[go: up one dir, main page]

WO2012158180A1 - Procédés pour produire du butanediole (bdo) et du diaminobutane (dab) a partir de bouillons de fermentation contenant du succinate d'ammonium - Google Patents

Procédés pour produire du butanediole (bdo) et du diaminobutane (dab) a partir de bouillons de fermentation contenant du succinate d'ammonium Download PDF

Info

Publication number
WO2012158180A1
WO2012158180A1 PCT/US2011/049682 US2011049682W WO2012158180A1 WO 2012158180 A1 WO2012158180 A1 WO 2012158180A1 US 2011049682 W US2011049682 W US 2011049682W WO 2012158180 A1 WO2012158180 A1 WO 2012158180A1
Authority
WO
WIPO (PCT)
Prior art keywords
mas
bottoms
das
water
solid portion
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.)
Ceased
Application number
PCT/US2011/049682
Other languages
English (en)
Inventor
Olan S. Fruchey
Leo E. Manzer
Dilum Dunuwila
Brian T. Keen
Brooke A. Albin
Nye A. Clinton
Bernard D. Dombek
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bioamber SAS
Original Assignee
Bioamber SAS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from PCT/US2011/036913 external-priority patent/WO2011146556A1/fr
Application filed by Bioamber SAS filed Critical Bioamber SAS
Priority to US14/117,141 priority Critical patent/US9464030B2/en
Priority to EP11757460.8A priority patent/EP2709978A1/fr
Publication of WO2012158180A1 publication Critical patent/WO2012158180A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/44—Polycarboxylic acids
    • C12P7/46—Dicarboxylic acids having four or less carbon atoms, e.g. fumaric acid, maleic acid

Definitions

  • the slurry was then cooled to 15°C and held for 30 minutes, then to 10°C and held for 30 minutes, and finally to 5°C and held for 30 minutes, all while stirring.
  • the slurry was filtered cold and air was sucked through the cake for several minutes to remove as much liquid as possible, yielding 110g of brown mother liquor (pH 5.0).
  • the solids were then dried in a vacuum oven at 75°C for one hour yielding 24g of off-white crystals.
  • Carbon and nitrogen analyses of the solids revealed a 4.04 molar ratio of carbon to nitrogen (i.e. a 1.01 ratio of ammonia to SA or about 99% MAS).
  • HPLC analysis revealed that the MAS contained 0.07% succinamic acid but no detectable succinamide, succinimide or acetate species. In other words, the MAS was free of DAS and otherwise substantially pure.
  • a three neck 500 mL round bottom flask was fitted with a thermometer, a 250 mL addition funnel and a Dean Stark trap topped with a reflux condenser.
  • the flask was charged with 100g of toluene and 100g of an about 9% DAS broth solution (which also contained about 1% ammonium acetate and ammonium formate combined).
  • the addition funnel was charged with 250g of the 9% diammonim succinate broth solution.
  • the contents of the flask were stirred with a magnetic stirrer and heated with a heating mantel bringing the contents to boil.
  • This column was operated at 30 psig pressure which gave a column temperature of 137°C.
  • the top of the column was fed a synthetic 10% DAS solution at a rate of 5 mL/min and water was fed to the reboiler at a rate of 5 mlVmin.
  • the overhead distillate rate was 8 mL rnin and the residue rate was 2 mL/min. Titration of the distillate for ammonia indicated that the about 47% of the ammonia had been removed in the distillate (i.e. the conversion to MAS was about 94%).
  • the residue liquid was about 20% MAS and HPLC analysis of the residue indicated an about 3% inefficiency to succinamic acid.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

La présente invention concerne des procédés pour produire des composés contenant de l'azote qui comprennent la conversion d'acide succinique (SA) ou de succinate de mono-ammonium (MAS) dérivé d'un bouillon de fermentation contenant du succinate de diammonium (DAS) ou MAS pour produire de tels composés comprenant du diaminobutane (DAB), du dinitrile succinique (SDN), de l'aminonitrile succinique (SAN), du succinamide (DAM), et des polymères associés.
PCT/US2011/049682 2011-05-18 2011-08-30 Procédés pour produire du butanediole (bdo) et du diaminobutane (dab) a partir de bouillons de fermentation contenant du succinate d'ammonium Ceased WO2012158180A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US14/117,141 US9464030B2 (en) 2011-05-18 2011-08-30 Processes for producing butanediol (BDO), diaminobutane (DAB), succinic dinitrile (SDN) and succinamide (DAM)
EP11757460.8A EP2709978A1 (fr) 2011-05-18 2011-08-30 Procédés pour produire du butanediole (bdo) et du diaminobutane (dab) a partir de bouillons de fermentation contenant du succinate d'ammonium

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
USPCT/US2011/036913 2011-05-18
PCT/US2011/036913 WO2011146556A1 (fr) 2010-05-19 2011-05-18 Procédés pour produire du diaminobutane (dab), du dinitrile succinique (sdn) et du succinamide (dam)

Publications (1)

Publication Number Publication Date
WO2012158180A1 true WO2012158180A1 (fr) 2012-11-22

Family

ID=44651970

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/049682 Ceased WO2012158180A1 (fr) 2011-05-18 2011-08-30 Procédés pour produire du butanediole (bdo) et du diaminobutane (dab) a partir de bouillons de fermentation contenant du succinate d'ammonium

Country Status (2)

Country Link
EP (1) EP2709978A1 (fr)
WO (1) WO2012158180A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9994505B2 (en) 2009-06-04 2018-06-12 Genomatica, Inc. Process of separating components of a fermentation broth

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6057442A (en) * 1997-09-29 2000-05-02 Basf Aktiengesellschaft Preparation of amines
JP2007254354A (ja) * 2006-03-23 2007-10-04 National Institute Of Advanced Industrial & Technology コハク酸系組成物、コハク酸ジアルキル等及びその製造方法。

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6057442A (en) * 1997-09-29 2000-05-02 Basf Aktiengesellschaft Preparation of amines
JP2007254354A (ja) * 2006-03-23 2007-10-04 National Institute Of Advanced Industrial & Technology コハク酸系組成物、コハク酸ジアルキル等及びその製造方法。

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9994505B2 (en) 2009-06-04 2018-06-12 Genomatica, Inc. Process of separating components of a fermentation broth
US10662136B2 (en) 2009-06-04 2020-05-26 Genomatica, Inc. Process of separating components of a fermentation broth

Also Published As

Publication number Publication date
EP2709978A1 (fr) 2014-03-26

Similar Documents

Publication Publication Date Title
CA2734627C (fr) Procedes de production de succinate de monoammonium a partir de bouillons de fermentation contenant du succinate de diammonium, du succinate de monoammonium et/ou de l'acide succinique,et conversion du succinate de monoammonium en acide succinique
CA2734617C (fr) Procedes de production d'acide succinique a partir de bouillons de fermentation contenant du succinate de diammonium
US8410291B2 (en) Processes for the production of hydrogenated products
US8937147B2 (en) Processes for producing diaminobutane (DAB), succinic dinitrile (SDN) and succinamide (DAM)
US20130144028A1 (en) Processes for producing diaminobutane (dab), succinic dinitrile (sdn) and succinamide (dam)
WO2011146449A1 (fr) Procédés de production de pyrrolidones
US9464030B2 (en) Processes for producing butanediol (BDO), diaminobutane (DAB), succinic dinitrile (SDN) and succinamide (DAM)
EP2571849B1 (fr) Procédés de fabrication de pyrrolidones
WO2012158180A1 (fr) Procédés pour produire du butanediole (bdo) et du diaminobutane (dab) a partir de bouillons de fermentation contenant du succinate d'ammonium
WO2013039647A1 (fr) Procédés de production d'acides carboxyliques à partir de bouillons de fermentation contenant leurs sels d'ammonium
WO2012158182A1 (fr) Procédés pour produire du butanediole et du diaminobutane a partir de bouillons de fermentation contenant du succinate d'ammonium
HK1161585A (en) Processes for producing monoammonium succinate from fermentation broths containing diammonium succinate, monoammonium succinate and/or succinic acid, and conversion of monoammonium succinate to succinic acid
EP2582657A1 (fr) Procédés de production d'hexaméthylènediamine (hmd), d'adiponitrile (adn), d'adipamide (adm), et de leurs dérivés
HK1180303A (en) Processes for producing diaminobutane (dab), succinic dinitrile (sdn) and succinamide (dam)
HK1161225A (en) Processes for producing succinic acid from fermentation broths containing diammonium succinate

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11757460

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2011757460

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 14117141

Country of ref document: US