JPH0519536B2 - - Google Patents
Info
- Publication number
- JPH0519536B2 JPH0519536B2 JP59270319A JP27031984A JPH0519536B2 JP H0519536 B2 JPH0519536 B2 JP H0519536B2 JP 59270319 A JP59270319 A JP 59270319A JP 27031984 A JP27031984 A JP 27031984A JP H0519536 B2 JPH0519536 B2 JP H0519536B2
- Authority
- JP
- Japan
- Prior art keywords
- deuterated
- methyl methacrylate
- parts
- reaction
- methyl acrylate
- 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 - Lifetime
Links
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical class CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N deuterated acetone Substances [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- NTQWADDNQQUGRH-UHFFFAOYSA-N hydrogen sulfate;2-methylprop-2-enoylazanium Chemical compound OS(O)(=O)=O.CC(=C)C(N)=O NTQWADDNQQUGRH-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59270319A JPS61148141A (ja) | 1984-12-21 | 1984-12-21 | 重水素化アクリル酸メチルまたは重水素化メタクリル酸メチルの製造法 |
| CA000497590A CA1264330A (en) | 1984-12-21 | 1985-12-13 | Process for the production of deuterated methyl acrylate or deuterated methyl methacrylate |
| DE8585116130T DE3582870D1 (de) | 1984-12-21 | 1985-12-18 | Verfahren zur herstellung von deuteriertem methylacrylat oder methylmethacrylat. |
| EP85116130A EP0186106B1 (en) | 1984-12-21 | 1985-12-18 | Process for the production of deuterated methyl acrylate or deuterated methyl methacrylate |
| NO855201A NO162662C (no) | 1984-12-21 | 1985-12-20 | Fremgangsmaate ved fremstilling av deutrert metylakrylat eller metylmetakrylat. |
| US07/154,485 US4874890A (en) | 1984-12-21 | 1988-02-08 | Process for the production of deuterated methyl acrylate or deuterated methyl methacrylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59270319A JPS61148141A (ja) | 1984-12-21 | 1984-12-21 | 重水素化アクリル酸メチルまたは重水素化メタクリル酸メチルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61148141A JPS61148141A (ja) | 1986-07-05 |
| JPH0519536B2 true JPH0519536B2 (Direct) | 1993-03-17 |
Family
ID=17484607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59270319A Granted JPS61148141A (ja) | 1984-12-21 | 1984-12-21 | 重水素化アクリル酸メチルまたは重水素化メタクリル酸メチルの製造法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4874890A (Direct) |
| EP (1) | EP0186106B1 (Direct) |
| JP (1) | JPS61148141A (Direct) |
| CA (1) | CA1264330A (Direct) |
| DE (1) | DE3582870D1 (Direct) |
| NO (1) | NO162662C (Direct) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011136369A1 (ja) | 2010-04-28 | 2011-11-03 | 協和発酵キリン株式会社 | カチオン性脂質 |
| WO2011136368A1 (ja) | 2010-04-28 | 2011-11-03 | 協和発酵キリン株式会社 | カチオン性脂質 |
| WO2013018899A1 (ja) | 2011-08-03 | 2013-02-07 | 協和発酵キリン株式会社 | ジベンゾオキセピン誘導体 |
| WO2013031931A1 (ja) | 2011-09-02 | 2013-03-07 | 協和発酵キリン株式会社 | ケモカイン受容体活性調節剤 |
| WO2013065825A1 (ja) | 2011-11-02 | 2013-05-10 | 協和発酵キリン株式会社 | カチオン性脂質 |
| WO2013089151A1 (ja) | 2011-12-12 | 2013-06-20 | 協和発酵キリン株式会社 | カチオン性脂質を含有するドラッグデリバリーシステムのための脂質ナノ粒子 |
| WO2013089152A1 (ja) | 2011-12-12 | 2013-06-20 | 協和発酵キリン株式会社 | カチオン性脂質の組み合わせを含有する脂質ナノ粒子 |
| WO2014002967A1 (ja) | 2012-06-25 | 2014-01-03 | 協和発酵キリン株式会社 | 4,6-ヘキサデカジエン-2,4-ジカルボン酸誘導体 |
| WO2014084330A1 (ja) | 2012-11-30 | 2014-06-05 | 協和発酵キリン株式会社 | 含窒素複素環化合物 |
| WO2014088085A1 (ja) | 2012-12-06 | 2014-06-12 | 協和発酵キリン株式会社 | ピリドン化合物 |
| WO2017111076A1 (ja) | 2015-12-24 | 2017-06-29 | 協和発酵キリン株式会社 | α、β不飽和アミド化合物 |
| WO2018235926A1 (ja) | 2017-06-23 | 2018-12-27 | 協和発酵キリン株式会社 | α、β不飽和アミド化合物 |
| WO2019189778A1 (ja) | 2018-03-30 | 2019-10-03 | 協和発酵キリン株式会社 | 抗がん活性を有する化合物 |
| WO2021065980A1 (ja) | 2019-09-30 | 2021-04-08 | 協和キリン株式会社 | Ｂｅｔ分解剤 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3701302A1 (de) * | 1987-01-17 | 1988-07-28 | Hoechst Ag | Verfahren zur herstellung von deuterierten organischen verbindungen |
| US4914160A (en) * | 1988-06-23 | 1990-04-03 | Hormoz Azizian | Deuteration of unsaturated polymers and copolymers |
| CA2026042C (en) * | 1989-09-27 | 1996-02-27 | Saburo Imamura | Plate plastics optical waveguide |
| CA2148292A1 (en) * | 1994-05-05 | 1995-11-06 | Barrie W. Jackson | Liquid phase prparation of (meth)-acrylate from alpha-olefin |
| US6794522B2 (en) * | 2001-03-22 | 2004-09-21 | The Regents Of The University Of California | Process for preparing a deuterated or tritiated compound |
| TW200404054A (en) * | 2002-07-26 | 2004-03-16 | Wako Pure Chem Ind Ltd | Method for deuteration of aromatic ring |
| TW200413273A (en) * | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| TW200413274A (en) * | 2002-12-27 | 2004-08-01 | Wako Pure Chem Ind Ltd | Deuteration or tritiation method |
| JP4762898B2 (ja) * | 2003-07-24 | 2011-08-31 | 富士フイルム株式会社 | 重水素化（メタ）アクリル酸エステル、その製造法、その重合体、及び光学部材 |
| JP2007528859A (ja) * | 2003-07-24 | 2007-10-18 | 富士フイルム株式会社 | 重水素化（メタ）アクリル酸ノルボルニル、その製造法、その重合体、及び光学部材 |
| US20050114527A1 (en) * | 2003-10-08 | 2005-05-26 | Hankey Michael R. | System and method for personal communication over a global computer network |
| CN1906143A (zh) * | 2004-01-23 | 2007-01-31 | 和光纯药工业株式会社 | 使用混合催化剂的重氢化方法 |
| WO2006001236A1 (ja) * | 2004-06-25 | 2006-01-05 | Wako Pure Chemical Industries, Ltd. | ハロアクリル酸又はその塩の重水素化方法 |
| CN114560763B (zh) * | 2022-03-07 | 2024-02-20 | 山东汉峰新材料科技有限公司 | 一种氘代乙酸的生产工艺 |
-
1984
- 1984-12-21 JP JP59270319A patent/JPS61148141A/ja active Granted
-
1985
- 1985-12-13 CA CA000497590A patent/CA1264330A/en not_active Expired - Lifetime
- 1985-12-18 DE DE8585116130T patent/DE3582870D1/de not_active Expired - Lifetime
- 1985-12-18 EP EP85116130A patent/EP0186106B1/en not_active Expired - Lifetime
- 1985-12-20 NO NO855201A patent/NO162662C/no unknown
-
1988
- 1988-02-08 US US07/154,485 patent/US4874890A/en not_active Expired - Fee Related
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011136369A1 (ja) | 2010-04-28 | 2011-11-03 | 協和発酵キリン株式会社 | カチオン性脂質 |
| WO2011136368A1 (ja) | 2010-04-28 | 2011-11-03 | 協和発酵キリン株式会社 | カチオン性脂質 |
| WO2013018899A1 (ja) | 2011-08-03 | 2013-02-07 | 協和発酵キリン株式会社 | ジベンゾオキセピン誘導体 |
| WO2013031931A1 (ja) | 2011-09-02 | 2013-03-07 | 協和発酵キリン株式会社 | ケモカイン受容体活性調節剤 |
| WO2013065825A1 (ja) | 2011-11-02 | 2013-05-10 | 協和発酵キリン株式会社 | カチオン性脂質 |
| EP3301086A1 (en) | 2011-11-02 | 2018-04-04 | Kyowa Hakko Kirin Co., Ltd. | Production of a composition containing a complex between a membrane composed of a lipid monolayer and a nucleic acid, and, a lipid membrane for encapsulating the complex therein |
| WO2013089152A1 (ja) | 2011-12-12 | 2013-06-20 | 協和発酵キリン株式会社 | カチオン性脂質の組み合わせを含有する脂質ナノ粒子 |
| WO2013089151A1 (ja) | 2011-12-12 | 2013-06-20 | 協和発酵キリン株式会社 | カチオン性脂質を含有するドラッグデリバリーシステムのための脂質ナノ粒子 |
| WO2014002967A1 (ja) | 2012-06-25 | 2014-01-03 | 協和発酵キリン株式会社 | 4,6-ヘキサデカジエン-2,4-ジカルボン酸誘導体 |
| WO2014084330A1 (ja) | 2012-11-30 | 2014-06-05 | 協和発酵キリン株式会社 | 含窒素複素環化合物 |
| WO2014088085A1 (ja) | 2012-12-06 | 2014-06-12 | 協和発酵キリン株式会社 | ピリドン化合物 |
| WO2017111076A1 (ja) | 2015-12-24 | 2017-06-29 | 協和発酵キリン株式会社 | α、β不飽和アミド化合物 |
| WO2018235926A1 (ja) | 2017-06-23 | 2018-12-27 | 協和発酵キリン株式会社 | α、β不飽和アミド化合物 |
| WO2019189778A1 (ja) | 2018-03-30 | 2019-10-03 | 協和発酵キリン株式会社 | 抗がん活性を有する化合物 |
| WO2021065980A1 (ja) | 2019-09-30 | 2021-04-08 | 協和キリン株式会社 | Ｂｅｔ分解剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0186106B1 (en) | 1991-05-15 |
| EP0186106A3 (en) | 1988-01-27 |
| US4874890A (en) | 1989-10-17 |
| DE3582870D1 (de) | 1991-06-20 |
| NO162662C (no) | 1990-01-31 |
| EP0186106A2 (en) | 1986-07-02 |
| CA1264330A (en) | 1990-01-09 |
| JPS61148141A (ja) | 1986-07-05 |
| NO162662B (no) | 1989-10-23 |
| NO855201L (no) | 1986-06-23 |
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