CH422767A - Verfahren zur Herstellung eines Gemisches, welches ein cyclisches aliphatisches Keton, eine ungesättigte cyclische aliphatische Carbonsäure und ein cyclisches Olefin enthält, aus einer Cycloalkanmonocarbonsäure - Google Patents

Verfahren zur Herstellung eines Gemisches, welches ein cyclisches aliphatisches Keton, eine ungesättigte cyclische aliphatische Carbonsäure und ein cyclisches Olefin enthält, aus einer Cycloalkanmonocarbonsäure

Info

Publication number: CH422767A
Authority: CH; Switzerland
Prior art keywords: acid; cyclic aliphatic; reaction; cyclic; carboxylic acid
Prior art date: 1960-08-04

Application number

CH913261A

Other languages

German (de)

English (en)

Inventor

Albert Bigot Johan

Laurens Kerkhoffs Pieter

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.)

1960-08-04

Filing date

1961-08-03

Publication date

1966-10-31

1961-08-03 Application filed by Stamicarbon filed Critical Stamicarbon

1966-10-31 Publication of CH422767A publication Critical patent/CH422767A/de

Links

-1 unsaturated cyclic aliphatic carboxylic acid Chemical class 0.000 title claims description 18
239000000203 mixture Substances 0.000 title claims description 14
125000004122 cyclic group Chemical group 0.000 title claims description 4
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 title claims description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title description 2
239000002253 acid Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 9
150000002736 metal compounds Chemical class 0.000 claims description 5
239000007791 liquid phase Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
229910001882 dioxygen Inorganic materials 0.000 claims description 2
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 25
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 20
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 17
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 16
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
238000004821 distillation Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000009835 boiling Methods 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
239000006227 byproduct Substances 0.000 description 7
FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 7
159000000003 magnesium salts Chemical class 0.000 description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
230000035484 reaction time Effects 0.000 description 6
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000000395 magnesium oxide Chemical class 0.000 description 4
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical class [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
239000000155 melt Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
239000005711 Benzoic acid Substances 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
229960004643 cupric oxide Drugs 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical class [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012295 chemical reaction liquid Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000005749 Copper compound Substances 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000004416 zinc carbonate Nutrition 0.000 description 1
239000011667 zinc carbonate Substances 0.000 description 1
229910000010 zinc carbonate Inorganic materials 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/207—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds
- C07C1/2078—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms from carbonyl compounds by a transformation in which at least one -C(=O)-O- moiety is eliminated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/72—Copper
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
- Y02P20/129—Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH913261A 1960-08-04 1961-08-03 Verfahren zur Herstellung eines Gemisches, welches ein cyclisches aliphatisches Keton, eine ungesättigte cyclische aliphatische Carbonsäure und ein cyclisches Olefin enthält, aus einer Cycloalkanmonocarbonsäure CH422767A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL254566		1960-08-04
NL264222		1961-04-28

Publications (1)

Publication Number	Publication Date
CH422767A true CH422767A (de)	1966-10-31

Family

ID=26641728

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH913261A CH422767A (de)	1960-08-04	1961-08-03	Verfahren zur Herstellung eines Gemisches, welches ein cyclisches aliphatisches Keton, eine ungesättigte cyclische aliphatische Carbonsäure und ein cyclisches Olefin enthält, aus einer Cycloalkanmonocarbonsäure

Country Status (4)

Country	Link
BE (1)	BE606883A (fr)
CH (1)	CH422767A (fr)
ES (1)	ES269544A1 (fr)
GB (1)	GB964980A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6401389A (fr) *	1964-02-17	1965-08-18
US4393260A (en)	1980-08-01	1983-07-12	The Standard Oil Company	Preparation of cyclohexenyl compounds

1961
- 1961-07-28 GB GB27549/61A patent/GB964980A/en not_active Expired
- 1961-08-03 ES ES0269544A patent/ES269544A1/es not_active Expired
- 1961-08-03 CH CH913261A patent/CH422767A/de unknown
- 1961-08-03 BE BE606883A patent/BE606883A/fr unknown

Also Published As

Publication number	Publication date
ES269544A1 (es)	1962-01-01
BE606883A (fr)	1962-02-05
GB964980A (en)	1964-07-29

Publication	Publication Date	Title
DE882987C (de)	1953-07-13	Verfahren zur Herstellung von tert.-Alkylbenzolcarbonsaeuren
DE2600541C3 (de)	1978-06-08	Verfahren zur Herstellung von Phenylbrenztraubensäure oder Arylbrenztraubensäuren
DE69606128T2 (de)	2000-08-31	Verfahren zur Zersetzung von Cycloalkylhydroperoxid
CH422767A (de)	1966-10-31	Verfahren zur Herstellung eines Gemisches, welches ein cyclisches aliphatisches Keton, eine ungesättigte cyclische aliphatische Carbonsäure und ein cyclisches Olefin enthält, aus einer Cycloalkanmonocarbonsäure
DE2758391C2 (fr)	1988-05-05
DE947162C (de)	1956-09-06	Verfahren zur Aufarbeitung des bei der Nitrierung von Cyclohexan anfallenden Reaktionsgemisches
DE2163031B2 (de)	1976-12-30	Verfahren zur herstellung von terephthalsaeuredimethylester
DE1238000B (de)	1967-04-06	Verfahren zur kontinuierlichen Herstellung von gesättigten aliphatischen Dicarbonsäuren
CH397650A (de)	1965-08-31	Verfahren zur Herstellung von Oximinoketonen
EP0021211B1 (fr)	1982-07-14	Procédé de préparation de carbonate de diméthyle
DE1959621C3 (de)	1979-02-08	Verfahren zur Gewinnung von Adipinsäure aus 6-Hydroperoxyhexansäure
EP0212217B1 (fr)	1989-01-04	Procédé de stabilisation d'eaux de lavage acides
DE1293736B (de)	1969-04-30	Verfahren zur Herstellung von Adipinsaeure
AT255399B (de)	1967-07-10	Verfahren zur Herstellung von substituierten oder unsubstituierten Adipinsäuren
US3219689A (en)	1965-11-23	Process for the oxidation of cycloalkane carboxylic acid
DE2354394C3 (de)	1979-10-18	Verfahren zur Herstellung von gesättigten aliphatischen Dicarbonsäuren
DE2820394A1 (de)	1978-11-23	Verfahren zur oxidation von p-methylbenzoesaeure
DE963508C (de)	1957-05-09	Verfahren zur Herstellung von o-Carboxyhydrozimtsaeure
DE1768138C (de)	1972-06-22	Verfahren zur Herstellung von Cyclo heptanon
DE2708115A1 (de)	1977-09-22	Verfahren zur herstellung von o-nitrobenzaldehyd
DE1518350A1 (de)	1969-07-24	Phenol aus Benzoesaeure
AT352097B (de)	1979-08-27	Verfahren zur herstellung von cyanformamid aus cyanwasserstoff und sauerstoff
DE3011175C2 (de)	1982-06-09	Verfahren zur Gewinnung von Dimethylterephthalat und Zwischenprodukten der DMT-Herstellung
AT232491B (de)	1964-03-25	Verfahren zur Herstellung von Adipinsäure und Nitrozyklohexan aus Zyklohexan
CH407082A (de)	1966-02-15	Verfahren zur gleichzeitigen Herstellung von Adipinsäure und Nitrozyklohexan aus Zyklohexan