Saturated branched chain fatty acid production method

{
  "publication_number": "US10087132B2",
  "country": "US",
  "kind": "B2",
  "title": "Saturated branched chain fatty acid production method",
  "abstract": "Disclosed herein are processes for converting an unsaturated fatty acid into a saturated branched-chain fatty acid through a zeolite-catalyzed process and methods of economically regenerating and reusing the zeolite catalyst. The processes include subjecting the unsaturated fatty acid to an isomerization reaction to result in a selective conversion of the unsaturated fatty acid into the saturated branched-chain fatty acid. The reaction occurs in the presence of (i) an activated zeolite catalyst, (ii) an effective amount of water, and (iii) optionally an oligomerization reducing agent. The spent zeolite catalyst may be regenerated by heating to create a regenerated zeolite catalyst that is functional for use as the activated zeolite catalyst.",
  "claims": [
    "1. A process for converting an unsaturated fatty acid into a saturated branched-chain fatty acid and/or alkyl ester(s) thereof, the process comprising: (a) subjecting the unsaturated fatty acid to a skeletal isomerization reaction at a temperature from about 200° C. to 280° C. for a time range from about 4 to about 24 hours to result in a selective conversion of the unsaturated fatty acid into the saturated branched-chain fatty acid and/or alkyl ester(s) thereof, the skeletal isomerization reaction occurring in the presence of (i) an activated zeolite catalyst, wherein a zeolite catalyst is calcined at a temperature from about 400° C. to about 600° C. for about 1 hour to about 10 hours in a furnace to convert the zeolite catalyst into the activated zeolite catalyst, (ii) an effective amount of water or a lower alcohol to improve the selective conversion of the unsaturated fatty acid into the saturated branched-chain fatty acid and/or alkyl ester(s) thereof, and (iii) optionally an oligomerization reducing agent; (b) recovering an organic layer and subjecting the organic layer to a hydrogenation step to produce a product including the saturated branched-chain fatty acid; (c) recovering a spent zeolite catalyst; and (d) regenerating the spent zeolite catalyst by heating the spent zeolite to a temperature of about 120° C. to about 500° C. for a time of about 3 hours to about 5 hours to create a regenerated zeolite catalyst that is functional for use as the activated zeolite catalyst; wherein the zeolite catalyst is converted to the activated zeolite catalyst and the spent zeolite catalyst is converted to the regenerated zeolite catalyst without an acid treatment step.",
    "2. The process of claim 1, wherein the unsaturated fatty acid is an unsaturated linear chain fatty acid.",
    "3. The process of claim 1, wherein the unsaturated fatty acid has a carbon chain length from 12 to 30 carbon atoms.",
    "4. The process of claim 1, wherein the unsaturated fatty acid has a carbon chain length from 12 to 24 carbon atoms.",
    "5. The process of claim 1, wherein the unsaturated fatty acid has a carbon chain length from 16 to 20 carbon atoms.",
    "6. The process of claim 1, wherein the unsaturated fatty acid is an unsaturated linear chain fatty acid derived from a renewable source.",
    "7. The process of claim 1, wherein the unsaturated fatty acid is an unsaturated linear chain fatty acid derived from a renewable source selected from the group consisting of: vegetable oil(s), animal fat(s), industrial byproduct(s), and combinations thereof.",
    "8. The process of claim 1, wherein the unsaturated fatty acid is oleic acid.",
    "9. The process of claim 1, wherein the selective conversion results in at least about 65% to about 85% selective conversion of the unsaturated fatty acid into the saturated branched-chain fatty acid alkyl ester(s) thereof.",
    "10. The process of claim 1, wherein the saturated branched-chain fatty acid is mainly isostearic acid mixed with other saturated branched-chain fatty acids depending on feedstock.",
    "11. The process of claim 1, wherein subjecting the unsaturated fatty acid to the skeletal isomerization reaction occurs at a temperature from about 240° C. to about 260° C.",
    "12. The process of claim 1, wherein subjecting the unsaturated fatty acid to the skeletal isomerization reaction occurs at a temperature of about 260° C.",
    "13. The process of claim 1, wherein the furnace is a muffle furnace.",
    "14. The process of claim 1, wherein the zeolite catalyst is selected from the group consisting of: NH4 + -Ferrierite; NH4 + -ZSM-5; NH4 + -BETA; and any combination thereof.",
    "15. The process of claim 1, wherein the zeolite catalyst is selected from the group consisting of: NH4 + -Ferrierite with a SiO 2 /Al 2 O 3 ratio of 20; NH4 + -ZSM-5 with a SiO 2 /Al 2 O 3 ratio of 23; NH4 + -BETA with a SiO 2 /Al 2 O 3 ratio of 25; and any combination thereof.",
    "16. The process of claim 1, wherein the zeolite catalyst has a SiO 2 /Al 2 O 3 ratio from about 17 to about 25.",
    "17. The process of claim 1, wherein the zeolite catalyst has a SiO 2 /Al 2 O 3 ratio from about 20 to about 25.",
    "18. The process of claim 1, wherein the zeolite catalyst is converted into the activated zeolite catalyst at a temperature from about 400° C. to about 500° C.",
    "19. The process of claim 1, wherein the zeolite catalyst is converted into the activated zeolite catalyst at a temperature of about 450° C. to about 500° C.",
    "20. The process of claim 1, wherein the oligomerization reducing agent is selected from the group consisting of: amine; phosphine; triarylphosphine; dialkylarylphosphine; trialkylphosphine; and any combinations or mixtures thereof.",
    "21. The process of claim 20, wherein the amine is selected from the group consisting of: dimethylamine; trimethylamine; diethylamine; trimethylamine; diisopropylamine; triisopropylamine; triphenylamine; diphenylamine; and any combinations or mixtures thereof.",
    "22. The process of claim 20, wherein said phosphine is selected from the group consisting of: methylphosphine; butylphosphine; dibutylphosphine; tributylphosphine; phenylphosphine; diphenylphosphine; and any combinations or mixtures thereof.",
    "23. The process of claim 20, wherein said triarylphosphine is selected from the group consisting of: triphenylphosphine; tri-p-tolylphosphine; tri(o-tolyl)phosphine; tri-m-tolylphosphine; trixylyl-phosphine, tris(p-ethylphenyl)phosphine, tris(p-methoxyphenyl)phosphine, tris(4-fluorophenyl)phosphine; tris(4-methoxyphenyl)phosphine; tris(dimethylamino)phosphine; tris(trimethylsilyl)phosphine; triisopropylphosphine; and any combinations or mixtures thereof.",
    "24. The process of claim 20, wherein the dialkylarylphosphine is selected from the group consisting of: di-n-butylphenylphosphine; dicyclohexylphenylphosphine; and any combinations or mixtures thereof.",
    "25. The process of claim 20, wherein the trialkylphosphine is selected from the group consisting of: tri-n-butylphosphine; tricyclohexylphosphine; tri-n-octylphosphine; trimethyphosphine; triethylphosphine; triisopropylphosphine; tricyclopentylphosphine; and any combinations or mixtures thereof.",
    "26. The process of claim 1, wherein the oligomerization reducing agent is triphenylphosphine.",
    "27. The process of claim 1, wherein regenerating the spent zeolite catalyst by heating the spent zeolite to a temperature of about 120° C. to about 500° C. for a time of about 3 hours to about 5 hours to create the regenerated zeolite catalyst that is functional for use as the activated zeolite catalyst is performed for at least about 10 cycles.",
    "28. A method of regenerating a zeolite catalyst, the method comprising: recovering a spent zeolite catalyst and regenerating the spent zeolite catalyst without the use of an acid treatment step by heating the spent zeolite catalyst to a temperature of about 120° C. to about 500° C. for a time of about 3 hours to about 5 hours to create a regenerated zeolite catalyst that is functional for use as an activated zeolite catalyst.",
    "29. The method of claim 28, further comprising (a) calcining the zeolite catalyst at a temperature from about 500° C. to about 600° C. to create the activated zeolite catalyst; (b) using the activated zeolite catalyst in a skeletal isomerization reaction to convert an unsaturated fatty acid into a saturated branched-chain fatty acid and/or alkyl ester(s) thereof to create reaction products and the spent zeolite catalyst.",
    "30. The method of claim 28, wherein the zeolite catalyst is selected from the group consisting of: NH4 + -Ferrierite; NH4 + -ZSM-5; NH4 + -BETA; and any combination thereof."
  ],
  "description_excerpt": "The disclosed invention relates generally to novel methods of preparing saturated branched-chain fatty acids. More specifically, the invention relates to novel catalytic processes for the conversion of unsaturated linear chain fatty acids derived from renewable sources to saturated branched-chain fatty acids through the use of acidic zeolite catalysts and the economically favorable regeneration of such catalysts.\n\nCommercial scale production of saturated branched-chain fatty acids or alkyl esters thereof using starting materials from renewable sources is gaining enormous interest because of their favorable properties, including better biodegradability as compared to petroleum-based materials, lower toxicity, lower flammability due to their lower vapor pressures, lower melting points, and lower viscosity. These properties make such fatty acids an important feedstock for the production of lubricants, greases, emulsifiers, cosmetic products, surfactants, biodiesel, hydraulic fluids, and many more products. In the petrochemical industry, for example, branched-chain hydrocarbons are consumed for improved octane numbers. Environmental concerns over the use of petroleum-based materials in the lubricant industry have stimulated much research to find suitable alternative materials. In this regard, lubricating fluids derived from renewable fats and oils are of interest because of their purported advantages over petroleum-based materials (Hill, K., Pure Appl. Chem., 79: 1999-2011 (2007)).",
  "cpc": [
    "C07C 51/36",
    "B01J 29/40",
    "B01J 29/65",
    "B01J 29/7007",
    "B01J 29/90",
    "B01J 35/615",
    "B01J 35/617",
    "B01J 35/633",
    "B01J 35/635",
    "B01J 38/02",
    "C07C 51/353",
    "Y02P 20/584"
  ],
  "ipc": [
    "B01J 29/40",
    "B01J 29/65",
    "B01J 29/70",
    "B01J 29/90",
    "B01J 38/02",
    "C07C 51/36"
  ],
  "assignees": [
    "US Department of Agriculture USDA"
  ],
  "inventors": [
    "Majher I Sarker",
    "HELEN N. Lew",
    "Robert A. Moreau"
  ],
  "filing_date": "2016-12-29",
  "publication_date": "2018-10-02",
  "grant_date": "2018-10-02",
  "priority_date": "2016-12-29",
  "application_number": "US-201615394015-A",
  "family_id": "62708864",
  "cited_by_count": 4,
  "citations": [
    "US9115076B2",
    "WO2015144232A1"
  ]
}