Granted Patent
B2
US 12,540,107 · App. 18/556,949 · Granted Feb 3, 2026
Selective photocatalytic reduction of alkynes to alkenes
Inventors:
Francesca Arcudi (Evanston, IL); Luka Dordevic (Evanston, IL); Emily A. Weiss (Evanston, IL); Samuel I. Stupp (Evanston, IL)
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Abstract
Disclosed herein are compositions and methods for the selective photocatalytic reduction of an alkyne compound to an alkene compound (e.g., acetylene to ethylene).
Claims (23)
1 . A method of synthesizing an alkene compound from an alkyne compound, comprising:
providing a first mixture comprising a cobalt(III) porphyrin compound, a photosensitizer, a reducing agent, and water;
adding an alkyne compound to the first mixture to form a reaction mixture; and
illuminating the reaction mixture with light.
2 . The method of claim 1 , wherein the cobalt(III) porphyrin compound is selected from [{meso-tetra(4-sulfonatophenyl)porphyrinato}cobalt(III)] and [{meso-tetra(4-carboxyphenyl)porphyrinato}cobalt(III)].
3 . The method of claim 2 , wherein the cobalt(III) porphyrin compound is [{meso-tetra(4-sulfonatophenyl)porphyrinato}cobalt(III)].
4 . The method of claim 1 , wherein the first mixture comprises the cobalt(III) porphyrin compound at a concentration of about 0.10 μM to about 50 μM.
5 . The method of claim 1 , wherein the photosensitizer is selected from tris(2,2′-bipyridyl)dichlororuthenium(II) and mesoporous graphitic carbon nitride.
6 . The method of claim 5 , wherein the photosensitizer is tris(2,2′-bipyridyl)dichlororuthenium(II).
7 . The method of claim 6 , wherein the first mixture comprises the tris(2,2′-bipyridyl)dichlororuthenium(II) photosensitizer at a concentration of about 50 μM to about 500 μM.
8 . The method of claim 5 , wherein the photosensitizer is mesoporous graphitic carbon nitride.
9 . The method of claim 8 , wherein the first mixture comprises about 2.5 mg of the mesoporous graphitic carbon nitride.
10 . The method of claim 1 , wherein the reducing agent is sodium ascorbate, or a mixture of sodium ascorbate and triethanolamine.
11 . The method of claim 1 , wherein the first mixture comprises the reducing agent at a concentration of about 0.01 M to about 0.50 M.
12 . The method of claim 1 , wherein the first mixture has a pH of about 8.0 to about 11.0.
13 . The method of claim 1 , wherein the alkyne compound is a C 2 -C 4 alkyne and the alkene compound is a C 2 -C 4 alkene.
14 . The method of claim 13 , wherein the alkyne compound is acetylene and the alkene compound is ethylene.
15 . The method of claim 13 , wherein the alkyne compound is propyne and the alkene compound is propylene.
16 . The method of claim 1 , wherein the light is selected from white light and blue light.
17 . The method of claim 1 , comprising illuminating the reaction mixture with visible light from a light-emitting diode.
18 . The method of claim 1 , wherein the first mixture is provided in a reaction vessel, and the step of adding the alkyne compound to the first mixture comprises adding the alkyne compound to the reaction vessel at a pressure of about 1 atm.
19 . The method of claim 1 , wherein the method is conducted at ambient temperature.
20 . A composition comprising a cobalt(III) porphyrin compound, a photosensitizer, a reducing agent, and water.
Assignments (2)
CONFIRMATORY LICENSE
Recorded Mar 4, 2024
From: NORTHWESTERN UNIVERSITY
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 066724/0192 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Nov 15, 2023
From: ARCUDI, FRANCESCA; DORDEVIC, LUKA; WEISS, EMILY A.; STUPP, SAMUEL I.
To: NORTHWESTERN UNIVERSITY
Reel/Frame 065571/0074 →
Continuity (3)
Provisional Application
63254395
· Oct 11, 2021
Provisional Application
63180798
· Apr 28, 2021
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