CA1192576A - Production of an acylium anion product and carboxylic acids and esters therefrom - Google Patents

Production of an acylium anion product and carboxylic acids and esters therefrom

Info

Publication number: CA1192576A
Authority: CA; Canada
Prior art keywords: acid; carbon monoxide; psia; bars; recited
Prior art date: 1981-07-10
Legal status (The legal status 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 status listed.): Expired

Application number

CA000404491A

Other languages

English (en)

French (fr)

Inventor

John E. Corn, Jr.

Richard V. Norton

Ralph F. Pascoe

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ashland LLC

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.)

1981-07-10

Filing date

1982-06-04

Publication date

1985-08-27

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

1985-08-27 Application granted granted Critical

1985-08-27 Publication of CA1192576A publication Critical patent/CA1192576A/en

Status Expired legal-status Critical Current

Links

150000001450 anions Chemical class 0.000 title claims abstract description 39
150000002148 esters Chemical class 0.000 title description 12
150000001735 carboxylic acids Chemical class 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 80
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 77
239000002253 acid Substances 0.000 claims abstract description 68
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 35
150000002894 organic compounds Chemical class 0.000 claims abstract description 35
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 35
229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 27
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 20
FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical compound CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 claims abstract description 16
239000007791 liquid phase Substances 0.000 claims abstract description 16
230000006315 carbonylation Effects 0.000 claims abstract 3
238000005810 carbonylation reaction Methods 0.000 claims abstract 3
238000006243 chemical reaction Methods 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 34
239000007788 liquid Substances 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 14
150000001336 alkenes Chemical class 0.000 claims description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 5
150000002895 organic esters Chemical class 0.000 claims description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-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
229910052742 iron Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
WVRPFQGZHKZCEB-UHFFFAOYSA-N Isopropyl 2-methylpropanoate Chemical compound CC(C)OC(=O)C(C)C WVRPFQGZHKZCEB-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 3
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
229940024423 isopropyl isobutyrate Drugs 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 claims 2
239000012808 vapor phase Substances 0.000 claims 1
-1 propylene Chemical class 0.000 abstract description 15
150000002222 fluorine compounds Chemical class 0.000 abstract description 2
239000000047 product Substances 0.000 description 36
238000002156 mixing Methods 0.000 description 10
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 7
238000004821 distillation Methods 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
150000002500 ions Chemical class 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
241000605112 Scapanulus oweni Species 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
238000010586 diagram Methods 0.000 description 3
230000009977 dual effect Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000036647 reaction Effects 0.000 description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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 2
230000035484 reaction time Effects 0.000 description 2
CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
241000409886 Acion Species 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
229910000792 Monel Inorganic materials 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000003570 air Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000004350 aryl cycloalkyl group Chemical group 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
230000032050 esterification Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 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
- C07C51/12—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
- 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
- C07C51/58—Preparation of carboxylic acid halides

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)

CA000404491A 1981-07-10 1982-06-04 Production of an acylium anion product and carboxylic acids and esters therefrom Expired CA1192576A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US28213081A	1981-07-10	1981-07-10
US282,130		1981-07-10

Publications (1)

Publication Number	Publication Date
CA1192576A true CA1192576A (en)	1985-08-27

Family

ID=23080232

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000404491A Expired CA1192576A (en)	1981-07-10	1982-06-04	Production of an acylium anion product and carboxylic acids and esters therefrom

Country Status (19)

Country	Link
JP (1)	JPS6024089B2 (de)
KR (1)	KR850001912B1 (de)
AT (1)	AT392066B (de)
AU (1)	AU532911B1 (de)
BE (1)	BE893415A (de)
BR (1)	BR8203330A (de)
CA (1)	CA1192576A (de)
CH (1)	CH656608A5 (de)
DD (1)	DD207900A5 (de)
DE (1)	DE3221173C2 (de)
ES (2)	ES513956A0 (de)
FR (1)	FR2512811B1 (de)
GB (1)	GB2101591B (de)
IT (1)	IT1195931B (de)
NL (1)	NL187626C (de)
PL (1)	PL140231B1 (de)
RO (1)	RO83931B (de)
SE (1)	SE452609B (de)
ZA (1)	ZA823929B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0759531B2 (ja) *	1986-11-04	1995-06-28	三菱瓦斯化学株式会社	フツ化イソブチリルの合成方法
US5463095A (en) *	1993-06-15	1995-10-31	Mitsubishi Gas Chemical Company, Inc.	Process for the production of esters
BR102012020205A2 (pt) *	2012-08-13	2014-08-19	Cesar Roque Ecker	Aplicador de argamassa

Family Cites Families (8)

* 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
GB942367A (en) *	1961-04-29	1963-11-20	Basf Ag	Continuous production of carboxylic acids from olefines, carbon monoxide and water
NL6816940A (de) *	1967-11-28	1969-05-30
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

1982
- 1982-06-04 FR FR8209811A patent/FR2512811B1/fr not_active Expired
- 1982-06-04 IT IT21709/82A patent/IT1195931B/it active
- 1982-06-04 BE BE0/208267A patent/BE893415A/fr not_active IP Right Cessation
- 1982-06-04 DE DE3221173A patent/DE3221173C2/de not_active Expired
- 1982-06-04 ZA ZA823929A patent/ZA823929B/xx unknown
- 1982-06-04 JP JP57096066A patent/JPS6024089B2/ja not_active Expired
- 1982-06-04 ES ES513956A patent/ES513956A0/es active Granted
- 1982-06-04 RO RO107796A patent/RO83931B/ro unknown
- 1982-06-04 GB GB08216302A patent/GB2101591B/en not_active Expired
- 1982-06-04 CH CH3477/82A patent/CH656608A5/de not_active IP Right Cessation
- 1982-06-04 PL PL1982236785A patent/PL140231B1/pl unknown
- 1982-06-04 CA CA000404491A patent/CA1192576A/en not_active Expired
- 1982-06-04 DD DD82240468A patent/DD207900A5/de not_active IP Right Cessation
- 1982-06-04 SE SE8203478A patent/SE452609B/sv not_active IP Right Cessation
- 1982-06-04 AU AU84608/82A patent/AU532911B1/en not_active Ceased
- 1982-06-04 KR KR8202508A patent/KR850001912B1/ko not_active Expired
- 1982-06-04 NL NLAANVRAGE8202269,A patent/NL187626C/xx not_active IP Right Cessation
- 1982-06-04 AT AT0217782A patent/AT392066B/de not_active IP Right Cessation
- 1982-06-07 BR BR8203330A patent/BR8203330A/pt not_active IP Right Cessation
1983
- 1983-06-01 ES ES523258A patent/ES523258A0/es active Granted

Also Published As

Publication number	Publication date
SE452609B (sv)	1987-12-07
DE3221173C2 (de)	1984-07-26
ZA823929B (en)	1983-11-30
GB2101591A (en)	1983-01-19
PL236785A1 (en)	1983-02-14
ES8500208A1 (es)	1984-10-01
FR2512811A1 (fr)	1983-03-18
ES523258A0 (es)	1984-10-01
NL187626B (nl)	1991-07-01
BR8203330A (pt)	1983-05-24
KR850001912B1 (ko)	1985-12-31
IT1195931B (it)	1988-11-03
JPS5810535A (ja)	1983-01-21
KR840000464A (ko)	1984-02-22
CH656608A5 (de)	1986-07-15
RO83931A (ro)	1984-04-12
AU532911B1 (en)	1983-10-20
AT392066B (de)	1991-01-25
IT8221709A0 (it)	1982-06-04
GB2101591B (en)	1985-11-27
PL140231B1 (en)	1987-04-30
NL8202269A (nl)	1983-02-01
ES8400376A1 (es)	1983-10-16
BE893415A (fr)	1982-10-01
DD207900A5 (de)	1984-03-21
ES513956A0 (es)	1983-10-16
FR2512811B1 (fr)	1985-07-05
RO83931B (ro)	1984-05-30
JPS6024089B2 (ja)	1985-06-11
ATA217782A (de)	1990-07-15
SE8203478L (sv)	1983-01-11
NL187626C (nl)	1991-12-02
DE3221173A1 (de)	1983-01-27

Legal Events

Date	Code	Title	Description
2002-08-27	MKEX	Expiry

Publication	Publication Date	Title
US3769329A (en)	1973-10-30	Production of carboxylic acids and esters
KR100220824B1 (ko)	1999-09-15	올레핀 카르보닐화 방법 및 상기 방법에 적절한 촉매 시스템
EP0665210B1 (de)	1998-11-04	Verfahren zur herstellung von acetanhydrid oder einer mischung von acetanhydrid und essigsäure
US3725534A (en)	1973-04-03	Method of forming complex cobalt carbonyl compounds
JP3656030B2 (ja)	2005-06-02	第３級ブチルアルコールの製造方法
US4111982A (en)	1978-09-05	Coproduction of acetic and propionic acids
EP0283586B1 (de)	1993-03-17	Homologierungsverfahren
US4256913A (en)	1981-03-17	Preparation of carboxylic acids using a BF3 catalyst complex
EP0580735A1 (de)	1994-02-02	Herstellung von trialkylacetsäuren, im besonderen pivalinsäure mit festen sauren katalysatoren
KR102397805B1 (ko)	2022-05-12	아세트산 생산 방법
US20080269459A1 (en)	2008-10-30	Process for the Preparation of a Dicarboxylic Acid
US3793369A (en)	1974-02-19	Process for production of carboxylic esters
KR890003785B1 (ko)	1989-10-04	카복실산의 제조방법
US3778468A (en)	1973-12-11	Process for preparing ethylene glycol esters
EP0042633B1 (de)	1984-06-20	Verfahren zum Carbonylieren von Alkanolen und/oder Äthern
JPH0148889B2 (de)	1989-10-20
CA1173057A (en)	1984-08-21	Production of carboxylic acids and esters
GB2101591A (en)	1983-01-19	Production of acyl halides and carboxylic acids and esters therefrom
JPS63192738A (ja)	1988-08-10	カルボニル化法
EP0077116A1 (de)	1983-04-20	Herstellung von Alkylidendiestern
EP0101719B1 (de)	1987-05-06	Herstellung von isobuttersäure oder methylisobutyrat
US12552734B2 (en)	2026-02-17	Process for producing acetic acid
EP0060695A1 (de)	1982-09-22	Verfahren zur Coproduktion einer C2 bis C10 Monocarbonsäure und Ameisensäure
KR850001915B1 (ko)	1985-12-31	카르보닐화 반응에 의해 생성된 불화이소부티릴로부터의 카르복실산 에스테르류의 제조 방법
GB2099821A (en)	1982-12-15	Production of carboxylic acids from acyl fluorides formed by carbonylation