JPS6236507B2 - - Google Patents
Info
- Publication number
- JPS6236507B2 JPS6236507B2 JP55046987A JP4698780A JPS6236507B2 JP S6236507 B2 JPS6236507 B2 JP S6236507B2 JP 55046987 A JP55046987 A JP 55046987A JP 4698780 A JP4698780 A JP 4698780A JP S6236507 B2 JPS6236507 B2 JP S6236507B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- formic acid
- extractant
- distillation
- hydrolysis
- 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 156
- 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 description 79
- 235000019253 formic acid Nutrition 0.000 claims abstract description 78
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims abstract description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 57
- 230000007062 hydrolysis Effects 0.000 claims abstract description 39
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 39
- 238000004821 distillation Methods 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 238000000605 extraction Methods 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000622 liquid--liquid extraction Methods 0.000 abstract description 3
- 238000000638 solvent extraction Methods 0.000 abstract description 3
- 239000012071 phase Substances 0.000 description 12
- 238000000926 separation method Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000006257 total synthesis reaction Methods 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000895 extractive distillation Methods 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000011017 operating method Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- QQGNLKJAIVSNCO-UHFFFAOYSA-N N-butylformamide Chemical compound CCCCNC=O QQGNLKJAIVSNCO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000007630 basic procedure Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- HQVFCQRVQFYGRJ-UHFFFAOYSA-N formic acid;hydrate Chemical compound O.OC=O HQVFCQRVQFYGRJ-UHFFFAOYSA-N 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Chemical group 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000002032 methanolic fraction Substances 0.000 description 1
- NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 1
- FWHFWYKSIPTXBJ-UHFFFAOYSA-N n-butyl-n-cyclohexylformamide Chemical compound CCCCN(C=O)C1CCCCC1 FWHFWYKSIPTXBJ-UHFFFAOYSA-N 0.000 description 1
- HPWNCPYWUHXVNZ-UHFFFAOYSA-N n-butyl-n-ethylheptanamide Chemical compound CCCCCCC(=O)N(CC)CCCC HPWNCPYWUHXVNZ-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- LYELEANKTIGQME-UHFFFAOYSA-N n-heptan-2-yl-n-methylformamide Chemical compound CCCCCC(C)N(C)C=O LYELEANKTIGQME-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 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
- C07C51/09—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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792914671 DE2914671A1 (de) | 1979-04-11 | 1979-04-11 | Verfahren zur gewinnung von wasserfreier oder weitgehend wasserfreier ameisensaeure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS568341A JPS568341A (en) | 1981-01-28 |
| JPS6236507B2 true JPS6236507B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-08-07 |
Family
ID=6068072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4698780A Granted JPS568341A (en) | 1979-04-11 | 1980-04-11 | Manufacture of noowater or almost noowater formic acid |
Country Status (10)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS585895B2 (ja) * | 1980-07-17 | 1983-02-02 | 日本ソレツクス株式会社 | 有機酸の分離方法 |
| NL8103517A (nl) * | 1981-07-24 | 1983-02-16 | Badger Bv | Werkwijze voor het scheiden van carbonzuren van mengsels met niet-zuren door een absorptie-stripbehandeling. |
| DE3319651A1 (de) * | 1983-05-31 | 1984-12-06 | Basf Ag, 6700 Ludwigshafen | Verfahren zur destillativen gewinnung von ameisensaeure |
| DE3411384A1 (de) * | 1984-03-28 | 1985-10-10 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von wasserfreier oder weitgehend wasserfreier ameisensaeure durch hydrolyse von methylformiat |
| DE3417790A1 (de) * | 1984-05-14 | 1985-11-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ameisensaeure |
| DE4211141A1 (de) * | 1992-04-03 | 1993-10-07 | Basf Ag | Verfahren zur Herstellung von Ameisensäure durch thermische Spaltung von quartären Ammoniumformiaten |
| DE4444979A1 (de) | 1994-12-16 | 1996-06-20 | Basf Ag | Verfahren und Vorrichtung zur Gewinnung von Ameisensäure |
| DE19953832A1 (de) * | 1999-11-09 | 2001-05-10 | Basf Ag | Verfahren zur Herstellung von Ameisensäure |
| DE10002790A1 (de) * | 2000-01-24 | 2001-07-26 | Basf Ag | Verfahren zur Reinigung von Abgasströmen |
| DE10002795A1 (de) * | 2000-01-24 | 2001-08-02 | Basf Ag | Werkstoff für eine Anlage zur Herstellung von wasserfreier Ameisensäure |
| DE10002793A1 (de) * | 2000-01-24 | 2001-07-26 | Basf Ag | Verwendung eines Extraktionsmittels bei der Herstellung von wasserfreier Ameisensäure |
| DE10002794A1 (de) * | 2000-01-24 | 2001-07-26 | Basf Ag | Abwasserreinigung beim Verfahren zur Herstellung von wasserfreier Ameisensäure |
| DE10002791A1 (de) * | 2000-01-24 | 2001-07-26 | Basf Ag | Verfahren zur Gewinnung von wasserfreier Ameisensäure |
| DE10237379A1 (de) * | 2002-08-12 | 2004-02-19 | Basf Ag | Verfahren und Vorrichtung zur Herstellung von ameisensauren Formiaten und deren Verwendung |
| DE10237380A1 (de) * | 2002-08-12 | 2004-02-19 | Basf Ag | Verfahren und Vorrichtung zur Herstellung von ameisensauren Formlaten und deren Verwendung |
| US7495232B2 (en) * | 2003-10-16 | 2009-02-24 | Alis Corporation | Ion sources, systems and methods |
| CN101544558B (zh) * | 2008-03-24 | 2014-05-07 | 四川省达科特能源科技有限公司 | 从含水甲酸中分离精制得到高纯度甲酸的方法 |
| US8138371B2 (en) * | 2009-03-11 | 2012-03-20 | Biofine Technologies Llc | Production of formic acid |
| EP2747883B1 (en) | 2011-08-27 | 2017-02-15 | Taminco | Process of formic acid production by hydrolysis of methyl formate |
| US10266466B2 (en) | 2017-08-02 | 2019-04-23 | Eastman Chemical Company | Iron-catalyzed transfer hydrogenation of esters to alcohols |
| US10435349B2 (en) | 2017-08-02 | 2019-10-08 | Eastman Chemical Company | Iron-catalyzed cross-coupling of methanol with secondary or tertiary alcohols to produce formate esters |
| US10544077B2 (en) * | 2017-08-02 | 2020-01-28 | Eastman Chemical Company | Process for making formic acid utilizing higher-boiling formate esters |
| US10266467B2 (en) | 2017-08-02 | 2019-04-23 | Eastman Chemical Company | Synthesis of glycols via transfer hydrogenation of alpha-functional esters with alcohols |
| US10570081B2 (en) * | 2017-08-02 | 2020-02-25 | Eastman Chemical Company | Process for making formic acid utilizing lower-boiling formate esters |
| CN111356672B (zh) * | 2017-08-24 | 2023-06-09 | 英国石油有限公司 | 甲醇脱水方法 |
| CN114644549A (zh) * | 2022-04-24 | 2022-06-21 | 聊城市鲁西化工工程设计有限责任公司 | 一种甲酸的生产系统及生产工艺 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2160064A (en) * | 1936-06-17 | 1939-05-30 | Carbide & Carbon Chem Corp | Manufacture of formic acid |
| NL7501253A (nl) * | 1974-02-15 | 1975-08-19 | Basf Ag | Werkwijze voor het winnen van mierezuur. |
| US4217460A (en) * | 1975-10-11 | 1980-08-12 | Basf Aktiengesellschaft | Isolation of formic acid from its aqueous solutions |
| DE2545730A1 (de) * | 1975-10-11 | 1977-04-21 | Basf Ag | Verfahren zur reindarstellung von ameisensaeure |
| DE2545658C2 (de) * | 1975-10-11 | 1985-12-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung von Carbonsäuren aus ihren wäßrigen Lösungen |
| US4143066A (en) * | 1976-12-16 | 1979-03-06 | The Dow Chemical Company | Separation and recovery of carboxylic acids from water |
| DE2744313A1 (de) * | 1977-10-01 | 1979-04-12 | Basf Ag | Verfahren zur herstellung von ameisensaeure |
| DE2853991A1 (de) * | 1978-12-14 | 1980-07-03 | Basf Ag | Verfahren zur gewinnung von wasserfreier oder weitgehend wasserfreier ameisensaeure |
-
1979
- 1979-04-11 DE DE19792914671 patent/DE2914671A1/de not_active Withdrawn
-
1980
- 1980-03-18 US US06/131,501 patent/US4326073A/en not_active Expired - Lifetime
- 1980-03-24 CA CA000348294A patent/CA1135282A/en not_active Expired
- 1980-04-03 EP EP80101788A patent/EP0017866B1/de not_active Expired
- 1980-04-03 DE DE8080101788T patent/DE3060960D1/de not_active Expired
- 1980-04-03 AT AT80101788T patent/ATE1670T1/de not_active IP Right Cessation
- 1980-04-10 ES ES490435A patent/ES490435A0/es active Granted
- 1980-04-10 NO NO801034A patent/NO152371C/no unknown
- 1980-04-10 ZA ZA00802156A patent/ZA802156B/xx unknown
- 1980-04-10 AU AU57296/80A patent/AU528657B2/en not_active Expired
- 1980-04-11 JP JP4698780A patent/JPS568341A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3060960D1 (en) | 1982-11-25 |
| AU5729680A (en) | 1980-10-16 |
| CA1135282A (en) | 1982-11-09 |
| DE2914671A1 (de) | 1980-10-23 |
| ZA802156B (en) | 1981-05-27 |
| EP0017866A1 (de) | 1980-10-29 |
| US4326073A (en) | 1982-04-20 |
| JPS568341A (en) | 1981-01-28 |
| ATE1670T1 (de) | 1982-11-15 |
| ES8101032A1 (es) | 1980-12-01 |
| NO801034L (no) | 1980-10-13 |
| NO152371B (no) | 1985-06-10 |
| AU528657B2 (en) | 1983-05-05 |
| EP0017866B1 (de) | 1982-10-20 |
| NO152371C (no) | 1985-09-18 |
| ES490435A0 (es) | 1980-12-01 |
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