KR20180030035A - 이소시아네이트를 제조하는 방법 - Google Patents
이소시아네이트를 제조하는 방법 Download PDFInfo
- Publication number
- KR20180030035A KR20180030035A KR1020187000939A KR20187000939A KR20180030035A KR 20180030035 A KR20180030035 A KR 20180030035A KR 1020187000939 A KR1020187000939 A KR 1020187000939A KR 20187000939 A KR20187000939 A KR 20187000939A KR 20180030035 A KR20180030035 A KR 20180030035A
- Authority
- KR
- South Korea
- Prior art keywords
- phosgene
- stream
- distillation column
- vapor
- phase
- 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- Withdrawn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
- 239000012948 isocyanate Substances 0.000 title claims abstract description 38
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title abstract description 31
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 229
- 238000000034 method Methods 0.000 claims abstract description 111
- 238000006243 chemical reaction Methods 0.000 claims abstract description 70
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract 3
- 238000004821 distillation Methods 0.000 claims description 78
- 230000008569 process Effects 0.000 claims description 73
- 239000007788 liquid Substances 0.000 claims description 62
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 60
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 60
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 60
- 239000002904 solvent Substances 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 51
- 238000010521 absorption reaction Methods 0.000 claims description 24
- 230000008859 change Effects 0.000 claims description 23
- 230000008016 vaporization Effects 0.000 claims description 23
- 238000009835 boiling Methods 0.000 claims description 15
- 238000004064 recycling Methods 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 238000012805 post-processing Methods 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 2
- 239000012071 phase Substances 0.000 abstract description 35
- 239000007792 gaseous phase Substances 0.000 abstract description 6
- 239000007789 gas Substances 0.000 description 60
- 239000000047 product Substances 0.000 description 36
- 238000005201 scrubbing Methods 0.000 description 29
- 238000009833 condensation Methods 0.000 description 22
- 230000005494 condensation Effects 0.000 description 22
- 238000009834 vaporization Methods 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 16
- 238000000926 separation method Methods 0.000 description 16
- 238000001816 cooling Methods 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000011261 inert gas Substances 0.000 description 10
- 230000014759 maintenance of location Effects 0.000 description 9
- 238000010791 quenching Methods 0.000 description 9
- 230000000171 quenching effect Effects 0.000 description 9
- 239000006200 vaporizer Substances 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000010574 gas phase reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000033228 biological regulation Effects 0.000 description 7
- GKJROTAYDAJLGD-UHFFFAOYSA-N carbonyl dichloride;hydrochloride Chemical compound Cl.ClC(Cl)=O GKJROTAYDAJLGD-UHFFFAOYSA-N 0.000 description 7
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000010276 construction Methods 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 230000010354 integration Effects 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 230000008719 thickening Effects 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000008246 gaseous mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000002918 waste heat Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- -1 amine hydrochloride Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/16—Fractionating columns in which vapour bubbles through liquid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/42—Regulation; Control
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
- C07C263/20—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00033—Continuous processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15176964 | 2015-07-16 | ||
| EP15176964.3 | 2015-07-16 | ||
| PCT/EP2016/066474 WO2017009311A1 (de) | 2015-07-16 | 2016-07-12 | Verfahren zur herstellung von isocyanaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20180030035A true KR20180030035A (ko) | 2018-03-21 |
Family
ID=53682542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020187000939A Withdrawn KR20180030035A (ko) | 2015-07-16 | 2016-07-12 | 이소시아네이트를 제조하는 방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10239826B2 (enExample) |
| EP (1) | EP3322692B1 (enExample) |
| JP (1) | JP6804512B2 (enExample) |
| KR (1) | KR20180030035A (enExample) |
| CN (1) | CN107848960B (enExample) |
| HU (1) | HUE047039T2 (enExample) |
| WO (1) | WO2017009311A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022146088A1 (ko) * | 2020-12-30 | 2022-07-07 | 한화솔루션 주식회사 | 이소시아네이트 화합물의 제조 방법 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3524591A1 (en) | 2018-02-13 | 2019-08-14 | Covestro Deutschland AG | Process for the preparation of isocyanates |
| US10626084B2 (en) | 2018-08-03 | 2020-04-21 | Covestro Llc | Method for producing two isocyanates |
| WO2025065554A1 (zh) * | 2023-09-28 | 2025-04-03 | 万华化学集团股份有限公司 | 低卤代脂肪环烃物质含量聚合mdi及其制备方法和应用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2764607A (en) | 1952-07-26 | 1956-09-25 | Celanese Corp | Recovery of phosgene in the production of chloroformates |
| GB737442A (en) | 1952-12-19 | 1955-09-28 | Bayer Ag | Recovery of phosgene |
| FR1469105A (fr) | 1965-12-27 | 1967-02-10 | Toulousaine De Prod Chim Toloc | Procédé de fabrication d'esters isocyaniques |
| DE4217019A1 (de) | 1992-05-22 | 1993-11-25 | Bayer Ag | Verfahren zur Herstellung von aromatischen Diisocyanaten |
| DE19523385A1 (de) | 1995-06-23 | 1997-01-09 | Bayer Ag | Verfahren zur Herstellung von Triisocyanaten |
| DE10027779A1 (de) * | 2000-06-07 | 2001-12-13 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| DE10222968A1 (de) * | 2002-05-23 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| EP1371633A1 (en) | 2002-06-14 | 2003-12-17 | Bayer Ag | Process for the purification of mixtures of toluenediisocyanate incorporating a dividing-wall distillation column |
| DE10245704A1 (de) | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zum Quenchen eines gasförmigen Reaktionsgemisches bei der Gasphasenphosgenierung von Diaminen |
| DE10260084A1 (de) | 2002-12-19 | 2004-07-01 | Basf Ag | Auftrennung eines Stoffgemisches aus Clorwasserstoff und Phosgen |
| DE102005036870A1 (de) | 2005-08-02 | 2007-02-08 | Bayer Materialscience Ag | Verfahren zur Gasphasenphosgenierung |
| DE102005037328A1 (de) | 2005-08-04 | 2007-02-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| CN102850239B (zh) | 2007-01-17 | 2014-07-02 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| WO2009037179A1 (de) | 2007-09-19 | 2009-03-26 | Basf Se | Verfahren zur herstellung von isocyanaten |
| DE102008009761A1 (de) * | 2008-02-19 | 2009-08-27 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten |
| DE102008061686A1 (de) | 2008-12-11 | 2010-06-17 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE102009032413A1 (de) | 2009-07-09 | 2011-01-13 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten |
| KR101869117B1 (ko) * | 2010-10-14 | 2018-06-19 | 바스프 에스이 | 이소시아네이트를 제조하는 방법 |
-
2016
- 2016-07-12 JP JP2018501949A patent/JP6804512B2/ja active Active
- 2016-07-12 HU HUE16736892A patent/HUE047039T2/hu unknown
- 2016-07-12 KR KR1020187000939A patent/KR20180030035A/ko not_active Withdrawn
- 2016-07-12 WO PCT/EP2016/066474 patent/WO2017009311A1/de not_active Ceased
- 2016-07-12 EP EP16736892.7A patent/EP3322692B1/de active Active
- 2016-07-12 US US15/744,239 patent/US10239826B2/en active Active
- 2016-07-12 CN CN201680041927.7A patent/CN107848960B/zh active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022146088A1 (ko) * | 2020-12-30 | 2022-07-07 | 한화솔루션 주식회사 | 이소시아네이트 화합물의 제조 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107848960A (zh) | 2018-03-27 |
| WO2017009311A1 (de) | 2017-01-19 |
| EP3322692B1 (de) | 2019-07-03 |
| EP3322692A1 (de) | 2018-05-23 |
| CN107848960B (zh) | 2020-09-22 |
| US20180194720A1 (en) | 2018-07-12 |
| US10239826B2 (en) | 2019-03-26 |
| HUE047039T2 (hu) | 2020-04-28 |
| JP6804512B2 (ja) | 2020-12-23 |
| JP2018520186A (ja) | 2018-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20180111 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination |