NL9000992A - Werkwijze voor het katalytisch in een wervelbed omzetten van een hoofdzakelijk methaan bevattende lichte koolwaterstoftoevoer in synthesegas. - Google Patents
Werkwijze voor het katalytisch in een wervelbed omzetten van een hoofdzakelijk methaan bevattende lichte koolwaterstoftoevoer in synthesegas. Download PDFInfo
- Publication number
- NL9000992A NL9000992A NL9000992A NL9000992A NL9000992A NL 9000992 A NL9000992 A NL 9000992A NL 9000992 A NL9000992 A NL 9000992A NL 9000992 A NL9000992 A NL 9000992A NL 9000992 A NL9000992 A NL 9000992A
- Authority
- NL
- Netherlands
- Prior art keywords
- catalyst
- methane
- synthesis gas
- alumina
- alpha
- Prior art date
Links
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims description 126
- 238000000034 method Methods 0.000 title claims description 51
- 230000015572 biosynthetic process Effects 0.000 title claims description 46
- 238000003786 synthesis reaction Methods 0.000 title claims description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims description 117
- 239000007789 gas Substances 0.000 claims description 70
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 68
- 238000006243 chemical reaction Methods 0.000 claims description 65
- 239000002245 particle Substances 0.000 claims description 63
- 230000008569 process Effects 0.000 claims description 31
- 229910052759 nickel Inorganic materials 0.000 claims description 29
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 28
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 18
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 230000001737 promoting effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- 238000000227 grinding Methods 0.000 description 16
- 239000010419 fine particle Substances 0.000 description 15
- 238000005299 abrasion Methods 0.000 description 11
- 238000009434 installation Methods 0.000 description 9
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 6
- 230000002441 reversible effect Effects 0.000 description 6
- 230000036961 partial effect Effects 0.000 description 5
- 238000000629 steam reforming Methods 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000003628 erosive effect Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000002918 waste heat Substances 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002459 porosimetry Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000002407 reforming Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- -1 methane Chemical class 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000003921 particle size analysis Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006057 reforming reaction Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/32—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air
- C01B3/34—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents
- C01B3/38—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents using catalysts
- C01B3/40—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents using catalysts characterised by the catalyst
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/32—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air
- C01B3/34—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents
- C01B3/38—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents using catalysts
- C01B3/42—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents using catalysts using moving solid particles
- C01B3/44—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents using catalysts using moving solid particles using the fluidised bed technique
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogen, Water And Hydrids (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US35723389 | 1989-05-26 | ||
US07/357,233 US4888131A (en) | 1988-03-28 | 1989-05-26 | Synthesis gas preparation and catalyst therefor |
Publications (1)
Publication Number | Publication Date |
---|---|
NL9000992A true NL9000992A (nl) | 1990-12-17 |
Family
ID=23404811
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NL9000992A NL9000992A (nl) | 1989-05-26 | 1990-04-25 | Werkwijze voor het katalytisch in een wervelbed omzetten van een hoofdzakelijk methaan bevattende lichte koolwaterstoftoevoer in synthesegas. |
Country Status (6)
Country | Link |
---|---|
US (1) | US4888131A (no) |
AU (1) | AU619983B2 (no) |
CA (1) | CA2014946C (no) |
MY (1) | MY106754A (no) |
NL (1) | NL9000992A (no) |
NO (1) | NO902050L (no) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1333008C (en) * | 1988-03-28 | 1994-11-15 | Duane Arlen Goetsch | Synthesis gas preparation and catalyst therefor |
US5026934A (en) * | 1990-02-12 | 1991-06-25 | Lyondell Petrochemical Company | Method for converting light hydrocarbons to olefins, gasoline and methanol |
GB2249555A (en) * | 1990-11-09 | 1992-05-13 | Shell Int Research | Partial oxidation of a hydrocarbon-containing fuel using entrained catalyst |
US5160456A (en) * | 1991-06-07 | 1992-11-03 | Exxon Research And Engineering Company | Catalyst/heat-transfer medium for syngas generation |
US5143647A (en) * | 1991-06-07 | 1992-09-01 | Exxon Research And Engineering Company | Synthesis gas generation startup process (C-2556) |
CA2081170C (en) * | 1992-10-22 | 2002-12-24 | Alaa-Eldin Moustafa Adris | Fluidized bed reaction system for steam/hydrocarbon gas reforming to produce hydrogen |
US5395813A (en) * | 1993-05-11 | 1995-03-07 | Exxon Research And Engineering Company | Particulate solids for catalyst supports and heat transfer materials |
US5360778A (en) * | 1993-05-11 | 1994-11-01 | Exxon Research And Engineering Company | High surface purity heat transfer solids for high temperature fluidized bed reactions |
US5494653A (en) * | 1993-08-27 | 1996-02-27 | Battelle Memorial Institute | Method for hot gas conditioning |
US6293979B1 (en) | 1994-12-19 | 2001-09-25 | Council Of Scientific & Industrial Research | Process for the catalytic conversion of methane or natural gas to syngas or a mixture of carbon monoxide and hydrogen |
US5635541A (en) * | 1995-06-12 | 1997-06-03 | Air Products And Chemicals, Inc. | Elevated pressure air separation unit for remote gas process |
US6284807B1 (en) | 1995-08-08 | 2001-09-04 | Exxon Research And Engineering Company | Slurry hydrocarbon synthesis process with increased catalyst life |
US5985178A (en) * | 1997-10-31 | 1999-11-16 | Exxon Research And Engineering Co. | Low hydrogen syngas using CO2 and a nickel catalyst |
US5882614A (en) * | 1998-01-23 | 1999-03-16 | Exxon Research And Engineering Company | Very low sulfur gas feeds for sulfur sensitive syngas and hydrocarbon synthesis processes |
DE19827154C2 (de) * | 1998-06-18 | 2003-01-30 | Irt Innovative Recycling Techn | Verfahren zur Herstellung von Methanol aus Biogas sowie eine Vorrichtung zur Durchführung des Verfahrens |
US6706661B1 (en) * | 2000-09-01 | 2004-03-16 | Exxonmobil Research And Engineering Company | Fischer-Tropsch catalyst enhancement |
US6787496B2 (en) | 2002-01-29 | 2004-09-07 | Exxonmobil Research And Engineering Company | Supported catalyst treatment |
US6753354B2 (en) | 2002-01-29 | 2004-06-22 | Exxonmobil Research And Engineering Company | Fischer-tropsch catalyst enhancement |
US6777451B2 (en) | 2002-01-29 | 2004-08-17 | Exxonmobil Research And Engineering Company | Catalyst enhancement |
US6800579B2 (en) | 2002-01-29 | 2004-10-05 | Exxonmobil Research And Engineering Company | Catalyst regeneration |
US6753286B2 (en) | 2002-01-29 | 2004-06-22 | Exxonmobil Research And Engineering Company | Supported catalyst regeneration |
US7255840B2 (en) * | 2003-06-26 | 2007-08-14 | Praxair Technology, Inc. | Autothermal reactor and method for production of synthesis gas |
MY140997A (en) * | 2004-07-22 | 2010-02-12 | Shell Int Research | Process for the removal of cos from a synthesis gas stream comprising h2s and cos |
US8043589B2 (en) * | 2006-01-18 | 2011-10-25 | Shell Oil Company | Process for removing carbonyl sulphide and hydrogen sulphide from a synthesis gas stream |
US8592492B2 (en) * | 2010-03-08 | 2013-11-26 | Praxair Technology, Inc. | Using fossil fuels to increase biomass-based fuel benefits |
US9290422B2 (en) | 2012-11-27 | 2016-03-22 | Praxair Technology, Inc. | Hybrid plant for liquid fuel production |
US9145525B2 (en) | 2013-06-26 | 2015-09-29 | Praxair Technology, Inc. | Acid gas management in liquid fuel production process |
RU2554008C1 (ru) | 2014-01-13 | 2015-06-20 | Общество с ограниченной ответственностью "Газохим Техно" | Реактор для парциального окисления углеводородных газов |
JP2023546069A (ja) | 2020-10-13 | 2023-11-01 | エクソンモービル テクノロジー アンド エンジニアリング カンパニー | サイクル・フロー・リアクターにおける改質用触媒系 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3014787A (en) * | 1959-06-08 | 1961-12-26 | Exxon Research Engineering Co | Production of hydrogen and carbon monoxide |
US3138438A (en) * | 1960-06-01 | 1964-06-23 | Renault | Methods for converting methane |
EP0084273A2 (en) * | 1982-01-04 | 1983-07-27 | The Standard Oil Company | Production of synthesis gas |
US4474230A (en) * | 1982-08-31 | 1984-10-02 | Foster Wheeler Energy Corporation | Fluidized bed reactor system |
EP0335668A2 (en) * | 1988-03-28 | 1989-10-04 | Exxon Research And Engineering Company | Method and catalyst for synthesis gas preparation |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3119667A (en) * | 1961-01-31 | 1964-01-28 | Pullman Inc | Process for hydrogen production |
US3232726A (en) * | 1962-03-28 | 1966-02-01 | Pullman Inc | Quenching |
US3524819A (en) * | 1967-03-03 | 1970-08-18 | Lummus Co | Steam reforming of hydrocarbons |
FR2027762A1 (fr) * | 1969-01-04 | 1970-10-02 | Basf Ag | Procede de reformage a la vapeur d'eau d'hydrocarbures gazeux,notamment de methane |
-
1989
- 1989-05-26 US US07/357,233 patent/US4888131A/en not_active Expired - Lifetime
-
1990
- 1990-04-19 CA CA002014946A patent/CA2014946C/en not_active Expired - Fee Related
- 1990-04-25 NL NL9000992A patent/NL9000992A/nl active Search and Examination
- 1990-05-09 NO NO90902050A patent/NO902050L/no unknown
- 1990-05-24 AU AU55897/90A patent/AU619983B2/en not_active Ceased
- 1990-05-26 MY MYPI90000855A patent/MY106754A/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3014787A (en) * | 1959-06-08 | 1961-12-26 | Exxon Research Engineering Co | Production of hydrogen and carbon monoxide |
US3138438A (en) * | 1960-06-01 | 1964-06-23 | Renault | Methods for converting methane |
EP0084273A2 (en) * | 1982-01-04 | 1983-07-27 | The Standard Oil Company | Production of synthesis gas |
US4474230A (en) * | 1982-08-31 | 1984-10-02 | Foster Wheeler Energy Corporation | Fluidized bed reactor system |
EP0335668A2 (en) * | 1988-03-28 | 1989-10-04 | Exxon Research And Engineering Company | Method and catalyst for synthesis gas preparation |
Non-Patent Citations (2)
Title |
---|
CHEMICAL ABSTRACTS, vol. 88, no. 26, 26 June 1978, Columbus, Ohio, US; abstract no. 193759, ANOKHIN, V. N. ET AL: "Catalysts and kinetics of the conversion of methane with water vapor" XP002062323 * |
NAUCHN. OSN. KATAL. KONVERSII UGLEVODORODOV (1977), 63-83. EDITOR(S): VESELOV, V. V. PUBLISHER: "NAUKOVA DUMKA", KIEV, USSR. CODEN: 37LJA4, 1977 * |
Also Published As
Publication number | Publication date |
---|---|
NO902050L (no) | 1990-11-27 |
AU5589790A (en) | 1990-11-22 |
NO902050D0 (no) | 1990-05-09 |
CA2014946C (en) | 1999-10-05 |
CA2014946A1 (en) | 1990-11-26 |
AU619983B2 (en) | 1992-02-06 |
US4888131A (en) | 1989-12-19 |
MY106754A (en) | 1995-07-31 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
BA | A request for search or an international-type search has been filed | ||
BB | A search report has been drawn up | ||
BC | A request for examination has been filed | ||
BN | A decision not to publish the application has become irrevocable |