JPS6024088B2 - フッ化イソブチリルの製造方法 - Google Patents
フッ化イソブチリルの製造方法Info
- Publication number
- JPS6024088B2 JPS6024088B2 JP57096065A JP9606582A JPS6024088B2 JP S6024088 B2 JPS6024088 B2 JP S6024088B2 JP 57096065 A JP57096065 A JP 57096065A JP 9606582 A JP9606582 A JP 9606582A JP S6024088 B2 JPS6024088 B2 JP S6024088B2
- Authority
- JP
- Japan
- Prior art keywords
- propylene
- carbon monoxide
- pressure
- rate
- fluoride
- Prior art date
- 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
Links
- FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical compound CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 67
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 67
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 59
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 59
- 239000012071 phase Substances 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 239000007791 liquid phase Substances 0.000 claims description 13
- 150000008064 anhydrides Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 239000012530 fluid Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000007789 gas Substances 0.000 description 12
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
- 238000005810 carbonylation reaction Methods 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000006315 carbonylation Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 101100227721 Rattus norvegicus Frk gene Proteins 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 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
- 230000007062 hydrolysis Effects 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
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- -1 methyl isobutyrate Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 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
- C07C51/58—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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27876481A | 1981-06-29 | 1981-06-29 | |
| US278764 | 1981-06-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS588036A JPS588036A (ja) | 1983-01-18 |
| JPS6024088B2 true JPS6024088B2 (ja) | 1985-06-11 |
Family
ID=23066263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57096065A Expired JPS6024088B2 (ja) | 1981-06-29 | 1982-06-04 | フッ化イソブチリルの製造方法 |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS6024088B2 (nl) |
| KR (1) | KR850001914B1 (nl) |
| AT (1) | AT388160B (nl) |
| AU (1) | AU532639B2 (nl) |
| BE (1) | BE893419A (nl) |
| CA (1) | CA1173057A (nl) |
| CH (1) | CH660180A5 (nl) |
| DE (1) | DE3221172C2 (nl) |
| FR (1) | FR2508441B1 (nl) |
| GB (1) | GB2100729B (nl) |
| IT (1) | IT1195930B (nl) |
| NL (1) | NL187013C (nl) |
Families Citing this family (5)
| 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)
| 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 (nl) * | 1967-11-28 | 1969-05-30 | ||
| GB1232317A (nl) * | 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 |
| EP0017441B2 (en) * | 1979-04-09 | 1987-10-28 | CHEM SYSTEMS, Inc. | Preparation of esters |
-
1982
- 1982-06-03 AT AT0215082A patent/AT388160B/de not_active IP Right Cessation
- 1982-06-04 JP JP57096065A patent/JPS6024088B2/ja not_active Expired
- 1982-06-04 DE DE3221172A patent/DE3221172C2/de not_active Expired
- 1982-06-04 GB GB08216304A patent/GB2100729B/en not_active Expired
- 1982-06-04 KR KR8202507A patent/KR850001914B1/ko not_active Expired
- 1982-06-04 CA CA000404487A patent/CA1173057A/en not_active Expired
- 1982-06-04 IT IT21707/82A patent/IT1195930B/it active
- 1982-06-04 NL NLAANVRAGE8202268,A patent/NL187013C/nl not_active IP Right Cessation
- 1982-06-04 FR FR8209809A patent/FR2508441B1/fr not_active Expired
- 1982-06-04 AU AU84609/82A patent/AU532639B2/en not_active Ceased
- 1982-06-04 CH CH3476/82A patent/CH660180A5/de not_active IP Right Cessation
- 1982-06-04 BE BE0/208271A patent/BE893419A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2100729A (en) | 1983-01-06 |
| NL187013C (nl) | 1991-05-01 |
| FR2508441A1 (fr) | 1982-12-31 |
| AU532639B2 (en) | 1983-10-06 |
| FR2508441B1 (fr) | 1987-04-30 |
| CH660180A5 (de) | 1987-03-31 |
| NL8202268A (nl) | 1983-01-17 |
| BE893419A (fr) | 1982-10-01 |
| IT8221707A0 (it) | 1982-06-04 |
| AT388160B (de) | 1989-05-10 |
| KR840000461A (ko) | 1984-02-22 |
| ATA215082A (de) | 1988-10-15 |
| AU8460982A (en) | 1983-03-10 |
| GB2100729B (en) | 1985-10-30 |
| NL187013B (nl) | 1990-12-03 |
| IT1195930B (it) | 1988-11-03 |
| JPS588036A (ja) | 1983-01-18 |
| KR850001914B1 (ko) | 1985-12-31 |
| DE3221172C2 (de) | 1984-08-02 |
| CA1173057A (en) | 1984-08-21 |
| DE3221172A1 (de) | 1983-01-05 |
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