DE2144971A1 - - Google Patents
Info
- Publication number
- DE2144971A1 DE2144971A1 DE19712144971 DE2144971A DE2144971A1 DE 2144971 A1 DE2144971 A1 DE 2144971A1 DE 19712144971 DE19712144971 DE 19712144971 DE 2144971 A DE2144971 A DE 2144971A DE 2144971 A1 DE2144971 A1 DE 2144971A1
- Authority
- DE
- Germany
- Prior art keywords
- ketone
- chlorination
- alpha
- carried out
- chloroketone
- 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
- 238000005660 chlorination reaction Methods 0.000 claims description 21
- 150000002576 ketones Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 14
- 238000006460 hydrolysis reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 150000003997 cyclic ketones Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- ODZTXUXIYGJLMC-UHFFFAOYSA-N 2-hydroxycyclohexan-1-one Chemical compound OC1CCCCC1=O ODZTXUXIYGJLMC-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JAODHAABODLKEG-UHFFFAOYSA-N 2,2-dimethyloctan-4-one Chemical compound CCCCC(=O)CC(C)(C)C JAODHAABODLKEG-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- -1 Cyclic hydroxy ketones Chemical class 0.000 description 1
- 241000551547 Dione <red algae> Species 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
- 239000004677 Nylon Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003998 acyclic ketones Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SXOZDDAFVJANJP-UHFFFAOYSA-N cyclodecanone Chemical compound O=C1CCCCCCCCC1 SXOZDDAFVJANJP-UHFFFAOYSA-N 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7047970A | 1970-09-08 | 1970-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2144971A1 true DE2144971A1 (enrdf_load_stackoverflow) | 1972-03-16 |
Family
ID=22095542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712144971 Pending DE2144971A1 (enrdf_load_stackoverflow) | 1970-09-08 | 1971-09-08 |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE772233A (enrdf_load_stackoverflow) |
| CA (1) | CA948213A (enrdf_load_stackoverflow) |
| DE (1) | DE2144971A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2107245A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1320633A (enrdf_load_stackoverflow) |
| IT (1) | IT945859B (enrdf_load_stackoverflow) |
| LU (1) | LU63852A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7112112A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG71201A1 (en) * | 1998-04-20 | 2000-03-21 | Givaudan Roure Int | Hydroxa-methyl-hexanones |
-
1971
- 1971-08-27 CA CA121,555A patent/CA948213A/en not_active Expired
- 1971-09-01 IT IT6990771A patent/IT945859B/it active
- 1971-09-03 GB GB4121171A patent/GB1320633A/en not_active Expired
- 1971-09-03 FR FR7131954A patent/FR2107245A5/fr not_active Expired
- 1971-09-03 NL NL7112112A patent/NL7112112A/xx unknown
- 1971-09-06 LU LU63852D patent/LU63852A1/xx unknown
- 1971-09-06 BE BE772233A patent/BE772233A/xx unknown
- 1971-09-08 DE DE19712144971 patent/DE2144971A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT945859B (it) | 1973-05-10 |
| BE772233A (fr) | 1972-03-06 |
| NL7112112A (enrdf_load_stackoverflow) | 1972-03-10 |
| LU63852A1 (enrdf_load_stackoverflow) | 1973-03-09 |
| CA948213A (en) | 1974-05-28 |
| FR2107245A5 (enrdf_load_stackoverflow) | 1972-05-05 |
| GB1320633A (en) | 1973-06-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0026291B1 (de) | Verfahren zur Herstellung von Terephthalaldehyd bzw. Isophthalaldehyd | |
| DE2527289A1 (de) | Verfahren zur herstellung von alkylacetophenonen | |
| DE2144971A1 (enrdf_load_stackoverflow) | ||
| DE1203760B (de) | Verfahren zur Herstellung von Sorbinsaeure-alkylestern | |
| DE69511384T2 (de) | Verbessertes verfahren zur herstellung von beta-diketonen | |
| DE1668730A1 (de) | Verfahren zur Herstellung von alpha-o-disubstituierten Alkanen | |
| DE2163539B2 (de) | Herstellung von Epsilon-Caprolactam und O-Acetylcyclohexanonoxlm | |
| DE69017864T2 (de) | Verfahren zur Herstellung von Phenol. | |
| DE1643402C3 (de) | Verfahren zur Herstellung von 2,6-Diphenylphenol | |
| DE2443341A1 (de) | Verfahren zur reinigung von caprolactam | |
| DE739259C (de) | Verfahren zur Umlagerung von cyclischen Ketoximen in Lactame | |
| DE1808389C3 (de) | Verfahren zur Herstellung von Resorcin durch Säurehydrolyse von m-Phenylendiamin | |
| DE2804597A1 (de) | Verfahren zur herstellung von beta-damascon und beta-damascenon | |
| DE2609566C3 (de) | Verfahren zur Herstellung von Methylheptenon | |
| DE898737C (de) | Verfahren zur Herstellung von Chlormethylmethylaether | |
| DE840695C (de) | Verfahren zur Herstellung von 1, 1, 3-Trimethylcyclohexanon-5 | |
| DE3325976C2 (enrdf_load_stackoverflow) | ||
| DD145096A1 (de) | Verfahren zur herstellung von isophoron | |
| DE2426863A1 (de) | Verfahren zur spaltung von cycloaliphatischen hdroperoxiden | |
| DE2145308C3 (de) | Verfahren zur Herstellung von 4-(4-Hydroxyphenyl)-butan-2-on | |
| DE1643985C3 (de) | S-lsopropyl^nitro-phenyl-dimethyl-carbinol und 3,5-Diisopropyl-4-nitro-phenyldimethylcarbinol und Verfahren zu deren Herstellung | |
| DE1518970C3 (de) | Verfahren zur Herstellung von gesättigten aliphatischen Dicarbonsäuren | |
| DE1793441A1 (de) | Verfahren zur Herstellung von Sorbinsaeure | |
| DE854211C (de) | Verfahren zur Herstellung klopffester Treibstoffe | |
| DE1643249C3 (de) | Verfahren zur kontinuierlichen Herstellung von Diamino-di-tolymethanen |