JPH09323953A - 酸塩化物の調製のための加圧下での酸及び/又は酸無水物のホスゲン化 - Google Patents
酸塩化物の調製のための加圧下での酸及び/又は酸無水物のホスゲン化Info
- Publication number
- JPH09323953A JPH09323953A JP9044230A JP4423097A JPH09323953A JP H09323953 A JPH09323953 A JP H09323953A JP 9044230 A JP9044230 A JP 9044230A JP 4423097 A JP4423097 A JP 4423097A JP H09323953 A JPH09323953 A JP H09323953A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- substituted
- phosgene
- process according
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims abstract description 40
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 150000008065 acid anhydrides Chemical class 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 41
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 40
- 230000008569 process Effects 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 238000007872 degassing Methods 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 19
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 17
- 239000012429 reaction media Substances 0.000 description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 11
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 6
- 235000010233 benzoic acid Nutrition 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000008117 stearic acid Substances 0.000 description 6
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical group CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 4
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 2
- 229910052594 sapphire Inorganic materials 0.000 description 2
- 239000010980 sapphire Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- DFPWNNNCJDHVEY-UHFFFAOYSA-N [F].FC(C(=O)O)(F)F Chemical compound [F].FC(C(=O)O)(F)F DFPWNNNCJDHVEY-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- WPYMKLBDIGXBTP-CDYZYAPPSA-N benzene(13C)carboxylic acid Chemical compound O[13C](=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-CDYZYAPPSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- CASUWTAPYGBPLM-UHFFFAOYSA-M bis(dibutylamino)methylidene-dibutylazanium;chloride Chemical compound [Cl-].CCCCN(CCCC)C(N(CCCC)CCCC)=[N+](CCCC)CCCC CASUWTAPYGBPLM-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- -1 dicarboxylic acid chlorides Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9602795 | 1996-02-29 | ||
| FR9602795A FR2745567B1 (fr) | 1996-02-29 | 1996-02-29 | Phosgenation sous pression des acides pour la prodution des chlorures d'acides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09323953A true JPH09323953A (ja) | 1997-12-16 |
| JPH09323953A5 JPH09323953A5 (fr) | 2004-12-16 |
Family
ID=9489904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9044230A Pending JPH09323953A (ja) | 1996-02-29 | 1997-02-27 | 酸塩化物の調製のための加圧下での酸及び/又は酸無水物のホスゲン化 |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPH09323953A (fr) |
| KR (1) | KR100599065B1 (fr) |
| CN (1) | CN1071303C (fr) |
| BR (1) | BR9700326A (fr) |
| DE (1) | DE19707285A1 (fr) |
| FR (2) | FR2745567B1 (fr) |
| GB (1) | GB2310661B (fr) |
| HU (1) | HU222273B1 (fr) |
| IL (1) | IL120272A0 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007108046A (ja) * | 2005-10-14 | 2007-04-26 | Idemitsu Kosan Co Ltd | 二層分離温度測定装置およびその測定方法 |
| WO2009116435A1 (fr) * | 2008-03-18 | 2009-09-24 | 三井化学アグロ株式会社 | Procédé de fabrication d'un dérivé d'acide acylacétique contenant du fluor, procédé de fabrication d'un dérivé d'ester d'acide carboxylique pyrazole contenant du fluor et procédé de fabrication d'un dérivé d'acide carboxylique pyrazole contenant du fluor |
| CN105384641A (zh) * | 2015-10-26 | 2016-03-09 | 安徽广信农化股份有限公司 | 一种对硝基苯甲酰氯的废水处理工艺 |
| CN105384640A (zh) * | 2015-10-26 | 2016-03-09 | 安徽广信农化股份有限公司 | 一种对硝基苯甲酰氯的尾气处理工艺 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104072347B (zh) * | 2014-06-30 | 2016-07-13 | 湖南海利化工股份有限公司 | 4-烷氧基-1,1,1-三氟-3-丁烯-2-酮的制备方法 |
| CN105254505A (zh) * | 2015-10-26 | 2016-01-20 | 安徽广信农化股份有限公司 | 一种对硝基苯甲酰氯的精制工艺 |
| CN105524017B (zh) * | 2015-12-24 | 2017-06-30 | 江苏瀚联生物科技有限公司 | 2‑甲基氨基‑5‑叔丁基‑1,3,4‑噻二唑的制备方法 |
| CN105585478A (zh) * | 2016-03-08 | 2016-05-18 | 天津市敬业精细化工有限公司 | 一种酰氯的制备方法 |
| CN106674166B (zh) * | 2016-12-20 | 2018-09-25 | 重庆市化工研究院 | 呋喃甲酰氯的制备方法 |
| CN113402383A (zh) * | 2020-03-17 | 2021-09-17 | 上海祖玥新材料科技有限公司 | 一种2-乙基己酸与光气反应合成2-乙基己酰氯的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB402328A (en) * | 1932-04-29 | 1933-11-30 | Ig Farbenindustrie Ag | Improvements in the manufacture of acetyl-chloride |
| NL175521C (nl) * | 1973-04-26 | 1984-11-16 | Hoechst Ag | Werkwijze voor het bereiden van carbonzuurchloriden. |
| FR2232532A1 (en) * | 1973-06-05 | 1975-01-03 | Poudres & Explosifs Ste Nale | Gas phase acid chloride prodn. - from acid and phosgene in presence of active carbon catalyst |
| DE3535984A1 (de) * | 1985-10-09 | 1987-04-09 | Bayer Ag | Verfahren zur herstellung von aromatischen carbonsaeurechloriden |
| DE4129822A1 (de) * | 1991-09-07 | 1993-03-11 | Basf Ag | Verfahren zur herstellung von carbonsaeurehalogeniden |
-
1996
- 1996-02-29 FR FR9602795A patent/FR2745567B1/fr not_active Expired - Fee Related
-
1997
- 1997-02-20 IL IL12027297A patent/IL120272A0/xx unknown
- 1997-02-24 DE DE19707285A patent/DE19707285A1/de not_active Withdrawn
- 1997-02-25 FR FR9702461A patent/FR2745568B1/fr not_active Expired - Fee Related
- 1997-02-25 KR KR1019970005815A patent/KR100599065B1/ko not_active Expired - Fee Related
- 1997-02-27 JP JP9044230A patent/JPH09323953A/ja active Pending
- 1997-02-27 GB GB9704047A patent/GB2310661B/en not_active Expired - Fee Related
- 1997-02-28 BR BR9700326A patent/BR9700326A/pt not_active IP Right Cessation
- 1997-02-28 CN CN97104714A patent/CN1071303C/zh not_active Expired - Fee Related
- 1997-02-28 HU HU9700535A patent/HU222273B1/hu not_active IP Right Cessation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007108046A (ja) * | 2005-10-14 | 2007-04-26 | Idemitsu Kosan Co Ltd | 二層分離温度測定装置およびその測定方法 |
| WO2009116435A1 (fr) * | 2008-03-18 | 2009-09-24 | 三井化学アグロ株式会社 | Procédé de fabrication d'un dérivé d'acide acylacétique contenant du fluor, procédé de fabrication d'un dérivé d'ester d'acide carboxylique pyrazole contenant du fluor et procédé de fabrication d'un dérivé d'acide carboxylique pyrazole contenant du fluor |
| US8344156B2 (en) | 2008-03-18 | 2013-01-01 | Mitsui Chemicals Agro, Inc. | Method for producing fluorine-containing acylacetic acid derivative, method for producing fluorine-containing pyrazolecarboxylic acid ester derivative, and method for producing fluorine-containing pyrazolecarboxylic acid derivative |
| JP5199337B2 (ja) * | 2008-03-18 | 2013-05-15 | 三井化学アグロ株式会社 | 含フッ素アシル酢酸誘導体の製造方法、含フッ素ピラゾールカルボン酸エステル誘導体の製造方法及び含フッ素ピラゾールカルボン酸誘導体の製造方法 |
| CN105384641A (zh) * | 2015-10-26 | 2016-03-09 | 安徽广信农化股份有限公司 | 一种对硝基苯甲酰氯的废水处理工艺 |
| CN105384640A (zh) * | 2015-10-26 | 2016-03-09 | 安徽广信农化股份有限公司 | 一种对硝基苯甲酰氯的尾气处理工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| HU222273B1 (hu) | 2003-05-28 |
| FR2745568B1 (fr) | 1998-08-21 |
| GB9704047D0 (en) | 1997-04-16 |
| FR2745568A1 (fr) | 1997-09-05 |
| FR2745567B1 (fr) | 1998-04-10 |
| GB2310661B (en) | 1998-12-02 |
| HUP9700535A3 (en) | 1999-06-28 |
| FR2745567A1 (fr) | 1997-09-05 |
| CN1163881A (zh) | 1997-11-05 |
| DE19707285A1 (de) | 1997-09-04 |
| IL120272A0 (en) | 1997-06-10 |
| KR100599065B1 (ko) | 2006-12-05 |
| BR9700326A (pt) | 1998-10-27 |
| GB2310661A (en) | 1997-09-03 |
| KR970061845A (ko) | 1997-09-12 |
| HUP9700535A2 (hu) | 1998-06-29 |
| HU9700535D0 (en) | 1997-04-28 |
| CN1071303C (zh) | 2001-09-19 |
Similar Documents
| Publication | Publication Date | Title |
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