WO2012165950A2 - Extraction d'un aminoalcane à partir d'une matière première aqueuse - Google Patents

Extraction d'un aminoalcane à partir d'une matière première aqueuse Download PDF

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Publication number
WO2012165950A2
WO2012165950A2 PCT/NL2012/050371 NL2012050371W WO2012165950A2 WO 2012165950 A2 WO2012165950 A2 WO 2012165950A2 NL 2012050371 W NL2012050371 W NL 2012050371W WO 2012165950 A2 WO2012165950 A2 WO 2012165950A2
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WO
WIPO (PCT)
Prior art keywords
aminoalkane
extract
raffinate
expelling agent
diaminobutane
Prior art date
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Ceased
Application number
PCT/NL2012/050371
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English (en)
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WO2012165950A3 (fr
Inventor
André Banier De Haan
Agnieszka KRZYZANIAK
Boelo SCHUUR
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STICHTING PUBLIC PRIVATE PARTNERSHIP INSTITUTE FOR SUSTAINABLE PROCESS TECHNOLOGY
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STICHTING PUBLIC PRIVATE PARTNERSHIP INSTITUTE FOR SUSTAINABLE PROCESS TECHNOLOGY
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Publication of WO2012165950A2 publication Critical patent/WO2012165950A2/fr
Publication of WO2012165950A3 publication Critical patent/WO2012165950A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/86—Separation

Definitions

  • the present invention relates to a process of extracting an aminoalkane, such as a monoaminoalkane or a diaminoalkane, such as diaminobutane or diaminopentane, or diaminohexane from an aminoalkane -containing aqueous feed.
  • an aminoalkane such as a monoaminoalkane or a diaminoalkane, such as diaminobutane or diaminopentane, or diaminohexane from an aminoalkane -containing aqueous feed.
  • Aminoalkane s are important industrial chemicals as monomers for polyamide production, for example 1,4-diaminobutane is used in the production of polyamide 4,6 or polyamide 4, 10 formed by reacting 1,4-diaminobutane with adipic acid or sebacic acid respectively, or as raw material for several fine chemicals purposes.
  • a process of producing industrial chemicals such as aminoalkanes that is currently drawing interest is fermentation, in which suitable microorganisms produce the aminoalkane in an aqueous environment in a vessel that is called a fermentor.
  • the present invention is related to removing aminoalkanes from the fermentor content. More in particular, the present invention is related to removing the aminoalkane from the aqueous stream that is withdrawn from the fermentor to obtain a purified aqueous stream that can be returned to the fermentor.
  • USA patent specification No. 3 433 788 discloses a process of extracting an aminoalkane, such as a monoaminoalkane or a diaminoalkane, such as diaminobutane, from an aqueous aminoalkane- containing feed comprising the steps of (a) contacting the aqueous feed with a depleted solvent including an alkylated phenol to obtain a first extract enriched in aminoalkane and a first raffinate having a reduced aminoalkane -content; (b) separating the first raffinate from the first extract; and (c) recovering the aminoalkane from the first extract to obtain an aminoalkane- containing stream and a depleted solvent for use in step (a), wherein recovering the aminoalkane involves a distillation step.
  • an aminoalkane such as a monoaminoalkane or a diaminoalkane, such as diaminobutane
  • USA patent specification No. 4 582 937 discloses a process of extracting an ethyleneamine from an aqueous ethyleneamine-containing feed comprising the steps of (a) contacting the aqueous feed with a depleted solvent including an alkylated phenol to obtain a first extract enriched in ethyleneamine and a first raffinate having a reduced ethyleneamine-content; (b) separating the first raffinate from the first extract; and (c) recovering the ethyleneamine from the first extract to obtain a depleted solvent for use in step (a), wherein recovering the ethyleneamine comprises contacting the first extract with an aqueous carbonic acid solution or carbon dioxide gas to back-extract the ethyleneamine in the form of a salt.
  • the first raffinate having a reduced aminoalkane-content can be used as the purified aqueous stream that can be returned to the fermentor.
  • a disadvantage of the first of the two known processes is that recovering the aminoalkane involves an energy consuming distillation step at elevated temperatures to achieve separation.
  • a disadvantage of the second process is that recovering the aminoalkane involves using an acid to obtain a salt of the aminoalkane, which salt subsequently has to be converted to obtain the aminoalkane.
  • the present invention relates to a process of extracting an aminoalkane from an aminoalkane-containing aqueous feed comprising the steps of
  • step (c) recovering the aminoalkane from the first extract to obtain an aminoalkane- containing stream and a depleted solvent for use in step (a),
  • recovering the aminoalkane comprises contacting the first extract with an expelling agent which is immiscible with water, selected from the group including C5-
  • step (a) C15 alkanes and C5-C20 fatty alcohols, and sufficient water to dissolve the expelled aminoalkane to obtain a second extract enriched in aminoalkane and a second raffinate including the expelling agent, separating the second extract from the second raffinate to obtain an aqueous product stream enriched in aminoalkane, and removing expelling agent from the second raffinate to obtain the depleted solvent for use in step (a).
  • the aminoalkane is present in the mixture of first extract and expelling agent and in the water, an aqueous phase. Surprisingly it was found that the concentration of aminoalkane in the aqueous phase steeply increases with increasing concentration of expelling agent.
  • the expelling agent selected from the group including C5-C15 alkanes and C5- C20 fatty alcohols, is immiscible with water and miscible with the solvent.
  • a process of producing an aminoalkane is carried out wherein suitable microorganisms produce the aminoalkane in an aqueous environment in the presence of a nutrient.
  • a purified aqueous stream is supplied to the fermentor 1 through conduit 2, and an aqueous stream containing aminoalkane is withdrawn from the fermentor through conduit 5.
  • the aqueous stream in conduit 5 is the aminoalkane-containing aqueous feed for the extraction process of the present invention.
  • auxiliary equipment such as filters and pumps.
  • the aqueous feed 5 is contacted in a first contactor 7 with a depleted solvent comprising an alkylated phenol which is supplied to the first contactor 7 through conduit 9, to obtain a first extract enriched in aminoalkane and a first raffinate having a reduced aminoalkane-content.
  • a solvent with a low mutual solubility towards water in this contacting step will be beneficial to the overall process economy.
  • the first extract enriched in aminoalkane is withdrawn from the first contactor 7 through conduit 12, and the first raffinate having a reduced aminoalkane-content is withdrawn from the first contactor 7 through conduit 2.
  • the first raffinate is supplied as the purified aqueous stream to the fermentor 1.
  • the aminoalkane is recovered from the first extract 12 to obtain an aminoalkane-containing stream and a depleted solvent.
  • the first extract is supplied to a second contactor 15 in which the first raffinate is contacted with an expelling agent supplied to the second contactor 15 through conduit 17. Moreover, the first extract is also contacted with just sufficient water, supplied through conduit 20 to dissolve the expelled aminoalkane.
  • the second contactor 15 are obtained a second extract enriched in aminoalkane and a second raffinate including the expelling agent.
  • the second extract enriched in aminoalkane is withdrawn from the second contactor 15 through conduit 22.
  • This second extract is the aqueous product stream enriched in aminoalkane.
  • the aminoalkane may subsequently be recovered by any suitable means (not shown).
  • the second raffinate including the expelling agent is withdrawn from the second contactor 15 through conduit 25.
  • the second raffinate In order to remove the expelling agent from the second raffinate, the second raffinate is heated in heat exchanger 30 so as to evaporate the expelling agent, and supplied to separation vessel 35 to allow separation of the vaporized expelling agent from the second raffinate.
  • the expelling agent is withdrawn from the separation vessel 35 through conduit 39, condensed in heat exchanger 40 and returned through conduit 17 to the second contactor 15.
  • Depleted solvent is passed from the separation vessel 35 through conduit 9 to the first contactor 7.
  • the contactors 7 and 15 can be any suitable contactors known in the art, such as counter-current contactors.
  • Example 1 relates to extraction of 1,4-diaminobutane from an aqueous feed; examples 2 and 2 A relate to recovering 1,4 diaminobutane from a first extract, wherein example 2A is a comparative example not according to the invention; examples 3 and 4 relate to recovering 1,4-diaminobutane from a first extract; example 5 relates to extraction of 1, 5-diaminopentane from an aqueous feed, and examples 6 and 6A relate to recovering 1, 5-diaminopentane from a first extract, wherein example 6A is a comparative example not according to the invention.
  • Example 1 Extraction of 1,4-diaminobutane from an aqueous feed.
  • the extraction process comprised contacting for 17 hours in an incubator 0.010 kg of the aqueous feed with 0.010 kg depleted solvent consisting of 100 wt% 4-nonylphenol, to obtain a first extract enriched in aminoalkane and a first raffinate having a reduced aminoalkane-content.
  • Example 2 an aminoalkane in the form of 1,4-diaminobutane was recovered from 0.002 kg of a first extract consisting of 0.994 wt% 1,4-diaminobutane in 4- nonylphenol to obtain an aminoalkane -containing stream and a depleted solvent for use in the extraction step.
  • Recovering the aminoalkane comprises mixing the first extract with an expelling agent in the form of 0.008 kg octanol and 0.010 kg water to dissolve the expelled aminoalkane for 17 hours in a temperature controlled incubator to obtain a second extract enriched in aminoalkane and a second raffinate including the expelling agent.
  • the second extract was allowed to separate from the second raffinate to obtain an aqueous product stream enriched in aminoalkane. Analysis showed that the concentration of 1,4-diaminobutane in the aqueous product stream was 0.128 wt% and pH increased to 11.29. Hence, 65% of 1,4-diaminobutane had been recovered.
  • Example 2A Recovering 1,4-diaminobutane from a first extract (comparative example not according to the invention without expelling agent).
  • Example 2A an aminoalkane in the form of 1,4-diaminobutane was recovered from 0.002 kg of a first extract consisting of 0.994 wt% 1,4-diaminobutane in 4-nonylphenol to obtain an aminoalkane-containing stream and a depleted solvent for use in the extraction step.
  • Recovering the aminoalkane comprises mixing 0.002 kg of the first extract and 0.010 kg water to dissolve aminoalkane for 17 hours in a temperature controlled incubator to obtain a second extract enriched in aminoalkane and a second raffinate including 4-nonylphenol.
  • the second extract was allowed to separate from the second raffinate to obtain an aqueous product stream enriched in aminoalkane.
  • Example 3 Recovering 1,4-diaminobutane from a first extract.
  • an aminoalkane in the form of 1,4-diaminobutane was recovered from 0.002 kg of a first extract consisting of 0.994 wt% 1,4-diaminobutane in 4- nonylphenol to obtain an aminoalkane -containing stream and a depleted solvent for use in the extraction step.
  • Recovering the aminoalkane comprises mixing the first extract with an expelling agent in the form of 0.008 kg 2-octyl-l-dodecanol and 0.010 kg water to dissolve the expelled aminoalkane for 17 hours in a temperature controlled incubator to obtain a second extract enriched in aminoalkane and a second raffinate including the expelling agent.
  • the second extract was allowed to separate from the second raffinate to obtain an aqueous product stream enriched in aminoalkane.
  • Analysis showed that the concentration of 1,4-diaminobutane in the aqueous product stream was 0.129 wt% and pH increased to 11.212. Hence, 65% of 1,4-diaminobutane had been recovered.
  • Example 4 Recovering 1,4-diaminobutane from a first extract
  • Example 4 an aminoalkane in the form of 1,4-diaminobutane was recovered from 0.002 kg of a first extract consisting of 1.12 wt% 1,4-diaminobutane in 4- nonylphenol to obtain an aminoalkane -containing stream and a depleted solvent for use in the extraction step.
  • Recovering the aminoalkane comprises mixing the first extract with an expelling agent in the form of 0.008 kg heptane and 0.010 kg water to dissolve the expelled aminoalkane for 17 hours at 25 °C in a temperature controlled incubator to obtain a second extract enriched in aminoalkane and a second raffinate including the expelling agent.
  • the second extract was allowed to separate from the second raffinate to obtain an aqueous product stream enriched in aminoalkane. Analysis showed that the concentration of 1,4-diaminobutane in the aqueous product stream was 0.026 wt% and pH increased to 10.6. Hence, 11.6% of 1,4-diaminobutane had been recovered.
  • Example 5 Extraction of 1,5-diaminopentane from an aqueous feed.
  • the extraction process comprised contacting for 17 hours in an incubator 0.010 kg of the aqueous feed with 0.010 kg depleted solvent consisting of 100 wt% 4-nonylphenol, to obtain a first extract enriched in aminoalkane and a first raffinate having a reduced aminoalkane-content.
  • Example 6 Recovering 1,5-diaminopentane from a first extract.
  • Example 6 an aminoalkane in the form of 1,5-diaminopentane was recovered from 0.002 kg of a first extract consisting of 1.30 wt% 1,5-diaminopentane in 4- nonylphenol to obtain an aminoalkane -containing stream and a depleted solvent for use in the extraction step.
  • Recovering the aminoalkane comprises mixing the first extract with an expelling agent in the form of 0.008 kg 2-octyl-l-dodecanol and 0.010 kg water to dissolve the expelled aminoalkane for 17 hours at 25 °C in a temperature controlled incubator to obtain a second extract enriched in aminoalkane and a second raffinate including the expelling agent.
  • the second extract was allowed to separate from the second raffinate to obtain an aqueous product stream enriched in aminoalkane. Analysis showed that the concentration of 1,5-diaminopentane in the aqueous product stream was 0.093 wt% and pH increased to 11.3. Hence, 36% of 1,5- diaminopentane had been recovered.
  • Example 6A Recovering 1,5-diaminopentane from a first extract (comparative example not according to the invention without expelling agent).
  • an aminoalkane in the form of 1,5-diaminopentane was recovered from 0.002 kg of a first extract consisting of 1.30 wt% 1,5-diaminopentane in 4-nonylphenol to obtain an aminoalkane-containing stream and a depleted solvent for use in the extraction step.
  • Recovering the aminoalkane comprises mixing 0.002 kg of the first extract and 0.010 kg water to dissolve aminoalkane for 17 hours in a temperature controlled incubator to obtain a second extract enriched in aminoalkane and a second raffinate including 4-nonylphenol.
  • the second extract was allowed to separate from the second raffinate to obtain an aqueous product stream enriched in aminoalkane. Analysis showed that the concentration of 1,5-diaminopentane in the aqueous product stream was below the detection limit for 1,5-diaminopentane, i.e. 0.0102wt% and pH increased to 10.116. Hence, less than 3.9% of 1,5-diaminopentane was recovered.
  • Examples 2 and 2A and 6 and 6A show clearly the effect of the expelling agent.
  • the expelling agent is a C5-C15 alkane, for example heptane.
  • the expelling agent is a C5-C20 alcohol, such as octanol or an octyldodecanol.
  • the alkylated phenol in the solvent used in step (a) is a nonylphenol or a di-alkylated-phenol.
  • the solvent may contain a suitable diluent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé d'extraction d'un aminoalcane à partir d'une matière première aqueuse contenant un aminoalcane (5) comprenant (a) la mise en contact (7) de la matière première aqueuse (5) avec un solvant appauvri comprenant un phénol alkylé pour obtenir un premier extrait (12) enrichi en aminoalcane et un premier raffinat (2) ayant une teneur réduite en aminoalcane ; (b) la mise en contact (15) du premier extrait (12) avec un agent d'extraction (17) et suffisamment d'eau (20) pour dissoudre l'aminoalcane extraite pour obtenir un deuxième extrait enrichi en aminoalcane (22) et un deuxième raffinat comprenant l'agent d'extraction (25) ; (c) le retrait du deuxième extrait (22) du deuxième raffinat (25) pour obtenir un flux de produit aqueux enrichi en aminoalcane (22) ; et (d) le retrait de l'agent d'extraction (39) à partir du deuxième raffinat (25) pour obtenir le solvant appauvri (9) pour utilisation dans l'étape (a).
PCT/NL2012/050371 2011-05-27 2012-05-25 Extraction d'un aminoalcane à partir d'une matière première aqueuse Ceased WO2012165950A2 (fr)

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EP11167874 2011-05-27
EP11167874.4 2011-05-27

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WO2012165950A2 true WO2012165950A2 (fr) 2012-12-06
WO2012165950A3 WO2012165950A3 (fr) 2013-04-25

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104478733A (zh) * 2014-12-10 2015-04-01 九江天赐高新材料有限公司 从dmapa重组分中回收双dmapa的方法
CN108997130A (zh) * 2018-08-29 2018-12-14 南京工业大学 一种1,5-戊二胺萃取和成盐耦合的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3433788A (en) 1966-04-27 1969-03-18 Union Carbide Corp Process for recovery of amines from aqueous solutions by solvent treatment and distillation
US4582937A (en) 1982-06-04 1986-04-15 Toyo Soda Manufacturing Co., Ltd. Process for recovering ethyleneamines

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864402A (en) * 1973-05-07 1975-02-04 Texaco Inc Purification of secondary alkyl amines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3433788A (en) 1966-04-27 1969-03-18 Union Carbide Corp Process for recovery of amines from aqueous solutions by solvent treatment and distillation
US4582937A (en) 1982-06-04 1986-04-15 Toyo Soda Manufacturing Co., Ltd. Process for recovering ethyleneamines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104478733A (zh) * 2014-12-10 2015-04-01 九江天赐高新材料有限公司 从dmapa重组分中回收双dmapa的方法
CN108997130A (zh) * 2018-08-29 2018-12-14 南京工业大学 一种1,5-戊二胺萃取和成盐耦合的方法

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