SU384807A1 - METHOD FOR PRODUCING ARYLMETHYLATED AROMATIC HYDROCARBONS - Google Patents
METHOD FOR PRODUCING ARYLMETHYLATED AROMATIC HYDROCARBONSInfo
- Publication number
- SU384807A1 SU384807A1 SU1406699A SU1406699A SU384807A1 SU 384807 A1 SU384807 A1 SU 384807A1 SU 1406699 A SU1406699 A SU 1406699A SU 1406699 A SU1406699 A SU 1406699A SU 384807 A1 SU384807 A1 SU 384807A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- arylmethylated
- producing
- aromatic hydrocarbons
- catalyst
- mixture
- Prior art date
Links
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 6
- -1 aryl chloromethanes Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910001510 metal chloride Inorganic materials 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910008433 SnCU Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
1one
Изобретение относитс к способу получейи арилметилированных органических соединений .This invention relates to a process for the preparation of arylmethylated organic compounds.
Известен способ получени арилметилированных ароматических соединений при взаимодействии ароматических углеводородов с арилхлорметанами или бисхлорметаиами в присутствии катализатора - комплексного соединени хлоридов металлов и солей четырехзамещениого аммони .A known method of producing arylmethylated aromatic compounds by reacting aromatic hydrocarbons with aryl chloromethanes or bischloromethiaes in the presence of a catalyst is a complex compound of metal chlorides and ammonium tetrasubstituted salts.
Однако дл получени продуктов по известному способу требуетс много времени из-за низкой скорости реакции.However, it takes a long time to produce products according to a known method due to the low reaction rate.
С целью сокращени времени реакции предлагаетс использовать в качестве катализатора комплексное соединение хлоридов металлов с сол ми четырехзамещенного аммони общей формулы M.eCU--R4-Cl-A, где при п 0,5-2 моль, или , где МеС1х А1С1з, РеСЬ, ZnCb или SnCU; R4 - тетраалкил, триалкиларил, диалкиларил-Н , арил-ЗН.In order to shorten the reaction time, it is proposed to use as a catalyst a complex compound of metal chlorides with tetra-substituted ammonium salts of the general formula M.eCU - R4-Cl-A, where at p 0.5-2 mol, or, where MeC1x A1C1z, PES, ZnCb or SnCU; R4 is tetraalkyl, trialkylaryl, dialkylaryl-H, aryl-3N.
Пример 1. Смесь ароматического углеводорода , арилхлорметана и катализатора, вз тых в мол рных отношени х 10:1:0,01; 10:1: 0,05; 5:1: 0,05; 2:1: 0,05, нагревают с обратным холодильником при 100-110°С с поглощением выдел ющегос хлористого водорода. Врем реакции зависит от концентрации катализатора.Example 1. A mixture of an aromatic hydrocarbon, aryl chloromethane and a catalyst, taken in a molar ratio of 10: 1: 0.01; 10: 1: 0.05; 5: 1: 0.05; 2: 1: 0.05, heated under reflux at 100-110 ° С with absorption of released hydrogen chloride. The reaction time depends on the concentration of the catalyst.
По окончании выделени хлористого водорода катализатор осаждаетс на дно реактора в виде в зкой жидкости, которую после отделени от реакционной смеси декантацией можно повторно использовать. Реакционную смесь разгон ют, отдел непрореагировавшие исходные вещества и продукты реакции. Выход целевого продукта 75-90%.At the end of the evolution of hydrogen chloride, the catalyst is deposited on the bottom of the reactor in the form of a viscous liquid, which, after separation from the reaction mixture, can be re-used by decantation. The reaction mixture is distilled, the unreacted starting materials and the reaction products are separated. The yield of the target product is 75-90%.
Процесс можно проводить непрерывно в каскаде аппаратов идеально10 смешени .The process can be carried out continuously in a cascade of devices ideally 10 mix.
Пример 2. Смесь нафталина, арилхлорметана (/г-, о- или лг-ксилилхлориды или смесь ксилилхлоридов, полученных хлорметилированием толуола) и катализатора, вз тых в мол рном отношении 5:1:0,05; 2:1:0,05, нагревают, как в примере 1, при 100-120 С. Врем реакции 0,5-2 час.Example 2. A mixture of naphthalene, aryl chloromethane ((g, o, or lg xylyl chlorides or a mixture of xylyl chlorides obtained by chloromethylation of toluene) and catalyst, taken in a molar ratio of 5: 1: 0.05; 2: 1: 0.05, heated as in example 1, at 100-120 C. The reaction time is 0.5-2 hours.
Непрореагировавший нафталин отгон ют. Выход технического толилнафтилметана 95-Unreacted naphthalene is distilled off. The output of technical tolylnaphthylmethane 95-
96%, По 1,6370-1,6430 (в зависимости от исходного ксилилхлорида).96% According to 1.6370-1.6430 (depending on the starting xyllyl chloride).
Технический продукт можно примен ть вTechnical product can be applied in
качестве пластификатора без дополнительнойas a plasticizer without additional
очистки или очищать перегонкой в вакууме.cleaning or distilling by distillation in a vacuum.
Выход очищенных продуктов до 85% (от технических).The yield of purified products up to 85% (from technical).
Пример 3. Смесь углеводорода АгН,Example 3. The mixture of hydrocarbon AGN,
арилхлорметана ArCHjCl и катализатора нагревают и обрабатывают аналогично приме эам 1 и 2, получа углеводороды общей формулы АгСН2Аг, где Аг и Аг - арил, строение которых зависит от строени исходного ароматического углеводорода и арилхлорметана. Способ может быть применен дл получени более сложных углеводородов , исход из бисхлорметиларепов ClHoCArCHaCl. Углеводороды получают в виде смеси изомеров , которые можно разделить обычными способами. Полученные в примерах продукты и услови реакции приведены в таблице. 5 10 15 б Предмет изобретени Способ получени арилметилированных ароматических углеводородов путем взаимодействи ароматических углеводородов с арилхлорметапами или бисхлорметанами в присутствии катализатора на основе комплексного соединенн хлоридов металлов, и солей четырехзамещенного аммони , отличающийс тем, что, с целью сокращени времени реакции, используют комплексный катализатор общей формулы MeClx-R4-NC1-А, где А -пНС1 нри п 0,5-2,0 моль или MeCU, где МеС1х А1С1з, РеСЬ, ZnCb или SnCU; R4 -тетраалкил, триалкиларил, диалкиларил-Н , арил-ЗН.arylchloromethane ArCHjCl and the catalyst are heated and treated similarly to Examples 1 and 2 to produce hydrocarbons of the general formula AgCH2Ag, where Ar and Ar are aryl, the structure of which depends on the structure of the original aromatic hydrocarbon and arylchloromethane. The method can be applied to produce more complex hydrocarbons, starting from ClHoCA-CHaCl bischlormethylrepreps. Hydrocarbons are obtained as a mixture of isomers, which can be separated by conventional methods. The products and reaction conditions obtained in the examples are listed in the table. 5 10 15 b Subject of the invention A method for producing arylmethylated aromatic hydrocarbons by reacting aromatic hydrocarbons with arylchlorometaps or bischloromethanes in the presence of a catalyst based on a complex compound of metal chlorides, and tetrasubstituted ammonium salts, characterized in that, in order to shorten the reaction time, a complex catalyst of the general formula MeClx-R4-NC1-A, where A is pNCl1 and 0.5-2.0 mol, or MeCU, where MeClx A1Cl3, PeCl, ZnCb or SnCU; R4-tetraalkyl, trialkylaryl, dialkylamino-H, aryl-3N.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1406699A SU384807A1 (en) | 1970-02-26 | 1970-02-26 | METHOD FOR PRODUCING ARYLMETHYLATED AROMATIC HYDROCARBONS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1406699A SU384807A1 (en) | 1970-02-26 | 1970-02-26 | METHOD FOR PRODUCING ARYLMETHYLATED AROMATIC HYDROCARBONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU384807A1 true SU384807A1 (en) | 1973-05-29 |
Family
ID=20450165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1406699A SU384807A1 (en) | 1970-02-26 | 1970-02-26 | METHOD FOR PRODUCING ARYLMETHYLATED AROMATIC HYDROCARBONS |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU384807A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814508A (en) * | 1984-10-11 | 1989-03-21 | Raychem Corporation | Friedel-crafts preparation of aromatic ketones |
-
1970
- 1970-02-26 SU SU1406699A patent/SU384807A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814508A (en) * | 1984-10-11 | 1989-03-21 | Raychem Corporation | Friedel-crafts preparation of aromatic ketones |
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