DE2005309C3 - Verfahren zur Herstellung von 1,3-Cyclohexylendiisocyanaten - Google Patents
Verfahren zur Herstellung von 1,3-CyclohexylendiisocyanatenInfo
- Publication number
- DE2005309C3 DE2005309C3 DE2005309A DE2005309A DE2005309C3 DE 2005309 C3 DE2005309 C3 DE 2005309C3 DE 2005309 A DE2005309 A DE 2005309A DE 2005309 A DE2005309 A DE 2005309A DE 2005309 C3 DE2005309 C3 DE 2005309C3
- Authority
- DE
- Germany
- Prior art keywords
- phosgene
- amine
- mixture
- equivalent
- temperature
- 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
- 238000000034 method Methods 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 30
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 30
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 28
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 21
- 239000008096 xylene Substances 0.000 claims description 21
- 150000004985 diamines Chemical class 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 10
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical class NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 7
- GNQKHBSIBXSFFD-UHFFFAOYSA-N 1,3-diisocyanatocyclohexane Chemical compound O=C=NC1CCCC(N=C=O)C1 GNQKHBSIBXSFFD-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 150000004984 aromatic diamines Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 12
- 125000005442 diisocyanate group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- GQWWGRUJOCIUKI-UHFFFAOYSA-N 2-[3-(2-methyl-1-oxopyrrolo[1,2-a]pyrazin-3-yl)propyl]guanidine Chemical compound O=C1N(C)C(CCCN=C(N)N)=CN2C=CC=C21 GQWWGRUJOCIUKI-UHFFFAOYSA-N 0.000 description 6
- OHTRJOZKRSVAOX-UHFFFAOYSA-N 1,3-diisocyanato-2-methylcyclohexane Chemical compound CC1C(N=C=O)CCCC1N=C=O OHTRJOZKRSVAOX-UHFFFAOYSA-N 0.000 description 5
- QTKDDPSHNLZGRO-UHFFFAOYSA-N 4-methylcyclohexane-1,3-diamine Chemical compound CC1CCC(N)CC1N QTKDDPSHNLZGRO-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- KHBBRIBQJGWUOW-UHFFFAOYSA-N 2-methylcyclohexane-1,3-diamine Chemical compound CC1C(N)CCCC1N KHBBRIBQJGWUOW-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical class NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance 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
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-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
- JJHBVKAOMKUSFZ-UHFFFAOYSA-N 2,4-dimethylcyclohexane-1,3-diamine Chemical compound CC1CCC(N)C(C)C1N JJHBVKAOMKUSFZ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- RHOFEWUVGDROTG-UHFFFAOYSA-N CC1C(CC(CC1C)N)N Chemical compound CC1C(CC(CC1C)N)N RHOFEWUVGDROTG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- -1 aliphatic diamines Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- GKJROTAYDAJLGD-UHFFFAOYSA-N carbonyl dichloride;hydrochloride Chemical compound Cl.ClC(Cl)=O GKJROTAYDAJLGD-UHFFFAOYSA-N 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79693369A | 1969-02-05 | 1969-02-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2005309A1 DE2005309A1 (de) | 1970-08-13 |
| DE2005309B2 DE2005309B2 (de) | 1975-04-17 |
| DE2005309C3 true DE2005309C3 (de) | 1975-11-27 |
Family
ID=25169430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2005309A Expired DE2005309C3 (de) | 1969-02-05 | 1970-02-05 | Verfahren zur Herstellung von 1,3-Cyclohexylendiisocyanaten |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3631092A (OSRAM) |
| BE (1) | BE745439A (OSRAM) |
| DE (1) | DE2005309C3 (OSRAM) |
| FR (1) | FR2032755A5 (OSRAM) |
| GB (1) | GB1275547A (OSRAM) |
| NL (1) | NL7001475A (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3960916A (en) * | 1975-01-24 | 1976-06-01 | Basf Aktiengesellschaft | Manufacture of organic isocyanates |
| DE4412327A1 (de) * | 1994-04-11 | 1995-10-12 | Bayer Ag | Verfahren zur Herstellung von Diisocyanaten |
| DE10261187A1 (de) * | 2002-12-20 | 2004-07-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| US20070232827A1 (en) * | 2004-05-25 | 2007-10-04 | Basf Aktiengesellschaft | Isocyanate Production Method |
| EP2681189A1 (de) | 2011-03-03 | 2014-01-08 | Basf Se | Verfahren zur herstellung von biuretgruppenhaltigen polyisocyanaten |
| US8609887B2 (en) | 2011-03-03 | 2013-12-17 | Basf Se | Process for preparing polyisocyanates comprising biuret groups |
| EP3325441A1 (de) * | 2015-07-21 | 2018-05-30 | Basf Se | Verfahren zur herstellung eines cyclischen isocyanates |
| CN108752240A (zh) * | 2018-07-13 | 2018-11-06 | 江苏快达农化股份有限公司 | 一种1,3-二甲基异氰酸酯环己烷的合成方法 |
| CN109053493B (zh) * | 2018-09-13 | 2020-12-15 | 浙江丽水有邦新材料有限公司 | 甲基环己基二异氰酸酯制备方法 |
-
1969
- 1969-02-05 US US796933A patent/US3631092A/en not_active Expired - Lifetime
-
1970
- 1970-01-28 GB GB4197/70A patent/GB1275547A/en not_active Expired
- 1970-02-02 NL NL7001475A patent/NL7001475A/xx not_active Application Discontinuation
- 1970-02-04 BE BE745439D patent/BE745439A/xx unknown
- 1970-02-05 FR FR7004077A patent/FR2032755A5/fr not_active Expired
- 1970-02-05 DE DE2005309A patent/DE2005309C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2005309B2 (de) | 1975-04-17 |
| BE745439A (fr) | 1970-08-04 |
| DE2005309A1 (de) | 1970-08-13 |
| NL7001475A (OSRAM) | 1970-08-07 |
| GB1275547A (en) | 1972-05-24 |
| US3631092A (en) | 1971-12-28 |
| FR2032755A5 (OSRAM) | 1970-11-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0597361B1 (de) | Verfahren zur Herstellung von Dinitrotoluol | |
| DE3212510C2 (OSRAM) | ||
| DE2005309C3 (de) | Verfahren zur Herstellung von 1,3-Cyclohexylendiisocyanaten | |
| DE4309140C2 (de) | Verfahren zur Herstellung von Dinitrotoluol | |
| EP0106138A1 (de) | Verfahren zur kontinuierlichen Heissphosgenierung von Aminen | |
| EP0027941B1 (de) | Verfahren zur Herstellung von Carbonsäurehalogeniden | |
| DE2443179B2 (de) | Verfahren zur herstellung von perchlormethylbenzolen | |
| EP0845470A2 (de) | Verfahren zur kontinuierlichen Herstellung von Carbonoyloxysilanen | |
| DE1593935C3 (de) | Verfahren zur Herstellung von Polyaminen | |
| DE1123662B (de) | Verfahren zur Herstellung von Alkylbenzoldiisocyanaten | |
| DE2743610C3 (de) | Verfahren zur Herstellung von chlorsubstituierten aromatischen Aminen | |
| DE2747524A1 (de) | Verfahren und vorrichtung zur kontinuierlichen herstellung aromatischer isocyanate | |
| DE2206167C3 (de) | Herstellung von herbicid wirksamen 3-(Halogenphenyl)-1,1 -dialkylharnstoffen | |
| DE3540863C1 (en) | Process for preparing hexamethylene diisocyanate | |
| DE954873C (de) | Verfahren zur Herstellung von Diaethylisonitrosomalonat | |
| DE2819980C2 (de) | Verfahren zur Herstellung von 3(4), 8(9)-Bis-(isocyanatomethyl)-tricyclo-[5.2.1.0↑2↑↑,↑↑6↑]decanen | |
| DE2202204A1 (de) | Verfahren zur kontinuierlichen herstellung von 2-mercaptobenzimidazol | |
| DE2824648A1 (de) | Verfahren zur herstellung von isocyanaten | |
| DE2024858A1 (OSRAM) | ||
| DE2856216A1 (de) | Verfahren zur herstellung von aethern | |
| EP0014406B1 (de) | Verfahren zur Abtrennung von Selen, Selenverbindungen, Schwefel und/oder Schwefelverbindungen aus diese Elemente bzw. Verbindungen aufweisenden Urethanen | |
| DE2323299B2 (de) | Verfahren zur kontinuierlichen Herstellung von l-Isocyanato-3-(isocyanatomethyl)-33f5-trimethylcyclohexan | |
| DE2360248C3 (de) | Verfahren zur Herstellung von Estern von Thiolcarbaminsäuren | |
| DE3002826A1 (de) | Verfahren zur herstellung von (alpha)-epoxiden mit 11 bis 24 kohlenstoffatomen | |
| EP0051804A1 (de) | Verfahren zur Herstellung cyclischer Phosphazene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |