CH410910A - Verfahren zur Herstellung von Enolacetaten - Google Patents

Verfahren zur Herstellung von Enolacetaten

Info

Publication number: CH410910A
Authority: CH; Switzerland
Prior art keywords: ketene; mol; acetone; reaction; acid
Prior art date: 1959-06-02

Application number

CH292160A

Other languages

German (de)

English (en)

Inventor

Theodor Dr Altenschoepfer

Eduard Dr Enk

Fritz Dr Knoerr

Hellmuth Dr Spes

Original Assignee

Wacker Chemie Gmbh

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.)

1959-06-02

Filing date

1960-03-15

Publication date

1966-04-15

1960-03-15 Application filed by Wacker Chemie Gmbh filed Critical Wacker Chemie Gmbh

1966-04-15 Publication of CH410910A publication Critical patent/CH410910A/de

Links

-1 enol acetates Chemical class 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 3
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 81
239000003054 catalyst Substances 0.000 claims description 31
QTZBTBLHYPSFMG-UHFFFAOYSA-N 5-chloro-3-methylpyridin-2-amine Chemical compound CC1=CC(Cl)=CN=C1N QTZBTBLHYPSFMG-UHFFFAOYSA-N 0.000 claims description 24
150000001728 carbonyl compounds Chemical class 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 15
239000007795 chemical reaction product Substances 0.000 claims description 12
239000000376 reactant Substances 0.000 claims description 10
DWYMPOCYEZONEA-UHFFFAOYSA-N fluorophosphoric acid Chemical compound OP(O)(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-N 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 2
241001026509 Kata Species 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 88
238000006243 chemical reaction Methods 0.000 description 45
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 42
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 31
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 16
238000004821 distillation Methods 0.000 description 11
238000010521 absorption reaction Methods 0.000 description 9
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
238000006386 neutralization reaction Methods 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 7
235000020075 ouzo Nutrition 0.000 description 7
239000001632 sodium acetate Substances 0.000 description 7
235000017281 sodium acetate Nutrition 0.000 description 7
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
229910052753 mercury Inorganic materials 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 5
239000011521 glass Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
238000005292 vacuum distillation Methods 0.000 description 4
HWCUCNKPBMGSSC-UHFFFAOYSA-N 1-phenylethenyl acetate Chemical compound CC(=O)OC(=C)C1=CC=CC=C1 HWCUCNKPBMGSSC-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
NLAMRLZPVVKXTK-UHFFFAOYSA-N but-1-enyl acetate Chemical compound CCC=COC(C)=O NLAMRLZPVVKXTK-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000005837 enolization reaction Methods 0.000 description 2
238000007710 freezing Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
DXFWOAOOMXEACN-UHFFFAOYSA-N 3-oxo-2-sulfobutanoic acid Chemical compound CC(=O)C(C(O)=O)S(O)(=O)=O DXFWOAOOMXEACN-UHFFFAOYSA-N 0.000 description 1
ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000010923 batch production Methods 0.000 description 1
125000003180 beta-lactone group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
GNEVIACKFGQMHB-UHFFFAOYSA-N carbon suboxide Chemical compound O=C=C=C=O GNEVIACKFGQMHB-UHFFFAOYSA-N 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
238000010924 continuous production Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002085 enols Chemical group 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
RHFUXPCCELGMFC-UHFFFAOYSA-N n-(6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-n-phenylmethoxyacetamide Chemical compound OC1C(C)(C)OC2=CC=C(C#N)C=C2C1N(C(=O)C)OCC1=CC=CC=C1 RHFUXPCCELGMFC-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
KBVUALKOHTZCGR-UHFFFAOYSA-M sodium;difluorophosphinate Chemical compound [Na+].[O-]P(F)(F)=O KBVUALKOHTZCGR-UHFFFAOYSA-M 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
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/46—Preparation of carboxylic acid esters from ketenes or polyketenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH292160A 1959-06-02 1960-03-15 Verfahren zur Herstellung von Enolacetaten CH410910A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEW25734A DE1121605B (de)	1959-06-02	1959-06-02	Verfahren zur Herstellung von Enolacetaten

Publications (1)

Publication Number	Publication Date
CH410910A true CH410910A (de)	1966-04-15

Family

ID=7598160

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH292160A CH410910A (de)	1959-06-02	1960-03-15	Verfahren zur Herstellung von Enolacetaten

Country Status (4)

Country	Link
BE (1)	BE591509A (fr)
CH (1)	CH410910A (fr)
DE (1)	DE1121605B (fr)
GB (1)	GB920372A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19634147A1 (de) *	1996-08-23	1998-02-26	Basf Ag	Verfahren zur Herstellung von 1-Acetyl-4-piperidonen
CN111448180B (zh) *	2017-12-18	2023-08-15	巴斯夫欧洲公司	通过烯酮化合物制备乙酸酯化合物

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1014104B (de)	1956-04-13	1957-08-22	Wacker Chemie Gmbh	Verfahren zur Herstellung von Isopropenylacetat

1959
- 1959-06-02 DE DEW25734A patent/DE1121605B/de active Pending
1960
- 1960-03-15 CH CH292160A patent/CH410910A/de unknown
- 1960-06-02 BE BE591509A patent/BE591509A/fr unknown
- 1960-06-02 GB GB19630/60A patent/GB920372A/en not_active Expired

Also Published As

Publication number	Publication date
BE591509A (fr)	1960-12-02
GB920372A (en)	1963-03-06
DE1121605B (de)	1962-01-11

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