WO1997040121A1 - Process for removing oxygenated contaminants from hydrocarbon streams - Google Patents
Process for removing oxygenated contaminants from hydrocarbon streams Download PDFInfo
- Publication number
- WO1997040121A1 WO1997040121A1 PCT/EP1997/001994 EP9701994W WO9740121A1 WO 1997040121 A1 WO1997040121 A1 WO 1997040121A1 EP 9701994 W EP9701994 W EP 9701994W WO 9740121 A1 WO9740121 A1 WO 9740121A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- contaminants
- silica gel
- adsorbed
- process according
- oxygenated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 15
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 15
- 239000000356 contaminant Substances 0.000 title claims abstract description 11
- 239000004215 Carbon black (E152) Substances 0.000 title description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000741 silica gel Substances 0.000 claims abstract description 13
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 13
- 238000001179 sorption measurement Methods 0.000 claims abstract description 11
- 238000011069 regeneration method Methods 0.000 claims abstract description 10
- 230000008929 regeneration Effects 0.000 claims abstract description 9
- 239000011261 inert gas Substances 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 239000003463 adsorbent Substances 0.000 claims abstract description 4
- 238000007669 thermal treatment Methods 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003546 flue gas Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000003570 air Substances 0.000 claims description 2
- 239000007792 gaseous phase Substances 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 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
- 238000009835 boiling Methods 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- -1 steam Chemical compound 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
Definitions
- the present invention relates to a process for selectively removing oxygenated contaminants from hydrocarbon streams.
- the oxygenated products present in these cases are the corresponding ter-alkyl alcohols, obtained by the acid-catalyzed addition of water to the iso-olefin and alkyl-teralkyl ethers, generally deriving from impurities in the charge - for example MTBE in C. cuts as it is extremely costly to obtain a C 5 olefin stream without isobutene and also the boiling point of MTBE is very close to that of C 5 hydrocarbons.
- oxygenated products are harmful is in the polymerization of iso-olefins, preferably isobutene with a high purity obtained by the decomposition of the corresponding alkylether, i.e. MTBE. Also in this case the total oxygenated products (methanol, dimethylether, water) must be less than 10 ppm.
- Oxygenated products on the level of impurities, are generally harmful in processes using zeolites owing to their great affinity.
- Competitive adsorptions can in fact arise which reduce the overall efficiency of the process.
- EP-504980 discloses various methods for removing these oxygenated products.
- EP-504980 can be mentioned wherein the teralkyl-alkyl ethers and corresponding alcohols (MTBE, TAME, TBA, TAA) are removed from C 5 streams in the synthesis of TAME by
- a process has been surprisingly found using a material which combines a high adsorbing capacity (molecules retained per unit of the adsorbent mass under conditions of equilibrium) for oxygenated com- pounds and a high adsorption rate of these molecules (molecules adsorbed per unit of time) , also allowing said material to be easily and completely regenerated.
- This latter aspect although not indicated in the art cited above, is of fundamental importance in applying the method on an industrial scale.
- the process for selectively removing oxygenated contaminants from streams prevalently containing hydrocarbons with from 3 to 8 carbon atoms, of the present invention is characterized in that it compris- es an adsorption step wherein said oxygenated compounds are adsorbed with an adsorbent essentially consisting of silica gel, carried out at a temperature of between 0 and 150°C and a pressure of between 1 and 20 atms, and a regeneration step for removing the substances adsorbed by means of thermal treatment in a stream of inert gas, carried out at a temperature of between 100 and 200'C.
- the inert gas used in the thermal treatment can be selected from gases normally used for carrying out regenerations, such as nitrogen, helium, steam, flue gas, air, etc.
- the silica gel used can have a surface area preferably higher than 300 ⁇ a 2 /g , more preferably higher than 400 m 2 /g > and a porous volume preferably of between 0.38 and 1.75 ml/g.
- the oxygenated compounds which can be present in the hydrocarbon streams are preferably C ⁇ C. Q alcohols, alkylethers, symmetrical and mixed, but also occasion ⁇ ally aldehydes and ketones.
- the hydrocarbon streams under consideration can typically contain paraffins, olefins or diolefins, prevalently with from 3 to 8 carbon atoms and do not normally contain more than 10000 ppm of oxygenated compounds. This however does not prevent the process claimed herein to be also used for streams with a much higher content of oxygenated compounds: it will be necessary to suitably dimension the adsorption section.
- commercial silica gel may contain some impurities, such as for example Na + , Ca 2* , Fe 3+ , S0 4 2" and Cl " , at a level of a few hundreds of ppm, or modifiers for specific uses, such as for example Co 2* , or be in the form of a cogel and contain for example Al 3+ , Zr 4+ , Ti A+ , Mg 2+ .
- a very interesting aspect of this material is that it has a moderate acidity under the applicative condi ⁇ tions, which however is not sufficient to cause unde ⁇ sired polymerization or isomerization reactions in the hydrocarbon streams, mainly based on olefins which are to be treated and not sufficient to react with the oxygenated compound, which would make it difficult to regenerate.
- Another peculiar and surprising aspect of this material is that, if a stream is to be treated which contemporaneously contains paraffins and olefins, it does not preferentially adsorb the olefinic component and does not therefore alter the composition of the hydrocarbon stream which is being used.
- a further aspect which is equally important as those already mentioned consists in the capacity of silica gel to selectively adsorb oxygenated compounds from hydrocarbon streams both in gaseous and liquid phases.
- the removal of oxygenated compounds is generally a cyclic operation which involves an adsorption step and a regeneration step of the material (desorption of the oxygenated compound adsorbed) .
- the times for each step of the cycle are strictly correlated to the operating conditions in adsorption phase, such as for example the quantity of oxygenated compound to be removed, the space velocity, the operating pressure and temperature. It can be easily deduced that by increas ⁇ ing the content of the oxygenated compound and the space velocity, the times of the adsorption phase are shortened, as the saturation of the material is more rapidly reached, or by increasing the temperature the adsorbing capacity decreases.
- Silica gel has an adsorption capacity for oxygen ⁇ ated compounds which can even reach 14-15% by weight, if they are in contact with a hydrocarbon stream which contains several thousand ppm.
- silica gel has the capacity of selectively adsorbing oxygenated contami ⁇ nants from hydrocarbon streams in both liquid and gas phase. It is also mechanically and chemically stable under operating conditions and can be easily regenerat ⁇ ed without reducing its efficiency after repeated adsorption-regeneration cycles.
- Exampl e 1 the capacity of selectively adsorbing oxygenated contami ⁇ nants from hydrocarbon streams in both liquid and gas phase. It is also mechanically and chemically stable under operating conditions and can be easily regenerat ⁇ ed without reducing its efficiency after repeated adsorption-regeneration cycles.
- a stream is fed at a pressure of 2.3 atm and WHSV of 6 h "1 to the reactor containing 0.5 g of silica gel at room temperature (20°C) , having the following composition:
- TAME methyl-teramylic ether
- TAA teramylic alcohol
- a stream is fed in the experimental configuration of example 1 at room temperature (20°C) , a pressure of 2.3 atm and WHSV of 10 h '1 , having the following compo ⁇ sition:
- Example 5 A stream is fed in the experimental configuration of example 1 at room temperature (20"C) , a pressure of 2.3 atm and WHSV of 10 h "1 , having the following compo ⁇ sition: Compound Weight 2-methyl-butane 97.84 %
- a stream is fed in the experimental configuration of example 1 at a temperature of 84 °C, a pressure of 6.5 atm and WHSV of 10 h '1 , having the following compo- sition:
- the material coming from example 2 is subjected to regeneration and reaction cycles.
- the regeneration is carried out in a tubular reactor feeding inert gas (He: 10 cc/min) raising the temperature to 140°C in about 1 hour.
- the effluent gases are analyzed by gaschromato- graphy: the regeneration is considered completed when organic compounds are no longer observed in the efflu ⁇ ent.
- the adsorption is repeated under the same operat ⁇ ing conditions as example 2 with the same charge.
- the following table shows the adsorbing capacity of the first seven cycles. It can be seen that the adsorbing capacity remains constant within experimental error.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/147,164 US6111162A (en) | 1996-04-22 | 1997-04-16 | Process for removing oxygenated contaminants from hydrocarbon streams |
| DE19781821T DE19781821T1 (de) | 1996-04-22 | 1997-04-16 | Verfahren zur Entfernung von oxygenierten Verunreinigungen aus Kohlenwasserstoffströmen |
| AU27004/97A AU2700497A (en) | 1996-04-22 | 1997-04-16 | Process for removing oxygenated contaminants from hydrocarbon streams |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI000773A IT1283627B1 (it) | 1996-04-22 | 1996-04-22 | Procedimento per rimuovere contaminanti ossigenati da correnti idrocarburiche |
| ITMI96A000773 | 1996-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997040121A1 true WO1997040121A1 (en) | 1997-10-30 |
Family
ID=11374052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1997/001994 WO1997040121A1 (en) | 1996-04-22 | 1997-04-16 | Process for removing oxygenated contaminants from hydrocarbon streams |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6111162A (enEXAMPLES) |
| AR (1) | AR006784A1 (enEXAMPLES) |
| AU (1) | AU2700497A (enEXAMPLES) |
| CA (1) | CA2252624A1 (enEXAMPLES) |
| DE (1) | DE19781821T1 (enEXAMPLES) |
| IT (1) | IT1283627B1 (enEXAMPLES) |
| WO (1) | WO1997040121A1 (enEXAMPLES) |
| ZA (1) | ZA973243B (enEXAMPLES) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106311133A (zh) * | 2015-06-24 | 2017-01-11 | 中国石油化工股份有限公司 | 固体净化剂及其制备方法 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100308037B1 (ko) * | 1998-12-31 | 2001-11-09 | 구자홍 | 디지털티브이의eit분석방법 |
| JP4070392B2 (ja) * | 2000-08-01 | 2008-04-02 | 富士通株式会社 | フッ素系溶媒の調製方法及び装置ならびに精製方法 |
| MXPA01008582A (es) * | 2001-08-24 | 2003-02-27 | Fians Capital S A De C V | Mejoras en tratamiento para reduccion de azufre en gasolinas cataliticas y en destilados intermedios de crudo, con silica gel. |
| US7102044B1 (en) | 2002-12-12 | 2006-09-05 | Uop Llc | Process for removal of oxygenates from a paraffin stream |
| US7326821B2 (en) * | 2003-06-16 | 2008-02-05 | Exxonmobil Chemical Patents Inc. | Removal of oxygenate from an olefin stream |
| US6987152B1 (en) * | 2005-01-11 | 2006-01-17 | Univation Technologies, Llc | Feed purification at ambient temperature |
| TW200936564A (en) * | 2007-11-15 | 2009-09-01 | Univation Tech Llc | Methods for the removal of impurities from polymerization feed streams |
| WO2013014003A1 (en) * | 2011-07-28 | 2013-01-31 | Total Research & Technology Feluy | Process for removing oxygenated contaminants from an ethylene stream |
| KR20150002714A (ko) | 2012-04-03 | 2015-01-07 | 릴라이언스 인더스트리즈 리미티드 | 함산소물이 없는 c8-c12 방향족 탄화수소 스트림과 그의 제조 공정 |
| CN105339394B (zh) | 2013-06-25 | 2017-06-09 | 埃克森美孚化学专利公司 | 减轻烯烃聚合中的催化剂抑制 |
| US10207249B2 (en) | 2014-12-12 | 2019-02-19 | Exxonmobil Research And Engineering Company | Organosilica materials and uses thereof |
| WO2016094848A1 (en) | 2014-12-12 | 2016-06-16 | Exxonmobil Chemical Patents Inc. | Organosilica materials for use as adsorbents for oxygenate removal |
| WO2016094843A2 (en) | 2014-12-12 | 2016-06-16 | Exxonmobil Chemical Patents Inc. | Olefin polymerization catalyst system comprising mesoporous organosilica support |
| US10183272B2 (en) | 2014-12-12 | 2019-01-22 | Exxonmobil Research And Engineering Company | Adsorbent for heteroatom species removal and uses thereof |
| US10179839B2 (en) | 2016-11-18 | 2019-01-15 | Exxonmobil Research And Engineering Company | Sulfur terminated organosilica materials and uses thereof |
| US10047178B2 (en) | 2017-02-07 | 2018-08-14 | Exxonmobil Chemical Patents Inc. | Mitigation of catalyst inhibition in olefin polymerization |
| CN107338069A (zh) * | 2017-08-11 | 2017-11-10 | 中科合成油技术有限公司 | 一种脱除轻质油中微量有机含氧化合物的方法 |
| CN111051355A (zh) | 2017-08-29 | 2020-04-21 | 埃克森美孚化学专利公司 | 二氧化碳作为溶液聚合中的催化剂淬灭剂和由其制备的产物 |
| CN115505418A (zh) * | 2022-10-21 | 2022-12-23 | 中国石油化工股份有限公司 | 一种异构烷烃中含氧化合物的脱除方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB693967A (en) * | 1949-03-21 | 1953-07-08 | California Research Corp | Methods of separating mixtures of organic liquids by adsorption |
| US2719206A (en) * | 1949-10-24 | 1955-09-27 | Phillips Petroleum Co | Continuous adsorption apparatus |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2653959A (en) * | 1949-03-22 | 1953-09-29 | Texas Co | Process for recovering oxygenated organic compounds |
| US4404118A (en) * | 1981-12-28 | 1983-09-13 | Uop Inc. | Regeneration of adsorbents by low temperature hydrogen stripping |
| US5245107A (en) * | 1991-06-18 | 1993-09-14 | Uop | Liquid phase adsorption process |
| US5466364A (en) * | 1993-07-02 | 1995-11-14 | Exxon Research & Engineering Co. | Performance of contaminated wax isomerate oil and hydrocarbon synthesis liquid products by silica adsorption |
-
1996
- 1996-04-22 IT IT96MI000773A patent/IT1283627B1/it active IP Right Grant
-
1997
- 1997-04-16 DE DE19781821T patent/DE19781821T1/de not_active Withdrawn
- 1997-04-16 AU AU27004/97A patent/AU2700497A/en not_active Abandoned
- 1997-04-16 WO PCT/EP1997/001994 patent/WO1997040121A1/en active Application Filing
- 1997-04-16 ZA ZA9703243A patent/ZA973243B/xx unknown
- 1997-04-16 US US09/147,164 patent/US6111162A/en not_active Expired - Fee Related
- 1997-04-16 CA CA002252624A patent/CA2252624A1/en not_active Abandoned
- 1997-04-22 AR ARP970101620A patent/AR006784A1/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB693967A (en) * | 1949-03-21 | 1953-07-08 | California Research Corp | Methods of separating mixtures of organic liquids by adsorption |
| US2719206A (en) * | 1949-10-24 | 1955-09-27 | Phillips Petroleum Co | Continuous adsorption apparatus |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106311133A (zh) * | 2015-06-24 | 2017-01-11 | 中国石油化工股份有限公司 | 固体净化剂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1283627B1 (it) | 1998-04-22 |
| DE19781821T1 (de) | 1999-07-01 |
| AR006784A1 (es) | 1999-09-29 |
| ITMI960773A1 (it) | 1997-10-22 |
| AU2700497A (en) | 1997-11-12 |
| ZA973243B (en) | 1997-11-20 |
| US6111162A (en) | 2000-08-29 |
| CA2252624A1 (en) | 1997-10-30 |
| ITMI960773A0 (enEXAMPLES) | 1996-04-22 |
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