JP5427791B2 - ペンタフルオロプロペンの水素化方法 - Google Patents
ペンタフルオロプロペンの水素化方法 Download PDFInfo
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- JP5427791B2 JP5427791B2 JP2010543573A JP2010543573A JP5427791B2 JP 5427791 B2 JP5427791 B2 JP 5427791B2 JP 2010543573 A JP2010543573 A JP 2010543573A JP 2010543573 A JP2010543573 A JP 2010543573A JP 5427791 B2 JP5427791 B2 JP 5427791B2
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- Japan
- Prior art keywords
- catalyst
- pentafluoropropene
- weight
- palladium
- hydrogenating
- 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.)
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- 238000000034 method Methods 0.000 title claims description 14
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 title description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 claims description 5
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 claims description 5
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical compound FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 claims description 3
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000005796 dehydrofluorination reaction Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical class CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 2
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- CDOOAUSHHFGWSA-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropene Chemical compound FC=CC(F)(F)F CDOOAUSHHFGWSA-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Sutcliffe-Speakman SS207C炭素上3%パラジウムを、炭素単体に水性塩化パラジウム(II)を含浸させることにより、調製した。塩化パラジウム(II)を水に溶解させるために、媒体を塩酸で、全ての塩が溶解するまで、酸性化する必要があった。次いで、触媒を乾燥させた。Sutcliffe-Speakman SS207C炭素上3%パラジウム2 gを、Inconel反応器チューブの中に装填した。この反応器チューブを窒素(60 ml/分)で掃気し、触媒を250℃でさらに乾燥させた。次いで、水素(16 ml/分)を窒素気流に加え、窒素気流を停止した。この処理を4時間続行した。次いで、R-1225yeZ(>98%)及び水素の混合物を触媒の上に様々な流量及び温度で通した。反応器から出るガスの試料を採取し、それらの組成を測定した。
例2を、例1と全く同様に行ったが、触媒は、0.5%Pd/C0.5 gをSS207C炭素9.5 gで希釈した混合物で置き換えた。
例1
結果を表1にまとめて示す。反応器に外部の熱を全く供給する必要無しに、高原料転化を達成した。反応器から出るガス中にR-245ebを検出したが、主生成物は、質量分光測定を使用してテトラフルオロプロパン、C3H4F4、R-254eb、CF3CHFCH3と同定された化学種であった。これは、R-245ebの還元性脱フッ化水素反応の生成物であろう。
希釈した低Pd触媒を使用することにより、反応を実際にR-245eb段階で実質的に停止し、それによって、R-245ebを選択的に製造できることを立証できた、表2参照。
Claims (3)
- 1,1,1,2−テトラフルオロプロパン(R−254eb)、1,1,1,2,3−ペンタフルオロプロパン(R−245eb)、3,3,3,2−テトラフルオロプロペン(R−1234yf)及び1,1,1−トリフルオロプロペン(R−1243zf)の少なくとも2つのブレンドを製造する方法であって、前記ブレンドが未反応の3,3,3,2,1−ペンタフルオロプロペン(R−1225ye)をも含んでおり、該方法が3,3,3,2,1−ペンタフルオロプロペン(R−1225ye)を水素化することを含んでなり、該水素化が、Pd/C触媒であって、該触媒におけるパラジウム金属装填量が該触媒の0.01〜0.025重量%である触媒の存在下、75〜125℃で行われる、方法。
- 前記製造されるブレンドが、少なくとも7重量%の1,1,1,2,3−ペンタフルオロプロパン(R−245eb)を含んでなる、請求項1に記載の方法。
- 前記水素化反応が100℃以下で行われる、請求項1又は2に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0801209.8 | 2008-01-23 | ||
GBGB0801209.8A GB0801209D0 (en) | 2008-01-23 | 2008-01-23 | Process |
PCT/GB2009/000206 WO2009093047A2 (en) | 2008-01-23 | 2009-01-23 | Process for the hydrogenation of pentafluoropropene |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011510057A JP2011510057A (ja) | 2011-03-31 |
JP5427791B2 true JP5427791B2 (ja) | 2014-02-26 |
Family
ID=39166219
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010543573A Active JP5427791B2 (ja) | 2008-01-23 | 2009-01-23 | ペンタフルオロプロペンの水素化方法 |
Country Status (12)
Country | Link |
---|---|
US (1) | US8471078B2 (ja) |
EP (1) | EP2238097A2 (ja) |
JP (1) | JP5427791B2 (ja) |
KR (1) | KR101206877B1 (ja) |
CN (1) | CN101925562B (ja) |
AU (1) | AU2009207419A1 (ja) |
BR (1) | BRPI0907431A2 (ja) |
CA (1) | CA2713392C (ja) |
GB (1) | GB0801209D0 (ja) |
MX (1) | MX2010008093A (ja) |
WO (1) | WO2009093047A2 (ja) |
ZA (1) | ZA201005576B (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8766020B2 (en) | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
GB0808836D0 (en) | 2008-05-15 | 2008-06-18 | Ineos Fluor Ltd | Process |
US8486293B2 (en) * | 2009-10-30 | 2013-07-16 | E I Du Pont De Nemours And Company | Hydrogen fluoride-HFC-254eb azeotrope and its uses |
US8513474B2 (en) | 2010-06-24 | 2013-08-20 | Honeywell International Inc. | Process for the manufacture of fluorinated olefins |
EP2671860B2 (en) | 2011-02-04 | 2024-05-29 | AGC Inc. | Method for purifying 2,3,3,3-tetrafluoropropene |
TW201247315A (en) | 2011-05-16 | 2012-12-01 | Du Pont | Catalytic hydrogenation of fluoroolefins, alpha-alumina supported palladium compositions and their use as hydrogenation catalysts |
US9290424B2 (en) * | 2013-03-14 | 2016-03-22 | Honeywell International Inc. | Processes for the hydrogenation of halogenated alkenes and the manufacture of fluorinated olefins |
KR101492871B1 (ko) * | 2013-08-07 | 2015-02-13 | 한국과학기술연구원 | 이온성 액체를 이용하여 제조된 탄소에 담지된 팔라듐 촉매 및 이것의 제조방법과, 이를 이용한 수소불화탄소의 수소화 반응 |
GB201410174D0 (en) * | 2014-06-09 | 2014-07-23 | Mexichem Amanco Holding Sa | Process |
CN104945221B (zh) * | 2015-06-11 | 2017-07-18 | 浙江衢州巨新氟化工有限公司 | 一种联产2,3,3,3‑四氟丙烯和1,3,3,3‑四氟丙烯的方法 |
EP4212500A1 (en) | 2018-06-06 | 2023-07-19 | Honeywell International Inc. | Method for dehydrochlorination of hcfc-244bb to manufacture hfo-1234yf |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2550953A (en) * | 1944-12-08 | 1951-05-01 | Du Pont | Catalytic hydrogenation of unsaturated fluorohydrocarbons |
US5162594A (en) * | 1990-10-11 | 1992-11-10 | E. I. Du Pont De Nemours And Company | Process for production of polyfluoroolefins |
AU664753B2 (en) * | 1992-06-05 | 1995-11-30 | Daikin Industries, Ltd. | Processes for producing 1,1,1,2,3-pentafluoropropene and producing -pentafluoropropane |
JPH067281A (ja) | 1992-06-29 | 1994-01-18 | Hoshizaki Electric Co Ltd | 食器洗浄機のための電気制御装置 |
US5396000A (en) | 1993-05-24 | 1995-03-07 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,2,3,-pentafluoropropane |
JP3407379B2 (ja) | 1993-06-10 | 2003-05-19 | ダイキン工業株式会社 | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
US5780695A (en) * | 1994-12-02 | 1998-07-14 | Uop | Process for the selective saturation of olefin-containing halogenated organic streams |
JP3543863B2 (ja) | 1994-12-16 | 2004-07-21 | ダイキン工業株式会社 | 1,1,1,2,3,3−ヘキサフルオロプロパンの製造方法 |
JPH0967281A (ja) * | 1995-09-01 | 1997-03-11 | Daikin Ind Ltd | 1,1,1,3,3−ペンタフルオロプロペンの製造方法及び1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
US5945573A (en) | 1997-01-31 | 1999-08-31 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,1,1,3,3-pentafluoropropane |
US6313359B1 (en) * | 2000-07-17 | 2001-11-06 | Honeywell International Inc. | Method of making hydrofluorocarbons |
US7185352B2 (en) * | 2001-05-11 | 2007-02-27 | Intel Corporation | Method and apparatus for combining broadcast schedules and content on a digital broadcast-enabled client platform |
US7560602B2 (en) | 2005-11-03 | 2009-07-14 | Honeywell International Inc. | Process for manufacture of fluorinated olefins |
EP2066605B1 (en) | 2006-09-05 | 2013-12-25 | E.I. Du Pont De Nemours And Company | Process to manufacture 2,3,3,3-tetrafluoropropene |
-
2008
- 2008-01-23 GB GBGB0801209.8A patent/GB0801209D0/en not_active Ceased
-
2009
- 2009-01-23 AU AU2009207419A patent/AU2009207419A1/en not_active Abandoned
- 2009-01-23 JP JP2010543573A patent/JP5427791B2/ja active Active
- 2009-01-23 CN CN200980102968.2A patent/CN101925562B/zh active Active
- 2009-01-23 EP EP09704318A patent/EP2238097A2/en not_active Withdrawn
- 2009-01-23 MX MX2010008093A patent/MX2010008093A/es active IP Right Grant
- 2009-01-23 KR KR1020107016463A patent/KR101206877B1/ko not_active IP Right Cessation
- 2009-01-23 BR BRPI0907431-7A patent/BRPI0907431A2/pt not_active Application Discontinuation
- 2009-01-23 CA CA2713392A patent/CA2713392C/en not_active Expired - Fee Related
- 2009-01-23 US US12/735,496 patent/US8471078B2/en active Active
- 2009-01-23 WO PCT/GB2009/000206 patent/WO2009093047A2/en active Application Filing
-
2010
- 2010-08-04 ZA ZA2010/05576A patent/ZA201005576B/en unknown
Also Published As
Publication number | Publication date |
---|---|
CA2713392A1 (en) | 2009-07-30 |
KR101206877B1 (ko) | 2012-11-30 |
KR20100126279A (ko) | 2010-12-01 |
AU2009207419A1 (en) | 2009-07-30 |
JP2011510057A (ja) | 2011-03-31 |
US20110152586A1 (en) | 2011-06-23 |
CN101925562B (zh) | 2014-03-12 |
WO2009093047A3 (en) | 2009-09-11 |
GB0801209D0 (en) | 2008-02-27 |
MX2010008093A (es) | 2010-09-09 |
US8471078B2 (en) | 2013-06-25 |
BRPI0907431A2 (pt) | 2015-07-14 |
EP2238097A2 (en) | 2010-10-13 |
WO2009093047A2 (en) | 2009-07-30 |
CA2713392C (en) | 2013-01-22 |
CN101925562A (zh) | 2010-12-22 |
ZA201005576B (en) | 2014-01-29 |
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