Abstract: The 3- and 4-methylcatechols are converted to the corresponding benzaldehyde by first alkylating the hydroxyl groups to form an alkylated methylcatechol. The methyl group is then converted to a methyl dibromide group using 1,3-dibromo-5,5-dimethylhydantoin in the presence of a non-polar, non-reactive solvent such as carbon tetrachloride and heptane and a radical initiator having a ten hour half-life temperature in the range of 47.degree. to 55.degree. C. The dibromide is then hydrolyzed to form the aldehyde.
Abstract: Natural cresylic acid is processed to remove neutral oil impurities by countercurrent liquid/liquid extraction using a heavy phase solvent of a mixture of glycerol and another polyhydric alcohol, preferably triethylene glycol. The light phase solvent is a light paraffinic or cycloparaffinic hydrocarbon.
Type:
Grant
Filed:
September 15, 1997
Date of Patent:
October 12, 1999
Assignee:
Dakota Gasification Company
Inventors:
David H. Duncan, Gene G. Baker, Dana J. Maas, Kevin M. Mohl, Alfred K. Kuhn
Abstract: Alkoxybenzaldehydes and aryloxybenzaldehydes are converted to the corresponding phenols by reacting the benzaldehydes in an organic solvent phase with formic acid and hydrogen peroxide in an aqueous solvent phase to produce the corresponding formate ester. The formate ester is then saponified to produce the corresponding phenol.
Abstract: A process for the purification of natural cresylic acid feedstocks which are first depitched. The depitched feedstock is extractively distilled with a polyhydric alcohol, preferably triethylene glycol, to remove virtually all neutral oil species which are indigenous to the phenol and cresol boiling ranges, most of the neutral oil species in the 2,4-2,5-xylenol boiling range, and a significant portion of the neutral oil species of the high boiling xylenol fraction (including of 2,3-xylenol, 3,5-xylenol, para-ethylphenol, meta-ethylphenol, 3,4-xylenol, and numerous C.sub.9 phenols). This process is also capable of removing tar bases such as pyridine and its alkyl homologues.
Type:
Grant
Filed:
May 28, 1996
Date of Patent:
May 12, 1998
Assignee:
Dakota Gasification Company
Inventors:
David H. Duncan, Gene G. Baker, Alfred K. Kuhn, Dana J. Maas, Kevin M. Mohl
Abstract: An extractive distillation process using a high boiling polyol such as glycerol is employed for separating high purity catechol, 3-methylcatechol and 4-methylcatechol from a high boiling, pitch-like dihydric phenol fraction. Fractional distillation first separates an impure overhead mixture of the catechol and 3-methylcatechol and an impure 4-methylcatechol bottoms. The impure overhead is extractively distilled to remove impurities and then extractively distilled again to separate the catechol and 3-methylcatechol. This produces a pure overhead of 3-methylcatechol and a bottoms of catechol and polyol which is distilled to recover the catechol and recycle the polyol. The impure 4-methylcatechol is distilled to remove residual material and then extractively distilled to remove impurities. The resulting mixture of 4-methylcatechol and polyol is distilled to recover the pure 4-methylcatechol and to recycle the polyol.
Type:
Grant
Filed:
June 15, 1995
Date of Patent:
October 21, 1997
Assignee:
Dakota Gasification Company
Inventors:
David H. Duncan, Gene G. Baker, Dana J. Maas, Kevin M. Mohl, Alfred K. Kuhn
Abstract: A discrete impure cresylic acid distillate fraction derived by fractional distillation of a natural cresylic acid feedstock from which tar bases and/or neutral oils have not been removed is subjected to extractive distillation with a polyhydric alcohol extractant and subsequent separation of the discrete cresylic acid fraction. The extractive distillation removes tar bases, neutral oils, undesirable phenolic substances, sulfur compounds, color-forming impurities and odor-imparting impurities.
Type:
Grant
Filed:
July 2, 1993
Date of Patent:
October 11, 1994
Assignee:
Dakota Gasification Company
Inventors:
David H. Duncan, Gene G. Baker, Dana J. Maas, Kevin M. Mohl, Robert G. Todd