US 9,809,533 B2
Purification method of aldehyde compound
Naoyuki Kakinuma, Omuta (JP); Masayuki Furuya, Arao (JP); Michiharu Sakata, Kurume (JP); Koichi Tokunaga, Chikugo (JP); and Shigetoshi Kuma, Kurume (JP)
Assigned to MITSUI CHEMICALS, INC., Tokyo (JP)
Appl. No. 14/434,114
Filed by Mitsui Chemicals, Inc., Minato-ku, Tokyo (JP)
PCT Filed Nov. 8, 2013, PCT No. PCT/JP2013/080315
§ 371(c)(1), (2) Date Apr. 8, 2015,
PCT Pub. No. WO2014/073663, PCT Pub. Date May 15, 2014.
Claims priority of application No. 2012-247464 (JP), filed on Nov. 9, 2012.
Prior Publication US 2015/0291513 A1, Oct. 15, 2015
Int. Cl. C07C 263/10 (2006.01); B01J 31/24 (2006.01); C07C 255/47 (2006.01); C07C 265/14 (2006.01); C07C 211/19 (2006.01); C07B 63/00 (2006.01); C07C 209/26 (2006.01); C07C 253/30 (2006.01); C07C 253/34 (2006.01)
CPC C07C 263/10 (2013.01) [B01J 31/24 (2013.01); C07B 63/00 (2013.01); C07C 209/26 (2013.01); C07C 211/19 (2013.01); C07C 253/30 (2013.01); C07C 253/34 (2013.01); C07C 255/47 (2013.01); C07C 265/14 (2013.01); C07C 2602/42 (2017.05)] 6 Claims
 
1. A manufacturing method of an aldehyde compound, comprising:
a step of obtaining a reaction solution containing an aldehyde compound by reacting a compound represented by the following Formula (a1) or (a2) with hydrogen and carbon monoxide in the presence of a metal compound of groups 8 to 10 and a phosphorus compound;
a step of neutralizing the reaction solution by adding water and a base compound to the reaction solution; and
a step of purifying an aldehyde compound by distilling the neutralized reaction solution,
wherein the phosphorus compound is represented by the following Formula (R1O)3P, and the base compound is at least one selected from carbonate and hydrogen carbonate of metals of group I on the periodic table and carbonate and hydrogen carbonate of metals of group II on the periodic table,

OG Complex Work Unit Drawing
in Formula (a1), X represents a hydrogen atom, a cyano group, an aldehyde group, or a —CH═NR group; R represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an aryl group; and in Formulae (a1) and (a2), n represents 0, 1, or 2,
(R1O)3P
in the formula, a plurality of R1s may be the same as or different from each other, and represents an alkyl group having 1 to 16 carbon atoms that may have a substituent or an aryl group having 6 to 16 carbon atoms that may have a substituent, and
wherein the step of neutralizing the reaction solution is performed within a temperature range of equal to or higher than 40° C. and equal to or lower than 50° C.