DE1200275B - Verfahren zur Perchlorierung der Seitenketten in Methylbenzolen und deren kernsubstituierten Derivaten - Google Patents
Verfahren zur Perchlorierung der Seitenketten in Methylbenzolen und deren kernsubstituierten DerivatenInfo
- Publication number
- DE1200275B DE1200275B DER34479A DER0034479A DE1200275B DE 1200275 B DE1200275 B DE 1200275B DE R34479 A DER34479 A DE R34479A DE R0034479 A DER0034479 A DE R0034479A DE 1200275 B DE1200275 B DE 1200275B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- methylbenzenes
- perchlorination
- nucleus
- side chains
- 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 8
- 150000005172 methylbenzenes Chemical class 0.000 title claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 22
- 235000019270 ammonium chloride Nutrition 0.000 claims description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 238000005660 chlorination reaction Methods 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 3
- DDTHLQVVHGZPQB-UHFFFAOYSA-N 1,3,5-tris(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC(C(Cl)(Cl)Cl)=CC(C(Cl)(Cl)Cl)=C1 DDTHLQVVHGZPQB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- -1 B. halotoluenes Chemical class 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GGZIUXGYCNYNNV-UHFFFAOYSA-N 1,3-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC(C(Cl)(Cl)Cl)=C1 GGZIUXGYCNYNNV-UHFFFAOYSA-N 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical group ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- XOJYLEJZALFLLW-UHFFFAOYSA-N 1-fluoro-4-(trichloromethyl)benzene Chemical compound FC1=CC=C(C(Cl)(Cl)Cl)C=C1 XOJYLEJZALFLLW-UHFFFAOYSA-N 0.000 description 1
- WRWPPGUCZBJXKX-UHFFFAOYSA-N 1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C=C1 WRWPPGUCZBJXKX-UHFFFAOYSA-N 0.000 description 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 1
- VZEXJUAYWWLSEP-UHFFFAOYSA-N N.[Cl].Cl Chemical compound N.[Cl].Cl VZEXJUAYWWLSEP-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical class CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL122960D NL122960C (enrdf_load_stackoverflow) | 1963-02-16 | ||
| DER34479A DE1200275B (de) | 1963-02-16 | 1963-02-16 | Verfahren zur Perchlorierung der Seitenketten in Methylbenzolen und deren kernsubstituierten Derivaten |
| FR961795A FR1387417A (fr) | 1963-02-16 | 1964-01-28 | Procédé pour chlorurer les chaînes latérales de méthylbenzènes |
| BE643124D BE643124A (enrdf_load_stackoverflow) | 1963-02-16 | 1964-01-29 | |
| LU45321D LU45321A1 (enrdf_load_stackoverflow) | 1963-02-16 | 1964-01-30 | |
| CH134764A CH431481A (de) | 1963-02-16 | 1964-02-05 | Verfahren zur Perchlorierung der Seitenketten in Methylbenzolen |
| NL6400962A NL6400962A (enrdf_load_stackoverflow) | 1963-02-16 | 1964-02-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER34479A DE1200275B (de) | 1963-02-16 | 1963-02-16 | Verfahren zur Perchlorierung der Seitenketten in Methylbenzolen und deren kernsubstituierten Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1200275B true DE1200275B (de) | 1965-09-09 |
Family
ID=7404341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER34479A Pending DE1200275B (de) | 1963-02-16 | 1963-02-16 | Verfahren zur Perchlorierung der Seitenketten in Methylbenzolen und deren kernsubstituierten Derivaten |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE643124A (enrdf_load_stackoverflow) |
| CH (1) | CH431481A (enrdf_load_stackoverflow) |
| DE (1) | DE1200275B (enrdf_load_stackoverflow) |
| LU (1) | LU45321A1 (enrdf_load_stackoverflow) |
| NL (2) | NL6400962A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3456023A (en) * | 1967-05-31 | 1969-07-15 | Standard Oil Co | Halogenated alpha-methylstyrene haloform adducts |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2695873A (en) * | 1952-04-04 | 1954-11-30 | Hooker Electrochemical Co | Process for chlorinating methyl aromatic compounds |
-
0
- NL NL122960D patent/NL122960C/xx active
-
1963
- 1963-02-16 DE DER34479A patent/DE1200275B/de active Pending
-
1964
- 1964-01-29 BE BE643124D patent/BE643124A/xx unknown
- 1964-01-30 LU LU45321D patent/LU45321A1/xx unknown
- 1964-02-05 CH CH134764A patent/CH431481A/de unknown
- 1964-02-06 NL NL6400962A patent/NL6400962A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2695873A (en) * | 1952-04-04 | 1954-11-30 | Hooker Electrochemical Co | Process for chlorinating methyl aromatic compounds |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3456023A (en) * | 1967-05-31 | 1969-07-15 | Standard Oil Co | Halogenated alpha-methylstyrene haloform adducts |
Also Published As
| Publication number | Publication date |
|---|---|
| BE643124A (enrdf_load_stackoverflow) | 1964-05-15 |
| NL6400962A (enrdf_load_stackoverflow) | 1964-08-17 |
| CH431481A (de) | 1967-03-15 |
| NL122960C (enrdf_load_stackoverflow) | |
| LU45321A1 (enrdf_load_stackoverflow) | 1964-03-31 |
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