NO131245B - - Google Patents

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Info

Publication number: NO131245B
Authority: NO; Norway
Prior art keywords: acetone; catalyst; reaction; hydrogen; palladium
Prior art date: 1967-09-08

Application number

NO343268A

Other languages

English (en)

Norwegian (no)

Other versions

NO131245C (de

Inventor

K Schmitt

J Disteldorf

W Flakus

W Huebel

Original Assignee

Scholven Chemie Ag

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.)

1967-09-08

Filing date

1968-09-04

Publication date

1975-01-20

1968-09-04 Application filed by Scholven Chemie Ag filed Critical Scholven Chemie Ag

1975-01-20 Publication of NO131245B publication Critical patent/NO131245B/no

1975-05-07 Publication of NO131245C publication Critical patent/NO131245C/no

Links

CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 54
239000003054 catalyst Substances 0.000 claims description 30
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
229910052763 palladium Inorganic materials 0.000 claims description 14
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 11
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 11
150000002500 ions Chemical class 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 8
150000001768 cations Chemical class 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
230000007935 neutral effect Effects 0.000 claims description 3
-1 palladium cations Chemical class 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
239000007789 gas Substances 0.000 description 8
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 5
238000006703 hydration reaction Methods 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 4
230000036571 hydration Effects 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229910000510 noble metal Inorganic materials 0.000 description 4
230000007306 turnover Effects 0.000 description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 3
WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000009826 distribution Methods 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
239000000047 product 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
JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical compound CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000010970 precious metal Substances 0.000 description 2
238000003825 pressing Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000011437 continuous method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000011049 filling Methods 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
230000001788 irregular Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000010327 methods by industry Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000008262 pumice Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000000243 solution Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
- 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
- C07C45/67—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 isomerisation; by change of size of the carbon skeleton
- C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/349—1,2- or 1,4-additions in combination with further or prior reactions by the same catalyst, i.e. tandem or domino reactions, e.g. hydrogenation or further addition reactions

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Inorganic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO343268A 1967-09-08 1968-09-04 NO131245C (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1967SC041273 DE1643044A1 (de)	1967-09-08	1967-09-08	Verfahren zur Herstellung von Methylisobutylketon

Publications (2)

Publication Number	Publication Date
NO131245B true NO131245B (de)	1975-01-20
NO131245C NO131245C (de)	1975-05-07

Family

ID=7436139

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO343268A NO131245C (de)	1967-09-08	1968-09-04

Country Status (11)

Country	Link
JP (1)	JPS5215573B1 (de)
AT (1)	AT283298B (de)
BE (1)	BE720525A (de)
DE (1)	DE1643044A1 (de)
DK (1)	DK123291B (de)
ES (1)	ES357716A1 (de)
IE (1)	IE32465B1 (de)
LU (1)	LU56802A1 (de)
NL (1)	NL170948C (de)
NO (1)	NO131245C (de)
SE (1)	SE365195B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4270006A (en) *	1979-12-27	1981-05-26	Basf Aktiengesellschaft	Preparation of aliphatic carbonyl compounds
DE3120213A1 (de) *	1981-05-21	1982-12-09	Bayer Ag, 5090 Leverkusen	Verfahren zur durchfuehrung katalytischer reaktionen in waessrigen medien
US6977314B2 (en) *	2001-12-19	2005-12-20	Rohm And Haas Company	Metal-doped sulfonated ion exchange resin catalysts

1967
- 1967-09-08 DE DE1967SC041273 patent/DE1643044A1/de active Granted
1968
- 1968-08-26 AT AT828168A patent/AT283298B/de not_active IP Right Cessation
- 1968-08-27 IE IE105368A patent/IE32465B1/xx unknown
- 1968-08-29 NL NL6812327A patent/NL170948C/xx not_active IP Right Cessation
- 1968-08-30 ES ES357716A patent/ES357716A1/es not_active Expired
- 1968-08-30 LU LU56802D patent/LU56802A1/xx unknown
- 1968-09-04 NO NO343268A patent/NO131245C/no unknown
- 1968-09-06 BE BE720525D patent/BE720525A/xx unknown
- 1968-09-09 SE SE1210068A patent/SE365195B/xx unknown
- 1968-09-09 DK DK431968A patent/DK123291B/da unknown
- 1968-09-09 JP JP6458568A patent/JPS5215573B1/ja active Pending

Also Published As

Publication number	Publication date
JPS5215573B1 (de)	1977-04-30
SE365195B (de)	1974-03-18
DK123291B (da)	1972-06-05
IE32465L (en)	1969-03-08
AT283298B (de)	1970-07-27
NO131245C (de)	1975-05-07
NL6812327A (de)	1969-03-11
BE720525A (de)	1969-02-17
NL170948C (nl)	1983-01-17
LU56802A1 (de)	1968-11-22
IE32465B1 (en)	1973-08-08
ES357716A1 (es)	1970-03-16
NL170948B (nl)	1982-08-16
DE1643044A1 (de)	1971-04-15

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US5583263A (en)	1996-12-10	Process of making ketones
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DE2537890A1 (de)	1976-03-11	Verfahren zur herstellung von diacetoxybutan und butandiol
NO131245B (de)	1975-01-20
US2130592A (en)	1938-09-20	Aldol condensation process
US4847440A (en)	1989-07-11	Method of manufacturing propynol
DE3803581A1 (de)	1989-08-17	Verfahren zur herstellung von 1,2,4-butantriol
Otey et al.	1961	Erythritol and ethylene glycol from dialdehyde starch
DE1793302C3 (de)	1974-05-02
JPS604139A (ja)	1985-01-10	選択的水素添加方法
DE1643044C3 (de)	1977-10-06	Verfahren zur Herstellung von Methylisobutylketon
DE69905053T2 (de)	2003-08-14	Verfahren zur herstellung von cyclobutyl haliden
US3574764A (en)	1971-04-13	Process for producing saturated aliphatic aldehydes
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DE2645712C2 (de)	1983-08-04	Verfahren zur Herstellung von sekundären Aminen durch Umsetzung von Ammoniak mit primären oder sekundären ein- oder mehrwertigen Alkoholen
US2546103A (en)	1951-03-20	Process of manufacturing hexitols by catalytic reduction of carbohydrates
DE1245352B (de)	1967-07-27	Verfahren zur kontinuierlichen Herstellung von Aldehyden
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DE569019C (de)	1933-01-31	Verfahren zur Herstellung von Alkoholen
DE1277249B (de)	1968-09-12	Verfahren zur Herstellung von Vinylacetat
DE840695C (de)	1952-06-05	Verfahren zur Herstellung von 1, 1, 3-Trimethylcyclohexanon-5
DE1904236A1 (de)	1970-08-06	Verfahren zur Herstellung von Allylidendiacetat
US3641163A (en)	1972-02-08	Process for preparing dimethylacetal