JPS6210979B2 - - Google Patents
Info
- Publication number
- JPS6210979B2 JPS6210979B2 JP810879A JP810879A JPS6210979B2 JP S6210979 B2 JPS6210979 B2 JP S6210979B2 JP 810879 A JP810879 A JP 810879A JP 810879 A JP810879 A JP 810879A JP S6210979 B2 JPS6210979 B2 JP S6210979B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction mixture
- weight
- inert solvent
- acetone
- 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
Links
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- 150000004702 methyl esters Chemical class 0.000 claims description 17
- 239000012442 inert solvent Substances 0.000 claims description 14
- 239000000376 reactant Substances 0.000 claims description 12
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims description 10
- MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 claims description 10
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UCJOAMOXKLJGST-UHFFFAOYSA-N n-propan-2-ylpropan-2-imine Chemical compound CC(C)N=C(C)C UCJOAMOXKLJGST-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical group CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes 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
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7800982A NL7800982A (nl) | 1978-01-27 | 1978-01-27 | Werkwijze ter bereiding van de methylester 4-oxopentaan-1-carbonzuur. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54112823A JPS54112823A (en) | 1979-09-04 |
| JPS6210979B2 true JPS6210979B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-03-10 |
Family
ID=19830232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP810879A Granted JPS54112823A (en) | 1978-01-27 | 1979-01-26 | Method of manufacturing methylester of 44oxopentanee11carboxylic acid |
Country Status (5)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1212382A (en) * | 1982-04-26 | 1986-10-07 | Koppers Company, Inc. | Liquid-phase preparation of delta-keto carboxylic acid esters utilizing liquid-phase insoluble catalyst |
| CN116143622A (zh) * | 2022-12-06 | 2023-05-23 | 浙江工业大学 | 一种环己二酮中间体5-氧代己酸甲酯的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2325160A1 (de) * | 1973-05-18 | 1974-12-05 | Hoechst Ag | Verfahren zur herstellung von 5-oxocarbonsaeureestern |
| DE2540972C3 (de) * | 1975-09-13 | 1979-03-22 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 5-Oxohexansäure und deren Derivaten |
-
1978
- 1978-01-27 NL NL7800982A patent/NL7800982A/xx not_active Application Discontinuation
-
1979
- 1979-01-25 EP EP19790200049 patent/EP0003624B1/en not_active Expired
- 1979-01-25 DE DE7979200049T patent/DE2963387D1/de not_active Expired
- 1979-01-26 JP JP810879A patent/JPS54112823A/ja active Granted
- 1979-01-26 CA CA000320352A patent/CA1148563A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7800982A (nl) | 1979-07-31 |
| EP0003624B1 (en) | 1982-07-28 |
| CA1148563A (en) | 1983-06-21 |
| EP0003624A1 (en) | 1979-08-22 |
| DE2963387D1 (en) | 1982-09-16 |
| JPS54112823A (en) | 1979-09-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101210196B1 (ko) | 포름산의 제조 방법 | |
| US8686181B2 (en) | Method for producing ethylene glycol dimethacrylate | |
| US5292917A (en) | Process for purifying dimethyl carbonate | |
| JP2006509024A (ja) | 乳酸エチルの連続製造方法 | |
| JP4520310B2 (ja) | （メタ）アクリル酸ｎ−アルキルアミノアルキルエステルの製造方法 | |
| JP2002511081A (ja) | 不飽和ジカルボン酸無水物のジメチルエステルを生成する方法 | |
| EP0501374B1 (en) | Process for purifying dimethyl carbonate | |
| JPS63165365A (ja) | カプロラクタムの製造法 | |
| JPS6210979B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JP3608927B2 (ja) | 飽和脂肪族カルボン酸アミドの製造方法 | |
| JP2537955B2 (ja) | マレイン酸ジメチルの製造方法 | |
| US4968834A (en) | Recovery of acrylic acid and/or ethyl acrylate from black acid | |
| US4117000A (en) | Process for preparing 4-oxocapronitrile | |
| US3979443A (en) | Process for the preparation of esters of maleic acid with monohydric alcohols | |
| US6235924B1 (en) | Continuous process for preparing benzoic acid esters | |
| US5217582A (en) | Process for the isolation of alkyl glyoxylate | |
| JP2676910B2 (ja) | 高純度０‐トルイル酸の製造法 | |
| EP0060719A1 (en) | Process for the production of methyl acetate by esterifying methanol with acetic acid | |
| JP3682805B2 (ja) | 飽和脂肪族カルボン酸アミドの製造方法 | |
| JPS60500091A (ja) | ジハイドロカルビル オキサレ−トの製造方法 | |
| EP0074162A1 (en) | Process for producing p-cresol | |
| JPS63303937A (ja) | プロピノールの製造方法 | |
| JP4356342B2 (ja) | エチレングリコールの精製方法 | |
| JP2844382B2 (ja) | 貯蔵安定性レブリン酸の製造方法 | |
| JPH0737431B2 (ja) | テレフタル酸ジアニリド類の製造法 |