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(12) Patent Application Publication (10) Pub. No.: US 2002/0161255A1 Ishii Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2002/0161255A1 Ishii Et Al US 2002O161255A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2002/0161255A1 Ishii et al. (43) Pub. Date: Oct. 31, 2002 (54) PROCESS FOR PREPARING ORGANIC (52) U.S. Cl. ................................................. 558/40; 562/95 SULFURACDS OR SALTS THEREOF (76) Inventors: Yasutaka Ishii, Takatsuki-shi (JP); Tatsuya Nakano, Hyogo (JP) (57) ABSTRACT Correspondence Address: BRCH STEWART KOLASCH & BRCH A process for producing organic Sulfur acid or a Salt thereof PO BOX 747 of the present invention allows an organic Substrate to react FALLS CHURCH, VA 22040-0747 (US) with a Sulfur oxide in the presence of a metallic compound catalyst and in the absence of N-hydroxy and N-oxo cyclic (21) Appl. No.: 09/959,648 imide compounds and thereby yields a corresponding organic Sulfur acid or a Salt thereof. Such organic Substrates (22) PCT Filed: Feb. 27, 2001 include, for example, (a) homocyclic or heterocyclic com pounds having a methylene group, (b) compounds having a (86) PCT No.: PCT/JP01/01462 methine carbon atom, (c) compounds having a methyl group (30) Foreign Application Priority Data or methylene group at the adjacent position to an unsaturated bond, (d) non-aromatic heterocyclic compounds having a Mar. 2, 2000 (JP)....................................... O58055/2000 carbon-hydrogen bond at the adjacent position to a hetero atom, and (e) straight-chain alkanes. The Sulfur oxide Publication Classification includes, for example, Sulfur dioxide. This production pro ceSS can efficiently produce an organic Sulfur acid or a Salt (51) Int. Cl." ........................... C07C 35/02; CO7C 33/04 thereof under mild conditions. US 2002/0161255 A1 Oct. 31, 2002 PROCESS FOR PREPARING ORGANIC SULFUR aromatic heterocyclic compounds each having a carbon ACDS OR SALTS THEREOF hydrogen bond at the adjacent position to a hetero atom, and (e) straight-chain alkanes. TECHNICAL FIELD 0008. The term “N-hydroxy and N-oxo cyclic imide 0001. The present invention relates to a process for compounds’ Specifically means compounds represented by producing organic Sulfur acids or Salts thereof which are following Formula (1): useful, for example, as materials for pharmaceuticals, agro chemicals and dyes or as detergents. (1) BACKGROUND ART --R C 0002) A variety of processes are known for producing f \,... organic Sulfur acids or Salts thereof. For example, Such NX processes for producing a Sulfonic acid include a process of * / oxidizing a thiol or disulfide with an oxidizing agent, a --R2 process of allowing an aromatic hydrocarbon to react with O anhydrous SO-pyridine or chlorosulfuric acid by the use of a Friedel-Crafts reaction, and a process of Synthetically obtaining a Sulfonic acid by Subjecting an unsaturated com 0009 wherein R and Rare the same or different and are pound to free-radical addition. These processes, however, each a hydrogen atom, a halogen atom, an alkyl group, an require extreme reaction conditions or inevitably produce aryl group, a cycloalkyl group, a hydroxyl group, an alkoxy large amounts of by-products. Separately, few processes for group, a carboxyl group, an alkoxycarbonyl group or an acyl directly and efficiently Sulfonating non-aromatic hydrocar group, where R' and R may be combined to form a double bons have been known. bond or an aromatic or non-aromatic ring, X is an oxygen 0003. The Chemical Society of Japan, Spring Conference atom or a hydroxyl group, where one or two of N-Substituted Proceedings (1999) reports on a sulfonation reaction of a cyclic imido group indicated in the formula (1) may be hydrocarbon with Sulfur dioxide and oxygen by catalysis of further bonded to the aforementioned R, R or to the double N-hydroxyphthalimide. This process can yield a correspond bond or aromatic or non-aromatic ring formed together by ing Sulfonic acid from a hydrocarbon Such as adamantane R and R°. through one step. However, demands have been made on a proceSS for further efficiently producing Sulfonic acids and BEST MODE FOR CARRYING OUT THE other organic Sulfur acids or Salts thereof at a lower cost. INVENTION 0010 Organic Substrate DISCLOSURE OF INVENTION 0011. The Substrates for use in the invention are not 0004. Accordingly, an object of the present invention is to Specifically limited and include a wide variety of Saturated provide a proceSS for efficiently producing an organic Sulfur or unsaturated compounds. Such compounds include, but are acid or a Salt thereof under mild conditions. not limited to, hydrocarbons (aliphatic hydrocarbons, alicy 0005 Another object of the present invention is to pro clic hydrocarbons and aromatic hydrocarbons), heterocyclic vide a proceSS for directly and efficiently producing a compounds, alcohols, ethers, esters, ketones and aldehydes. corresponding Sulfur acid or a Salt thereof from a non Each of these Substrates can be used alone or in combina aromatic hydrocarbon. tion. 0006 After intensive investigations to achieve the above 0012 Preferred substrates include, but are not limited to, objects, the present inventors have found that, by using a (a) homocyclic or heterocyclic compounds each having a metallic compound as a catalyst, a corresponding organic methylene group, (b) compounds each having a methine sulfur acid or a salt thereof can efficiently be obtained from carbon atom, (c) compounds each having a methyl group or an organic Substrate and a Sulfur oxide even in the absence a methylene group at the adjacent position to an unsaturated of N-hydroxy and N-oxo cyclic imide compounds. The bond, (d) non-aromatic heterocyclic compounds each having present invention has been accomplished based on these a carbon-hydrogen bond at the adjacent position to a hetero findings. atom, and (e) Straight-chain alkanes. In these compounds, a Sulfur acid group Such as a Sulfonic acid group or Sulfinic 0007 Specifically, the present invention provides a pro acid group is introduced into the methylene group, methine ceSS for producing an organic Sulfur acid or a Salt thereof. carbon atom, methyl group or methylene group, carbon atom The proceSS includes the Step of allowing an organic Sub at the adjacent position to the hetero atom, and carbon atom Strate to react with a Sulfur oxide in the presence of a constituting the Straight-chain alkane, respectively. metallic compound catalyst and in the absence of N-hydroxy and N-oxo cyclic imide compounds to thereby yield a 0013) Of the compounds (a), homocyclic compounds (a1) corresponding organic Sulfur acid or a Salt thereof. The having a methylene group include, but are not limited to, Sulfur oxide includes, for example, Sulfur dioxide. Such cycloalkanes (e.g., cyclopropane, cyclobutane, cyclopen organic Substrates include, for example, (a) homocyclic or tane, cyclohexane, methylcyclohexane, 1,2-diethylcyclo heterocyclic compounds each having a methylene group, (b) hexane, isopropylcyclohexane, cycloheptane, cyclooctane, compounds each having a methine carbon atom, (c) com methylcyclooctane, cyclononane, cyclodecane, cyclodode pounds each having a methyl group or methylene group at cane, cyclotridecane, cyclotetradecane, cyclopentadecane, the adjacent position to an unsaturated bond, (d) non cyclohexadecane, cyclooctadecane, cyclononadecane, and US 2002/0161255 A1 Oct. 31, 2002 other Ca-Cao cycloalkanes), cycloalkenes (e.g., cyclopro ing to a junction position when two rings commonly possess pene, cyclobutene, cyclopentene, cyclohexene, 1-methyl-1- two atoms), and a Sulfur acid group is introduced into the cyclohexene, cycloheptene, cyclooctene, cyclononene, methine carbon atom. cyclodecene, cyclododecene, and other C-C cycloalk 0018 The non-aromatic cyclic compounds (b3) each enes), cycloalkadienes (e.g., cyclopentadiene, cyclohexadi having a hydrocarbon group bonded to its ring include, for ene, cycloheptadiene, cyclooctadiene, cyclodecadiene, example, 1-methylcyclopentane, 1-methylcyclohexane, cyclododecadiene, and other Cs-Co cycloalkadienes), limonene, menthene, menthol, carvomenthone, menthone, cycloalkatrienes, cycloalkatetraenes, and condensed polycy and other alicyclic hydrocarbons each having from about 3 clic aromatic hydrocarbons each having a 5-to 8-membered to about 15 members and having a hydrocarbon group (e.g., non-aromatic ring condensed there with. an alkyl group) each having from about 1 to about 20 (preferably from about 1 to about 10) carbon atoms and 0014) Of the compounds (a), heterocyclic compounds being bonded to its ring, and derivatives of these com (a2) each having a methylene group include, for example, 5 pounds. In these compounds (b3), a Sulfur acid group is or 6-membered cyclic compounds having a hetero atom introduced into a methine carbon atom at the bonding site Selected from nitrogen, oxygen and Sulfur atoms, or con between the constitutive ring and the hydrocarbon group. densed heterocyclic compounds having an aromatic ring and 0019. The compounds (c) each having a methyl group or a 5- or 6-membered ring having a hetero atom condensed to a methylene group at the adjacent position to an unsaturated the aromatic ring. Examples of Such heterocyclic com bond include (c1) organic compounds each having a methyl pounds (a2) are dihydrofuran, tetrahydrofuran, pyran, dihy group or a methylene group at the adjacent position to a dropyran, tetrahydropyran, piperidine, piperazine, pyrroli non-aromatic carbon-carbon double bond and/or triple bond, dine and Xanthene. In the compounds (a), a Sulfur acid group (c2) compounds each having a methyl group or a methylene is introduced into the methylene group constituting a non group at the adjacent position to an aromatic ring, and (c3) aromatic ring. compounds each having a methyl group or a methylene 0.015 The compounds (b) each having a methine carbon group at the adjacent position to a carbonyl group. atom (a methylidyne group) include, for example, (b1) chain 0020. The compounds (c1) include, but are not limited to, hydrocarbons each having a tertiary carbon atom, (b2) unsaturated chain hydrocarbons each having from about 3 to bridged cyclic compounds and (b3) non-aromatic cyclic about 12 carbon atoms, Such as propylene, 1-butene, compounds each having a hydrocarbon group bonded to its 2-butene, butadiene, 1-pentene, 2-pentene, isoprene, 1-hex ring.
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