OA10675A - Process for the production of azomethines and alphahaloacetanilides - Google Patents
Process for the production of azomethines and alphahaloacetanilides Download PDFInfo
- Publication number
- OA10675A OA10675A OA9800033A OA9800033A OA10675A OA 10675 A OA10675 A OA 10675A OA 9800033 A OA9800033 A OA 9800033A OA 9800033 A OA9800033 A OA 9800033A OA 10675 A OA10675 A OA 10675A
- Authority
- OA
- OAPI
- Prior art keywords
- process according
- evaporators
- reaction
- azomethine
- conducted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 238000001704 evaporation Methods 0.000 claims abstract description 3
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 239000011552 falling film Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 10
- 238000010923 batch production Methods 0.000 abstract description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 5
- 230000008020 evaporation Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- PCJKDSWECWZMRV-UHFFFAOYSA-N 2-chloro-n-(chloromethyl)-n-phenylacetamide Chemical compound ClCC(=O)N(CCl)C1=CC=CC=C1 PCJKDSWECWZMRV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- GGCJLWBMJYGIRE-UHFFFAOYSA-N ethanol;formaldehyde Chemical compound O=C.CCO GGCJLWBMJYGIRE-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- PPHQUIPUBYPZLD-UHFFFAOYSA-N n-ethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
- LDGCMTNKOLBWDY-UHFFFAOYSA-N 3-ethoxy-n-phenylpropanamide Chemical compound CCOCCC(=O)NC1=CC=CC=C1 LDGCMTNKOLBWDY-UHFFFAOYSA-N 0.000 description 1
- 239000010963 304 stainless steel Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000241985 Cnides Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 229910000589 SAE 304 stainless steel Inorganic materials 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US418195P | 1995-09-22 | 1995-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA10675A true OA10675A (en) | 2002-09-25 |
Family
ID=21709569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA9800033A OA10675A (en) | 1995-09-22 | 1998-03-20 | Process for the production of azomethines and alphahaloacetanilides |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5852215A (es) |
| EP (1) | EP0853611B1 (es) |
| JP (2) | JP3990453B2 (es) |
| KR (1) | KR100493843B1 (es) |
| CN (1) | CN1084728C (es) |
| AT (1) | ATE195508T1 (es) |
| AU (1) | AU700763B2 (es) |
| BG (1) | BG63298B1 (es) |
| BR (1) | BR9610677A (es) |
| CA (1) | CA2232607C (es) |
| CZ (1) | CZ298896B6 (es) |
| DE (1) | DE69609849T2 (es) |
| EA (1) | EA000529B1 (es) |
| ES (1) | ES2148791T3 (es) |
| HK (1) | HK1016578A1 (es) |
| HU (1) | HU225619B1 (es) |
| IL (2) | IL123610A (es) |
| MX (1) | MX9802226A (es) |
| NZ (1) | NZ318460A (es) |
| OA (1) | OA10675A (es) |
| PL (1) | PL190726B1 (es) |
| RO (1) | RO120540B1 (es) |
| SK (1) | SK283347B6 (es) |
| TR (1) | TR199800511T1 (es) |
| UA (1) | UA52617C2 (es) |
| WO (1) | WO1997011051A1 (es) |
| ZA (1) | ZA967921B (es) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3367847A (en) * | 1966-02-01 | 1968-02-06 | Du Pont | Purification of ethylene glycol containing salts of terephthalic acid by plural distiallation |
| US3637847A (en) * | 1969-09-03 | 1972-01-25 | Monsanto Co | N-haloalkyl-anilides |
| US5155272A (en) * | 1976-12-29 | 1992-10-13 | Monsanto Company | Process for the production of haloacylamides |
| HU177876B (en) * | 1979-04-24 | 1982-01-28 | Nitrokemia Ipartelepek | Process for preparing 2,6-dialkyl-n-/alkoxy-methyl/-chloro-acetanilide derivatives |
| DE2925263A1 (de) * | 1979-06-22 | 1981-01-08 | Basf Ag | Verfahren zur herstellung von aromatischen azomethinen |
| HU219568B (hu) * | 1991-04-04 | 2001-05-28 | Zeneca Ltd. | Eljárás formaldehiddel végzett kémiai reakciók lefolytatására és aromás azometin előállítására |
| DE4201605A1 (de) * | 1992-01-22 | 1993-07-29 | Bayer Ag | Verfahren zur herstellung von azomethinen |
-
1996
- 1996-09-19 RO RO98-00754A patent/RO120540B1/ro unknown
- 1996-09-19 US US08/719,298 patent/US5852215A/en not_active Expired - Lifetime
- 1996-09-19 AU AU69945/96A patent/AU700763B2/en not_active Expired
- 1996-09-19 AT AT96931148T patent/ATE195508T1/de active
- 1996-09-19 WO PCT/GB1996/002311 patent/WO1997011051A1/en active IP Right Grant
- 1996-09-19 IL IL12361096A patent/IL123610A/xx not_active IP Right Cessation
- 1996-09-19 MX MX9802226A patent/MX9802226A/es unknown
- 1996-09-19 JP JP51248097A patent/JP3990453B2/ja not_active Expired - Fee Related
- 1996-09-19 KR KR10-1998-0702105A patent/KR100493843B1/ko not_active IP Right Cessation
- 1996-09-19 DE DE69609849T patent/DE69609849T2/de not_active Expired - Lifetime
- 1996-09-19 EA EA199800213A patent/EA000529B1/ru not_active IP Right Cessation
- 1996-09-19 CA CA002232607A patent/CA2232607C/en not_active Expired - Lifetime
- 1996-09-19 CZ CZ0082998A patent/CZ298896B6/cs not_active IP Right Cessation
- 1996-09-19 TR TR1998/00511T patent/TR199800511T1/xx unknown
- 1996-09-19 BR BR9610677A patent/BR9610677A/pt not_active IP Right Cessation
- 1996-09-19 NZ NZ318460A patent/NZ318460A/xx not_active IP Right Cessation
- 1996-09-19 ZA ZA967921A patent/ZA967921B/xx unknown
- 1996-09-19 PL PL96325553A patent/PL190726B1/pl unknown
- 1996-09-19 EP EP96931148A patent/EP0853611B1/en not_active Expired - Lifetime
- 1996-09-19 HU HU9900171A patent/HU225619B1/hu unknown
- 1996-09-19 CN CN96197103A patent/CN1084728C/zh not_active Expired - Lifetime
- 1996-09-19 ES ES96931148T patent/ES2148791T3/es not_active Expired - Lifetime
- 1996-09-19 UA UA98031423A patent/UA52617C2/uk unknown
- 1996-09-19 SK SK373-98A patent/SK283347B6/sk not_active IP Right Cessation
-
1998
- 1998-03-17 BG BG102333A patent/BG63298B1/bg unknown
- 1998-03-20 OA OA9800033A patent/OA10675A/en unknown
-
1999
- 1999-04-21 HK HK99101737A patent/HK1016578A1/xx not_active IP Right Cessation
-
2002
- 2002-09-18 IL IL15179502A patent/IL151795A0/xx unknown
-
2006
- 2006-12-18 JP JP2006340607A patent/JP2007106773A/ja not_active Withdrawn
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