Cyclic phenol sulfide and process for producing the same

A cyclic phenol sulfide represented by the following formula (1):

• ##STR6## wherein X represents a hydrogen atom, a hydrocarbon group, or an acyl group;
• wherein Y.sub.1 represents a halogenated hydrocarbon group selected from the group consisting of a halogenated saturated aliphatic hydrocarbon group, a halogenated alicyclic hydrocarbon group, a halogenated alicyclic-aliphatic hydrocarbon group, a halogenated aromatic hydrocarbon group, and a halogenated aromatic-aliphatic hydrocarbon group;
• n is an integer of 3 or more;
• and
• m is an integer of 1 to 7,
• provided that the plural m's of the S.sub.m 's are the same or different;
• the plural X's are the same or different;
• and
• the plural Y.sub.1 's are the same or different.

A process for producing a cyclic phenol sulfide represented by the following formula (3):

• ##STR7## wherein Y.sub.2 represents a hydrogen atom or a hydrocarbon group;
• n is an integer of 3 or more;
• and
• m is an integer of 1 to 7,
• provided that the plural m's of the S.sub.m 's are the same or different;
• and
• the plural Y.sub.2 's are the same or different,
• which comprises a step of reacting a phenol represented by the following formula (2) with at least 0.1 gram equivalent of elemental sulfur in the presence of at least 0.005 gram equivalent of at least one metal reagent selected from the group consisting of alkali metal reagents and alkaline-earth metal reagents, each per gram equivalent of the phenol represented by formula (2):
• ##STR8## wherein said step of reacting a phenol is conducted while removing water and hydrogen sulfide.

A cyclic phenol sulfide represented by the following formula (1):

• ##STR10## wherein X represents a hydrogen atom;
• Y.sub.1 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;
• n is an integer of 5 or more;
• and
• m is an integer of 1 to 7,
• provided that the plural m's of the S.sub.m 's are the same or different;
• the plural X's are the same or different;
• and
• the plural Y.sub.1 's are the same or different.

A cyclic phenol sulfide represented by the following formula (1):

• ##STR11## wherein X represents a hydrogen atom, a hydrocarbon group, or an acyl group;
• Y.sub.1 represents a hydrogen atom, a methyl group, an isopropyl group, a neopentyl group, an n-hexyl group, a tert-octyl group, an isononyl group, a vinyl group, an allyl group, a cyclohexyl group, a 4-methylcyclohexenyl group, a phenyl group, a naphthyl group, a benzyl group, a hydrocarbon group derived from a polymer or copolymer of ethylene, propylene, butylene, acetylene, butadiene or isoprene, 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;
• n is an integer of 4;
• and
• m is an integer of 1 to 7,
• provided that the plural m's of the S.sub.m 's are the same or different;
• the plural X's are the same or different;
• and
• the plural Y.sub.1 's are the same or different.

A cyclic phenol sulfide represented by the following formula (1):

• ##STR12## wherein X represents a hydrogen atom or an acyl group;
• Y.sub.1 represents a hydrogen atom, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a neopentyl group, an n-hexyl group, a tert-octyl group, an isononyl group, a vinyl group, an allyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a phenyl group, a naphthyl group, a benzyl group, a hydrocarbon group derived from a polymer or copolymer of ethylene, propylene, butylene, acetylene, butadiene or isoprene, 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;
• n is an integer of 3;
• and
• m is an integer of 1 to 7,
• provided that the plural m's of the Sm's are the same or different.