Ammonium oleate
{{Chembox
| Name = Ammonium oleate
| ImageFile = Ammonium oleate.svg
| ImageSize =
| ImageAlt =
| IUPACName =
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 544-60-5
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChemSpiderID = 4940583
| DTXSID = DTXSID50878372
| EC_number = 208-873-1
| UNII =
| PubChem = 6435897
| InChI = InChI=1S/C18H34O2.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;/h9-10H,2-8,11-17H2,1H3,(H,19,20);1H3/b10-9-;
| InChIKey = WFXRJNDIBXZNJK-KVVVOXFISA-N
| SMILES = CCCCCCCCC=CCCCCCCCC(=O)O.N
}}
| Section2 = {{Chembox Properties
| N=1|H=37|O=2|C=18
| MolarMass =
| Appearance = brown solid
| Density = 0.903 g/cm3{{cite web |title=Ammonium oleate 100.008.067 {{!}} Density |url=https://chem.echa.europa.eu/100.008.067/dossier-view/fe2f3f17-e546-4f18-869a-be2fa0175c39/IUC5-b647f42d-d7a7-4eee-9399-c336391e7ca3_71a26254-70d1-4658-be94-13c2591aff8f |work=European Chemicals Agency}}
| MeltingPt = 71 °C (decomposes){{Cite web |title=CAS Common Chemistry {{!}} Ammonium oleate |work=Chemical Abstracts Service |access-date=8 March 2025 |url= https://commonchemistry.cas.org/detail?cas_rn=544-60-5 }}
| Solubility = soluble
}}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| GHS_ref =
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|362|403+233|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Ammonium oleate is a chemical compound with the chemical formula {{chem2|C17H33COONH4}}.{{cite book |last1=Staff |first1=ChemADVISOR Inc |title=Regulated Chemicals Directory 1994 |date=6 December 2012 |publisher=Springer Science & Business Media |isbn=978-94-011-0689-4 |page=126 |url=https://www.google.ru/books/edition/Regulated_Chemicals_Directory_1994/-bSr4omC0zwC?hl=en&gbpv=1&dq=Ammonium+oleate&pg=PA126&printsec=frontcover |access-date=9 March 2025 |language=en}}{{cite book |title=Technical Paper |date=1917 |publisher=U.S. Government Printing Office |page=20 |url=https://books.google.com/books?id=MsVTcvRwHEcC&dq=ammonium+oleate&pg=RA13-PA20 |access-date=6 March 2025 |language=en}}{{cite book |title=American Druggist and Pharmaceutical Record |date=1895 |publisher=American Druggist Publishing Company |page=271 |url=https://books.google.com/books?id=aynnAAAAMAAJ&dq=ammonium+oleate&pg=PA271 |access-date=6 March 2025 |language=en}} This is an organic ammonium salt of oleic acid.
Synthesis
Ammonium oleate is formed by the reaction between oleic acid and aqueous ammonia.{{cite book |last1=Allen |first1=Alfred Henry |title=Commercial Organic Analysis: pt. II. Hydrocarbons, petroleum and coal-tar products, asphalt, phenols and creosotes. 3d ed. with revisions and additions by the author and Henry Leffmann. 1900 |date=1899 |publisher=J. & A. Churchill |page=267 |url=https://www.google.ru/books/edition/Commercial_Organic_Analysis_pt_II_Hydroc/EAE4AQAAIAAJ?hl=en&gbpv=1&dq=Ammonium+oleate&pg=PA267&printsec=frontcover |access-date=9 March 2025 |language=en}}
Physical properties
Ammonium oleate emits toxic oxides of nitrogen when heated excessively. It is soluble in water.{{cite web |title=AMMONIUM OLEATE {{!}} CAMEO Chemicals {{!}} NOAA |url=https://cameochemicals.noaa.gov/chemical/8256 |publisher=cameochemicals.noaa.gov |access-date=6 March 2025}}
Uses
The compound is used in agriculture as a deer and rabbit repellent.{{cite book |last1=Dunn |first1=Kevin M. |title=Scientific Soapmaking: The Chemistry of the Cold Process |date=2010 |publisher=Clavicula Press |isbn=978-1-935652-09-0 |page=182 |url=https://books.google.com/books?id=DL0d6AoATfwC&dq=ammonium+oleate+soluble&pg=PA182 |access-date=6 March 2025 |language=en}}{{cite report |date=September 1992 |title=Pesticides - Fact Sheet for Soap Salts |url=https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_G-76_1-Sep-92.pdf |work=United States Environmental Protection Agency |access-date=8 March 2025 |id=EPA-738-F-92-013}}