SU694483A1 - Method of refining halohydrocarbon by-products in production of allyl chloride and methallyl chloride - Google Patents
Method of refining halohydrocarbon by-products in production of allyl chloride and methallyl chlorideInfo
- Publication number
- SU694483A1 SU694483A1 SU782621764A SU2621764A SU694483A1 SU 694483 A1 SU694483 A1 SU 694483A1 SU 782621764 A SU782621764 A SU 782621764A SU 2621764 A SU2621764 A SU 2621764A SU 694483 A1 SU694483 A1 SU 694483A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloride
- products
- production
- halohydrocarbon
- refining
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 15
- 238000004519 manufacturing process Methods 0.000 title description 7
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 title description 5
- 239000006227 byproduct Substances 0.000 title description 5
- 150000005826 halohydrocarbons Chemical class 0.000 title description 3
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 title 1
- 238000007670 refining Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 description 14
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 10
- 239000002994 raw material Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- -1 platinum group metals Chemical class 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical compound CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- PNLQPWWBHXMFCA-UHFFFAOYSA-N 2-chloroprop-1-ene Chemical class CC(Cl)=C PNLQPWWBHXMFCA-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical class [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Chemical class [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изобретение отноеитс к области промышленного нроизводетва нефтехимических продуктов, конкретно к способу утилизации отходов производства хлорорганических продуктов.The invention relates to the field of industrial production of petrochemical products, specifically to the method of disposal of waste production of organochlorine products.
Существующие в насто щее врем производства хлоролефинов и хлоралканов практически не предусматривают возможность квалифицированного использовани образующихс в процессе побочных продуктов , таких как третичный бутилхлорид в производстве металлилхлорида и хлорнропены в производстве хлористого аллила, количество которых составл ет 0,1-0,3 т/т готового продукта. Поэтому такие побочные продукты сжигаютс с образованием хлористого водорода м углекислого газа.The currently existing production of chlorolefins and chloroalkanes practically do not provide for the qualified use of the by-products formed during the process, such as tertiary butyl chloride in the production of metal chloride and chlornropenes in the production of allyl chloride, the amount of which is 0.1-0.3 t / t product. Therefore, such by-products are burned to form hydrogen chloride and carbon dioxide.
Учитыва все возрастающий дефицит углеводородного сырь , переработка крупнотоннажных отходов хлорорганических продуктов в углекислоту представл етс крайне нерациональной, поскольку св зана с потерей углеводородной части отходов.Taking into account the growing shortage of hydrocarbon raw materials, the processing of large-tonnage organochlorine wastes into carbon dioxide is highly inefficient, since it is associated with the loss of the hydrocarbon portion of the waste.
Известен способ переработки побочных продуктов производства галоидуглеводородов , содержащих 2 атомов хлора, путем их восстановлени в газовой фазе в присутствии катализаторов гидрировани 1.A method of processing by-products of the production of halocarbons containing 2 chlorine atoms is known, by reducing them in the gas phase in the presence of hydrogenation catalysts 1.
Процесс провод т при 150-160° С. В качестве катализаторов используют 0,1-The process is carried out at 150-160 ° C. As catalysts, 0.1-
5 вес. % металлов группы платины, нанесенных на окись алюмнни или окись железа , или окись хрома, или активированный уголь.5 wt. % of platinum group metals deposited on aluminum oxide or iron oxide, or chromium oxide, or activated carbon.
Известен также способ переработки галоидуглеподородов , таких как дихлорпропан в пропан и пропилеи, дихлорбутен в бутан, хлорбензол в циклогексан, путем пидрирован1 при 50-500° С в присутствии катализаторов на основе роди 2.There is also known a method for processing halocarbons, such as dichloropropane in propane and propylene, dichlorobutene in butane, chlorobenzene in cyclohexane, by fermentation1 at 50-500 ° C in the presence of rhodium-2 based catalysts.
Кроме роди , катализатор содержит палладий, платину, рутений, железо, кобальт , никель, медь, золото, ванадий, хром, молибден, вольфрам и добавки гидроокисей НЛП карбонатов щелочных или щелочноземельных металлов и/или солей -или окислов алюмини , бора или титана.In addition to rhodium, the catalyst contains palladium, platinum, ruthenium, iron, cobalt, nickel, copper, gold, vanadium, chromium, molybdenum, tungsten and additives of NLP hydroxides of alkali or alkaline earth metals and / or salts of aluminum, boron or titanium oxides.
Иедостатком указанных способов вл етс использование катализаторов на основе дорогосто щих и дефицитных благородных металов.The disadvantage of these methods is the use of catalysts based on expensive and scarce precious metals.
Способ переработки побочных галоидуглеводородов производства хлористого аллила и металлилхлорида, таких как третичный бути тхлорид ,и хлорпропан в литературе не описаи.A method for processing side halohydrocarbons produced by allyl chloride and methyl chloride, such as tertiary buty thichloride, and chloropropane are not described in the literature.
Цель изобретени - разработка способа переработки побочных галоидуглеводородов производства хлористого аллила и м ета л л и л хлор и д а.The purpose of the invention is to develop a method for processing side halohydrocarbons to produce allyl chloride and methanol and chlorine and d.
Поставленна цель достигаетс описываемым способом переработки побочных галюидуглеводородов производства хлористого аллила ,н металлилхлорида путем гидрировапи при 160-285° С в присутствии катализатора - алюмож лезного коптакта, содержащего 10-20 вес. % оксида железа и 80-90 вес. % окиси алюмини .This goal is achieved by the described method of processing side-halyid hydrocarbons produced by allyl chloride and metal chloride by hydrogenation at 160–285 ° C in the presence of a catalyst — an aluminum alloy containing 10–20 wt. % iron oxide and 80-90 weight. % alumina.
Используемый в описываемом способе катализатор получают совместным осаждением солей алюмини и железа с последуюш им формованием, сушкой и прокалкой при 800° С в течение 3 ч. Готовый катализатор содержит от 10 до 20 вес. % оксидов железа н 80-90 вес. % окиси алюмини .The catalyst used in the described method is obtained by the joint precipitation of aluminum and iron salts, followed by molding, drying and calcining at 800 ° C for 3 hours. The finished catalyst contains from 10 to 20 weight. % iron oxide n 80-90 weight. % alumina.
Процесс провод т на установке проточного типа ео стационарным слоем катализатора массой 15 г при 160-285° С, скорости подачи сырь 0,5-1,0 г/г ч.The process is carried out on a flow-type plant eo with a stationary catalyst bed weighing 15 g at 160-285 ° C, feed rates of 0.5-1.0 g / g h.
Сырье подают шприцевым дозатором в смеситель, куда поступает водород. Смесь исходных продуктов после смесител поступает в реактор. Реакционную массу охлаждают дл конденсации и анализируют хроматограф ическнм методом.Raw materials are fed with a syringe dispenser to a mixer where hydrogen is fed. The mixture of initial products after the mixer enters the reactor. The reaction mass is cooled for condensation and the chromatograph is analyzed by a chemical method.
Пример 1. Сырье - 1- и 2-хлорпропены .Example 1. Raw materials - 1- and 2-chloropropenes.
Катализатор - 10 вес. % окиси железа, 90 вес. % окиси алюмини .Catalyst - 10 wt. % iron oxide, 90 wt. % alumina.
Услови опыта: катализатор 15 г, температура 285° С, мольный избыток водорода 1,5; скорость подачи сырь . 0,8 г/г ч; пропущено сырь за 2 ч 24 г. Результаты опытов. Получено продуктов реакции 23,4 г; конверси сырь 96 мае. %; содержание углеводородов (пропан + иропилен) в продуктах реакции без НС1 99,5 мае. %.Test conditions: catalyst 15 g, temperature 285 ° С, molar excess of hydrogen 1.5; feed rate 0.8 g / g h; missing raw materials for 2 h 24 g. The results of the experiments. The obtained reaction products 23.4 g; raw materials conversion 96 May. %; hydrocarbon content (propane + propylene) in the reaction products without HC1 99.5 May. %
Пример 2. Сырье - третичный бутилхлорид . Катализатор - 20 вес. % окиси железа, 80 вес. % окиои алюмини .Example 2. Raw materials - tertiary butyl chloride. Catalyst - 20 wt. % iron oxide, 80 wt. % aluminum oxide.
Услови опыта: масса катализатора 15 г; температура 160° С, мольный избыток кислорода 0,7; скорость подачи сырь 0,5 г/г ч; нропущеио сырь за 2 ч 15 г. Test conditions: catalyst weight 15 g; temperature 160 ° C, molar excess oxygen of 0.7; feed rate of 0.5 g / g; Unsuspected raw materials for 2 hours and 15 g.
Результаты опытов. Получено продуктовThe results of the experiments. Products received
реакции 14,7 г; конверси сырь 98 мае. %;reactions of 14.7 g; raw material conversion 98 May. %;
содержание углеводородов (изобутилен,hydrocarbon content (isobutylene,
изобутан) в продуктах реакции без НС1isobutane) in the reaction products without HC1
99,1 мае. %.99.1 May. %
Таким образом, иро;длагаемый способ позвол ет квалифицированно использовать побочные продукты производства хлорорга}1ических соединений нутем регенерации углеводородной части отходов в углеводороды (изобутилен, изобутан, иропан, нроиилен ), которые могут быть вновь использованы в процессах нефтехимического синтеза . При этом исключаетс использование дорогосто щих катализаторов гидрировани на основе благородных металлов.Thus, the advanced method allows qualified use of the by-products of the production of chlorine} 1ic compounds by regenerating the hydrocarbon portion of the waste into hydrocarbons (isobutylene, isobutane, propane, niroiylene), which can be reused in petrochemical synthesis processes. This eliminates the use of expensive hydrogenation catalysts based on noble metals.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782621764A SU694483A1 (en) | 1978-05-22 | 1978-05-22 | Method of refining halohydrocarbon by-products in production of allyl chloride and methallyl chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782621764A SU694483A1 (en) | 1978-05-22 | 1978-05-22 | Method of refining halohydrocarbon by-products in production of allyl chloride and methallyl chloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU694483A1 true SU694483A1 (en) | 1979-10-30 |
Family
ID=20767235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782621764A SU694483A1 (en) | 1978-05-22 | 1978-05-22 | Method of refining halohydrocarbon by-products in production of allyl chloride and methallyl chloride |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU694483A1 (en) |
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| US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US8198495B2 (en) | 2010-03-02 | 2012-06-12 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
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| US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
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