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Method for preparing carbon isotope markers bisphenol S and bisphenol AF

A carbon isotope and double-labeled technology, which is applied in the field of synthesis of carbon isotope-labeled compounds, can solve the problems of low yield of bisphenol AF, achieve the effect of simple preparation process, simple synthesis steps, and avoid complicated purification steps

Active Publication Date: 2019-09-17
NANJING UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, according to the composition in this document, that is, by molar ratio of phenol: hexafluoroacetone trihydrate: methanesulfonic acid = 3.5: 1: 3, the reaction process is monitored by high performance liquid chromatography; when the phenol is 1 g, the conversion rate is high , the yield of bisphenol AF is also relatively high; but when the phenol is 10-100 mg, most of the phenol does not react, and the yield of bisphenol AF is very low

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  • Method for preparing carbon isotope markers bisphenol S and bisphenol AF
  • Method for preparing carbon isotope markers bisphenol S and bisphenol AF
  • Method for preparing carbon isotope markers bisphenol S and bisphenol AF

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[0030] The invention provides a method for preparing carbon isotope-labeled bisphenol S, the carbon isotope-labeled bisphenol S includes 13 C labeled bisphenol S or 14 C labeling bisphenol S, including the following steps:

[0031] Mix carbon isotope-labeled phenol with sulfuric acid, carry out sulfonation reaction and condensation sulfone reaction in sequence in a protective atmosphere, and then use normal phase preparative liquid chromatography or normal phase preparative thin layer chromatography to separate and purify the obtained condensation sulfone product system, Obtain carbon isotope label bisphenol S; Described carbon isotope label phenol comprises 13 C labeled phenol or 14 C labeled phenol.

[0032] In the preparation method of carbon isotope labeling bisphenol S provided by the invention, when using 13 When C-labeled phenol is used as raw material, the prepared product is 13 C labeled bisphenol S; when 14 When C-labeled phenol is used as raw material, the pre...

Embodiment 1

[0064] First, non-labeled bisphenol S was prepared to determine the reaction conditions, and the structure of the synthesized non-labeled bisphenol S was characterized by electrospray mass spectrometry and nuclear magnetic resonance to confirm the structure.

[0065] Synthesis of unlabeled bisphenol S:

[0066] Weigh 100mg of phenol into a 10mL eggplant-shaped bottle, add 30μL of 98wt% concentrated sulfuric acid dropwise, under nitrogen protection, react at 125°C for 2.5h, then raise the temperature to 175°C for 3h; after the reaction, add 1mL of methanol The reaction product was dissolved, and the resulting mixed solution was concentrated under reduced pressure and then separated and purified by normal phase preparative liquid chromatography. The elution reagent was petroleum ether and ethyl acetate, and the flow rate was 5mL / min. Gradient elution, in terms of volume ratio, washing The initial composition of the elution reagent is petroleum ether: ethyl acetate = 4: 1; when t...

Embodiment 2

[0075] synthesis 14 C-bisphenol S ([U-ring- 14 C12]-BPS):

[0076] Add 3.1×107 Q 14 C-phenol (11mg; 2.4×10 8 Bq / mmol, dissolved in 200 μL of petroleum ether), and then dropwise added 3.3 μL of 98wt% concentrated sulfuric acid, under nitrogen protection, reacted at 125 ° C for 2.5 h, then raised the temperature to 175 ° C for 3 h; after the reaction, Add 1mL of methanol to dissolve the reaction product, concentrate the resulting mixture under reduced pressure, and then use normal phase preparative thin-layer chromatography to separate and purify. The size of the silica gel preparation plate is 20cm×20cm×2mm, and the developing solvent is petroleum ether and ethyl acetate (petroleum ether The volume ratio to ethyl acetate is 1:1), the separated silica gel powder is extracted 5 times with ethyl acetate, and the extract is concentrated under reduced pressure to remove ethyl acetate, then analyzed by liquid chromatography-radioactive detector coupling system ( Analytical condit...

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Abstract

The invention relates to the technical field of synthesis of carbon isotope marker compounds and in particular to a method for preparing carbon isotope markers bisphenol S and bisphenol AF. The method provided by the invention is easy in reaction raw material obtaining, low in toxicity and simple in preparation process, and because of an expensive raw material marker phenol, a condition that an excessive amount of phenol is required in a conventional synthesis method is broken through in trace synthesis. Meanwhile, the method provided by the invention is simple in synthesis step, the synthesis method has universality, the carbon isotope markers bisphenol S and bisphenol AF can be efficiently and easily synthesized in a trace amount manner, the radioactivity purity of a target compound is up to 98%, and conditions are provided for operation that fates of degradation, conversion and the like of bisphenol S and bisphenol AF in the environment are researched by using a 13C and 14C isotopic tracer technique later.

Description

technical field [0001] The invention relates to the technical field of synthesis of carbon isotope-labeled compounds, in particular to a preparation method of carbon isotope-labeled bisphenol S and bisphenol AF. Background technique [0002] In the resin and plastics industry, bisphenols are commonly used in the production of paints, food cans and inner coatings for thermal paper. Bisphenol S (4,4'-dihydroxydiphenyl sulfone, Bisphenol S, BPS) and bisphenol AF (2,2'-bis(4-hydroxyphenyl)-hexafluoropropane, Bisphenol AF, BPAF) belong to Endocrine disruptor, will be spilled in small amounts during normal use. Bisphenol S was frequently detected in river water with a concentration as high as 3 μg / L. The concentration of bisphenol AF in the sediment of an industrial area in South Korea was as high as 1970ng / g (dry weight) (Liao, C., Liu, F., Moon, H.B., Yamashita, N., Yun, S., and Kannan, K .(2012). "Bisphenol analogues in sediments from industrialized areas in the United State...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C315/06C07C317/22
CPCC07C315/00C07C315/06C07C303/06C07C37/62C07C37/82C07B59/001C07B2200/05C07C317/22C07C309/42C07C39/367
Inventor 季荣曹思琪王联红马旖旎
Owner NANJING UNIV
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