HRP20151101T1 - Postupak za pripravu nižih ugljikovodika iz glicerola - Google Patents
Postupak za pripravu nižih ugljikovodika iz glicerola Download PDFInfo
- Publication number
- HRP20151101T1 HRP20151101T1 HRP20151101TT HRP20151101T HRP20151101T1 HR P20151101 T1 HRP20151101 T1 HR P20151101T1 HR P20151101T T HRP20151101T T HR P20151101TT HR P20151101 T HRP20151101 T HR P20151101T HR P20151101 T1 HRP20151101 T1 HR P20151101T1
- Authority
- HR
- Croatia
- Prior art keywords
- catalyst
- glycerol
- acrolein
- hydrocarbon
- catalyzing
- Prior art date
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims 53
- 229930195733 hydrocarbon Natural products 0.000 title claims 12
- 150000002430 hydrocarbons Chemical class 0.000 title claims 12
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims 25
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 20
- 238000000034 method Methods 0.000 claims 17
- 239000004215 Carbon black (E152) Substances 0.000 claims 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 238000005984 hydrogenation reaction Methods 0.000 claims 5
- 239000001294 propane Substances 0.000 claims 5
- 239000003377 acid catalyst Substances 0.000 claims 4
- 238000006297 dehydration reaction Methods 0.000 claims 4
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims 3
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims 3
- 238000006606 decarbonylation reaction Methods 0.000 claims 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/2076—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by a transformation in which at least one -C(=O)- moiety is eliminated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/04—Ethylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/52—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition by dehydration and rearrangement involving two hydroxy groups in the same molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C9/00—Aliphatic saturated hydrocarbons
- C07C9/02—Aliphatic saturated hydrocarbons with one to four carbon atoms
- C07C9/06—Ethane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C9/00—Aliphatic saturated hydrocarbons
- C07C9/02—Aliphatic saturated hydrocarbons with one to four carbon atoms
- C07C9/08—Propane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/30—Tungsten
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals combined with metals, oxides or hydroxides provided for in groups C07C2523/02 - C07C2523/36
- C07C2523/56—Platinum group metals
- C07C2523/63—Platinum group metals with rare earths or actinides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Metoda za pripravu ugljikovodika obuhvaća dva ili tri atoma ugljika iz glicerola, pri čemu ugljikovodik jedino sadrži atome ugljika i vodika i pri čemu metoda obuhvaća korake:
opskrbljivanja glicerolom;
pretvorbe glicerola u akrolein uporabom prvog katalizatora, kataliziranjem reakcija dehidracije; i
pretvorbe nastalog akroleina u ugljikovodik koji sadrži dva ili tri atoma ugljika, uporabom drugog katalizatora kataliziranjem reakcija dekarbonilacije, ili uporabom drugog katalizatora kataliziranjem reakcija hidrogenacije i trećeg katalizatora kataliziranjem reakcija dehidracije.
2. Metoda u skladu s patentnim zahtjevom 1, pri čemu je ugljikovodik etan ili eten i pri čemu drugi katalizator katalizira reakcije dekarbonilacije.
3. Metoda u skladu s patentnim zahtjevom 2, pri čemu je ugljikovodik etan i pri čemu je drugi katalizator odabran između katalizatora koji katalizira pomak plina vodom (WGS), reakcije hidrogenacije i dekarbonilacije.
4. Metoda u skladu s patentnim zahtjevom 3, pri čemu drugi katalizator sadrži Pt na CeO2.
5. Metoda u skladu s bilo kojim od prethodnih patentnih zahtjeva, pri čemu su prvi i drugi katalizatori prisutni u prvom reaktoru, koji je isti reaktor.
6. Metoda u skladu s patentnim zahtjevom 1, nadalje obuhvaća korake:
opskrbljivanja ugljikovodikom, pri čemu je ugljikovodik propan ili propen i pri čemu drugi katalizator katalizira reakcije hidrogenacije i treći katalizator katalizira reakcije dehidracije.
7. Metoda u skladu s patentnim zahtjevom 6, pri čemu je ugljikovodik propan i pri čemu je vodik priskrbljen u stehiometrijskom suvišku u odnosu na glicerol.
8. Metoda u skladu s bilo kojim od prethodnih patentnih zahtjeva, pri čemu je glicerol priskrbljen kao smjesa s vodom i koncentracija glicerola u smjesi glicerola i vode je 1 do 75 wt%.
9. Metoda u skladu s patentnim zahtjevom 8, pri čemu temperatura smjese glicerol/voda, kada je priskrbljena, iznosi 200 do 400°C, i pri čemu je glicerol pretvoren u akrolein na temperaturi od 200 do 400°C pod tlakom od 2 do 10 bara.
10. Metoda u skladu s bilo kojim od prethodnih patentnih zahtjeva, pri čemu je prvi katalizator kiselinski katalizator koji sadrži WO3 podržan na ZrO2.
11. Metoda u skladu s patentnim zahtjevom 1, pri čemu
- navedeni ugljikovodik je etan;
- navedeni prvi katalizator je kiselinski katalizator;
- navedeni drugi katalizator je katalizator koji sadrži Pt na CeO2;
- glicerol je priskrbljen kao smjesa s vodom, kao što je smjesa koja ima koncentraciju glicerola od 15 do 30 wt%;
- temperatura kod koje je glicerol pretvoren u akrolein i akrolein u etan je 250°C do 350°C;
- tlak kod kojeg je glicerol pretvoren u akrolein i akrolein u etan je 3.5 do 4.5 bara;
- temperatura smjese glicerol/voda kada je priskrbljena iznosi 250°C do 350°C; i
- navedeni prvi i navedeni drugi katalizator prisutni su u istom reaktoru.
12. Metoda u skladu s patentnim zahtjevom 11, pri čemu je navedeni prvi katalizator kiselinski katalizator koji sadrži WO3 na ZrO2.
13. Metoda u skladu s patentnim zahtjevom 1 ili 8 do 10, pri čemu je ugljikovodik eten i drugi katalizator je katalizator koji sadrži Pd/CeO2 kao katalizirajući dio.
14. Metoda u skladu s patentnim zahtjevom 1, pri čemu:
glicerol je priskrbljen kao smjesa s vodom u plinovitom stanju, navedena smjesa ima temperaturu od 200 do 400°C;
glicerol je pretvoren u akrolein na temperaturi od 200 do 400°C i kod tlaka od 2 do 10 bara;
metoda nadalje obuhvaća korak priskrbljivanja vodika u stehiometrijskom suvišku u odnosu na glicerol;
ugljikovodik je propan; i
akrolein je pretvoren u propan, uporabom:
drugog katalizatora kataliziranjem reakcije hidrogenacije, navedeni drugi katalizator sadrži Cu na ZnO2, zbog pretvorbe akrolieina u propanol;
trećeg kiselinskog katalizatora kataliziranjem reakcija dehidracije, zbog pretvorbe propanola u propen; i
četvrtog katalizatora kataliziranjem reakcija hidrogenacije, zbog pretvorbe propena u propan.
15. Metoda u skladu s patentnim zahtjevom 14, pri čemu navedeni treći katalizator sadrži WO3 na ZrO2 i navedeni četvrti katalizator je katalizator koji sadrži metal iz grupe platine.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11138808P | 2008-11-05 | 2008-11-05 | |
| SE0850077 | 2008-11-14 | ||
| EP09744163.8A EP2358653B1 (en) | 2008-11-05 | 2009-11-03 | A process for preparing lower hydrocarbons from glycerol |
| PCT/EP2009/064517 WO2010052208A2 (en) | 2008-11-05 | 2009-11-03 | A process for preparing lower hydrocarbons from glycerol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20151101T1 true HRP20151101T1 (hr) | 2015-12-04 |
Family
ID=42125038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20151101TT HRP20151101T1 (hr) | 2008-11-05 | 2015-10-19 | Postupak za pripravu nižih ugljikovodika iz glicerola |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20110224470A1 (hr) |
| EP (1) | EP2358653B1 (hr) |
| CY (1) | CY1117044T1 (hr) |
| DK (1) | DK2358653T3 (hr) |
| ES (1) | ES2550788T3 (hr) |
| HR (1) | HRP20151101T1 (hr) |
| HU (1) | HUE026365T2 (hr) |
| PL (1) | PL2358653T3 (hr) |
| PT (1) | PT2358653E (hr) |
| SI (1) | SI2358653T1 (hr) |
| SM (1) | SMT201500259B (hr) |
| WO (1) | WO2010052208A2 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011076787A1 (en) | 2009-12-23 | 2011-06-30 | Biofuel-Solution Ab | Method for hydrogenating 1,2-unsaturated carbonylic compounds |
| EP2468709A1 (en) | 2010-11-30 | 2012-06-27 | BioFuel-Solution AB | A process for producing acrolein |
| KR101629003B1 (ko) | 2013-11-18 | 2016-06-09 | 주식회사 엘지화학 | 글리세린 탈수반응용 촉매, 이의 제조 방법 및 아크롤레인의 제조 방법 |
| WO2020117119A1 (en) | 2018-12-05 | 2020-06-11 | Biofuel-Solution I Malmö Ab | A process for converting glycerol to propane |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3173959A (en) * | 1965-03-16 | Process for the production of saturated fatty alcohols | ||
| US1895529A (en) * | 1926-06-24 | 1933-01-31 | Du Pont | Process of catalytic dehydration |
| US2139351A (en) * | 1937-09-18 | 1938-12-06 | Shell Dev | Temperature control process and apparatus |
| US3113986A (en) * | 1962-01-08 | 1963-12-10 | Hercules Powder Co Ltd | Hydrogenation of unsaturated hydrocarbons |
| US3501546A (en) * | 1968-03-14 | 1970-03-17 | Ethyl Corp | Preparation of paraffinic hydrocarbons from acyclic,monohydric,primary alkanols and aldehydes having up to 24 carbon atoms with a catalyst consisting of palladium dispersed on titanium dioxide |
| US3832392A (en) * | 1970-07-23 | 1974-08-27 | J Imamura | Process for producing perisobutyric acid |
| US4049576A (en) * | 1974-10-04 | 1977-09-20 | Ashland Oil, Inc. | Platinum-palladium catalyst for selective hydrogenation of aromatics and olefins in hydrocarbon fractions |
| US4032458A (en) * | 1975-08-08 | 1977-06-28 | Petro-Tex Chemical Corporation | Production of 1,4-butanediol |
| US4036905A (en) * | 1976-04-12 | 1977-07-19 | Oxirane Corporation | Process for the manufacture of propylene oxide |
| DE2810662C3 (de) * | 1978-03-11 | 1982-03-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Reinigung eines Epoxids oder eines solches enthaltenden Gemisches |
| US4261700A (en) * | 1979-05-07 | 1981-04-14 | Colgate-Palmolive Company | Ignition method with pressure dispensable gelled fuel |
| US5004845A (en) * | 1981-08-20 | 1991-04-02 | Davy Mckee (London) Limited | Hydrogenation of aldehydes |
| GB8430223D0 (en) * | 1984-11-30 | 1985-01-09 | Exxon Research Engineering Co | Hydroformylation of olefins |
| US4973792A (en) * | 1987-07-07 | 1990-11-27 | Uop | Chemical conversion process |
| US4837367A (en) * | 1987-08-03 | 1989-06-06 | Eastman Kodak Company | Low pressure catalytic hydrogenation of carbonyl-containing compounds |
| DE3932332A1 (de) * | 1989-09-28 | 1991-04-11 | Hoechst Ag | Verfahren zur herstellung von alkoholen (einstufig) |
| IT1249955B (it) * | 1991-07-10 | 1995-03-30 | Menon S R L | Procedimento di idrogenazione della glicerina |
| DE4238493C1 (de) * | 1992-11-14 | 1994-04-21 | Degussa | Verfahren zur Herstellung von Acrolein und dessen Verwendung |
| US5865985A (en) * | 1997-02-14 | 1999-02-02 | Akzo Nobel Nv | Process for the production of diesel |
| US5990323A (en) * | 1998-10-23 | 1999-11-23 | Eastman Chemical Company | Preparation of amines |
| WO2002026618A2 (en) * | 2000-09-25 | 2002-04-04 | Engelhard Corporation | Suppression of methanation acitvity by a water gas shift reaction catalyst |
| US7201783B2 (en) * | 2000-11-13 | 2007-04-10 | Idatech, Llc | Fuel processing system and improved feedstock therefor |
| CN1310851C (zh) * | 2002-05-10 | 2007-04-18 | 威斯康星旧生研究基金会 | 由氧化烃低温生产烃 |
| US6960694B2 (en) * | 2003-07-01 | 2005-11-01 | Eastman Chemical Company | Processes for preparing β-hydroxy-ketones and α,β-unsaturated ketones |
| EP1666442A4 (en) * | 2003-09-18 | 2007-05-02 | Sumitomo Chemical Co | PROCESS FOR PRODUCING CUMENE |
| JP4567961B2 (ja) * | 2003-11-27 | 2010-10-27 | 株式会社レボインターナショナル | 油脂からのデイーゼル燃料油製造プロセス |
| US7585339B2 (en) * | 2004-09-15 | 2009-09-08 | Haldor Topsoe A/S | Process for reforming ethanol to hydrogen-rich products |
| US7405337B2 (en) * | 2004-09-21 | 2008-07-29 | Uop Llc | Conversion of oxygenate to propylene with selective hydrogen treatment of heavy olefin recycle stream |
| FR2882052B1 (fr) * | 2005-02-15 | 2007-03-23 | Arkema Sa | Procede de deshydratation du glycerol en acroleine |
-
2009
- 2009-11-03 PT PT97441638T patent/PT2358653E/pt unknown
- 2009-11-03 DK DK09744163.8T patent/DK2358653T3/en active
- 2009-11-03 PL PL09744163T patent/PL2358653T3/pl unknown
- 2009-11-03 HU HUE09744163A patent/HUE026365T2/en unknown
- 2009-11-03 WO PCT/EP2009/064517 patent/WO2010052208A2/en active Application Filing
- 2009-11-03 ES ES09744163.8T patent/ES2550788T3/es active Active
- 2009-11-03 SI SI200931291T patent/SI2358653T1/sl unknown
- 2009-11-03 EP EP09744163.8A patent/EP2358653B1/en not_active Not-in-force
- 2009-11-03 US US13/127,599 patent/US20110224470A1/en not_active Abandoned
-
2015
- 2015-10-19 HR HRP20151101TT patent/HRP20151101T1/hr unknown
- 2015-10-22 CY CY20151100946T patent/CY1117044T1/el unknown
- 2015-10-22 SM SM201500259T patent/SMT201500259B/it unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK2358653T3 (en) | 2015-10-26 |
| WO2010052208A3 (en) | 2010-07-22 |
| PT2358653E (pt) | 2015-11-16 |
| CY1117044T1 (el) | 2017-04-05 |
| US20110224470A1 (en) | 2011-09-15 |
| WO2010052208A2 (en) | 2010-05-14 |
| SI2358653T1 (sl) | 2015-12-31 |
| SMT201500259B (it) | 2016-01-08 |
| ES2550788T3 (es) | 2015-11-12 |
| EP2358653A2 (en) | 2011-08-24 |
| EP2358653B1 (en) | 2015-07-22 |
| PL2358653T3 (pl) | 2016-01-29 |
| HUE026365T2 (en) | 2016-06-28 |
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