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公开(公告)号：US20170233313A1
公开(公告)日：2017-08-17
申请号：US15503189
申请日：2015-08-11
发明人： Philipp GRÜNE , Oliver HAMMEN , Rainer ECKRICH , Jan Pablo JOSCH , Christian WALSDORFF , Andre BIEGNER , Gergor BLOCH , Heinz BOELT , Hendrik REYNEKE , Christine TOEGEL , Ulrike WENNING
IPC分类号： C07C5/48
CPC分类号： C07C5/48 , C07C7/005 , C07C7/08 , C07C7/09 , C07C7/11 , C07C2523/887 , C07C11/167
摘要： The invention relates to a process for preparing butadiene from n-butenes, comprising the steps of: A) providing an input gas stream a comprising n-butenes, B) feeding the input gas stream a comprising n-butenes and a gas containing at least oxygen into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene, giving a product gas stream b comprising butadiene, unconverted n-butenes, water vapor, oxygen, low-boiling hydrocarbons and high-boiling secondary components, with or without carbon oxides and with or without inert gases; Ca) cooling the product gas stream b by contacting with a cooling medium in at least one cooling zone, the cooling medium being at least partly recycled and having an aqueous phase and an organic phase of an organic solvent, wherein the organic solvent is selected from the group consisting of toluene, o-, m- and p-xylene, mesitylene, mono-, di- and triethylbenzene, mono-, di- and triisopropylbenzene and mixtures thereof, and the mass ratio of the aqueous phase to the organic phase in the cooling medium when it is fed into the cooling zones prior to the contacting with the product gas stream being from 0.015:1 to 10:1, Cb) compressing the cooled product gas stream b which may have been depleted of high-boiling secondary components in at least one compression stage, giving at least one aqueous condensate stream c1 and one gas stream c2 comprising butadiene, n-butenes, water vapor, oxygen and low-boiling hydrocarbons, with or without carbon oxides and with or without inert gases; D) removing uncondensable and low-boiling gas constituents comprising oxygen and low-boiling hydrocarbons, with or without carbon oxides and with or without inert gases, as gas stream d2 from the gas stream c2 by absorbing the C4 hydrocarbons comprising butadiene and n-butenes in an absorbent, giving an absorbent stream laden with C4 hydrocarbons and the gas stream d2, and then desorbing the C4 hydrocarbons from the laden absorbent stream, giving a C4 product gas stream d1, E) separating the C4 product stream d1 by extractive distillation with a butadiene-selective solvent into a stream e1 comprising butadiene and the selective solvent and a stream e2 comprising n-butenes; F) distilling the stream e1 comprising butadiene and the selective solvent into a stream f1 consisting essentially of the selective solvent and a stream f2 comprising butadiene.
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公开(公告)号：US20180354872A1
公开(公告)日：2018-12-13
申请号：US15780725
申请日：2016-12-02
发明人： Jan Pablo JOSCH , Ragavendra Prasad BALEGEDDE RAMACHANDRAN , Philipp GRUENE , Steffan RISSEL , Martin GEMBALA , Ulrike WENNING , Anton WELLENHOFER , Christine TOEGEL , Hendrik REYNEKE
CPC分类号： C07C5/48 , B01D3/40 , B01J19/0053 , B01J2219/00121 , B01J2219/00425 , C07C7/005 , C07C7/08 , C07C7/09 , C07C7/11 , C07C11/167
摘要： A) provision of a feed gas stream a comprising n-butenes;B) introduction of the feed gas stream a comprising n-butenes and an oxygen-comprising gas into a dehydrogenation reactor and oxidative dehydrogenation of n-butenes to butadiene;C) cooling and compression of the product gas stream b in at least one cooling stage comprising a quenching column and in a compression stage comprising a compressor, with the product gas stream b being brought into contact with at least one circulated coolant;D) separation of incondensable and low-boiling gas constituents as gas stream d2 from the gas stream c2 by absorption of the C4-hydrocarbons in at least one circulated absorption medium;E) separation of the C4 product stream d1 by extractive distillation using a solvent which is selective for butadiene into a stream e1 comprising butadiene and the selective solvent and a stream e2 comprising n-butenes;F) distillation of the stream e1 comprising butadiene and the selective solvent to give a stream f1 consisting essentially of the selective solvent and a stream f2 comprising butadiene;wherein the measures (i) to (iii) below are carried out (i) avoidance of formation of explosive gas mixtures by monitoring of the oxygen concentration in the oxygen-comprising gas streams fed into the dehydrogenation zone and control of the mass flows of oxygen-comprising gas streams and gas streams comprising hydrocarbons in such a way that no explosive gas mixtures can be formed; (ii) interruption of the introduction of the oxygen-comprising gas mixture into the dehydrogenation zone when a limit value for the oxygen concentration in the dehydrogenation gas mixture is exceeded; (iii) carrying out of the steps A) to F) in apparatuses which are configured so as to be explosion-protected, where liquid-conveying pipes are configured so as to be explosion-protected and gas conduits are configured so as to be detonation-protected.
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公开(公告)号：US20170334809A1
公开(公告)日：2017-11-23
申请号：US15523862
申请日：2015-11-02
发明人： Philipp GRUNE , Stephan DEUBLEIN , Christian WALSDORFF , Jan Pablo JOSCH , Rainer RAHM , Hendrik REYNEKE , Anton WELLENHOFER , Ulrike WENNING , Christine TOEGEL , Heinz BOELT
IPC分类号： C07C5/48 , C07C7/04 , C07C7/00 , C07C7/11 , C07C11/167
CPC分类号： C07C5/48 , C07C7/005 , C07C7/04 , C07C7/08 , C07C7/11 , C07C11/167 , C07C2523/31 , C07C2523/843 , C07C2523/847
摘要： A process for preparing butadiene from n-butenes, comprising the steps of: A) providing an input gas stream comprising n-butenes; B) feeding the input gas stream comprising n-butenes and a gas containing at least oxygen into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene, giving a product gas stream; Ca) cooling the product gas stream by contacting with a circulating cooling medium in at least one cooling zone; Cb) compressing the cooled product gas stream in at least one compression stage, giving at least one aqueous condensate stream c1 and one gas stream c2; D) removing uncondensable and low-boiling gas constituents comprising oxygen and low-boiling hydrocarbons as gas stream d2 from the gas stream c2 by absorbing the C4 hydrocarbons in an absorbent, giving an absorbent stream laden with C4 hydrocarbons and the gas stream d2, and then desorbing the C4 hydrocarbons from the laden absorbent stream, giving a C4 product gas stream d1; E) separating the C4 product stream d1 by extractive distillation; F) distilling the stream e1 into a stream f1 consisting essentially of the selective solvent and a stream f2 comprising butadiene; G) removing a portion of the aqueous phase of the cooling medium which circulates in step Ca) as aqueous purge stream g; H) distillatively separating the aqueous purge stream g into a fraction h1 and a fraction h2 depleted of organic constituents.
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4.发明申请公开(公告)号：US20200039901A1
公开(公告)日：2020-02-06
申请号：US16498693
申请日：2018-03-26
发明人： Jan UNGELENK , Oliver HAMMEN , Christian WALSDORFF , Rainer ECKRICH , Heinz BOELT , Christine TOEGEL , Ulrike WENNING , Hendrik REYNEKE , Anton WELLENHOFER
IPC分类号： C07C11/167 , C07C7/04 , C07C7/11 , C07C5/333
摘要： The invention relates to a process for preparing butadiene from n-butenes in n reactors R1 to Rn operated in parallel, wherein the process in the production phase of a reactor Rm in the n reactors comprises the steps: A) provision of a feed gas stream a1m comprising n-butenes; B) feeding of the feed gas stream a1m comprising n-butenes, an oxygen-comprising gas stream a2m and a substream d2m of an oxygen-comprising total recycle gas stream d2 into the oxidative dehydrogenation zone of the reactor and oxidative dehydrogenation of n-butenes to butadiene, giving a product gas substream bm comprising butadiene; C) combination of the product gas substream bm with further product gas substreams to form a total product gas stream b and cooling and compression of the total product gas stream b and condensation of at least part of the high-boiling secondary components, giving at least one aqueous condensate stream c1 and a gas stream c2 comprising butadiene; D) feeding of the gas stream c2 into an absorption zone and separation of incondensable and low-boiling gas constituents as gas stream d from the gas stream c2 by absorption of the C4-hydrocarbons in an absorption medium, giving an absorption medium stream d1 loaded with C4-hydrocarbons and a recycle gas stream d2, and recirculation of a substream d2m of the total recycle gas stream d2 into the reactor Rm, and during the regeneration phase of the reactor Rm further reactors are in the production phase and the regeneration phase of the reactor Rm comprises the steps in the order i) to v): i) reduction of the feed gas stream a1m comprising n-butenes and of the oxygen-comprising gas stream a2m and the feeding of an inert gas stream a4m into the reactor Rm; ii) further reduction of the feed gas stream a1m comprising n-butenes down to 0, reduction of the recycle gas substream d2m and increase of the inert gas stream a4m until the oxygen content in the reactor Rm is from 2 to 3% by volume; iii) regeneration of the catalyst by burning off carbon-comprising deposits at an oxygen content of from 2 to 3% by volume; iv) reduction of the inert gas stream a4m and increase of the recycle gas substream d2m until the oxygen content in the reactor Rm is from 4 to 10% by volume; v) reoxidation of the catalyst at an oxygen content of from 4 to 10% by volume.
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公开(公告)号：US20180105479A1
公开(公告)日：2018-04-19
申请号：US15561711
申请日：2016-03-23
发明人： Jan Pablo JOSCH , Ragavendra Prasad BALEGEDDE RAMACHANDRAN , Christian Walsdorff , Regina BENFER , Anton WELLENHOFER , Ulrike WENNING , Heinz BOELT , Hendrik REYNEKE , Christine TOEGEL
摘要： The invention relates to a process for producing butadiene from n-butenes which comprises the steps of: A) providing a vaporous n-butenes-comprising input gas stream a1 by evaporating a liquid n-butenes-comprising stream a0; B) introducing the vaporous n-butenes-comprising input gas stream a1 and an at least oxygenous gas into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene to obtain a product gas stream b comprising butadiene, unconverted n-butenes, steam, oxygen, low-boiling hydrocarbons, high-boiling secondary components, possibly carbon oxides and possibly inert gases, Ca) chilling the product gas stream b by contacting with a cooling medium comprising an organic solvent in at least one chilling zone, the cooling medium being at least partially recycled into the chilling zone, Cb) compressing the chilled product gas stream b which is possibly depleted of high-boiling secondary components in at least one compression stage to obtain at least one aqueous condensate stream c1 and a gas stream c2 comprising butadiene, n-butenes, steam, oxygen, low-boiling hydrocarbons, possibly carbon oxides and possibly inert gases, D) removing noncondensable and low-boiling gas constituents comprising oxygen, low-boiling hydrocarbons, possibly carbon oxides and possibly inert gases as gas stream d2 from the gas stream c2 by absorbing the C4 hydrocarbons comprising butadiene and n-butenes into an absorption medium to obtain a C4-hydrocarbons-laden absorption medium stream and the gas stream d2 and subsequently desorbing the C4 hydrocarbons from the laden absorption medium stream to obtain a C4 product gas stream d1, wherein at least some of the recycled cooling medium from step Ca) is brought into thermal contact with the liquid n-butenes-comprising stream a0 in one or more indirect heat exchangers and at least some of the liquid n-butenes-comprising stream a0 is evaporated by indirect heat transfer with the recycled cooling medium.
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公开(公告)号：US20190337870A1
公开(公告)日：2019-11-07
申请号：US16324315
申请日：2017-08-08
发明人： JAN UNGELENK , Oliver HAMMEN , Ulrich HAMMON , Rainer ECKRICH , Signe UNVERRICHT , Christian WALSDORFF , Heinz BOELT , Hendrik REYNEKE , Christine TOEGEL , Anton WELLENHOFER , Ulrike WENNING
IPC分类号： C07C5/48 , C07C7/11 , C07C11/167
摘要： Process for preparing butadiene from n-butenes, which has a start-up phase and an operating phase and the operating phase of the process comprises the steps: A) provision of a feed gas stream a1 comprising n-butenes; B) introduction of the feed gas stream a1 comprising n-butenes, an oxygen-comprising gas stream a2 and an oxygen-comprising recycle gas stream d2 into at least one oxidative dehydrogenation zone and oxidative dehydrogenation of n-butenes to butadiene, giving a product gas stream b comprising butadiene; C) cooling and compression of the product gas stream b, giving at least one aqueous condensate stream c1 and a gas stream c2 comprising butadiene; D) introduction of the gas stream c2 into an absorption zone and separation of incondensable and low-boiling gas constituents as gas stream d from the gas stream c2 by absorption of the C4 hydrocarbons in an absorption medium, giving an absorption medium stream loaded with C4 hydrocarbons and the gas stream d, and recirculation of the gas stream d as recycle gas stream d2 to the oxidative dehydrogenation zone, where the start-up phase comprises the steps, in the order i) to iv): i) introduction of a gas stream d2′ having a composition corresponding to the recycle gas stream d2 in the operating phase into the dehydrogenation zone and setting of the recycle gas stream d2 to at least 70% of the total volume flow in the operating phase; ii) optionally additional introduction of a steam stream a3 into the dehydrogenation zone; iii) additional introduction of the feed gas stream a1 comprising butenes at a lower volume flow than in the operating phase and raising of this volume flow until at least 50% of the volume flow of the feed gas stream a1 in the operating phase has been attained, with the total gas flow through the dehydrogenation zone corresponding to not more than 120% of the total gas flow during the operating phase; iv) additional introduction, when at least 50% of the volume flow of the feed gas stream a1 comprising butenes in the operating phase has been attained, of an oxygen-comprising stream a2 at a lower volume flow than in the operating phase and raising of the volume flows of the feed gas streams a1 and a2 until the volume flows in the operating phase have been attained, with the total gas flow through the dehydrogenation zone corresponding to not more than 120% of the total gas flow during the operating phase.
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公开(公告)号：US20190039971A1
公开(公告)日：2019-02-07
申请号：US16074454
申请日：2017-01-30
发明人： JAN Pablo JOSCH , Ragavendra Prasad BALEGEDDE RAMACHANDRAN , Ulrike WENNING , Anton WELLENHOFER , Christine TOEGEL , Hendrik REYNEKE , Heinz BOELT
IPC分类号： C07C5/48 , C07C11/167 , C07C11/08 , C07C7/08 , C07C7/11
摘要： The invention relates to a method for producing butadiene from n-butenes having the steps: A) providing an n-butene-comprising feed gas stream a; B) feeding the n-butene-comprising feed gas stream a and an oxygen-comprising gas into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene, wherein a product gas stream b comprising butadiene, unreacted n-butenes, steam, oxygen, low-boiling hydrocarbons, high-boiling minor components, optionally carbon oxides and optionally inert gases is obtained; Ca) cooling the product gas stream b by contacting it with a refrigerant and condensing at least a part of the high-boiling minor components; Cb) compressing the remaining product gas stream b in at least one compression step, wherein at least one aqueous condensate stream c1 and a gas stream c2 comprising butadiene, n-butenes, steam, oxygen, low-boiling hydrocarbons, optionally carbon oxides and optionally inert gases is obtained; Da) separating off non-condensable and low-boiling gas components comprising oxygen, low-boiling hydrocarbons, optionally carbon oxides and optionally inert gases as gas stream d2 from the gas stream c2 by absorbing the C4 hydrocarbons comprising butadiene and n-butenes in an absorption medium, wherein an absorption medium stream loaded with C4 hydrocarbons and the gas stream d2 are obtained, and Db) subsequently desorbing the C4 hydrocarbons from the loaded absorption medium stream in a desorption column, wherein a C4 product gas stream d1 is obtained, Dc) separating off the steam condensate from the absorption medium in a phase separator and vaporizing it in a steam generator and providing it again as stripping gas in the desorption column, wherein, the steam condensate before the vaporization in a steam generator, is subjected to a pretreatment in a further method step.
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公开(公告)号：US20180072638A1
公开(公告)日：2018-03-15
申请号：US15561623
申请日：2016-03-14
发明人： Jan Pablo JOSCH , Stephan DEUBLEIN , Regina BENFER , Friedemann GAITZSCH , Hendrik REYNEKE , Christine TOEGEL , Ulrike WENNING , Anton WELLENHOFER , Heinz BOELT
摘要： The invention relates to a process for producing butadiene from n-butenes, comprising the steps of: A) providing an n-butenes-comprising input gas stream a1, B) feeding the n-butenes-comprising input gas stream al, an oxygenous gas and an oxygenous cycle gas stream a2 into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene to obtain a product gas stream b comprising butadiene, unconverted n-butenes, steam, oxygen, low-boiling hydrocarbons, high-boiling secondary components, possibly carbon oxides and possibly inert gases, Ca) cooling down the product gas stream b and optionally at least partially removing high-boiling secondary components and steam to obtain a product gas stream b′, Cb) compressing and cooling the product gas stream b′ in at least one compression and cooling stage to obtain at least one aqueous condensate stream c1 and one gas stream c2 comprising butadiene, n-butenes, steam, oxygen, low-boiling hydrocarbons, possibly carbon oxides and possibly inert gases, Da) absorbing the C4 hydrocarbons comprising butadiene and n-butenes into an aromatic hydrocarbon solvent absorption medium stream A1 in an absorption column K1 and removing noncondensable and low-boiling gas constituents comprising steam, oxygen, low-boiling hydrocarbons, possibly carbon oxides, aromatic hydrocarbon solvent and possibly inert gases as gas stream d2 from the gas stream c2 to obtain a C4 hydrocarbons-laden absorption medium stream A1′ and the gas stream d2 and subsequently desorbing the C4 hydrocarbons from the laden absorption medium stream A1′ to obtain a C4 product gas stream d1, Db) at least partially recycling the gas stream d2 into the oxidative dehydrogenation zone as cycle gas stream a2, wherein said process comprises limiting the content of aromatic hydrocarbon solvent in the cycle gas stream a2 to less than 1 vol % by contacting in a further column K2 the gas stream d2 exiting the removal stage Da) with an at least partially recirculating liquid absorption medium stream A2 for the aromatic hydrocarbon solvent A1, and limiting the water content of the liquid absorption medium stream A2 in the column K2 to no more than 80 wt %.
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公开(公告)号：US20180002254A1
公开(公告)日：2018-01-04
申请号：US15514077
申请日：2015-09-14
发明人： Jan Pablo JOSCH , Philipp GRÜNE , Regina BENFER , Maximilian VICARI , Andre BIEGNER , Gergor BLOCH , Heinz BOELT , Hendrik REYNEKE , Christine TOEGEL , Ulrike WENNING
摘要： The invention relates to a process for preparing butadiene from n-butenes, comprising the steps of: A) providing an input gas stream a comprising n-butenes, B) feeding the input gas stream a comprising n-butenes and a gas containing at least oxygen into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene, giving a product gas stream b comprising butadiene, unconverted n-butenes, water vapor, oxygen, low-boiling hydrocarbons and high-boiling secondary components, with or without carbon oxides and with or without inert gases; Ca) cooling the product gas stream b by contacting with a cooling medium in at least one cooling zone, the cooling medium being at least partly recycled and having an aqueous phase and an organic phase, Cb) compressing the cooled product gas stream b which may have been depleted of high-boiling secondary components in at least one compression stage, giving at least one aqueous condensate stream c1 and one gas stream c2 comprising butadiene, n-butenes, water vapor, oxygen and low-boiling hydrocarbons, with or without carbon oxides and with or without inert gases; D) removing uncondensable and low-boiling gas constituents comprising oxygen and low-boiling hydrocarbons, with or without carbon oxides and with or without inert gases, as gas stream d2 from the gas stream c2 by absorbing the C4 hydrocarbons comprising butadiene and n-butenes in an absorbent, giving an absorbent stream laden with C4 hydrocarbons and the gas stream d2, and then desorbing the C4 hydrocarbons from the laden absorbent stream, giving a C4 product gas stream d1, E) separating the C4 product stream d1 by extractive distillation with a butadiene-selective solvent into a stream e1 comprising butadiene and the selective solvent and a stream e2 comprising n-butenes; F) distilling the stream e1 comprising butadiene and the selective solvent into a stream f1 consisting essentially of the selective solvent and a stream f2 comprising butadiene, wherein stage Cb) comprises at least two compression stages Cba) and at least two cooling stages Cbb) configured in the form of quench columns, the cooling in the cooling stages being effected by direct contacting with a biphasic cooling medium having an aqueous phase and an organic phase.
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公开(公告)号：US20190016650A1
公开(公告)日：2019-01-17
申请号：US16069553
申请日：2017-01-11
发明人： Jan Pablo JOSCH , Georgios KARANIKOULIS , Oliver HAMMEN , Claudia MOSSBACHER , Ulrike WENNING , Anton WELLENHOFER , Christine TOEGEL , Hendrik REYNEKE
CPC分类号： C07C5/48 , C07C7/005 , C07C7/04 , C07C7/06 , C07C7/08 , C07C7/09 , C07C7/11 , C07C2521/06 , C07C2523/31 , C07C2523/86 , C07C2523/88 , C07C2523/881 , C07C11/167 , C07C11/08
摘要： The invention relates to a method for producing butadiene from n-butenes having the steps: A) providing a feed gas stream a comprising n-butenes; B) feeding the feed gas stream a comprising the n-butenes and an oxygen-comprising gas into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene, wherein a product gas stream b comprising butadiene, unreacted n-butenes, steam, oxygen, low-boiling hydrocarbons, high-boiling minor components, possibly carbon oxides and possibly inert gases is obtained; Ca) cooling the product gas stream b by contacting it with a refrigerant and condensing at least a part of the high-boiling minor components; Cb) compressing the remaining product gas stream b in at least one compression stage, wherein at least one aqueous condensate stream c1 and a gas stream c2 comprising butadiene, n-butenes, steam, oxygen, low-boiling hydrocarbons, possibly carbon oxides and possibly inert gases are obtained; Da) separating off non-condensable and low-boiling gas components comprising oxygen, low-boiling hydrocarbons, possibly carbon oxides and possibly inert gases as gas stream d2 from the gas stream c2 by absorbing the C4 hydrocarbon-comprising butadiene and n-butenes in an absorbent, wherein an absorbent stream loaded with C4 hydrocarbons and the gas stream d2 are obtained, and Db) subsequent desorption of the C4 hydrocarbons from the loaded absorbent stream in a desorption column, wherein a C4 product gas stream d1 is obtained, wherein a polymerization inhibitor is added in step Db) at the column head of the desorption column.
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