U.S. flagAn official website of the United States government
                    Here's how you know **Official websites use .gov**
                            
                            A **.gov** website belongs to an official government organization in the United States.
 **Secure .gov websites use HTTPS**
                            
                            A **lock** (                            
                              A locked padlock                                                      
                            
                            ) or **https://** means you’ve safely connected to the .gov website. Share sensitive information only on official, secure websites.


Menu Agricultural Research Service
						
                    U.S. DEPARTMENT OF AGRICULTURE
 close



Research
                Research Home
                            National Programs
                            Research Projects
                            Scientific Manuscripts
                            International Engagement
                            Scientific Software/Models
                            Databases and Datasets
                            Office of Scientific Quality Review
            Media
                News & Features
                            Multimedia
                            Briefing Room
                            Down on the Farm
                            Press Room
                            Science in Your Shopping Cart
                            Scientific Discoveries
                            Tellus
                            Under the Microscope
            About ARS
                About ARS Home
                            Staff Directory
                            Labs and Research Centers (Map)
                            Headquarter Offices
                            Organizational Chart
                            Employee Services (REE Employees Only)
                            Office of Outreach, Diversity, and Equal Opportunity
            Work With Us
                Work With Us Home
                            ARS Vacancies at USAJOBS
                            Careers at ARS Information
                            Scientific Collaborations
                            Extramural Agreements
                            1890 Faculty Research Sabbatical ProgramSearch small
                    Search
            
            ARS Home
                                About ARS
                                Contact Us




ARS Home Research Publications at this Location





- ARS National Programs
- Search for a scientific manuscript
- Search for a research project
- ARS Software
- Programs and Projects
- Collaborations
- Subjects of Investigation
- Publications

Title:   Author  item
                                            Doll, Kenneth

                                                         - *Ken*item
                                            Erhan, Sevim
  Submitted to: Green Chemistry
                                    Publication Type: Peer Reviewed Journal
                                    Publication Acceptance Date: 4/9/2008
                                    Publication  Date: 6/3/2008
                                    Citation: Doll, K.M., Erhan, S.Z. 2008. Synthesis of cyclic acetals (ketals) from oleochemicals using a solvent free method. Green Chemistry. 10(6):712-717.Interpretive Summary: Despite the large growth in the bio-based fuel market, it is important not to neglect the development of new industrial products, such as lubrication fluids and surfactants.  Starting from two bio-based materials, methyl oleate, and levulinic acid, we are able to make a complimentary set of materials.  By changing the reaction conditions; we can favor the formation of either a branched ester, useful as a lubrication additive; or an acetal, useful as a controllable surfactant hydrophobe.  Our methods are atom efficient and do not use organic solvent, which makes them favorable in green chemistry terms.  This research benefits the vegetable oil industry by giving a new method where soybean oil can be turned into an industrial product with a potentially higher value, compared to the tumultuous fuel market.
                                Technical Abstract: We have studied the reaction selectivities of acid catalyzed ring opening reactions of epoxidized methyl oleate (methyl 9,10-epoxy stearate; EMO), to form either acetal or branched ester products.  We have produced:  methyl 9-(2-butyl-2-methyl-5-octyl-1,3-dioxolan-4-yl) nonanoate (hexanone methyl stearate acetal, HMSA), an oleochemically based acetal, in 83% isolated yield; from epoxidized methyl oleate and 2-hexanone.  Utilizing our reaction chemistry, we have also been able to demonstrate the relative selectivities in competitive experiments by reacting EMO with 2-pentanone and octanoic acid.  Finally, by controlling temperature and acid concentration, we were able to control the product distribution of the reaction of EMO with the bi-functional levulinic acid.  We could favor either the acetal, or branched ester product in this work.  This research may help lead to the formation of new hydrophobic molecules for the synthesis of new surfactants from oleochemicals.


Return to top


Connect with ARS Sign up


ARS Home
                            USDA.gov
                            Plain Writing
                            Policies & Links
                            Civil Rights Statements
                            FOIA
                            Accessibility Statement
                            Privacy Policy
                            Non-Discrimination Statement
                            Quality of Information
                            USA.gov
                            WhiteHouse.gov