RU2016104053A - Способ каталитической конверсии кетокислот через промежуточные димеры кетокислот и их гидропереработки в углеводороды - Google Patents

Способ каталитической конверсии кетокислот через промежуточные димеры кетокислот и их гидропереработки в углеводороды Download PDF

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RU2016104053A
RU2016104053A RU2016104053A RU2016104053A RU2016104053A RU 2016104053 A RU2016104053 A RU 2016104053A RU 2016104053 A RU2016104053 A RU 2016104053A RU 2016104053 A RU2016104053 A RU 2016104053A RU 2016104053 A RU2016104053 A RU 2016104053A
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metal oxide
acid
weight
reaction
reaction mixture
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RU2638835C2 (ru
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Юкка Мюллюойя
Рами ПИИЛОЛА
Маария СЕЛЯНТАУС
Матс КЯЛДСТРЁМ
Марина ЛИНДБЛАД
Элиас ИКОНЕН
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Несте Ойю
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Claims (32)

1. Способ увеличения молекулярной массы кетокислоты, включающий в себя следующие стадии:
- подают в реактор исходный материал, содержащий, по меньшей мере, одну кетокислоту,
- проводят в исходном материале первую реакцию C-C-связывания в присутствии катализатора на основе ионообменной смолы для образования, по меньшей мере, одного димера кетокислоты,
- подают в реактор реакционную смесь, содержащую, по меньшей мере, один димер кетокислоты,
- проводят в реакционной смеси вторую реакцию C-C-связывания при температуре, по меньшей мере, 200°C.
2. Способ по п. 1, в котором, по меньшей мере, один димер кетокислоты представляет собой димер γ-кетокислоты, предпочтительно, димер левулиновой кислоты; и/или
содержание, по меньшей мере, одного димера кетокислоты в реакционной смеси составляет, по меньшей мере, 30% по массе, предпочтительно, по меньшей мере, 40% по массе, более предпочтительно, по меньшей мере, 50% по массе, еще более предпочтительно, по меньшей мере, 55% по массе, наиболее предпочтительно, по меньшей мере, 60% по массе.
3. Способ по п. 1 или 2, в котором первую и вторую реакции C-C-связывания проводят в первом и во втором реакторе, соответственно.
4. Способ по п. 1 или 2, в котором содержание воды в реакционной смеси составляет менее 15,0% по массе, предпочтительно менее 10,0% по массе, более предпочтительно менее 5,0% по массе.
5. Способ по п. 1 или 2, в котором, по меньшей мере, одна кетокислота в исходном материале представляет собой γ-кетокислоту, предпочтительно левулиновую кислоту; и/или
в котором средний диаметр пор катализатора на основе ионообменных смол составляет от 150
Figure 00000001
до 300
Figure 00000001
, предпочтительно от 200
Figure 00000001
до 250
Figure 00000001
; и/или
в котором первую реакцию C-C-связывания проводят при температуре от 100°C до 190°C, предпочтительно от 120°C до 160°C, более предпочтительно от 120°C до 140°C.
6. Способ по п. 1 или 2, в котором первую реакцию C-C-связывания в исходном материале проводят в присутствии водорода и катализатор на основе ионообменной смолы содержит, по меньшей мере, один гидрирующий металл, выбранный из группы VIII периодической системы элементов, предпочтительно выбранный из Co, Ni, Ru, Rh, Pd и Pt, более предпочтительно представляющий собой Pd.
7. Способ по п. 1 или 2, в котором вторую реакцию C-C-связывания в реакционной смеси проводят в отсутствие катализатора.
8. Способ по п. 1 или 2, в котором вторую реакцию C-C-связывания в реакционной смеси проводят в присутствии твердотельной металлооксидной катализаторной системы, содержащей первый оксид металла и второй оксид металла.
9. Способ по п. 8, в котором каталитическая система имеет удельную площадь поверхности от 10 м2/г до 500 м2/г; и/или
в котором твердотельная каталитическая система содержит смесь, в которой первый оксид металла нанесен на второй оксид металла; и/или
в котором плотность атомов металла на поверхности первого оксида металла, нанесенного на второй оксид металла, составляет от 0.5 атомов/нм2 до 20 атомов/нм2; и/или
в котором первый оксид металла содержит оксид одного из следующих металлов: K, Li, Be, B, Na, Mg, Al, Si, Ca, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Br, Sr, Y, Zr, Nb, Mo, Ba, W, Pb, Bi, La, Ce, Th, а второй оксид металла содержит оксид одного из следующих металлов: K, Li, Be, B, Na, Mg, Al, Si, Ca, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Br, Sr, Y, Zr, Nb, Mo, Ba, W, Pb, Bi, La, Ce, Th или их сочетание, причем первый оксид металла отличается от второго оксида металла; и/или
в котором первый оксид металла содержит оксид калия, а второй оксид металла содержит оксид титана или первый оксид металла содержит оксид вольфрама или церия, а второй оксид металла содержит оксид циркония, титана, кремния, ванадия или хрома, предпочтительно оксид циркония или титана; и/или
в котором содержание первого оксида металла в каталитической системе, определяемое по отношению массы оксида металла к общей массе катализатора, составляет от 1,0% до 40,0% по массе, предпочтительно от 2,0% до 30,0% по массе, более предпочтительно от 13,0% до 30,0% по массе.
10. Способ по п. 1 или 2, в котором реакционная смесь дополнительно содержит, по меньшей мере, одну кетокислоту, предпочтительно γ-кетокислоту, более предпочтительно левулиновую кислоту.
11. Способ по п. 10, в котором содержание, по меньшей мере, одной кетокислоты в реакционной смеси составляет, по меньшей мере, 1,0% по массе, предпочтительно, по меньшей мере, 5,0% по массе, более предпочтительно, по меньшей мере, 10,0% по массе или, по меньшей мере, 30,0% по массе; и/или
в котором отношение содержания мо массе, по меньшей мере, одной кетокислоты к содержанию по массе, по меньшей мере, одного димера кетокислоты (кетокислота / димер кетокислоты) в реакционной смеси составляет от 1:5 до 10:1, предпочтительно от 1:3 до 5:1.
12. Способ по п. 1 или 2, в котором реакционную смесь подают в реактор в жидком состоянии; и/или
в котором вторую реакцию C-C-связывания проводят при температуре от 200°C до 400°C, предпочтительно при температуре от 210°C до 300°C, более предпочтительно от 220°C до 280°C, еще более предпочтительно от 220°C до 260°C; и/или
в котором вторую реакцию C-C-связывания проводят под давлением от 0,5 бар до 150 бар, предпочтительно от 1,0 бар до 50 бар, более предпочтительно от 1,0 бар до 20 бар; и/или
в котором вторую реакцию C-C-связывания проводят при массовой среднечасовой скорости подачи (кг реакционной смеси / кг катализатора × час) от 0,05 ч-1 до 2,0 ч-1, предпочтительно от 0,1 ч-1 до 1,8 ч-1, более предпочтительно от 0,2 ч-1 до 1,5 ч-1, наиболее предпочтительно от 0,25 ч-1 до 1,25 ч-1; и/или
в котором реакционная смесь содержит, по меньшей мере, одну из кислот: 4-гидрокси-4-метил-6-оксононандикарбоновая кислота, 3-ацетил-4-гидрокси-4-метилгептандикарбоновая кислота, 5-(2-метил-5-оксотетрагидрофуран-2-ил)-4-оксопентановая кислота, (E)-4-метил-6-оксонон-4-ендикарбоновая кислота, 4-гидрокси-6-метилнонандикарбоновая кислота, (E)-6-гидрокси-4-метилнон-4-ендикарбоновая кислота, (Z)-3-ацетил-4-метилгепт-3-ендикарбоновая кислота, 3-(3-ацетил-2-метил-5-оксотетрагидрофуран-2-ил)-пропановая кислота, (Z)-3-1(1-гидроксиэтил)-4-метилгепт-3-ендикарбоновая кислота и 3-(1-гидроксиэтил)-4-метилгептандикарбоновая кислота.
13. Продукт реакции, полученный при проведении второй реакции C-C-связывания способом, охарактеризованным по одному из пп. 1-12.
14. Способ получения углеводородов, включающий в себя стадию увеличения молекулярной массы кетокислоты способом, охарактеризованным по одному из пп. 1-12, для получения продукта реакции и стадию проведения в этом продукте реакции гидродезоксигенирования, а также, опционально, стадию изомеризации.
15. Углеводородная композиция, полученная способом, охарактеризованным по п. 14.
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