US2563050A - Treatment of olefins with liquid anhydrous hydrogen bromide - Google Patents
Treatment of olefins with liquid anhydrous hydrogen bromide Download PDFInfo
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- US2563050A US2563050A US607906A US60790645A US2563050A US 2563050 A US2563050 A US 2563050A US 607906 A US607906 A US 607906A US 60790645 A US60790645 A US 60790645A US 2563050 A US2563050 A US 2563050A
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- United States
- Prior art keywords
- hydrogen bromide
- olefins
- bromide
- liquid hydrogen
- hydrocarbons
- Prior art date
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 title claims description 58
- 229910000042 hydrogen bromide Inorganic materials 0.000 title claims description 29
- 150000001336 alkenes Chemical class 0.000 title claims description 19
- 239000007788 liquid Substances 0.000 title description 24
- 238000000034 method Methods 0.000 claims description 23
- 150000001347 alkyl bromides Chemical class 0.000 claims description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 description 24
- 150000002430 hydrocarbons Chemical class 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- -1 aliphatic olefins Chemical class 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000078856 Prunus padus Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
-
- 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
- C07C2/70—Catalytic processes with acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/17—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with acids or sulfur oxides
-
- 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
- C07C2527/08—Halides
Definitions
- Thi invention relates to the treatment of olefinic hydrocarbons with anhydrous liquid hydrogen bromide. More particularly, it relates to the production of alkyl bromides from aliphatic olefins. It is also concerned with the manufacture of alkyl aromatic hydrocarbons by the interaction of an aromatic hydrocarbon and an olefin in the presence of hydrogen bromide.
- the present invention comprises in part a simple process for manufacturing alkyl bromides which can be easily adapted to commercial practice and which is characterized by high yields of the desired products and low yields of undesired products. This process involves the hydrobromination of olefins with liquid hydrogen bromide in the absence of solvents.
- alkyl aromatics such as ethyl benzene, cumene, cymene, etc.
- our invention consists of a process for producing valuable derivatives of oletinic hydrocarbons which comprises treating said olefins with anhydrous liquid hydrogen bromide.
- the present invention relates to a process for producing valuable derivatives of olefinic hydrocarbons which comprises treating said olefins with anhydrous liquid hydrogen bromide in the presence of an aromatic hydrocarbon.
- Olefins which may be treated in accordance with the present invention may be either normally gaseous or normally liquid and comprise ethylene, propylene, butylenes, amylenes, hexylenes and their higher homologues, including various polymers of normally gaseous olefins. These olefins may be obtained from any source and include products of catalytic and thermal cracking of oils and those obtained by dehydrogenating the corresponding paraffinic hydrocarbons or by dehydrating alcohols.
- Aromatic hydrocarbons such as benzene, toluene, other alkylated benzenes, naphthalene, alkylated naphthalenes, other poly-nuclear aromatics, etc, which are alkylated by olefinic hydrocarbons as hereinafter set forth may be obtained by the fractional distillation of petroleum, by the destructive distillation of coal, by the dehydrogenation and cyclization of aliphatic hydrocarbons and of alkylated aromatic hydrocarbons, and by other means.
- the present process may be carried out in batch or continuous type operation.
- anhydrous liquid hydrogen bromide is agitated within a mixer and the olefin is gradually introduced below the surface of the acid.
- the agitation may be stopped and the hydrocarbons separated and fractionated to recover the desired products.
- the hydrocarbon charge stock is fed to contactors in which intimate contact between the hydrocarbon and acid is maintained.
- the efliuent from the contactors is treated for the separation of the acid from the hydrocarbon, the acid being returned to the contactors and. the hydrocarbon being fed to the fractionation system.
- the hydrocarbon stream leaving the separator contains a small amount of dissolved hydrogen bromide, which may be removed by treatment with caustic, by fractionation, or by other suitable means. Hydrocarbons of high molecular weight and low hydrogen content graduall accumulate in the catalyst and should be removed by distillation or other suitable means in order to maintain the activity of the acid at the desired level.
- Example 1 86 mol percent of the butene charged was actually recovered as secondary butyl bromide in spite of inevitable losses. The higher boiling material contained bound bromide. It will be noted that this experiment was carried out in the presence of isobutane, which acted as a diluent. In Example 2, 74% of the propylene was converted to isopropyl bromide and 3.6% of the propylene charged was recovered as cumene. At room temperature, as shown in Example 3, 32% of the ethylene charged did not react. Of that which did react, 60% went to ethyl bromide and 16% to ethylbenzene. The experiment was repeated by adding the reactants and catalyst to the autoclave at room temperature and heating to 150 C. in Example 4. Under these conditions only 8% of the ethylene did not react. Of that which did react, 42% went to ethyl bromide, 21% to ethylbenzene, and 18% to diethylbenzene.
- mixtures of olefins and other hydrocarbons can be separated readily without the side reactions which characterize mose chemical methods of separation.
- a narrow boiling mixture of paraflins and oleflns are contacted with liquid hydrogen bromide and the oleflns are thereby converted to alkyl bromides.
- the hydrocarbons are separated from the acid and the bromides are recovered by fractionation or other suitable means.
- a process for producing valuable derivativ s oi olefinic hydrocarbons which comprises treating said olefins with a halide material consisting essentially of anhydrous liquid hydrogen bromide.
- a process for producing alkyl bromides which comprises reacting an olefin with anhydrous liquid hydrogen bromide.
- a process for producing alkyl bromides which comprises reacting a normally gaseous olefin with anhydrous liquid hydrogen bromide.
- a process for producing alkyl bromides which comprises reacting a normally liquid olefin with anhydrous liquid hydrogen bromide.
- a process tor the manufacture of ethyl bromide which comprises reacting ethylene with anhydrous liquid hydrogen bromide.
- a process for the manufacture of propyl bromide which comprises reacting propylene with anhydrous liquid hydrogen bromide.
- a process for producing alkylated aromatic hydrocarbons which comprises contacting an arcmatic hydrocarbon with an oleflnic hydrocarbon under alkylating conditions in the presence of a halide catalyst consisting essentially of anhydrous liquid hydrogen bromide.
- a process for producing ethylated benzene which comprises subjecting benzene to contact with ethylene under alkylating conditions in the presence of a halide catalyst consisting essentially of anhydrous liquid hydrogen bromide.
- a process for producing propylated benzene which comprises subjecting benzene to contact with propylene under alkylating conditions in the presence of a halide catalyst consisting essentially of anhydrous liquid hydrogen bromide.
- a process for the separation of oleflns from hydrocarbon mixtures containing oleflns which comprises treating said mixtures with anhydrous liquid hydrogen bromide, separating the hydrocarbon product from the acid layer, and recovering the alkyl bromides from said hydrocarbon product.
- a process for producing an alkyl bromide and an alkylated aromatic hydrocarbon which comprises subjecting a mixture of an olefin, an aromatic hydrocarbon and a halide catalyst consisting essentially of anhydrous hydrogen bromide to reaction at an alkylating temperature and under suflicient pressure to maintain the hydrogen bromide in liquid phase.
Description
Patented Aug. 7, 1951 TREATMENT OF OLEFINS WITH LIQUID ANHYDROUS HYDROGEN BROMIDE Carl B. Linn, Riverside, and Robert J. Newman, Lyons, Ill., assignors to Universal Oil Products Company, Chicago, Ill., a corporation oi Delaware No Drawing. Application July 30, 1945,
- Serial No. 607,906
12 Claims.
Thi invention relates to the treatment of olefinic hydrocarbons with anhydrous liquid hydrogen bromide. More particularly, it relates to the production of alkyl bromides from aliphatic olefins. It is also concerned with the manufacture of alkyl aromatic hydrocarbons by the interaction of an aromatic hydrocarbon and an olefin in the presence of hydrogen bromide.
All-:yl bromides have assumed considerable importance in recent years as starting materials for the production of a great many types of organic derivatives. Consequently, the need has arisen for an inexpensive method of preparing these compounds that can be adapted readily to large scale commercial operation. The present invention comprises in part a simple process for manufacturing alkyl bromides which can be easily adapted to commercial practice and which is characterized by high yields of the desired products and low yields of undesired products. This process involves the hydrobromination of olefins with liquid hydrogen bromide in the absence of solvents.
The large demand for alkyl aromatics, such as ethyl benzene, cumene, cymene, etc. is well known. It is another feature of our invention to provide a new method of producing these valuable alkyl aromatics.
In one embodiment our invention consists of a process for producing valuable derivatives of oletinic hydrocarbons which comprises treating said olefins with anhydrous liquid hydrogen bromide. In a more specific embodiment the present invention relates to a process for producing valuable derivatives of olefinic hydrocarbons which comprises treating said olefins with anhydrous liquid hydrogen bromide in the presence of an aromatic hydrocarbon.
Olefins which may be treated in accordance with the present invention may be either normally gaseous or normally liquid and comprise ethylene, propylene, butylenes, amylenes, hexylenes and their higher homologues, including various polymers of normally gaseous olefins. These olefins may be obtained from any source and include products of catalytic and thermal cracking of oils and those obtained by dehydrogenating the corresponding paraffinic hydrocarbons or by dehydrating alcohols.
Aromatic hydrocarbons such as benzene, toluene, other alkylated benzenes, naphthalene, alkylated naphthalenes, other poly-nuclear aromatics, etc, which are alkylated by olefinic hydrocarbons as hereinafter set forth may be obtained by the fractional distillation of petroleum, by the destructive distillation of coal, by the dehydrogenation and cyclization of aliphatic hydrocarbons and of alkylated aromatic hydrocarbons, and by other means.
The present process may be carried out in batch or continuous type operation. In the batch operation of this process anhydrous liquid hydrogen bromide is agitated within a mixer and the olefin is gradually introduced below the surface of the acid. After the olefin has been contacted with the hydrogen bromide for suitable length of time, the agitation may be stopped and the hydrocarbons separated and fractionated to recover the desired products. In the continuous type of operation, the hydrocarbon charge stock is fed to contactors in which intimate contact between the hydrocarbon and acid is maintained. The efliuent from the contactors is treated for the separation of the acid from the hydrocarbon, the acid being returned to the contactors and. the hydrocarbon being fed to the fractionation system. The hydrocarbon stream leaving the separator contains a small amount of dissolved hydrogen bromide, which may be removed by treatment with caustic, by fractionation, or by other suitable means. Hydrocarbons of high molecular weight and low hydrogen content graduall accumulate in the catalyst and should be removed by distillation or other suitable means in order to maintain the activity of the acid at the desired level.
The exact temperatures and pressures which should be employed will depend upon the activity and physical characteristics of the hydrocarbons involved. As a rule, excessive elevated temperatures are not necessary and good results are obtained below 200 C. Only suflicient pressure need be used to maintain the reactants in the liquid phase. Contact times of from about 1 to about 60 minutes are preferable.
The following examples are given to illustrate the character of the results obtained by the use of the present process, although the examples given are not introduced with the intention of unduly restricting the generally broad scope of the invention.
In Examples 1 and 2, the reactions were carried out in a steel turbomixer by charging a liquid hydrogen bromide was first added to the autoclave and then the hydrocarbon was added. Following the period of contacting, the contents were removed and the hydrocarbon product was caustic washed, dried, and analyzed. The op- 6 erating conditions and results of these runs are summarized in the following table.
Example No 1 2 3 4 I 10 Turbomixer Rotating Apparatus u Autoclave 0 Temperature, "C 1 15 Time, H0l11 l'S 3.0 4. 8 4 fm t l 165 150 360 400 15 Final 100 10 200 375 i'i gr 227 191 147 137 Isobutane 295 0 0 0 Normal Butan 90 0 0 0 Benzellie 3 4g 8g 33 2o Propy ene R Ethylerae... 0 0 22 26 eoovery, ram
Isobutane 300 Sec. But lBromide Higher B biling Point Material. Benzene Isopropyl Bromide Cumene Higher Boiling Point MateriaL.
Benzene .0 .8 Unreacted Ethylene 7.0 2.0 Ethyl Bromide. 35. 2 39. 4 Ethylbenzene... 8. 8 l8. 8 Diethylbenzene 2. 3 10. 5 Higher Boiling Point Material. 6. 5 30 1 Maximum.
In Example 1, 86 mol percent of the butene charged was actually recovered as secondary butyl bromide in spite of inevitable losses. The higher boiling material contained bound bromide. It will be noted that this experiment was carried out in the presence of isobutane, which acted as a diluent. In Example 2, 74% of the propylene was converted to isopropyl bromide and 3.6% of the propylene charged was recovered as cumene. At room temperature, as shown in Example 3, 32% of the ethylene charged did not react. Of that which did react, 60% went to ethyl bromide and 16% to ethylbenzene. The experiment was repeated by adding the reactants and catalyst to the autoclave at room temperature and heating to 150 C. in Example 4. Under these conditions only 8% of the ethylene did not react. Of that which did react, 42% went to ethyl bromide, 21% to ethylbenzene, and 18% to diethylbenzene.
The results of these experiments show that oleflns can be converted into alkyl bromides in excellent yields by treatment of said oleflns with 5 liquid hydrogen bromide. This is true for pure oleflns as well as for mixtures of oleflns with other hydrocarbons. The results also show that aromatic hydrocarbons can be alkylated with olefins in the presence of liquid hydrogen bromide.
In one modification of our invention, mixtures of olefins and other hydrocarbons, particularly mixtures of oleflns and parafllns, can be separated readily without the side reactions which characterize mose chemical methods of separation. As illustrated in Example 1, a narrow boiling mixture of paraflins and oleflns are contacted with liquid hydrogen bromide and the oleflns are thereby converted to alkyl bromides. The hydrocarbons are separated from the acid and the bromides are recovered by fractionation or other suitable means.
' We claim as our invention: 1. A process for producing valuable derivativ s oi olefinic hydrocarbons which comprises treating said olefins with a halide material consisting essentially of anhydrous liquid hydrogen bromide.
2. A process for producing alkyl bromides which comprises reacting an olefin with anhydrous liquid hydrogen bromide.
3. A process for producing alkyl bromides which comprises reacting a normally gaseous olefin with anhydrous liquid hydrogen bromide.
4. A process for producing alkyl bromides which comprises reacting a normally liquid olefin with anhydrous liquid hydrogen bromide.
5. A process tor the manufacture of ethyl bromide which comprises reacting ethylene with anhydrous liquid hydrogen bromide.
6. A process for the manufacture of propyl bromide which comprises reacting propylene with anhydrous liquid hydrogen bromide.
'7. A process for the manufacture of butyl bromide which comprises reacting butylene with anhydrous liquid hydrogen bromide.
8. A process for producing alkylated aromatic hydrocarbons which comprises contacting an arcmatic hydrocarbon with an oleflnic hydrocarbon under alkylating conditions in the presence of a halide catalyst consisting essentially of anhydrous liquid hydrogen bromide.
9. A process for producing ethylated benzene which comprises subjecting benzene to contact with ethylene under alkylating conditions in the presence of a halide catalyst consisting essentially of anhydrous liquid hydrogen bromide.
10. A process for producing propylated benzene which comprises subjecting benzene to contact with propylene under alkylating conditions in the presence of a halide catalyst consisting essentially of anhydrous liquid hydrogen bromide.
11. A process for the separation of oleflns from hydrocarbon mixtures containing oleflns which comprises treating said mixtures with anhydrous liquid hydrogen bromide, separating the hydrocarbon product from the acid layer, and recovering the alkyl bromides from said hydrocarbon product.
12. A process for producing an alkyl bromide and an alkylated aromatic hydrocarbon which comprises subjecting a mixture of an olefin, an aromatic hydrocarbon and a halide catalyst consisting essentially of anhydrous hydrogen bromide to reaction at an alkylating temperature and under suflicient pressure to maintain the hydrogen bromide in liquid phase.
CARL B. LINN. ROBERT J. NEWMAN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,058,465 Kharash Oct. 27, 1936 2,406,869 Upham Sept. 3, 1946 OTHER REFERENCES Simons et al.: Hydrogen Chloride as a Condensing Agent, J. A. C. 8., vol. 66, pages 1309-12 (August 1944) (4 pages).
International Critical Tables, vol. 3, page 228.
Kirschbaum: Distillation and Rectification, pages 8 to 10 (1948). (German edition published prior to 1943).
Claims (1)
12. A PROCESS FOR PRODUCING AN ALKYL BROMIDE AND AN ALKYLATED AROMATIC HYDROCARBON WHICH COMPRISES SUBJECTING A MIXTURE OF AN OLEFIN, AN AROMATIC HYDROCARBON AND A HALIDE CATALYST CONSISTING ESSENTIALLY OF ANHYDROUS HYDROGEN BROMIDE TO REACTION AT AN ALKYLATING TEMPERATURE AND UNDER SUFFICIENT PRESSURE TO MAINTAIN THE HYDROGEN BROMIDE IN LIQUID PHASE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US607906A US2563050A (en) | 1945-07-30 | 1945-07-30 | Treatment of olefins with liquid anhydrous hydrogen bromide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US607906A US2563050A (en) | 1945-07-30 | 1945-07-30 | Treatment of olefins with liquid anhydrous hydrogen bromide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2563050A true US2563050A (en) | 1951-08-07 |
Family
ID=24434199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US607906A Expired - Lifetime US2563050A (en) | 1945-07-30 | 1945-07-30 | Treatment of olefins with liquid anhydrous hydrogen bromide |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2563050A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2979540A (en) * | 1958-04-07 | 1961-04-11 | Dow Chemical Co | Process for the preparation of aliphatic bromides |
| US3277204A (en) * | 1963-12-02 | 1966-10-04 | Chevron Res | Halogenation and dehydrochlorination of straight chain alkanes using an aromatic diluent |
| US3305598A (en) * | 1962-07-27 | 1967-02-21 | Monsanto Co | Thermal polymerization in the presence of a halogen |
| US3624171A (en) * | 1967-05-16 | 1971-11-30 | Chevron Res | Process for the production of 1,8-dibromooctane |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2058465A (en) * | 1933-12-16 | 1936-10-27 | Du Pont | A process of adding a hydrogen halide to a compound containing an olefinic linkage |
| US2406869A (en) * | 1942-08-18 | 1946-09-03 | Phillips Petroleum Co | Catalyst preparation |
-
1945
- 1945-07-30 US US607906A patent/US2563050A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2058465A (en) * | 1933-12-16 | 1936-10-27 | Du Pont | A process of adding a hydrogen halide to a compound containing an olefinic linkage |
| US2406869A (en) * | 1942-08-18 | 1946-09-03 | Phillips Petroleum Co | Catalyst preparation |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2979540A (en) * | 1958-04-07 | 1961-04-11 | Dow Chemical Co | Process for the preparation of aliphatic bromides |
| US3305598A (en) * | 1962-07-27 | 1967-02-21 | Monsanto Co | Thermal polymerization in the presence of a halogen |
| US3277204A (en) * | 1963-12-02 | 1966-10-04 | Chevron Res | Halogenation and dehydrochlorination of straight chain alkanes using an aromatic diluent |
| US3624171A (en) * | 1967-05-16 | 1971-11-30 | Chevron Res | Process for the production of 1,8-dibromooctane |
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