DE2806214A1 - Verfahren zur kontinuierlichen aufarbeitung von bei der phosgenierung von monoaminen anfallenden loesungen - Google Patents
Verfahren zur kontinuierlichen aufarbeitung von bei der phosgenierung von monoaminen anfallenden loesungenInfo
- Publication number
- DE2806214A1 DE2806214A1 DE19782806214 DE2806214A DE2806214A1 DE 2806214 A1 DE2806214 A1 DE 2806214A1 DE 19782806214 DE19782806214 DE 19782806214 DE 2806214 A DE2806214 A DE 2806214A DE 2806214 A1 DE2806214 A1 DE 2806214A1
- Authority
- DE
- Germany
- Prior art keywords
- carbamic acid
- column
- reaction vessel
- acid chloride
- solution
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 74
- 238000006243 chemical reaction Methods 0.000 claims description 71
- 239000002904 solvent Substances 0.000 claims description 63
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 60
- 238000004821 distillation Methods 0.000 claims description 51
- 238000010992 reflux Methods 0.000 claims description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 39
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 39
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 39
- 239000000047 product Substances 0.000 claims description 39
- 239000012948 isocyanate Substances 0.000 claims description 38
- 150000002513 isocyanates Chemical class 0.000 claims description 37
- 238000003776 cleavage reaction Methods 0.000 claims description 21
- 230000007017 scission Effects 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 238000010626 work up procedure Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 2
- 239000012263 liquid product Substances 0.000 claims description 2
- 230000005611 electricity Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 79
- 239000007789 gas Substances 0.000 description 30
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 26
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 description 18
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 238000012856 packing Methods 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 7
- 230000008030 elimination Effects 0.000 description 6
- 238000003379 elimination reaction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- PJLHXSBKGRJXHA-UHFFFAOYSA-N n-ethylcarbamoyl chloride Chemical compound CCNC(Cl)=O PJLHXSBKGRJXHA-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 amine hydrochloride Chemical class 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- RMISVOPUIFJTEO-UHFFFAOYSA-N 2,3-dichlorobutane Chemical class CC(Cl)C(C)Cl RMISVOPUIFJTEO-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000008096 xylene 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
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782806214 DE2806214A1 (de) | 1978-02-14 | 1978-02-14 | Verfahren zur kontinuierlichen aufarbeitung von bei der phosgenierung von monoaminen anfallenden loesungen |
| EP79100302A EP0003570B1 (de) | 1978-02-14 | 1979-02-02 | Verfahren zur kontinuierlichen Aufarbeitung von bei der Phosgenierung von Monoaminen anfallenden Lösungen |
| DE7979100302T DE2960007D1 (en) | 1978-02-14 | 1979-02-02 | Process for continuously working up solutions produced by phosgenating monoamines |
| US06/010,650 US4195032A (en) | 1978-02-14 | 1979-02-09 | Process for continuously working up solutions of the type accumulating in the phosgenation of monoamines |
| CA321,215A CA1111058A (en) | 1978-02-14 | 1979-02-09 | Process for continuously working up solutions of the type accumulating in the phosgenation of monoamines |
| JP1440879A JPS54117424A (en) | 1978-02-14 | 1979-02-13 | Method of continuously finishing accumulation type solution while phosgenizing monoamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782806214 DE2806214A1 (de) | 1978-02-14 | 1978-02-14 | Verfahren zur kontinuierlichen aufarbeitung von bei der phosgenierung von monoaminen anfallenden loesungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2806214A1 true DE2806214A1 (de) | 1979-08-16 |
Family
ID=6031935
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782806214 Withdrawn DE2806214A1 (de) | 1978-02-14 | 1978-02-14 | Verfahren zur kontinuierlichen aufarbeitung von bei der phosgenierung von monoaminen anfallenden loesungen |
| DE7979100302T Expired DE2960007D1 (en) | 1978-02-14 | 1979-02-02 | Process for continuously working up solutions produced by phosgenating monoamines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE7979100302T Expired DE2960007D1 (en) | 1978-02-14 | 1979-02-02 | Process for continuously working up solutions produced by phosgenating monoamines |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4195032A (enExample) |
| EP (1) | EP0003570B1 (enExample) |
| JP (1) | JPS54117424A (enExample) |
| CA (1) | CA1111058A (enExample) |
| DE (2) | DE2806214A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2549671B2 (ja) | 1987-09-09 | 1996-10-30 | ユニチカ株式会社 | ポリエステル細幅織物 |
| DE4137428A1 (de) * | 1991-11-14 | 1993-05-19 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten |
| DE10260027A1 (de) * | 2002-12-19 | 2004-07-08 | Basf Ag | Verfahren zur Abtrennung und Reinigung von Lösungsmittel von einem Reaktionsgemisch aus einer Isocyanatsynthese |
| CN102659631B (zh) * | 2011-12-24 | 2014-05-07 | 德州绿邦化工有限公司 | 一步合成乙基异氰酸酯的方法 |
| CN106715385B (zh) * | 2014-09-19 | 2020-04-14 | 科思创德国股份有限公司 | 在气相中制备异氰酸酯的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1047215A (enExample) * | 1963-07-12 | |||
| DE2411441A1 (de) * | 1974-03-11 | 1975-10-02 | Basf Ag | Verfahren zur herstellung von alkylisocyanaten |
| DE2411442A1 (de) * | 1974-03-11 | 1975-10-02 | Basf Ag | Verfahren zur herstellung von aliphatischen isocyanaten |
| DE2422211A1 (de) * | 1974-05-08 | 1975-11-27 | Basf Ag | Verfahren zur herstellung von alkylisocyanaten |
| DE2503270C2 (de) * | 1975-01-28 | 1983-06-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von aliphatischen Isocyanaten |
| US4082787A (en) * | 1977-01-03 | 1978-04-04 | E. I. Du Pont De Nemours And Company | Methyl isocyanate process |
-
1978
- 1978-02-14 DE DE19782806214 patent/DE2806214A1/de not_active Withdrawn
-
1979
- 1979-02-02 DE DE7979100302T patent/DE2960007D1/de not_active Expired
- 1979-02-02 EP EP79100302A patent/EP0003570B1/de not_active Expired
- 1979-02-09 CA CA321,215A patent/CA1111058A/en not_active Expired
- 1979-02-09 US US06/010,650 patent/US4195032A/en not_active Expired - Lifetime
- 1979-02-13 JP JP1440879A patent/JPS54117424A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4195032A (en) | 1980-03-25 |
| JPS6160824B2 (enExample) | 1986-12-23 |
| CA1111058A (en) | 1981-10-20 |
| DE2960007D1 (en) | 1980-11-13 |
| EP0003570B1 (de) | 1980-07-23 |
| JPS54117424A (en) | 1979-09-12 |
| EP0003570A1 (de) | 1979-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |