CA1123457A - Process for the purification of cycloalkanone mixtures obtained in the oxidation of cycloalkanes - Google Patents

Process for the purification of cycloalkanone mixtures obtained in the oxidation of cycloalkanes

Info

Publication number: CA1123457A
Authority: CA; Canada
Prior art keywords: cycloalkanone; reaction; reaction mixture; process according; carbon atoms
Prior art date: 1978-08-12
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

Application number

CA332,513A

Other languages

English (en)

French (fr)

Inventor

Otto G. Plantema

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Stamicarbon BV

Original Assignee

Stamicarbon BV

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

1979-07-25

Publication date

1982-05-11

1979-07-25 Application filed by Stamicarbon BV filed Critical Stamicarbon BV

1982-05-11 Application granted granted Critical

1982-05-11 Publication of CA1123457A publication Critical patent/CA1123457A/en

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 17
238000007254 oxidation reaction Methods 0.000 title claims abstract description 15
150000001924 cycloalkanes Chemical class 0.000 title claims abstract description 14
230000003647 oxidation Effects 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims description 23
238000000746 purification Methods 0.000 title description 5
150000001299 aldehydes Chemical class 0.000 claims abstract description 33
238000005882 aldol condensation reaction Methods 0.000 claims abstract description 27
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 9
239000007791 liquid phase Substances 0.000 claims abstract description 9
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 8
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
239000011541 reaction mixture Substances 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 15
238000004821 distillation Methods 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
239000000243 solution Substances 0.000 claims description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
239000007864 aqueous solution Substances 0.000 claims description 9
238000009835 boiling Methods 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
239000007859 condensation product Substances 0.000 claims description 6
239000012458 free base Substances 0.000 claims description 6
239000003377 acid catalyst Substances 0.000 claims description 5
150000002500 ions Chemical class 0.000 claims description 5
239000012044 organic layer Substances 0.000 claims description 5
229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
239000000463 material Substances 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
239000001117 sulphuric acid Substances 0.000 claims description 3
235000011149 sulphuric acid Nutrition 0.000 claims description 3
239000002585 base Substances 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
239000012670 alkaline solution Substances 0.000 claims 3
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 1
230000001747 exhibiting effect Effects 0.000 abstract 1
238000005406 washing Methods 0.000 description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
238000009833 condensation Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
229940083608 sodium hydroxide Drugs 0.000 description 6
238000006386 neutralization reaction Methods 0.000 description 5
229920002292 Nylon 6 Polymers 0.000 description 4
239000003513 alkali Substances 0.000 description 4
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
229940001593 sodium carbonate Drugs 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000006356 dehydrogenation reaction Methods 0.000 description 3
238000002474 experimental method Methods 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
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
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 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
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
-1 cycloalkyl ester Chemical class 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
238000010992 reflux Methods 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
244000228957 Ferula foetida 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
235000014676 Phragmites communis Nutrition 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 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
238000010586 diagram Methods 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
150000004679 hydroxides Chemical class 0.000 description 1
238000007689 inspection Methods 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000006146 oximation reaction Methods 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
230000008707 rearrangement Effects 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 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)

CA332,513A 1978-08-12 1979-07-25 Process for the purification of cycloalkanone mixtures obtained in the oxidation of cycloalkanes Expired CA1123457A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL7808416		1978-08-12
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
CA1123457A true CA1123457A (en)	1982-05-11

Family

ID=19831369

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA332,513A Expired CA1123457A (en)	1978-08-12	1979-07-25	Process for the purification of cycloalkanone mixtures obtained in the oxidation of cycloalkanes

Country Status (17)

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

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1433774A1 (de)	2002-12-27	2004-06-30	Koninklijke DSM N.V.	Verfahren zur Reduzierung der Aldehydkonzentration in einer Cyclohexanon- und eine oder mehrere Aldehyd enthaltende Mischung
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 (de) *	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 DE DE19792932361 patent/DE2932361A1/de not_active Ceased
- 1979-08-09 JP JP10177679A patent/JPS5527192A/ja active Pending
- 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
- 1979-08-10 IT IT50026/79A patent/IT1120507B/it active
- 1979-08-10 MX MX798311U patent/MX5997E/es unknown
- 1979-08-10 BR BR7905172A patent/BR7905172A/pt unknown
- 1979-08-10 DD DD79214917A patent/DD145529A5/de unknown
- 1979-08-10 FR FR7920505A patent/FR2433012A1/fr active Granted
- 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
DE2932361A1 (de)	1980-02-28
NL7808416A (nl)	1980-02-14
AR223010A1 (es)	1981-07-15
IT1120507B (it)	1986-03-26
FR2433012A1 (fr)	1980-03-07
PL117395B1 (en)	1981-07-31
DD145529A5 (de)	1980-12-17
IT7950026A0 (it)	1979-08-10
MX5997E (es)	1984-09-18
PL217702A1 (de)	1980-04-08
JPS5527192A (en)	1980-02-27
CS209931B2 (en)	1981-12-31
GB2028329A (en)	1980-03-05
GB2028329B (en)	1982-09-15
FR2433012B1 (de)	1982-12-10
BE878200A (nl)	1980-02-11
MY8500894A (en)	1985-12-31
BR7905172A (pt)	1980-05-06
IN152254B (de)	1983-11-26
ES483153A1 (es)	1980-03-01

Legal Events

Date	Code	Title	Description
1999-05-11	MKEX	Expiry

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CA1123457A (en)	1982-05-11	Process for the purification of cycloalkanone mixtures obtained in the oxidation of cycloalkanes
NL7905781A (nl)	1981-01-28	Werkwijze voor het bereiden van cyclohexanol.
CA1236486A (en)	1988-05-10	Continuous process for producing 1,2-pentanediol
EP0030109B1 (de)	1983-10-05	Verfahren zur Herstellung von Isopren
EP0392579B1 (de)	1994-07-13	Aldolkondensation
JPH08503713A (ja)	1996-04-23	イソホロンプロセス
US3972951A (en)	1976-08-03	Process for the formation of 2,6-diphenyl-phenol
US3236869A (en)	1966-02-22	Allenic acids
US3359335A (en)	1967-12-19	Caustic scrubbing of aldox alcohols
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RU2760548C1 (ru)	2021-11-29	Способ получения циклогексанона
JPH05977A (ja)	1993-01-08	シクロドデカノール及びシクロドデカノン混合物の精製法
JP3563105B2 (ja)	2004-09-08	γ，δ−不飽和アルコールの製造方法
CN101128411B (zh)	2010-12-29	酚类的精制方法
KR830001083B1 (ko)	1983-06-02	사이클로알칸(cycloalkanes)의 산화로 얻어진 사이클로 알카논(cycloalkanone) 혼합물의 정제방법
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US2010076A (en)	1935-08-06	Process for the treatment of unsaturated alcohols
JPS5899434A (ja)	1983-06-13	メタクリル酸の精製方法
JP3285439B2 (ja)	2002-05-27	反応粗液の製造法および１，３−ブチレングリコ−ルの製造法
US4001342A (en)	1977-01-04	Production of ethylphenols