CH401954A - Verfahren zur Herstellung von Cyclohexanon und Cyclohexanol - Google Patents

Verfahren zur Herstellung von Cyclohexanon und Cyclohexanol

Info

Publication number: CH401954A
Authority: CH; Switzerland
Prior art keywords: cyclohexanone; cyclohexanol; solution; hydroxide; sep
Prior art date: 1959-01-26

Application number

CH77760A

Other languages

German (de)

English (en)

Inventor

Marie Steeman Johann Wilhelmus

Original Assignee

Stamicarbon

Priority date (The priority date 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 date listed.)

1959-01-26

Filing date

1960-01-25

Publication date

1965-11-15

1960-01-25 Application filed by Stamicarbon filed Critical Stamicarbon

1965-11-15 Publication of CH401954A publication Critical patent/CH401954A/de

Links

JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 32
238000000034 method Methods 0.000 title claims description 16
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims description 13
238000004519 manufacturing process Methods 0.000 title claims description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 38
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 20
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 12
238000007254 oxidation reaction Methods 0.000 claims description 11
229910000029 sodium carbonate Inorganic materials 0.000 claims description 11
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
230000003647 oxidation Effects 0.000 claims description 10
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
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 claims description 6
239000000203 mixture Substances 0.000 claims description 6
238000001256 steam distillation Methods 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 5
239000001569 carbon dioxide Substances 0.000 claims description 5
229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
238000004821 distillation Methods 0.000 claims description 4
239000007789 gas Substances 0.000 claims description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
238000002485 combustion reaction Methods 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 19
150000002148 esters Chemical class 0.000 description 15
238000007127 saponification reaction Methods 0.000 description 14
239000000243 solution Substances 0.000 description 13
238000002474 experimental method Methods 0.000 description 6
235000017550 sodium carbonate Nutrition 0.000 description 5
150000007513 acids Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
BJZJDEOGMBZSLE-UHFFFAOYSA-N cyclohexane;hydrate Chemical compound O.C1CCCCC1 BJZJDEOGMBZSLE-UHFFFAOYSA-N 0.000 description 1
HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
PWVHLUKAENFZIA-UHFFFAOYSA-N cyclohexanol;cyclohexanone Chemical compound OC1CCCCC1.O=C1CCCCC1 PWVHLUKAENFZIA-UHFFFAOYSA-N 0.000 description 1
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002697 manganese compounds Chemical class 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH77760A 1959-01-26 1960-01-25 Verfahren zur Herstellung von Cyclohexanon und Cyclohexanol CH401954A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL235486		1959-01-26

Publications (1)

Publication Number	Publication Date
CH401954A true CH401954A (de)	1965-11-15

Family

ID=19751535

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH77760A CH401954A (de)	1959-01-26	1960-01-25	Verfahren zur Herstellung von Cyclohexanon und Cyclohexanol

Country Status (2)

Country	Link
BE (1)	BE586726A (fr)
CH (1)	CH401954A (fr)

1960
- 1960-01-19 BE BE586726A patent/BE586726A/fr unknown
- 1960-01-25 CH CH77760A patent/CH401954A/de unknown

Also Published As

Publication number	Publication date
BE586726A (fr)	1960-07-19

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