IP Library › Granted Patent US 12,195,662
Granted Patent B2
US 12,195,662 · App. 17/970,938 · Granted Jan 14, 2025

Phytol-based surfactants and methods therefor

Inventors: Tao Dong (Lakewood, CO); Robert David Allen (Golden, CO); Lieve Laurens (Golden, CO)
Assignee: Alliance for Sustainable Energy, LLC
C09K23/32C09K23/28
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Quick Facts
Patent No.
US 12,195,662
App. No.
17/970,938
Granted
Jan 14, 2025
Kind
B2
Abstract

Described herein are compositions and methods for the conversion of chlorophyll-derived phytol into useful and economically viable surfactants. The provided compositions utilize the hydrophobic phytol structure and added functional groups to increase hydrophilicity at one end of the molecule.

Claims (26)

1. A surfactant having the formula:

wherein each of R 1 , R 2 and R 3 are each independently —OH or an ester having the formula —OOCR 4 ;

wherein R 4 is an alkylether selected from the range of C 1 -C 10 , a hydroxyamine selected from the range of C 1 -C 10 , a cyanocarboxylic acid selected from the range of C 1 -C 10 , an arylether or O bonded with R 1 , R 2 or R 3 to form an ethylene carbonate group or a dimer; and

wherein R 1 , R 2 and R 3 are not each —OH, and

wherein at least one of R 1 , R 2 or R 3 has the formula:

wherein the symbol is a covalent bond connected at R 1 , R 2 or R 3 in formula <FX1>.

2. The surfactant of claim 1 having the formula:

3. The surfactant of claim 1 having the formula:

4. The surfactant of claim 1 having the formula:

5. The surfactant of claim 1 having the formula:

6. A method comprising:

reacting phytantriol with dimethyl carbonate catalyzed by triazabicyclodecene in a carbonate solvent, thereby generating a carbonate surfactant.

7. The method of claim 6 wherein the carbonate surfactant has the formula:

wherein each of R 1 , R 2 and R 3 are each independently —OH or an ester having the formula —OOCR 4 ; and

wherein the symbol is a covalent bond connected at R 1 , R 2 or R 3 in formula <FX1>.

8. The method of claim 6 further comprising:

reacting the carbonate surfactant with an amine, thereby generating an amine surfactant.

9. The method of claim 8 , wherein the amine surfactant has the formula:

wherein each of R 1 , R 2 and R 3 are each independently —OH or an ester having the formula —OOCR 4 ;

wherein R 4 is an alkylether selected from the range of C 1 -C 10 , a hydroxyamine selected from the range of C 1 -C 10 , a cyanocarboxylic acid selected from the range of C 1 -C 10 , an arylether or O bonded with R 1 , R 2 or R 3 to form an ethylene carbonate group or a dimer; and

wherein R 1 , R 2 and R 3 are not each —OH.

10. The method of claim 6 further comprising:

reacting phytantriol, the carbonate surfactant with diphenyl carbonate to generate a phenyl surfactant.

11. The method of claim 6 further comprising:

epoxidizing phytol, thereby generating phytantriol.

12. A surfactant having the formula:

Assignments (3)
CHANGE OF NAME Recorded Dec 16, 2025
From: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
To: ALLIANCE FOR ENERGY INNOVATION, LLC
Reel/Frame 073993/0276 →
CONFIRMATORY LICENSE Recorded Jun 1, 2023
From: NATIONAL RENEWABLE ENERGY LABORATORY
To: UNITED STATES DEPARTMENT OF ENERGY
Reel/Frame 063829/0525 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2022
From: DONG, TAO; ALLEN, ROBERT DAVID; LAURENS, LIEVE
To: ALLIANCE FOR SUSTAINABLE ENERGY, LLC
Reel/Frame 061518/0011 →
Continuity (2)
Provisional Application 63270303 · Oct 21, 2021
Related Publication 20230128213A1 · Apr 27, 2023
References Cited (10)
US 20220041830A1 · Dong et al. · 2022 [cited by applicant]
JP 2002138061 · 2002 [cited by examiner]
Machine Translation of JP2002138061, 4 pages, retrieved 2023 (Year: 2023). [cited by examiner]
Akbar et al., “Phytantriol Based Smart Nano-Carriers for Drug Delivery Applications”, European Journal of Pharmaceutical Sciences, Apr. 2017, vol. 101, pp. 31-42. [cited by applicant]
Barauskas et al., “Phase Behavior of the Phytantriol/Water System”, Langmuir, Oct. 2003, vol. 19, No. 23, pp. 9562-9565. [cited by applicant]
Dannecker et al., “Facile and Sustainable Synthesisof Erythritol bis(carbonate), a Valuable Monomer for Non-Isocyanate Polyurethanes (NIPUs)”, Scientific Reports, 2019, vol. 9 No. 9858, pp. 1-6. [cited by applicant]
Guidi et al., “Thermal (Catalyst-Free) Transesterification of Diols and Glycerol with Dimethyl Carbonate: A Flexible Reaction for Batch and Continuous-Flow Applications”, ACS Sustainable Chemistry & Engineering, 2016, v… [cited by applicant]
McGinty et al., “Fragrance material review on phytol”, Food Chemical Toxicology, Jan. 2010, vol. 48, Supplement 3, pp. S59-S63. [cited by applicant]
Prabha et al., “Phytol—A biosurfactant from the aquatic weed Hydrilla verticillata”, Biocatalysis and Agricultural Biotechnology, 2019, vol. 17, pp. 736-742. [cited by applicant]
Rizwan et al., “Preparation of Phytantriol Cubosomes by Solvent Precursor Dilution for the Delivery of Protein Vaccines”, European Journal of Pharmaceutics and Biopharmaceutics, Sep. 2011, vol. 79, No. 1, pp. 15-22. [cited by applicant]