Preparation and application of phenol-D6_Kain Industrial Additive

Background and overview^[1-3]

Phenol-D6 is deuterated phenol, which can be prepared from phenol and heavy water in one step. Phenol-D6 can be used as an internal standard or for the preparation of stable isotope-labeled p-hydroxybenzoic acid.

Preparation^[3]

Yamamoto et al. reported that phenol-D6 can be obtained by reacting phenol with heavy water catalyzed by PtO₂ at 250°C and 4 MPa.

Apply^[1-2]

Application 1,

CN201610916174.1 reports a method for simultaneous determination of phenol and BHT in hot melt adhesive, which includes the following steps:

(1) Sample extraction: Accurately weigh the hot melt adhesive sample, add an extraction solvent containing double internal standards, extract under heating conditions, and cool to room temperature after extraction; the extraction temperature is 50-70°C , the extraction time is 2-30min;

(2) Sample purification: Add a poor solvent to the sample extraction solution, remove the matrix after high-speed centrifugation, and take the supernatant to obtain the sample purification solution;

(3) Determination: Pass the purified liquid obtained in step (2) through a microporous filter membrane, analyze the filtrate using gas chromatography-mass spectrometry, and quantify it with the double internal standard method. Calculate the content of the target substance according to the standard curve, and use heating Extraction under conditions can significantly improve the extraction rate. The purification method of adding poor solvents to remove the matrix is ​​easy to operate and can effectively remove interfering substances. The matrix interference is significantly reduced and instrument pollution is reduced, thereby obtaining lower detection limits and quantification limits; using Double internal standard method, high recovery rate, accurate and reliable quantification.

The concentration of the double internal standards is 0.01-20mg/L. One of the double internal standards added is 2-fluorophenol, 3-fluorophenol, 4-fluorophenol or deuterated phenol-d6, and the other is Deuterated 2,3,6-tricresol-d11 or deuterated o-cresol-d7.

Application 2,

Stable isotope labeled p-hydroxybenzoic acid (p-hydroxybenzoic acid) is a white needle-shaped crystal. It is an important precursor compound in the synthesis process of stable isotope labeling reagents and can be used for the synthesis of preservatives, dyes, fungicides, etc. Internal standard reagents labeled with stable isotopes are widely used. CN201610157322.6 reports a synthesis method of stable isotope C or D labeled p-hydroxybenzoic acid, which includes the following steps:

(1) Add stable isotope labeled phenol and cocatalyst to the reactor, add NaOH aqueous solution and main catalyst in sequence while stirring, continue stirring, add carbon tetrachloride, and heat the reaction;

(2) After the reaction is completed, perform suction filtration, acidification, extraction, concentration, and recrystallization to obtain the target product.

The stable isotope labeled phenol is phenol-C or phenol-D6.

References

[1] [China invention, China invention authorization] CN201610916174.1 A method for simultaneous determination of phenol and BHT in hot melt adhesive

[2] [Chinese invention, Chinese invention authorization] CN201610157322.6 A synthesis method of stable isotope 13C or D labeled p-hydroxybenzoic acid [Public]/A kind of synthesis of stable isotope C or D labeled p-hydroxybenzoic acid Method【Authorization】

[3] Mitsuru, Yamamoto, Koichiro, et al. PLATINUM CATALYZED H-D EXCHANGE REACTION OF VARIOUS AROMATIC COMPOUNDS UNDER HYDROTHERMAL CONDITION[J]. Heterocycles, 2006.