Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1983-03-17
1984-10-02
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568780, 568799, 564396, 564442, C07C 3700, C07C 3906
Patent
active
044750013
ABSTRACT:
Ortho- or para-monoalkylated phenols or 2,4- or 2,6-dialkylphenols can be produced from phenolic compounds in good yields and in the absence of isomers. The starting phenol which has at least two available ortho or para positions unsubstituted is converted to a t-alkylated phenol having at least one ortho or para position unsubstituted. The desired t-alkylated phenolic compound is reacted with an aldehyde having one to four carbon atoms and a secondary aliphatic or alicyclic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the secondary amine. The reaction is conducted at a temperature in the range of about 0.degree. C., to about 100.degree. C. and the reaction produces an aminoalkylated t-alkylated phenol. The aminoalkylated phenol is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C. at a hydrogen pressure not greater than 500 psi to produce monoalkylated, mono- or di-t-alkylated phenol or a dialkylated, mono-t-alkylated phenol in the ortho- and para- positions. The thus produced alkylated t-alkylated phenolic compound is contacted with an acid or an acid reacting substance to give the desired alkylated phenolic compound. These compounds are separated to produce ortho-monoalkylated, para-monoalkylphenol, 2,4-dialkylphenol and 2,6-dialkylphenol.
REFERENCES:
patent: 2194215 (1940-03-01), Brunson
patent: 2452154 (1948-10-01), Ross
patent: 2494993 (1950-06-01), Foster
patent: 2842595 (1958-07-01), Rigternik
patent: 3413347 (1968-11-01), Worrel
patent: 3592951 (1971-07-01), Zaweski
patent: 3726882 (1973-04-01), Traise et al.
patent: 3946086 (1976-03-01), Gershanov et al.
patent: 4072724 (1978-02-01), Parker
patent: 4122287 (1978-10-01), Zekharava et al.
patent: 4215229 (1980-07-01), Greco
patent: 4308407 (1981-12-01), Melysner et al.
Brunson et al., "J. Amer. Chem. Soc." vol. 63 pp. 270-272 (1941).
Carlin et al., "J. Amer. Chem. Soc." vol. 72 pp. 2762-2763 (1950).
Caldwell et al., "J. Amer. Chem. Soc." vol. 61 pp. 2354-2357.
Koppers Company Inc.
Lone Werren B.
Long Daniel J.
Zeh, Jr. Herbert J.
LandOfFree
Process for alkylating phenolic compounds to produce ortho- or p does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for alkylating phenolic compounds to produce ortho- or p, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for alkylating phenolic compounds to produce ortho- or p will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-527640