NZ553069A - Integrated process for synthesizing alcohols, ethers, and olefins from alkanes using a multi-zone reactor - Google Patents
Integrated process for synthesizing alcohols, ethers, and olefins from alkanes using a multi-zone reactorInfo
- Publication number
- NZ553069A NZ553069A NZ553069A NZ55306905A NZ553069A NZ 553069 A NZ553069 A NZ 553069A NZ 553069 A NZ553069 A NZ 553069A NZ 55306905 A NZ55306905 A NZ 55306905A NZ 553069 A NZ553069 A NZ 553069A
- Authority
- NZ
- New Zealand
- Prior art keywords
- halide
- zone
- providing
- chamber
- reaction
- Prior art date
Links
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 34
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 29
- 150000002170 ethers Chemical class 0.000 title claims abstract description 29
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 27
- 230000008569 process Effects 0.000 title description 8
- 230000002194 synthesizing effect Effects 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 94
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 75
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 74
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 67
- 150000005309 metal halides Chemical class 0.000 claims abstract description 66
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 44
- 150000004820 halides Chemical class 0.000 claims abstract description 40
- 239000000376 reactant Substances 0.000 claims abstract description 31
- 230000001590 oxidative effect Effects 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims abstract description 4
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 239000007789 gas Substances 0.000 claims description 34
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000013529 heat transfer fluid Substances 0.000 claims description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 5
- 230000031709 bromination Effects 0.000 claims description 5
- 238000005893 bromination reaction Methods 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims 2
- 230000008602 contraction Effects 0.000 claims 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 229910000039 hydrogen halide Inorganic materials 0.000 description 24
- 239000012433 hydrogen halide Substances 0.000 description 24
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000010276 construction Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 229910001509 metal bromide Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 229940102396 methyl bromide Drugs 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 230000008439 repair process Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- -1 methane Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 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
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
-
- 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
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- 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
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/894,165 US7230150B2 (en) | 2001-04-18 | 2004-07-19 | Zone reactor |
| PCT/US2005/002829 WO2006019399A2 (en) | 2004-07-19 | 2005-02-02 | Zone reactor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ553069A true NZ553069A (en) | 2010-06-25 |
Family
ID=35907822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ553069A NZ553069A (en) | 2004-07-19 | 2005-02-02 | Integrated process for synthesizing alcohols, ethers, and olefins from alkanes using a multi-zone reactor |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7230150B2 (https=) |
| EP (1) | EP1773736A4 (https=) |
| JP (1) | JP4971154B2 (https=) |
| KR (1) | KR100941359B1 (https=) |
| CN (1) | CN101014556B (https=) |
| AP (1) | AP2429A (https=) |
| AU (1) | AU2005273030C1 (https=) |
| BR (1) | BRPI0513530A (https=) |
| CA (1) | CA2576668C (https=) |
| EA (1) | EA015004B1 (https=) |
| IL (2) | IL180804A (https=) |
| IN (1) | IN2012DN01046A (https=) |
| MX (1) | MX2007000779A (https=) |
| MY (1) | MY144071A (https=) |
| NO (1) | NO20070760L (https=) |
| NZ (1) | NZ553069A (https=) |
| UA (1) | UA87509C2 (https=) |
| WO (1) | WO2006019399A2 (https=) |
| ZA (1) | ZA200701191B (https=) |
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| JP2007525477A (ja) | 2003-07-15 | 2007-09-06 | ジーアールティー インコーポレイテッド | 炭化水素の合成 |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
| US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US20060100469A1 (en) | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
| US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| SG187456A1 (en) | 2006-02-03 | 2013-02-28 | Grt Inc | Separation of light gases from halogens |
| AP2673A (en) | 2006-02-03 | 2013-05-23 | Grt Inc | Continuous process for converting natural gas to liquid hydrocarbons |
| MX2009012581A (es) * | 2007-05-24 | 2010-03-15 | Grt Inc | Reactor de zonas que incorpora captura y liberacion de haluro de hidrogeno reversible. |
| US8282810B2 (en) | 2008-06-13 | 2012-10-09 | Marathon Gtf Technology, Ltd. | Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery |
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| US9272970B2 (en) | 2010-07-09 | 2016-03-01 | Celanese International Corporation | Hydrogenolysis of ethyl acetate in alcohol separation processes |
| US8859827B2 (en) | 2011-11-18 | 2014-10-14 | Celanese International Corporation | Esterifying acetic acid to produce ester feed for hydrogenolysis |
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| US9073816B2 (en) | 2011-04-26 | 2015-07-07 | Celanese International Corporation | Reducing ethyl acetate concentration in recycle streams for ethanol production processes |
| US8592635B2 (en) | 2011-04-26 | 2013-11-26 | Celanese International Corporation | Integrated ethanol production by extracting halides from acetic acid |
| WO2012149137A1 (en) | 2011-04-26 | 2012-11-01 | Celanese International Corporation | Process for the production of ethanol from an acetic acid feed and a recycled ethyl acetate feed |
| US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
| US8829256B2 (en) | 2011-06-30 | 2014-09-09 | Gtc Technology Us, Llc | Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons |
| US8895786B2 (en) | 2011-08-03 | 2014-11-25 | Celanese International Corporation | Processes for increasing alcohol production |
| US8802908B2 (en) | 2011-10-21 | 2014-08-12 | Marathon Gtf Technology, Ltd. | Processes and systems for separate, parallel methane and higher alkanes' bromination |
| US9024089B2 (en) | 2011-11-18 | 2015-05-05 | Celanese International Corporation | Esterification process using extractive separation to produce feed for hydrogenolysis |
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| US8927790B2 (en) | 2011-12-15 | 2015-01-06 | Celanese International Corporation | Multiple vapor feeds for hydrogenation process to produce alcohol |
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| EP2972252B1 (en) | 2013-03-14 | 2023-10-18 | Robert Ernest Troxler | Systems and methods for pavement bulk properties and moisture content measurements using ground penetrating radar |
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-
2004
- 2004-07-19 US US10/894,165 patent/US7230150B2/en not_active Expired - Fee Related
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2005
- 2005-02-02 AU AU2005273030A patent/AU2005273030C1/en not_active Ceased
- 2005-02-02 EP EP05712315A patent/EP1773736A4/en not_active Withdrawn
- 2005-02-02 WO PCT/US2005/002829 patent/WO2006019399A2/en not_active Ceased
- 2005-02-02 KR KR1020077003851A patent/KR100941359B1/ko not_active Expired - Fee Related
- 2005-02-02 UA UAA200701725A patent/UA87509C2/ru unknown
- 2005-02-02 JP JP2007522482A patent/JP4971154B2/ja not_active Expired - Fee Related
- 2005-02-02 BR BRPI0513530-3A patent/BRPI0513530A/pt active Search and Examination
- 2005-02-02 EA EA200700339A patent/EA015004B1/ru not_active IP Right Cessation
- 2005-02-02 NZ NZ553069A patent/NZ553069A/en not_active IP Right Cessation
- 2005-02-02 AP AP2007003902A patent/AP2429A/xx active
- 2005-02-02 CA CA2576668A patent/CA2576668C/en not_active Expired - Fee Related
- 2005-02-02 ZA ZA200701191A patent/ZA200701191B/xx unknown
- 2005-02-02 IN IN1046DEN2012 patent/IN2012DN01046A/en unknown
- 2005-02-02 MX MX2007000779A patent/MX2007000779A/es active IP Right Grant
- 2005-02-02 CN CN200580029181XA patent/CN101014556B/zh not_active Expired - Fee Related
- 2005-02-22 MY MYPI20050680A patent/MY144071A/en unknown
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2007
- 2007-01-18 IL IL180804A patent/IL180804A/en not_active IP Right Cessation
- 2007-02-08 NO NO20070760A patent/NO20070760L/no not_active Application Discontinuation
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2009
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1773736A2 (en) | 2007-04-18 |
| JP4971154B2 (ja) | 2012-07-11 |
| WO2006019399A2 (en) | 2006-02-23 |
| AU2005273030B2 (en) | 2009-08-13 |
| AP2429A (en) | 2012-08-31 |
| US20040267074A1 (en) | 2004-12-30 |
| IL180804A0 (en) | 2007-06-03 |
| KR20070055502A (ko) | 2007-05-30 |
| EA200700339A1 (ru) | 2007-08-31 |
| UA87509C2 (ru) | 2009-07-27 |
| CA2576668A1 (en) | 2006-02-23 |
| US7230150B2 (en) | 2007-06-12 |
| IL203069A (en) | 2012-12-31 |
| AU2005273030C1 (en) | 2011-10-20 |
| AU2005273030A1 (en) | 2006-02-23 |
| AP2007003902A0 (en) | 2007-02-28 |
| WO2006019399A3 (en) | 2006-11-16 |
| ZA200701191B (en) | 2008-08-27 |
| MX2007000779A (es) | 2007-04-02 |
| IN2012DN01046A (https=) | 2015-04-10 |
| JP2008506775A (ja) | 2008-03-06 |
| EP1773736A4 (en) | 2010-08-11 |
| BRPI0513530A (pt) | 2008-05-06 |
| NO20070760L (no) | 2007-04-19 |
| KR100941359B1 (ko) | 2010-02-11 |
| EA015004B1 (ru) | 2011-04-29 |
| CN101014556A (zh) | 2007-08-08 |
| CN101014556B (zh) | 2012-09-26 |
| IL180804A (en) | 2011-11-30 |
| CA2576668C (en) | 2010-12-21 |
| MY144071A (en) | 2011-08-15 |
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| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |