EP1619273B1 - Verfahren zur Herstellung von 2-Alkin-1-acetalen - Google Patents

Verfahren zur Herstellung von 2-Alkin-1-acetalen Download PDF

Info

Publication number
EP1619273B1
EP1619273B1 EP05013192A EP05013192A EP1619273B1 EP 1619273 B1 EP1619273 B1 EP 1619273B1 EP 05013192 A EP05013192 A EP 05013192A EP 05013192 A EP05013192 A EP 05013192A EP 1619273 B1 EP1619273 B1 EP 1619273B1
Authority
EP
European Patent Office
Prior art keywords
general formula
alkyl
process according
alcohol
compound
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.)
Not-in-force
Application number
EP05013192A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP1619273A1 (de
Inventor
Ingo Dr. Richter
Ulrich Dr. Griesbach
Michael Dr. Becker
Roland Dr. Kessinger
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1619273A1 publication Critical patent/EP1619273A1/de
Application granted granted Critical
Publication of EP1619273B1 publication Critical patent/EP1619273B1/de
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/20—Processes
    • C25B3/23—Oxidation

Definitions

  • the present invention relates to a process for the preparation of 2-alkyne-1-acetals.
  • Non-electrochemical processes for the preparation of 2-alkyne-1-acetals are for example US 2879305 known, wherein 2-alkyne-1-aldehydes are acetalated with an alcohol.
  • the object underlying the invention was to provide an electrochemical process in order to produce 2-alkyne-1-acetals economically and in particular in high product yields and with high selectivity.
  • a process for the preparation of 2-alkyne-1-acetals of general formula I where the radicals have the following meaning R 1 : hydrogen, C 1 - to C 20 -alkyl, C 2 - to C 20 -alkenyl, C 2 - to C 20 -alkynyl, C 3 - to C 12 -cycloalkyl, C 4 - to C 20 -cycloalkyl- alkyl, C 4 - to C 10 -aryl, these radicals being optionally substituted by hydroxyl, halogen, C 1 - to C 6 -alkoxy, (C 1 - to C 6 -alkoxy) -carbonyl, carboxyl or nitrile groups can R 2 : C 1 - to C 6 -alkyl or a radical of the general formula II
  • R 1 has the abovementioned meaning
  • R 3 has the same meaning as the radical R 2 , by giving a compound of general formula III
  • R 3 is preferably a radical of the general formula II.
  • R 1 which occurs 3 times therein has preferably the same meaning.
  • the preparation is carried out in bulk, ie, no alcohol A is used but the starting compound of the general formula III occurs in terms of their function in place of the alcohol A, which acetalizes the oxidation product of the compound of general formula III.
  • preferred compounds of the general formula I are those in which hydrogen, C 1 - to C 6 -alkyl radical or a C 1 - to C 6 -alkyl radical substituted by a hydroxyl group.
  • the compounds of general formula II used are those in which the radical R 1 is hydrogen, C 1 - to C 6 -alkyl radical or a C 1 - to C 6 -alkyl radical substituted by a hydroxyl group.
  • a further very particularly preferably prepared compounds of general formula I is 1,1,4,4-tetramethoxybut-2-yn.
  • the starting materials used as compound of the general formula III are 2-butyne-1,4-diol and, as alcohol A, methanol.
  • the alcohols A and the compound of general formula III are generally bisequimolar, based on the alcoholic hydroxyl groups contained in the compound of formula III used or alcohol A is used in excess and then serves as a solvent or diluent for the compound of the general formula III and the compound of the general formula I.
  • a compound of general formula III which carries 2 or more alcoholic hydroxyl groups, per mole of hydroxyl groups, which carries the compound of general formula III, more than 2 moles (preferably 5 to 20 mol) of the alcohol A is used to a To avoid oligomerization.
  • the electrolysis solution is added to customary cosolvents.
  • these are the inert solvents generally used in organic chemistry with a high oxidation potential. Examples include dimethyl carbonate or propylene carbonate.
  • water is also suitable as a cosolvent; the proportion of water in the electrolyte is preferably less than 20% by weight.
  • Conducting salts which are contained in the electrolysis solution are generally alkali metal, tetra (C 1 - to C 6 -alkyl) ammonium, preferably tri (C 1 - to C 6 -alkyl) -methylammonium salts.
  • Suitable counterions are sulfate, bisulfate, alkyl sulfates, aryl sulfates, halides, phosphates, carbonates, alkyl phosphates, alkyl carbonates, nitrate, alcoholates, tetrafluoroborate or perchlorate.
  • acids derived from the aforementioned anions may be considered as conductive salts, e.g. Sulfuric acid, sulfonic acids and carboxylic acids.
  • suitable electrolyte salts are ionic liquids. Suitable ionic liquids are described in "Lonic Liquids in Synthesis”, ed. Peter Wasserscheid, Tom Welton, Verlag Wiley VCH, 2003, Chap. 1 to 3.
  • the process according to the invention can be carried out in all customary divided or undivided types of electrolytic cell. Preferably, one works continuously with undivided flow cells.
  • bipolar switched capillary gap cells or plate stacked cells in which the electrodes are designed as plates and are arranged plane-parallel (see. Ullmann's Encyclopedia of Industrial Chemistry, 1999 electronic release, Sixth Edition, VCH-Verlag Weinheim, Volume Electrochemistry, Chapter 3.5 , special cell designs and Chapter 5, Organic Electrochemistry, Subchapter 5.4.3.2 Cell Design).
  • the electrode material graphite is preferable.
  • the feed rate of the starting materials is generally chosen such that the weight ratio of the compounds of general formula II used to the compounds of general formula I formed in the electrolyte is 10: 1 to 0.05: 1.
  • the current densities at which the process is carried out are generally 1 to 1000, preferably 10 to 100 mA / cm 2 .
  • working at atmospheric pressure In general, working at atmospheric pressure. Higher pressures are preferably used when operating at higher temperatures to avoid boiling of the starting compounds or the solvent.
  • Suitable anode materials are, for example, noble metals such as platinum or metal oxides such as ruthenium or chromium oxide or mixed oxides of the type Ruo x Tio x and diamond electrodes. Preference is given to graphite or carbon electrodes.
  • cathode materials for example, iron, steel, stainless steel, nickel or precious metals such as platinum and graphite or carbon materials and diamond electrodes into consideration.
  • the system is graphite as the anode and cathode and graphite as the anode and nickel, stainless steel or steel as the cathode.
  • the electrolyte solution is worked up by general separation methods.
  • the electrolysis solution is generally first distilled and recovered the individual compounds in the form of different fractions separately. Further purification can be carried out, for example, by crystallization, extraction, distillation or by chromatography.
  • Example of undivided driving An undivided plate stack cell with graphite anodes and steel cathodes was used. There were 160 g of 2-propyn-1-ol in 640 g of methanol with 5.3 g of sulfuric acid at a temperature of 20 ° C within 19 h. The electrolysis was carried out at 3.4 A / dm2 and it was a charge amount of 2 F based on the used 2-propyn-1-ol passed through the cell. 8.8% areal of 1,1-dimethoxy-2-propyne (conversion 49%, yield 30%) were obtained in the electrolysis discharge.
  • Example of shared driving A split parallel plate cell with graphite anode and steel cathode was used. There were 401 g of 2-propynol in 1400 g of methanol and 38 g of MTBS (Methyltributylammoniummethylsulfat) in the anode compartment and 941 g of methanol and 24 g MTBS in the cathode compartment at a temperature of 20 ° C within 38 h. The electrolysis was carried out at 3.1 A / dm 2 and it was a charge amount of 2 F based on the used 2-propyn-1-ol passed through the cell. 8.3 GC area% of 1,1-dimethoxy-2-propyne (conversion 91%, yield 19%) were obtained in the anolyte.
  • MTBS Metaltributylammoniummethylsulfat
  • Example of shared driving A split parallel plate cell with graphite anode and steel cathode was used. There were 13 g of 2-butyne-1,4-diol in 117 g of methanol and 3.8 g of MTBS (Methyltributylammoniummethylsulfat) in the anode compartment and 130 g of methanol and 3.8 g of MTBS in the cathode compartment at a temperature of 19 ° C within 14 h implemented. The electrolysis was carried out at 3.4 A / dm 2 and it was an amount of charge of 4 F based on the 2-butyne-1,4-diol passed through the cell.
  • MTBS Metaltributylammoniummethylsulfat

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP05013192A 2004-07-23 2005-06-18 Verfahren zur Herstellung von 2-Alkin-1-acetalen Not-in-force EP1619273B1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102004035860A DE102004035860A1 (de) 2004-07-23 2004-07-23 Verfahren zur Herstellung von 2-Alkin-1 acetalen

Publications (2)

Publication Number Publication Date
EP1619273A1 EP1619273A1 (de) 2006-01-25
EP1619273B1 true EP1619273B1 (de) 2008-07-16

Family

ID=34937539

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05013192A Not-in-force EP1619273B1 (de) 2004-07-23 2005-06-18 Verfahren zur Herstellung von 2-Alkin-1-acetalen

Country Status (6)

Country Link
US (1) US20060016695A1 (ja)
EP (1) EP1619273B1 (ja)
JP (1) JP4755458B2 (ja)
CN (1) CN100585012C (ja)
AT (1) ATE401433T1 (ja)
DE (2) DE102004035860A1 (ja)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK2496735T3 (en) * 2009-11-04 2017-05-22 Ffgf Ltd PREPARATION OF CARBON HYDRADES
US9120935B2 (en) * 2011-06-21 2015-09-01 Bluestar Silicones France Sas Hydrosilylation reaction inhibitors, and use thereof for preparing stable curable silicone compositions
CN102492957B (zh) * 2011-12-15 2014-07-09 天津工业大学 一种电催化膜选择性催化氧化醇类制备醛或酸的方法
CN107964668B (zh) * 2016-10-19 2019-08-16 中国科学院上海有机化学研究所 化合物中C(sp3)-H键转化为C(sp3)-O键方法及制备得到的化合物
CN107245029B (zh) * 2017-03-14 2021-01-05 广东工业大学 一种酮类化合物及其合成方法
CN109518211B (zh) * 2019-01-08 2020-11-06 合肥工业大学 一种芳香偶酰类化合物的电化学合成方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2879305A (en) * 1959-03-24 Production of acetals of propargyl
DE2409117A1 (de) * 1974-02-26 1975-09-18 Basf Ag Verfahren zur herstellung von propiolsaeure
DE19533773A1 (de) * 1995-09-12 1997-03-13 Basf Ag Plattenstapelzelle
DE19962102A1 (de) * 1999-12-22 2001-06-28 Basf Ag Verfahren zur elektrochemischen Oxidation von organischen Verbindungen
DE10244633B3 (de) * 2002-09-25 2004-02-26 Consortium für elektrochemische Industrie GmbH Verfahren zur Herstellung von Alkincarbonsäuren durch Oxidation von Alkinalkoholen

Also Published As

Publication number Publication date
JP2006037233A (ja) 2006-02-09
EP1619273A1 (de) 2006-01-25
CN1737200A (zh) 2006-02-22
DE102004035860A1 (de) 2006-02-16
DE502005004699D1 (de) 2008-08-28
ATE401433T1 (de) 2008-08-15
CN100585012C (zh) 2010-01-27
US20060016695A1 (en) 2006-01-26
JP4755458B2 (ja) 2011-08-24

Similar Documents

Publication Publication Date Title
EP1619273B1 (de) Verfahren zur Herstellung von 2-Alkin-1-acetalen
EP0012240B1 (de) Verfahren zur Herstellung von gegebenenfalls substituierten Benzaldehyd-dialkylacetalen
DE2343054B1 (de) Verfahren zur elektrochemischen Herstellung von Pinacolen
DE2949379C2 (de) Verfahren zur Herstellung von Glyoxalsäure durch Oxidation von Glyoxal
EP2411564B1 (de) Elektrochemisches verfahern zur herstellung von 3-tert.-butylbenzaldehyd-dimethylacetal
EP1863781A1 (de) Verfahren zur herstellung von alkoxylierten 2,5-dihydrofuran- oder tetra-1,1,4,4-alkoxylierten but-2-enderivaten
EP1362022B1 (de) Verfahren zur herstellung von orthocarbonsäuretrialkylestern
EP1769103B1 (de) Elektrochemisches verfahren zur herstellung cyclopropylbenzylaminen
DE2855508A1 (de) Verfahren zur herstellung von benzaldehyden
EP0339523B1 (de) Verfahren zur Herstellung von Hydroxicarbonsäureestern
EP1913178A1 (de) Verfahren zur herstellung von 1,1,4,4-tetraalkoxy-but-2-enderivaten
EP0502372B1 (de) 4-tert-Alkyl-2-Methylbenzaldehyddialkylacetale
DE4327361A1 (de) Verfahren zur Herstellung von Benzaldehyddialkylacetalen
EP0078004B1 (de) Elektrochemisches Verfahren zur Herstellung von 2,5-Dialkoxy-2,5-dihydrofuranen
EP0152801B1 (de) Verfahren zur Herstellung von Benzaldehyddialkylacetalen
EP2534281A2 (de) Verfahren zur herstellung von 4-isopropylcyclohexylmethanol
DE3421976A1 (de) Verfahren zur herstellung von phthalaldehydacetalen
DE2851732A1 (de) Verfahren zur herstellung von substituierten benzaldehyd-dialkylacetalen
EP1206590A1 (de) Verfahren zur herstellung von in alpha-stellung oxidierten carbonylverbindungen
DE102004045029A1 (de) Verfahren zur Herstellung von Glyoxalsäurealkylesterdialkylacetal
DE10143161A1 (de) Verfahren zur Herstellung von Oxo-cyclohexyl-oder Oxo-cyclohexylenderivaten
WO2003020679A1 (de) Verfahren zur herstellung von oxo-cyclohexyl- oder oxo-cyclohexylenderivaten
DE10142220A1 (de) Verfahren zur Herstellung von Oxo-cyclohexyl- oder Oxo-cyclohexylenderivaten
DE10207238A1 (de) Verfahren zur elektroorganischen Synthese an Kohlenstoffelektroden
DE102005007286A1 (de) Elektrochemisches Verfahren zur Herstellung eines aliphatischen Orthocarbonsäureesters oder eines Orthokohlensäureesters

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

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA HR LV MK YU

17P Request for examination filed

Effective date: 20060725

AKX Designation fees paid

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR

RTI1 Title (correction)

Free format text: PROCESS FOR THE SYNTHESIS OF 2-ALKYNE-1-ACETALS

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BASF SE

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REF Corresponds to:

Ref document number: 502005004699

Country of ref document: DE

Date of ref document: 20080828

Kind code of ref document: P

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

Free format text: LANGUAGE OF EP DOCUMENT: GERMAN

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081027

Ref country code: PT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081216

Ref country code: LT

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

Ref country code: IS

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081116

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

Ref country code: BG

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081016

REG Reference to a national code

Ref country code: IE

Ref legal event code: FD4D

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

Ref country code: EE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

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

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: RO

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

Ref country code: CZ

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

Ref country code: SK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

26N No opposition filed

Effective date: 20090417

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081016

Ref country code: MC

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090618

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20081017

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20090618

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: HU

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20090117

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20110630

Year of fee payment: 7

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: TR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20110630

Year of fee payment: 7

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20080716

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20110721

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20110830

Year of fee payment: 7

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20110702

Year of fee payment: 7

Ref country code: BE

Payment date: 20110725

Year of fee payment: 7

Ref country code: IT

Payment date: 20110629

Year of fee payment: 7

BERE Be: lapsed

Owner name: BASF SE

Effective date: 20120630

REG Reference to a national code

Ref country code: NL

Ref legal event code: V1

Effective date: 20130101

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20120618

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20120618

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20130228

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 502005004699

Country of ref document: DE

Effective date: 20130101

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: 20120702

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20120630

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20120618

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20130101

Ref country code: NL

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20130101

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20120630

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20120630