Processes for the preparation of 2,5-dihydroxybenzenesulfonic acid salts of formula (I) and a crystalline form of potassium 2,5 2,5-dihydroxybenzenesulfonic acid are provided. ##STR00001##

A monomer has the structure

##STR00001##

wherein R is an organic group comprising a polymerizable carbon-carbon double bond or carbon-carbon triple bond; X and Y are independently at each occurrence hydrogen or a non-hydrogen substituent; EWG1 and EWG2 are independently at each occurrence an electron-withdrawing group; p is 0, 1, 2, 3, or 4; n is 1, 2, 3, or 4; and M.sup.+ is an organic cation. A polymer prepared from monomer is useful as a component of a photoresist composition.

A quinone derivative with a high redox potential that does not undergo Michael addition or proto-desulfonation. This molecule addresses the key issues faced with the positive side material of an aqueous all-organic flow battery. This new molecule is 2,5-dihydroxy-4,6-dimethylbenzene-1,3-disulfonic acid (or the disulfonate salt thereof). This quinone derivative offers good solubility, electrochemical reversibility, and robustness to charge/discharge cycling. Quinones with reduced crossover are also provided.

A quinone derivative with a high redox potential that does not undergo Michael addition or proto-desulfonation. This molecule addresses the key issues faced with the positive side material of an aqueous all-organic flow battery. This new molecule is 2,5-dihydroxy-4,6-dimethylbenzene-1,3-disulfonic acid (or the disulfonate salt thereof). This quinone derivative offers good solubility, electrochemical reversibility, and robustness to charge/discharge cycling. Quinones with reduced crossover are also provided.

A quinone derivative with a high redox potential that does not undergo Michael addition or proto-desulfonation. This molecule addresses the key issues faced with the positive side material of an aqueous all-organic flow battery. This new molecule is 2,5-dihydroxy-4,6-dimethylbenzene-1,3-disulfonic acid (or the disulfonate salt thereof). This quinone derivative offers good solubility, electrochemical reversibility, and robustness to charge/discharge cycling. Quinones with reduced crossover are also provided.

A method for the manufacture of a sulfonated phenol for use as a cumene hydroperoxide decomposition catalyst can comprise: combining phenol and a sulfonating agent at a first temperature that is 1° C. to 15° C. higher than a melting temperature of the phenol, to form a reaction mixture at the first temperature; reducing the first temperature of the reaction mixture to a second temperature that is 10 to 40° C. lower than the first temperature; and forming the sulfonated phenol at the second temperature.

A method for the manufacture of a sulfonated phenol for use as a cumene hydroperoxide decomposition catalyst can comprise: combining phenol and a sulfonating agent at a first temperature that is 1° C. to 15° C. higher than a melting temperature of the phenol, to form a reaction mixture at the first temperature; reducing the first temperature of the reaction mixture to a second temperature that is 10 to 40° C. lower than the first temperature; and forming the sulfonated phenol at the second temperature.

An actinic ray-sensitive or radiation-sensitive resin composition containing (A) an acid-decomposable resin, (B) a compound represented by General Formula (b1), and (C) a compound represented by General Formula (c1), in which a ratio of a content of the compound (C) to a content of the compound (B) is from 0.01% by mass to 10% by mass. In the formulae, L represents a single bond or a divalent linking group. A represents a group that decomposes by the action of an acid. B represents a group that decomposes by the action of an acid, a hydroxy group, or a carboxy group. It should be noted that at least one B represents the hydroxy group or the carboxy group. n represents an integer from 1 to 5. X represents an (n+1)-valent linking group. M.sup.+ represents a sulfonium ion or an iodonium ion.

##STR00001##

The present invention provides a method for preparing a compound of Formula C, Formula D, or Formula F: ##STR00001## wherein each R.sup.1, R.sup.2, and R.sup.3 is independently H, SF.sub.5, N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), C(═S)N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), SO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), OSO.sub.2(C.sub.1-C.sub.8 alkyl), OSO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), N(C.sub.1-C.sub.8 alkyl)SO.sub.2(C.sub.1-C.sub.8 alkyl), or C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 haloalkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.10 cycloalkyl, C.sub.3-C.sub.10 halocycloalkyl, C.sub.4-C.sub.10 alkylcycloalkyl, C.sub.4-C.sub.10 cycloalkylalkyl, C.sub.6-C.sub.14 cycloalkylcycloalkyl, C.sub.5-C.sub.10 alkylcycloalkylalkyl, C.sub.3-C.sub.8 cycloalkenyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.3-C.sub.8 cycloalkoxy, C.sub.3-C.sub.8 halocycloalkoxy, C.sub.4-C.sub.10 cycloalkylalkoxy, C.sub.2-C.sub.8 alkenyloxy, C.sub.2-C.sub.8 alkynyloxy, C.sub.1-C.sub.8 alkylthio, C.sub.1-C.sub.8 alkylsulfinyl, C.sub.1-C.sub.8 alkylsulfonyl, C.sub.3-C.sub.8 cycloalkylthio, C.sub.3-C.sub.8 cycloalkylsulfinyl, C.sub.3-C.sub.8 cycloalkylsulfonyl, C.sub.4-C.sub.10 cycloalkylalkylthio, C.sub.4-C.sub.10 cycloalkylalkylsulfinyl, C.sub.4-C.sub.10 cycloalkylalkylsulfonyl, C.sub.2-C.sub.8 alkenylthio, C.sub.2-C.sub.8 alkenylsulfinyl, C.sub.2-C.sub.8 alkenylsulfonyl, C.sub.2-C.sub.8 alkynylthio, C.sub.2-C.sub.8 alkynylsulfinyl, C.sub.2-C.sub.8 alkynylsulfonyl, or phenyl; or two of R.sup.1, R.sup.2, and R.sup.3 on adjacent ring atoms may be taken together to form a 5- to 7-membered carbocyclic or heterocyclic ring, each ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 3 N, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and such ring is optionally substituted with up to 3 substituents independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.8 alkylcycloalkyl, C.sub.4-C.sub.8 haloalkylcycloalkyl, C.sub.4-C.sub.8 cycloalkylalkyl, C.sub.4-C.sub.8 halocycloalkylalkyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.2-C.sub.8 alkoxycarbonyl, C.sub.2-C.sub.6 haloalkoxycarbonyl, C.sub.2-C.sub.6 alkylcarbonyl and C.sub.2-C.sub.6 haloalkylcarbonyl; and M is an inorganic cation or organic cation.

The present invention provides a method for preparing a compound of Formula C, Formula D, or Formula F: ##STR00001## wherein each R.sup.1, R.sup.2, and R.sup.3 is independently H, SF.sub.5, N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), C(═S)N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), SO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), OSO.sub.2(C.sub.1-C.sub.8 alkyl), OSO.sub.2N(C.sub.1-C.sub.8 alkyl)(C.sub.1-C.sub.8 alkyl), N(C.sub.1-C.sub.8 alkyl)SO.sub.2(C.sub.1-C.sub.8 alkyl), or C.sub.1-C.sub.8 alkyl, C.sub.1-C.sub.8 haloalkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, C.sub.3-C.sub.10 cycloalkyl, C.sub.3-C.sub.10 halocycloalkyl, C.sub.4-C.sub.10 alkylcycloalkyl, C.sub.4-C.sub.10 cycloalkylalkyl, C.sub.6-C.sub.14 cycloalkylcycloalkyl, C.sub.5-C.sub.10 alkylcycloalkylalkyl, C.sub.3-C.sub.8 cycloalkenyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.3-C.sub.8 cycloalkoxy, C.sub.3-C.sub.8 halocycloalkoxy, C.sub.4-C.sub.10 cycloalkylalkoxy, C.sub.2-C.sub.8 alkenyloxy, C.sub.2-C.sub.8 alkynyloxy, C.sub.1-C.sub.8 alkylthio, C.sub.1-C.sub.8 alkylsulfinyl, C.sub.1-C.sub.8 alkylsulfonyl, C.sub.3-C.sub.8 cycloalkylthio, C.sub.3-C.sub.8 cycloalkylsulfinyl, C.sub.3-C.sub.8 cycloalkylsulfonyl, C.sub.4-C.sub.10 cycloalkylalkylthio, C.sub.4-C.sub.10 cycloalkylalkylsulfinyl, C.sub.4-C.sub.10 cycloalkylalkylsulfonyl, C.sub.2-C.sub.8 alkenylthio, C.sub.2-C.sub.8 alkenylsulfinyl, C.sub.2-C.sub.8 alkenylsulfonyl, C.sub.2-C.sub.8 alkynylthio, C.sub.2-C.sub.8 alkynylsulfinyl, C.sub.2-C.sub.8 alkynylsulfonyl, or phenyl; or two of R.sup.1, R.sup.2, and R.sup.3 on adjacent ring atoms may be taken together to form a 5- to 7-membered carbocyclic or heterocyclic ring, each ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 3 N, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and such ring is optionally substituted with up to 3 substituents independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 haloalkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.2-C.sub.4 haloalkynyl, C.sub.3-C.sub.7 cycloalkyl, C.sub.3-C.sub.7 halocycloalkyl, C.sub.4-C.sub.8 alkylcycloalkyl, C.sub.4-C.sub.8 haloalkylcycloalkyl, C.sub.4-C.sub.8 cycloalkylalkyl, C.sub.4-C.sub.8 halocycloalkylalkyl, C.sub.1-C.sub.8 alkoxy, C.sub.1-C.sub.8 haloalkoxy, C.sub.2-C.sub.8 alkoxycarbonyl, C.sub.2-C.sub.6 haloalkoxycarbonyl, C.sub.2-C.sub.6 alkylcarbonyl and C.sub.2-C.sub.6 haloalkylcarbonyl; and M is an inorganic cation or organic cation.