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Title: Process for alkane group dehydrogenation with organometallic catalyst

Patent ·
OSTI ID:871704
 [1];  [2]
  1. Goleta, CA
  2. Kailua, HI
+ Show Author Affiliations

An improved process is described for the catalytic dehydrogenation of organic molecules having a ##STR1## group to produce a ##STR2## group. The organic molecules are: ##STR3## wherein: A.sup.1, A.sup.2, A.sup.3, and A.sup.4 are each independently P, As or N: E.sup.2 is independently C or N; E.sup.3 is independently C, Si or Ge; E.sup.4 is independently C, Si, or Ge; and E.sup.5 is independently C, Si or Ge; M.sup.1, M.sup.2, M.sup.3, and M.sup.4 each is a metal atom independently selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum; Q.sup.1, Q.sup.2, Q.sup.3, and Q.sup.4 are each independently a direct bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, or CH.dbd.CH--; in structure I, structure II or structure IV, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each independently selected from alkyl, alkenyl, cycloalkyl, and aryl, or R.sup.1 and R.sup.2 together and R.sup.3 and R.sup.4 together form a ring structure having from 4 to 10 carbon atoms, or in structure III, R.sup.5, R.sup.6, R.sup.7, and R.sup.8 are each independently selected from alkyl, alkenyl, cycloalkyl, and aryl, or R.sup.5 and R.sup.6 together and R.sup.7 and R.sup.8 together form a ring structure having from 4 to 10 carbon atoms, at a temperature of between about 100.degree. and 250.degree. C. for between about 1 hr and 300 days in the absence of N.sub.2. The surprisingly stable catalyst is a complex of an organic ligand comprising H, C, Si, N, P atoms, and a platinum group metal. The dehydrogenation is performed between about 100 to 200.degree. C., and has increased turnover.

Research Organization:
Univ. of Hawaii, Honolulu, HI (United States)
DOE Contract Number:
FC36-94AL85804
Assignee:
Regents of University of California (Oakland, CA); University of Hawaii (Honolulu, HI)
Patent Number(s):
US 5780701
OSTI ID:
871704
Country of Publication:
United States
Language:
English

References (22)

Interaction of {2,6-bis[(di-tert-butylphosphino)methyl]phenyl}rhodium(I) with hydrocarbons. X-ray molecular structure of {2,6-bis[(di-tert-butylphosphino)methyl]phenyl}chlorohydridorhodium(III) journal October 1983
A highly active alkane dehydrogenation catalyst: stabilization of dihydrido rhodium and iridium complexes by a P–C–P pincer ligand journal January 1996
Thermocatalytic formation of molecular hydrogen and cyclo-octene from cyclo-octane by rhodium complexes journal January 1990
Efficient transfer-dehydrogenation of alkanes catalyzed by rhodium trimethylphosphine complexes under dihydrogen atmosphere journal November 1992
Synthesis and Reactivity of [IrH2(tBu2P)CH2CH2CHCH2CH2P(tBu2)], a Dynamic Iridium Polyhydride Complex journal October 1994
Thermocatalytic dehydrogenation of alkanes with Wilkinson complexes journal January 1993
Selective catalytic dehydrogenation of alkanes to alkenes journal December 1987
Efficiet and selective catalytic dehydrogeneation of alkanes using rhodium(I) arsine complexes journal January 1994
Photochemical dehydrogenation of alkanes catalyzed by trans-carbonylchlorobis(trimethylphosphine)rhodium: aspects of selectivity and mechanism journal August 1989
n-Alkene and dihydrogen formation from n-alkanes by photocatalysis using carbonyl(chloro)phosphine–rhodium complexes journal January 1988
Homogeneous tungsten, rhenium, and iridium catalysts in alkane dehydrogenation driven by reflux of substrate or of cosolvent or by inert-gas flow journal February 1993
The selective catalytic conversion of cycloalkanes into cycloalkenes using a soluble rhenium polyhydride system journal January 1983
Dehydrogenation of an alkane chain: rhodium(I) and iridium(I) complexes of 1,6-bis(diphenylphosphino)- trans-hex-3-ene journal April 1976
Activation of C-H bonds in saturated hydrocarbons. The catalytic functionalisation of cycloöctane by means of some soluble iridium and ruthenium polyhydride systems journal January 1984
Visible Light-Assisted Dehydrogenation of Alkanes Catalyzed by the RhCl(CH 2 =CH 2 )(PMe 3 ) 2 -hν System journal February 1991
The 1992 Alcan Award Lecture Excursions around the periodic table: ligand design in inorganic chemistry journal December 1992
Activation of C-H bonds in saturated hydrocarbons. The selective, catalytic functionalisation of methyl groups by means of a soluble iridium polyhydride system journal January 1985
Alkene and dihydrogen formation by catalytic dehydrogenation of alkane with RhCl(pr3)2 photogenerated from rhcl(co)(pr3)2 journal September 1989
Transfer-dehydrogenation of alkanes catalyzed by rhodium(I) phosphine complexes journal July 1996
Efficient low-temperature thermal functionalization of alkanes. Transfer dehydrogenation catalyzed by Rh(PMe3)2Cl(CO) in solution under a high-pressure hydrogen atmosphere journal August 1991
(Phosphinoalkyl)silanes. 3. 1 Poly( o -(diphenylphosphino)benzyl)silanes:  Synthesis, Spectroscopic Properties, and Complexation at Platinum or Iridium journal January 1996
Mechanism and Energetics for Dehydrogenation of Methane by Gaseous Iridium Ions journal May 1994

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Related Subjects

process
alkane
dehydrogenation
organometallic
catalyst
improved
described
catalytic
organic
molecules
str1
produce
str2
str3
independently
metal
atom
selected
consisting
ruthenium
rhodium
palladium
osmium
iridium
platinum
direct
bond
-ch
dbd
ch-
structure
ii
alkyl
alkenyl
cycloalkyl
aryl
form
10
carbon
atoms
iii
temperature
100
degree
250
300
days
absence
surprisingly
stable
complex
ligand
comprising
performed
200
increased
turnover
stable catalyst
organic molecules
metal atom
independently selected
improved process
carbon atoms
carbon atom
metallic catalyst
organic ligand
organometallic catalyst
organic molecule
ligand comprising
/585/999/