Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
  • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/41—Preparation of salts of carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/41—Preparation of salts of carboxylic acids
  • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
  • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
  • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
  • C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids

Definitions

• This invention provides a high yield and high productivity process for preparing a hydroxy aromatic acid as described generally by the structure of Formula
• the arylene radical denoted by "-Ar-" is a multi-valent aromatic radical formed by the removal of two or more hydrogens from different carbon atoms on the aromatic ring, or on the aromatic rings when the structure is multicyclic.
• hydrogens may be removed from two up to all six carbon atoms on a benzyl ring, or hydrogens may be removed from any two and up to eight positions on either one or both rings of a naphthyl radical .
• the ligand may be a diketone described generally by Formula IV
• R 1 and R 2 are each independently selected from substituted and unsubstituted Ci-Ci 6 n-alkyl, iso-alkyl and tertiary alkyl groups; and substituted and unsubstituted C 6 - C 30 aryl and heteroaryl groups;
• R 4 , R 5 , R 6 and R 7 are each independently H or a substituted or unsubstituted Ci-Ci 6 n-alkyl, iso-alkyl or tertiary alkyl group;
• a diketone suitable for use herein as the ligand is 2,2' ,6,6' - tetramethylheptanedione-3 , 5 (Formula V) :
• a 2 , 5-dihydroxyterephthalic acid is disclosed as suitable for copolymeriztion with a dibasic acid and a glycol to prepare a heat-stabilized polyester in US 3,227,680 (which is incorporated in its entirety as a part hereof for all purposes) , wherein representative conditions involve forming a prepolymer in the presence of titanium tetraisopropoxide in butanol at 200-250 0 C, followed by solid-phase polymerization at 280 0 C at a pressure of 0.08 mm Hg.
• the pyridobisimidazole portion thereof may, however, be replaced by any or more of a benzobisimidazole, benzobisthiazole, benzobisoxazole, pyridobisthiazole and a pyridobisoxazole; and the 2 , 5-dihydroxy-p- phenylene portion thereof may be replace the derivative of one or more of isophthalic acid, terephthalic acid, 2,5-pyridine dicarboxylic acid, 2 , 6-naphthalene dicarboxylic acid, 4 , 4 ' -diphenyl dicarboxylic acid, 2 , 6-quinoline dicarboxylic acid, and 2,6-bis(4- carboxyphenyl ) pyridobisimidazole .
• HCl as used in the Examples denotes aqueous hydrochloric acid whose concentration is 35 grams of HCl per 100 mL of solution.
• the meaning of abbreviations is as follows “h” means hour(s), “mL” means milliliter (s) , “mmol” means millimole (s) , “NMR” means nuclear magnetic resonance spectroscopy, “CONV” means conversion (percent) , “SEL” means selectivity (percent), “T” means temperature, and "t” means time.
• the reaction mixture was acidified with HCl (cone), producing an off-white precipitate.
• the precipitate was filtered, washed with water and dried.
• the conversion and selectivity of salicylic acid were determined to be 100% and 94%, respectively, by 1 H NMR.
• the net yield was determined to be 94%.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
• Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

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• 2006
  • 2006-11-28 US US11/604,941 patent/US7351856B1/en not_active Expired - Fee Related
• 2007
  • 2007-11-28 CN CNA2007800433985A patent/CN101541730A/zh active Pending
  • 2007-11-28 EP EP07862262A patent/EP2086916A1/en not_active Withdrawn
  • 2007-11-28 WO PCT/US2007/024469 patent/WO2008066822A1/en not_active Ceased
  • 2007-11-28 KR KR1020097013244A patent/KR20090087089A/ko not_active Withdrawn
  • 2007-11-28 JP JP2009539294A patent/JP2010511045A/ja active Pending
• 2008
  • 2008-03-04 US US12/042,013 patent/US7592481B2/en not_active Expired - Fee Related

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