Synthesis method for biphenyl compound

A synthesis method and compound technology, applied in organic chemistry methods, chemical instruments and methods, and hydrocarbon production from halogen-containing organic compounds, etc., can solve problems such as difficult operation, low yield of target products, increased costs, etc., and achieve low cost , No waste residue pollution, little impact on the environment

Inactive Publication Date: 2007-10-17
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method is not easy to operate under high pressure. Adding zinc powder will produce a large a

Method used

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  • Synthesis method for biphenyl compound

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Embodiment 1

[0027] The synthesis of embodiment 1 biphenyl

[0028] Add NaOH (8 g, 0.2 mol), H 2 O (27mL), ethylene glycol (6.2g, 0.1mol), bromobenzene (15.6g, 0.1mol), after stirring to form an emulsion, add 5% Pd / C catalyst (4.2g, 0.2mol%) at 100 After reacting at ℃ for 5 h, the reaction liquid was cooled and suction filtered. The filter cake was Pd / C catalyst, which was washed with water and could be recycled and reused; the filtrate was extracted with ethyl acetate, and the solvent was evaporated to obtain the crude product, which was recrystallized to obtain white crystal 7.1 g, yield 93%, melting point 70°C. 1 H NMR (400MHz, CDCl 3 ,) δppm: 7.60 (d, 4H, J = 7.5Hz), 7.44 (t, 4H, J = 7.2Hz), 7.35 (t, 2H, J = 7.2Hz); 13 C NMR (CDCl 3 ) δppm: 141.2, 128.7, 127.2, 127.1; MS (EI): m / z (%): 154 (100) [M + ], 153(35), 152(20), 115(3), 76(13), 51(4).

Embodiment 2

[0029] Synthesis of embodiment 2 biphenyl

[0030] In a 100mL round bottom flask, add KOH (11.2g, 0.2mol), H 2 O (27mL), ethanol (4.6g, 0.1mol), bromobenzene (15.6g, 0.1mol), after stirring to form an emulsion, add 5% Pd / C catalyst (4.2g, 0.2mol%) and react at 100°C After 5h, the reaction liquid was cooled and suction-filtered, the filter cake was Pd / C catalyst, which was washed with water, and could be recycled and reused; the filtrate was extracted with ethyl acetate, and the solvent was evaporated to obtain a crude product, which was recrystallized to obtain 7.1 g of white crystals, collected The yield is 90%, and the melting point is 70°C.

Embodiment 3

[0031] Embodiment 3 4, the synthesis of 4-dichlorobiphenyl

[0032] Add NaOH (20 g, 0.5 mol), H 2 O (45mL), ethylene glycol (32g, 0.5mol), p-bromochlorobenzene (12.8g, 0.1mol), after stirring to form an emulsion, add 5% Pd / C catalyst (10.5g, 0.5mol%) in Reaction at 100°C for 5 hours, white crystals precipitated, the reaction liquid was cooled and filtered, and the filter cake Pd / C catalyst was washed with water, which can be recycled and reused; the filtrate was extracted with ethyl acetate, and the solvent was evaporated to obtain the crude product, which was recrystallized to obtain white Crystal 7.1g, yield 89%, melting point 149°C. 1 HNMR (400MHz, CDCl 3 ) δppm: 7.48 (d, 4H, J=8.0Hz), 7.40 (d, 4H, J=8.0Hz); 13C NMR (CDCl 3 )δppm: 138.4, 133.7, 129.0, 128.2; MS (EI): m / z (%): 222 (100) [M + ], 186(15), 152(51), 111(5), 93(7), 75(9).

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Abstract

The invention discloses a synthetic method of biphenyl compounds which is prepared through adding alkalis, alcohol and halogenated aromatic compounds into water, mixing it to form microemulsion system, then adding Pd/C as catalyst, reacting 2 to 10h at 50 to 120 DEG C, postprocessing the resultant of reaction to obtain the biphenyl compounds. The present invention is characterized in that using alcohol as additive agent, using lower price Pd catalyst, having features of lower cost, short reaction time, high yield, no pollution and in favor of industrialization.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of a biphenyl type compound. (2) Background technology [0002] As an important organic raw material, biphenyl is widely used in medicine, pesticides, dyes, liquid crystal materials and other fields. Due to the good thermal stability of biphenyl, it can be used as a heat carrier in the heating fluid. Biphenyl type substances are currently the best synthetic heat transfer oil raw materials, and can also be used as solvents for the production of drugs and the preservation of citrus fruits. Biphenyl also has many important derivative products such as emulsifiers, fluorescent whitening agents, fabric dyes, synthetic resins, pesticides, etc. For example, 4,4-dichloromethylbiphenyl is an important intermediate for the synthesis of high-grade stilbene biphenyl optical brighteners; 4,4-dihydroxybiphenyl can be used as raw materials for liquid crystal polymers, rubber and latex Anti-aging agent, dye int...

Claims

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Application Information

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IPC IPC(8): C07B37/00C07C1/26C07C17/269C07D333/18C07D213/22C07D215/12C07D333/50
CPCY02P30/20Y02P30/40
Inventor 裴文董华孙莉吴香梅陶金海
Owner ZHEJIANG UNIV OF TECH
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