GB964980A - Process for the oxidation of cycloalkane carboxylic acid - Google Patents
Process for the oxidation of cycloalkane carboxylic acidInfo
- Publication number
- GB964980A GB964980A GB27549/61A GB2754961A GB964980A GB 964980 A GB964980 A GB 964980A GB 27549/61 A GB27549/61 A GB 27549/61A GB 2754961 A GB2754961 A GB 2754961A GB 964980 A GB964980 A GB 964980A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxylic acid
- metal
- water
- magnesium
- cycloalkane
- 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
- -1 cycloalkane carboxylic acid Chemical class 0.000 title abstract 7
- 230000003647 oxidation Effects 0.000 title abstract 5
- 238000007254 oxidation reaction Methods 0.000 title abstract 5
- 238000000034 method Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 6
- 239000005749 Copper compound Substances 0.000 abstract 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- 150000001880 copper compounds Chemical class 0.000 abstract 4
- 150000001925 cycloalkenes Chemical class 0.000 abstract 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract 4
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 abstract 4
- 229910052749 magnesium Inorganic materials 0.000 abstract 4
- 239000011777 magnesium Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910052788 barium Inorganic materials 0.000 abstract 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000001879 copper Chemical class 0.000 abstract 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910001385 heavy metal Inorganic materials 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 239000007791 liquid phase Substances 0.000 abstract 2
- 229910052748 manganese Inorganic materials 0.000 abstract 2
- 239000011572 manganese Substances 0.000 abstract 2
- 239000000155 melt Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 150000002736 metal compounds Chemical class 0.000 abstract 2
- OTCVAHKKMMUFAY-UHFFFAOYSA-N oxosilver Chemical class [Ag]=O OTCVAHKKMMUFAY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910001923 silver oxide Inorganic materials 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/2078—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by a transformation in which at least one -C(=O)-O- moiety is eliminated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/72—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
- Y02P20/129—Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Cycloalkanones and/or cycloalkenes and/or cycloalkenecarboxylic acids are obtained by reacting cycloalkane carboxylic acids in the liquid phase with oxygen at a temperature above 150 DEG C. in the presence of an oxidation catalyst comprising one or more metal compounds at least in part dissolved in the reaction liquid. The cycloalkanone and cycloalkene can be recovered by distillation. Water and/or water vapour promote the reaction and inhibit ester formation. The catalyst preferably comprises one or more copper compounds, e.g. an oxide or salt, the copper salt of the cycloalkane carboxylic acid being preferred. Magnesium and silver oxides and salts are also suitable. Copper compounds may be used together with a compound of another metal such as an alkali metal or alkaline earth metal, magnesium or barium or a heavy metal such as manganese. The cycloalkane carboxylic acid may be dissolved in water or an inert solvent or may be used in the form of a melt. Examples describe oxidation of cyclohexane carboxylic acid and cyclopentane carboxylic acid.ALSO:Cycloalkenes are obtained with cycloalkanones and/or cycloalkenecarboxylic acids by reacting cycloalkane carboxylic acids in the liquid phase with oxygen at a temperature above 150 DEG C. in the presence of an oxidation catalyst comprising one or more metal compounds at least in part dissolved in the reaction liquid. The cycloalkene can be recovered by distillation. Water and/or water vapour promote the reaction and inhibit ester formation. The preferred catalyst comprises one or more copper compounds, e.g. an oxide or salt, the copper salt of the cycloalkane carboxylic acid being preferred. Magnesium and silver oxides and salts are also suitable. Copper compounds may be used together with a compound of another metal such as an alkali metal or alkaline earth metal, magnesium or barium or a heavy metal such as manganese. The cycloalkane carboxylic acid may be dissolved in water or an inert solvent or may be used in the form of a melt. Examples describe oxidation of cyclohexane carboxylic acid and cyclopentane carboxylic acid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL254566 | 1960-08-04 | ||
| NL264222 | 1961-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB964980A true GB964980A (en) | 1964-07-29 |
Family
ID=26641728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27549/61A Expired GB964980A (en) | 1960-08-04 | 1961-07-28 | Process for the oxidation of cycloalkane carboxylic acid |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE606883A (en) |
| CH (1) | CH422767A (en) |
| ES (1) | ES269544A1 (en) |
| GB (1) | GB964980A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4393260A (en) | 1980-08-01 | 1983-07-12 | The Standard Oil Company | Preparation of cyclohexenyl compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6401389A (en) * | 1964-02-17 | 1965-08-18 |
-
1961
- 1961-07-28 GB GB27549/61A patent/GB964980A/en not_active Expired
- 1961-08-03 ES ES0269544A patent/ES269544A1/en not_active Expired
- 1961-08-03 BE BE606883A patent/BE606883A/en unknown
- 1961-08-03 CH CH913261A patent/CH422767A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4393260A (en) | 1980-08-01 | 1983-07-12 | The Standard Oil Company | Preparation of cyclohexenyl compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| ES269544A1 (en) | 1962-01-01 |
| CH422767A (en) | 1966-10-31 |
| BE606883A (en) | 1962-02-05 |
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| SU363693A1 (en) | METHOD FOR OBTAINING OXYBENZOPHENONOXYMES1 The invention relates to methods for producing organic compounds that can be used as complexing agents for the recovery of various valuable metals from aqueous solutions of their salts. A known method of producing oxybenzopheno-oximes by reacting benzoic acid chlorides with para-substituted phenols, followed by rearrangement of the resulting esters to oxybenzophenones, which are converted to the corresponding oximes by hydroxylamine hydrochloride in the presence of hydrogen chloride acceptors. And this method is its multi-stage, low yield of ketones at the rearrangement stage, the need to use hydroxylamine hydrochloride, aluminum chloride, and benzyl chloride. zoyl, pyridine, alkali. The purpose of the invention is to simplify the process. According to the proposed method for producing substituted hydroxybenzophenone oximes of the general formula: where R is OH; R2, R "- H, alkyl or alkoxy benzylphenol are photochemically oxidized with nitrosyl chloride or with a mixture of chlorine, nitric oxide and hydrogen chloride, in an inert solvent, followed by isolation of the target product in a known manner. Example 1020 Preparation 5- | |
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