GB1216699A - Cyclohexane-1,2,3,4,5,6-hexacarboxylic acid and its production - Google Patents
Cyclohexane-1,2,3,4,5,6-hexacarboxylic acid and its productionInfo
- Publication number
- GB1216699A GB1216699A GB2360668A GB2360668A GB1216699A GB 1216699 A GB1216699 A GB 1216699A GB 2360668 A GB2360668 A GB 2360668A GB 2360668 A GB2360668 A GB 2360668A GB 1216699 A GB1216699 A GB 1216699A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- cyclohexane
- anhydride
- absorption
- hexacarboxylic
- 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
Links
- DTGRIEIJTWNZQF-UHFFFAOYSA-N cyclohexane-1,2,3,4,5,6-hexacarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C(C(O)=O)C(C(O)=O)C1C(O)=O DTGRIEIJTWNZQF-UHFFFAOYSA-N 0.000 title abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 238000010521 absorption reaction Methods 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- OYUWHGGWLCJJNP-UHFFFAOYSA-N 1,2-Dihydrophthalic acid Chemical compound OC(=O)C1C=CC=CC1C(O)=O OYUWHGGWLCJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052750 molybdenum Inorganic materials 0.000 abstract 1
- 239000011733 molybdenum Substances 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 abstract 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/316—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with oxides of nitrogen or nitrogen-containing mineral acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
1,216,699. Cyclohexane - 1,2,3,4,5,6 - hexacarboxylic acid. BADISCHE ANILIN- & SODA-FABRIK A.G. 17 May, 1968 [20 May, 1967], No. 23606/68. Heading C2C. The invention comprises a cyclohexane- 1,2,3,4,5,6 - hexacarboxylic acid characterized by a melting-point of 222-224‹ C. and an NMR spectrum showing an absorption at 3-55 ppm and an absorption at 3.10 ppm indicating the presence of three axial hydrogen atoms and three equatorial hydrogen atoms. The acid may be prepared by oxidizing bicyclo - (2,2,2) - oct - 7 - en - 2,3,5,6 - tetracarboxylic acid and/or an anhydride thereof with nitric acid of 20-100% (by weight) concentration in the presence of an oxidation catalyst at 30-115‹ C. Suitable oxidation catalysts are, for example, compounds of palladium, molybdenum and vanadium. The tetracarboxylic acid and/or anhydride used as starting material may be prepared by the Diels-Alder reaction of maleic anhydride with cyclohexa-3,5-diene-1,2-dicarboxylic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0092625 | 1967-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1216699A true GB1216699A (en) | 1970-12-23 |
Family
ID=6986492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2360668A Expired GB1216699A (en) | 1967-05-20 | 1968-05-17 | Cyclohexane-1,2,3,4,5,6-hexacarboxylic acid and its production |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE715425A (en) |
| CH (1) | CH488647A (en) |
| DE (1) | DE1618162B1 (en) |
| FR (1) | FR1563486A (en) |
| GB (1) | GB1216699A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7157423B2 (en) | 2001-01-12 | 2007-01-02 | Fumapharm Ag | Fumaric acid amides |
| US7320999B2 (en) | 1998-11-19 | 2008-01-22 | Fumapharm Ag | Dimethyl fumarate for the treatment of multiple sclerosis |
| US7790916B2 (en) | 2002-04-18 | 2010-09-07 | Biogen Idec International Gmbh | Carbocyclic and oxacarbocyclic fumaric acid oligomers |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862217A (en) * | 1973-03-12 | 1975-01-21 | Basf Ag | Cyclohexane hexacarboxylic acid |
-
1967
- 1967-05-20 DE DE19671618162 patent/DE1618162B1/en not_active Ceased
-
1968
- 1968-05-16 FR FR1563486D patent/FR1563486A/fr not_active Expired
- 1968-05-16 CH CH724068A patent/CH488647A/en not_active IP Right Cessation
- 1968-05-17 GB GB2360668A patent/GB1216699A/en not_active Expired
- 1968-05-20 BE BE715425D patent/BE715425A/xx unknown
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7320999B2 (en) | 1998-11-19 | 2008-01-22 | Fumapharm Ag | Dimethyl fumarate for the treatment of multiple sclerosis |
| US7612110B2 (en) | 1998-11-19 | 2009-11-03 | Biogen Idec International Ag | Utilization of dialkylfumarates |
| US7619001B2 (en) | 1998-11-19 | 2009-11-17 | Biogen Idec International Gmbh | Utilization of dialkylfumarates |
| US7803840B2 (en) | 1998-11-19 | 2010-09-28 | Biogen Idec International Gmbh | Utilization of dialkylfumarates |
| US7915310B2 (en) | 1998-11-19 | 2011-03-29 | Biogen Idec International Gmbh | Utilization of dialkylfumarates |
| US8524773B2 (en) | 1998-11-19 | 2013-09-03 | Biogen Idec International Gmbh | Utilization of dialkylfumarates |
| US8759393B2 (en) | 1998-11-19 | 2014-06-24 | Biogen Idec International Gmbh | Utilization of dialkylfumarates |
| US7157423B2 (en) | 2001-01-12 | 2007-01-02 | Fumapharm Ag | Fumaric acid amides |
| US7432240B2 (en) | 2001-01-12 | 2008-10-07 | Biogen Idec International Gmbh | Fumaric acid amides |
| US7790916B2 (en) | 2002-04-18 | 2010-09-07 | Biogen Idec International Gmbh | Carbocyclic and oxacarbocyclic fumaric acid oligomers |
| US7906659B2 (en) | 2002-04-18 | 2011-03-15 | Biogen Idec International Gmbh | Carbocyclic and oxacarbocyclic fumaric acid oligomers |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1618162B1 (en) | 1971-05-19 |
| CH488647A (en) | 1970-04-15 |
| FR1563486A (en) | 1969-04-11 |
| BE715425A (en) | 1968-11-20 |
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