JPH09268155A - α，β−不飽和−β−トリフロオロメチル カルボキシレートの製造方法 - Google Patents
α，β−不飽和−β−トリフロオロメチル カルボキシレートの製造方法Info
- Publication number
- JPH09268155A JPH09268155A JP8289085A JP28908596A JPH09268155A JP H09268155 A JPH09268155 A JP H09268155A JP 8289085 A JP8289085 A JP 8289085A JP 28908596 A JP28908596 A JP 28908596A JP H09268155 A JPH09268155 A JP H09268155A
- Authority
- JP
- Japan
- Prior art keywords
- base
- hydrogen
- independently selected
- ethyl
- structural formula
- 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.)
- Ceased
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 9
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004051 hexyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 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 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical class [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 claims 2
- 239000002904 solvent Substances 0.000 abstract description 24
- 238000006243 chemical reaction Methods 0.000 abstract description 22
- 238000004821 distillation Methods 0.000 abstract description 15
- 239000000126 substance Substances 0.000 abstract description 8
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 230000000975 bioactive effect Effects 0.000 abstract description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 22
- 238000003756 stirring Methods 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- -1 aziridyl Chemical group 0.000 description 11
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- ZWEDFBKLJILTMC-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)C(F)(F)F ZWEDFBKLJILTMC-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FCJBGMJILCJZGF-UHFFFAOYSA-N ethyl 3-acetyloxy-4,4,4-trifluorobutanoate Chemical compound CCOC(=O)CC(C(F)(F)F)OC(C)=O FCJBGMJILCJZGF-UHFFFAOYSA-N 0.000 description 2
- SSCQIQWSUDZYMK-UHFFFAOYSA-N ethyl 3-butanoyloxy-4,4,4-trifluorobutanoate Chemical compound CCCC(=O)OC(C(F)(F)F)CC(=O)OCC SSCQIQWSUDZYMK-UHFFFAOYSA-N 0.000 description 2
- PUIBKAHUQOOLSW-UHFFFAOYSA-N octanedioyl dichloride Chemical compound ClC(=O)CCCCCCC(Cl)=O PUIBKAHUQOOLSW-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 238000003809 water extraction Methods 0.000 description 2
- FUAUOHVIKZJTFL-UHFFFAOYSA-N (4-ethoxy-1,1,1-trifluoro-3-methyl-4-oxobutan-2-yl) 4-methylbenzoate Chemical compound CCOC(=O)C(C)C(C(F)(F)F)OC(=O)C1=CC=C(C)C=C1 FUAUOHVIKZJTFL-UHFFFAOYSA-N 0.000 description 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- FCKHHHXXJZMXBH-UHFFFAOYSA-N 3,3,3-trifluoro-1-nitroprop-1-ene Chemical compound [O-][N+](=O)C=CC(F)(F)F FCKHHHXXJZMXBH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical class COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKRJCMKLCDWROR-ONEGZZNKSA-N ethyl (e)-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)\C=C\C(F)(F)F ZKRJCMKLCDWROR-ONEGZZNKSA-N 0.000 description 1
- ANNZGOFOWCNVBU-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-2-methylbutanoate Chemical compound CCOC(=O)C(C)CC(F)(F)F ANNZGOFOWCNVBU-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (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 |
|---|---|---|---|
| US500495P | 1995-10-10 | 1995-10-10 | |
| US005,004 | 1995-10-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09268155A true JPH09268155A (ja) | 1997-10-14 |
| JPH09268155A5 JPH09268155A5 (enExample) | 2004-10-14 |
Family
ID=21713637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8289085A Ceased JPH09268155A (ja) | 1995-10-10 | 1996-10-11 | α，β−不飽和−β−トリフロオロメチル カルボキシレートの製造方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5679832A (enExample) |
| EP (1) | EP0768296B1 (enExample) |
| JP (1) | JPH09268155A (enExample) |
| CN (1) | CN1121378C (enExample) |
| AT (1) | ATE202071T1 (enExample) |
| AU (1) | AU703560B2 (enExample) |
| BR (1) | BR9605027A (enExample) |
| CA (1) | CA2187060A1 (enExample) |
| DE (1) | DE69613303T2 (enExample) |
| DK (1) | DK0768296T3 (enExample) |
| ES (1) | ES2157403T3 (enExample) |
| GR (1) | GR3036038T3 (enExample) |
| HU (1) | HUP9602789A3 (enExample) |
| IL (1) | IL119331A (enExample) |
| PT (1) | PT768296E (enExample) |
| SG (1) | SG81900A1 (enExample) |
| TW (1) | TW436478B (enExample) |
| ZA (1) | ZA968372B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2019230831A1 (ja) * | 2018-05-31 | 2020-06-18 | クミアイ化学工業株式会社 | 含フッ素ピラゾール誘導体の製造方法及びその中間体 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6545175B1 (en) * | 2000-10-19 | 2003-04-08 | Battelle Memorial Institute | Ester compounds and their use in forming acrylates |
| US6992209B2 (en) * | 2002-12-09 | 2006-01-31 | Battelle Memorial Institute | Methods of forming alpha, beta-unsaturated acids and esters |
| CN100348624C (zh) * | 2005-01-13 | 2007-11-14 | 中国石油化工股份有限公司 | 用于烯烃聚合反应的催化剂组分和催化剂 |
| JP5277837B2 (ja) | 2008-09-26 | 2013-08-28 | セントラル硝子株式会社 | α−トリフルオロメチル−α，β−不飽和エステル類の製造方法 |
| CN102211999A (zh) * | 2011-05-25 | 2011-10-12 | 原平市同利化工有限责任公司 | 2-氟代丙烯酸烷基酯的制备方法 |
| US11133529B2 (en) * | 2015-09-23 | 2021-09-28 | Gotion, Inc. | Fluorinated acrylates as additives for Li-ion battery electrolytes |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5767534A (en) * | 1980-10-16 | 1982-04-24 | Mitsui Toatsu Chem Inc | Preparation of alpha,beta-unsaturated carboxylic ester and alpha,beta-unsaturated carboxylic acid |
| JPS62108845A (ja) * | 1985-11-06 | 1987-05-20 | Central Glass Co Ltd | α−パ−フルオロアルキルビニルエステルの製造法 |
| JP2906547B2 (ja) * | 1990-03-15 | 1999-06-21 | 三菱瓦斯化学株式会社 | α，β―不飽和カルボン酸エステルの製造方法 |
| JP2756373B2 (ja) * | 1991-03-11 | 1998-05-25 | セントラル硝子株式会社 | １，１，１−トリフルオロ−３−ニトロ−２−プロペンの製造方法 |
-
1996
- 1996-09-27 EP EP96307042A patent/EP0768296B1/en not_active Expired - Lifetime
- 1996-09-27 ES ES96307042T patent/ES2157403T3/es not_active Expired - Lifetime
- 1996-09-27 AT AT96307042T patent/ATE202071T1/de not_active IP Right Cessation
- 1996-09-27 PT PT96307042T patent/PT768296E/pt unknown
- 1996-09-27 DE DE69613303T patent/DE69613303T2/de not_active Expired - Fee Related
- 1996-09-27 DK DK96307042T patent/DK0768296T3/da active
- 1996-09-27 AU AU67907/96A patent/AU703560B2/en not_active Ceased
- 1996-09-30 IL IL11933196A patent/IL119331A/xx not_active IP Right Cessation
- 1996-10-03 SG SG9610784A patent/SG81900A1/en unknown
- 1996-10-03 CA CA002187060A patent/CA2187060A1/en not_active Abandoned
- 1996-10-04 ZA ZA968372A patent/ZA968372B/xx unknown
- 1996-10-08 BR BR9605027A patent/BR9605027A/pt active Search and Examination
- 1996-10-08 US US08/727,866 patent/US5679832A/en not_active Expired - Fee Related
- 1996-10-10 HU HU9602789A patent/HUP9602789A3/hu unknown
- 1996-10-10 CN CN96120034A patent/CN1121378C/zh not_active Expired - Fee Related
- 1996-10-11 JP JP8289085A patent/JPH09268155A/ja not_active Ceased
- 1996-11-06 TW TW085113543A patent/TW436478B/zh active
-
2001
- 2001-06-14 GR GR20010400116T patent/GR3036038T3/el not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2019230831A1 (ja) * | 2018-05-31 | 2020-06-18 | クミアイ化学工業株式会社 | 含フッ素ピラゾール誘導体の製造方法及びその中間体 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE202071T1 (de) | 2001-06-15 |
| IL119331A0 (en) | 1996-12-05 |
| HUP9602789A2 (en) | 1997-10-28 |
| DE69613303D1 (de) | 2001-07-19 |
| IL119331A (en) | 1999-12-22 |
| ES2157403T3 (es) | 2001-08-16 |
| BR9605027A (pt) | 1998-06-30 |
| TW436478B (en) | 2001-05-28 |
| US5679832A (en) | 1997-10-21 |
| GR3036038T3 (en) | 2001-09-28 |
| EP0768296B1 (en) | 2001-06-13 |
| SG81900A1 (en) | 2001-07-24 |
| HU9602789D0 (en) | 1996-11-28 |
| CA2187060A1 (en) | 1997-04-11 |
| AU6790796A (en) | 1997-04-17 |
| ZA968372B (en) | 1997-04-10 |
| AU703560B2 (en) | 1999-03-25 |
| CN1121378C (zh) | 2003-09-17 |
| CN1160708A (zh) | 1997-10-01 |
| EP0768296A1 (en) | 1997-04-16 |
| PT768296E (pt) | 2001-10-30 |
| DK0768296T3 (da) | 2001-09-03 |
| DE69613303T2 (de) | 2001-11-22 |
| HUP9602789A3 (en) | 1999-01-28 |
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