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Preparation method of carbon isotope-labeled bisphenols and bisphenols AF

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

Active Publication Date: 2020-08-04
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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  • Preparation method of carbon isotope-labeled bisphenols and bisphenols AF
  • Preparation method of carbon isotope-labeled bisphenols and bisphenols AF
  • Preparation method of carbon isotope-labeled bisphenols and bisphenols AF

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[0030] The present invention provides a preparation method of carbon isotope-labeled bisphenol S, and the carbon isotope-labeled bisphenol S comprises: 13 C-labeled bisphenol S or 14 C-labeled bisphenol S, including the following steps:

[0031] The carbon isotope-labeled phenol is mixed with sulfuric acid, and the sulfonation reaction and the condensation to sulfone reaction are carried out successively in a protective atmosphere, and then the obtained condensation-to-sulfone product system is separated and purified by normal phase preparative liquid chromatography or normal phase preparative thin-layer chromatography. Obtain carbon isotope-labeled bisphenol S; the carbon isotope-labeled phenol includes 13 C-labeled phenol or 14 C-labeled phenol.

[0032] In the preparation method of carbon isotope-labeled bisphenol S provided by the present invention, when the 13 When C-labeled phenol is a raw material, the prepared product is 13 C-labeled bisphenol S; 14 When C-labele...

Embodiment 1

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

[0065] Synthesis of unlabeled bisphenol S:

[0066] Weigh 100 mg of phenol into a 10 mL eggplant-shaped flask, drop 30 μL of 98wt% concentrated sulfuric acid into it, react at 125 °C for 2.5 h under nitrogen protection, and then heat up to 175 °C for 3 h; after the reaction, add 1 mL of methanol Dissolving the reaction product, the obtained mixture was concentrated under reduced pressure and separated and purified by normal phase preparative liquid chromatography. The elution reagents were petroleum ether and ethyl acetate, and the flow rate was 5 mL / min. Gradient elution was performed by volume ratio. The initial composition of the de-reagent is petroleum ether: ethyl acetate = 4: 1; when the elution is 25 min, the composition of the elutio...

Embodiment 2

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

[0076] Add 3.1 x 10 to the eggplant bottle7 Bq 14 C-phenol (11mg; 2.4×10 8 Bq / mmol, dissolved in 200 μL of petroleum ether), and then added dropwise 3.3 μL of 98wt% concentrated sulfuric acid, under nitrogen protection, reacted at 125 °C for 2.5 h, and then heated to 175 °C for 3 h; after the reaction, 1 mL of methanol was added to dissolve the reaction product, and the resulting mixture was concentrated under reduced pressure and separated and purified by normal-phase preparative thin-layer chromatography. The volume ratio to ethyl acetate is 1:1), the silica gel powder obtained by separation is extracted 5 times with ethyl acetate, the extract is concentrated under reduced pressure to remove ethyl acetate, and then analyzed by liquid chromatography-radioactive detector combined system ( The analytical conditions are shown in Appendix 2), the radioactive purity of the product is 98%, the yield is about 10.0%, and...

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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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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/00C07C315/06C07C317/22
CPCC07B59/001C07B2200/05C07C37/62C07C37/82C07C303/06C07C315/00C07C315/06C07C317/22C07C309/42C07C39/367
Inventor 季荣曹思琪王联红马旖旎
Owner NANJING UNIV
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