[go: up one dir, main page]

WO2010085712A3 - Methods for producing dodecanedioic acid and derivatives thereof - Google Patents

Methods for producing dodecanedioic acid and derivatives thereof Download PDF

Info

Publication number
WO2010085712A3
WO2010085712A3 PCT/US2010/021894 US2010021894W WO2010085712A3 WO 2010085712 A3 WO2010085712 A3 WO 2010085712A3 US 2010021894 W US2010021894 W US 2010021894W WO 2010085712 A3 WO2010085712 A3 WO 2010085712A3
Authority
WO
WIPO (PCT)
Prior art keywords
acid
dodecanedioic acid
dodecanedioic
methods
nylon
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/US2010/021894
Other languages
French (fr)
Other versions
WO2010085712A2 (en
Inventor
John W. Frost
James Millis
Zhenyu Tang
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.)
Draths Corp
Original Assignee
Draths Corp
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
Application filed by Draths Corp filed Critical Draths Corp
Priority to EP10701303A priority Critical patent/EP2389349A2/en
Priority to JP2011548161A priority patent/JP2012515795A/en
Priority to CN2010800097134A priority patent/CN102498086A/en
Publication of WO2010085712A2 publication Critical patent/WO2010085712A2/en
Publication of WO2010085712A3 publication Critical patent/WO2010085712A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
    • 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

Landscapes

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

Abstract

Methods for producing biosourced dodecanedioic acid and compositions comprising biosourced dodecanedioic acid are provided. In some embodiments, the method comprises first forming muconic acid biologically from a renewable carbon source, reducing the muconic acid to hexenedioic acid, and then reacting the hexenedioic acid with an unsaturated fatty acid, typically a Δ9 unsaturated fatty acid, in a metathesis reaction to produce dodecenedioic acid. Dodecenedioic acid is then reduced to dodecanedioic acid. Dodecanedioic acid is can be used to form polymers, such as polyamides. Examples of polyamides include nylon, such as nylon 6,12. Nylon 6,12 can be formed by reacting dodecanedioic acid with 1,6-hexamethylene diamine.
PCT/US2010/021894 2009-01-22 2010-01-22 Methods for producing dodecanedioic acid and derivatives thereof Ceased WO2010085712A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP10701303A EP2389349A2 (en) 2009-01-22 2010-01-22 Methods for producing dodecanedioic acid and derivatives thereof
JP2011548161A JP2012515795A (en) 2009-01-22 2010-01-22 Method for producing dodecanedioic acid and its derivatives
CN2010800097134A CN102498086A (en) 2009-01-22 2010-01-22 Process for producing dodecanedioic acid and derivatives thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14654509P 2009-01-22 2009-01-22
US61/146,545 2009-01-22

Publications (2)

Publication Number Publication Date
WO2010085712A2 WO2010085712A2 (en) 2010-07-29
WO2010085712A3 true WO2010085712A3 (en) 2010-09-16

Family

ID=42238600

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/021894 Ceased WO2010085712A2 (en) 2009-01-22 2010-01-22 Methods for producing dodecanedioic acid and derivatives thereof

Country Status (5)

Country Link
EP (1) EP2389349A2 (en)
JP (1) JP2012515795A (en)
KR (1) KR20110125221A (en)
CN (1) CN102498086A (en)
WO (1) WO2010085712A2 (en)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010010984A1 (en) * 2010-03-10 2011-09-15 Emery Oleochemicals Gmbh Process for the preparation of dicarboxylic acids or dicarboxylic esters by metathesis
WO2012082727A1 (en) * 2010-12-15 2012-06-21 Amyris, Inc. Biobased polyamides
BR112013023848A2 (en) * 2011-03-18 2018-07-03 Mitsubishi Chem Corp method for producing polymer, method for producing organic acid, and organic acid producing microorganism.
US9073867B2 (en) 2011-04-09 2015-07-07 Amyris, Inc. Process for preparing caprolactam and polyamides therefrom
US8728798B2 (en) 2011-05-03 2014-05-20 Verdezyne, Inc. Biological methods for preparing adipic acid
BR112014030912A2 (en) * 2012-06-12 2017-06-27 Elevance Renewable Sciences methods for suppressing dehydrogenation
WO2014007273A1 (en) 2012-07-03 2014-01-09 株式会社ジナリス Useful microorganism, and method for producing desired substance
CN103667166A (en) * 2012-09-21 2014-03-26 天津工业生物技术研究所 Escherichia coli for producing adipic acid precursor namely cis,cis-muconic acid and application of escherichia coli
CN103087310B (en) * 2013-01-14 2014-10-15 金发科技股份有限公司 Polyamide resin and application thereof as well as polyamide composition consisting of same
CN103145979B (en) * 2013-02-26 2015-07-29 上海凯赛生物技术研发中心有限公司 A kind of nylon and preparation method thereof
CN103147152B (en) * 2013-02-26 2015-01-21 上海凯赛生物技术研发中心有限公司 Nylon fiber
CN103146190B (en) * 2013-02-26 2015-03-11 上海凯赛生物技术研发中心有限公司 Nylon film
CN103146189B (en) * 2013-02-26 2015-11-18 上海凯赛生物技术研发中心有限公司 A kind of modified nylon plastics
EP3080190A1 (en) * 2013-12-13 2016-10-19 Basf Se Process for producing nylon-6,6
KR20170078678A (en) * 2014-10-28 2017-07-07 미리안트 코포레이션 Polymers from muconic acid isomers and its derivatives
TWI609108B (en) * 2014-10-29 2017-12-21 財團法人紡織產業綜合研究所 Method of controlling amino-group content of nylon
CA2966147A1 (en) 2014-10-30 2016-05-06 Toray Industries, Inc. Method for producing .epsilon.-caprolactam
DE102018209522A1 (en) * 2018-06-14 2019-12-19 Continental Reifen Deutschland Gmbh Reinforcement cord for elastomeric products, in particular for pneumatic vehicle tires, and elastomeric product
CN111349660B (en) * 2018-12-24 2022-05-31 中国科学院微生物研究所 Preparation method of long-chain dibasic acid
FI128954B (en) 2019-09-26 2021-03-31 Neste Oyj Renewable base oil production engaging metathesis
FI128952B (en) 2019-09-26 2021-03-31 Neste Oyj Renewable alkene production engaging metathesis
FI128953B (en) * 2019-09-26 2021-03-31 Neste Oyj Renewable chemical production engaging metathesis and microbial oxidation
CN110818564A (en) * 2019-11-21 2020-02-21 石河子大学 A kind of method utilizing unsaturated fatty acid ester to prepare high carbon dibasic acid ester
CN113582832B (en) * 2021-09-13 2024-01-26 深圳瑞德林生物技术有限公司 Preparation method of long-chain diacid
CN115537369B (en) * 2022-11-09 2024-03-01 云南农业大学 Application of 2-dodecenedioic acid in promoting pseudomonas mongolica growth and colonisation

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4788333A (en) * 1985-01-07 1988-11-29 E. I. Du Pont De Nemours And Company Hydrocarboxylation of unsaturated carboxylic acids to linear dicarboxylic acids
US5705144A (en) * 1992-09-30 1998-01-06 Unilever Patent Holdings B.V. Cosmetic composition containing retinol and dioic acid
EP1251135A2 (en) * 1992-04-03 2002-10-23 California Institute Of Technology High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof
WO2008048520A2 (en) * 2006-10-13 2008-04-24 Elevance Renewable Sciences, Inc. Methods of making organic compounds by metathesis and hydrocyanation
DE102008002092A1 (en) * 2008-05-30 2009-12-03 Evonik Degussa Gmbh A process for the preparation of dodeca-2, 10-diene-1, 12-dicarboxylic acid or 1, 12-dodecanedicarboxylic acid by means of ring-opening cross-metathesis (ROCM) of cyclooctene with acrylic acid

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3903152A (en) 1972-07-04 1975-09-02 Toa Gosei Chem Ind Process for producing highly pure 1,12-dodecanedioic acid
US5487987A (en) 1993-09-16 1996-01-30 Purdue Research Foundation Synthesis of adipic acid from biomass-derived carbon sources
US6428767B1 (en) 1995-05-12 2002-08-06 E. I. Du Pont De Nemours And Company Method for identifying the source of carbon in 1,3-propanediol
NL1009846C2 (en) 1998-08-12 2000-02-15 Dsm Nv Polyamide product from polytetramethylene diacid amide.
US7531593B2 (en) 2006-10-31 2009-05-12 E.I. Du Pont De Nemours And Company Thermoplastic elastomer blend composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4788333A (en) * 1985-01-07 1988-11-29 E. I. Du Pont De Nemours And Company Hydrocarboxylation of unsaturated carboxylic acids to linear dicarboxylic acids
EP1251135A2 (en) * 1992-04-03 2002-10-23 California Institute Of Technology High activity ruthenium or osmium metal carbene complexes for olefin metathesis reactions and synthesis thereof
US5705144A (en) * 1992-09-30 1998-01-06 Unilever Patent Holdings B.V. Cosmetic composition containing retinol and dioic acid
WO2008048520A2 (en) * 2006-10-13 2008-04-24 Elevance Renewable Sciences, Inc. Methods of making organic compounds by metathesis and hydrocyanation
DE102008002092A1 (en) * 2008-05-30 2009-12-03 Evonik Degussa Gmbh A process for the preparation of dodeca-2, 10-diene-1, 12-dicarboxylic acid or 1, 12-dodecanedicarboxylic acid by means of ring-opening cross-metathesis (ROCM) of cyclooctene with acrylic acid

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Undecylenic acid", INTERNET CITATION, 20 September 2008 (2008-09-20), XP007913938 *
ELVIDGE J A ET AL: "143. Polyene acids. Part V. Catalytic semi-hydrogenation of the three isomeric muconic acids and comfirmation of their configurations", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY, LETCHWORTH; GB LNKD- DOI:10.1039/JR9530000708, 1 January 1953 (1953-01-01), pages 708 - 712, XP009136284, ISSN: 0368-1769 *

Also Published As

Publication number Publication date
CN102498086A (en) 2012-06-13
KR20110125221A (en) 2011-11-18
JP2012515795A (en) 2012-07-12
WO2010085712A2 (en) 2010-07-29
EP2389349A2 (en) 2011-11-30

Similar Documents

Publication Publication Date Title
WO2010085712A3 (en) Methods for producing dodecanedioic acid and derivatives thereof
MX2011004049A (en) Ethanol production by microorganisms.
WO2010001078A3 (en) Production of alkenes by enzymatic decarboxylation of 3-hydroxyalkanoic acids
MY163070A (en) Process to produce valerolactone from levulinic acid
EA201100156A1 (en) OBTAINING DICARBONIC ACIDS AT LOW PH
WO2014105794A3 (en) Methods of producing 7-carbon chemicals via methyl-ester shielded carbon chain elongation
IL196894A0 (en) Process for preparing 3-dihalomethylpyrazole-4-carboxylic acid derivatives
MY148096A (en) 4,5-diphenyl-pyrimidinyl-amino substituted carboxylic acids, method for the production and use thereof as medicaments
MX2009001004A (en) Novel engineered microorganism producing homo-succinic acid and method for preparing succinic acid using the same.
WO2012052265A3 (en) Stabilized, pure lithium metal powder and method for producing the same
WO2013011292A3 (en) Microorganism for converting carbon dioxide to aliphatic carboxylic acids via formic acid intermediate
RU2011115094A (en) METHOD FOR PRODUCING POLYAMIDE
PH12012502480A1 (en) Method for producing polylactic acid
WO2011031023A3 (en) Method for producing cyclicised compounds from organic acids having from 4 to 6 carbon atoms
ATE532813T1 (en) HYDROLYSIS-STABLE POLYAMIDES
MY149033A (en) Biaxially stretched polyamide resin film, and process for production thereof
EP2394979A8 (en) Intermediate of cilastatin and preparation method thereof
PH12012501042A1 (en) Process for production of polyamide
EP4282972A3 (en) Production of branched chain fatty acids and derivatives thereof in recombinant microbial cells
MX2010005938A (en) Method for the production of 2-fluoroacyl-3-amino-acrylic acid derivatives.
RU2015118163A (en) A NEW ALICYCLIC DIOL COMPOUND AND METHOD FOR PRODUCING IT
MY161118A (en) Use of methanesulfonic acid for producing fatty acid esters
WO2009124966A3 (en) Conversion of stilbenoids
ATE462693T1 (en) METHOD FOR PRODUCING REMIFENTANIL, INTERMEDIATE PRODUCTS THEREOF, USE OF THESE INTERMEDIATE PRODUCTS AND METHOD FOR THE PRODUCTION THEREOF
MY157695A (en) Process for preparing polyols from renewable raw materials

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 201080009713.4

Country of ref document: CN

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

Ref document number: 10701303

Country of ref document: EP

Kind code of ref document: A2

WWE Wipo information: entry into national phase

Ref document number: 3022/KOLNP/2011

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2011548161

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2010701303

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 20117019342

Country of ref document: KR

Kind code of ref document: A

REG Reference to national code

Ref country code: BR

Ref legal event code: B01E

Ref document number: PI1005364

Country of ref document: BR

ENPW Started to enter national phase and was withdrawn or failed for other reasons

Ref document number: PI1005364

Country of ref document: BR

Free format text: PEDIDO RETIRADO EM RELACAO AO BRASIL POR NAO ATENDER AS DETERMINACOES REFERENTES A ENTRADA DO PEDIDO NA FASE NACIONAL E POR NAO TER CUMPRIDO EXIGENCIA FORMULADA NA RPI NO 2433, DE 22/08/2017.

Ref document number: PI1005364

Country of ref document: BR