Patent US4511745A successfully refreshed from Google Patents.
US4511745A
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Process for functionalizing alkanes
Assignee: Chevron USA Inc
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Filing: 1984-06-12
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Granted: 1985-04-16
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Expires: 2004-06-12
Abstract
Abstract Process for functionalizing saturated hydrocarbons selectively in the terminal position comprising: (a) reacting said saturated hydrocarbons of the formula: RH where: H represents a hydrogen atom, and R represents a saturated hydrocarbon radical, with a metal complex of the formula: CpRhPMe3H2 where: Cp represents a pentamethylated cyclopentadienyl radical, Rh represents a rhodium atom, P represents a phosphorous atom, Me represents a methyl group, H represents a hydrogen atom, in the presence of ultraviolet radiation at a temperature maintained at about -60 DEG to -17 DEG C. to form a hydridoalkyl complex of the formula: CpRhPMe3RH (b) reacting said hydridoalkyl complex with a haloform of the formula: CHX3 where: X represents a bromine, iodine or chlorine atom, at a temperature in the range of about -60 DEG to -17 DEG C. to form the corresponding haloalkyl complex of step (a) having the formula: CpRhPMe3RX; and, (c) reacting said haloalkyl complex formed in (b) with halogen (X2) at a temperature in the range of about -60 DEG to 25 DEG C. (i.e. ambient) to form a functional haloalkyl compound.
Inventors
- 👤 Robert G. Bergman
- 👤 Andrew H. Janowicz
- 👤 Roy A. Periana-Pillai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:54
CPC Classifications
C; C07; C07F; C07F15/00; C07F15/0006; C07F15/0073; C07C; C07C17/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
173 words
A process for functionalizing saturated hydrocarbons comprising: (a) reacting said saturated hydrocarbons of the formula: RH where: H represents a hydrogen atom, and R represents a saturated hydrocarbon radical, with a metal complex of the formula: CpRhPMe.sub.3 H.sub.2 where: Cp represents a pentamethylated cyclopentadienyl radical, Rh represents a rhodium atom, P represents a phosphorous atom, Me represents a methyl group, H represents a hydrogen atom, in the presence of ultraviolet radiation at a temperature maintained at about -60° to -17° C. to form a hydridoalkyl complex of the formula: CpRhPMe.sub.3 (R)(H) (b) reacting said hydridoalkyl complex with a haloform of the formula: CHX.sub.3 where: X represents a halogen atom selected from bromine, iodine and chlorine, at a temperature in the range of about -60° to -17° C. to form the corresponding haloalkyl complex of step (a) having the formula: CpRhPMe.sub.3 (R)(X); and, (c) reacting said haloalkyl complex formed in (b) with halogen at a temperature in the range of about -60° to 25° C. to form the alkyl halide of said saturated hydrocarbon.
Claim 2
Dependent Claim
173 words
A process for functionalizing saturated hydrocarbons comprising: (a) reacting said saturated hydrocarbons of the formula: RH where: H represents a hydrogen atom, and R represents a saturated hydrocarbon radical, with a metal complex of the formula: CpRhPMe.sub.3 H.sub.2 where: Cp represents a pentamethylated cyclopentadienyl radical, Rh represents a rhodium atom, P represents a phosphorous atom, Me represents a methyl group, H represents a hydrogen atom, in the presence of ultraviolet radiation at a temperature maintained at about -60° to -17° C. to form a hydridoalkyl complex of the formula: CpRhPMe.sub.3 (R)(H) (b) reacting said hydridoalkyl complex with a haloform of the formula: CHX.sub.3 where: X represents a halogen atom selected from bromine, iodine and chlorine, at a temperature in the range of about -60° to -17° C. to form the corresponding haloalkyl complex of step (a) having the formula: CpRhPMe.sub.3 (R)(X); and, (c) reacting said haloalkyl complex formed in (b) with halogen at a temperature in the range of about -60° to 25° C. to form the alkyl halide of said saturated hydrocarbon.
Claim 3
Dependent Claim
30 words
A process according to claim 1 wherein the temperatures are in the ranges as follows: (a) -35° to -20° C. (b) -35° to -20° C. (c) 0° to 20° C.
Claim 4
Dependent Claim
10 words
A process according to claim 1 wherein X is bromine.
Claim 5
Dependent Claim
28 words
A process according to claim 1 wherein the dilution of said metal complex in step (a) is in the range of about 1×10 -5 to 1×10 -2 .
Claim 6
Dependent Claim
15 words
A process according to claim 1 wherein excess saturated hydrocarbon reactant is employed as solvent.
Claim 7
Dependent Claim
29 words
A process according to claim 1 wherein R is at least one hydrocarbon radical of up to about 20 carbon atoms whereby RH is a liquid at reaction conditions.
Claim 8
Dependent Claim
13 words
A process according to claim 1 wherein R is an acyclic hydrocarbon radical.
Claim 9
Dependent Claim
16 words
A process according to claim 7 wherein said saturated hydrocarbon reactant has about 2-12 carbon atoms.
Claim 10
Dependent Claim
13 words
A process according to claim 1 wherein R is a cyclic hydrocarbon radical.
Claim 11
Dependent Claim
20 words
A process according to claim 1 wherein R is a liquid hydrocarbon radical of up to about 14 carbon atoms.
Claim 12
Dependent Claim
176 words
A process for functionalizing saturated hydrocarbons comprising: (a) reacting said saturated hydrocarbons of the formula: R.sub.1 H where: H represents a hydrogen atom, and R 1 represents a saturated hydrocarbon radical, with a metal complex of the formula: CpRhP(R.sub.2).sub.3 H.sub.2 where: Cp represents a pentamethylated cyclopentadienyl radical, Rh represents a rhodium atom, P represents a phosphorous atom, R 2 represents a hydrocarbon radical, H represents a hydrogen atom, in the presence of ultraviolet radiation at a temperature maintained at about -60° to -17° C. to form a hydridoalkyl complex of the formula: CpRhP(R.sub.2).sub.3 (R.sub.1)(H) (b) reacting said hydridoalkyl complex with a haloform of the formula: CHX.sub.3 where: X represents a halogen atom selected from bromine, iodine and chlorine, at a temperature in the range of about -60° to -17° C. to form the corresponding haloalkyl complex of step (a) having the formula: CpRhP(R.sub.2).sub.3 (R.sub.1)(X); and, (c) reacting said haloalkyl complex formed in (b) with halogen at a temperature in the range of about -60° to 25° C. to form the alkyl halide of said saturated hydrocarbon.
Claim 13
Dependent Claim
176 words
A process for functionalizing saturated hydrocarbons comprising: (a) reacting said saturated hydrocarbons of the formula: R.sub.1 H where: H represents a hydrogen atom, and R 1 represents a saturated hydrocarbon radical, with a metal complex of the formula: CpRhP(R.sub.2).sub.3 H.sub.2 where: Cp represents a pentamethylated cyclopentadienyl radical, Rh represents a rhodium atom, P represents a phosphorous atom, R 2 represents a hydrocarbon radical, H represents a hydrogen atom, in the presence of ultraviolet radiation at a temperature maintained at about -60° to -17° C. to form a hydridoalkyl complex of the formula: CpRhP(R.sub.2).sub.3 (R.sub.1)(H) (b) reacting said hydridoalkyl complex with a haloform of the formula: CHX.sub.3 where: X represents a halogen atom selected from bromine, iodine and chlorine, at a temperature in the range of about -60° to -17° C. to form the corresponding haloalkyl complex of step (a) having the formula: CpRhP(R.sub.2).sub.3 (R.sub.1)(X); and, (c) reacting said haloalkyl complex formed in (b) with halogen at a temperature in the range of about -60° to 25° C. to form the alkyl halide of said saturated hydrocarbon.
References Cited (Backward Citations)
US3459780A
Cited
US4138420A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-04-15 | 1988-10-15 | 1989-04-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-15 | 1992-10-15 | 1993-04-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-15 | 1996-10-15 | 1997-04-16 | $7700.00 | Window Closed / Lapsed |