US 11,885,819 B2
Analysis method of diene compound
Masaki Takiwaki, Tokyo (JP); Seketsu Fukuzawa, Tokyo (JP); Misao Matsushige, Yamaguchi (JP); and Shin Watanabe, Yamaguchi (JP)
Assigned to JOEL LTD, Tokyo (JP); and TOKUYAMA CORPORATION, Yamaguchi (JP)
Filed by JEOL Ltd., Tokyo (JP); and TOKUYAMA CORPORATION, Yamaguchi (JP)
Filed on Oct. 7, 2020, as Appl. No. 17/065,221.
Claims priority of application No. 2019-186259 (JP), filed on Oct. 9, 2019.
Prior Publication US 2021/0109119 A1, Apr. 15, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. G01N 33/82 (2006.01); G01N 30/06 (2006.01); C07D 487/08 (2006.01)
CPC G01N 33/82 (2013.01) [C07D 487/08 (2013.01); G01N 30/06 (2013.01); G01N 2030/067 (2013.01); G01N 2560/00 (2013.01)] 14 Claims
 
1. A method for quantifying a diene compound, comprising:
a triazolinedione adduct heating step of heating a triazolinedione adduct represented by formula (1) to produce a triazolinedione compound represented by formula (2);
an ene compound formation step of reacting the triazolinedione compound with a diene compound represented by formula (3) to obtain an ene compound represented by formula (4); and
an ene compound quantifying step of quantifying the ene compound to quantify the diene compound,

OG Complex Work Unit Chemistry
wherein in the formula (1), R1 represents an organic group; and A represents a fused ring having three or more rings comprising at least one aromatic ring,

OG Complex Work Unit Chemistry
wherein in the formula (2), R1 is as defined in the formula (1),

OG Complex Work Unit Chemistry
wherein in the formula (3), R2, R3, R4, R5, R6, and R7 each independently represent a group selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 100 carbon atoms, an aralkyl group, a phenyl group, and a heterocyclic group, wherein the alkyl group, the aralkyl group, the phenyl group, and the heterocyclic group optionally comprise an atom selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom, and a phosphorus atom, and wherein two or more of R2, R3, R4, R5, R6, and R7 are optionally combined with one another, and

OG Complex Work Unit Chemistry
wherein in the formula (4), R1 is as defined in the formula (1); and R2, R3, R4, R5, R6, and R7 are as defined in the formula (3).