JPS602296B2 - 不飽和カルボン酸およびその製法 - Google Patents
不飽和カルボン酸およびその製法Info
- Publication number
- JPS602296B2 JPS602296B2 JP51129567A JP12956776A JPS602296B2 JP S602296 B2 JPS602296 B2 JP S602296B2 JP 51129567 A JP51129567 A JP 51129567A JP 12956776 A JP12956776 A JP 12956776A JP S602296 B2 JPS602296 B2 JP S602296B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- salt
- formula
- carboxylic acid
- unsaturated carboxylic
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 6
- -1 carbon atoms carboxylic acid Chemical class 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- KGUVNWFNGFCCKR-UHFFFAOYSA-N 2-cyano-3,3-dimethylpent-4-enoic acid Chemical compound C=CC(C)(C)C(C#N)C(O)=O KGUVNWFNGFCCKR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 159000000014 iron salts Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- YTTWDTVYXAEAJA-UHFFFAOYSA-N 2,2-dimethyl-hexanoic acid Chemical compound CCCCC(C)(C)C(O)=O YTTWDTVYXAEAJA-UHFFFAOYSA-N 0.000 description 1
- CYYDDSNDKQYALZ-UHFFFAOYSA-N 2-cyanohexanoic acid Chemical class CCCCC(C#N)C(O)=O CYYDDSNDKQYALZ-UHFFFAOYSA-N 0.000 description 1
- OGRUNLRQTBVLAP-UHFFFAOYSA-N 2-ethoxycarbonyl-3,3-dimethylpent-4-enoic acid Chemical compound CCOC(=O)C(C(O)=O)C(C)(C)C=C OGRUNLRQTBVLAP-UHFFFAOYSA-N 0.000 description 1
- LZLSUHMFFPVWGU-UHFFFAOYSA-N 3-methylbut-2-enyl 2-cyanoacetate Chemical compound CC(C)=CCOC(=O)CC#N LZLSUHMFFPVWGU-UHFFFAOYSA-N 0.000 description 1
- IVUPBSLRQYWNKZ-UHFFFAOYSA-N 4,6,6,6-tetrachloro-2-cyano-3,3-dimethylhexanoic acid Chemical compound N#CC(C(O)=O)C(C)(C)C(Cl)CC(Cl)(Cl)Cl IVUPBSLRQYWNKZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- HDITUCONWLWUJR-UHFFFAOYSA-N diethylazanium;chloride Chemical compound [Cl-].CC[NH2+]CC HDITUCONWLWUJR-UHFFFAOYSA-N 0.000 description 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical class [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB45155/75A GB1556999A (en) | 1975-10-31 | 1975-10-31 | Unsaturated carboxylic acids |
| GB45155/1975 | 1975-10-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5257118A JPS5257118A (en) | 1977-05-11 |
| JPS602296B2 true JPS602296B2 (ja) | 1985-01-21 |
Family
ID=10436104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51129567A Expired JPS602296B2 (ja) | 1975-10-31 | 1976-10-29 | 不飽和カルボン酸およびその製法 |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS602296B2 (cs) |
| AU (1) | AU502376B2 (cs) |
| BR (1) | BR7607252A (cs) |
| CA (1) | CA1086329A (cs) |
| CH (1) | CH624380A5 (cs) |
| DD (1) | DD127238A5 (cs) |
| DE (1) | DE2649711C2 (cs) |
| DK (1) | DK155001C (cs) |
| ES (1) | ES452860A1 (cs) |
| FR (1) | FR2329649A1 (cs) |
| GB (1) | GB1556999A (cs) |
| IL (1) | IL50795A (cs) |
| IT (1) | IT1075871B (cs) |
| MX (1) | MX3822E (cs) |
| NL (1) | NL187205C (cs) |
| SE (1) | SE7612068L (cs) |
| SU (1) | SU668591A3 (cs) |
| TR (1) | TR19157A (cs) |
| ZA (1) | ZA766490B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1128958A (en) * | 1977-09-19 | 1982-08-03 | Johannes L.M. Syrier | Preparation of an alkenyl cyanoacetate |
| CA1182469A (en) * | 1981-12-11 | 1985-02-12 | William D. Emmons | Esters of michael addition homopolymers of acrylic acid |
| AU688403B2 (en) * | 1993-11-03 | 1998-03-12 | Commonwealth Scientific And Industrial Research Organisation | Allylic chain transfer agents |
| IL111484A (en) * | 1993-11-03 | 2001-06-14 | Commw Scient Ind Res Org | Polymerization process using pendant chain transfer means to regulate the molecular weight, the polymers thus obtained and a number of new pesticide compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2326077C2 (de) * | 1972-05-25 | 1985-12-12 | National Research Development Corp., London | Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide |
-
1975
- 1975-10-31 GB GB45155/75A patent/GB1556999A/en not_active Expired
-
1976
- 1976-09-14 CA CA261,226A patent/CA1086329A/en not_active Expired
- 1976-10-27 TR TR19157A patent/TR19157A/xx unknown
- 1976-10-28 NL NLAANVRAGE7611939,A patent/NL187205C/xx not_active IP Right Cessation
- 1976-10-29 MX MX765034U patent/MX3822E/es unknown
- 1976-10-29 AU AU19145/76A patent/AU502376B2/en not_active Expired
- 1976-10-29 JP JP51129567A patent/JPS602296B2/ja not_active Expired
- 1976-10-29 IL IL50795A patent/IL50795A/xx unknown
- 1976-10-29 FR FR7632778A patent/FR2329649A1/fr active Granted
- 1976-10-29 SE SE7612068A patent/SE7612068L/xx unknown
- 1976-10-29 SU SU762415403A patent/SU668591A3/ru active
- 1976-10-29 ZA ZA766490A patent/ZA766490B/xx unknown
- 1976-10-29 DK DK492576A patent/DK155001C/da not_active IP Right Cessation
- 1976-10-29 IT IT28901/76A patent/IT1075871B/it active
- 1976-10-29 ES ES452860A patent/ES452860A1/es not_active Expired
- 1976-10-29 CH CH1370076A patent/CH624380A5/de not_active IP Right Cessation
- 1976-10-29 DE DE2649711A patent/DE2649711C2/de not_active Expired
- 1976-10-29 DD DD195534A patent/DD127238A5/xx unknown
- 1976-10-29 BR BR7607252A patent/BR7607252A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL50795A (en) | 1980-02-29 |
| GB1556999A (en) | 1979-12-05 |
| DK155001B (da) | 1989-01-23 |
| DE2649711A1 (de) | 1977-05-05 |
| DK492576A (da) | 1977-05-01 |
| FR2329649A1 (fr) | 1977-05-27 |
| NL7611939A (nl) | 1977-05-03 |
| ZA766490B (en) | 1977-10-26 |
| TR19157A (tr) | 1978-06-01 |
| DK155001C (da) | 1989-06-05 |
| JPS5257118A (en) | 1977-05-11 |
| IT1075871B (it) | 1985-04-22 |
| FR2329649B1 (cs) | 1979-09-21 |
| AU1914576A (en) | 1978-05-04 |
| BR7607252A (pt) | 1977-09-13 |
| ES452860A1 (es) | 1977-10-16 |
| DE2649711C2 (de) | 1985-01-10 |
| CA1086329A (en) | 1980-09-23 |
| NL187205C (nl) | 1991-07-01 |
| SU668591A3 (ru) | 1979-06-15 |
| DD127238A5 (cs) | 1977-09-14 |
| CH624380A5 (en) | 1981-07-31 |
| MX3822E (es) | 1981-07-31 |
| NL187205B (nl) | 1991-02-01 |
| SE7612068L (sv) | 1977-05-01 |
| AU502376B2 (en) | 1979-07-26 |
| IL50795A0 (en) | 1976-12-31 |
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