US 11,952,329 B2
Product 1,3-butylene glycol
Hirotaka Tanaka, Kanagawa (JP); Takashi Hakumura, Mie (JP); and Jun Kanada, Mie (JP)
Assigned to KH NEOCHEM CO., LTD., Tokyo (JP)
Appl. No. 18/556,453
Filed by KH Neochem Co., Ltd., Tokyo (JP)
PCT Filed Jun. 2, 2022, PCT No. PCT/JP2022/022426
§ 371(c)(1), (2) Date Oct. 20, 2023,
PCT Pub. No. WO2022/255436, PCT Pub. Date Dec. 8, 2022.
Claims priority of application No. 2021-094284 (JP), filed on Jun. 4, 2021.
Prior Publication US 2024/0083830 A1, Mar. 14, 2024
Int. Cl. C07C 31/20 (2006.01); C07C 29/74 (2006.01); B01D 15/08 (2006.01); G01N 30/02 (2006.01)
CPC C07C 31/207 (2013.01) [C07C 29/74 (2013.01); C07C 31/20 (2013.01); B01D 15/08 (2013.01); G01N 30/02 (2013.01); G01N 2030/027 (2013.01)] 3 Claims
 
1. A product 1,3-butylene glycol, wherein, in an HPLC analysis under the following conditions after the following sample preparation, when a relative retention time of 2,4-dinitrophenylhydrazine is regarded as 1.0, a sum area value of absorbance peaks that appear within a relative retention time range of 4.4 to 12.0 is 1000 or less, and wherein
a dinitrophenylhydrazine derivative of a carbonyl compound having 4 to 6 carbon atoms is contained as a component that corresponds to the peaks that appear within the relative retention time range of 4.4 to 12.0,
wherein the sample preparation is as follows:
1000 μL of a solution of 2,4-dinitrophenylhydrazine which is extracted by adding 5 mL of acetonitrile to a 2,4-dinitrophenylhydrazine cartridge and 100 μL of 0.2 mol/L hydrochloric acid are added to 0.05 g of the product 1,3-butylene glycol and reacted at 45° C. for two hours, and
wherein the conditions of HPLC analysis are as follows:
measurement sample: a reaction liquid obtained by the sample preparation is diluted to 2 mL with a mobile phase that is used in HPLC, and the diluted liquid is used as a measurement sample,
detector: UV-Vis detector,
detection wavelength: 369 nm,
analysis column: a column in which palmitamidopropyl group-modified silica gel (particle diameter: 5 μm, inner diameter×length=4.6 mm×25 cm, pore size: 100 Å, surface coating level: 2.7 μmol/m2, surface area: 450 m2/g, metal impurity: less than 5 ppm, carbon content: 19.5%) is used as a stationary phase,
analysis condition: column temperature of 40° C.,
mobile phase: acetonitrile/distilled water=50/50 (volume ratio),
mobile phase flow rate: 0.4 mL/min.,
sample injection amount: 20 μL.