JPS61148141A - 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 - Google Patents
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Info
- Publication number
- JPS61148141A JPS61148141A JP59270319A JP27031984A JPS61148141A JP S61148141 A JPS61148141 A JP S61148141A JP 59270319 A JP59270319 A JP 59270319A JP 27031984 A JP27031984 A JP 27031984A JP S61148141 A JPS61148141 A JP S61148141A
- Authority
- JP
- Japan
- Prior art keywords
- deuterated
- methyl methacrylate
- methyl acrylate
- deuterated methyl
- deuterium
- 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.)
- Granted
Links
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 title claims abstract description 21
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 11
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 abstract description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 5
- 239000007789 gas Substances 0.000 abstract description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract description 3
- 229910052763 palladium Inorganic materials 0.000 abstract description 2
- 229910052697 platinum Inorganic materials 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- -1 etc. Substances 0.000 abstract 1
- 229950000688 phenothiazine Drugs 0.000 abstract 1
- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-WFGJKAKNSA-N deuterated acetone Substances [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 3
- 238000000034 method Methods 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 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
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 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
- 238000005516 engineering process Methods 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
- 150000002739 metals Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000376 reactant 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
- 239000000243 solution 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 |
| EP85116130A EP0186106B1 (en) | 1984-12-21 | 1985-12-18 | 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. |
| 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 true JPS61148141A (ja) | 1986-07-05 |
| JPH0519536B2 JPH0519536B2 (https=) | 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 (https=) |
| EP (1) | EP0186106B1 (https=) |
| JP (1) | JPS61148141A (https=) |
| CA (1) | CA1264330A (https=) |
| DE (1) | DE3582870D1 (https=) |
| NO (1) | NO162662C (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (27)
| 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 |
| WO2005010060A1 (en) * | 2003-07-24 | 2005-02-03 | Fuji Photo Film Co., Ltd. | Heavy-hydrogenated (meth)acrylates, process for producing them, polymers thereof and optical members |
| WO2005010061A1 (en) * | 2003-07-24 | 2005-02-03 | Fuji Photo Film Co., Ltd. | Heavy-hydrogenated norbornyl (meth)acrylates, process for producing them, polymers thereof and optical members |
| US20050114527A1 (en) * | 2003-10-08 | 2005-05-26 | Hankey Michael R. | System and method for personal communication over a global computer network |
| KR20060129284A (ko) * | 2004-01-23 | 2006-12-15 | 와코 쥰야꾸 고교 가부시키가이샤 | 혼합촉매를 사용한 중수소화방법 |
| 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 |
| KR101773643B1 (ko) | 2010-04-28 | 2017-08-31 | 교와 핫꼬 기린 가부시키가이샤 | 양이온성 지질 |
| CN103874697A (zh) | 2011-08-03 | 2014-06-18 | 协和发酵麒麟株式会社 | 二苯并氧杂*衍生物 |
| TW201311693A (zh) | 2011-09-02 | 2013-03-16 | Kyowa Hakko Kirin Co Ltd | 化學激活激素受體活性調節劑 |
| JP2013095755A (ja) | 2011-11-02 | 2013-05-20 | Kyowa Hakko Kirin Co Ltd | カチオン性脂質 |
| KR20140111272A (ko) | 2011-12-12 | 2014-09-18 | 교와 핫꼬 기린 가부시키가이샤 | 양이온성 지질의 조합을 함유하는 지질 나노 입자 |
| JP6182457B2 (ja) | 2011-12-12 | 2017-08-16 | 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クデリバリーシステムのための脂質ナノ粒子 |
| JP6271422B2 (ja) | 2012-06-25 | 2018-01-31 | 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 |
| US9701689B2 (en) | 2012-11-30 | 2017-07-11 | Kyowa Hakko Kirin Co., Ltd. | Substituted pyridines and pyridazines as CCR10 receptor inhibitors |
| TW201441193A (zh) | 2012-12-06 | 2014-11-01 | Kyowa Hakko Kirin Co Ltd | 吡啶酮化合物 |
| SG11201805286RA (en) | 2015-12-24 | 2018-07-30 | Kyowa Hakko Kirin Co Ltd | α,β-UNSATURATED AMIDE COMPOUND |
| US11447471B2 (en) | 2017-06-23 | 2022-09-20 | Kyowa Kirin Co., Ltd. | α,β-unsaturated amide compound |
| US11629152B2 (en) | 2018-03-30 | 2023-04-18 | Kyowa Kirin Co., Ltd. | Compound with anticancer activity |
| CN120623106A (zh) | 2019-09-30 | 2025-09-12 | 协和麒麟株式会社 | Bet降解剂 |
| 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 EP EP85116130A patent/EP0186106B1/en not_active Expired - Lifetime
- 1985-12-18 DE DE8585116130T patent/DE3582870D1/de 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 (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0519536B2 (https=) | 1993-03-17 |
| EP0186106A3 (en) | 1988-01-27 |
| NO162662B (no) | 1989-10-23 |
| NO162662C (no) | 1990-01-31 |
| DE3582870D1 (de) | 1991-06-20 |
| US4874890A (en) | 1989-10-17 |
| CA1264330A (en) | 1990-01-09 |
| EP0186106A2 (en) | 1986-07-02 |
| EP0186106B1 (en) | 1991-05-15 |
| NO855201L (no) | 1986-06-23 |
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