HU216742B - Eljárás O-(2-hidroxi-alkil)-oximok előállítására - Google Patents
Eljárás O-(2-hidroxi-alkil)-oximok előállítására Download PDFInfo
- Publication number
- HU216742B HU216742B HU9700313A HU9700313A HU216742B HU 216742 B HU216742 B HU 216742B HU 9700313 A HU9700313 A HU 9700313A HU 9700313 A HU9700313 A HU 9700313A HU 216742 B HU216742 B HU 216742B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- oxime
- process according
- ketoxime
- dioxolan
- Prior art date
Links
- 150000002923 oximes Chemical class 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- -1 alkali metal salt Chemical class 0.000 claims description 9
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000004714 phosphonium salts Chemical class 0.000 claims description 6
- 239000011736 potassium bicarbonate Substances 0.000 claims description 6
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 6
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 6
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical group [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001449 anionic compounds Chemical class 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 150000002891 organic anions Chemical class 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 abstract description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000004821 distillation Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 4
- 239000003444 phase transfer catalyst Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZOJIBRUWYLWNRB-UHFFFAOYSA-N 2-(2-ethenoxyethoxymethyl)oxirane Chemical compound C=COCCOCC1CO1 ZOJIBRUWYLWNRB-UHFFFAOYSA-N 0.000 description 1
- OSXTUIDVWYUNOO-UHFFFAOYSA-N 2-(3-hydroxyiminobutan-2-ylideneamino)oxyethanol Chemical compound CC(=NO)C(C)=NOCCO OSXTUIDVWYUNOO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- MGZDDCVCLLEWOR-UHFFFAOYSA-N acetic acid;tributylphosphane Chemical compound CC(O)=O.CCCCP(CCCC)CCCC MGZDDCVCLLEWOR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BMDRYIFEJILWIP-UHFFFAOYSA-M butyl(triethyl)azanium;chloride Chemical group [Cl-].CCCC[N+](CC)(CC)CC BMDRYIFEJILWIP-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910001412 inorganic anion Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4427289 | 1994-08-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT77753A HUT77753A (hu) | 1998-07-28 |
| HU216742B true HU216742B (hu) | 1999-08-30 |
Family
ID=6524699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9700313A HU216742B (hu) | 1994-08-02 | 1995-07-28 | Eljárás O-(2-hidroxi-alkil)-oximok előállítására |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0775107B1 (enExample) |
| JP (1) | JP4017022B2 (enExample) |
| KR (1) | KR100388882B1 (enExample) |
| CN (1) | CN1086383C (enExample) |
| AT (1) | ATE185553T1 (enExample) |
| AU (1) | AU3381395A (enExample) |
| BR (1) | BR9508498A (enExample) |
| CA (1) | CA2196452A1 (enExample) |
| DE (1) | DE69512786T2 (enExample) |
| DK (1) | DK0775107T3 (enExample) |
| ES (1) | ES2139935T3 (enExample) |
| GR (1) | GR3031531T3 (enExample) |
| HU (1) | HU216742B (enExample) |
| IL (1) | IL114776A (enExample) |
| MX (1) | MX9700809A (enExample) |
| WO (1) | WO1996004238A1 (enExample) |
| ZA (1) | ZA956402B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000078710A1 (en) * | 1999-06-23 | 2000-12-28 | Alliedsignal Inc. | Method of making hydroxylamine salts |
| CN107531617B (zh) * | 2015-05-22 | 2020-10-02 | 日产化学工业株式会社 | O-[1-(2-羟基丙基)]肟化合物的制造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965177A (en) * | 1972-05-03 | 1976-06-22 | Texaco Inc. | Catalytic process |
| US5434306A (en) * | 1993-11-25 | 1995-07-18 | Ciba-Geigy Corporation | Process for the preparation of O-substituted oximes |
-
1995
- 1995-07-28 IL IL11477695A patent/IL114776A/xx not_active IP Right Cessation
- 1995-07-28 BR BR9508498A patent/BR9508498A/pt not_active IP Right Cessation
- 1995-07-28 AU AU33813/95A patent/AU3381395A/en not_active Abandoned
- 1995-07-28 EP EP95930419A patent/EP0775107B1/en not_active Expired - Lifetime
- 1995-07-28 CN CN95194843A patent/CN1086383C/zh not_active Expired - Lifetime
- 1995-07-28 MX MX9700809A patent/MX9700809A/es not_active IP Right Cessation
- 1995-07-28 WO PCT/EP1995/003001 patent/WO1996004238A1/en not_active Ceased
- 1995-07-28 JP JP50618096A patent/JP4017022B2/ja not_active Expired - Lifetime
- 1995-07-28 AT AT95930419T patent/ATE185553T1/de active
- 1995-07-28 ES ES95930419T patent/ES2139935T3/es not_active Expired - Lifetime
- 1995-07-28 DE DE69512786T patent/DE69512786T2/de not_active Expired - Lifetime
- 1995-07-28 KR KR1019970700696A patent/KR100388882B1/ko not_active Expired - Lifetime
- 1995-07-28 HU HU9700313A patent/HU216742B/hu not_active IP Right Cessation
- 1995-07-28 CA CA002196452A patent/CA2196452A1/en not_active Abandoned
- 1995-07-28 DK DK95930419T patent/DK0775107T3/da active
- 1995-08-01 ZA ZA9506402A patent/ZA956402B/xx unknown
-
1999
- 1999-10-14 GR GR990402548T patent/GR3031531T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69512786T2 (de) | 2000-03-02 |
| BR9508498A (pt) | 1997-12-30 |
| JPH10506617A (ja) | 1998-06-30 |
| ATE185553T1 (de) | 1999-10-15 |
| EP0775107B1 (en) | 1999-10-13 |
| EP0775107A1 (en) | 1997-05-28 |
| ES2139935T3 (es) | 2000-02-16 |
| ZA956402B (en) | 1997-02-03 |
| CN1156445A (zh) | 1997-08-06 |
| DE69512786D1 (de) | 1999-11-18 |
| CN1086383C (zh) | 2002-06-19 |
| WO1996004238A1 (en) | 1996-02-15 |
| GR3031531T3 (en) | 2000-01-31 |
| DK0775107T3 (da) | 1999-12-27 |
| HUT77753A (hu) | 1998-07-28 |
| JP4017022B2 (ja) | 2007-12-05 |
| MX9700809A (es) | 1997-05-31 |
| IL114776A0 (en) | 1995-11-27 |
| CA2196452A1 (en) | 1996-02-15 |
| AU3381395A (en) | 1996-03-04 |
| KR100388882B1 (ko) | 2004-03-31 |
| KR970704671A (ko) | 1997-09-06 |
| IL114776A (en) | 2000-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20020058829A1 (en) | Synthesis of vinyl carbonates for use in producing vinyl carbamates | |
| HU216742B (hu) | Eljárás O-(2-hidroxi-alkil)-oximok előállítására | |
| US4174347A (en) | Preparation of esters | |
| EP0675130B1 (en) | Process for the preparation of phosphonium salts | |
| HU194173B (en) | Process for preparing substituted pyridine | |
| HU189752B (en) | Process for production of benzoxazoliloxi- and benztiazoliloxipropion and derivates | |
| KR960012208B1 (ko) | 우레아, 카바메이트 및 카바메이트 유도체의 제조방법 | |
| US4223166A (en) | Process for producing 4-bromo-2-chlorophenols | |
| US4418017A (en) | Preparation of phenylacetonitriles carrying basic substituents | |
| US5852216A (en) | Preparation and use of (3-alkoxy-phenyl) magnesium chlorides | |
| CS197286B2 (en) | Process for preparing alpha-cyanobenzylesteres of alkanoic and cycloalkanoic acids | |
| CA1087618A (en) | Process for preparing perfluoro-4-oxo-2,5-dimethyl-2- fluorocarbonyl-1,3-dioxolane | |
| CA1069921A (en) | Esters | |
| US5910617A (en) | Process for the preparation of aliphatic or cycloaliphatic chlorides | |
| US4332729A (en) | Preparation of cyclic carbonates | |
| US4260782A (en) | Process for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines | |
| US10160694B2 (en) | Agent for introducing protecting group for hydroxy group and/or mercapto group | |
| US4267356A (en) | Process for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines | |
| US4266071A (en) | Process for the preparation of N-(1-alkoxycarbonylethyl)-2,6-dialkylanilines | |
| EP0255650B1 (de) | Verfahren zur Herstellung von Indanen | |
| EP0220792B1 (en) | A method for producing 2-aryl-propionaldehydes | |
| EP1092709A1 (en) | Process for producing beta-carotene | |
| JP4693840B2 (ja) | ハロアルキルエーテル化合物の製造方法 | |
| US4594467A (en) | Preparation of 3,5-dichloro-α-methylstyrene | |
| EP0003866B1 (en) | 3-azabicyclo(3.1.0)hexane derivatives and a process for their preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of definitive patent protection due to non-payment of fees |