RU2017113922A - Способ получения ароматических соединений - Google Patents
Способ получения ароматических соединений Download PDFInfo
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- RU2017113922A RU2017113922A RU2017113922A RU2017113922A RU2017113922A RU 2017113922 A RU2017113922 A RU 2017113922A RU 2017113922 A RU2017113922 A RU 2017113922A RU 2017113922 A RU2017113922 A RU 2017113922A RU 2017113922 A RU2017113922 A RU 2017113922A
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- catalyst
- zsm
- aromatic compounds
- conversion
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- 150000001491 aromatic compounds Chemical class 0.000 title claims 10
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 17
- 239000003054 catalyst Substances 0.000 claims 14
- 238000006243 chemical reaction Methods 0.000 claims 8
- 229910021536 Zeolite Inorganic materials 0.000 claims 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical group O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 6
- 239000010457 zeolite Substances 0.000 claims 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 3
- 239000011230 binding agent Substances 0.000 claims 3
- 239000012084 conversion product Substances 0.000 claims 3
- 239000007789 gas Substances 0.000 claims 3
- 238000000197 pyrolysis Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000002023 wood Substances 0.000 claims 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 2
- 239000005995 Aluminium silicate Substances 0.000 claims 1
- 150000007824 aliphatic compounds Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 229910000323 aluminium silicate Inorganic materials 0.000 claims 1
- 235000012211 aluminium silicate Nutrition 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 238000001354 calcination Methods 0.000 claims 1
- 229910001657 ferrierite group Inorganic materials 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052680 mordenite Inorganic materials 0.000 claims 1
- -1 olefins Chemical class 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000011148 porous material Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000004408 titanium dioxide Substances 0.000 claims 1
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- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/002—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal in combination with oil conversion- or refining processes
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- D—TEXTILES; PAPER
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- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C11/00—Regeneration of pulp liquors or effluent waste waters
- D21C11/12—Combustion of pulp liquors
- D21C11/125—Decomposition of the pulp liquors in reducing atmosphere or in the absence of oxidants, i.e. gasification or pyrolysis
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/08—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule
- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
- C07C4/16—Thermal processes
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- C07C4/12—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene
- C07C4/14—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by splitting-off an aliphatic or cycloaliphatic part from the molecule from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene splitting taking place at an aromatic-aliphatic bond
- C07C4/18—Catalytic processes
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- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
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- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/40—Thermal non-catalytic treatment
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- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
- C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
- C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G51/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more cracking processes only
- C10G51/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more cracking processes only plural serial stages only
- C10G51/04—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more cracking processes only plural serial stages only including only thermal and catalytic cracking steps
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C11/00—Regeneration of pulp liquors or effluent waste waters
- D21C11/0085—Introduction of auxiliary substances into the regenerating system in order to improve the performance of certain steps of the latter, the presence of these substances being confined to the regeneration cycle
- D21C11/0092—Substances modifying the evaporation, combustion, or thermal decomposition processes of black liquor
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C11/00—Regeneration of pulp liquors or effluent waste waters
- D21C11/06—Treatment of pulp gases; Recovery of the heat content of the gases; Treatment of gases arising from various sources in pulp and paper mills; Regeneration of gaseous SO2, e.g. arising from liquors containing sulfur compounds
- D21C11/063—Treatment of gas streams comprising solid matter, e.g. the ashes resulting from the combustion of black liquor
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- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/82—Phosphates
- C07C2529/84—Aluminophosphates containing other elements, e.g. metals, boron
- C07C2529/85—Silicoaluminophosphates (SAPO compounds)
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- C07C2529/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
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- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1003—Waste materials
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- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
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- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/30—Aromatics
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Claims (21)
1. Способ получения низкомолекулярных ароматических соединений из черного щелока, включающий:
предоставление черного щелока, который является производным от щелочной обработки древесной щепы;
подвергание черного щелока обработке пиролизом, чтобы получить от пиролизованного черного щелока газ и массив твердотельного вещества, содержащий обуглившееся вещество и соли, в первом реакторе, где соли являются в основном производными от обработки черного щелока;
приведение по меньшей мере части газа от пиролизованного черного щелока в контактирование с катализатором во втором реакторе, который отличается от первого реактора, чтобы предоставить конверсионную обработку для получения на выходе продукта конверсии; и
извлечение низкомолекулярных ароматических соединений из продукта конверсии.
2. Способ по п. 1, в котором обработку пиролизом выполняют без добавления катализатора.
3. Способ по п. 1 или 2, в котором древесная щепа является производной от твердой древесины.
4. Способ по любому одному из пп. 1-3, в котором обработку пиролизом черного щелока выполняют при температуре от 350°C до 700°C при давлении между 0,1 и 6 бар абс.
5. Способ по любому одному из пп. 1-4, в котором по меньшей мере часть массива твердотельного вещества собирают и нагревают до температуры, которая является достаточно высокой, чтобы извлечь соль в массиве твердотельного вещества.
6. Способ по любому одному из пп. 1-5, в котором конверсионная обработка включает преобразование комплексных ароматических соединений в низкомолекулярные ароматические соединения, преобразование ароматических соединений, содержащих кислород, и алифатических соединений, содержащих кислород, в низкомолекулярные ароматические соединения без атомов кислорода, и/или преобразование углеводородов, таких как олефины, в низкомолекулярные ароматические соединения.
7. Способ по любому одному из пп. 1-6, в котором конверсионную обработку выполняют при температуре между 200°C и 1000°C, предпочтительно между 350°C и 650°C.
8. Способ по любому одному из пп. 1-7, в котором при конверсионной обработке катализатор присутствует при массовом отношении газа от пиролизованного черного щелока к катализатору в интервале от 5:1 до 1:20, и более предпочтительно в интервале от 1:1 до 1:5.
9. Способ по любому одному из пп. 1-8, в котором катализатор является цеолитовым катализатором, подходящим образом, выбранным из алюмосиликатов, силикоалюмофосфатов (SAPO), силикалитов и/или их комбинаций.
10. Способ по любому одному из пп. 1-9, в котором катализатор является кислотным и/или предпочтительно сделан кислотным посредством ионного обмена аммонийными солями и последующего обжига.
11. Способ по любому одному из пп. 1-10, в котором катализатор имеет отношение кремнезема к глинозему от 5 до 300, предпочтительно от 10 до 150, более предпочтительно от 20 до 90.
12. Способ по любому одному из пп. 1-11, в котором катализатор имеет наибольший размер внутренних пор в интервале от 4,5 до 12 Å, предпочтительно от 5 до 7 Å.
13. Способ по любому одному из пп. 1-12, в котором катализатор выбран из группы, состоящей из ZSM-5, ZSM-11, ZSM-35, ZSM-23, ферриерита, цеолита Бета, цеолита Y, цеолита X, морденита, цеолита A, IM-5, SSZ-20, SSZ-55, MCM-22, TNU-9, NU-87, ZSM-57, ZSM-48, EU-1, SSZ-35, SSZ-44, ультрастабильного цеолита Ultrastable Y (US-Y), SBA-15, AL-SBA15, ZSM-18, LZ-135, ZSM-10, MCM-68, SSZ-57, ECR-1, ITQ-25, COK-14, MOR, ZSM-12 SSZ-48 и их комбинаций и предпочтительно является ZSM-5.
14. Способ по любому одному из пп. 1-13, в котором катализатор связывают посредством связующего, чтобы образовать связанный катализатор, и где связующее выбирают из группы, состоящей из оксида алюминия, кремнезема, кремнезема-оксида алюминия, диоксида титана, диоксида циркония, каолина и их смесей.
15. Способ по любому одному из пп. 1-14, в котором количество связующего в связанном катализаторе находится в интервале от 0 до 80 масс.%, предпочтительно от 40 до 70 масс.%, в расчете на массу связанного катализатора.
16. Способ по любому одному из пп. 1-15, в котором конверсионную обработку выполняют в неподвижном слое, подвижном слое или псевдоожиженном слое.
17. Способ по любому одному из пп. 1-16, в котором извлечение ароматических соединений происходит посредством подвергания продукта конверсии фракционированию для получения фракции, обогащенной низкомолекулярными ароматическими соединениями.
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PCT/EP2015/071655 WO2016046163A2 (en) | 2014-09-22 | 2015-09-22 | Process for the preparation of aromatic compounds |
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US4493797A (en) * | 1983-12-22 | 1985-01-15 | Domtar Inc | Apparatus and method involving supercritical fluid extraction |
US5504259A (en) * | 1992-10-29 | 1996-04-02 | Midwest Research Institute | Process to convert biomass and refuse derived fuel to ethers and/or alcohols |
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US20070169412A1 (en) * | 2006-01-26 | 2007-07-26 | Georgia Tech Research Corporation | Sulfur- and alkali-tolerant catalyst |
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US20120029243A1 (en) | 2010-07-29 | 2012-02-02 | Basf Se | Catalyst- and lignin-comprising composition and its use for preparing an aromatics composition |
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US20130324772A1 (en) * | 2012-06-05 | 2013-12-05 | University Of Massachusetts | Method for converting a hydrocarbonaceous material to a fluid hydrocarbon product comprising p-xylene |
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CN106715653A (zh) | 2017-05-24 |
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US20180237989A1 (en) | 2018-08-23 |
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CA2961851C (en) | 2022-04-26 |
CL2017000691A1 (es) | 2017-12-01 |
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