CN100537031C - 有机化合物的制备方法 - Google Patents

有机化合物的制备方法 Download PDF

Info

Publication number
CN100537031C
CN100537031C CNB028262352A CN02826235A CN100537031C CN 100537031 C CN100537031 C CN 100537031C CN B028262352 A CNB028262352 A CN B028262352A CN 02826235 A CN02826235 A CN 02826235A CN 100537031 C CN100537031 C CN 100537031C
Authority
CN
China
Prior art keywords
compound
group
compounds
reaction
groups
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
CNB028262352A
Other languages
English (en)
Chinese (zh)
Other versions
CN1607980A (zh
Inventor
石井康敬
平井成尚
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.)
Daicel Corp
Original Assignee
Daicel Chemical Industries Ltd
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 Daicel Chemical Industries Ltd filed Critical Daicel Chemical Industries Ltd
Publication of CN1607980A publication Critical patent/CN1607980A/zh
Application granted granted Critical
Publication of CN100537031C publication Critical patent/CN100537031C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235Nitrogen containing compounds
    • B01J31/0245Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
    • B01J31/0249Ureas (R2N-C(=O)-NR2)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06Preparation of nitro compounds
    • C07C201/08Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06Preparation of nitro compounds
    • C07C201/12Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/30Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/48Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C07C29/50Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C07C45/34Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
    • C07C45/36Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385Saturated compounds containing a keto group being part of a ring
    • C07C49/417Saturated compounds containing a keto group being part of a ring polycyclic
    • C07C49/423Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/453Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having three rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
    • C07C49/675Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/31Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C07C51/313Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/28Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/29Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D251/00Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30Only oxygen atoms
    • C07D251/34Cyanuric or isocyanuric esters
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32Addition reactions to C=C or C-C triple bonds
    • B01J2231/323Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40Substitution 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
    • B01J2231/42Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00Systems containing at least three condensed rings
    • C07C2603/56Ring systems containing bridged rings
    • C07C2603/58Ring systems containing bridged rings containing three rings
    • C07C2603/70Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74Adamantanes
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
CNB028262352A 2001-12-25 2002-12-05 有机化合物的制备方法 Expired - Fee Related CN100537031C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001392863 2001-12-25
JP392863/2001 2001-12-25

Publications (2)

Publication Number Publication Date
CN1607980A CN1607980A (zh) 2005-04-20
CN100537031C true CN100537031C (zh) 2009-09-09

Family

ID=19188722

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB028262352A Expired - Fee Related CN100537031C (zh) 2001-12-25 2002-12-05 有机化合物的制备方法

Country Status (10)

Country Link
US (2) US7091342B2 (enExample)
EP (1) EP1459804B1 (enExample)
JP (2) JP4413009B2 (enExample)
CN (1) CN100537031C (enExample)
AU (1) AU2002361079A1 (enExample)
DE (1) DE60236619D1 (enExample)
MY (1) MY134799A (enExample)
SA (1) SA02230481B1 (enExample)
TW (1) TW200301158A (enExample)
WO (1) WO2003055600A1 (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6769128B1 (en) 1995-06-07 2004-07-27 United Video Properties, Inc. Electronic television program guide schedule system and method with data feed access
BRPI9812104B1 (pt) 1997-07-21 2016-12-27 Guide E Inc método para navegar por um guia de programa interativo
US6898762B2 (en) 1998-08-21 2005-05-24 United Video Properties, Inc. Client-server electronic program guide
CA2870324C (en) 2000-03-31 2017-08-15 United Video Properties, Inc. Systems and methods for improved audience measuring
JPWO2005023784A1 (ja) * 2003-09-02 2006-11-02 ダイセル化学工業株式会社 N,n′,n″−トリ置換イソシアヌル酸の製造方法
JP2005298380A (ja) * 2004-04-08 2005-10-27 Daicel Chem Ind Ltd 芳香族カルボン酸の製造法
JP4885468B2 (ja) * 2005-03-28 2012-02-29 株式会社ダイセル 有機化合物の製造方法
US7994330B2 (en) * 2005-03-28 2011-08-09 Daicel Chemical Industries, Ltd. Method for producing organic compound and method for decomposing compound having dicarboximide skeleton
JP2006273793A (ja) * 2005-03-30 2006-10-12 Daicel Chem Ind Ltd 環状アシルウレア系触媒を用いた有機化合物の製造方法
US8613024B2 (en) * 2005-12-13 2013-12-17 United Video Properties, Inc. Cross-platform predictive popularity ratings for use in interactive television applications
US7326815B2 (en) * 2005-12-27 2008-02-05 Exxonmobil Chemical Patents Inc. Selective oxidation of alkylbenzenes
US7834217B2 (en) * 2006-12-05 2010-11-16 Daicel Chemical Industries, Ltd. Method for producing oxidation product of cycloalkane
US7801888B2 (en) 2007-03-09 2010-09-21 Microsoft Corporation Media content search results ranked by popularity
JP5091774B2 (ja) * 2008-06-11 2012-12-05 株式会社ダイセル 酸化触媒系
US9014546B2 (en) 2009-09-23 2015-04-21 Rovi Guides, Inc. Systems and methods for automatically detecting users within detection regions of media devices
CN106008193B (zh) * 2016-06-01 2019-12-17 中国矿业大学 一种常压下使用氧气为氧化剂催化氧化褐煤的方法
US10091549B1 (en) 2017-03-30 2018-10-02 Rovi Guides, Inc. Methods and systems for recommending media assets based on the geographic location at which the media assets are frequently consumed
CN107556201B (zh) * 2017-09-08 2020-10-27 山西智创药研科技有限公司 一种制备间氨基苯酚的工艺方法
CN108525670B (zh) * 2018-05-04 2021-03-16 太原理工大学 氧化硅限域镍基催化剂及其制备方法与应用
CN112125795B (zh) * 2019-06-24 2023-08-29 中国石油化工股份有限公司 环己烷氧化制己二酸的方法
WO2021160470A1 (en) 2020-02-13 2021-08-19 Basf Se Preparation of aromatic carbonyl compounds by catalytic oxidation with molecular oxygen
CN112588083B (zh) * 2020-11-20 2022-04-22 绍兴文理学院 一种高效捕集二氧化碳的方法
CN114814065B (zh) * 2022-04-12 2023-12-01 上海交通大学 幽门螺旋杆菌的唾液中voc标志物及其在制备诊断试剂中的应用
CN115057800B (zh) * 2022-07-28 2022-11-01 山东星之联生物科技股份有限公司 对苯乙烯磺酸盐的清洁合成方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0429701A1 (en) * 1988-06-02 1991-06-05 Showa Highpolymer Co., Ltd. Curable resin composition
WO1993003825A1 (en) * 1991-08-13 1993-03-04 The Dow Chemical Company A composition and method for simultaneous absorption of sulfur dioxide and nitric oxide
JPH06199857A (ja) * 1993-01-07 1994-07-19 Taisho Pharmaceut Co Ltd 5−デアザフラボ−6,9−キノン誘導体及びその製造方法
JP2000086218A (ja) * 1998-09-05 2000-03-28 Agency Of Ind Science & Technol 超微細カーボンチューブの合成方法及びそれに用いる触媒

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5922924A (ja) * 1982-07-30 1984-02-06 Hitachi Ltd 硬化性樹脂組成物及びその硬化物
JP3434034B2 (ja) 1994-08-02 2003-08-04 ダイセル化学工業株式会社 酸化触媒およびそれを用いた酸化方法
JP2937230B2 (ja) 1994-08-02 1999-08-23 矢崎総業株式会社 コネクタ防水用シール部品
JP3911060B2 (ja) 1996-02-07 2007-05-09 ダイセル化学工業株式会社 酸化触媒系およびそれを用いた酸化方法
JPH10101905A (ja) 1996-09-27 1998-04-21 Matsushita Electric Works Ltd 封止用エポキシ樹脂組成物
JP4272720B2 (ja) 1997-01-14 2009-06-03 ダイセル化学工業株式会社 ニトロ化又はカルボキシル化用触媒、それを用いたニトロ化又はカルボキシル化方法、及びアダマンタン誘導体
JP3982872B2 (ja) * 1997-05-20 2007-09-26 ダイセル化学工業株式会社 芳香族オキシカルボン酸誘導体の製造方法
EP1055654B1 (en) 1998-12-11 2008-02-20 Daicel Chemical Industries, Ltd. Process for the preparation of organic compounds with imide catalysts
JP4555415B2 (ja) * 1999-09-01 2010-09-29 ダイセル化学工業株式会社 含窒素複素環化合物で構成された触媒、及びこの触媒を用いた有機化合物の製造法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0429701A1 (en) * 1988-06-02 1991-06-05 Showa Highpolymer Co., Ltd. Curable resin composition
WO1993003825A1 (en) * 1991-08-13 1993-03-04 The Dow Chemical Company A composition and method for simultaneous absorption of sulfur dioxide and nitric oxide
JPH06199857A (ja) * 1993-01-07 1994-07-19 Taisho Pharmaceut Co Ltd 5−デアザフラボ−6,9−キノン誘導体及びその製造方法
JP2000086218A (ja) * 1998-09-05 2000-03-28 Agency Of Ind Science & Technol 超微細カーボンチューブの合成方法及びそれに用いる触媒

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Reactions od diethyl N-alkoxyphosphoramidate anions withcarbon dioxide and carbon disulfide. MAJOR 等.J.ORG.CHEM.,Vol.30 No.4. 1964 *

Also Published As

Publication number Publication date
EP1459804A4 (en) 2005-04-06
EP1459804A1 (en) 2004-09-22
TWI300012B (enExample) 2008-08-21
EP1459804B1 (en) 2010-06-02
US7288649B2 (en) 2007-10-30
WO2003055600A1 (en) 2003-07-10
AU2002361079A1 (en) 2003-07-15
JP2009079066A (ja) 2009-04-16
JPWO2003055600A1 (ja) 2005-04-28
US20050020439A1 (en) 2005-01-27
US20060030716A1 (en) 2006-02-09
US7091342B2 (en) 2006-08-15
DE60236619D1 (de) 2010-07-15
SA02230481B1 (ar) 2009-02-07
JP4413009B2 (ja) 2010-02-10
CN1607980A (zh) 2005-04-20
MY134799A (en) 2007-12-31
JP4920024B2 (ja) 2012-04-18
TW200301158A (en) 2003-07-01

Similar Documents

Publication Publication Date Title
CN100537031C (zh) 有机化合物的制备方法
US7084090B2 (en) Catalyst comprised of n-substituted cyclic imides and processes for preparing organic compounds with the catalyst
JP4079773B2 (ja) N−置換環状イミド化合物で構成された触媒、及びこの触媒を用いた有機化合物の製造法
CN101626835B (zh) 环状酰亚胺固定化催化剂、及用该催化剂的有机化合物氧化方法
US7368615B2 (en) Catalyst comprising a cyclic imide compound and process for producing organic compounds using the catalyst
JP4095281B2 (ja) 有機化合物製造用触媒、及びこの触媒を用いた有機化合物の製造法
JP4112877B2 (ja) 環状イミド系化合物で構成された触媒、及びこの触媒を用いた有機化合物の製造法
JP4841468B2 (ja) 窒素原子含有環状化合物で構成された触媒、及びそれを用いた有機化合物の酸化方法
JP4885468B2 (ja) 有機化合物の製造方法
US7994330B2 (en) Method for producing organic compound and method for decomposing compound having dicarboximide skeleton
JP2006273793A (ja) 環状アシルウレア系触媒を用いた有機化合物の製造方法
EP1870394A1 (en) Method for producing organic compound and method for decomposing compound having dicarboxyimide skeleton

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C56 Change in the name or address of the patentee
CP01 Change in the name or title of a patent holder

Address after: Osaka Japan

Patentee after: Daicel Chem

Address before: Osaka Japan

Patentee before: Daicel Chemical Industries Co., Ltd.

CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20090909

Termination date: 20181205

CF01 Termination of patent right due to non-payment of annual fee