CH657122A5 - Verfahren zur herstellung von carbonsaeuren aus acylfluoriden. - Google Patents

Verfahren zur herstellung von carbonsaeuren aus acylfluoriden. Download PDF

Info

Publication number: CH657122A5
Authority: CH; Switzerland
Prior art keywords: acid; fluoride; mixture; isobutyric acid; range
Prior art date: 1981-06-05

Application number

CH3475/82A

Other languages

German (de)

English (en)

Inventor

Richard V Norton

John E Jun Corn

Dace Grote

Ralph F Pascoe

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.)

1981-06-05

Filing date

1982-06-04

Publication date

1986-08-15

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

1986-08-15 Publication of CH657122A5 publication Critical patent/CH657122A5/de

Links

150000001265 acyl fluorides Chemical class 0.000 title claims description 47
238000004519 manufacturing process Methods 0.000 title claims description 7
150000004653 carbonic acids Chemical class 0.000 title 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 91
239000000203 mixture Substances 0.000 claims description 49
238000006243 chemical reaction Methods 0.000 claims description 47
238000000034 method Methods 0.000 claims description 47
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical compound CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 claims description 35
238000006460 hydrolysis reaction Methods 0.000 claims description 35
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 32
229910002091 carbon monoxide Inorganic materials 0.000 claims description 32
230000007062 hydrolysis Effects 0.000 claims description 29
150000002894 organic compounds Chemical class 0.000 claims description 28
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 16
-1 ethylene, propylene, isobutene Chemical class 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 12
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
150000001336 alkenes Chemical class 0.000 claims description 11
230000015572 biosynthetic process Effects 0.000 claims description 9
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 9
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 7
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
150000001735 carboxylic acids Chemical class 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 5
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
UIPSRNHDSBVXHY-UHFFFAOYSA-N 2,5-dichloropyridine-4-carbaldehyde Chemical compound ClC1=CC(C=O)=C(Cl)C=N1 UIPSRNHDSBVXHY-UHFFFAOYSA-N 0.000 claims description 4
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 4
WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 2
238000004821 distillation Methods 0.000 claims description 2
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 2
239000000047 product Substances 0.000 description 21
238000000926 separation method Methods 0.000 description 6
239000000463 material Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
150000002895 organic esters Chemical class 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000005810 carbonylation reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
NZDOWZQRNZLBOY-UHFFFAOYSA-N 2-fluoro-2-methylpropanoic acid Chemical compound CC(C)(F)C(O)=O NZDOWZQRNZLBOY-UHFFFAOYSA-N 0.000 description 1
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
241000220317 Rosa Species 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical compound [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000000567 combustion gas Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 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
- C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from 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

Landscapes

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

CH3475/82A 1981-06-05 1982-06-04 Verfahren zur herstellung von carbonsaeuren aus acylfluoriden. CH657122A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US27069881A	1981-06-05	1981-06-05

Publications (1)

Publication Number	Publication Date
CH657122A5 true CH657122A5 (de)	1986-08-15

Family

ID=23032417

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH3475/82A CH657122A5 (de)	1981-06-05	1982-06-04	Verfahren zur herstellung von carbonsaeuren aus acylfluoriden.

Country Status (12)

Country	Link
JP (1)	JPS6024086B2 (fr)
KR (1)	KR850001913B1 (fr)
AT (1)	AT389694B (fr)
AU (1)	AU532972B2 (fr)
BE (1)	BE893417A (fr)
CA (1)	CA1176657A (fr)
CH (1)	CH657122A5 (fr)
DE (1)	DE3221174C2 (fr)
FR (1)	FR2507179A1 (fr)
GB (2)	GB2099821B (fr)
IT (1)	IT1210894B (fr)
NL (1)	NL186959C (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3332436T1 (de) *	1982-02-18	1984-12-13	Ashland Oil Inc., Columbus, Ohio	Bildung von Isobuttersäure oder Methylisobutyrat
DE3213395A1 (de) *	1982-04-10	1983-10-13	Röhm GmbH, 6100 Darmstadt	Verfahren zur herstellung von isobuttersaeurefluorid bzw. isobuttersaeure
JPH07327833A (ja) *	1994-06-07	1995-12-19	Morii Kinzoku Kogyo Kk	鍋類、湯沸し類等の容器

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL302250A (fr) *	1963-01-21
GB1120714A (en) *	1965-07-22	1968-07-24	Distillers Co Yeast Ltd	Improvements in or relating to the production of carboxylic acids
NL6816940A (fr) *	1967-11-28	1969-05-30
BE755997A (fr) *	1969-09-11	1971-03-10	Bp Chem Int Ltd	Production d'acides dicarboxyliques
US3661951A (en) *	1969-12-01	1972-05-09	Armour Ind Chem Co	Carboxylation of olefins
DE2406223A1 (de) *	1974-02-09	1975-08-21	Basf Ag	Verfahren zur herstellung von carbonsaeuren
EP0031886B1 (fr) *	1979-12-20	1984-04-11	Röhm Gmbh	Procédé pour la préparation de l'acide isobutyrique ou de ses esters alcoyle inférieur

1982
- 1982-06-04 KR KR8202509A patent/KR850001913B1/ko not_active Expired
- 1982-06-04 CA CA000404467A patent/CA1176657A/fr not_active Expired
- 1982-06-04 NL NLAANVRAGE8202270,A patent/NL186959C/xx not_active IP Right Cessation
- 1982-06-04 IT IT8221708A patent/IT1210894B/it active
- 1982-06-04 FR FR8209807A patent/FR2507179A1/fr active Granted
- 1982-06-04 JP JP57096067A patent/JPS6024086B2/ja not_active Expired
- 1982-06-04 AU AU84606/82A patent/AU532972B2/en not_active Ceased
- 1982-06-04 BE BE0/208269A patent/BE893417A/fr not_active IP Right Cessation
- 1982-06-04 CH CH3475/82A patent/CH657122A5/de not_active IP Right Cessation
- 1982-06-04 GB GB8216301A patent/GB2099821B/en not_active Expired
- 1982-06-04 DE DE3221174A patent/DE3221174C2/de not_active Expired
- 1982-06-07 AT AT0220282A patent/AT389694B/de not_active IP Right Cessation
1984
- 1984-02-09 GB GB08403476A patent/GB2134113B/en not_active Expired

Also Published As

Publication number	Publication date
IT8221708A0 (it)	1982-06-04
AU8460682A (en)	1982-12-09
IT1210894B (it)	1989-09-29
GB2099821A (en)	1982-12-15
NL186959C (nl)	1991-04-16
AT389694B (de)	1990-01-10
JPS6024086B2 (ja)	1985-06-11
ATA220282A (de)	1989-06-15
GB2099821B (en)	1985-10-23
AU532972B2 (en)	1983-10-20
BE893417A (fr)	1982-10-01
NL8202270A (nl)	1983-01-03
NL186959B (nl)	1990-11-16
DE3221174C2 (de)	1985-06-20
FR2507179B1 (fr)	1985-05-17
GB2134113B (en)	1985-11-20
FR2507179A1 (fr)	1982-12-10
GB8403476D0 (en)	1984-03-14
CA1176657A (fr)	1984-10-23
KR850001913B1 (ko)	1985-12-31
DE3221174A1 (de)	1982-12-23
KR840000462A (ko)	1984-02-22
JPS57212134A (en)	1982-12-27
GB2134113A (en)	1984-08-08

Legal Events

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

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EP1888503B1 (fr)	2012-02-22	Procede de production de (meth)acrylates d'alkyle
DE69008499T2 (de)	1994-08-18	Veresterungsverfahren.
EP0031886A1 (fr)	1981-07-15	Procédé pour la préparation de l'acide isobutyrique ou de ses esters alcoyle inférieur
EP3663284A1 (fr)	2020-06-10	Procédé amélioré de production de triacétonamine
CH657122A5 (de)	1986-08-15	Verfahren zur herstellung von carbonsaeuren aus acylfluoriden.
DE69216856T2 (de)	1997-07-10	Verfahren zur herstellung von adipinsäure
EP0010236B2 (fr)	1987-04-15	Procédé de synthèse du 2,3-diméthyl-2,3-butane diol
DE3221173C2 (de)	1984-07-26	Verfahren zur Herstellung von Isobutyrylfluorid
DE3221172A1 (de)	1983-01-05	Verfahren zur herstellung von carbonsaeuren und estern
DE3034421C2 (fr)	1987-06-25
DE69806957T2 (de)	2003-02-06	Vinylether derivate
EP0267501B1 (fr)	1991-10-16	Procédé pour la fabrication continue de composés aliphatiques contenant des groupes carbalcoxyliques
EP0398095A2 (fr)	1990-11-22	Procédé de préparation de tris (chloro-2 isopropyl) ester d'acide phosphorique
DE2504005A1 (de)	1975-08-21	Verfahren zur herstellung von polyolestern von carbonsaeuren
CH657845A5 (de)	1986-09-30	Verfahren zur herstellung von carbonsaeureestern.
DE2814807A1 (de)	1978-10-26	Verfahren zur oxidation von butan zu essigsaeure
US3450741A (en)	1969-06-17	Production of omega-hydroxy-alkancarbonitriles
DE69805980T2 (de)	2003-01-23	Verfahren zur herstellung von carbonsäuren
DE2201456C3 (de)	1980-11-27	Verfahren zur Herstellung von Aldehyden und Diolen
EP0351616A2 (fr)	1990-01-24	Procédé de fabrication d'esters alkyliques de l'acide penténoique
DE3033655C2 (fr)	1988-02-04
DE4404742A1 (de)	1995-08-17	Verfahren zur Herstellung von Carbonsäuren und deren Estern
DE2258072C3 (de)	1977-06-02	Mono(beta-acetoxyäthyl)terephthalat und Verfahren zu seiner Gewinnung
DE3129013A1 (de)	1982-03-11	Verfahren zur herstellug von alkylidendiestern
DE1952848A1 (de)	1970-05-06	Verfahren zur Herstellung von omega-substituierten Lactonen