DD145529A5 - Reinigungsverfahren fuer cycloalkanon enthaltenden gemischen - Google Patents

Reinigungsverfahren fuer cycloalkanon enthaltenden gemischen Download PDF

Info

Publication number: DD145529A5
Authority: DD; German Democratic Republic
Prior art keywords: cycloalkanone; item; items; acid; aldehydes
Prior art date: 1978-08-12

Application number

DD79214917A

Other languages

German (de)

English (en)

Inventor

Otto G Plantema

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.)

1978-08-12

Filing date

1979-08-10

Publication date

1980-12-17

1979-08-10 Application filed by Stamicarbon filed Critical Stamicarbon

1980-12-17 Publication of DD145529A5 publication Critical patent/DD145529A5/de

Links

238000000034 method Methods 0.000 title claims description 23
239000000203 mixture Substances 0.000 title claims description 16
238000004140 cleaning Methods 0.000 title 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
150000001299 aldehydes Chemical class 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
238000005882 aldol condensation reaction Methods 0.000 claims description 14
238000004821 distillation Methods 0.000 claims description 13
150000001924 cycloalkanes Chemical class 0.000 claims description 11
238000007254 oxidation reaction Methods 0.000 claims description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
239000007864 aqueous solution Substances 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
230000003647 oxidation Effects 0.000 claims description 9
239000000243 solution Substances 0.000 claims description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
239000007791 liquid phase Substances 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
-1 cycloalkyl ester Chemical class 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
150000002500 ions Chemical class 0.000 claims description 5
229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
239000007859 condensation product Substances 0.000 claims description 2
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
239000003377 acid catalyst Substances 0.000 claims 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
238000009833 condensation Methods 0.000 description 7
238000005406 washing Methods 0.000 description 7
238000009835 boiling 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
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
229910001882 dioxygen Inorganic materials 0.000 description 5
239000007789 gas Substances 0.000 description 5
238000006386 neutralization reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 3
239000003518 caustics Substances 0.000 description 3
238000006356 dehydrogenation reaction Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
239000012074 organic phase Substances 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
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 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
239000002585 base Substances 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
239000003637 basic solution Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000001030 gas--liquid chromatography Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
238000000926 separation method Methods 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
239000012808 vapor phase Substances 0.000 description 2
TYDSIOSLHQWFOU-UHFFFAOYSA-N 2-cyclohexylidenecyclohexan-1-one Chemical compound O=C1CCCCC1=C1CCCCC1 TYDSIOSLHQWFOU-UHFFFAOYSA-N 0.000 description 1
238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
150000007513 acids 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
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000005494 condensation Effects 0.000 description 1
GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
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 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 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
239000012535 impurity Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 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
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000010626 work up procedure Methods 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)

DD79214917A 1978-08-12 1979-08-10 Reinigungsverfahren fuer cycloalkanon enthaltenden gemischen DD145529A5 (de)

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
DD145529A5 true DD145529A5 (de)	1980-12-17

Family

ID=19831369

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79214917A DD145529A5 (de)	1978-08-12	1979-08-10	Reinigungsverfahren fuer cycloalkanon enthaltenden gemischen

Country Status (17)

Country	Link
JP (1)	JPS5527192A (cs)
AR (1)	AR223010A1 (cs)
BE (1)	BE878200A (cs)
BR (1)	BR7905172A (cs)
CA (1)	CA1123457A (cs)
CS (1)	CS209931B2 (cs)
DD (1)	DD145529A5 (cs)
DE (1)	DE2932361A1 (cs)
ES (1)	ES483153A1 (cs)
FR (1)	FR2433012A1 (cs)
GB (1)	GB2028329B (cs)
IN (1)	IN152254B (cs)
IT (1)	IT1120507B (cs)
MX (1)	MX5997E (cs)
MY (1)	MY8500894A (cs)
NL (1)	NL7808416A (cs)
PL (1)	PL117395B1 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 (cs) *	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 AR AR277658A patent/AR223010A1/es active
- 1979-08-09 JP JP10177679A patent/JPS5527192A/ja active Pending
- 1979-08-09 DE DE19792932361 patent/DE2932361A1/de not_active Ceased
- 1979-08-10 FR FR7920505A patent/FR2433012A1/fr active Granted
- 1979-08-10 DD DD79214917A patent/DD145529A5/de unknown
- 1979-08-10 BR BR7905172A patent/BR7905172A/pt unknown
- 1979-08-10 IT IT50026/79A patent/IT1120507B/it active
- 1979-08-10 MX MX798311U patent/MX5997E/es unknown
- 1979-08-10 IN IN830/CAL/79A patent/IN152254B/en unknown
- 1979-08-10 BE BE0/196697A patent/BE878200A/nl not_active IP Right Cessation
- 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
IN152254B (cs)	1983-11-26
MY8500894A (en)	1985-12-31
DE2932361A1 (de)	1980-02-28
GB2028329A (en)	1980-03-05
MX5997E (es)	1984-09-18
CA1123457A (en)	1982-05-11
BE878200A (nl)	1980-02-11
IT7950026A0 (it)	1979-08-10
ES483153A1 (es)	1980-03-01
JPS5527192A (en)	1980-02-27
PL117395B1 (en)	1981-07-31
PL217702A1 (cs)	1980-04-08
CS209931B2 (en)	1981-12-31
BR7905172A (pt)	1980-05-06
AR223010A1 (es)	1981-07-15
FR2433012A1 (fr)	1980-03-07
GB2028329B (en)	1982-09-15
IT1120507B (it)	1986-03-26
NL7808416A (nl)	1980-02-14
FR2433012B1 (cs)	1982-12-10

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