RU2014123397A - Способ получения муравьиной кислоты путем взаимодействия диоксида углерода с водородом - Google Patents
Способ получения муравьиной кислоты путем взаимодействия диоксида углерода с водородом Download PDFInfo
- Publication number
- RU2014123397A RU2014123397A RU2014123397/04A RU2014123397A RU2014123397A RU 2014123397 A RU2014123397 A RU 2014123397A RU 2014123397/04 A RU2014123397/04 A RU 2014123397/04A RU 2014123397 A RU2014123397 A RU 2014123397A RU 2014123397 A RU2014123397 A RU 2014123397A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- carbon atoms
- phase
- formic acid
- phenyl
- Prior art date
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 title claims abstract 29
- 235000019253 formic acid Nutrition 0.000 title claims abstract 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract 5
- 239000001257 hydrogen Substances 0.000 title claims abstract 5
- 239000001569 carbon dioxide Substances 0.000 title claims abstract 3
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims 3
- 230000003993 interaction Effects 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 49
- 150000003512 tertiary amines Chemical class 0.000 claims abstract 17
- 239000003054 catalyst Substances 0.000 claims abstract 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract 12
- 239000000203 mixture Substances 0.000 claims abstract 12
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract 11
- 239000003446 ligand Substances 0.000 claims abstract 11
- 150000001412 amines Chemical class 0.000 claims abstract 9
- 239000002798 polar solvent Substances 0.000 claims abstract 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims abstract 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004429 atom Chemical group 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims abstract 4
- 230000000737 periodic effect Effects 0.000 claims abstract 4
- 125000002015 acyclic group Chemical group 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000004122 cyclic group Chemical group 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 239000011541 reaction mixture Substances 0.000 claims abstract 2
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 51
- 238000000034 method Methods 0.000 claims 12
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 10
- 239000005922 Phosphane Substances 0.000 claims 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 229910000064 phosphane Inorganic materials 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 238000004821 distillation Methods 0.000 claims 6
- 229910052723 transition metal Inorganic materials 0.000 claims 6
- 150000003624 transition metals Chemical class 0.000 claims 6
- 238000005191 phase separation Methods 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 4
- 238000005979 thermal decomposition reaction Methods 0.000 claims 4
- 238000000605 extraction Methods 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 238000003776 cleavage reaction Methods 0.000 claims 2
- -1 monosubstituted phenyl Chemical group 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 230000007017 scission Effects 0.000 claims 2
- VAFIOQDJWNKSKS-UHFFFAOYSA-N 2-di(pentadecyl)phosphanylethyl-di(pentadecyl)phosphane Chemical compound CCCCCCCCCCCCCCCP(CCCCCCCCCCCCCCC)CCP(CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC VAFIOQDJWNKSKS-UHFFFAOYSA-N 0.000 claims 1
- KDUHEBCVUCGLPX-UHFFFAOYSA-N 2-di(tetradecyl)phosphanylethyl-di(tetradecyl)phosphane Chemical compound CCCCCCCCCCCCCCP(CCCCCCCCCCCCCC)CCP(CCCCCCCCCCCCCC)CCCCCCCCCCCCCC KDUHEBCVUCGLPX-UHFFFAOYSA-N 0.000 claims 1
- ZLVYEKPGUBDXJK-UHFFFAOYSA-N 2-dihexadecylphosphanylethyl(dihexadecyl)phosphane Chemical compound CCCCCCCCCCCCCCCCP(CCCCCCCCCCCCCCCC)CCP(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC ZLVYEKPGUBDXJK-UHFFFAOYSA-N 0.000 claims 1
- SLSHEORECFFJJA-UHFFFAOYSA-N 2-dioctadecylphosphanylethyl(dioctadecyl)phosphane Chemical compound CCCCCCCCCCCCCCCCCCP(CCCCCCCCCCCCCCCCCC)CCP(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC SLSHEORECFFJJA-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
- GRAKJTASWCEOQI-UHFFFAOYSA-N tridodecylphosphane Chemical compound CCCCCCCCCCCCP(CCCCCCCCCCCC)CCCCCCCCCCCC GRAKJTASWCEOQI-UHFFFAOYSA-N 0.000 claims 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 claims 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 claims 1
- PKYBDXJPJDJCPS-UHFFFAOYSA-N tris-decylphosphane Chemical compound CCCCCCCCCCP(CCCCCCCCCC)CCCCCCCCCC PKYBDXJPJDJCPS-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Carbon And Carbon Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11188591 | 2011-11-10 | ||
| EP11188591.9 | 2011-11-10 | ||
| PCT/EP2012/072013 WO2013068389A1 (de) | 2011-11-10 | 2012-11-07 | Verfahren zur herstellung von ameisensäure durch umsetzung von kohlendioxid mit wasserstoff |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014123397A true RU2014123397A (ru) | 2015-12-20 |
Family
ID=47146398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014123397/04A RU2014123397A (ru) | 2011-11-10 | 2012-11-07 | Способ получения муравьиной кислоты путем взаимодействия диоксида углерода с водородом |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2776448A1 (de) |
| JP (1) | JP2015502922A (de) |
| KR (1) | KR20140090183A (de) |
| CN (1) | CN103917551A (de) |
| BR (1) | BR112014010923A2 (de) |
| CA (1) | CA2854047A1 (de) |
| IN (1) | IN2014DN03469A (de) |
| RU (1) | RU2014123397A (de) |
| SG (1) | SG11201401103YA (de) |
| WO (1) | WO2013068389A1 (de) |
| ZA (1) | ZA201404151B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9428438B2 (en) | 2012-11-27 | 2016-08-30 | Basf Se | Process for preparing formic acid |
| EP3936498A4 (de) * | 2019-03-08 | 2022-12-14 | Nitto Denko Corporation | Verfahren zur herstellung von ameisensäure |
| JP7405594B2 (ja) * | 2019-03-08 | 2023-12-26 | 日東電工株式会社 | ギ酸の製造方法 |
| US20230147963A1 (en) * | 2020-03-17 | 2023-05-11 | Nitto Denko Corporation | Formate production method and formate production system |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681481A (en) | 1969-11-12 | 1972-08-01 | Hooker Chemical Corp | Catalytic addition of compounds having a p-h bond to acetylene |
| DE3009487A1 (de) * | 1980-03-12 | 1981-09-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1,1-dihalogen-alkenen |
| CA1220222A (en) * | 1982-05-22 | 1987-04-07 | David J. Drury | Production of formate salts |
| JPS591140A (ja) * | 1982-06-23 | 1984-01-06 | Matsushita Electric Ind Co Ltd | 同心加工機 |
| GB8401005D0 (en) * | 1984-01-14 | 1984-02-15 | Bp Chem Int Ltd | Formate salts |
| GB8424672D0 (en) | 1984-09-29 | 1984-11-07 | Bp Chem Int Ltd | Production of formic acid |
| EP0357243B1 (de) * | 1988-08-20 | 1995-02-01 | BP Chemicals Limited | Produktion von Formiat-Salzen von Stickstoffbasen |
| DE19702025A1 (de) * | 1997-01-23 | 1998-07-30 | Studiengesellschaft Kohle Mbh | Verwendung perfluoralkylsubstituierter Phosphorverbindungen als Liganden für die homogene Katalyse in überkritischem Kohlendioxid |
| DE102004040789A1 (de) | 2004-08-23 | 2006-03-02 | Basf Ag | Verfahren zur Herstellung von Ameisensäure |
| WO2008116799A1 (de) * | 2007-03-23 | 2008-10-02 | Basf Se | Verfahren zur herstellung von ameisensäure |
| MY159513A (en) | 2009-06-26 | 2017-01-13 | Basf Se | Process for preparing formic acid |
-
2012
- 2012-11-07 RU RU2014123397/04A patent/RU2014123397A/ru not_active Application Discontinuation
- 2012-11-07 BR BR112014010923A patent/BR112014010923A2/pt not_active IP Right Cessation
- 2012-11-07 KR KR1020147012260A patent/KR20140090183A/ko not_active Application Discontinuation
- 2012-11-07 JP JP2014540431A patent/JP2015502922A/ja active Pending
- 2012-11-07 CN CN201280054841.XA patent/CN103917551A/zh active Pending
- 2012-11-07 IN IN3469DEN2014 patent/IN2014DN03469A/en unknown
- 2012-11-07 SG SG11201401103YA patent/SG11201401103YA/en unknown
- 2012-11-07 WO PCT/EP2012/072013 patent/WO2013068389A1/de active Application Filing
- 2012-11-07 EP EP12783595.7A patent/EP2776448A1/de not_active Withdrawn
- 2012-11-07 CA CA2854047A patent/CA2854047A1/en not_active Abandoned
-
2014
- 2014-06-06 ZA ZA2014/04151A patent/ZA201404151B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SG11201401103YA (en) | 2014-08-28 |
| WO2013068389A1 (de) | 2013-05-16 |
| JP2015502922A (ja) | 2015-01-29 |
| CN103917551A (zh) | 2014-07-09 |
| KR20140090183A (ko) | 2014-07-16 |
| EP2776448A1 (de) | 2014-09-17 |
| BR112014010923A2 (pt) | 2017-04-18 |
| IN2014DN03469A (de) | 2015-06-05 |
| ZA201404151B (en) | 2015-12-23 |
| CA2854047A1 (en) | 2013-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA93 | Acknowledgement of application withdrawn (no request for examination) |
Effective date: 20151110 |