DE19620023C2 - Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane - Google Patents

Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane

Info

Publication number
DE19620023C2
DE19620023C2 DE19620023A DE19620023A DE19620023C2 DE 19620023 C2 DE19620023 C2 DE 19620023C2 DE 19620023 A DE19620023 A DE 19620023A DE 19620023 A DE19620023 A DE 19620023A DE 19620023 C2 DE19620023 C2 DE 19620023C2
Authority
DE
Germany
Prior art keywords
formula
acid
tertiary
phosphinate
alkaline earth
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.)
Expired - Fee Related
Application number
DE19620023A
Other languages
German (de)
English (en)
Other versions
DE19620023A1 (de
Inventor
Thomas Seitz
Steffen Haber
Hans-Jerg Kleiner
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.)
Celanese Sales Germany GmbH
Original Assignee
Celanese Chemicals Europe GmbH
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 to DE19620023A priority Critical patent/DE19620023C2/de
Application filed by Celanese Chemicals Europe GmbH filed Critical Celanese Chemicals Europe GmbH
Priority to KR1019980700569A priority patent/KR19990035908A/ko
Priority to CZ0021298A priority patent/CZ297891B6/cs
Priority to ES96927595T priority patent/ES2150688T3/es
Priority to US09/000,128 priority patent/US6140265A/en
Priority to ES96927594T priority patent/ES2163649T3/es
Priority to CZ98211A priority patent/CZ21198A3/cs
Priority to KR1019980700570A priority patent/KR19990035909A/ko
Priority to JP50721997A priority patent/JP3989955B2/ja
Priority to EP96927595A priority patent/EP0842145B1/de
Priority to EP96927594A priority patent/EP0842183B1/de
Priority to US08/686,167 priority patent/US5756804A/en
Priority to DE59605626T priority patent/DE59605626D1/de
Priority to HU9900235A priority patent/HUP9900235A3/hu
Priority to PCT/EP1996/003267 priority patent/WO1997005104A1/de
Priority to JP9507218A priority patent/JPH11509776A/ja
Priority to HU9900423A priority patent/HU225303B1/hu
Priority to PCT/EP1996/003266 priority patent/WO1997005151A1/de
Priority to DE59607957T priority patent/DE59607957D1/de
Priority to EP97107705A priority patent/EP0807637B1/de
Priority to DE59706357T priority patent/DE59706357D1/de
Priority to US08/857,755 priority patent/US5801263A/en
Priority to JP9127641A priority patent/JPH1045781A/ja
Publication of DE19620023A1 publication Critical patent/DE19620023A1/de
Application granted granted Critical
Publication of DE19620023C2 publication Critical patent/DE19620023C2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/006—Palladium compounds
    • C07F15/0066—Palladium compounds without a metal-carbon linkage
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0257—Phosphorus acids or phosphorus acid esters
    • B01J31/0259—Phosphorus acids or phosphorus acid esters comprising phosphorous acid (-ester) groups ((RO)P(OR')2) or the isomeric phosphonic acid (-ester) groups (R(R'O)2P=O), i.e. R= C, R'= C, H
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0257—Phosphorus acids or phosphorus acid esters
    • B01J31/0261—Phosphorus acids or phosphorus acid esters comprising phosphonous acid (-ester) groups (RP(OR')2) or the isomeric phosphinic acid (-ester) groups (R2(R'O)P=O), i.e. R= C, R'= C, H
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2495—Ligands comprising a phosphine-P atom and one or more further complexing phosphorus atoms covered by groups B01J31/1845 - B01J31/1885, e.g. phosphine/phosphinate or phospholyl/phosphonate ligands
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3229—Esters of aromatic acids (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/505—Preparation; Separation; Purification; Stabilisation
    • C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
    • C07F9/5077—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure P-Metal, including R2P-M+
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
DE19620023A 1995-07-25 1996-05-17 Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane Expired - Fee Related DE19620023C2 (de)

Priority Applications (23)

Application Number Priority Date Filing Date Title
DE19620023A DE19620023C2 (de) 1996-05-17 1996-05-17 Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane
HU9900235A HUP9900235A3 (en) 1995-07-25 1996-07-24 Method of carrying out cross-coupling reactions
ES96927595T ES2150688T3 (es) 1995-07-25 1996-07-24 Procedimiento para la realizacion de reacciones de acoplamiento cruzado.
US09/000,128 US6140265A (en) 1995-07-25 1996-07-24 Catalyst for cross-coupling reactions
ES96927594T ES2163649T3 (es) 1995-07-25 1996-07-24 Catalizadores para la realizacion de reacciones de acoplamiento cruzado.
CZ98211A CZ21198A3 (cs) 1995-07-25 1996-07-24 Katalyzátory k provádění křížových kopulačních reakcí
KR1019980700570A KR19990035909A (ko) 1995-07-25 1996-07-24 교차-커플링 반응용 촉매
JP50721997A JP3989955B2 (ja) 1995-07-25 1996-07-24 クロス・カップリング反応を実施する方法
EP96927595A EP0842145B1 (de) 1995-07-25 1996-07-24 Verfahren zur durchführung von kreuzkupplungsreaktionen
CZ0021298A CZ297891B6 (cs) 1995-07-25 1996-07-24 Zpusob výroby vícejaderných aromatických sloucenin
US08/686,167 US5756804A (en) 1995-07-25 1996-07-24 Homogeneous process for carrying out cross-coupling reactions
JP9507218A JPH11509776A (ja) 1995-07-25 1996-07-24 交差カップリング反応用触媒
KR1019980700569A KR19990035908A (ko) 1995-07-25 1996-07-24 교차-커플링 반응의 실시방법
PCT/EP1996/003267 WO1997005104A1 (de) 1995-07-25 1996-07-24 Verfahren zur durchführung von kreuzkupplungsreaktionen
DE59605626T DE59605626D1 (de) 1995-07-25 1996-07-24 Verfahren zur durchführung von kreuzkupplungsreaktionen
HU9900423A HU225303B1 (en) 1995-07-25 1996-07-24 Catalyst system for cross-coupling reactions
PCT/EP1996/003266 WO1997005151A1 (de) 1995-07-25 1996-07-24 Katalysatoren zur durchführung von kreuzkupplungsreaktionen
DE59607957T DE59607957D1 (de) 1995-07-25 1996-07-24 Katalysatoren zur durchführung von kreuzkupplungsreaktionen
EP96927594A EP0842183B1 (de) 1995-07-25 1996-07-24 Katalysatoren zur durchführung von kreuzkupplungsreaktionen
EP97107705A EP0807637B1 (de) 1996-05-17 1997-05-12 Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane
DE59706357T DE59706357D1 (de) 1996-05-17 1997-05-12 Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane
US08/857,755 US5801263A (en) 1996-05-17 1997-05-15 Process for preparing tertiary phosphines containing phosphinate or phosphonate groups, and novel tertiary phosphines containing phosphinate groups
JP9127641A JPH1045781A (ja) 1996-05-17 1997-05-16 ホスフィネート− 又はホスホネート基を含有する第三ホスフィンの製造方法及びホスフィネート基を含有する新規第三ホスフィン

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19620023A DE19620023C2 (de) 1996-05-17 1996-05-17 Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane

Publications (2)

Publication Number Publication Date
DE19620023A1 DE19620023A1 (de) 1997-11-20
DE19620023C2 true DE19620023C2 (de) 2001-03-08

Family

ID=7794636

Family Applications (2)

Application Number Title Priority Date Filing Date
DE19620023A Expired - Fee Related DE19620023C2 (de) 1995-07-25 1996-05-17 Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane
DE59706357T Expired - Fee Related DE59706357D1 (de) 1996-05-17 1997-05-12 Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE59706357T Expired - Fee Related DE59706357D1 (de) 1996-05-17 1997-05-12 Verfahren zur Herstellung von Phosphinat- oder Phosphonatgruppen enthaltenden tertiären Phosphanen und neue Phosphinatgruppen enthaltende tertiäre Phosphane

Country Status (4)

Country Link
US (1) US5801263A (enExample)
EP (1) EP0807637B1 (enExample)
JP (1) JPH1045781A (enExample)
DE (2) DE19620023C2 (enExample)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997005184A1 (en) * 1995-07-28 1997-02-13 The Dow Chemical Company 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers
FR2750423B1 (fr) * 1996-06-28 1998-08-14 Rhone Poulenc Chimie Procede d'hydrogenation asymetrique d'un compose cetonique
GB9807104D0 (en) * 1998-04-02 1998-06-03 Chirotech Technology Ltd The preparation of phosphine ligands
US6124462A (en) 1999-11-30 2000-09-26 E. I. Du Pont De Nemours And Company Catalysis using phosphine oxide compounds
EP1132361B1 (en) * 2000-03-06 2003-05-14 Solvias AG Coupling of nucleophiles, vinyl compounds or CO with water, alcohols or amines to organic compounds
US20030220646A1 (en) * 2002-05-23 2003-11-27 Thelen Sarah L. Method and apparatus for reducing femoral fractures
JP2004501877A (ja) 2000-06-26 2004-01-22 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ホスフィンオキシド化合物およびスルホキシド化合物を用いる触媒作用
JP4005800B2 (ja) * 2001-12-10 2007-11-14 高砂香料工業株式会社 新規不斉ホスフィン配位子
US6878850B2 (en) 2003-01-29 2005-04-12 Combiphos Catalysts, Inc Catalysis using halophosphine compounds
US7854269B2 (en) * 2005-04-01 2010-12-21 The Viking Corporation Sprinkler assembly
US7465795B2 (en) * 2005-12-20 2008-12-16 Astrazeneca Ab Compounds and uses thereof
KR20080080206A (ko) * 2005-12-20 2008-09-02 아스트라제네카 아베 Ｇａｂａａ-수용체 조절제로서의 치환된 신놀린 유도체 및그의 합성 방법
AR067028A1 (es) * 2007-06-19 2009-09-30 Astrazeneca Ab Compuestos y usos de los mismos 849

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3992273A (en) * 1975-10-09 1976-11-16 Monsanto Company Method of preparing substituted phenyl phosphinic acids
GB9017482D0 (en) * 1990-08-09 1990-09-26 Ici Plc Manufacturing process
ES2130321T3 (es) * 1993-10-08 1999-07-01 Hoffmann La Roche Compuestos de fosforo opticamente activos.
CZ297891B6 (cs) * 1995-07-25 2007-04-25 Archimica Gmbh Zpusob výroby vícejaderných aromatických sloucenin

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J. Chem. Soc. Perkin Trans (1995) 1145 *
Synthesis 9 (1984) 778 *

Also Published As

Publication number Publication date
DE59706357D1 (de) 2002-03-21
US5801263A (en) 1998-09-01
EP0807637A1 (de) 1997-11-19
JPH1045781A (ja) 1998-02-17
DE19620023A1 (de) 1997-11-20
EP0807637B1 (de) 2002-02-13

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OP8 Request for examination as to paragraph 44 patent law
8127 New person/name/address of the applicant

Owner name: CELANESE CHEMICALS EUROPE GMBH, 60439 FRANKFURT, D

D2 Grant after examination
8364 No opposition during term of opposition
8339 Ceased/non-payment of the annual fee