DE1620416A1 - Verfahren zur Herstellung organischer Verbindungen - Google Patents
Verfahren zur Herstellung organischer VerbindungenInfo
- Publication number
- DE1620416A1 DE1620416A1 DE19661620416 DE1620416A DE1620416A1 DE 1620416 A1 DE1620416 A1 DE 1620416A1 DE 19661620416 DE19661620416 DE 19661620416 DE 1620416 A DE1620416 A DE 1620416A DE 1620416 A1 DE1620416 A1 DE 1620416A1
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- acid
- carbonate
- phosgene
- acids
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 8
- 150000002894 organic compounds Chemical class 0.000 title description 4
- 239000002253 acid Substances 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 42
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 20
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000002452 interceptive effect Effects 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 235000015961 tonic Nutrition 0.000 claims 1
- 230000001256 tonic effect Effects 0.000 claims 1
- 229960000716 tonics Drugs 0.000 claims 1
- -1 aromatic nitrile carbonates Chemical class 0.000 description 29
- 150000007513 acids Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 8
- 229920005554 polynitrile Polymers 0.000 description 8
- 150000002513 isocyanates Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JRZGPWOEHDOVMC-UHFFFAOYSA-N n-hydroxynaphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)NO)=CC=CC2=C1 JRZGPWOEHDOVMC-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- XWMRVKXQSJXBGI-UHFFFAOYSA-N N-hydroxy-2-[2-[2-(hydroxycarbamoyl)phenyl]ethenyl]benzamide Chemical compound ONC(=O)C1=CC=CC=C1C=CC1=CC=CC=C1C(=O)NO XWMRVKXQSJXBGI-UHFFFAOYSA-N 0.000 description 1
- UOGKTULGNUUXIH-UHFFFAOYSA-N N-hydroxy-4-[2-[4-(hydroxycarbamoyl)phenyl]ethenyl]benzamide Chemical compound ONC(=O)C1=CC=C(C=CC2=CC=C(C=C2)C(=O)NO)C=C1 UOGKTULGNUUXIH-UHFFFAOYSA-N 0.000 description 1
- JNSXPMAVEOYORD-UHFFFAOYSA-N N-hydroxy-4-[4-(hydroxycarbamoyl)phenyl]benzamide Chemical compound C1(=CC=C(C=C1)C(=O)NO)C1=CC=C(C=C1)C(=O)NO JNSXPMAVEOYORD-UHFFFAOYSA-N 0.000 description 1
- NBENGDWLBHDYRM-UHFFFAOYSA-N N-hydroxyanthracene-1-carboxamide Chemical class C1(=CC=CC2=CC3=CC=CC=C3C=C12)C(=O)NO NBENGDWLBHDYRM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- IPSXSYBAGOIBHX-UHFFFAOYSA-N carbonic acid 1,2,3,4-tetrahydronaphthalene-1-carbonitrile Chemical compound C(O)(O)=O.C1(CCCC2=CC=CC=C12)C#N IPSXSYBAGOIBHX-UHFFFAOYSA-N 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- MZNLBWFDYYLBPE-UHFFFAOYSA-N n-hydroxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)NO)CCCC2=C1 MZNLBWFDYYLBPE-UHFFFAOYSA-N 0.000 description 1
- ZHSDLNXUORTYIN-UHFFFAOYSA-N n-hydroxy-2-phenylbenzamide Chemical class ONC(=O)C1=CC=CC=C1C1=CC=CC=C1 ZHSDLNXUORTYIN-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000003960 organic solvent 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
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/08—Preparation of derivatives of isocyanic acid from or via heterocyclic compounds, e.g. pyrolysis of furoxans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50261665A | 1965-10-22 | 1965-10-22 | |
| US50245065A | 1965-10-22 | 1965-10-22 | |
| US50262065A | 1965-10-22 | 1965-10-22 | |
| US50234765A | 1965-10-22 | 1965-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620416A1 true DE1620416A1 (de) | 1970-03-12 |
Family
ID=27504428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620416 Pending DE1620416A1 (de) | 1965-10-22 | 1966-10-22 | Verfahren zur Herstellung organischer Verbindungen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE688748A (enrdf_load_stackoverflow) |
| DE (1) | DE1620416A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1505468A (enrdf_load_stackoverflow) |
| GB (1) | GB1155104A (enrdf_load_stackoverflow) |
| NL (1) | NL6615004A (enrdf_load_stackoverflow) |
-
1966
- 1966-10-21 BE BE688748D patent/BE688748A/xx unknown
- 1966-10-21 GB GB4715066A patent/GB1155104A/en not_active Expired
- 1966-10-22 FR FR81257A patent/FR1505468A/fr not_active Expired
- 1966-10-22 NL NL6615004A patent/NL6615004A/xx unknown
- 1966-10-22 DE DE19661620416 patent/DE1620416A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1155104A (en) | 1969-06-18 |
| BE688748A (enrdf_load_stackoverflow) | 1967-04-21 |
| NL6615004A (enrdf_load_stackoverflow) | 1967-04-24 |
| FR1505468A (fr) | 1967-12-15 |
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