EP0000279A1 - A process for removing organic carbonyl-containing contaminants from a hydrocarbon product stream - Google Patents
A process for removing organic carbonyl-containing contaminants from a hydrocarbon product stream Download PDFInfo
- Publication number
- EP0000279A1 EP0000279A1 EP78300092A EP78300092A EP0000279A1 EP 0000279 A1 EP0000279 A1 EP 0000279A1 EP 78300092 A EP78300092 A EP 78300092A EP 78300092 A EP78300092 A EP 78300092A EP 0000279 A1 EP0000279 A1 EP 0000279A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- process according
- hydrocarbon product
- organic
- carbonyl
- interface
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/949—Miscellaneous considerations
- Y10S585/956—Condition-responsive control and related procedures in alicyclic synthesis and purification
Definitions
- This invention relates to a process for the removal of carbonyl-containing contaminants from hydrocarbon product streams.
- the invention is particularly useful in the purification of butadiene, an important industrial chemical used in the manufacture of synthetic rubber, latex paints, and nylon and in the Diels-Alder condensation for the synthesis of many diverse compounds.
- butadiene small amounts of carbonyl-containing impurities (e.g., acetaldehyde) are produced and it is important that these impurities be removed or they will have an adverse effect on subsequent processes in which the butadiene is a raw material.
- the carbonyl content of the butadiene product stream is low (being typically measured in parts per millon), the heretofore used procedures for reducing it to an acceptable level have been undesirably elaborate and expensive.
- a process for removing organic carbonyl-containing impurities from a hydrocarbon product stream comprises passing that stream, together with an aqueous solution containing an excess (with respect to said impurities) of a reducing agent capable of forming a water-soluble adiaet with carbonyl compounds, to an in-line mixer, passing the resulting mixture to a separation zone in which organic and aqueous phases separate, and withdrawing the organic phase from the separation zone.
- a second separation zone there is employed a second separation zone, simultaneously or in alternation with the first.
- the lower portion of either or both zones may contain column-packing elements designed to enhance contact between the two phases introduced as mixture thereinto.
- the position of the interface between the phases in a separation zone is maintained between predetermined units by withdrawal of a phase from a separation zone in response to a signal generated by movement of the interface.
- the invention thus encompasses a process arrangement wherein a continuous stream of such organic hydrocarbon product, bearing the undesired carbonyl-containing compounds, is contacted with an aqueous solution comprising a reducing agent (e.g., sodium bisulfite) suitable for forming on contact a water soluble reaction product with such carbonyl compounds, such reducing agent being in greater, preferably just slightly greater, concentration than the theoretical stoichiometric ratio for reaction of all of the carbonyl in the organic product.
- a reducing agent e.g., sodium bisulfite
- an excess of such reducing agent e.g., sodium bisulfite
- R is alkyl, alkylene, aryl, aralkyl, etc.
- R' is the same as R or is hydrogen, hydroxy, or ester.
- the aqueous solution of the reducing agent and the organic product stream are passed through an in-line mixing zone where they are well mixed.
- the mixture is then introduced into a phase separating zone where a separation of the aqueous and arganid phase occurs.
- the organic is displaced by the derent water solution already in the separator, the arganic material traveling in upward direction until it crpsses the interface between the two phases.
- the product is once agair contacted with water solution as it migrates pard the interface or, optionally, by means of ternal tower packing.
- the "scrubbed" product continues to rise in the separator and, as overhead from the separator, may be passed to an optional second scrubber which acts as a back-up system in case of surge conditions or maintenance of the first system.
- the aqueous layer, containing the absorbed carbonyl-bearing compound, is removed at the bottom of the phase separator by means of an interface level control means.
- This stream is then fed to a flash pot at the cooling tower and dropped to atmospheric pressure. Any volatile organic material remaining in the stream will flash to vapor form and be removed.
- the wash water then passes to appropriate disposal means.
- FIGURE depicts a flow sheet of a typical process configuration in accord with the invention.
- a continuous stream of organic material in specific embodiment being butadiene in mixture with undesired carbonyl-bearing organic compounds, is supplied directly from production means 1.
- the organic stream is sent to valve 9 where it is routed either to SYSTEM A via conduit 9a, to SYSTEM B via conduit 9b, or is split, some of it being sent to each system to increase through-put of the overall operation.
- aqueous scrubbing solution is prepared in mixing vat 5 where reducing agent 3 (e.g. sodium bisulfite) is dissolved in water to a conventient concentration.
- reducing agent 3 e.g. sodium bisulfite
- This primary or concentrated scrubbing solution is then pumped out of vat 5 and, if dilution to a lower concentration is necessary, is sent via injection pump 6 to mixing pump 7 where it is diluted to a predetermined concentration of reducing agent by mixing with make-up water 2 and brought to the same pressure as the hydrocrbon product stream from production means 1.
- the scrubbing solution which is now at the same pressure as the hydrocarbon product and has a concentration of reducing agent which is 10% to 20% higher than the stoichiometric concentration theoretically required for complete reaction with the carbonyl compounds in the hydrocarbon product, is pumped to valve 8 which directs it to SYSTEM A via conduit 8a or to SYSTEM B via conduit 8b or which splits the stream and sends part of it to each system for simultaneous operation.
- phase separator 11 may optionally contain in its lower section a quantity of internal packing material 12 through which the organic/aqueous mixture is percolated while the phases are separating or, alternatively, the separator 11 may be empty and the phases allowed to separate with additional percolation.
- internal packing material 12 There are many column packing materials which are suitable for this application, a few non-limiting examples being Berl saddles, Intalox saddles and Raschig rings.
- the organic/aqueous mixture from in-line mixing means 10 is introduced into the lower portion of p ⁇ :ase separator 11.
- the organic phase is displaced by the denser aqueous solution.
- the "scrubbed" organic phase being of lesser density than the aqueous solution, travels up the phase separator 11 until it croses the interface 13 between the two 11 until it reaches 13, the organie product is once again contcted with aqueous solution, such recontact being aided by percolation through packing 12 if such packing is employed.
- the "serubbec" product having now had the major portion of the carbonyl-bearing contaminant removed, continues to travel up the tower and is taken off overhead at outlet means 14.
- Interface level control 15 may be any conventional device for detecting the location of interface 13 between the upper organic phase and the lower aqueous phase.
- Control 15 is adpated to operate valve 16 such that when the aqueous level in phase separator 11 increases to the point where interface 13 reaches some predetermined level 15a, the valve 16 is opened and separated aqueous solution is drained out of the bottom of separator 11 through drain line 17.
- level control 15 causes valve 16 to be closed.
- the control be of a type which will continuously regulate the degreee of openness relative to the position of interface 13, i.e.
- valve 16 be partially open at all times so that there is continuous removal of aqueous phase through drain line 17 at a rate equal to or less than the rate of addition of aqueous phase via conduit 8a.
- interface level control 15 would serve as a precautionary safety factor should aqueous material enter the phase separator at a which is faster or slower than the expected rate.
- suitable control devices would include any conventional interface controller useful for normal service applications.
- the in-line mixing means 10 is also of conventional type suitable for admitting two or more streams of unlike materials and continuously mixing. tnem to form a single relatively homogeneous stream.
- An example of such mixing means would be the KOCH ENGINEERING STATIC MIXER.
- aqueous wash solution removed through drain line 17 is taken via conduit 18 to a suitable in-plant wash water disposal means where it is brought to atmospheric pressure, and any absorbed organic material is volatilized.
- the organic vapors are then either collected and recovered or are sent to suitable dieposal means, such as a flare where they are burned.
- suitable dieposal means such as a flare where they are burned.
- the wash water, containing the reaction products of the carbonyl compounds with the reducing agent and any arcess reducing agent, is likewise appropriately disposed of.
- the cleaned-up product removed overhead from phase separator 11 at outlet 14 is routed to valve 19 from whence it may take one of two directions. If the cerbonyl content is sufficiently reduced and the ceueous phase completely or substantially completely separated, the organic stream is sent through conduit 39 to storage facilities where it is held until required for shipment or subsequent synthetic arocesses, or it may sent directly to such subsequent processing as deemed necessary. If further scrubbing
- SYSTEM B is substantially identical to A and serves various purposes. It can be used as a back-up to SYSTEM A in the event of inomplete puhase separation therein or the need for further reduction in the carbonyl content of the scrubbed product, or it can serve as a substitute for SYSTEM A to allow for maintenance of that system.
- acetaldehyde is supplied in a continuous stream from conventional production facilities. Such a stream, at a pressure of 150 psia and a temperature of 29°-32°C (85-90°F), enters the system as illustrated in the drawing.
- Aqueous scrubbing solution containingf 4-5 wt. % sodium bisulfite, is pumped from vat 5 to pump 7, where it is diluted to 700-900 ppm sodium bisulfite with additional water. This dilute scrubbing solution is then pumped to SYSTEM A at a pressure of 120 psia and ambient temperature.
- the two streams are blended in the in-line KOCH STATIC MIXER 10, in proportions resulting in a mixture having a mole ratio of reducing agent to carbonyl compound of 1.1:1 to 1.2:1, and the mixture fed into the lower portion of the phase separator 11 where the organic and aqueous phases are separated (without the use of the optional packing 12) at 125 psia and 27°C (80°F).
- the resulting "scrubbed" butadiene product is taken off overhead via outlet 14 from the phase separator and has a carbonyl content (as acetaldehyde) of ⁇ 2 ppm. It is then sent directly to the normal storage facilities to await appropriate disposition.
- the used wash water is drained from the bottom of the phase separator 11 by means of a drain valve 16, controlled by conventional level control device 15, fed to a flash pot and dropped to atmospheric pressure. Any volatile organic material in the water solution is flashed off and fed to a plant flare system to be burned or is otherwise disposed of.
- the water is pumped into a cooling tower basin.
Abstract
Description
- This invention relates to a process for the removal of carbonyl-containing contaminants from hydrocarbon product streams.
- The invention is particularly useful in the purification of butadiene, an important industrial chemical used in the manufacture of synthetic rubber, latex paints, and nylon and in the Diels-Alder condensation for the synthesis of many diverse compounds. In the synthesis of butadiene, small amounts of carbonyl-containing impurities (e.g., acetaldehyde) are produced and it is important that these impurities be removed or they will have an adverse effect on subsequent processes in which the butadiene is a raw material. Although the carbonyl content of the butadiene product stream is low (being typically measured in parts per millon), the heretofore used procedures for reducing it to an acceptable level have been undesirably elaborate and expensive.
-
- We have now discovered a continuous process for such carbonyl removal which is simple, reliable and relatively inexpensive; and which effects the removal in a single step, permitting the treated product stream to proceed directly to storage or subsequent processing.
- According to the present invention a process for removing organic carbonyl-containing impurities from a hydrocarbon product stream comprises passing that stream, together with an aqueous solution containing an excess (with respect to said impurities) of a reducing agent capable of forming a water-soluble adiaet with carbonyl compounds, to an in-line mixer, passing the resulting mixture to a separation zone in which organic and aqueous phases separate, and withdrawing the organic phase from the separation zone.
-
- In a particular embodiment of the invention there is employed a second separation zone, simultaneously or in alternation with the first. The lower portion of either or both zones may contain column-packing elements designed to enhance contact between the two phases introduced as mixture thereinto. Advantageously, the position of the interface between the phases in a separation zone is maintained between predetermined units by withdrawal of a phase from a separation zone in response to a signal generated by movement of the interface.
- The invention thus encompasses a process arrangement wherein a continuous stream of such organic hydrocarbon product, bearing the undesired carbonyl-containing compounds, is contacted with an aqueous solution comprising a reducing agent (e.g., sodium bisulfite) suitable for forming on contact a water soluble reaction product with such carbonyl compounds, such reducing agent being in greater, preferably just slightly greater, concentration than the theoretical stoichiometric ratio for reaction of all of the carbonyl in the organic product. For example, an excess of such reducing agent (e.g., sodium bisulfite) will tend to drive the following equilibrium equations to the right:
- To insure good contact in the continuous process as emobied herein, the aqueous solution of the reducing agent and the organic product stream are passed through an in-line mixing zone where they are well mixed. The mixture is then introduced into a phase separating zone where a separation of the aqueous and arganid phase occurs. The organic is displaced by the derent water solution already in the separator, the arganic material traveling in upward direction until it crpsses the interface between the two phases. From the part of antry the interface, the product is once agair contacted with water solution as it migrates pard the interface or, optionally, by means of ternal tower packing. The "scrubbed" product continues to rise in the separator and, as overhead from the separator, may be passed to an optional second scrubber which acts as a back-up system in case of surge conditions or maintenance of the first system.
- The aqueous layer, containing the absorbed carbonyl-bearing compound, is removed at the bottom of the phase separator by means of an interface level control means. This stream is then fed to a flash pot at the cooling tower and dropped to atmospheric pressure. Any volatile organic material remaining in the stream will flash to vapor form and be removed. The wash water then passes to appropriate disposal means.
- Understanding of the invention disclosed herein will be facilitated by reference to the single drawing FIGURE, which depicts a flow sheet of a typical process configuration in accord with the invention.
- Referring to the Figure, a continuous stream of organic material, in specific embodiment being butadiene in mixture with undesired carbonyl-bearing organic compounds, is supplied directly from production means 1. The organic stream is sent to valve 9 where it is routed either to SYSTEM A via conduit 9a, to SYSTEM B via
conduit 9b, or is split, some of it being sent to each system to increase through-put of the overall operation. - The aqueous scrubbing solution is prepared in mixing vat 5 where reducing agent 3 (e.g. sodium bisulfite) is dissolved in water to a conventient concentration. This primary or concentrated scrubbing solution is then pumped out of vat 5 and, if dilution to a lower concentration is necessary, is sent via injection pump 6 to mixing pump 7 where it is diluted to a predetermined concentration of reducing agent by mixing with make-up water 2 and brought to the same pressure as the hydrocrbon product stream from production means 1. The scrubbing solution, which is now at the same pressure as the hydrocarbon product and has a concentration of reducing agent which is 10% to 20% higher than the stoichiometric concentration theoretically required for complete reaction with the carbonyl compounds in the hydrocarbon product, is pumped to valve 8 which directs it to SYSTEM A via conduit 8a or to SYSTEM B via
conduit 8b or which splits the stream and sends part of it to each system for simultaneous operation. -
- organic phase and a drain line 17 at the bottom portion for removal of the aqueous phase. Flow of the aqueous phase through drain line 17 is controlled by
valve 16, which in turn is operated remotely by interface level control means 15. The phase separator 11 may optionally contain in its lower section a quantity ofinternal packing material 12 through which the organic/aqueous mixture is percolated while the phases are separating or, alternatively, the separator 11 may be empty and the phases allowed to separate with additional percolation. There are many column packing materials which are suitable for this application, a few non-limiting examples being Berl saddles, Intalox saddles and Raschig rings. - The organic/aqueous mixture from in-line mixing means 10 is introduced into the lower portion of p`:ase separator 11. As the organic and aqueous phases in separator 11 begin to separate, the organic phase is displaced by the denser aqueous solution. The "scrubbed" organic phase, being of lesser density than the aqueous solution, travels up the phase separator 11 until it croses the
interface 13 between the two 11 until it reaches 13, the organie product is once again contcted with aqueous solution, such recontact being aided by percolation through packing 12 if such packing is employed. The "serubbec" product, having now had the major portion of the carbonyl-bearing contaminant removed, continues to travel up the tower and is taken off overhead at outlet means 14. -
Interface level control 15 may be any conventional device for detecting the location ofinterface 13 between the upper organic phase and the lower aqueous phase.Control 15 is adpated to operatevalve 16 such that when the aqueous level in phase separator 11 increases to the point whereinterface 13 reaches somepredetermined level 15a, thevalve 16 is opened and separated aqueous solution is drained out of the bottom of separator 11 through drain line 17. When the level of the aqueous phase has been reduced such thatinterface 13 reaches predeterminedlevel 15b,level control 15 causesvalve 16 to be closed. In practice it may be preferable that, instead oflevel control 15 merely causingvalve 16 to be either open or closed, the control be of a type which will continuously regulate the degreee of openness relative to the position ofinterface 13, i.e. thenearer interface 13 is to level 15a the more fullyopen valve 16 becomes, and thenearer interface 13 is to level 15b the more closed (relatively)valve 16. In some instances, it is desirable thatvalve 16 be partially open at all times so that there is continuous removal of aqueous phase through drain line 17 at a rate equal to or less than the rate of addition of aqueous phase via conduit 8a. In the latter case,interface level control 15 would serve as a precautionary safety factor should aqueous material enter the phase separator at a which is faster or slower than the expected rate. Examples of suitable control devices would include any conventional interface controller useful for normal service applications. - The in-line mixing means 10 is also of conventional type suitable for admitting two or more streams of unlike materials and continuously mixing. tnem to form a single relatively homogeneous stream. An example of such mixing means would be the KOCH ENGINEERING STATIC MIXER.
- The aqueous wash solution removed through drain line 17 is taken via conduit 18 to a suitable in-plant wash water disposal means where it is brought to atmospheric pressure, and any absorbed organic material is volatilized. The organic vapors are then either collected and recovered or are sent to suitable dieposal means, such as a flare where they are burned. The wash water, containing the reaction products of the carbonyl compounds with the reducing agent and any arcess reducing agent, is likewise appropriately disposed of.
- The cleaned-up product removed overhead from phase separator 11 at
outlet 14 is routed tovalve 19 from whence it may take one of two directions. If the cerbonyl content is sufficiently reduced and the ceueous phase completely or substantially completely separated, the organic stream is sent through conduit 39 to storage facilities where it is held until required for shipment or subsequent synthetic arocesses, or it may sent directly to such subsequent processing as deemed necessary. If further scrubbing - SYSTEM B is substantially identical to A and serves various purposes. It can be used as a back-up to SYSTEM A in the event of inomplete puhase separation therein or the need for further reduction in the carbonyl content of the scrubbed product, or it can serve as a substitute for SYSTEM A to allow for maintenance of that system.
- In the event of surge conditions in SYSTEM A, as might result from a sudden and substantial ineresse in product input or failure of the
interface level control 15 and/ordrain valve 16 to function properly, thereby causing imcomplete phase separation such that the overhead stream being removed atoutlet 14 undesirably contains aqueous material as well as organic material, the overhead stream is redireored by means ofvalve 19 throughline 9b and intophase separator 21 where separation and removal of the aqueous phase takes place. The scruobed organic phase is then taken off atoutlet 24 and sent throughdondnre 28 to the appropriate storage facilitias. -
-
- Aqueous scrubbing solution, containingf 4-5 wt. % sodium bisulfite, is pumped from vat 5 to pump 7, where it is diluted to 700-900 ppm sodium bisulfite with additional water. This dilute scrubbing solution is then pumped to SYSTEM A at a pressure of 120 psia and ambient temperature.
- The two streams are blended in the in-line KOCH
STATIC MIXER 10, in proportions resulting in a mixture having a mole ratio of reducing agent to carbonyl compound of 1.1:1 to 1.2:1, and the mixture fed into the lower portion of the phase separator 11 where the organic and aqueous phases are separated (without the use of the optional packing 12) at 125 psia and 27°C (80°F). - The resulting "scrubbed" butadiene product is taken off overhead via
outlet 14 from the phase separator and has a carbonyl content (as acetaldehyde) of <2 ppm. It is then sent directly to the normal storage facilities to await appropriate disposition. - The used wash water is drained from the bottom of the phase separator 11 by means of a
drain valve 16, controlled by conventionallevel control device 15, fed to a flash pot and dropped to atmospheric pressure. Any volatile organic material in the water solution is flashed off and fed to a plant flare system to be burned or is otherwise disposed of. The water is pumped into a cooling tower basin.
Claims (7)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US811106 | 1977-06-29 | ||
US05/811,106 US4125568A (en) | 1977-06-29 | 1977-06-29 | Removal of carbonyl impurities |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000279A1 true EP0000279A1 (en) | 1979-01-10 |
EP0000279B1 EP0000279B1 (en) | 1981-10-14 |
Family
ID=25205578
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78300092A Expired EP0000279B1 (en) | 1977-06-29 | 1978-06-27 | A process for removing organic carbonyl-containing contaminants from a hydrocarbon product stream |
Country Status (8)
Country | Link |
---|---|
US (1) | US4125568A (en) |
EP (1) | EP0000279B1 (en) |
JP (1) | JPS5416411A (en) |
AU (1) | AU517812B2 (en) |
BR (1) | BR7804112A (en) |
CA (1) | CA1099749A (en) |
DE (1) | DE2861153D1 (en) |
IT (1) | IT1097351B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2215344A (en) * | 1988-02-29 | 1989-09-20 | Shell Int Research | A process for purification of alkenyl aromatic coompounds |
EP0534094A2 (en) * | 1991-09-23 | 1993-03-31 | Occidental Chemical Corporation | Process for removing aldehydes and/or vinyl esters from gaseous or liquid process streams |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5333767A (en) * | 1992-03-30 | 1994-08-02 | Anderson Steven P | Wrist mounted magnetic holder |
US5220104A (en) * | 1992-06-15 | 1993-06-15 | Betz Laboratories, Inc. | Method for the prevention of fouling in a caustic solution |
JP3587473B2 (en) * | 1994-06-23 | 2004-11-10 | 日本合成化学工業株式会社 | Purification method of valproic acid |
US6037516A (en) * | 1997-11-20 | 2000-03-14 | Huntsman Ici Chemicals Llc | Method for removal of oxygenate impurities from organic chemical streams |
DE102005036040A1 (en) | 2004-08-28 | 2006-03-02 | Oxeno Olefinchemie Gmbh | Process for the telomerization of non-cyclic olefins |
JP4327239B2 (en) * | 2006-04-17 | 2009-09-09 | 旭化成ケミカルズ株式会社 | Method for producing α-methylstyrene, and method for producing heat-resistant styrene copolymer using the α-methylstyrene |
GB0613676D0 (en) * | 2006-07-10 | 2006-08-16 | Ineos Europe Ltd | Process |
EP2014743A1 (en) * | 2007-06-25 | 2009-01-14 | Ineos Europe Limited | Autothermal cracking process for producing olefins |
DE102008043344A1 (en) | 2008-10-31 | 2010-05-06 | Evonik Oxeno Gmbh | Preparing 1-alkoxy-2,7-diene, useful as starting material in synthesis of e.g. 1-octanol, comprises reacting 1,3-butadiene or 1,3-butadiene containing hydrocarbon mixture with alcohol or its mixture using palladium-carbene complex catalyst |
US20150005552A1 (en) * | 2013-06-26 | 2015-01-01 | Uop Llc | Crude Butadiene Pre-Treatment for Removal of High Furan Content |
US9834498B2 (en) | 2015-08-20 | 2017-12-05 | Janus Technology Solutions, LLC | Removal of carbonyls from gaseous hydrocarbon streams |
US10322986B2 (en) | 2015-11-17 | 2019-06-18 | Janus Technology Solutions, LLC | Removal of carbonyls from liquid phase hydrocarbon streams |
JP6893806B2 (en) * | 2017-03-15 | 2021-06-23 | 旭化成株式会社 | Butadiene production method |
WO2020112328A1 (en) * | 2018-11-30 | 2020-06-04 | Lyondell Chemical Technology, L.P. | Methods of removing carbonyl-containing organic compounds |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE667268A (en) * | 1964-07-29 | 1966-01-24 | ||
US3674887A (en) * | 1970-12-24 | 1972-07-04 | Phillips Petroleum Co | Oxidative dehydrogenation process |
US3682779A (en) * | 1969-09-19 | 1972-08-08 | Phillips Petroleum Co | Removal of carbonyl compounds,residual oxygen and other impurities from hydrocarbon dehydrogenation effluent |
FR2170193A1 (en) * | 1972-02-03 | 1973-09-14 | Petro Tex Chem Corp | |
US3801669A (en) * | 1972-02-03 | 1974-04-02 | Petro Tex Chem Corp | Purification of hydrocarbons |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3536775A (en) * | 1969-06-02 | 1970-10-27 | Phillips Petroleum Co | Removal of oxygen and oxygenated compounds from unsaturated hydrocarbons |
US3804911A (en) * | 1971-07-09 | 1974-04-16 | A Liakumovich | Method of decontaminating hydrocarbons used as solvents and monomers in production of synthetic rubber |
US3842137A (en) * | 1973-01-02 | 1974-10-15 | Monsanto Co | Selective hydrogenation of c4 acetylenic hydrocarbons |
-
1977
- 1977-06-29 US US05/811,106 patent/US4125568A/en not_active Expired - Lifetime
-
1978
- 1978-06-13 CA CA305,372A patent/CA1099749A/en not_active Expired
- 1978-06-27 DE DE7878300092T patent/DE2861153D1/en not_active Expired
- 1978-06-27 EP EP78300092A patent/EP0000279B1/en not_active Expired
- 1978-06-28 IT IT25074/78A patent/IT1097351B/en active
- 1978-06-28 BR BR7804112A patent/BR7804112A/en unknown
- 1978-06-29 AU AU37606/78A patent/AU517812B2/en not_active Expired
- 1978-06-29 JP JP7811778A patent/JPS5416411A/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE667268A (en) * | 1964-07-29 | 1966-01-24 | ||
US3682779A (en) * | 1969-09-19 | 1972-08-08 | Phillips Petroleum Co | Removal of carbonyl compounds,residual oxygen and other impurities from hydrocarbon dehydrogenation effluent |
US3674887A (en) * | 1970-12-24 | 1972-07-04 | Phillips Petroleum Co | Oxidative dehydrogenation process |
FR2170193A1 (en) * | 1972-02-03 | 1973-09-14 | Petro Tex Chem Corp | |
US3801669A (en) * | 1972-02-03 | 1974-04-02 | Petro Tex Chem Corp | Purification of hydrocarbons |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2215344A (en) * | 1988-02-29 | 1989-09-20 | Shell Int Research | A process for purification of alkenyl aromatic coompounds |
GB2215344B (en) * | 1988-02-29 | 1992-02-26 | Shell Int Research | A process for purification of alkenyl aromatic compounds |
EP0534094A2 (en) * | 1991-09-23 | 1993-03-31 | Occidental Chemical Corporation | Process for removing aldehydes and/or vinyl esters from gaseous or liquid process streams |
EP0534094A3 (en) * | 1991-09-23 | 1994-12-28 | Occidental Chem Co | A process for removing aldehydes and/or vinyl esters from gaseous or liquid process streams |
Also Published As
Publication number | Publication date |
---|---|
EP0000279B1 (en) | 1981-10-14 |
BR7804112A (en) | 1979-03-13 |
IT1097351B (en) | 1985-08-31 |
AU3760678A (en) | 1980-01-03 |
IT7825074A0 (en) | 1978-06-28 |
DE2861153D1 (en) | 1981-12-24 |
AU517812B2 (en) | 1981-08-27 |
US4125568A (en) | 1978-11-14 |
JPS5416411A (en) | 1979-02-07 |
CA1099749A (en) | 1981-04-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0000279A1 (en) | A process for removing organic carbonyl-containing contaminants from a hydrocarbon product stream | |
US6037516A (en) | Method for removal of oxygenate impurities from organic chemical streams | |
US3617546A (en) | Removal of organic compounds by liquid membrane | |
US5276235A (en) | Residual stream upgrading in a propylene oxide-styrene monomer process | |
US2740804A (en) | Process for separating water-oil mixtures containing fine solids | |
KR101164900B1 (en) | Removal of propylene glycol and/or propylene glycol ethers from aqueous streams | |
DE50100283D1 (en) | Process and device for the production of pure aromatic compounds | |
CA1149822A (en) | Process for producing phenolic compounds | |
US3365375A (en) | Process for separating decomposition products of cumene hydroperoxide | |
US3456028A (en) | Clathrate separation process | |
US2106366A (en) | Process and apparatus for contacting fluids | |
US2791536A (en) | Apparatus for contacting liquids | |
US6013821A (en) | Removal of silylated compounds from solvent and gas waste streams | |
US4001341A (en) | Extraction separation | |
US5220103A (en) | Process for the preparation of a cumene feed for cumene oxidation | |
US2355678A (en) | Method for removing impurities from hydrocarbons | |
US5120902A (en) | Process for the preparation of a cumene feed for cumene oxidation | |
US5157205A (en) | Process for removing aldehydes and/or vinyl esters from gaseous or liquid process streams | |
KR830005335A (en) | Solvent Refining of Lubricant | |
US2855437A (en) | Neutralization process | |
US2411808A (en) | Separation of hydrocarbons from water miscible liquids by distillation and washing | |
US3281484A (en) | Process for removing trace olefins from paraffin hydrocarbon containing streams | |
US2762831A (en) | Process and apparatus for regenerating absorbent and extraction media | |
US3269935A (en) | Emulsion breaking in an adduct separation process | |
US3595781A (en) | Solvent extraction of aromatic hydrocarbons |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): BE DE FR GB NL |
|
17P | Request for examination filed | ||
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Designated state(s): BE DE FR GB NL |
|
REF | Corresponds to: |
Ref document number: 2861153 Country of ref document: DE Date of ref document: 19811224 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19820310 Year of fee payment: 5 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 19820331 Year of fee payment: 5 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19820630 Year of fee payment: 5 Ref country code: DE Payment date: 19820630 Year of fee payment: 5 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BE Effective date: 19830627 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19840101 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee | ||
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee | ||
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19840229 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19840301 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19881117 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |