US2302721A - Alkylation of aromatic compounds - Google Patents
Alkylation of aromatic compounds Download PDFInfo
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- US2302721A US2302721A US407223A US40722341A US2302721A US 2302721 A US2302721 A US 2302721A US 407223 A US407223 A US 407223A US 40722341 A US40722341 A US 40722341A US 2302721 A US2302721 A US 2302721A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/68—Catalytic processes with halides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
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- 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
Definitions
- This invention relates .to a process for the a treatment of aromatic compounds to produce higher molecular weight alkyl derivatives there- 01'. More specifically the process is concerned with a method of alkylating aromatic hydrocarbons by olefinic hydrocarbons in the presence of a particular type of catalyst to produce monoalkylated and poly-alkylated aromatic hydrocarbons.
- the present invention comprises a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact under alkylating conditions in the presence of a solution comprising essentially aluminum chloride dissoved in a chloronitroparafiin.
- Aromatic hydrocarbons such as benzene, toluene, other alkylated benzenes, naphthalene, alkylated naphthalenes, other poly-nuclear aromatics, etc., which are alkylated by oleflnic hydrocarbons as hereinafter set forth, may be obtained by the distillation of coal, by the dehydrogenation of naphthenic hydrocarbons, by the cyclization of aliphatic hydrocarbons, and by other means.
- Aliphatic olefinic hydrocarbons utilizable for all-:ylating aromatic hydrocarbons are either normally gaseous or normally liquid and comprise ethylene. propene, butenes, and higher, normally liquid homologs, the latter including various polymers of normally gaseous olefinic hydrocar- Diolefins, cyclic olefins, and other polyiolefins may also be made to react with aromatic hydrocarbons, but generally under different conditions of operation from those employed in the 'alkylation of aromatic hydrocarbons with noncyclic and branched-chain olefins.
- Aliphatic olefinic hydrocarbons utilizable in the present process are obtained from any source and comprise products of catalytic and thermal cracking of oils, those obtained by dehydrogenating the corresponding parafiinic hydrocarbons, by dehydrating alcohols, or by polymerization of normally gaseous olefinic hydrocarbons.
- Catalysts suitable for use in the process of the present invention comprise solutions of aluminum chloride in a chloronitroparaffin and particularly in a 1-chloro-1-nitroparafiin of which l-chloro-Lnitropropane is representative.
- the different chloronitroparafllns which may thus be employed for producing solutions containing aluminum chloride utilizable as catalysts in the present process are not necessarily equivalent in that some chloronitroparafiins are, for this purpose, more suitable than others.
- chloronitroparafiins Some of the chloronitroparafiins and a few of their physical properties are given in the following table for purposes of reference.
- Chloronitroparafflns utilizable in the process of this invention may have the chloro and nitro groups attached to the same carbon atom or to difierent carbon atoms.
- chlorination of a nitroparaflin in basic solution yields a l-chlorol-nitroparailin while chlorination of a very dry liquid nitroparafiin yields 1-chloro-2(or 3)- nitroparafiins.
- the different chloronitroparaflins are not necessarily equivalent in their suitability as solvents for aluminum chloride.
- Aluminum chloride dissolves readily in 1- chloro-l-nitropropane at about 20 C. yielding a clear orange-colored solution. However, if the solvent is kept at about 0 C. during the slow addition of substantially anhydrous aluminum chloride, 2. deep yellow-colored solution results which becomes orange-colored on warming to about 20 C.
- the chloronitroparaffin which has a relatively high dissolving power for aluminum chloride thus produces a solution which is generally miscible with an aromatic hydrocarbon as in the case of benzene, and the chloronitroparaffin may thus be said to serve as a solutizer for dispersing aluminum chloride in the aromatic hydrocarbon being subjected to alkylation.
- Aluminum chloride so dissolved or dispersed in a mixture of a chloronitroparafiin and an aromatic hydrocarbon is in intimate contact with the olefin added to said alkylation reaction mixture so that 1 molecular proportion of aluminum chloride can catalyze the alkylation of many molecular proportions of aromatic hydrocarbon.
- solutizing effect is observed when any other order of mixing is used for the aromatic hydrocarbon aluminum chloride, and ehloronitroparafhn.
- the particular chloronitroparafiin chosen as solutizer for aluminum chloride is also dependent upon the nature and proportions of the hydrocarbons being reacted, the conditions of operation, and other factors.
- the alkylation of an aromatic hydrocarbon by an olefinic hydrocarbon is preferably carried out in the presence of a solution of aluminum chloride in a chloronitroparafiin at a temperature of from about -25 to about 75 C. and under a pressure of from substantially atmospheric to approxi-' mately 100 atmospheres.
- the exact temperature employed in a given alkylation depends upon the properties of the aromatic and aliphatic hydrocarbons undergoing reaction.
- a higher molecular proportion of aromatic hydrocarbon to olefinic hydrocarbon is employed with a normally liquid olefin than with a normally gaseous olefin because of the fact that the higher molecular weight olefins, particularly those boiling higher than pentenes, generally undergo depolymerization prior to or simultaneously with'alkylation.
- 1 molecular proportion of di-isobutene reacts with 2 molecular prowhilean olefinic hydrocarbon or a hydrocarbon fraction containing olefinic hydrocarbons is added thereto preferably together with a relatively small amount of hydrogen chloride to effect formation of alkylated aromatic hydrocarbons of higher molecular weight than the aromatic hydrocarbon charged to the process.
- a process for producing alkylated aromatic compounds which comprises subjecting an arcmatic compound and an olefinic hydrocarbon to contact under alkylating conditions in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
- a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hyrocarbon and an olefinic hydrocarbon to contact under alkylating conditions in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
- a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact at a temperature of from about to about 75 C., in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
- a process for producing alkylated aromatic i hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact at a temperature of from about 25 C. to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
- a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon, an olefinic hydrocarbon,
- a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon, an olefinic hydrocarbon, and
- a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and a normally gaseous olefinic hydrocarbon to contact at a temperature of from about 25 toabout 75 Qunder a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparafiin.
- a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and a normally liquid olefinic hydrocarbon to contact at a temperature of from about 25 to about C. under a pressure of from substantially atmospheric to approximately atmospheres in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparafiin.
- a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact at a temperature of from about -25 to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of both aluminum chloride and a I-chIQro-Imitroparamn.
- a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact at a temperature of from about -25 to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of both aluminum chloride and l-chloro-l-nitropropane.
- a process forproducing alkylated benzenes which comprises subjecting benzene and an olefinic hydrocarbon to contact at a temperature of from about -25 to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of both aluminum chloride and a l-chloro-l-nitroparafiin.
- a process for producing alkylated benzenes which comprises subjecting benzene and an olefinic hydrocarbon to contact at a temperature
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Description
'[ bons.
Patented Nov. 24, 1942 ALKYLATION OF AROMATIC CODTPOUNDS Louis Schmerling. Chicago, Ill., assignor to Unlversal Oil Products Company, Chicago, 111., a corporation of Delaware No Drawing. Application August 16, 1941, Serial No. 407,223
14 Claims. (Cl. 260-671) This invention relates .to a process for the a treatment of aromatic compounds to produce higher molecular weight alkyl derivatives there- 01'. More specifically the process is concerned with a method of alkylating aromatic hydrocarbons by olefinic hydrocarbons in the presence of a particular type of catalyst to produce monoalkylated and poly-alkylated aromatic hydrocarbons.
In one specific embodiment the present invention comprises a process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact under alkylating conditions in the presence of a solution comprising essentially aluminum chloride dissoved in a chloronitroparafiin. v
Aromatic hydrocarbons, such as benzene, toluene, other alkylated benzenes, naphthalene, alkylated naphthalenes, other poly-nuclear aromatics, etc., which are alkylated by oleflnic hydrocarbons as hereinafter set forth, may be obtained by the distillation of coal, by the dehydrogenation of naphthenic hydrocarbons, by the cyclization of aliphatic hydrocarbons, and by other means.
Aliphatic olefinic hydrocarbons utilizable for all-:ylating aromatic hydrocarbons are either normally gaseous or normally liquid and comprise ethylene. propene, butenes, and higher, normally liquid homologs, the latter including various polymers of normally gaseous olefinic hydrocar- Diolefins, cyclic olefins, and other polyiolefins may also be made to react with aromatic hydrocarbons, but generally under different conditions of operation from those employed in the 'alkylation of aromatic hydrocarbons with noncyclic and branched-chain olefins. Aliphatic olefinic hydrocarbons utilizable in the present process are obtained from any source and comprise products of catalytic and thermal cracking of oils, those obtained by dehydrogenating the corresponding parafiinic hydrocarbons, by dehydrating alcohols, or by polymerization of normally gaseous olefinic hydrocarbons.
Catalysts suitable for use in the process of the present invention comprise solutions of aluminum chloride in a chloronitroparaffin and particularly in a 1-chloro-1-nitroparafiin of which l-chloro-Lnitropropane is representative. The different chloronitroparafllns which may thus be employed for producing solutions containing aluminum chloride utilizable as catalysts in the present process, are not necessarily equivalent in that some chloronitroparafiins are, for this purpose, more suitable than others.
Some of the chloronitroparafiins and a few of their physical properties are given in the following table for purposes of reference.
chlorom'tro- TabZe.Some propertzes of some paraflins Specific Chloronitroparaiiin B. P., "G gravity at C.
Chloronitromethane 122 l. 47 l-chloro-l-nitro-ethane.. 124 1. 25 2-chloro-l-nitro-ethane 173 l. 41 l-chloro-l-nitropropanei 143 1. 2-cl1loro-l-nitropropane 172 l. 24 3-chloro-l-nitropropane. 197 lv 26 z-chloroi-nitropropauel 133 l. 18 l-chloro-2-nitropropanc. 172 1.20 l-chloro-2-nitrobutane v 190 1. l6 1cblorol-nitro-2-methylpropane 151 l. 15 lchloro-Z-nitro-2-metbylpropane a. 181 l. 18
Chloronitroparafflns utilizable in the process of this invention may have the chloro and nitro groups attached to the same carbon atom or to difierent carbon atoms. Thus, chlorination of a nitroparaflin in basic solution yields a l-chlorol-nitroparailin while chlorination of a very dry liquid nitroparafiin yields 1-chloro-2(or 3)- nitroparafiins. The different chloronitroparaflins, however, are not necessarily equivalent in their suitability as solvents for aluminum chloride.
Aluminum chloride dissolves readily in 1- chloro-l-nitropropane at about 20 C. yielding a clear orange-colored solution. However, if the solvent is kept at about 0 C. during the slow addition of substantially anhydrous aluminum chloride, 2. deep yellow-colored solution results which becomes orange-colored on warming to about 20 C. The chloronitroparaffin which has a relatively high dissolving power for aluminum chloride thus produces a solution which is generally miscible with an aromatic hydrocarbon as in the case of benzene, and the chloronitroparaffin may thus be said to serve as a solutizer for dispersing aluminum chloride in the aromatic hydrocarbon being subjected to alkylation. Aluminum chloride so dissolved or dispersed in a mixture of a chloronitroparafiin and an aromatic hydrocarbon is in intimate contact with the olefin added to said alkylation reaction mixture so that 1 molecular proportion of aluminum chloride can catalyze the alkylation of many molecular proportions of aromatic hydrocarbon. Essentially the same, solutizing effect is observed when any other order of mixing is used for the aromatic hydrocarbon aluminum chloride, and ehloronitroparafhn. The particular chloronitroparafiin chosen as solutizer for aluminum chloride is also dependent upon the nature and proportions of the hydrocarbons being reacted, the conditions of operation, and other factors.
When aluminum chloride in the form of a solid is used as catalyst in the alkylation of aromatic hydrocarbons by olefinio hydrocarbons, the formation of sludge-like material upon the surface of the aluminum chloride used decreases its catalytic activity and ordinarily makes it necessary to withdraw the sludge-like material and to add fresh aluminum chloride in order to proceed with the alkylation. However, when alkylating with aluminum chloride dissolved in a chloronitroparafiin, such as a l-chloro-l-nitroparaflin, the catalyst is substantially in the form of a solution which is contacted readily with the reactingaromatic hydrocarbons and olefins. Thus, a relatively high speed of alkylation is obtained with a small quantity of aluminum chloride because substantially all of the aluminum chloride so in troduced into the reaction mixture, is available for catalyzing the reaction, a condition entirely difierent from that which exists with solid aluminum chloride catalyst as then only the aluminum chloride on the surface of the particles can be contacted with the reacting hydrocarbons.
In accordance with the present invention, the alkylation of an aromatic hydrocarbon by an olefinic hydrocarbon is preferably carried out in the presence of a solution of aluminum chloride in a chloronitroparafiin at a temperature of from about -25 to about 75 C. and under a pressure of from substantially atmospheric to approxi-' mately 100 atmospheres. The exact temperature employed in a given alkylation depends upon the properties of the aromatic and aliphatic hydrocarbons undergoing reaction. In order to ob tain relatively high yields of most alkylated aromatic hydrocarbons, it is desirable to have present from about 1 to about 40 molecular proporw tions of aromatic hydrocarbon to 1 molecular proportion of olefinic hydrocarbon.
In general a higher molecular proportion of aromatic hydrocarbon to olefinic hydrocarbon is employed with a normally liquid olefin than with a normally gaseous olefin because of the fact that the higher molecular weight olefins, particularly those boiling higher than pentenes, generally undergo depolymerization prior to or simultaneously with'alkylation. Thus 1 molecular proportion of di-isobutene reacts with 2 molecular prowhilean olefinic hydrocarbon or a hydrocarbon fraction containing olefinic hydrocarbons is added thereto preferably together with a relatively small amount of hydrogen chloride to effect formation of alkylated aromatic hydrocarbons of higher molecular weight than the aromatic hydrocarbon charged to the process. Only as much aluminum chloride-chloronitroparafiin solution is .added as is required for catalyzing the alkylation at a desired rate, and the alkylation may thus be catalyzed by the use of a relatively small quantity of aluminum chloride.
Alkylation products obtained as hereinabove' scribed.
substantially non-reactive liquid solvent.
pressure employed in such a continuous alkylaportions of benzene to produce 2 molecular proportions of tertiary butyl benzene. To assist in catalyzing the alkylation reaction from about 0.05 to about 5% by weight of hydrogen chloride may be added to the mixture of aromatic and olefinic hydrocarbons being subjected to contact with the solution of aluminum chloride in a chloronitroparaffin. It may also be desirable to have hydrogen present in a quantity of not more than about 10 mole per cent of the total aromatic and aliphatic hydrocarbons charged.
In effecting reaction between aromatic hydrocarbons and an alkylating agent as an olefinic or an olefin-producing substance according to the process of the present invention, the exact method of procedure varies with the nature and proportions of the reacting constituents. A simple procedure utilizable in the case of an aromatic hydrocarbon which is normally liquid (or if solid is readily soluble or dispersable in a chloronitroparaffin or other substantially inert liquid) and a normally gaseous or liquid olefinic hydrocarbon consists in contacting the aromatic and olefinic hydrocarbons with a solution of aluminum chloride in a chloronitroparaiiin using either batch or continuous operations. Thus in batch type treatment a solution of aluminum chloride in a chloronitroparafiin is charged to a reactor containing aromatic hydrocarbon and the reaction mixture is then stirred or otherwise agitated tion treatment are within the indicated limits but the particular conditions employed in any given alkylation vary with the molecular weights and reactivities of the aromatic and olefinic hydrocarbons charged, the concentration and activity of the catalyst solution, and other factors.
It is generally advantageous to dilute the olefinic hydrocarbon with a portion of the aromatic hydrocarbon and to introduce the olefin-containing mixture at a plurality of points throughout the reaction zone rather than to commingle all of the olefinic hydrocarbon-containing fraction with the aromatic hydrocarbon prior to their introduction to the catalytic alkylation zone. In
this way a relatively high ratio of aromatic hy-"= drocarbon to olefinic hydrocarbon is readily maintained, alkylation is thereby favored, and olefin polymerization is kept relatively low. The reaction mixture obtained from such a continuous treatment is then commingled with sufiicient water to decompose the remaining aluminum chloride, the liquid product is dried and distilled to separate unconverted aromatic hydrocarbon, alkylated aromatic hydrocarbons, and the chloronitroparaflln solvent. Unconverted and incompletely converted aromatic hydrocarbons and the recovered chloronitroparafiin solvent are recycled to further use in the process.
The following example is given to illustrate the character of results obtained by the use of the present process although the data presented are from a selected case and are not introduced with the intention of unduly restricting the generally broad scope of the invention.
' 5 parts by weight of aluminum chloride dissolved at 0 C. in 10 parts by weight of l-chlorol-nitropropane forming a yellow-colored solution which turned orange in color on warming to about C. and then became deep red upon addition of 80 parts by weight of benzene. The resulting red solution was placed in a reactor surrounded by a water bath and propane was passed therethrough at a relatively slow rate. The absorption of propene was kept at about 35 C. and during 4 hours 28.5 parts by weight or propene reacted and a reaction mixture was obtained consisting of an upper hydrocarbon layer and a heavier lower layer. The latter material, which amounted to 9 parts by weight, was a browncolored fluid which reacted vigorously with water. The hydrocarbon layer after washing with water and drying, amounted to 105.6 parts by weight (119 volumes) and was separated by distillation into the following fractions: unconverted benzene, 47 parts by weight; 1-chloro-1-nitropropane, 6 parts by weight; isopropyl benzene, 30
" parts by weight; fraction 163--204 C., 35 parts by weight; di-isopropyl benzene, 18 parts by weight; and higher boiling material, 13 parts by weight.
The nature ofthe present invention and its commercial utility can be seen from the speciflcation and example given, although neither section is intended to limit its generally broad scope.
I claim as my invention:
1. A process for producing alkylated aromatic compounds which comprises subjecting an arcmatic compound and an olefinic hydrocarbon to contact under alkylating conditions in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
2. A process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hyrocarbon and an olefinic hydrocarbon to contact under alkylating conditions in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
3. A process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact at a temperature of from about to about 75 C., in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
4. A process for producing alkylated aromatic i hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact at a temperature of from about 25 C. to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
5. A process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon, an olefinic hydrocarbon,
. and hydrogen chloride to contact at a temperature of from about -25 C. to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaffin.
6. A process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon, an olefinic hydrocarbon, and
hydrogen to contact at a temperature of from about 25 to about 75 C. under a pressure of pheric to approximately 100 atmospheres in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparaifin.
8. A process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and a normally gaseous olefinic hydrocarbon to contact at a temperature of from about 25 toabout 75 Qunder a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparafiin.
9. A process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and a normally liquid olefinic hydrocarbon to contact at a temperature of from about 25 to about C. under a pressure of from substantially atmospheric to approximately atmospheres in the presence of a catalyst comprising essentially aluminum chloride dissolved in a chloronitroparafiin.
10. A process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact at a temperature of from about -25 to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of both aluminum chloride and a I-chIQro-Imitroparamn.
11. A process for producing alkylated aromatic hydrocarbons which comprises subjecting an aromatic hydrocarbon and an olefinic hydrocarbon to contact at a temperature of from about -25 to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of both aluminum chloride and l-chloro-l-nitropropane.
12. A process forproducing alkylated benzenes which comprises subjecting benzene and an olefinic hydrocarbon to contact at a temperature of from about -25 to about 75 C. under a pressure of from substantially atmospheric to approximately 100 atmospheres in the presence of both aluminum chloride and a l-chloro-l-nitroparafiin.
13. A process for producing alkylated benzenes which comprises subjecting benzene and an olefinic hydrocarbon to contact at a temperature
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US407223A US2302721A (en) | 1941-08-16 | 1941-08-16 | Alkylation of aromatic compounds |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2511915A (en) * | 1950-06-20 | Production of chloronitro | ||
US2778862A (en) * | 1953-05-19 | 1957-01-22 | Union Carbide & Carbon Corp | Process for ethylating toluene |
US2947794A (en) * | 1957-07-01 | 1960-08-02 | American Cyanamid Co | 2, 2-di(p-tolyl) propane preparation |
US3398207A (en) * | 1966-12-01 | 1968-08-20 | Sun Oil Co | Selective isopropylation of pseudocumene |
-
1941
- 1941-08-16 US US407223A patent/US2302721A/en not_active Expired - Lifetime
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2511915A (en) * | 1950-06-20 | Production of chloronitro | ||
US2778862A (en) * | 1953-05-19 | 1957-01-22 | Union Carbide & Carbon Corp | Process for ethylating toluene |
US2947794A (en) * | 1957-07-01 | 1960-08-02 | American Cyanamid Co | 2, 2-di(p-tolyl) propane preparation |
US3398207A (en) * | 1966-12-01 | 1968-08-20 | Sun Oil Co | Selective isopropylation of pseudocumene |
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