CH660180A5 - Verfahren zur herstellung eines acylium-fluorides. - Google Patents

Verfahren zur herstellung eines acylium-fluorides. Download PDF

Info

Publication number: CH660180A5
Authority: CH; Switzerland
Prior art keywords: carbon monoxide; organic compound; range; propylene; fluoride
Prior art date: 1981-06-29

Application number

CH3476/82A

Other languages

German (de)

English (en)

Inventor

Bhupendra C Trivedi

Dace Grote

Thomas O Mason

Original Assignee

Ashland Oil Inc

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.)

1981-06-29

Filing date

1982-06-04

Publication date

1987-03-31

1982-06-04 Application filed by Ashland Oil Inc filed Critical Ashland Oil Inc

1987-03-31 Publication of CH660180A5 publication Critical patent/CH660180A5/de

Links

KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title claims description 21
238000004519 manufacturing process Methods 0.000 title description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 94
229910002091 carbon monoxide Inorganic materials 0.000 claims description 91
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 72
150000002894 organic compounds Chemical class 0.000 claims description 60
238000000034 method Methods 0.000 claims description 45
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 44
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 38
239000002253 acid Substances 0.000 claims description 22
239000007791 liquid phase Substances 0.000 claims description 22
239000011541 reaction mixture Substances 0.000 claims description 21
FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical group CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 18
239000012808 vapor phase Substances 0.000 claims description 17
150000001336 alkenes Chemical class 0.000 claims description 15
239000007788 liquid Substances 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 12
-1 organic compound isopropyl isobutyrate Chemical class 0.000 claims description 11
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 8
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 6
WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 6
239000012071 phase Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
239000005977 Ethylene Substances 0.000 claims description 3
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 3
IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 claims description 2
238000003756 stirring Methods 0.000 claims description 2
229940024423 isopropyl isobutyrate Drugs 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
229910000040 hydrogen fluoride Inorganic materials 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
238000005810 carbonylation reaction Methods 0.000 description 4
BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000003245 coal Substances 0.000 description 3
150000002222 fluorine compounds Chemical class 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
UIPSRNHDSBVXHY-UHFFFAOYSA-N 2,5-dichloropyridine-4-carbaldehyde Chemical compound ClC1=CC(C=O)=C(Cl)C=N1 UIPSRNHDSBVXHY-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000006315 carbonylation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000001294 propane Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
VRBLNWVVFVBNRK-UHFFFAOYSA-N 1,6-diphenylhexane-1,6-dione Chemical compound C=1C=CC=CC=1C(=O)CCCCC(=O)C1=CC=CC=C1 VRBLNWVVFVBNRK-UHFFFAOYSA-N 0.000 description 1
WGCJTTUVWKJDAX-UHFFFAOYSA-N 1-fluoro-2-methylpropane Chemical compound CC(C)CF WGCJTTUVWKJDAX-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
WVRPFQGZHKZCEB-UHFFFAOYSA-N Isopropyl 2-methylpropanoate Chemical compound CC(C)OC(=O)C(C)C WVRPFQGZHKZCEB-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
208000002173 dizziness Diseases 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
229940082150 encore Drugs 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
238000011068 loading method Methods 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
IICQZTQZQSBHBY-UHFFFAOYSA-N non-2-ene Chemical group CCCCCCC=CC IICQZTQZQSBHBY-UHFFFAOYSA-N 0.000 description 1
NZGDDIUIXYFYFO-UHFFFAOYSA-N octane-2,7-dione Chemical compound CC(=O)CCCCC(C)=O NZGDDIUIXYFYFO-UHFFFAOYSA-N 0.000 description 1
QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH3476/82A 1981-06-29 1982-06-04 Verfahren zur herstellung eines acylium-fluorides. CH660180A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US27876481A	1981-06-29	1981-06-29

Publications (1)

Publication Number	Publication Date
CH660180A5 true CH660180A5 (de)	1987-03-31

Family

ID=23066263

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH3476/82A CH660180A5 (de)	1981-06-29	1982-06-04	Verfahren zur herstellung eines acylium-fluorides.

Country Status (12)

Country	Link
JP (1)	JPS6024088B2 (fr)
KR (1)	KR850001914B1 (fr)
AT (1)	AT388160B (fr)
AU (1)	AU532639B2 (fr)
BE (1)	BE893419A (fr)
CA (1)	CA1173057A (fr)
CH (1)	CH660180A5 (fr)
DE (1)	DE3221172C2 (fr)
FR (1)	FR2508441B1 (fr)
GB (1)	GB2100729B (fr)
IT (1)	IT1195930B (fr)
NL (1)	NL187013C (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ195559A (en) *	1979-11-29	1984-03-16	Ris Irrigation Syst	Butterfly sprinkler with dust protection for bearing
US4499029A (en) *	1983-06-15	1985-02-12	Ashland Oil, Inc.	Isobutyryl fluoride manufacture
DE3725428A1 (de) *	1987-07-31	1989-02-09	Basf Ag	Verfahren zur herstellung von carbonsaeurehalogeniden
FR2691965A1 (fr) *	1992-06-04	1993-12-10	Atochem Elf Sa	Procédé de fabrication de fluorure d'isobutyryle.
GB9917429D0 (en) *	1999-07-23	1999-09-22	Swan Thomas & Co Ltd	Carbonylation reactions

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE972291C (de) *	1954-05-16	1959-07-02	Studiengesellschaft Kohle Mbh	Verfahren zur Herstellung von Monocarbonsaeuren aus Olefinen, Kohlenoxyd und Wasser
DE973077C (de) *	1954-07-30	1959-11-26	Studiengesellschaft Kohle Mbh	Verfahren zur Herstellung von Carbonsaeuren aus Olefinen und Kohlenoxyd
DE1064941B (de) *	1957-04-24	1959-09-10	Studiengesellschaft Kohle Mbh	Verfahren zur Herstellung von Gemischen aus gesaettigten aliphatischen oder cycloaliphatischen Monocarbonsaeurealkylestern
US3065242A (en) *	1960-02-23	1962-11-20	Du Pont	Production of acyl halides, carboxylic acids and lactones
US3167585A (en) *	1960-08-25	1965-01-26	Gulf Research Development Co	Process for carboxylation of iso-olefins
GB942367A (en) *	1961-04-29	1963-11-20	Basf Ag	Continuous production of carboxylic acids from olefines, carbon monoxide and water
NL6816940A (fr) *	1967-11-28	1969-05-30
GB1232317A (fr) *	1968-12-30	1971-05-19
BE755997A (fr) *	1969-09-11	1971-03-10	Bp Chem Int Ltd	Production d'acides dicarboxyliques
DE2750719A1 (de) *	1977-11-12	1979-05-17	Roehm Gmbh	Verfahren zur herstellung von isobuttersaeure
US4224232A (en) *	1978-12-21	1980-09-23	Gulf Research & Development Company	Production of carboxylic acids from olefins and mixtures of olefins
DE3064472D1 (en) *	1979-04-09	1983-09-08	Chem Systems	Preparation of acids and esters

1982
- 1982-06-03 AT AT0215082A patent/AT388160B/de not_active IP Right Cessation
- 1982-06-04 IT IT21707/82A patent/IT1195930B/it active
- 1982-06-04 CH CH3476/82A patent/CH660180A5/de not_active IP Right Cessation
- 1982-06-04 AU AU84609/82A patent/AU532639B2/en not_active Ceased
- 1982-06-04 GB GB08216304A patent/GB2100729B/en not_active Expired
- 1982-06-04 JP JP57096065A patent/JPS6024088B2/ja not_active Expired
- 1982-06-04 FR FR8209809A patent/FR2508441B1/fr not_active Expired
- 1982-06-04 KR KR8202507A patent/KR850001914B1/ko not_active Expired
- 1982-06-04 BE BE0/208271A patent/BE893419A/fr not_active IP Right Cessation
- 1982-06-04 CA CA000404487A patent/CA1173057A/fr not_active Expired
- 1982-06-04 NL NLAANVRAGE8202268,A patent/NL187013C/xx not_active IP Right Cessation
- 1982-06-04 DE DE3221172A patent/DE3221172C2/de not_active Expired

Also Published As

Publication number	Publication date
GB2100729B (en)	1985-10-30
KR850001914B1 (ko)	1985-12-31
BE893419A (fr)	1982-10-01
FR2508441A1 (fr)	1982-12-31
IT8221707A0 (it)	1982-06-04
DE3221172A1 (de)	1983-01-05
KR840000461A (ko)	1984-02-22
AU8460982A (en)	1983-03-10
GB2100729A (en)	1983-01-06
JPS588036A (ja)	1983-01-18
ATA215082A (de)	1988-10-15
DE3221172C2 (de)	1984-08-02
CA1173057A (fr)	1984-08-21
IT1195930B (it)	1988-11-03
NL187013B (nl)	1990-12-03
AU532639B2 (en)	1983-10-06
FR2508441B1 (fr)	1987-04-30
JPS6024088B2 (ja)	1985-06-11
NL187013C (nl)	1991-05-01
AT388160B (de)	1989-05-10
NL8202268A (nl)	1983-01-17

Legal Events

Date	Code	Title	Description
1995-02-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0031886B1 (fr)	1984-04-11	Procédé pour la préparation de l'acide isobutyrique ou de ses esters alcoyle inférieur
DE1957167C3 (de)	1982-04-01	Verfahren zur Herstellung von Carbonsäuren durch Umsetzung von Olefinen mit Kohlenmonoxid und Wasser in Gegenwart eines Katalysators, der aus Orthophosphorsäure, Bortrifluorid und Wasser erhältlich ist
CH660180A5 (de)	1987-03-31	Verfahren zur herstellung eines acylium-fluorides.
EP0186076B1 (fr)	1990-09-26	Procédé de préparation de monoisobutyrate de 2,2,4-triméthyl-1,3-pentanediol
DE69406497T2 (de)	1998-03-12	Verfahren zur Herstellung von Estern
DE69702925T2 (de)	2001-03-15	Verfahren zur herstellung von vinylestern
DE2049049C3 (de)	1982-07-22	Verfahren zur Herstellung von Isopren aus Isobuten
EP0561213B1 (fr)	1995-10-25	Procédé de fabrication d'hydroxypivalate du néopentylglycole
DE3221173C2 (de)	1984-07-26	Verfahren zur Herstellung von Isobutyrylfluorid
EP0091604A1 (fr)	1983-10-19	Procédé de préparation de fluorure d'isobutyryl et/ou d'acide isobutyrique
DE2750719C2 (fr)	1987-06-04
CH657122A5 (de)	1986-08-15	Verfahren zur herstellung von carbonsaeuren aus acylfluoriden.
DE69805980T2 (de)	2003-01-23	Verfahren zur herstellung von carbonsäuren
EP0267501B1 (fr)	1991-10-16	Procédé pour la fabrication continue de composés aliphatiques contenant des groupes carbalcoxyliques
DE2337158C2 (de)	1987-01-02	Verfahren zur Herstellung von Alkancarbonsäuren
DE2142356B2 (de)	1980-05-08	Verfahren zur Oligomerisation von äthanhaltigem Äthylen
CH657845A5 (de)	1986-09-30	Verfahren zur herstellung von carbonsaeureestern.
EP0379971B1 (fr)	1993-03-24	Procédé continu pour la fabrication de l'acide isobutyrique
EP0101719A1 (fr)	1984-03-07	Formation d'acide isobutyrique ou d'isobutyrate de methyle.
AT374443B (de)	1984-04-25	Verfahren zur abtrennung eines olefins aus einem mischkohlenwasserstoff-raffineriestrom
DE3006223C2 (de)	1982-05-27	Verfahren zur Herstellung von 2,3,4,4-Tetrachlor-2-butensäure
DE2232644C3 (de)	1977-03-10	beta-Acyloxyäthyl-para-toluateund Verfahren zu ihrer Herstellung
DE2104206B2 (de)	1973-03-08	Verfahren zur kontinuierlichen herstellung von orthoameisensaeuremethyloder aethylester
DE3033655A1 (de)	1982-04-22	Verfahren zur herstellung von isobuttersaeure
DE2301632A1 (de)	1974-08-08	Verfahren zur herstellung von niederen alkoholen