has a yield of 95%, it needs to go through the column for purification, which is necessary for industrial production very unfavorable
Zhang’s research group of Hebei Normal University (Applied Catalysis, A: General, 2013, 457, 34-41) reported the use of magnetic nanospheres as catalysts and antimony metal ions as Lewis acids. This method has complex catalyst synthesis and high prices. Disadvantages: Patent CN102584904 reports that under anhydrous and oxygen-free conditions, xylene is used as a solvent, and 2,4-difluoroaniline is slowly added dropwise at low temperature, and then the temperature rises to react to prepare 2,4-difluorophenylpyrrole. This method needs to be carried out under harsh conditions of anhydrous and oxygen-free, and also requires long-term dropwise addition at low temperature. These operations are not preferred in large-scale production
[0012] CN200910223949.7 Production method of photoinitiator FMT This patent mentions that 2,4-difluorophenyl is generated by reacting 2,5-dimethoxytetrahydrofuran with 2,4-difluoroaniline in a low-temperature reactor Pyrrole, the patent is to directly obtain the final product of FMT, without separation of intermediates, the quality of the product cannot be guaranteed. In addition, the synthesis method is unscientific in mechanism, and the reaction does not occur without a catalyst, and before and after the patent Different solvents exist in the two-step reaction

Method used

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  • Synthesis method of photoinitiator FMT intermediate
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  • Synthesis method of photoinitiator FMT intermediate

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preparation example Construction

[0029] The invention relates to a synthesis method of a photoinitiator FMT intermediate. 2,4-difluorophenylpyrrole is an important intermediate for preparing the photoinitiator FMT, and a suitable preparation method is indispensable. The invention provides a route of cheap and easy-to-obtain raw materials, recyclable catalyst and solvent, simple and convenient operation, high yield, environmental protection and easy industrialization.

[0030] The synthesis route of this scheme is as follows:

[0031]

[0032] 2,4-Difluoroaniline and furan are in a polar solvent, under the catalysis of sulfonated polystyrene microspheres, the sealed heat preservation reaction is prepared 2,4-difluorophenylpyrrole, wherein 2,4 in the raw material - Both difluoroaniline and furan are conventional commercially available raw materials, and the preparation of sulfonated polystyrene microspheres can refer to the existing sulfonation method of polystyrene microspheres. For example, the following ...

Embodiment 1

[0040] Toluene (10L), 2,4-difluoroaniline (1.3kg) and furan (816g) were successively added to a stirred 20L reaction flask, catalyst sulfonated polystyrene microspheres (130g) were added, heated to 80°C, Seal and keep warm for 12 hours to complete the reaction, cool to room temperature, filter and recover the catalyst sulfonated polystyrene microspheres, directly concentrate under reduced pressure and steam out toluene and furan (for recycling), the crude product is beaten and washed with petroleum ether, filtered, and dried to obtain white Solid 2,4-difluorophenylpyrrole 1.65kg, yield 92.2%, HPLC: 99.2%.

[0041] LCMS(ESI): 180[M+H + ]

[0042] 1 H NMR (400MHz, CDCl 3 )δ7.36(td, J1=8.8, J2=5.8Hz, 1H), 7.01–6.91(m, 4H), 6.35(t, J=2.2Hz, 2H).

Embodiment 2

[0044] Add N,N-dimethylformamide (1L), 2,4-difluoroaniline (130g) and furan (206g) to a stirred 2L reaction flask in turn, add catalyst sulfonated polystyrene microspheres (13g ), heated to 60°C, sealed and kept warm for 15 hours, the reaction was complete, the catalyst sulfonated polystyrene microspheres were recovered by filtration, concentrated under reduced pressure and steamed out N,N-dimethylformamide and furan (recycled), crude oil was used Washed by beating with ether, filtered and air-dried to obtain 170 g of white solid 2,4-difluorophenylpyrrole with a yield of 95.0%.

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Abstract

The invention relates to a synthesis method of a photoinitiator FMT intermediate. The method comprises the following steps: by taking 2, 4-difluoroaniline and furan as raw materials and sulfonated polystyrene microspheres as a catalyst, carrying out sealed heat preservation reaction in a polar solvent, filtering and recovering the catalyst sulfonated polystyrene microspheres, carrying out reducedpressure distillation to recover the solvent and excessive furan to obtain a crude product, crystallizing the crude product by using a non-polar solvent, performing filtering and drying to obtain the2, 4-difluorophenyl pyrrole. The method is simple to operate, the yield can reach more than 90%, the catalyst, the solvent and excessive furan can be recycled, the method is green and environment-friendly, the used materials are industrial products, and are cheaper and easier to obtain, and the quality is easy to control; and the route is a route which is extremely easy to industrialize.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a synthesis method of a photoinitiator FMT intermediate. Background technique [0002] Photoinitiator FMT, the molecular formula is: C 30 h 22 f 4 N 2 Ti, (Cas number: 125051-32-3, molecular weight: 534) chemical name: bis 2,6-difluoro-3-pyrrolephenyl titanocene. The structural formula is as follows: [0003] [0004] Photoinitiator FMT is a high-end photoinitiator sensitive to ultraviolet (UV) and visible light with a titanocene structure. The absorption peaks are 333nm, 396nm, 470nm, and the absorption wavelength can reach 560nm. Its absorption matches the emission wavelength of argon ion laser at 488nm, and it is a good photoinitiator for UV and visible light. The photoinitiator FMT has a deep-layer transmission effect and is suitable for thick coatings and dark-color curing systems. It can cure coatings with a thickness of more than 70 μm and blac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/325
CPCC07D207/325Y02P20/584
Inventor 韩贵芳刘智慧崔志鹏郭敬维刘文娟李欣
Owner 江苏笃行致远新材料科技有限公司
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