SE452609B - Forfarande for karbonylering av olefiner genom omsettning med kolmonooxid i nervaro av vattenfri syra - Google Patents
Forfarande for karbonylering av olefiner genom omsettning med kolmonooxid i nervaro av vattenfri syraInfo
- Publication number
- SE452609B SE452609B SE8203478A SE8203478A SE452609B SE 452609 B SE452609 B SE 452609B SE 8203478 A SE8203478 A SE 8203478A SE 8203478 A SE8203478 A SE 8203478A SE 452609 B SE452609 B SE 452609B
- Authority
- SE
- Sweden
- Prior art keywords
- carbon monoxide
- propylene
- bar
- acid
- reaction
- Prior art date
Links
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 title claims description 71
- 229910002091 carbon monoxide Inorganic materials 0.000 title claims description 69
- 239000002253 acid Substances 0.000 title claims description 52
- 238000000034 method Methods 0.000 title claims description 26
- 230000006315 carbonylation Effects 0.000 title claims 3
- 238000005810 carbonylation reaction Methods 0.000 title claims 3
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 150000001450 anions Chemical class 0.000 claims description 33
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 28
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 27
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 24
- FSQOYWQCIXSBNP-UHFFFAOYSA-N 2-methylpropanoyl fluoride Chemical compound CC(C)C(F)=O FSQOYWQCIXSBNP-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 13
- 239000007791 liquid phase Substances 0.000 claims description 13
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- 239000011541 reaction mixture 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 41
- 150000002894 organic compounds Chemical class 0.000 description 18
- 238000002156 mixing Methods 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 10
- -1 propene Chemical compound 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- CUPFNGOKRMWUOO-UHFFFAOYSA-N hydron;difluoride Chemical compound F.F CUPFNGOKRMWUOO-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 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
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 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
- NJCQVAKYBOCUCS-UHFFFAOYSA-N [C].F Chemical compound [C].F NJCQVAKYBOCUCS-UHFFFAOYSA-N 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000567 combustion gas Substances 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 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
- 235000019260 propionic acid Nutrition 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
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000012808 vapor phase Substances 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28213081A | 1981-07-10 | 1981-07-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8203478L SE8203478L (sv) | 1983-01-11 |
| SE452609B true SE452609B (sv) | 1987-12-07 |
Family
ID=23080232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8203478A SE452609B (sv) | 1981-07-10 | 1982-06-04 | Forfarande for karbonylering av olefiner genom omsettning med kolmonooxid i nervaro av vattenfri syra |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS6024089B2 (pl) |
| KR (1) | KR850001912B1 (pl) |
| AT (1) | AT392066B (pl) |
| AU (1) | AU532911B1 (pl) |
| BE (1) | BE893415A (pl) |
| BR (1) | BR8203330A (pl) |
| CA (1) | CA1192576A (pl) |
| CH (1) | CH656608A5 (pl) |
| DD (1) | DD207900A5 (pl) |
| DE (1) | DE3221173C2 (pl) |
| ES (2) | ES513956A0 (pl) |
| FR (1) | FR2512811B1 (pl) |
| GB (1) | GB2101591B (pl) |
| IT (1) | IT1195931B (pl) |
| NL (1) | NL187626C (pl) |
| PL (1) | PL140231B1 (pl) |
| RO (1) | RO83931B (pl) |
| SE (1) | SE452609B (pl) |
| ZA (1) | ZA823929B (pl) |
Families Citing this family (3)
| 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)
| 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 (pl) * | 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 GB GB08216302A patent/GB2101591B/en not_active Expired
- 1982-06-04 DD DD82240468A patent/DD207900A5/de not_active IP Right Cessation
- 1982-06-04 NL NLAANVRAGE8202269,A patent/NL187626C/xx not_active IP Right Cessation
- 1982-06-04 CA CA000404491A patent/CA1192576A/en not_active Expired
- 1982-06-04 AU AU84608/82A patent/AU532911B1/en not_active Ceased
- 1982-06-04 CH CH3477/82A patent/CH656608A5/de not_active IP Right Cessation
- 1982-06-04 KR KR8202508A patent/KR850001912B1/ko not_active Expired
- 1982-06-04 BE BE0/208267A patent/BE893415A/fr not_active IP Right Cessation
- 1982-06-04 PL PL1982236785A patent/PL140231B1/pl unknown
- 1982-06-04 ES ES513956A patent/ES513956A0/es active Granted
- 1982-06-04 DE DE3221173A patent/DE3221173C2/de not_active Expired
- 1982-06-04 SE SE8203478A patent/SE452609B/sv not_active IP Right Cessation
- 1982-06-04 RO RO107796A patent/RO83931B/ro unknown
- 1982-06-04 ZA ZA823929A patent/ZA823929B/xx unknown
- 1982-06-04 JP JP57096066A patent/JPS6024089B2/ja not_active Expired
- 1982-06-04 AT AT0217782A patent/AT392066B/de not_active IP Right Cessation
- 1982-06-04 FR FR8209811A patent/FR2512811B1/fr not_active Expired
- 1982-06-04 IT IT21709/82A patent/IT1195931B/it active
- 1982-06-07 BR BR8203330A patent/BR8203330A/pt not_active IP Right Cessation
-
1983
- 1983-06-01 ES ES523258A patent/ES8500208A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES8400376A1 (es) | 1983-10-16 |
| DE3221173A1 (de) | 1983-01-27 |
| AT392066B (de) | 1991-01-25 |
| SE8203478L (sv) | 1983-01-11 |
| GB2101591B (en) | 1985-11-27 |
| DD207900A5 (de) | 1984-03-21 |
| IT8221709A0 (it) | 1982-06-04 |
| BR8203330A (pt) | 1983-05-24 |
| CH656608A5 (de) | 1986-07-15 |
| PL236785A1 (en) | 1983-02-14 |
| RO83931B (ro) | 1984-05-30 |
| KR840000464A (ko) | 1984-02-22 |
| JPS6024089B2 (ja) | 1985-06-11 |
| ES523258A0 (es) | 1984-10-01 |
| GB2101591A (en) | 1983-01-19 |
| NL187626B (nl) | 1991-07-01 |
| NL8202269A (nl) | 1983-02-01 |
| IT1195931B (it) | 1988-11-03 |
| ES8500208A1 (es) | 1984-10-01 |
| BE893415A (fr) | 1982-10-01 |
| RO83931A (ro) | 1984-04-12 |
| ATA217782A (de) | 1990-07-15 |
| DE3221173C2 (de) | 1984-07-26 |
| FR2512811A1 (fr) | 1983-03-18 |
| ES513956A0 (es) | 1983-10-16 |
| KR850001912B1 (ko) | 1985-12-31 |
| FR2512811B1 (fr) | 1985-07-05 |
| PL140231B1 (en) | 1987-04-30 |
| NL187626C (nl) | 1991-12-02 |
| ZA823929B (en) | 1983-11-30 |
| JPS5810535A (ja) | 1983-01-21 |
| AU532911B1 (en) | 1983-10-20 |
| CA1192576A (en) | 1985-08-27 |
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Legal Events
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