CN102958894B - 制备甲酸的方法 - Google Patents
制备甲酸的方法 Download PDFInfo
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- CN102958894B CN102958894B CN201180031930.8A CN201180031930A CN102958894B CN 102958894 B CN102958894 B CN 102958894B CN 201180031930 A CN201180031930 A CN 201180031930A CN 102958894 B CN102958894 B CN 102958894B
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- Prior art keywords
- formic acid
- stream
- tertiary amine
- amine
- tower
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 title claims abstract description 775
- 235000019253 formic acid Nutrition 0.000 title claims abstract description 387
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 title claims abstract description 385
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 165
- 238000000034 method Methods 0.000 claims abstract description 101
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- 239000007788 liquid Substances 0.000 claims abstract description 42
- 238000000926 separation method Methods 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 181
- 239000012071 phase Substances 0.000 claims description 58
- 150000001412 amines Chemical class 0.000 claims description 55
- 238000007599 discharging Methods 0.000 claims description 34
- 238000009835 boiling Methods 0.000 claims description 30
- 238000006460 hydrolysis reaction Methods 0.000 claims description 25
- 230000007062 hydrolysis Effects 0.000 claims description 24
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- 239000006200 vaporizer Substances 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 16
- 229910000765 intermetallic Inorganic materials 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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- -1 alkyl imidazole Chemical compound 0.000 description 33
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- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
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- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
- WBGPDYJIPNTOIB-UHFFFAOYSA-N n,n-dibenzylethanamine Chemical compound C=1C=CC=CC=1CN(CC)CC1=CC=CC=C1 WBGPDYJIPNTOIB-UHFFFAOYSA-N 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- MMFBQHXDINNBMW-UHFFFAOYSA-N n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=CC=C1 MMFBQHXDINNBMW-UHFFFAOYSA-N 0.000 description 1
- GXFHZISVUPJOCI-UHFFFAOYSA-N n-(2-ethylhexyl)aniline Chemical compound CCCCC(CC)CNC1=CC=CC=C1 GXFHZISVUPJOCI-UHFFFAOYSA-N 0.000 description 1
- WYZDCUGWXKHESN-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=CC=C1 WYZDCUGWXKHESN-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- POMGZMHIXYRARC-UHFFFAOYSA-N n-hexyl-n-methylhexan-1-amine Chemical compound CCCCCCN(C)CCCCCC POMGZMHIXYRARC-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012207 quantitative assay Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- SLRCCWJSBJZJBV-AJNGGQMLSA-N sparteine Chemical compound C1N2CCCC[C@H]2[C@@H]2CN3CCCC[C@H]3[C@H]1C2 SLRCCWJSBJZJBV-AJNGGQMLSA-N 0.000 description 1
- 229960001945 sparteine Drugs 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical compound C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 description 1
- 229930004006 tropane Natural products 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- 239000010457 zeolite 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- 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
- C07C53/02—Formic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10167679.9 | 2010-06-29 | ||
| EP10167679 | 2010-06-29 | ||
| EP10187280.2 | 2010-10-12 | ||
| EP10187280 | 2010-10-12 | ||
| PCT/EP2011/060770 WO2012000964A1 (de) | 2010-06-29 | 2011-06-28 | Verfahren zur herstellung von ameisensäure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102958894A CN102958894A (zh) | 2013-03-06 |
| CN102958894B true CN102958894B (zh) | 2015-04-15 |
Family
ID=44627755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180031930.8A Expired - Fee Related CN102958894B (zh) | 2010-06-29 | 2011-06-28 | 制备甲酸的方法 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP2588440A1 (de) |
| JP (1) | JP2013533869A (de) |
| KR (1) | KR20130088838A (de) |
| CN (1) | CN102958894B (de) |
| BR (1) | BR112012032211A2 (de) |
| CA (1) | CA2801580A1 (de) |
| RU (1) | RU2013103601A (de) |
| SG (1) | SG186264A1 (de) |
| WO (1) | WO2012000964A1 (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8877965B2 (en) | 2010-06-29 | 2014-11-04 | Basf Se | Process for preparing formic acid by reaction of carbon dioxide with hydrogen |
| BR112013015395A2 (pt) * | 2010-12-21 | 2016-09-20 | Basf Se | processo para preparar ácido fórmico |
| US8742171B2 (en) | 2011-06-09 | 2014-06-03 | Basf Se | Process for preparing formic acid |
| US8993819B2 (en) | 2011-07-12 | 2015-03-31 | Basf Se | Process for preparing cycloheptene |
| US8703994B2 (en) | 2011-07-27 | 2014-04-22 | Basf Se | Process for preparing formamides and formic esters |
| US8946462B2 (en) | 2011-11-10 | 2015-02-03 | Basf Se | Process for preparing formic acid by reaction of carbon dioxide with hydrogen |
| US8835683B2 (en) | 2011-12-20 | 2014-09-16 | Basf Se | Process for preparing formic acid |
| US8889905B2 (en) | 2011-12-20 | 2014-11-18 | Basf Se | Process for preparing formic acid |
| BR112014012602A2 (pt) * | 2011-12-20 | 2017-06-20 | Basf Se | processo para obter ácido fórmico |
| US9428438B2 (en) | 2012-11-27 | 2016-08-30 | Basf Se | Process for preparing formic acid |
| CN104812731A (zh) * | 2012-11-27 | 2015-07-29 | 巴斯夫欧洲公司 | 生产甲酸的方法 |
| CN110980763B (zh) * | 2019-12-24 | 2022-10-18 | 福州大学 | 一种分子筛的改性方法和用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101006038A (zh) * | 2004-08-23 | 2007-07-25 | 巴斯福股份公司 | 制备甲酸的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2545658C2 (de) | 1975-10-11 | 1985-12-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung von Carbonsäuren aus ihren wäßrigen Lösungen |
| DE2744313A1 (de) | 1977-10-01 | 1979-04-12 | Basf Ag | Verfahren zur herstellung von ameisensaeure |
| GB8307611D0 (en) | 1983-03-18 | 1983-04-27 | Bp Chem Int Ltd | Formic acid |
| DE3428319A1 (de) | 1984-08-01 | 1986-02-13 | Hüls AG, 4370 Marl | Verfahren zur gewinnung wasserfreier bzw. weitgehendwasserfreier ameisensaeure |
| GB8424672D0 (en) | 1984-09-29 | 1984-11-07 | Bp Chem Int Ltd | Production of formic acid |
| DE4211141A1 (de) | 1992-04-03 | 1993-10-07 | Basf Ag | Verfahren zur Herstellung von Ameisensäure durch thermische Spaltung von quartären Ammoniumformiaten |
| KR20090123972A (ko) | 2007-03-23 | 2009-12-02 | 바스프 에스이 | 포름산의 제조 방법 |
| US8361280B2 (en) | 2008-11-24 | 2013-01-29 | Basf Se | Process for distillatively obtaining pure 1,3-butadiene from crude 1,3-butadiene |
-
2011
- 2011-06-28 WO PCT/EP2011/060770 patent/WO2012000964A1/de active Application Filing
- 2011-06-28 JP JP2013517239A patent/JP2013533869A/ja not_active Withdrawn
- 2011-06-28 EP EP11728826.6A patent/EP2588440A1/de not_active Withdrawn
- 2011-06-28 BR BR112012032211A patent/BR112012032211A2/pt not_active IP Right Cessation
- 2011-06-28 CA CA2801580A patent/CA2801580A1/en not_active Abandoned
- 2011-06-28 KR KR1020137002200A patent/KR20130088838A/ko not_active Application Discontinuation
- 2011-06-28 SG SG2012090742A patent/SG186264A1/en unknown
- 2011-06-28 RU RU2013103601/04A patent/RU2013103601A/ru not_active Application Discontinuation
- 2011-06-28 CN CN201180031930.8A patent/CN102958894B/zh not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101006038A (zh) * | 2004-08-23 | 2007-07-25 | 巴斯福股份公司 | 制备甲酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2801580A1 (en) | 2012-01-05 |
| RU2013103601A (ru) | 2014-08-10 |
| BR112012032211A2 (pt) | 2016-11-29 |
| WO2012000964A1 (de) | 2012-01-05 |
| CN102958894A (zh) | 2013-03-06 |
| SG186264A1 (en) | 2013-01-30 |
| EP2588440A1 (de) | 2013-05-08 |
| KR20130088838A (ko) | 2013-08-08 |
| JP2013533869A (ja) | 2013-08-29 |
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