- Patent Number:
11952,345
- Appl. No:
17/892212
- Application Filed:
August 22, 2022
- نبذة مختصرة :
Provided is a method for synthesizing bipyridine that includes performing a dimerization reaction of a reactant including a piperidine-based compound, a pyridine-based compound, or a mixture thereof in the presence of a catalyst in which an active metal is supported on a composite metal oxide support including silica (SiO2) and alumina (Al2O3).
- Inventors:
HYUNDAI MOTOR COMPANY (Seoul, KR); KIA CORPORATION (Seoul, KR); KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY (Daejeon, KR)
- Assignees:
HYUNDAI MOTOR COMPANY (Seoul, KR), KIA CORPORATION (Seoul, KR), KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY (Daejeon, KR)
- Claim:
1. A method for synthesizing bipyridine, comprising: performing a dimerization reaction of a reactant consisting of a piperidine-based compound, a pyridine-based compound, or a mixture thereof, in presence of a catalyst in which an active metal is supported on a composite metal oxide support consisting of silica (SiO 2) and alumina (Al 2 O 3).
- Claim:
2. The method of claim 1 , wherein the piperidine-based compound is subjected to a dehydrogenation reaction to prepare the pyridine-based compound in the presence of a catalyst, and the pyridine-based compound is subjected to a dimerization reaction in the presence of a catalyst.
- Claim:
3. The method of claim 2 , wherein the dehydrogenation reaction and the dimerization reaction proceed as a one-pot reaction.
- Claim:
4. The method of claim 1 , wherein the piperidine-based compound consists of piperidine, 2-methylpiperidine, 3-methylpiperidine, 4-methylpiperidine, 3,4-dimethylpiperidine, 2,4-dimethylpiperidine, 2,5-dimethylpiperidine, 2,6-dimethylpiperidine, 3,5-dimethylpiperidine, or a mixture thereof.
- Claim:
5. The method of claim 1 , wherein the pyridine-based compound consists of pyridine, 2-picoline, 3-picoline, 4-picoline, or a mixture thereof.
- Claim:
6. The method of claim 1 , wherein the composite metal oxide support consists of silica in an amount of about 1 wt % to about 50 wt % based on a total weight of the composite metal oxide support.
- Claim:
7. The method of claim 1 , wherein the active metal consists of Pd, Pt, Ru, Sn, Mn, Zn, Mg, V, Ce, La, Y, Sm, Gd, Na, K, Cs, Rb, Ni, Rh, Ir, Co, Fe, Cr, Cu, or a mixture thereof.
- Claim:
8. The method of claim 1 , wherein the catalyst consists of an active metal in an amount of about 0.1 wt % to about 10 wt % based on a total weight of the catalyst.
- Claim:
9. The method of claim 1 , wherein the catalyst consists of an auxiliary metal other than the active metal in an amount of about 1 wt % to about 20 wt % based on a total weight of the catalyst.
- Claim:
10. The method of claim 1 , wherein the catalyst is present in an amount of about 0.3 mole to about 1.0 mole of the active metal of the catalyst based on 100 moles of the reactant.
- Claim:
11. The method of claim 2 , wherein the dehydrogenation reaction, the dimerization reaction, or both proceed at about 150° C. to about 250° C.
- Claim:
12. The method of claim 2 , wherein the dehydrogenation reaction, the dimerization reaction, or both proceed at about 1 bar g to about 5 bar g .
- Claim:
13. The method of claim 1 , further comprising: mixing an acid with the reactant, and then performing the dimerization reaction.
- Claim:
14. The method of claim 13 , wherein the acid consists of sulfuric acid, nitric acid, phosphoric acid, hydrochloric acid, boric acid, heteropolyacid, acetic acid, formic acid, malic acid, citric acid, tartaric acid, ascorbic acid, lactic acid, oxalic acid, succinic acid, tauric acid, or a mixture thereof.
- Claim:
15. The method of claim 13 , wherein the acid is mixed in an amount of about 0.001 mole to about 0.05 mole based on 100 moles of the reactant.
- Patent References Cited:
- Other References:
Abboud, J Org Chem, 2010, 75, 3224-3231. (Year: 2010). cited by examiner
Wang, Chem Asian J, 2016, 11, 2103-2106. (Year: 2016). cited by examiner
Fr. Hein, et al. “A new method for the synthesis of a,a′-dipyridyl.” Ber. Dtsch. Chem. Ges. A/B 61 (1928), 1790, pp. 3. cited by applicant
Robo, Michael T., et al. “4,4′,4″-Trimethyl-2,2′:6′,2″-Terpyridine by Oxidative Coupling of 4-Picoline.” The Journal of Organic Chemistry, vol. 79, No. 21, 2014, pp. 10624-28. Crossref, https://doi.org/10.1021/jo501925s. cited by applicant
- Primary Examiner:
Seaman, D Margaret M
- Attorney, Agent or Firm:
Lempia Summerfield Katz LLC
- الرقم المعرف:
edspgr.11952345
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