US2465475A - Purification of cyclic olefinic ketones - Google Patents
Purification of cyclic olefinic ketones Download PDFInfo
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- US2465475A US2465475A US609324A US60932445A US2465475A US 2465475 A US2465475 A US 2465475A US 609324 A US609324 A US 609324A US 60932445 A US60932445 A US 60932445A US 2465475 A US2465475 A US 2465475A
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- isophorone
- ketone
- acetone
- phorone
- ketones
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- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
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- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
Definitions
- This invention relates to an improved process for purifying cyclic olefinic ketones, particularly when the latter are present in admixture with products formed incidental to the preparation of said cyclic ketone.
- An object of this invention is an improved process for separating a cyclic olefinic ketone from a mixture consisting of an aliphatic olefinic ketone and a cyclic olefinic ketone.
- Another object of this invention is an improved process for removing aliphatic olefinic ketones from a mixture of alkyl ketone condensation products including aliphatic olefinic ketones and cyclic ketones.
- a further object of this invention is to provide an improved process for separating mesityl oxide and phorone from isophorone present in a mixture of condensation products of acetone.
- One specific embodiment of the present invention relates to a process for separating cyclic olefinic ketones from aliphatic olefinic ketones which comprises treating a mixture of said cyclic and aliphatic olefinic ketones with an aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. to convert aliphatic olefinic ketones into alkyl ketone, and separating said alkyl ketone from unconverted cyclic olefinic ketone.
- Another embodiment of this invention relates to a process which comprises condensing an alkyl ketone to form a reaction mixture comprising essentially a cyclic olefinic ketone and an allphatic olefinic ketone, treating said reaction mixture with an aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. to convert said aliphatic olefinic ketone into alkyl ketone, separating said alkyl ketone from unconverted cyclic olefinic ketone, and recycling said alkyl ketone to further condensation treatment.
- a further embodiment of this invention relates to a promss for treating a mixture of condensation products of an alkyl ketone with an aqueous solution 01 an acid-acting salt at a temperature of from about 100 to about 350 C. to convert aliphatic olefinic condensation products of alkyl ketones into alkyl ketone, and separating said alkyl ketone from unconverted cyclic, mono-olefinicketone condensation products of said alkyl ketone.
- Acetone may be condensed and cyclized to isophorone by several known methods, but in most of the cases a number of by-products are also formed including unsaturated aliphatic ketones such as mesityl oxide and phorone, Accordingly, when isophorone is the desired reaction product, the yield of this desired material is decreased by the appearance of the mentioned by-products.
- unsaturated aliphatic ketones such as mesityl oxide and phorone
- mesityl oxide and phorone are converted into acetone by treatment at an elevated temperature in the presence of a relatively large volume of a dilute aqueous solution of an acid-acting salt, While isophorone remains substantially unchanged during this treatment and is recoverable from the reaction mixture in relatively high purity.
- An alkyl ketone which is convertible into a homologue of isophorone has at least one hydrogen atom combined chemically with the carbon atom adjacent to the carbonyl carbon atom, while the other carbon atom adjacent to the carbonyl carbon atom is combined chemically to at least two hydrogen atoms.
- homologues of isophorone are formed by the condensation of such ketonic compounds including methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, diethyl ketone, ethyl propyl ketone, ethyl iso-
- a catalyst comprising essentially an aqueous solution of an acid-acting salt.
- Suitable catalytic materials include particularly aqueous solutions of magnesium chloride, aluminum chloride, iron chloride, nickel chloride, ammonium chloride, and the corresponding bromides and sulfates,
- concentration of the acid-acting salt is generally from about 0.05 to about 10% by vention relates to a process which comprises weight of the total aqueous solution.
- the catalysts preferred for our process comprise aqueous solutions of acid-acting salts of such concentrations that the solutions have a pH value of less than about 6.
- the volume of solution used relative to the ketone condensation product undergoing treatment should be such that water is present in more than 200% of the theoretical quantity necessary for conversion of the unsaturated dimers of the alkyl ketones into said alkyl ketones.
- the temperature of the reaction mixture should be from about 100 to about 350 C. but is preferably from about 150 to about 250 C. It is also desirable to carry out the process at a superatmospheric pressure to maintain in liquid phase a substantial proportion of the reactants and solution of hydrolyzable salt.
- the process is carried out by commingling a mixture of the alkyl ketone condensation products with one or more volumes of an aqueous solution of an aicd-acting salt at a temperature and for a time sufi'icient to convert aliphatic unsaturated ketonic condensation products of alkyl ketones into said alkyl ketones with substantially no influence upon the cyclic, mono-olefinic ketones present in said alkyl keto-ne condensation product,
- acetone condensation products comprising mesityl oxide, phorone, and isophorone are so treated, the mesityl oxide and phorone are converted into acetone which is dissolved in the aqueous solution and is readily separable from unconverted isophorone.
- the acetone present in said aqueous solution may then be recovered by suitable means and/or subjected to condensation reaction to produce additional quantities of isophorone.
- the organic material from which mesityl oxide and phorone were so separated and comprising essentially isophorone is then washed, dried, and distilled to give a frac-' tion comprising substantially pure isophorone.
- Example I 49 grams of mesityl oxide and 150 grams of an aqueous solution containing 2 to 3% by weight of ferric chloride were heated at 210 C. for 2.5 hours in a rotatable steel autoclave of 450 cc. capacity.
- the reaction product contained acetone but no mesityl oxide, showing that the mesityl oxide underwent conversion into acetone.
- Emample II In another run at the same temperature and operating conditions, 30 grams of phorone when treated with an aqueous solution containing 3% by weight of ferric chloride yielded 73% of acetone and 27% of unconverted phorone.
- Example III A mixture of acetone condensation pro-ducts consisting of of isophorone, 25% of phorone, and 65% of mesityl oxide upon treatment with 4 4 volumes of an aqueous solution containing 3% by weight of ferric chloride at 225 C. for 1 hour yields an organic liquid product comprising essentially isophorone.
- the aqueous solution of ferric chloride contains acetone in an amount
- Example V A mixture consisting of 40 grams of mesityl oxide, 15 grams of phorone and 25 grams of isophorone and 125 grams of an aqueous solution containing 3% by weight of ammonium chloride was heated at 260 C. for 2 hours in a rotatable steel autoclave of 450 cc. capacity. During this treatment about of the mesityl oxide and of the phorone were converted into acetone.
- a process for separating a cyclic olefinic ketone from a mixture containing said cyclic oler'inic ketone and an aliphatic olefinio ketone which comprises treating said mixture with an aqueous solution of an acid-acting salt at a temperature of from about to about 350 C. to convert the aliphatic olefinic ketone into alkyl keto-ne, and separating said alkyl ketone from unconverted cyclic olef nic ketone.
- a process which comprises treating a mixture of alkyl ketone condensation products comprising cyclic mono-oiefinic ketones and aliphatic olefinic ketones with an aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. to convert the aliphatic oleing said alkyl ketone and the unconverted cyclic, mono-oleiinic ketone.
- a process which comprises treating a mixture of alkyl lzetone condensation products comprising cyclic and aliphatic olefinic ketones with an aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. and at a superatmospheric pressure to convert the aliphatic olefinic ketones into an alkyl ketone, and separating said alkyl ketone and the unconverted cyclic, mono-olefinic ketone.
- a process which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone at a temperature of from about 100 to about 350 C. with a dilute aqueous solution of an acid-acting salt to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone.
- a process for preparing substantially pure isophorone which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone with a dilute aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. and at a pressure suflicient to maintain the reaction mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone.
- a process for preparing substantially pure 'isophorone which comprises treating a mixture of acetone condensation products including assumeyl oxide, phorone, and isophorone with a dilute aqueous solution of an acid-acting chloride salt at a temperature of from about 100 to about 350 C. and at a pressure sufiicient to maintain the reaction mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone.
- a process for preparing substantially pure isophorone which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone with an aqueous solution containing from about 0.05 to about 10% by weight of an acid-acting chloride salt at a temperature of from about 100 to about 350 C. and at a pressure sufficient to maintain the reaction mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone,
- a process for preparing substantially pure isophorone which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone with an aqueous solution containing from about 0.05 to about 10% by weight of ferric chloride at a temperature of from about 100 to about 350 C.
- a process for preparing substantially pure isophorone which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone with an aqueous solution containing from about 0.05 to about 10% by weight of ammonium chloride at a temperature of from about 100 to about 350 C. and at a pressure sufficient to maintain the reaction mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophone.
Description
Patented Mar. 29, 1949 UNITED STATES TENT OFFICE PURIFICATION OF CYCLIC OLEFINIC KETONES No Drawing. Application August 6, 1945, Serial No. 609,324
9 Claims. (Cl. 260-586) This application is a continuation-in-part of our co-pending application Serial No. 570,466, filed December 29, 1944, now abandoned.
This invention relates to an improved process for purifying cyclic olefinic ketones, particularly when the latter are present in admixture with products formed incidental to the preparation of said cyclic ketone.
An object of this invention is an improved process for separating a cyclic olefinic ketone from a mixture consisting of an aliphatic olefinic ketone and a cyclic olefinic ketone.
Another object of this invention is an improved process for removing aliphatic olefinic ketones from a mixture of alkyl ketone condensation products including aliphatic olefinic ketones and cyclic ketones.
A further object of this invention is to provide an improved process for separating mesityl oxide and phorone from isophorone present in a mixture of condensation products of acetone.
One specific embodiment of the present invention relates to a process for separating cyclic olefinic ketones from aliphatic olefinic ketones which comprises treating a mixture of said cyclic and aliphatic olefinic ketones with an aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. to convert aliphatic olefinic ketones into alkyl ketone, and separating said alkyl ketone from unconverted cyclic olefinic ketone.
Another embodiment of this invention relates to a process which comprises condensing an alkyl ketone to form a reaction mixture comprising essentially a cyclic olefinic ketone and an allphatic olefinic ketone, treating said reaction mixture with an aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. to convert said aliphatic olefinic ketone into alkyl ketone, separating said alkyl ketone from unconverted cyclic olefinic ketone, and recycling said alkyl ketone to further condensation treatment.
A further embodiment of this invention relates to a promss for treating a mixture of condensation products of an alkyl ketone with an aqueous solution 01 an acid-acting salt at a temperature of from about 100 to about 350 C. to convert aliphatic olefinic condensation products of alkyl ketones into alkyl ketone, and separating said alkyl ketone from unconverted cyclic, mono-olefinicketone condensation products of said alkyl ketone.
A still further embodiment of the present intreating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone at a temperature of from about 150 to about 350 C. with a dilute aqueous solution of an acid-acting salt whereby said mesityl oxide and phorone are converted into acetone, and separating said acetone from unconverted isophorone.
Acetone may be condensed and cyclized to isophorone by several known methods, but in most of the cases a number of by-products are also formed including unsaturated aliphatic ketones such as mesityl oxide and phorone, Accordingly, when isophorone is the desired reaction product, the yield of this desired material is decreased by the appearance of the mentioned by-products. These different by-products not only cause a loss but they are also sometimes troublesome to dispose of in large scale commercial operations,
We have observed that mesityl oxide and phorone are converted into acetone by treatment at an elevated temperature in the presence of a relatively large volume of a dilute aqueous solution of an acid-acting salt, While isophorone remains substantially unchanged during this treatment and is recoverable from the reaction mixture in relatively high purity.
While the process of our invention is particularly applicable to the purification of isophorone derived from acetone, this process is also utilizable in purifying homologues of isophorone such as are obtainable by condensation of certain other ketones. An alkyl ketone which is convertible into a homologue of isophorone has at least one hydrogen atom combined chemically with the carbon atom adjacent to the carbonyl carbon atom, while the other carbon atom adjacent to the carbonyl carbon atom is combined chemically to at least two hydrogen atoms. Thus, homologues of isophorone are formed by the condensation of such ketonic compounds including methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl isobutyl ketone, diethyl ketone, ethyl propyl ketone, ethyl iso- The process of this invention is effected in the presence of a catalyst comprising essentially an aqueous solution of an acid-acting salt. Suitable catalytic materials include particularly aqueous solutions of magnesium chloride, aluminum chloride, iron chloride, nickel chloride, ammonium chloride, and the corresponding bromides and sulfates, The concentration of the acid-acting salt is generally from about 0.05 to about 10% by vention relates to a process which comprises weight of the total aqueous solution. The catalysts preferred for our process comprise aqueous solutions of acid-acting salts of such concentrations that the solutions have a pH value of less than about 6. The volume of solution used relative to the ketone condensation product undergoing treatment should be such that water is present in more than 200% of the theoretical quantity necessary for conversion of the unsaturated dimers of the alkyl ketones into said alkyl ketones. The temperature of the reaction mixture should be from about 100 to about 350 C. but is preferably from about 150 to about 250 C. It is also desirable to carry out the process at a superatmospheric pressure to maintain in liquid phase a substantial proportion of the reactants and solution of hydrolyzable salt.
The process is carried out by commingling a mixture of the alkyl ketone condensation products with one or more volumes of an aqueous solution of an aicd-acting salt at a temperature and for a time sufi'icient to convert aliphatic unsaturated ketonic condensation products of alkyl ketones into said alkyl ketones with substantially no influence upon the cyclic, mono-olefinic ketones present in said alkyl keto-ne condensation product, Thus, when acetone condensation products comprising mesityl oxide, phorone, and isophorone are so treated, the mesityl oxide and phorone are converted into acetone which is dissolved in the aqueous solution and is readily separable from unconverted isophorone. The acetone present in said aqueous solution may then be recovered by suitable means and/or subjected to condensation reaction to produce additional quantities of isophorone. The organic material from which mesityl oxide and phorone were so separated and comprising essentially isophorone is then washed, dried, and distilled to give a frac-' tion comprising substantially pure isophorone.
The following examples are given to illustrate the character of results obtained by the process of our invention, although these data are not introduced with the intention of unduly restricting the broad scope of the invention.
Example I 49 grams of mesityl oxide and 150 grams of an aqueous solution containing 2 to 3% by weight of ferric chloride were heated at 210 C. for 2.5 hours in a rotatable steel autoclave of 450 cc. capacity. The reaction product contained acetone but no mesityl oxide, showing that the mesityl oxide underwent conversion into acetone.
Emample II In another run at the same temperature and operating conditions, 30 grams of phorone when treated with an aqueous solution containing 3% by weight of ferric chloride yielded 73% of acetone and 27% of unconverted phorone.
Example III Example IV A mixture of acetone condensation pro-ducts consisting of of isophorone, 25% of phorone, and 65% of mesityl oxide upon treatment with 4 4 volumes of an aqueous solution containing 3% by weight of ferric chloride at 225 C. for 1 hour yields an organic liquid product comprising essentially isophorone. The aqueous solution of ferric chloride contains acetone in an amount Example V A mixture consisting of 40 grams of mesityl oxide, 15 grams of phorone and 25 grams of isophorone and 125 grams of an aqueous solution containing 3% by weight of ammonium chloride was heated at 260 C. for 2 hours in a rotatable steel autoclave of 450 cc. capacity. During this treatment about of the mesityl oxide and of the phorone were converted into acetone.
The novelty and utility of the process of the present invention are evident from the preceding specification and examples, although neither section is introduced to limit unduly the generally broad scope of the invention.
We claim as our invention:
1. A process for separating a cyclic olefinic ketone from a mixture containing said cyclic oler'inic ketone and an aliphatic olefinio ketone which comprises treating said mixture with an aqueous solution of an acid-acting salt at a temperature of from about to about 350 C. to convert the aliphatic olefinic ketone into alkyl keto-ne, and separating said alkyl ketone from unconverted cyclic olef nic ketone.
2. A process which comprises treating a mixture of alkyl ketone condensation products comprising cyclic mono-oiefinic ketones and aliphatic olefinic ketones with an aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. to convert the aliphatic oleing said alkyl ketone and the unconverted cyclic, mono-oleiinic ketone.
3. A process which comprises treating a mixture of alkyl lzetone condensation products comprising cyclic and aliphatic olefinic ketones with an aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. and at a superatmospheric pressure to convert the aliphatic olefinic ketones into an alkyl ketone, and separating said alkyl ketone and the unconverted cyclic, mono-olefinic ketone.
4. A process which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone at a temperature of from about 100 to about 350 C. with a dilute aqueous solution of an acid-acting salt to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone.
5. A process for preparing substantially pure isophorone which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone with a dilute aqueous solution of an acid-acting salt at a temperature of from about 100 to about 350 C. and at a pressure suflicient to maintain the reaction mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone.
6. A process for preparing substantially pure 'isophorone which comprises treating a mixture of acetone condensation products including iesityl oxide, phorone, and isophorone with a dilute aqueous solution of an acid-acting chloride salt at a temperature of from about 100 to about 350 C. and at a pressure sufiicient to maintain the reaction mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone.
7. A process for preparing substantially pure isophorone which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone with an aqueous solution containing from about 0.05 to about 10% by weight of an acid-acting chloride salt at a temperature of from about 100 to about 350 C. and at a pressure sufficient to maintain the reaction mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone,
8. A process for preparing substantially pure isophorone which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone with an aqueous solution containing from about 0.05 to about 10% by weight of ferric chloride at a temperature of from about 100 to about 350 C.
and at a pressure sufficient to maintain the reac- 5 tion mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophorone. 9. A process for preparing substantially pure isophorone which comprises treating a mixture of acetone condensation products including mesityl oxide, phorone, and isophorone with an aqueous solution containing from about 0.05 to about 10% by weight of ammonium chloride at a temperature of from about 100 to about 350 C. and at a pressure sufficient to maintain the reaction mixture in liquid phase to convert said mesityl oxide and phorone into acetone, and separating said acetone and unconverted isophone.
HERMAN PINES. VLADIMIR N. IPATIEFF.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Name Date McAllister June 13, 1944 Number
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US609324A US2465475A (en) | 1945-08-06 | 1945-08-06 | Purification of cyclic olefinic ketones |
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| Application Number | Priority Date | Filing Date | Title |
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| US609324A US2465475A (en) | 1945-08-06 | 1945-08-06 | Purification of cyclic olefinic ketones |
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| US2465475A true US2465475A (en) | 1949-03-29 |
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| US609324A Expired - Lifetime US2465475A (en) | 1945-08-06 | 1945-08-06 | Purification of cyclic olefinic ketones |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2968677A (en) * | 1961-01-17 | Purification of isophorone |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2351352A (en) * | 1941-07-29 | 1944-06-13 | Shell Dev | Separation of by-products from isophorone |
-
1945
- 1945-08-06 US US609324A patent/US2465475A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2351352A (en) * | 1941-07-29 | 1944-06-13 | Shell Dev | Separation of by-products from isophorone |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2968677A (en) * | 1961-01-17 | Purification of isophorone |
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