GB670929A - Improvements in or relating to a method of preparing uronic acids and derivaties thereof - Google Patents

Improvements in or relating to a method of preparing uronic acids and derivaties thereof

Info

Publication number
GB670929A
GB670929A GB10003/50A GB1000350A GB670929A GB 670929 A GB670929 A GB 670929A GB 10003/50 A GB10003/50 A GB 10003/50A GB 1000350 A GB1000350 A GB 1000350A GB 670929 A GB670929 A GB 670929A
Authority
GB
United Kingdom
Prior art keywords
per cent
acid
glycoside
nitric acid
oxidation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB10003/50A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Corn Products Refining Co
Original Assignee
Corn Products Refining Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Corn Products Refining Co filed Critical Corn Products Refining Co
Publication of GB670929A publication Critical patent/GB670929A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • C07H7/02—Acyclic radicals
    • C07H7/033—Uronic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

Glycosides are oxidized to glycuronosides with 65-100 per cent nitric acid at 20-100 DEG C. in the presence of nitrous acid, a nitrite salt or nitrogen trioxide gas, there being at least one mol. of nitric acid per mol. of glycoside. Preferred conditions are 30-45 DEG C. for 8-20 hours. Thus a solution of a glycoside and sodium nitrite in 65-75 per cent nitric acid is prepared at 45-50 DEG C. and maintained at 35-45 DEG C. for 8-20 hours. The reaction mixture is then heated to 90-100 DEG C. to remove excess oxidant, preferably with 0.5-1 per cent of formaldehyde (or methanol) and the glycuronoside purified by solvent-extraction and/or adsorption. Dicarboxylic acids are precipitated as calcium or barium salts. Finally, hydrolysis is effected with an acid or a cation-exchange resin, the glycuronic acid or its lactone being obtained by crystallisation. If sodium nitrite is used as oxidation catalyst, it may amount to 0.1-0.5 per cent by weight of glycoside. Alternatively, the by-product gases from a previous oxidation may be used as catalyst. Examples show the preparation of methyl-, ethyl- and cyclohexyl-glucuronides from the corresponding glucosides, and glucuronolactone by hydrolysis. Other examples show the oxidation of trehalose and starch to uronic acids.
GB10003/50A 1949-12-17 1950-04-24 Improvements in or relating to a method of preparing uronic acids and derivaties thereof Expired GB670929A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US670929XA 1949-12-17 1949-12-17

Publications (1)

Publication Number Publication Date
GB670929A true GB670929A (en) 1952-04-30

Family

ID=22073654

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10003/50A Expired GB670929A (en) 1949-12-17 1950-04-24 Improvements in or relating to a method of preparing uronic acids and derivaties thereof

Country Status (1)

Country Link
GB (1) GB670929A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0864580A2 (en) * 1997-03-10 1998-09-16 Chugoku Kayaku Kabushiki Kaisha Process for producing D-glucuronolactone
WO2016081260A1 (en) * 2014-11-18 2016-05-26 Rivertop Renewables, Inc. Compositions comprising oxidized starch and processes for making the compositions
US9758462B2 (en) 2013-03-13 2017-09-12 Rivertop Renewables, Inc. Nitric acid oxidation processes

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0864580A2 (en) * 1997-03-10 1998-09-16 Chugoku Kayaku Kabushiki Kaisha Process for producing D-glucuronolactone
EP0864580A3 (en) * 1997-03-10 1998-11-04 Chugoku Kayaku Kabushiki Kaisha Process for producing D-glucuronolactone
US5912361A (en) * 1997-03-10 1999-06-15 Chugoku Kayaku Kabushiki Kaisha Process for producing D-glucuronolactone
US9758462B2 (en) 2013-03-13 2017-09-12 Rivertop Renewables, Inc. Nitric acid oxidation processes
WO2016081260A1 (en) * 2014-11-18 2016-05-26 Rivertop Renewables, Inc. Compositions comprising oxidized starch and processes for making the compositions

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