Skip to main content
OSTI.GOVU.S. Department of Energy Office of Scientific and Technical Information
U.S. Department of Energy
Office of Scientific and Technical Information
 

Catalytic hydration of terminal alkenes to primary alcohols

Journal Article · · Science (Washington, D.C.); (United States)
;
Direct catalytic hydration of terminal alkenes to primary alcohols would be an inexpensive route to industrially useful alcohols and a convenient synthetic route for the synthesis of terminal alcohols in general. The reaction between trans-PtHCl(PMe/sub 3/)/sub 2/ (where Me = CH/sub 3/) and sodium hydroxide in a one-to-one mixture of water and 1-hexene yields a species that, at 60/sup 0/C and in the presence of the phase-transfer catalyst benzyltriethylammonium chloride, catalyzes selective hydration of 1-hexene to n-hexanol at a rate of 6.9 +/- 0.2 turnovers per hour. Hydration of 1-dodecene to n-dodecanol occurs at a rate of 8.3 +/- 0.4 turnovers per hour at 100/sup 0/C. Deuterium labeling experiments with trans-PtDCl(PMe/sub 3/)/sub 2/ show that hydration involves reductive elimination of a C-H bond. At low hydroxide concentrations (<8 equivalents), hydration of the water-soluble olefin 3-butene-1-ol to 1,4-butanediol exhibited a first-order dependence on hydroxide concentration for loss of catalytic activity. This suggest that hydroxide attacks the coordinated alkene slowly. At high hydroxide concentrations, the rate of catalysis was hydroxide-independent and first-order in alkene. Substitution of coordinated water (k/sub 1/ = 9.3 +/- 0.5 x 10/sup -3/ liters per mol per second) appears to be limiting under these conditions.
Research Organization:
Univ. of California at San Diego, La Jolla
OSTI ID:
6928205
Journal Information:
Science (Washington, D.C.); (United States), Journal Name: Science (Washington, D.C.); (United States) Vol. 233; ISSN SCIEA
Country of Publication:
United States
Language:
English

Similar Records

Synthesis and characterization of trans-(PMe/sub 3/)/sub 2/PtHCl and an investigation of its role in olefin hydration catalysis
Journal Article · Wed Sep 07 00:00:00 EDT 1988 · Inorg. Chem.; (United States) · OSTI ID:5783275
Enthalpies of hydration of alkenes. 1. The n-hexenes
Journal Article · Tue Nov 03 23:00:00 EST 1981 · J. Am. Chem. Soc.; (United States) · OSTI ID:5845569
Carbonyl products of the gas phase reaction of ozone with symmetrical alkenes
Journal Article · Sat Jun 01 00:00:00 EDT 1996 · Environmental Science and Technology · OSTI ID:263214

Related Subjects

090221* -- Alcohol Fuels-- Chemical Synthesis-- (1976-1989)
10 SYNTHETIC FUELS
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400202 -- Isotope Effects
Isotope Exchange
&amp; Isotope Separation
ALCOHOLS
ALKANES
ALKENES
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL PREPARATION
DEUTERIUM
HYDRATION
HYDROCARBONS
HYDROGEN ISOTOPES
HYDROXY COMPOUNDS
ISOTOPE EFFECTS
ISOTOPES
LIGHT NUCLEI
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANOMETALLIC COMPOUNDS
PLATINUM COMPOUNDS
SOLVATION
STABLE ISOTOPES
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS