CA2209754A1 - Process for the distillative purification of diurethanes - Google Patents
Process for the distillative purification of diurethanesInfo
- Publication number
- CA2209754A1 CA2209754A1 CA002209754A CA2209754A CA2209754A1 CA 2209754 A1 CA2209754 A1 CA 2209754A1 CA 002209754 A CA002209754 A CA 002209754A CA 2209754 A CA2209754 A CA 2209754A CA 2209754 A1 CA2209754 A1 CA 2209754A1
- Authority
- CA
- Canada
- Prior art keywords
- diurethanes
- formula
- carbon atoms
- boiling
- low
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000000746 purification Methods 0.000 title claims abstract description 9
- 238000009835 boiling Methods 0.000 claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 150000001298 alcohols Chemical class 0.000 claims abstract description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 238000004821 distillation Methods 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 2
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 2
- 239000005700 Putrescine Substances 0.000 claims 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-O aminomethylcyclohexane Chemical compound [NH3+]CC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-O 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 38
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- 235000013350 formula milk Nutrition 0.000 description 25
- -1 aliphatic hydrocarbon radical Chemical class 0.000 description 20
- 230000000875 corresponding effect Effects 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 5
- 239000012159 carrier gas Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 102220347004 c.89G>A Human genes 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- OYQYHJRSHHYEIG-UHFFFAOYSA-N ethyl carbamate;urea Chemical class NC(N)=O.CCOC(N)=O OYQYHJRSHHYEIG-UHFFFAOYSA-N 0.000 description 1
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical class CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/08—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19627906A DE19627906A1 (de) | 1996-07-11 | 1996-07-11 | Verfahren zur destillativen Reinigung von Diurethanen |
| DE19627906.2 | 1996-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2209754A1 true CA2209754A1 (en) | 1998-01-11 |
Family
ID=7799515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002209754A Abandoned CA2209754A1 (en) | 1996-07-11 | 1997-07-07 | Process for the distillative purification of diurethanes |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0818441B1 (enrdf_load_html_response) |
| JP (1) | JP4119503B2 (enrdf_load_html_response) |
| CA (1) | CA2209754A1 (enrdf_load_html_response) |
| DE (2) | DE19627906A1 (enrdf_load_html_response) |
| ES (1) | ES2176560T3 (enrdf_load_html_response) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9056819B2 (en) | 2007-03-30 | 2015-06-16 | Asahi Kasei Chemicals Corporation | Isocyanate production process using composition containing carbamic acid ester and aromatic hydroxy compound, and composition for transfer and storage of carbamic acid ester |
| CN105143178A (zh) * | 2013-04-03 | 2015-12-09 | 三井化学株式会社 | 苯二甲撑二氨基甲酸酯、苯二甲撑二异氰酸酯的制造方法、苯二甲撑二异氰酸酯、及苯二甲撑二氨基甲酸酯的保存方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4141402A1 (de) * | 1991-12-16 | 1993-06-17 | Bayer Ag | Verfahren zur herstellung von hochreinen aromatischen di- und/oder polyurethanen |
| DE19523386A1 (de) * | 1995-06-23 | 1997-01-09 | Bayer Ag | Verfahren zur Entfernung von Nebenprodukten aus Diurethanen |
-
1996
- 1996-07-11 DE DE19627906A patent/DE19627906A1/de not_active Withdrawn
-
1997
- 1997-06-30 DE DE59707130T patent/DE59707130D1/de not_active Expired - Lifetime
- 1997-06-30 ES ES97110632T patent/ES2176560T3/es not_active Expired - Lifetime
- 1997-06-30 EP EP97110632A patent/EP0818441B1/de not_active Expired - Lifetime
- 1997-07-07 CA CA002209754A patent/CA2209754A1/en not_active Abandoned
- 1997-07-09 JP JP19801097A patent/JP4119503B2/ja not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9056819B2 (en) | 2007-03-30 | 2015-06-16 | Asahi Kasei Chemicals Corporation | Isocyanate production process using composition containing carbamic acid ester and aromatic hydroxy compound, and composition for transfer and storage of carbamic acid ester |
| US9637445B2 (en) | 2007-03-30 | 2017-05-02 | Asahi Kasei Chemicals Corporation | Isocyanate production process using composition containing carbamic acid ester and aromatic hydroxy compound, and composition for transfer and storage of carbamic acid ester |
| CN105143178A (zh) * | 2013-04-03 | 2015-12-09 | 三井化学株式会社 | 苯二甲撑二氨基甲酸酯、苯二甲撑二异氰酸酯的制造方法、苯二甲撑二异氰酸酯、及苯二甲撑二氨基甲酸酯的保存方法 |
| US9624165B2 (en) | 2013-04-03 | 2017-04-18 | Mitsui Chemicals, Inc. | Xylylene dicarbamate, method for producing xylylene diisocyanate, xylylene diisocyanate, and method for reserving xylylene dicarbamate |
| US9856209B2 (en) | 2013-04-03 | 2018-01-02 | Mitsui Chemicals, Inc. | Xylylene dicarbamate, method for producing xylylene diisocyanate, xylylene diisocyanate, and method for reserving xylylene dicarbamate |
| CN105143178B (zh) * | 2013-04-03 | 2018-08-24 | 三井化学株式会社 | 苯二甲撑二异氰酸酯及其制造方法、和苯二甲撑二氨基甲酸酯及其保存方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59707130D1 (de) | 2002-06-06 |
| EP0818441A1 (de) | 1998-01-14 |
| ES2176560T3 (es) | 2002-12-01 |
| JPH1087598A (ja) | 1998-04-07 |
| EP0818441B1 (de) | 2002-05-02 |
| DE19627906A1 (de) | 1998-01-15 |
| JP4119503B2 (ja) | 2008-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |