# US 4,397,655 A · Novel process for preparing diesel fuel > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,397,655 A - Document ID: US4397655A - Status: Granted - Kind: A - Application number: 06/267,199 - Filed: 1981-05-26 - Granted: 1983-08-09 - Earliest claimed: 1981-05-26 - Assignees: Texaco Inc. - Inventors: William M. Sweeney - Web page: https://patentgrep.com/patent/US4397655A ## CPC - C10L 1/02: essentially based on components consisting of carbon, hydrogen, and oxygen only - F02B 3/06: with compression ignition (compression ignition engines using air or gas for blowing fuel into compressed air in cylinder F02B13/02) - C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS - F02B: INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL (gas-turbine plants F02C; hot-gas or combustion-product positive-displacement engine plants F02G) ## Abstract A vegetable oil such as soy bean oil, extended by addition of ethanol, may be stabilized against phase separation or haziness in the event of water contamination at pH below 7 by addition thereto of additives such as 2,2-dimethoxy propane. ## Claims ### Claim 1 The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water which comprises mixing (i) said composition containing a vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil, and (ii) as an additive, a ketal or an acetal or an orthoester thereby forming a stabilized composition of increased water-tolerance which remains a single phase mixture at pH below 7 in the presence of water; and recovering said stabilized composition of increased water-tolerance. ### Claim 2 (depends on 1) The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water as claimed in claim 1 wherein said alcohol is ethanol. ### Claim 3 (depends on 1) The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water as claimed in claim 1 wherein said alcohol is isopropanol. ### Claim 4 (depends on 1) The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water as claimed in claim 1 wherein additive is a ketal. ### Claim 5 (depends on 1) The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water as claimed in claim 1 wherein said additive is an acetal. ### Claim 6 (depends on 1) The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water as claimed in claim 1 wherein said ketal is 2,2-dimethoxy propane. ### Claim 7 (depends on 1) The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water as claimed in claim 1 wherein said ketal or acetal or orthoester is present in amount of 1 v %-25 v % of said composition. ### Claim 8 (depends on 1) The method of stabilizing a composition as claimed in claim 1 wherein said vegetable oil is soy bean oil. ### Claim 9 (depends on 1) The method of stabilizing a composition as claimed in claim 1 wherein said vegetable oil is corn oil. ### Claim 10 (depends on 1) The method of stabilizing a composition as claimed in claim 1 wherein said vegetable oil is peanut oil. ### Claim 11 (depends on 1) The method of stabilizing a composition as claimed in claim 1 wherein said vegetable oil is cottonseed oil. ### Claim 12 The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water which comprises mixing at pH below 7 (i) said composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil, and (ii) as an additive a ketal or an acetal or an orthoester thereby forming a stabilized composition of increased water-tolerance; and recovering said stabilized composition of increased water-tolerance which remains a single phase mixture at pH below 7 in the presence of water. ### Claim 13 (depends on 12) The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water as claimed in claim 12 wherein mixing is effected in the presence of acid. ### Claim 14 (depends on 12) The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water as claimed in claim 12 wherein mixing is effected in the presence of sulfuric acid. ### Claim 15 The method of stabilizing a composition containing an ethanol-miscible vegetable oil and ethanol or isopropanol or n-propanol whereby said composition is inhibited from separating into more than one layer on standing which comprises mixing at pH below 7, (i) said composition containing an ethanol-miscible vegetable oil and ethanol or isopropanol or n-propanol and (ii) as an additive a ketal or an acetal or an orthoester in amount of 1 v %-25 v % of said composition thereby forming a stabilized composition of increased water-tolerance; and recovering said stabilized composition of increased water-tolerance which remains a single phase mixture at pH below 7 in the presence of water. ### Claim 16 The method of stabilizing a composition containing an ethanol-miscible vegetable oil, water, and a water-miscible alcohol which is miscible with said vegetable whereby said composition is inhibited from separating into more than one layer on standing which comprises mixing at pH below 7 (i) said composition containing an ethanol-miscible vegetable oil, water and a water-miscible alcohol which is miscible with said vegetable oil, and (ii) as additive a ketal, acetal or orthoester whereby said water is reacted with said ketal or acetal or orthoester thereby forming a stabilized composition of increased water-tolerance; and recovering said stabilized composition of increased water-tolerance. ### Claim 17 (depends on 16) The method of stabilizing a composition containing an ethanol-miscible vegetable oil, water, and a water-miscible alcohol which is miscible in the said vegetable oil whereby said composition is inhibited from separating into more than one layer on standing as claimed in claim 16 wherein said ethanol-miscible vegetable oil is soy bean oil. ### Claim 18 (depends on 16) The method of stabilizing a composition containing an ethanol-miscible vegetable oil, water, and a water-miscible alcohol which is miscible in the said vegetable oil whereby said composition is inhibited from separating into more than one layer on standing as claimed in claim 16 wherein said alcohol is methanol or isopropanol or n-propanol. ### Claim 19 (depends on 16) The method of stabilizing a composition containing an ethanol-miscible vegetable oil, water, and a water-miscible alcohol which is miscible in the said vegetable oil whereby said composition is inhibited from separating into more than one layer on standing as claimed in claim 16 wherein said ketal is 2,2-dimethoxy propane. ### Claim 20 The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil, and water whereby said composition is maintained in a single phase which comprises mixing (i) said composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil, and water, (ii) as an additive a ketal, acetal, or an orthoester, and (iii) a catalytic amount, sufficient to maintain the pH below 7 of an acid thereby forming a single phase stabilized composition. ### Claim 21 (depends on 20) The method claimed in claim 20 wherein said additive is present in amount at least equivalent to the water present in said composition. ### Claim 22 The method of forming vegetable oil composition characterized by its ability to remain a single phase which comprises mixing (i) an ethanol-miscible vegetable oil, (ii) an aqueous solution of a water-miscible alcohol which is miscible with vegetable oil, and (iii) a ketal, an acetal, or an orthoester which reacts at pH below 7 with water which is present thereby forming a composition characterized by presence of a single phase; and recovering said single phase vegetable oil composition. ### Claim 23 (depends on 22) The method of forming a vegetable composition as claimed in claim 22 wherein said aqueous solution of a water-miscible alcohol is 95% ethanol. ### Claim 24 (depends on 22) The method of forming a vegetable oil composition as claimed in claim 22 wherein said pH is maintained by addition of acid. ### Claim 25 The method of stabilizing a composition containing an ethanol-miscible vegetable oil, water, and ethanol or isopropanol or n-propanol whereby said composition is inhibited from separating into more than one layer on standing which comprises mixing at pH below 7 (i) said composition containing an ethanol-miscible vegetable oil, water and ethanol or isopropanol or n-propanol; and (ii) 2,2-dimethoxy propane whereby said water is reacted with said 2,2-dimethoxy propane thereby forming a stabilized composition of increased water-tolerance; and recovering said stabilized composition of increased water-tolerance. ### Claim 26 A novel composition inhibited from separating into more than one layer on contact with water at pH below 7 which comprises 100 parts of an ethanol-miscible vegetable oil, 1-15 parts of a water-miscible alcohol which is miscible with said vegetable oil, and as additive 1-25 v % of a ketal, acetal, or an orthoester. ### Claim 27 (depends on 26) A novel composition as claimed in claim 26 wherein said vegetable oil is soy bean oil. ### Claim 28 (depends on 26) A novel composition as claimed in claim 26 wherein said alcohol is methanol or isopropanol or n-propanol. ### Claim 29 (depends on 26) A novel composition as claimed in claim 26 wherein said ketal is 2,2-dimethoxy propane. ### Claim 30 (depends on 26) A novel composition as claimed in claim 26 wherein said additive is an acetal. ### Claim 31 (depends on 26) A novel composition as claimed in claim 26 wherein said additive is an orthoester. ### Claim 32 A novel composition containing soy bean oil, ethanol or methanol, and 2,2-dimethoxy propane. ### Claim 33 A novel composition comprising 100 parts of an ethanol-miscible vegetable oil, 1-15 parts of a water-miscible alcohol which is miscible with said vegetable oil, and at least one reaction product of water and a ketal or an acetal or an orthoester. ### Claim 34 The method of stabilizing a composition containing an ethanol-miscible vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil whereby said composition is inhibited from separating into more than one layer on contact with water which comprises mixing (i) said composition containing a vegetable oil and a water-miscible alcohol which is miscible with said vegetable oil, and (ii) as an additive or orthoester thereby forming a stabilized composition of increased water-tolerance which remains a single phase mixture at pH below 7 in the presence of water; and recovering said stabilized composition of increased water-tolerance. ### Claim 35 A novel composition inhibited from separating into more than one layer on contact with water at pH below 7 which comprises 100 parts of an ethanol-miscible vegetable oil, 1-15 parts of a water-miscible alcohol which is miscible with said vegetable oil, and as additive 1-25 v % of an orthoester.