RU2019104895A - Способы получения углеводородных композиций с пониженным кислотным числом и для выделения короткоцепочечных жирных кислот - Google Patents
Способы получения углеводородных композиций с пониженным кислотным числом и для выделения короткоцепочечных жирных кислот Download PDFInfo
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- RU2019104895A RU2019104895A RU2019104895A RU2019104895A RU2019104895A RU 2019104895 A RU2019104895 A RU 2019104895A RU 2019104895 A RU2019104895 A RU 2019104895A RU 2019104895 A RU2019104895 A RU 2019104895A RU 2019104895 A RU2019104895 A RU 2019104895A
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- Prior art keywords
- fatty acid
- adsorbent
- acid
- chain fatty
- short chain
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- 238000000034 method Methods 0.000 title claims 38
- 150000004666 short chain fatty acids Chemical class 0.000 title claims 18
- 229930195733 hydrocarbon Natural products 0.000 title claims 16
- 150000002430 hydrocarbons Chemical class 0.000 title claims 16
- 239000000203 mixture Substances 0.000 title claims 16
- 239000004215 Carbon black (E152) Substances 0.000 title claims 12
- 239000002253 acid Substances 0.000 title claims 4
- 238000002955 isolation Methods 0.000 title 1
- 235000021391 short chain fatty acids Nutrition 0.000 title 1
- 239000003463 adsorbent Substances 0.000 claims 18
- 235000014113 dietary fatty acids Nutrition 0.000 claims 7
- 239000000194 fatty acid Substances 0.000 claims 7
- 229930195729 fatty acid Natural products 0.000 claims 7
- 150000004665 fatty acids Chemical class 0.000 claims 7
- 239000012530 fluid Substances 0.000 claims 7
- 235000021588 free fatty acids Nutrition 0.000 claims 7
- 238000010438 heat treatment Methods 0.000 claims 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 6
- 239000002585 base Substances 0.000 claims 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000003957 anion exchange resin Substances 0.000 claims 3
- 239000001569 carbon dioxide Substances 0.000 claims 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 3
- 150000002632 lipids Chemical class 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims 2
- 239000006227 byproduct Substances 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 2
- 235000012239 silicon dioxide Nutrition 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 241000195493 Cryptophyta Species 0.000 claims 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- -1 alkaline earth metal carbonate Chemical class 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 229940114079 arachidonic acid Drugs 0.000 claims 1
- 235000021342 arachidonic acid Nutrition 0.000 claims 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000008162 cooking oil Substances 0.000 claims 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims 1
- 229940090949 docosahexaenoic acid Drugs 0.000 claims 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000003925 fat Substances 0.000 claims 1
- 235000019197 fats Nutrition 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229960004488 linolenic acid Drugs 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 235000019198 oils Nutrition 0.000 claims 1
- 150000003904 phospholipids Chemical class 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000004671 saturated fatty acids Chemical class 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 239000003784 tall oil Substances 0.000 claims 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims 1
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 1
- 239000008158 vegetable oil Substances 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
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- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
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- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
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Claims (42)
1. Способ получения углеводородов из источника жирных кислот, включающий в себя:
(a) нагревание источника жирных кислот с получением первой композиции, содержащей углеводороды и по меньшей мере одну свободную короткоцепочечную жирную кислоту; и
(b) удаление свободной короткоцепочечной жирной кислоты из первой композиции с получением конечной углеводородной композиции, имеющей кислотное число менее 0,1, измеренное по ASTM D974.
2. Способ по п.1, в котором стадия (b) включает контактирование углеводородной композиции с адсорбентом.
3. Способ по п.2, в котором углеводородную композицию пропускают через колонку, содержащую адсорбент.
4. Способ по п.2, в котором адсорбент включает диоксид кремния или модифицированный диоксид кремния.
5. Способ по п.2, в котором свободная короткоцепочечная жирная кислота впоследствии удаляется из адсорбента.
6. Способ по п.5, в котором адсорбент приводят в контакт с полярным растворителем для удаления свободной короткоцепочечной жирной кислоты из адсорбента.
7. Способ по п.6, в котором полярный растворитель включает спирт, нитрил, простой эфир, сложный эфир или хлоруглеводород.
8. Способ по п.5, в котором адсорбент приводят в контакт со сверхкритическим флюидом диоксида углерода для удаления свободной короткоцепочечной жирной кислоты из адсорбента.
9. Способ по п.5, в котором адсорбент приводят в контакт со сверхкритическим флюидным продуктом для удаления свободной короткоцепочечной жирной кислоты из адсорбента, где сверхкритический флюидный продукт является побочным продуктом со стадии (а).
10. Способ по п.9, в котором сверхкритический флюидный продукт включает монооксид углерода, диоксид углерода, метан, этан, водород, или любое их сочетание.
11. Способ по п.5, в котором свободную короткоцепочечную жирную кислоту непрерывно удаляют из адсорбента.
12. Способ по п.1, в котором способ включает в себя
(a) нагревание свободной жирной кислоты в реакторе с получением первой композиции, содержащей углеводороды и по меньшей мере одну свободную короткоцепочечную жирную кислоту;
(b) введение первой композиции в колонку, содержащую адсорбент, где происходит удаление свободной короткоцепочечной жирной кислоты из первой композиции с получением конечной углеводородной композиции, имеющей кислотное число менее 0,02, измеренное по ASTM D974;
(c) удаление свободной короткоцепочечной жирной кислоты из адсорбента; и
(d) введение свободной короткоцепочечной жирной кислоты в реактор стадии (а) и нагревание свободной короткоцепочечной жирной кислоты с получением второй углеводородной композиции и по меньшей мере одной второй свободной короткоцепочечной жирной кислоты,
при этом стадии (а) - (d) осуществляются непрерывно.
13. Способ по п.12, в котором адсорбент включает диоксид кремния или модифицированный диоксид кремния.
14. Способ по п.13, в котором адсорбент приводят в контакт со сверхкритическим флюидом диоксида углерода для удаления свободной короткоцепочечной жирной кислоты из адсорбента.
15. Способ по п.13, в котором адсорбент приводят в контакт со сверхкритическим флюидным продуктом для удаления свободной короткоцепочечной жирной кислоты из адсорбента, где сверхкритический флюидный продукт является побочным продуктом со стадии (а).
16. Способ по п.1, в котором стадия (b) включает контактирование углеводородной композиции с основанием.
17. Способ по п.14, в котором основание включает гидроксид щелочного металла, карбонат щелочного металла, гидроксид щелочноземельного металла или карбонат щелочноземельного металла.
18. Способ по п.14, в котором основание включает гидроксид натрия или гидроксид калия.
19. Способ по п.14, в котором углеводородную композицию приводят в контакт с водным раствором основания для получения водной фазы и углеводородной фазы и удаления углеводородной фазы.
20. Способ по п.14, в котором молярное количество основания больше или равно молярному эквиваленту групп карбоновой кислоты, присутствующих в короткоцепочечной жирной кислоте.
21. Способ по п.1, в котором стадия (b) включает контактирование углеводородной композиции с анионообменной смолой.
22. Способ по п.21, в котором анионообменная смола включает смесь полимера и соединения со множеством аминогрупп.
23. Способ по п.21, в котором анионообменная смола включает полистирол и полимер со множеством аминогрупп.
24. Способ по пп.1-23, в котором короткоцепочечную жирную кислоту непрерывно удаляют и нагревают для получения дополнительных углеводородов.
25. Способ по пп.1-23, в котором источник жирных кислот содержит моноглицериды, диглицерид, триглицерид, липид, свободную жирную кислоту или ее соль, или любое их сочетание.
26. Способ по пп.1-23, в котором источник жирных кислот включает растительные масла, животные жиры, масла из водорослей или грибов, талловые масла, использованный кулинарный жир, липиды из твердых биологических веществ, липиды, фосфолипиды или триглицериды.
27. Способ по пп.1-23, в котором до стадии (a) свободная жирная кислота выделяется из источника жирных кислот.
28. Способ по п.27, где способ включает в себя (i) выделение одного или более триглицеридов из источника жирных кислот, (ii) гидролиз триглицерида с получением свободной жирной кислоты, и (iii) выделение свободной жирной кислоты.
29. Способ по п.27, в котором свободная жирная кислота включает насыщенную жирную кислоту, ненасыщенную жирную кислоту или их сочетание.
30. Способ по п.27, в котором свободная жирная кислота включает масляную кислоту, лауриновую кислоту, миристиновую кислоту, пальмитиновую кислоту, стеариновую кислоту, арахиновую кислоту, альфа-линоленовую кислоту, докозагексаеновую кислоту, эйкозапентаеновую кислоту, линолевую кислоту, арахидоновую кислоту, олеиновую кислоту, эруковую кислоту, жирную кислоту природного происхождения из растительного или животного источника, или любое их сочетание.
31. Способ по пп.1-23, в котором стадию (а) нагревания осуществляют при температуре от 220°C до 650°C.
32. Способ по пп.1-23, в котором стадию (а) нагревания осуществляют при температуре от 250°C до 500°C в течение периода времени от 2 с до 8 ч.
33. Способ по пп.1-23, в котором стадию (а) нагревания осуществляют в присутствии одного или более алкенов.
34. Способ по пп.1-23, в котором стадию (а) нагревания осуществляют в отсутствие дополнительного водорода.
35. Углеводородная композиция, полученная способом по пп.1-23.
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| JP2023075130A (ja) | 2023-05-30 |
| EP3487959A1 (en) | 2019-05-29 |
| MX2019001072A (es) | 2020-01-20 |
| AU2017303971B2 (en) | 2023-05-11 |
| BR112019001395B1 (pt) | 2022-11-16 |
| BR112019001395A2 (pt) | 2019-05-07 |
| RU2019104895A3 (ru) | 2020-11-09 |
| KR20190030753A (ko) | 2019-03-22 |
| WO2018020321A1 (en) | 2018-02-01 |
| EP3487959A4 (en) | 2020-02-19 |
| US10995276B2 (en) | 2021-05-04 |
| CA3032039A1 (en) | 2018-02-01 |
| CN109790470A (zh) | 2019-05-21 |
| RU2749418C2 (ru) | 2021-06-09 |
| CA3032039C (en) | 2024-05-14 |
| KR102449807B1 (ko) | 2022-09-30 |
| JP2019528257A (ja) | 2019-10-10 |
| US20190233735A1 (en) | 2019-08-01 |
| JP7688665B2 (ja) | 2025-06-04 |
| UA128198C2 (uk) | 2024-05-08 |
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