DE2552987C2 - Verfahren zur kontinuierlichen Herstellung ätherfreier Acrylsäurealkylester - Google Patents
Verfahren zur kontinuierlichen Herstellung ätherfreier AcrylsäurealkylesterInfo
- Publication number
- DE2552987C2 DE2552987C2 DE2552987A DE2552987A DE2552987C2 DE 2552987 C2 DE2552987 C2 DE 2552987C2 DE 2552987 A DE2552987 A DE 2552987A DE 2552987 A DE2552987 A DE 2552987A DE 2552987 C2 DE2552987 C2 DE 2552987C2
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- distillation
- zone
- reaction
- weight
- 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
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 16
- 238000010924 continuous production Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 40
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 34
- 238000004821 distillation Methods 0.000 claims description 31
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 30
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 239000012074 organic phase Substances 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000008346 aqueous phase Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 22
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000012429 reaction media Substances 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2552987A DE2552987C2 (de) | 1975-11-26 | 1975-11-26 | Verfahren zur kontinuierlichen Herstellung ätherfreier Acrylsäurealkylester |
| GB48108/76A GB1515620A (en) | 1975-11-26 | 1976-11-18 | Continuous production of alkyl acrylates free from ether |
| CA266,125A CA1083601A (en) | 1975-11-26 | 1976-11-19 | Continuous production of alkyl acrylates free from ether. |
| NL7613045A NL7613045A (nl) | 1975-11-26 | 1976-11-23 | Werkwijze voor de continue bereiding van ether- vrije acrylzuuralkylesters. |
| BE172693A BE848739A (fr) | 1975-11-26 | 1976-11-25 | Procede de preparation en continu d'acrylates d'alkyle exempts d'ether, |
| JP51142111A JPS5265217A (en) | 1975-11-26 | 1976-11-26 | Continuous prodution of ether free acrylic acid ester |
| FR7635771A FR2336372A1 (fr) | 1975-11-26 | 1976-11-26 | Procede de preparation en continu d'acrylates d'alkyle exempts d'ether |
| US06/066,511 US4280010A (en) | 1975-11-26 | 1979-08-14 | Continuous production of alkyl acrylates free from ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2552987A DE2552987C2 (de) | 1975-11-26 | 1975-11-26 | Verfahren zur kontinuierlichen Herstellung ätherfreier Acrylsäurealkylester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2552987A1 DE2552987A1 (de) | 1977-06-02 |
| DE2552987C2 true DE2552987C2 (de) | 1983-09-29 |
Family
ID=5962639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2552987A Expired DE2552987C2 (de) | 1975-11-26 | 1975-11-26 | Verfahren zur kontinuierlichen Herstellung ätherfreier Acrylsäurealkylester |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4280010A (show.php) |
| JP (1) | JPS5265217A (show.php) |
| BE (1) | BE848739A (show.php) |
| CA (1) | CA1083601A (show.php) |
| DE (1) | DE2552987C2 (show.php) |
| FR (1) | FR2336372A1 (show.php) |
| GB (1) | GB1515620A (show.php) |
| NL (1) | NL7613045A (show.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0795535A1 (de) | 1996-02-06 | 1997-09-17 | Basf Aktiengesellschaft | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern der (Meth) acrylsäure |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4434421A (en) * | 1981-11-18 | 1984-02-28 | General Electric Company | Method for digital data transmission with bit-echoed arbitration |
| US4458088A (en) * | 1982-04-01 | 1984-07-03 | The Standard Oil Company (Sohio) | Continuous process for the extraction and esterification of carboxylic acid |
| US4698440A (en) * | 1983-09-14 | 1987-10-06 | E. I. Du Pont De Nemours And Company | Process for making n-butyl methacrylate |
| DE3728242A1 (de) * | 1987-08-25 | 1989-03-09 | Basf Ag | Verfahren zur herstellung von carbonsaeureestern |
| DE3843854A1 (de) * | 1988-12-24 | 1990-06-28 | Henkel Kgaa | Verfahren zur verbesserten herstellung von (meth)acrylsaeureestern mehrwertiger alkohole (i) |
| US4999452A (en) * | 1989-05-15 | 1991-03-12 | Union Carbide Chemicals And Plastics Company Inc. | Process for producing acrylic ester |
| DE19510891A1 (de) * | 1995-03-24 | 1996-09-26 | Basf Ag | Verfahren zur kontinuierlicheen Herstellung von Alkylestern der (Meth)acrylsäure |
| DE19536178A1 (de) * | 1995-09-28 | 1997-04-03 | Basf Ag | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| SG81213A1 (en) * | 1995-12-15 | 2001-06-19 | Rohm & Haas | Process for producing butyle acrylate |
| DE19604253A1 (de) * | 1996-02-06 | 1997-08-07 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| DE19604267A1 (de) * | 1996-02-06 | 1997-08-07 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| US6605738B1 (en) | 1996-05-29 | 2003-08-12 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for refining butyl acrylate |
| DE19648746A1 (de) * | 1996-11-25 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE19648743A1 (de) * | 1996-11-25 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE19648745A1 (de) * | 1996-11-25 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| US5877345A (en) * | 1997-02-07 | 1999-03-02 | Rohm And Haas Company | Process for producing butyl acrylate |
| DE69717314T2 (de) * | 1997-05-20 | 2003-08-21 | Union Carbide Chemicals & Plastics Technology Corp., Danbury | Verfahren zur raffination von butylacrylat |
| US6482976B1 (en) * | 1999-06-17 | 2002-11-19 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| US6172258B1 (en) | 1999-09-14 | 2001-01-09 | Celanese International Corporation | Process for the production and purification of n-butyl acrylate |
| US6180820B1 (en) * | 1999-09-14 | 2001-01-30 | Celanese International Corporation | Process for the production and purification of N-butyl acrylate |
| DE10007213A1 (de) * | 2000-02-17 | 2001-08-23 | Basf Ag | Verfahren zur Herstellung von Estern alpha,beta-ungesättigter Carbonsäuren |
| EP1345886A1 (de) * | 2000-12-18 | 2003-09-24 | Basf Aktiengesellschaft | Verfahren zur herstellung von höheren (meth)acrylsäureestern |
| DE10127941A1 (de) * | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10144490A1 (de) * | 2001-09-10 | 2003-03-27 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE10156116A1 (de) * | 2001-11-15 | 2003-06-26 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern mehrwertiger Alkohole |
| DE102005010588A1 (de) * | 2005-03-08 | 2006-05-24 | Basf Ag | Verfahren zur Herstellung von Alkylestern der (Meth)acrylsäure |
| DE102005010587A1 (de) * | 2005-03-08 | 2006-06-08 | Basf Ag | Verfahren zur Herstellung von Alkylestern der (Meth)acrylsäure |
| US7921388B2 (en) * | 2006-09-18 | 2011-04-05 | International Business Machines Corporation | Wordline booster design structure and method of operating a wordine booster circuit |
| US8765217B2 (en) | 2008-11-04 | 2014-07-01 | Entrotech, Inc. | Method for continuous production of (meth)acrylate syrup and adhesives therefrom |
| US20100113692A1 (en) * | 2008-11-04 | 2010-05-06 | Mcguire Jr James E | Apparatus for Continuous Production of Partially Polymerized Compositions |
| DE102008060218A1 (de) | 2008-12-04 | 2010-06-10 | Evonik Stockhausen Gmbh | Aufarbeitungsverfahren bei der Herstellung von (Meth)Acrylsäurealkylestern |
| US8329079B2 (en) | 2009-04-20 | 2012-12-11 | Entrochem, Inc. | Method and apparatus for continuous production of partially polymerized compositions and polymers therefrom |
| CN103221379B (zh) | 2010-11-22 | 2015-04-15 | 罗门哈斯公司 | 丙烯酸酯生产方法 |
| DE102010062601A1 (de) | 2010-12-08 | 2012-06-14 | Evonik Stockhausen Gmbh | Verfahren zur Herstellung von (Meth)Acrylsäureestern |
| CN102249913B (zh) * | 2011-05-17 | 2013-11-06 | 上海华谊丙烯酸有限公司 | 一种制备丙烯酸丁酯的方法 |
| JP7222977B2 (ja) * | 2017-08-17 | 2023-02-15 | ビーエーエスエフ ソシエタス・ヨーロピア | アクリル酸－ｎ－ブチルエステルまたはアクリル酸イソブチルエステルの連続的製造方法 |
| US12098124B2 (en) | 2019-04-16 | 2024-09-24 | Rohm And Haas Company | Acid catalyzed synthesis of methyl acrylate from acrylic acid and methanol |
| SG11202110453WA (en) | 2019-04-16 | 2021-11-29 | Rohm & Haas | Acid catalyzed synthesis of methyl acrylate from acrylic acid and methanol |
| CN116848083A (zh) * | 2020-12-11 | 2023-10-03 | 巴斯夫欧洲公司 | 通过使用至少一个由传感器（s）闭环控制的控制单元使醇与（甲基）丙烯酸反应来连续制备（甲基）丙烯酸酯的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1468932B2 (de) * | 1965-09-23 | 1976-01-22 | Röhm GmbH, 6100 Darmstadt | Verfahren zur kontinuierlichen herstellung von niedermolekularen aliphatischen acrylsaeureestern |
| DE2226829A1 (de) * | 1972-06-02 | 1973-12-20 | Knapsack Ag | Verfahren zur herstellung von acrylsaeureestern |
| US3776947A (en) * | 1972-10-10 | 1973-12-04 | Nippon Catalytic Chem Ind | Continuous esterification process |
| DE2449811C2 (de) * | 1974-10-19 | 1983-01-05 | Hoechst Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Herstellung von dibutylätherfreiem n-Butylacrylat |
-
1975
- 1975-11-26 DE DE2552987A patent/DE2552987C2/de not_active Expired
-
1976
- 1976-11-18 GB GB48108/76A patent/GB1515620A/en not_active Expired
- 1976-11-19 CA CA266,125A patent/CA1083601A/en not_active Expired
- 1976-11-23 NL NL7613045A patent/NL7613045A/xx not_active Application Discontinuation
- 1976-11-25 BE BE172693A patent/BE848739A/xx not_active IP Right Cessation
- 1976-11-26 FR FR7635771A patent/FR2336372A1/fr active Granted
- 1976-11-26 JP JP51142111A patent/JPS5265217A/ja active Pending
-
1979
- 1979-08-14 US US06/066,511 patent/US4280010A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0795535A1 (de) | 1996-02-06 | 1997-09-17 | Basf Aktiengesellschaft | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern der (Meth) acrylsäure |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2336372A1 (fr) | 1977-07-22 |
| US4280010A (en) | 1981-07-21 |
| FR2336372B1 (show.php) | 1983-01-07 |
| JPS5265217A (en) | 1977-05-30 |
| CA1083601A (en) | 1980-08-12 |
| DE2552987A1 (de) | 1977-06-02 |
| GB1515620A (en) | 1978-06-28 |
| BE848739A (fr) | 1977-05-25 |
| NL7613045A (nl) | 1977-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |