HUE028076T2 - Process for the preparation of isocyanates by thermal cleavage of carbamates - Google Patents
Process for the preparation of isocyanates by thermal cleavage of carbamates Download PDFInfo
- Publication number
- HUE028076T2 HUE028076T2 HUE11700347A HUE11700347A HUE028076T2 HU E028076 T2 HUE028076 T2 HU E028076T2 HU E11700347 A HUE11700347 A HU E11700347A HU E11700347 A HUE11700347 A HU E11700347A HU E028076 T2 HUE028076 T2 HU E028076T2
- Authority
- HU
- Hungary
- Prior art keywords
- column
- carbamate
- stream
- alcohol
- inert solvent
- Prior art date
Links
- 239000012948 isocyanate Substances 0.000 title claims description 23
- 150000002513 isocyanates Chemical class 0.000 title claims description 22
- 150000004657 carbamic acid derivatives Chemical class 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000009835 boiling Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 239000012442 inert solvent Substances 0.000 claims description 15
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 238000005878 carbamate elimination reaction Methods 0.000 claims 3
- 238000003776 cleavage reaction Methods 0.000 claims 3
- 230000007017 scission Effects 0.000 claims 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 235000005911 diet Nutrition 0.000 claims 1
- 230000037213 diet Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 238000011534 incubation Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000011514 reflex Effects 0.000 claims 1
- 238000011144 upstream manufacturing Methods 0.000 claims 1
- 230000003442 weekly effect Effects 0.000 claims 1
- 238000010494 dissociation reaction Methods 0.000 description 44
- 230000005593 dissociations Effects 0.000 description 44
- 239000002904 solvent Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 150000003673 urethanes Chemical class 0.000 description 5
- -1 aliphatic isocyanates Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011552 falling film Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- UHJWZORSTYATLW-UHFFFAOYSA-N o-biphenylyl phenyl ether Natural products C=1C=CC=C(C=2C=CC=CC=2)C=1OC1=CC=CC=C1 UHJWZORSTYATLW-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000005628 tolylene group Chemical group 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical class CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PJISLFCKHOHLLP-UHFFFAOYSA-N 2-diethoxyphosphorylsulfanyl-n,n-diethylethanamine Chemical compound CCOP(=O)(OCC)SCCN(CC)CC PJISLFCKHOHLLP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- 206010011416 Croup infectious Diseases 0.000 description 1
- 241000950314 Figura Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940076134 benzene Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 201000010549 croup Diseases 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000005195 diethylbenzenes Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/04—Preparation of derivatives of isocyanic acid from or via carbamates or carbamoyl halides
-
- 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
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10151089 | 2010-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE028076T2 true HUE028076T2 (en) | 2016-11-28 |
Family
ID=43769079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE11700347A HUE028076T2 (en) | 2010-01-19 | 2011-01-18 | Process for the preparation of isocyanates by thermal cleavage of carbamates |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2526085B1 (enExample) |
| JP (1) | JP5823982B2 (enExample) |
| KR (1) | KR20120120945A (enExample) |
| CN (1) | CN102712580B (enExample) |
| BR (1) | BR112012017877A2 (enExample) |
| ES (1) | ES2552837T3 (enExample) |
| HU (1) | HUE028076T2 (enExample) |
| PL (1) | PL2526085T3 (enExample) |
| PT (1) | PT2526085E (enExample) |
| WO (1) | WO2011089098A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI430978B (zh) * | 2010-10-04 | 2014-03-21 | Asahi Kasei Chemicals Corp | 分離方法及異氰酸酯之製造方法 |
| US8933262B2 (en) | 2011-05-24 | 2015-01-13 | Basf Se | Process for preparing polyisocyanates from biomass |
| CN103848758A (zh) * | 2012-12-06 | 2014-06-11 | 中国科学院成都有机化学有限公司 | 一种催化热分解制备异氰酸酯的方法 |
| EP3797744A1 (en) | 2014-05-09 | 2021-03-31 | 3M Innovative Properties Company | Dressing with contracting layer for linear tissue sites |
| US10898217B2 (en) | 2014-05-09 | 2021-01-26 | Kci Licensing, Inc. | Dressing providing apertures with multiple orifice sizes for negative-pressure therapy |
| AU2015255726B2 (en) | 2014-05-09 | 2020-03-05 | Solventum Intellectual Properties Company | Disruptive dressing for use with negative pressure and fluid instillation |
| EP3527180B1 (en) | 2014-05-09 | 2021-01-06 | 3M Innovative Properties Company | Debriding dressing for use with negative pressure and fluid instillation |
| CN107207422B (zh) * | 2015-01-30 | 2020-12-11 | 巴斯夫欧洲公司 | 低副产物的多亚苯基多亚甲基多异氰酸酯 |
| CN110546135B (zh) * | 2017-05-15 | 2021-12-14 | 旭化成株式会社 | 异氰酸酯的制造方法 |
| EP3450424A1 (de) * | 2017-09-04 | 2019-03-06 | Covestro Deutschland AG | Verfahren zur herstellung von isocyanaten |
| EP3876885B1 (en) | 2018-11-08 | 2023-11-29 | 3M Innovative Properties Company | Wound dressing with semi-rigid support to increase disruption using perforated dressing and negative pressure wound therapy |
| WO2021111412A1 (en) | 2019-12-05 | 2021-06-10 | Kci Licensing, Inc. | Multi-layer negative pressure incisional wound therapy dressing |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3215591A1 (de) * | 1982-04-27 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen thermischen spaltung von carbamidsaeureestern |
| JPS60231640A (ja) * | 1984-05-02 | 1985-11-18 | Asahi Chem Ind Co Ltd | イソシアナ−トの連続的製法 |
| JPH02250857A (ja) * | 1989-03-23 | 1990-10-08 | Sumitomo Metal Ind Ltd | ポリイソシアネートの製造方法 |
| US5326903A (en) | 1992-01-10 | 1994-07-05 | Nippon Shokubai Co., Ltd. | Process for preparing isocyanates using sintered oxides |
| JPH05194351A (ja) * | 1992-01-22 | 1993-08-03 | Nkk Corp | イソシアネート化合物の連続的製造装置及び方法 |
| EP0795544B1 (de) * | 1996-03-15 | 2001-10-31 | Bayer Ag | Verfahren zur thermischen Spaltung von Carbamidsäureestern |
| DE19907648A1 (de) | 1999-02-23 | 2000-08-24 | Basf Ag | Verfahren zur Herstellung von Isocyanaten durch Spaltung von Urethanen |
| DE10329491A1 (de) * | 2003-07-01 | 2005-01-27 | Basf Ag | Reaktor für gas/flüssig oder gas/flüssig/fest Reaktionen |
| CN101200436A (zh) * | 2006-12-31 | 2008-06-18 | 中国科学院成都有机化学有限公司 | 连续制备1,6-六亚甲基二异氰酸酯的方法 |
| EP2265571B1 (de) | 2008-03-18 | 2015-03-04 | Basf Se | Verfahren zur herstellung von urethanen aus mono- und difunktionalen aromatischen aminen |
-
2011
- 2011-01-18 BR BR112012017877A patent/BR112012017877A2/pt not_active IP Right Cessation
- 2011-01-18 EP EP11700347.5A patent/EP2526085B1/de not_active Not-in-force
- 2011-01-18 ES ES11700347.5T patent/ES2552837T3/es active Active
- 2011-01-18 CN CN201180006310.9A patent/CN102712580B/zh not_active Expired - Fee Related
- 2011-01-18 KR KR1020127021646A patent/KR20120120945A/ko not_active Withdrawn
- 2011-01-18 PL PL11700347T patent/PL2526085T3/pl unknown
- 2011-01-18 JP JP2012549324A patent/JP5823982B2/ja not_active Expired - Fee Related
- 2011-01-18 WO PCT/EP2011/050557 patent/WO2011089098A1/de not_active Ceased
- 2011-01-18 HU HUE11700347A patent/HUE028076T2/en unknown
- 2011-01-18 PT PT117003475T patent/PT2526085E/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012017877A2 (pt) | 2016-05-03 |
| PT2526085E (pt) | 2015-11-24 |
| CN102712580B (zh) | 2014-11-26 |
| EP2526085B1 (de) | 2015-08-12 |
| JP5823982B2 (ja) | 2015-11-25 |
| PL2526085T3 (pl) | 2016-01-29 |
| ES2552837T3 (es) | 2015-12-02 |
| KR20120120945A (ko) | 2012-11-02 |
| CN102712580A (zh) | 2012-10-03 |
| WO2011089098A1 (de) | 2011-07-28 |
| JP2013517312A (ja) | 2013-05-16 |
| EP2526085A1 (de) | 2012-11-28 |
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