US2575014A - Production of aliphatic di-ketones - Google Patents
Production of aliphatic di-ketones Download PDFInfo
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- US2575014A US2575014A US85709A US8570949A US2575014A US 2575014 A US2575014 A US 2575014A US 85709 A US85709 A US 85709A US 8570949 A US8570949 A US 8570949A US 2575014 A US2575014 A US 2575014A
- Authority
- US
- United States
- Prior art keywords
- ketones
- ferrous
- hydroperoxide
- parts
- solution
- 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 - Lifetime
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- 238000004519 manufacturing process Methods 0.000 title description 5
- 125000001931 aliphatic group Chemical group 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical group 0.000 claims description 11
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 1
- 150000002978 peroxides Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 8
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 7
- 239000011790 ferrous sulphate Substances 0.000 description 7
- 235000003891 ferrous sulphate Nutrition 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000002432 hydroperoxides Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- -1 Alicyclic hydrocarbons Chemical class 0.000 description 4
- XMJFMFGBHULZBR-UHFFFAOYSA-N CC1CCCC1.OO Chemical compound CC1CCCC1.OO XMJFMFGBHULZBR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IFTRQJLVEBNKJK-UHFFFAOYSA-N Ethylcyclopentane Chemical compound CCC1CCCC1 IFTRQJLVEBNKJK-UHFFFAOYSA-N 0.000 description 2
- DKKCQDROTDCQOR-UHFFFAOYSA-L Ferrous lactate Chemical compound [Fe+2].CC(O)C([O-])=O.CC(O)C([O-])=O DKKCQDROTDCQOR-UHFFFAOYSA-L 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Chemical compound CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- MCDLETWIOVSGJT-UHFFFAOYSA-N acetic acid;iron Chemical compound [Fe].CC(O)=O.CC(O)=O MCDLETWIOVSGJT-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 229960002089 ferrous chloride Drugs 0.000 description 2
- 239000004225 ferrous lactate Substances 0.000 description 2
- 235000013925 ferrous lactate Nutrition 0.000 description 2
- 229940037907 ferrous lactate Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PERHPCPROKAJEC-UHFFFAOYSA-N hydrogen peroxide;methylcyclohexane Chemical compound OO.CC1CCCCC1 PERHPCPROKAJEC-UHFFFAOYSA-N 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 2
- 235000014413 iron hydroxide Nutrition 0.000 description 2
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 2
- 125000002081 peroxide group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- TVSBRLGQVHJIKT-UHFFFAOYSA-N propan-2-ylcyclopentane Chemical compound CC(C)C1CCCC1 TVSBRLGQVHJIKT-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- VTIBBOHXBURHMD-UHFFFAOYSA-N 1,2,3,4,4a,5,10,10a-octahydroanthracene Chemical compound C1=CCC2CC(CCCC3)C3=CC2=C1 VTIBBOHXBURHMD-UHFFFAOYSA-N 0.000 description 1
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WZCNWCLFWMINNF-UHFFFAOYSA-N dodecane-2,3-dione Chemical compound CCCCCCCCCC(=O)C(C)=O WZCNWCLFWMINNF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
Definitions
- the present invention is for a process for producing aliphatic di-ketones, in particular long chain di-ketones, and their derivatives bythe treatment of peroxidic compounds, and to compounds produced thereby.
- the principal object of the invention is to produce a simple process for the production of such di-ketones and to produce useful products thereby.
- the invention accordingly comprises the novel products as well as the novel processes and steps of processes according to which such products are manufactured, the specific. embodiments of which are described hereinafter by way of ex;- ample and in accordance, with which it is now preferred to practice the invention. 7
- a suitable ferrous salt is, for instance, ferrous. sulphate, which is preferably used in aqueous solution.
- Other ferrous salts are, for example, ferrous chloride, ferrous acetate, ferrous lactate.
- cyclopentane isopropyl cyclopentane, methyl c'yclohexane, ethyl cyclohexane, isopropyl cyclohexane.
- the proportion of the components of the reaction may vary.
- the process according to this invention ma ,be carriedout by bringing the hydroperoxide of the said alicyclic hydrocarbons into intimate contact with for instance, ferrous sulphate, preferably in aqueous solution.
- the reaction may be carried out with a solution of the hydroperoxide for instance in the unchanged 'alicyclic hydrocarbon which contains only a small percentage of the hydroperoxide.
- solutions are obtained in the well known way for instance j when the alicyclic hydrocarbon is oxidised by means of molecular oxygen for the preparation "of its hydroperoxide without separating the latter from the unchanged hydrocarbon.
- the process of this invention for c to the process of this invention is exothermic so the production of aliphatic di-ketones comprises carry out" the reaction in acid solution, preferably g acidified by mineral acid such as sulphuric acid.
- the amount of acid is conveniently such as to prevent the iron from-being precipitated. 1
- the di-ketone formed may be separated by, forinstance, decanting the organic solution from the aqueous phase and subsequently distilling the organic solution whereby unreacted hydrocarbon which served as a solvent, 'distils off.
- hydrocarbon any alcohols and/or mono-ketones which are present in the reaction mixture distil From the residue the di-ketone over as well. Crystallises out or may be precipitated therefrom by the addition of a liquid for instance petrol ether in which the di-ketone is insoluble.
- the di-ketones produced according to the process of this invention may be used for the preparation by oxidation of di-basic acids such as sebacic acid, suberic acid and the like.
- Example 3 10 parts of methylcyclopetane hydroperoxide (87.2% pure) dissolved in 10 parts of ethanol were added slowly with stirring to a solution of 30 parts of crystalline ferrous sulphate, '7 parts of sulphuric acid, 32 parts of ethanol, and 70 parts of water. 4.4 parts of dodecanedione-Zzll were obtained which was isolated by filtration.
- Example 4 10 parts of methylcyclopentane hydroperoxide (95.6% pure) was converted into its sodium salt by dissolution in the calculated quantity of 10% sodium hydroxide solution, and the aqueous solution soobtained was added slowly with stirring to a solution of 30 parts of crystalline ferrous sulphate made up to 100 parts with water. The precipitated iron hydroxide was dissolved by acidification, and the organic product was isolated by extraction with ether. 2.9 parts of dodecanedione-2:11 and 2.6 parts of a fraction consisting of alcohols and mono-ketones were thereby obtained.
- a process which comprises reacting the oxidate solution resulting from reacting the alkyl substituted saturated alicyclic hydrocarbon ring "selected from the group consisting of cyclopentane and cyclohexane with molecular oxygen-to convert part of said hydrocarbon into the corresponding hydroperoxide so that unreacted hydro- ,carbon is present, with aqueous ferrous salt solu- "tion and recovering t di-ketone produced thereby from its solution in the unreacted hydrocarbon.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Nov. 13, 1951 \PATEN T OFFICE I 1 PRODUCTION OF ALIPHATIC DI-KETVONEVSV Edwin George Edward Hawkins, Lower Kingswood, Tadworth, England, assignor to The Distillers Company Limited, Edinburgh, Scotland,
a British company No'Drawing. Application A ril5, 1949, Serial No. 85,709. In Great Britain April 29, 1948 The present invention is for a process for producing aliphatic di-ketones, in particular long chain di-ketones, and their derivatives bythe treatment of peroxidic compounds, and to compounds produced thereby.
It is known that hydroperoxides on reacting with ferrous sulphateyield ketones. Hook and Lang have described in Ber. 75 (1 942) 1 51 and Ber. '76 (1943) 1130 that the hydroperoxides of, indane and octa hydroanthracene react when heated with aqueous ferrous sulphate solution and are decomposed catalytically with the formation of ketones which possess the same number; of carbon atoms. The same applies to ethylbenzene hydroperoxide which yields acetophenone on being heated with an aqueous ferrous sol-- phate solution (ibidern 76 (1943) 172).
It has now been discovered in accordance with this invention that hydroperoxides of compounds wherein the peroxide group is attached to a tertiary carbon atom, which forms part ,ofthe saturated alicyclic hydrocarbon ring of cyclopentane or cyclohexane and at the same time. is
linked to an alkyl group attached to said ring,
react with ferrous compounds with the production of di-ketones. Fission of the linkage between the tertiary carbon atomand an adjacent carbon atom in the ring takes place and at the same time identical radicals link up together so' that di-ketones with double the. number of carbon atoms in the molecule are formed. The following formula for methyl cyclopentane hydro-- peroxide illustrates the reaction occurring:
0 onaaLqoHcr -cn.
The principal object of the invention is to produce a simple process for the production of such di-ketones and to produce useful products thereby. A I
The invention accordingly comprises the novel products as well as the novel processes and steps of processes according to which such products are manufactured, the specific. embodiments of which are described hereinafter by way of ex;- ample and in accordance, with which it is now preferred to practice the invention. 7
6 Claims. ((21.2'60-593) 2 reacting with a solution of a ferrous salt a hydroperoxide of an alkyl substituted alicyclic hydro-v carbon ringselected from the group consisting off cyclopentane and cyclohexane wherein the peroxide group is attachedto a tertiary carbon atom.
which forms part of said hydrocarbon ring andwhich is also attached to said alkyl group, the. di-ketones produced having twice as many car- Do bon atoms as the said ring compound.
A suitable ferrous salt is, for instance, ferrous. sulphate, which is preferably used in aqueous solution. Other ferrous salts are, for example, ferrous chloride, ferrous acetate, ferrous lactate.
,Alicyclic hydrocarbons, the hydroperoxides ;of{, -which may be subjected to the treatment of thei present invention and thereby yield di-k'etones, arefor instancebut without limitation thereto. methyl cyclopentane, ethyl cyclopentane, pr'opyl.
. cyclopentane, isopropyl cyclopentane, methyl c'yclohexane, ethyl cyclohexane, isopropyl cyclohexane. The proportion of the components of the reaction may vary.
The process according to this invention ma ,be carriedout by bringing the hydroperoxide of the said alicyclic hydrocarbons into intimate contact with for instance, ferrous sulphate, preferably in aqueous solution. Alternatively, the reaction may be carried out with a solution of the hydroperoxide for instance in the unchanged 'alicyclic hydrocarbon which contains only a small percentage of the hydroperoxide. Such solutions are obtained in the well known way for instance j when the alicyclic hydrocarbon is oxidised by means of molecular oxygen for the preparation "of its hydroperoxide without separating the latter from the unchanged hydrocarbon. In this case, it is preferred to treat the hydroperoxi'decontaining reaction mixture resulting from" the oxidation process with water or a solution of aqueous solution. It is preferred, however, to
Accordingly the process of this invention for c to the process of this invention is exothermic so the production of aliphatic di-ketones comprises carry out" the reaction in acid solution, preferably g acidified by mineral acid such as sulphuric acid. The amount of acid is conveniently such as to prevent the iron from-being precipitated. 1 The reaction of: the hydroperoxides according out and may be recovered directly by filtration.-
When a" solution of the hydroperoxide in unreacted hydrocarbon such as the crude oxidate, is
treated according to the present invention the di-ketone formed may be separated by, forinstance, decanting the organic solution from the aqueous phase and subsequently distilling the organic solution whereby unreacted hydrocarbon which served as a solvent, 'distils off. With the hydrocarbon any alcohols and/or mono-ketones which are present in the reaction mixture distil From the residue the di-ketone over as well. crystallises out or may be precipitated therefrom by the addition of a liquid for instance petrol ether in which the di-ketone is insoluble.
As by-products of the reaction with the ferrous salt according to the invention, alcohols and mono-ketones are produced. In the case of methyl cyclopentane hydroperoxide the ketone formed as such a by-product is mainly methylbutyl ketone. These alcohols and mono-ketones may be removed if desired by distillation. The ferric compounds produced during the reaction by oxidation of the ferrous compounds may be reconverted to ferrous compounds by reduction, for instance with sulphur dioxide.
The di-ketones produced according to the process of this invention may be used for the preparation by oxidation of di-basic acids such as sebacic acid, suberic acid and the like.
-The following examples illustrate the manner in which the process of the invention may be carried out in practice the quantities given being parts by weight.
Example 1 parts of methyl cyclopentane hydroperoxide were shaken at room temperature with 100 parts of water in which 62 parts of crystalline ferrous sulphate had been dissolved. The temperature of the reaction mixture rose considerably whilst a brown iron hydroxide deposit settled out. The reaction mixture after having been cooled was Example 2 '20 parts of methyl cyclohexane hydroperoxide were heated on a water bath for 3 hours with an aqueous solution containing parts of crystalline ferrous sulphate. The product was ether extracted and distilled. A fraction containing ketones and alcohols was obtained, weighing 15.0
parts,- whilst 1.7 parts of a fraction consisting 1 mainly of tetradecanedione-2213 was obtained. This di-ketone is insoluble in water, and soluble in most organic solvents. It crystallises in white shining leaflets with a M. P. of 76-77" C.
Example 3 10 parts of methylcyclopetane hydroperoxide (87.2% pure) dissolved in 10 parts of ethanol were added slowly with stirring to a solution of 30 parts of crystalline ferrous sulphate, '7 parts of sulphuric acid, 32 parts of ethanol, and 70 parts of water. 4.4 parts of dodecanedione-Zzll were obtained which was isolated by filtration.
A similar experiment in which the sulphuric acid was omitted yielded only 3.2 parts of dodecanedione.
. v Example 4 10 parts of methylcyclopentane hydroperoxide (95.6% pure) was converted into its sodium salt by dissolution in the calculated quantity of 10% sodium hydroxide solution, and the aqueous solution soobtained was added slowly with stirring to a solution of 30 parts of crystalline ferrous sulphate made up to 100 parts with water. The precipitated iron hydroxide was dissolved by acidification, and the organic product was isolated by extraction with ether. 2.9 parts of dodecanedione-2:11 and 2.6 parts of a fraction consisting of alcohols and mono-ketones were thereby obtained.
Equivalent quantities of ferrous chloride, ferrous acetate and ferrous lactate may be used in,
said ring compound.
2. A process according to claim 1 wherein the solution of the ferrous salt is an aqueous solution of ferrous sulphate.
3. A process according to claim 1 wherein the reaction is effected under acid conditions.
4. A process according to claim 1 wherein the hydroperoxide is methyl cyclopentane hydroperoxide.
5. A process according to claim 1 wherein the hydroperoxide is methyl cyclohexane hydroperoxide.
6. A process which comprises reacting the oxidate solution resulting from reacting the alkyl substituted saturated alicyclic hydrocarbon ring "selected from the group consisting of cyclopentane and cyclohexane with molecular oxygen-to convert part of said hydrocarbon into the corresponding hydroperoxide so that unreacted hydro- ,carbon is present, with aqueous ferrous salt solu- "tion and recovering t di-ketone produced thereby from its solution in the unreacted hydrocarbon.
I EDWIN GEORGE EDWARD HAWKINS.
REFERENCES CITED The following references are of record in the file of this patent:
Work, J. Chem. Soc., 1940 vol., pages 1307-1315.
fHock et al., Berichte, vol. 75, pages 1051-1054 (1942); vol. 76, pages 1130-1131 (1943); vol. 76, pages 169-172 (1943).
Claims (1)
1. A PROCESS WHICH COMPRISES REACTING WITH A SOLUTION OF A FERROUS SALT IN THE PRESENCE OF SOME WATER, A HYDROPEROXIDE IN THE ALKYL SUBSTITUTED SATURATED ALICYCLIC HYDROCARBON RING SELECTED FROM THE GROUP CONSISTING OF CYCLOPENTANE AND CYCLOHEXANE WHEREIN THE PEROXIDE GROUP IS ATTACHED TO A TERTIARY CARBON ATOM WHICH FORMS PART OF SAID HYDROCARBON RIGN AND IS ALSO ATTACHED TO SAID ALKYL GROUP, THE DI-KETONE PRODUCED HAVING TWICE AS MANY CARBON ATOMS AS THE SAID RING COMPOUND.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2575014X | 1948-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2575014A true US2575014A (en) | 1951-11-13 |
Family
ID=10910522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US85709A Expired - Lifetime US2575014A (en) | 1948-04-29 | 1949-04-05 | Production of aliphatic di-ketones |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2575014A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2671810A (en) * | 1952-05-24 | 1954-03-09 | Du Pont | Long-chain diketones |
| US2700057A (en) * | 1952-03-28 | 1955-01-18 | Du Pont | Process for preparing 2, 13-tetradecanedione from 1-methylcyclohexyl hydroperoxide |
| US2798096A (en) * | 1954-02-17 | 1957-07-02 | Exxon Research Engineering Co | Production of cyclic hydroperoxides |
| US2822399A (en) * | 1953-05-01 | 1958-02-04 | Du Pont | Manufacture of diketones |
-
1949
- 1949-04-05 US US85709A patent/US2575014A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2700057A (en) * | 1952-03-28 | 1955-01-18 | Du Pont | Process for preparing 2, 13-tetradecanedione from 1-methylcyclohexyl hydroperoxide |
| US2671810A (en) * | 1952-05-24 | 1954-03-09 | Du Pont | Long-chain diketones |
| US2822399A (en) * | 1953-05-01 | 1958-02-04 | Du Pont | Manufacture of diketones |
| US2798096A (en) * | 1954-02-17 | 1957-07-02 | Exxon Research Engineering Co | Production of cyclic hydroperoxides |
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