CA1264330A - Process for the production of deuterated methyl acrylate or deuterated methyl methacrylate - Google Patents
Process for the production of deuterated methyl acrylate or deuterated methyl methacrylateInfo
- Publication number
- CA1264330A CA1264330A CA000497590A CA497590A CA1264330A CA 1264330 A CA1264330 A CA 1264330A CA 000497590 A CA000497590 A CA 000497590A CA 497590 A CA497590 A CA 497590A CA 1264330 A CA1264330 A CA 1264330A
- Authority
- CA
- Canada
- Prior art keywords
- methyl methacrylate
- deuterated
- methyl acrylate
- deuterium
- deuterated methyl
- 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 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims description 27
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical class [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000006467 substitution reaction Methods 0.000 claims abstract description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 3
- 239000002184 metal Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 2
- 229940063557 methacrylate Drugs 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229940102838 methylmethacrylate Drugs 0.000 description 9
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical class CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 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
- -1 deuterated acetone cyanohydrin fromdeuterated acetone Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 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
- MJBPUQUGJNAPAZ-AWEZNQCLSA-N butin Chemical compound C1([C@@H]2CC(=O)C3=CC=C(C=C3O2)O)=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-AWEZNQCLSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction 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
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 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
- 239000005909 Kieselgur Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 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
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 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
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 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
- 150000003467 sulfuric acid derivatives Chemical class 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP270319/84 | 1984-12-21 | ||
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1264330A true CA1264330A (en) | 1990-01-09 |
Family
ID=17484607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000497590A Expired - Lifetime CA1264330A (en) | 1984-12-21 | 1985-12-13 | Process for the production of deuterated methyl acrylate or deuterated methyl methacrylate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4874890A (enExample) |
| EP (1) | EP0186106B1 (enExample) |
| JP (1) | JPS61148141A (enExample) |
| CA (1) | CA1264330A (enExample) |
| DE (1) | DE3582870D1 (enExample) |
| NO (1) | NO162662C (enExample) |
Families Citing this family (28)
| 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 |
| 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 |
| US8969345B2 (en) | 2011-08-03 | 2015-03-03 | Kyowa Hakko Kirin Co., Ltd. | Dibenzooxepin derivative |
| KR20140075698A (ko) | 2011-09-02 | 2014-06-19 | 교와 핫꼬 기린 가부시키가이샤 | 케모카인 수용체 활성 조절제 |
| JP2013095755A (ja) | 2011-11-02 | 2013-05-20 | Kyowa Hakko Kirin Co Ltd | カチオン性脂質 |
| CN104159615B (zh) | 2011-12-12 | 2017-08-18 | 协和发酵麒麟株式会社 | 含有阳离子性脂质的组合的脂质纳米粒子 |
| US9839616B2 (en) | 2011-12-12 | 2017-12-12 | Kyowa Hakko Kirin Co., Ltd. | Lipid nano particles comprising cationic lipid for drug delivery system |
| 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 |
| AU2013353004A1 (en) | 2012-11-30 | 2015-07-09 | Kyowa Hakko Kirin Co., Ltd. | Nitrogen-containing heterocyclic compound |
| TW201441193A (zh) | 2012-12-06 | 2014-11-01 | Kyowa Hakko Kirin Co Ltd | 吡啶酮化合物 |
| AU2016379292B2 (en) | 2015-12-24 | 2021-03-25 | Kyowa Kirin Co., Ltd. | α, β unsaturated amide compound |
| AU2018289759B2 (en) | 2017-06-23 | 2022-03-10 | Kyowa Kirin Co., Ltd. | Alpha, beta-unsaturated amide compound |
| US11629152B2 (en) | 2018-03-30 | 2023-04-18 | Kyowa Kirin Co., Ltd. | Compound with anticancer activity |
| JP7642552B2 (ja) | 2019-09-30 | 2025-03-10 | 協和キリン株式会社 | Ｂｅｔ分解剤 |
| 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
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 |
| JPH0519536B2 (enExample) | 1993-03-17 |
| JPS61148141A (ja) | 1986-07-05 |
| NO162662B (no) | 1989-10-23 |
| NO855201L (no) | 1986-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |