DE3428319C2 - - Google Patents
Info
- Publication number
- DE3428319C2 DE3428319C2 DE19843428319 DE3428319A DE3428319C2 DE 3428319 C2 DE3428319 C2 DE 3428319C2 DE 19843428319 DE19843428319 DE 19843428319 DE 3428319 A DE3428319 A DE 3428319A DE 3428319 C2 DE3428319 C2 DE 3428319C2
- Authority
- DE
- Germany
- Prior art keywords
- formic acid
- amine
- methyl formate
- water
- column
- 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 description 178
- 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 description 88
- 235000019253 formic acid Nutrition 0.000 claims description 88
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 87
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 55
- 150000001412 amines Chemical class 0.000 claims description 51
- 238000000605 extraction Methods 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 35
- 238000006460 hydrolysis reaction Methods 0.000 claims description 26
- 230000007062 hydrolysis Effects 0.000 claims description 25
- 238000004821 distillation Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 9
- 238000003776 cleavage reaction Methods 0.000 claims description 9
- 230000007017 scission Effects 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 claims description 2
- 238000010626 work up procedure Methods 0.000 claims description 2
- 238000005336 cracking Methods 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 15
- 238000000926 separation method Methods 0.000 description 15
- 239000012071 phase Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- -1 amine formate Chemical class 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Chemical compound CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000000919 ceramic Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 4
- 239000012454 non-polar solvent Substances 0.000 description 4
- 125000001477 organic nitrogen group Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000007700 distillative separation Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- QQGNLKJAIVSNCO-UHFFFAOYSA-N N-butylformamide Chemical compound CCCCNC=O QQGNLKJAIVSNCO-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000003807 solvent-free extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07C51/48—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)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843428319 DE3428319A1 (de) | 1984-08-01 | 1984-08-01 | Verfahren zur gewinnung wasserfreier bzw. weitgehendwasserfreier ameisensaeure |
| JP16783885A JPS6143133A (ja) | 1984-08-01 | 1985-07-31 | 無水の、またはほとんど無水のギ酸の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843428319 DE3428319A1 (de) | 1984-08-01 | 1984-08-01 | Verfahren zur gewinnung wasserfreier bzw. weitgehendwasserfreier ameisensaeure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3428319A1 DE3428319A1 (de) | 1986-02-13 |
| DE3428319C2 true DE3428319C2 (en, 2012) | 1987-06-25 |
Family
ID=6242084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843428319 Granted DE3428319A1 (de) | 1984-08-01 | 1984-08-01 | Verfahren zur gewinnung wasserfreier bzw. weitgehendwasserfreier ameisensaeure |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6143133A (en, 2012) |
| DE (1) | DE3428319A1 (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4023353A1 (de) * | 1990-07-23 | 1992-01-30 | Basf Ag | Verfahren zur gewinnung von carbonsaeuren aus ihren waessrigen loesungen |
| DE4211141A1 (de) * | 1992-04-03 | 1993-10-07 | Basf Ag | Verfahren zur Herstellung von Ameisensäure durch thermische Spaltung von quartären Ammoniumformiaten |
| DE10002790A1 (de) * | 2000-01-24 | 2001-07-26 | Basf Ag | Verfahren zur Reinigung von Abgasströmen |
| DE10002791A1 (de) | 2000-01-24 | 2001-07-26 | Basf Ag | Verfahren zur Gewinnung von wasserfreier Ameisensäure |
| DE10002794A1 (de) * | 2000-01-24 | 2001-07-26 | Basf Ag | Abwasserreinigung beim Verfahren zur Herstellung von wasserfreier Ameisensäure |
| KR20070053708A (ko) | 2004-08-04 | 2007-05-25 | 포움 서플라이즈 인코포레이션 | 폴리우레탄 폼에서의 반응도 변동 및 촉매 분해 |
| DE102004040789A1 (de) | 2004-08-23 | 2006-03-02 | Basf Ag | Verfahren zur Herstellung von Ameisensäure |
| UA104324C2 (ru) | 2009-06-26 | 2014-01-27 | Басф Се | Способ получения муравьиной кислоты |
| US8901350B2 (en) | 2010-06-29 | 2014-12-02 | Basf Se | Process for the preparation of formic acid |
| KR20130088838A (ko) | 2010-06-29 | 2013-08-08 | 바스프 에스이 | 포름산의 제조 방법 |
| RU2013158468A (ru) | 2011-06-09 | 2015-07-20 | Басф Се | Способ получения муравьиной кислоты |
| 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 |
| JP2015501848A (ja) | 2011-12-20 | 2015-01-19 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ギ酸の製造方法 |
| RU2014129627A (ru) | 2011-12-20 | 2016-02-10 | Басф Се | Способ получения муравьиной кислоты |
| WO2013186156A1 (en) | 2012-06-11 | 2013-12-19 | Basf Se | Process for preparing formic acid |
| US9428438B2 (en) | 2012-11-27 | 2016-08-30 | Basf Se | Process for preparing formic acid |
| EP2925715A1 (de) | 2012-11-27 | 2015-10-07 | Basf Se | Verfahren zur herstellung von ameisensäure |
| JP7372069B2 (ja) * | 2018-09-18 | 2023-10-31 | 日東電工株式会社 | ギ酸回収方法 |
| CN110124345B (zh) * | 2019-05-16 | 2024-11-19 | 江苏凯美普瑞工程技术有限公司 | 一种甲酸甲酯分离系统及甲酸甲酯分离精制工艺 |
| JP7279727B2 (ja) * | 2021-03-10 | 2023-05-23 | 株式会社豊田中央研究所 | ギ酸回収方法 |
| JPWO2022239847A1 (en, 2012) | 2021-05-14 | 2022-11-17 | ||
| WO2024106470A1 (ja) | 2022-11-16 | 2024-05-23 | Ｓｐｉｂｅｒ株式会社 | タンパク質を含む成形体を製造する方法、及びカルボン酸を回収する方法 |
-
1984
- 1984-08-01 DE DE19843428319 patent/DE3428319A1/de active Granted
-
1985
- 1985-07-31 JP JP16783885A patent/JPS6143133A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3428319A1 (de) | 1986-02-13 |
| JPS6143133A (ja) | 1986-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |