CA1051460A - Purification process for crude n-paraffinone oximes - Google Patents
Purification process for crude n-paraffinone oximesInfo
- Publication number
- CA1051460A CA1051460A CA236,422A CA236422A CA1051460A CA 1051460 A CA1051460 A CA 1051460A CA 236422 A CA236422 A CA 236422A CA 1051460 A CA1051460 A CA 1051460A
- Authority
- CA
- Canada
- Prior art keywords
- urea
- oxime
- crude
- oximes
- weight
- 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
- 150000002923 oximes Chemical class 0.000 title claims abstract description 154
- 238000000746 purification Methods 0.000 title abstract description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 100
- 238000000034 method Methods 0.000 claims abstract description 45
- 239000004202 carbamide Substances 0.000 claims abstract description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000000460 chlorine Substances 0.000 claims abstract description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 27
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- 150000002576 ketones Chemical class 0.000 claims description 67
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- 239000012535 impurity Substances 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- 230000009935 nitrosation Effects 0.000 claims description 12
- 238000007034 nitrosation reaction Methods 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 5
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 9
- 239000000356 contaminant Substances 0.000 abstract description 7
- 238000001914 filtration Methods 0.000 abstract description 5
- 238000005292 vacuum distillation Methods 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 18
- 238000004821 distillation Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000009918 complex formation Effects 0.000 description 5
- 238000000199 molecular distillation Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000004157 Nitrosyl chloride Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- HRGRUCGUHMULFW-UHFFFAOYSA-N n-undecan-6-ylidenehydroxylamine Chemical compound CCCCCC(=NO)CCCCC HRGRUCGUHMULFW-UHFFFAOYSA-N 0.000 description 3
- 235000019392 nitrosyl chloride Nutrition 0.000 description 3
- -1 octanone oximes Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- VFFLQUNAMYWTLJ-UHFFFAOYSA-N carbamoyl isocyanate Chemical compound NC(=O)N=C=O VFFLQUNAMYWTLJ-UHFFFAOYSA-N 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000004045 organic chlorine compounds Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Natural products CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- VKCYHJWLYTUGCC-UHFFFAOYSA-N heptyl methyl ketone Natural products CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- NGTGENGUUCHSLQ-UHFFFAOYSA-N n-heptan-2-ylidenehydroxylamine Chemical class CCCCCC(C)=NO NGTGENGUUCHSLQ-UHFFFAOYSA-N 0.000 description 1
- WHXCGIRATPOBAY-UHFFFAOYSA-N n-hexan-2-ylidenehydroxylamine Chemical class CCCCC(C)=NO WHXCGIRATPOBAY-UHFFFAOYSA-N 0.000 description 1
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N n-hexyl methyl ketone Natural products CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000011176 pooling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000003245 working effect Effects 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
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/14—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/524,109 US3960955A (en) | 1974-11-15 | 1974-11-15 | Purification process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051460A true CA1051460A (en) | 1979-03-27 |
Family
ID=24087796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA236,422A Expired CA1051460A (en) | 1974-11-15 | 1975-09-25 | Purification process for crude n-paraffinone oximes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3960955A (enExample) |
| JP (1) | JPS5170711A (enExample) |
| BE (1) | BE835326A (enExample) |
| CA (1) | CA1051460A (enExample) |
| DE (1) | DE2547461A1 (enExample) |
| FR (1) | FR2291188A1 (enExample) |
| GB (1) | GB1477081A (enExample) |
| IT (1) | IT1049482B (enExample) |
| NL (1) | NL7513110A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111655830A (zh) | 2018-01-26 | 2020-09-11 | 埃科莱布美国股份有限公司 | 固化液体阴离子表面活性剂 |
| AU2019211453B2 (en) | 2018-01-26 | 2021-10-14 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier |
| US11214763B2 (en) | 2018-01-26 | 2022-01-04 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681334A (en) * | 1954-06-15 | Formation of urea complexes with | ||
| US2569985A (en) * | 1948-02-16 | 1951-10-02 | Shell Dev | Thiourea-ketone complexes |
| GB1180393A (en) * | 1966-03-08 | 1970-02-04 | Nat Res Dev | Improvements in the Manufacture of Urea |
| US3316236A (en) * | 1966-05-23 | 1967-04-25 | Continental Oil Co | Separation of amine oxides by urea adduct formation |
| US3717623A (en) * | 1970-04-22 | 1973-02-20 | Merck & Co Inc | Sulfanilyl phenyl urea complexes useful against marek's disease |
-
1974
- 1974-11-15 US US05/524,109 patent/US3960955A/en not_active Expired - Lifetime
-
1975
- 1975-09-25 CA CA236,422A patent/CA1051460A/en not_active Expired
- 1975-10-08 GB GB4113875A patent/GB1477081A/en not_active Expired
- 1975-10-12 JP JP50135248A patent/JPS5170711A/ja active Pending
- 1975-10-23 DE DE19752547461 patent/DE2547461A1/de active Pending
- 1975-10-31 FR FR7533344A patent/FR2291188A1/fr active Granted
- 1975-11-06 BE BE161653A patent/BE835326A/xx unknown
- 1975-11-10 NL NL7513110A patent/NL7513110A/xx not_active Application Discontinuation
- 1975-11-14 IT IT29324/75A patent/IT1049482B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2291188B1 (enExample) | 1980-04-04 |
| GB1477081A (en) | 1977-06-22 |
| BE835326A (fr) | 1976-05-06 |
| JPS5170711A (enExample) | 1976-06-18 |
| DE2547461A1 (de) | 1976-05-20 |
| IT1049482B (it) | 1981-01-20 |
| NL7513110A (nl) | 1976-05-18 |
| FR2291188A1 (fr) | 1976-06-11 |
| US3960955A (en) | 1976-06-01 |
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