CS209931B2 - Method of cleaning the mixtures containing the cyclohexanon - Google Patents
Method of cleaning the mixtures containing the cyclohexanon Download PDFInfo
- Publication number
- CS209931B2 CS209931B2 CS795441A CS544179A CS209931B2 CS 209931 B2 CS209931 B2 CS 209931B2 CS 795441 A CS795441 A CS 795441A CS 544179 A CS544179 A CS 544179A CS 209931 B2 CS209931 B2 CS 209931B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- cyclohexanone
- aldol condensation
- acid
- aldehydes
- temperature
- Prior art date
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 60
- 238000000034 method Methods 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 title claims description 20
- 238000004140 cleaning Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- 238000005882 aldol condensation reaction Methods 0.000 claims abstract description 23
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 7
- 239000003377 acid catalyst Substances 0.000 claims abstract description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 6
- 238000000746 purification Methods 0.000 claims abstract description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- OHYPPUOVSUINHM-UHFFFAOYSA-N 4-(methylamino)phenol;sulfuric acid Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1 OHYPPUOVSUINHM-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 238000004821 distillation Methods 0.000 abstract description 14
- 238000007254 oxidation reaction Methods 0.000 abstract description 9
- 230000003647 oxidation Effects 0.000 abstract description 8
- 150000001924 cycloalkanes Chemical class 0.000 abstract description 7
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 5
- 229920002292 Nylon 6 Polymers 0.000 description 5
- 229910001882 dioxygen Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000002243 cyclohexanonyl group Chemical class *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000005201 scrubbing Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 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
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- TYDSIOSLHQWFOU-UHFFFAOYSA-N 2-cyclohexylidenecyclohexan-1-one Chemical compound O=C1CCCCC1=C1CCCCC1 TYDSIOSLHQWFOU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- -1 cyclohexyl- Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010518 undesired secondary reaction Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7808416A NL7808416A (nl) | 1978-08-12 | 1978-08-12 | Werkwijze voor het verwijderen van aldehyden uit cyclo- alkanon bevattende mengsels verkregen bij oxidatie van cycloalkanen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209931B2 true CS209931B2 (en) | 1981-12-31 |
Family
ID=19831369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS795441A CS209931B2 (en) | 1978-08-12 | 1979-08-08 | Method of cleaning the mixtures containing the cyclohexanon |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5527192A (es) |
| AR (1) | AR223010A1 (es) |
| BE (1) | BE878200A (es) |
| BR (1) | BR7905172A (es) |
| CA (1) | CA1123457A (es) |
| CS (1) | CS209931B2 (es) |
| DD (1) | DD145529A5 (es) |
| DE (1) | DE2932361A1 (es) |
| ES (1) | ES483153A1 (es) |
| FR (1) | FR2433012A1 (es) |
| GB (1) | GB2028329B (es) |
| IN (1) | IN152254B (es) |
| IT (1) | IT1120507B (es) |
| MX (1) | MX5997E (es) |
| MY (1) | MY8500894A (es) |
| NL (1) | NL7808416A (es) |
| PL (1) | PL117395B1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1433774A1 (en) | 2002-12-27 | 2004-06-30 | Koninklijke DSM N.V. | Process for reducing the aldehyde concentration in a mixture comprising cyclohexanone and one or more aldehydes |
| US20060189829A1 (en) | 2005-02-18 | 2006-08-24 | Basf Corporation | Method of minimizing aldehyde based impurities in a process stream |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1085529B (de) * | 1952-07-03 | 1960-07-21 | American Home Prod | Verfahren zur Herstellung von 4-Aryl-4-carbalkoxy-N-alkyl-azacycloalkanen und deren Salzen |
| DE1046610B (de) * | 1955-06-15 | 1958-12-18 | Basf Ag | Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon durch Oxydation von Cyclohexan |
| DE1085520B (de) * | 1958-01-25 | 1960-07-21 | Basf Ag | Verfahren zur Herstellung von Alkylen-bis-cycloalkanonen |
| DE1155121B (de) * | 1960-05-06 | 1963-10-03 | Basf Ag | Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon durch Oxydation von Cyclohexan |
| DE1518255B1 (de) * | 1965-01-30 | 1969-12-11 | Vickers Zimmer Ag | Verfahren zur Aufarbeitung des Reaktionsgemisches der Oxydation von Cyclohexan mit sauerstoffhaltigen Gasen in fluessiger Phase |
| DE2246103A1 (de) * | 1972-09-20 | 1974-03-28 | Bayer Sa Nv | Verfahren zur reinigung von cyclohexanon |
| JPS4969634A (es) * | 1973-09-20 | 1974-07-05 | ||
| US3987100A (en) * | 1974-04-11 | 1976-10-19 | E. I. Du Pont De Nemours And Company | Cyclohexane oxidation in the presence of binary catalysts |
| DE2650892C3 (de) * | 1976-11-06 | 1980-05-29 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Aufarbeitung von Cyclohexanol und Cyclohexanon enthaltenden Reaktionsgemischen |
-
1978
- 1978-08-12 NL NL7808416A patent/NL7808416A/nl not_active Application Discontinuation
-
1979
- 1979-07-25 CA CA332,513A patent/CA1123457A/en not_active Expired
- 1979-08-06 ES ES483153A patent/ES483153A1/es not_active Expired
- 1979-08-08 CS CS795441A patent/CS209931B2/cs unknown
- 1979-08-09 JP JP10177679A patent/JPS5527192A/ja active Pending
- 1979-08-09 AR AR277658A patent/AR223010A1/es active
- 1979-08-09 DE DE19792932361 patent/DE2932361A1/de not_active Ceased
- 1979-08-10 BE BE0/196697A patent/BE878200A/nl not_active IP Right Cessation
- 1979-08-10 BR BR7905172A patent/BR7905172A/pt unknown
- 1979-08-10 MX MX798311U patent/MX5997E/es unknown
- 1979-08-10 DD DD79214917A patent/DD145529A5/de unknown
- 1979-08-10 FR FR7920505A patent/FR2433012A1/fr active Granted
- 1979-08-10 IN IN830/CAL/79A patent/IN152254B/en unknown
- 1979-08-10 IT IT50026/79A patent/IT1120507B/it active
- 1979-08-11 PL PL1979217702A patent/PL117395B1/pl unknown
- 1979-08-13 GB GB7928080A patent/GB2028329B/en not_active Expired
-
1985
- 1985-12-30 MY MY894/85A patent/MY8500894A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2028329A (en) | 1980-03-05 |
| MX5997E (es) | 1984-09-18 |
| AR223010A1 (es) | 1981-07-15 |
| MY8500894A (en) | 1985-12-31 |
| BE878200A (nl) | 1980-02-11 |
| DD145529A5 (de) | 1980-12-17 |
| PL217702A1 (es) | 1980-04-08 |
| JPS5527192A (en) | 1980-02-27 |
| CA1123457A (en) | 1982-05-11 |
| GB2028329B (en) | 1982-09-15 |
| FR2433012B1 (es) | 1982-12-10 |
| ES483153A1 (es) | 1980-03-01 |
| PL117395B1 (en) | 1981-07-31 |
| FR2433012A1 (fr) | 1980-03-07 |
| IT7950026A0 (it) | 1979-08-10 |
| IN152254B (es) | 1983-11-26 |
| BR7905172A (pt) | 1980-05-06 |
| IT1120507B (it) | 1986-03-26 |
| DE2932361A1 (de) | 1980-02-28 |
| NL7808416A (nl) | 1980-02-14 |
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