Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-05-06
1999-12-07
Ramsuer, Robert W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D40914
Patent
active
05998631&
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel cyclic phenol sulfide having at least one sulfinyl or sulfonyl group which can be used as, e.g., a metal-trapping agent, an ion sensor, a sensor with substrate specificity, a separating-membrane material, a polymer material, an oxidizing catalyst, a phase-transfer catalyst, a synthetic enzyme, a light energy converter, or an intermediate for functional molecules using a recognition ability of an ion or molecule, and a process for producing the same.
BACKGROUND ART
Alkylphenol sulfides are conventionally known as an antioxidant (e.g., U.S. Pat. Nos. 2,239,534, 3,377,334), a rubber sulfurizer (e.g., U.S. Pat. Nos. 3,468,961, 3,647,885), a polymer stabilizer (e.g., U.S. Pat. Nos. 3,882,082, 3,845,013, 3,843,600), an anticorrosive (e.g., U.S. Pat. No. 3,684,587), and a starting material for phenates for use as a lubricating-oil additive (Hori et al., Sekiyu Gakkai-shi, Vol. 34, p. 446, 1991).
Known processes for producing conventional phenol sulfides include a method in which a phenol and elemental sulfur are used as starting materials (e.g., A. J. Neale et al., Tetrahedron, Vol. 25, p. 4593, 1969); a method in which a phenol, elemental sulfur, and a base catalyst are used as starting materials (e.g., U.S. Pat. No. 3,468,961); a method in which a phenol, elemental sulfur, and a molecular halogen are used as starting materials (e.g., B. Hortling et al., Polym. Bull., Vol. 8 (1982), p.1); a method in which a phenol reacts with an aryl disulfide in the presence of a base catalyst (e.g., T. Fujisawa et al., J. Org. Chem., Vol. 33 (1973), p.687); a method in which a phenol and a sulfur halide are used as starting materials (e.g., U.S. Pat. No. 2,239,534); and a method in which a halogenated phenol reacts with a sulfurized alkali metal reagent.
However, they disclose an oligomer containing 2,2'-thiobis(4-alkylphenol) (dimer), 2-[3-(2-hydroxy-5-alkylphenylthio)-2-hydroxy-5-alkylphenylthio]-4-alkylphe nol (trimer), or 2-[3-[3-(2-hydroxy-5-alkylphenylthio)-2-hydroxy-5-alkylphenylthio]-2-hydro xy-5-alkylphenylthio]-4-alkylphenol (tetramer), or a composition containing such an oligomer, and a process for the production thereof. Namely, the alkylphenol sulfides dealt with in those references are all non-cyclic compounds, and the existence of a cyclic phenol sulfide and a method for producing the same have not been disclosed.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a novel cyclic phenol sulfide having at least one sulfinyl or sulfonyl group and a process for producing the same.
The present inventors made intensive studies in order to accomplish the above object. As a result, they have found the existence of a novel cyclic phenol sulfide having at least one sulfinyl or sulfonyl group and that it is obtained from a cyclic phenol sulfide represented by formula (2): ##STR2## wherein X represents a hydrogen atom, a hydrocarbon group, or an acyl group; Y represents a hydrogen atom, a hydrocarbon group, a halogenated hydrocarbon group, --COR.sup.1, --OR.sup.2, --COOR.sup.3, --CN, --CONH.sub.2, --NO.sub.2, --NR.sup.4 R.sup.5, a halogen atom, --SO.sub.4 R.sup.6, or --SO.sub.3 R.sup.7, in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, and R.sup.7 each represents a hydrogen atom or a hydrocarbon group; and n represents an integer of 4 to 12, provided that the plural X's or the plural Y's are the same or different, by oxidizing a sulfide bond in the compound. They have further found a process for producing the compound. The present invention has been completed based on these findings.
Accordingly, the present invention provides a cyclic phenol sulfide having at least one sulfinyl or sulfonyl group represented by formula (1): ##STR3## wherein X represents a hydrogen atom, a hydrocarbon group, or an acyl group; Y represents a hydrogen atom, a hydrocarbon group, a halogenated hydrocarbon group, --COR.sup.1, --OR.sup.2, --COOR.sup.3, --CN, --CONH.sub.2, --NO.sub.2, --NR.sup.4 R.sup.5, a halogen atom, --SO.sub.4 R.sup.6, or --S
REFERENCES:
Z. Aryan et al.: "Action of Sulfur Monochloride on Aromatic Ethers" Journal of the Chemical Society., 1962, pp. 4709-4712, XP000568857 Letchworth GB.
Kumagai, Hitoshi et al., "Facule Synthesis of p-tert-Butylthiacalix(4)arene by the Reaction of p-tert-Butylphenol with Elemental Sulfur in the Presence of a Base." Tetrahedron Letters, vol. 38, No. 22, Elserver Science Ltd. (England) (1997) pp. 3971-3972.
Sone, Tyo. et al., "Synthesis and Properties of Sulfur-Bridged Analog of p-tert-Butylthiacalix(4)arene." Tetrahedron, vol. 38, No. 22, Elserver Science Ltd. (England) (1997) pp. 10689-10698.
Kumagai Hitoshi
Miyanari Setsuko
Miyano Sotaro
Cosmo Oil Co. Ltd.
Cosmo Research Institute
Ramsuer Robert W.
Sackey Ebenezer
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