JP5380051B2 - 1,3−ジアルキル−2−イミダゾリジノン類の製造方法 - Google Patents
1,3−ジアルキル−2−イミダゾリジノン類の製造方法 Download PDFInfo
- Publication number
- JP5380051B2 JP5380051B2 JP2008292275A JP2008292275A JP5380051B2 JP 5380051 B2 JP5380051 B2 JP 5380051B2 JP 2008292275 A JP2008292275 A JP 2008292275A JP 2008292275 A JP2008292275 A JP 2008292275A JP 5380051 B2 JP5380051 B2 JP 5380051B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- catalyst
- silica
- dialkyl
- imidazolidinone
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 75
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 239000000377 silicon dioxide Substances 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 31
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 22
- 239000001569 carbon dioxide Substances 0.000 claims description 11
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 16
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- -1 SBA-15 Chemical compound 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 238000010813 internal standard method Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FXCPLDHPNOXGOM-UHFFFAOYSA-N 1,3-dibutylimidazolidin-2-one Chemical compound CCCCN1CCN(CCCC)C1=O FXCPLDHPNOXGOM-UHFFFAOYSA-N 0.000 description 1
- NYCCIHSMVNRABA-UHFFFAOYSA-N 1,3-diethylimidazolidin-2-one Chemical compound CCN1CCN(CC)C1=O NYCCIHSMVNRABA-UHFFFAOYSA-N 0.000 description 1
- NFJSYLMJBNUDNG-UHFFFAOYSA-N 1,3-dipropylimidazolidin-2-one Chemical compound CCCN1CCN(CCC)C1=O NFJSYLMJBNUDNG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- MFIGJRRHGZYPDD-UHFFFAOYSA-N n,n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)NCCNC(C)C MFIGJRRHGZYPDD-UHFFFAOYSA-N 0.000 description 1
- YRGVKPIUZUOJSJ-UHFFFAOYSA-N n,n'-dibutylethane-1,2-diamine Chemical compound CCCCNCCNCCCC YRGVKPIUZUOJSJ-UHFFFAOYSA-N 0.000 description 1
- VATUKUMHBXZSCD-UHFFFAOYSA-N n,n'-dipropylethane-1,2-diamine Chemical compound CCCNCCNCCC VATUKUMHBXZSCD-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- SYQIIBRVOSBWME-UHFFFAOYSA-N trichloromethyl formate Chemical compound ClC(Cl)(Cl)OC=O SYQIIBRVOSBWME-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
メソポーラスシリカ(MCM−41型、カタログ番号643645、アルドリッチ社製)を、錠剤成型器で圧縮成型した後、粉砕し、500μm以上850μm以下の粒子径にメッシュ揃えした後、500℃、2時間空気中で焼成し、メソポーラスシリカからなる成型触媒を得た。
・「ガスクロマトグラフ」:島津製作所製、製品名Shimadzu GC-17A
・「カラム」:J&W Scientific製、製品名DB−1(内径0.25mm、膜圧0.25μm、長さ30M)
・「キャリアガス」:Heガス(1ml/分)
・「カラム温度」:50℃で5分保持した後、15℃/分の速度で250℃まで昇温し、250℃で12分保持した。
・「内部標準法」:採取した反応液に、内部標準物質としてメシチレンを加え、内部標準法で定量した。
反応温度を200℃に変更したこと以外は、実施例1と同様にして反応を行った。その結果、N,N'−ジメチルエチレンジアミンの転化率は92%であり、1,3−ジメチル−2−イミダゾリジノンの選択率は100%であった。
反応圧力を6MPaに変更したこと以外は、実施例2と同様にして反応を行った。その結果、N,N'−ジメチルエチレンジアミンの転化率は90%であり、1,3−ジメチル−2−イミダゾリジノンの選択率は100%であった。
シリカ触媒として、アモルファスシリカ(製品名CARiACT Q-30、富士シリシア化学社製)を用いたこと以外は、実施例2と同様にして反応を行った。その結果、N,N'−ジメチルエチレンジアミンの転化率は41%であり、1,3−ジメチル−2−イミダゾリジノンの選択率は100%であった。
シリカ触媒として、アモルファスシリカ(製品名CARiACT Q-30、富士シリシア化学社製)を用いたこと以外は、実施例3と同様にして反応を行った。その結果、N,N'−ジメチルエチレンジアミンの転化率は31%であり、1,3−ジメチル−2−イミダゾリジノンの選択率は100%であった。
シリカ触媒として、ワームホール構造を有するメソポーラスシリカであるHMS(アルドリッチ社製)を用いたこと以外は、実施例3と同様にして反応を行った。その結果、N,N'−ジメチルエチレンジアミンの転化率は80%であり、1,3−ジメチル−2−イミダゾリジノンの選択率は100%であった。
シリカ触媒として、シリカアルミナ(製品名JRC-SAL-2; 13.8wt% Al2O3 触媒学会)を用いたこと以外は、実施例2と同様にして反応を行った。その結果、N,N'−ジメチルエチレンジアミンの転化率は37%であり、1,3−ジメチル−2−イミダゾリジノンの選択率は100%であった。
シリカ触媒の代わりに、γ−アルミナ(製品名JRC-ALO-6, 触媒学会)を触媒として用いたこと以外は、実施例2と同様にして反応を行った。その結果、N,N'−ジメチルエチレンジアミンはほとんど転化しなかった。
反応圧力を0.1MPaに変更したこと以外は、実施例2と同様の条件で反応を行った。その結果、N,N'−ジメチルエチレンジアミンはほとんど転化しなかった。
Claims (3)
- 反応圧力が、0.2MPa〜30MPaの範囲内である請求項1記載の1,3−ジアルキル−2−イミダゾリジノン類の製造方法。
- 一般式(1)及び(2)中のR1及びR2が、メチル基である請求項1又は2記載の1,3−ジアルキル−2−イミダゾリジノン類の製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008292275A JP5380051B2 (ja) | 2008-11-14 | 2008-11-14 | 1,3−ジアルキル−2−イミダゾリジノン類の製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008292275A JP5380051B2 (ja) | 2008-11-14 | 2008-11-14 | 1,3−ジアルキル−2−イミダゾリジノン類の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010116372A JP2010116372A (ja) | 2010-05-27 |
JP5380051B2 true JP5380051B2 (ja) | 2014-01-08 |
Family
ID=42304256
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008292275A Active JP5380051B2 (ja) | 2008-11-14 | 2008-11-14 | 1,3−ジアルキル−2−イミダゾリジノン類の製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5380051B2 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109847806A (zh) * | 2019-01-07 | 2019-06-07 | 厦门大学 | 一种聚离子液体-铈氧化合物催化剂及其制备方法和应用 |
JP7474938B2 (ja) | 2020-07-28 | 2024-04-26 | 中国電力株式会社 | カットアウト接続器具 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB201216921D0 (en) * | 2012-09-21 | 2012-11-07 | Worn Again Footwear And Accessories Ltd | Process |
JP7523058B2 (ja) | 2020-05-28 | 2024-07-26 | 東ソー株式会社 | 環状ウレア化合物の製造方法 |
WO2024069973A1 (ja) * | 2022-09-30 | 2024-04-04 | 国立大学法人東北大学 | 二酸化炭素の供給転換剤および二酸化炭素の利用方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57175170A (en) * | 1981-04-22 | 1982-10-28 | Kawaken Fine Chem Co Ltd | Preparation of 1,3-dimethyl-2-imidazolidinone |
DE3744120A1 (de) * | 1987-12-24 | 1989-07-06 | Basf Ag | Verfahren zur herstellung von 1,3-dialkyl-2-imidazolidinonen |
JPH10195055A (ja) * | 1997-01-16 | 1998-07-28 | Mitsui Chem Inc | ジメチルイミダゾリジノンの製造法 |
JP2000026427A (ja) * | 1998-07-08 | 2000-01-25 | Mitsui Chemicals Inc | 1,3−ジアルキル−2−イミダゾリジノンの製造方法 |
-
2008
- 2008-11-14 JP JP2008292275A patent/JP5380051B2/ja active Active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109847806A (zh) * | 2019-01-07 | 2019-06-07 | 厦门大学 | 一种聚离子液体-铈氧化合物催化剂及其制备方法和应用 |
JP7474938B2 (ja) | 2020-07-28 | 2024-04-26 | 中国電力株式会社 | カットアウト接続器具 |
Also Published As
Publication number | Publication date |
---|---|
JP2010116372A (ja) | 2010-05-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5380051B2 (ja) | 1,3−ジアルキル−2−イミダゾリジノン類の製造方法 | |
JP5640093B2 (ja) | ビス(アミノメチル)シクロヘキサン類の製造方法 | |
JP5448987B2 (ja) | トランス−1,4−ビス(アミノメチル)シクロヘキサンの製造方法 | |
JP6217653B2 (ja) | α,α−ジフルオロアセトアルデヒドの製造方法 | |
TWI476047B (zh) | Preparation of pyruvate | |
JP5562429B2 (ja) | トランス−1,4−ビス(アミノメチル)シクロヘキサンの製造方法 | |
JP2008074754A (ja) | トランス−1,4−ジアミノシクロヘキサンの製造方法 | |
KR101294526B1 (ko) | 고순도 n-에틸메틸아민 및 이의 제조 방법 | |
JP6562097B2 (ja) | α−フルオロアクリル酸エステル類の製造方法 | |
JP6680322B2 (ja) | α−フルオロアクリル酸エステル類の製造方法 | |
ES2914774T3 (es) | Método para producir indancarbaldehído | |
JP5646274B2 (ja) | キシリレンジアミン類の製造方法 | |
JP2009107969A (ja) | 塩化ビニルの製造方法 | |
KR101659163B1 (ko) | 알칸올의 제조방법 | |
JPWO2013168827A1 (ja) | オキシラン化合物からのグリコール類の製造方法 | |
WO2017033955A1 (ja) | ハロゲン化アクリル酸エステル誘導体の製造方法 | |
TW201223929A (en) | Hydride transfer process for ketone preparation | |
US20170217862A1 (en) | Method for producing cyclopentyl alkyl ether compound | |
JP5564088B2 (ja) | トランス−1,4−ジアミノシクロヘキサンの製造方法 | |
Lu et al. | Asymmetric Michael addition of ketones to nitroolefins catalyzed by a novel chiral pyrrolidine-thiourea in the ionic liquid | |
JP2004525073A5 (ja) | ||
JP2004525073A (ja) | オレフィンオキシドの連続製造方法 | |
JPH01301631A (ja) | 1,1,1,3,3,3−ヘキサフルオロプロパン−2−オールの製造法 | |
WO2014013706A1 (ja) | 2-(イソプロピルアミノ)エタノールの製造方法 | |
JP4923698B2 (ja) | 4−アミノテトラヒドロピラン化合物の製法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110802 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20110802 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130625 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130627 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130821 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130910 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130930 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5380051 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |