JPH0699329B2 - Method for side-chain alkylation of alkyl-substituted aromatic hydrocarbons - Google Patents
Method for side-chain alkylation of alkyl-substituted aromatic hydrocarbonsInfo
- Publication number
- JPH0699329B2 JPH0699329B2 JP60061881A JP6188185A JPH0699329B2 JP H0699329 B2 JPH0699329 B2 JP H0699329B2 JP 60061881 A JP60061881 A JP 60061881A JP 6188185 A JP6188185 A JP 6188185A JP H0699329 B2 JPH0699329 B2 JP H0699329B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted aromatic
- catalyst
- potassium carbonate
- present
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 32
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims description 28
- 238000005804 alkylation reaction Methods 0.000 title claims description 16
- 230000029936 alkylation Effects 0.000 title claims description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 58
- 239000003054 catalyst Substances 0.000 claims description 38
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 29
- 239000000843 powder Substances 0.000 claims description 26
- 150000001340 alkali metals Chemical class 0.000 claims description 22
- 229910052783 alkali metal Inorganic materials 0.000 claims description 20
- -1 aliphatic monoolefin Chemical class 0.000 claims description 17
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 10
- 239000002612 dispersion medium Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000002245 particle Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- FIPKSKMDTAQBDJ-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2C(C)CCC2=C1 FIPKSKMDTAQBDJ-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- QHTJSSMHBLGUHV-UHFFFAOYSA-N 2-methylbutan-2-ylbenzene Chemical compound CCC(C)(C)C1=CC=CC=C1 QHTJSSMHBLGUHV-UHFFFAOYSA-N 0.000 description 2
- IFDLFCDWOFLKEB-UHFFFAOYSA-N 2-methylbutylbenzene Chemical compound CCC(C)CC1=CC=CC=C1 IFDLFCDWOFLKEB-UHFFFAOYSA-N 0.000 description 2
- XNXIYYFOYIUJIW-UHFFFAOYSA-N 3-methylbutylbenzene Chemical compound CC(C)CCC1=CC=CC=C1 XNXIYYFOYIUJIW-UHFFFAOYSA-N 0.000 description 2
- PVXCNEZDIJHZQB-UHFFFAOYSA-N 3-methylpentylbenzene Chemical compound CCC(C)CCC1=CC=CC=C1 PVXCNEZDIJHZQB-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- UZILCZKGXMQEQR-UHFFFAOYSA-N decyl-Benzene Chemical compound CCCCCCCCCCC1=CC=CC=C1 UZILCZKGXMQEQR-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical class C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SECAQUZEXAHWBA-UHFFFAOYSA-N 1-ethyl-2,3-dihydro-1h-indene Chemical compound C1=CC=C2C(CC)CCC2=C1 SECAQUZEXAHWBA-UHFFFAOYSA-N 0.000 description 1
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 1
- HMAMGXMFMCAOPV-UHFFFAOYSA-N 1-propylnaphthalene Chemical compound C1=CC=C2C(CCC)=CC=CC2=C1 HMAMGXMFMCAOPV-UHFFFAOYSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YKNMBTZOEVIJCM-UHFFFAOYSA-N dec-2-ene Chemical compound CCCCCCCC=CC YKNMBTZOEVIJCM-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MYTMXVHNEWBFAL-UHFFFAOYSA-L dipotassium;carbonate;hydrate Chemical compound O.[K+].[K+].[O-]C([O-])=O MYTMXVHNEWBFAL-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
【発明の詳細な説明】 〔技術分野〕 本発明は、特定の方法によつて調製した、炭酸カリウム
粉体にアルカリ金属を担持せしめた触媒の存在下に、ア
ルキル置換芳香族炭化水素（ａ）を脂肪族モノオレフイ
ンを用いて側鎖アルキル化し、医薬、農薬等を製造する
際の中間体として有用な炭素数を増したアルキル置換芳
香族炭化水素（ｂ）を製造する方法に関する。TECHNICAL FIELD The present invention provides an alkyl-substituted aromatic hydrocarbon (a) prepared by a specific method in the presence of a catalyst prepared by supporting an alkali metal on potassium carbonate powder. The present invention relates to a method for producing an alkyl-substituted aromatic hydrocarbon (b) having an increased carbon number, which is useful as an intermediate in the production of pharmaceuticals, agricultural chemicals, etc.
アルキル置換芳香族炭化水素と脂肪族モノオレフインを
反応させ側鎖アルキル化反応によつて炭素数を増したア
ルキル置換芳香族炭化水素を製造する従来の方法に関し
ては、例えば英国特許明細書第1269280号には炭酸カリ
ウムに金属ナトリウムを担持した触媒を用いて該反応を
行う方法が開示されている。該公報には炭酸カリウムに
ナトリウムを蒸着担持する方法、液体アンモニアに溶解
したナトリウムを沈着担持する方法、あるいは不活性ガ
ス雰囲気下に150〜400℃で溶融させたナトリウムを混合
して担持する方法によって調製された触媒を使用できる
旨が記載されている。該公報の実施例の触媒はいずれも
高温でナトリウムを溶融担持する方法によつて調製した
触媒である。一般に高温下にアルカリ金属を溶融担持す
るためには、キルンなど特別な調製装置を必要とし操作
が繁雑であり、調製した触媒は容易に発火の危険性があ
ることからその取扱い上の安全性に課題をかかえてい
る。又得られる触媒においてはナトリウムの担体への分
散が不均一でありNa−Ｋ間の交換率が低い。そのため該
公報の実施例の結果も含めて従来の触媒の活性は未だ充
分とは言えない。Regarding a conventional method for producing an alkyl-substituted aromatic hydrocarbon having a carbon number increased by a side chain alkylation reaction by reacting an alkyl-substituted aromatic hydrocarbon with an aliphatic monoolefin, for example, British Patent Specification No. 1269280 Discloses a method of carrying out the reaction using a catalyst in which sodium carbonate is supported on potassium carbonate. In this publication, there is a method of depositing and supporting sodium on potassium carbonate, a method of depositing and supporting sodium dissolved in liquid ammonia, or a method of mixing and supporting sodium melted at 150 to 400 ° C. under an inert gas atmosphere. It is stated that the prepared catalyst can be used. The catalysts of the Examples of the publication are all prepared by a method of melting and supporting sodium at a high temperature. Generally, in order to melt and support an alkali metal at high temperature, a special preparation device such as a kiln is required and the operation is complicated, and the prepared catalyst has a risk of ignition easily. I have an issue. Further, in the obtained catalyst, the dispersion of sodium in the carrier is non-uniform and the exchange rate between Na and K is low. Therefore, it cannot be said that the activity of the conventional catalyst, including the results of the examples of the publication, is sufficient.
本発明者等は側鎖アルキル化反応によつて炭素数を増し
たアルキル置換芳香族炭化水素を製造する際に使用され
ている従来の触媒には前記した問題点のあることを認め
た。そこで、これを改良すべく従来に比べて簡単かつ安
全な方法によつてしかも活性の高い触媒を調製し、これ
を用いてアルキル置換芳香族炭化水素（ａ）を脂肪族モ
ノオレフインによつて側鎖アルキル化して炭素数を増し
たアルキル置換芳香族炭化水素（ｂ）を従来の触媒に比
して高い収量で得る方法について検討した。The present inventors have recognized that the conventional catalysts used for producing alkyl-substituted aromatic hydrocarbons having an increased number of carbon atoms by the side chain alkylation reaction have the above-mentioned problems. Therefore, in order to improve this, a catalyst having a high activity was prepared by a simpler and safer method than ever before, and the catalyst was used to remove an alkyl-substituted aromatic hydrocarbon (a) by an aliphatic monoolefin. A method for obtaining an alkyl-substituted aromatic hydrocarbon (b) having a higher number of carbon atoms by chain alkylation with a higher yield than conventional catalysts was examined.
その結果、下記方法を採用すれば前記目的を達成できる
ことを見出し本発明を完成するに到つた。すなわち本発
明の方法によれば、アルカリ置換芳香族炭化水素を脂肪
族モノオレフィンにより側鎖アルキル化するに際し、ア
ルカリ金属と炭酸カリウム粉体を脂肪族飽和炭化水素ま
たは脂環式炭化水素からなる分散媒中でアルカリ金属の
融点以上の温度で混合することにより炭酸カリウム粉体
にアルカリ金属を担持せしめた触媒を用いることを特徴
とするアルキル置換芳香族炭化水素の側鎖アルキル化方
法、が提示される。As a result, they have found that the above object can be achieved by adopting the following method, and completed the present invention. That is, according to the method of the present invention, in the side chain alkylation of an alkali-substituted aromatic hydrocarbon with an aliphatic monoolefin, an alkali metal and potassium carbonate powder are dispersed by an aliphatic saturated hydrocarbon or an alicyclic hydrocarbon. A method for side-chain alkylation of an alkyl-substituted aromatic hydrocarbon characterized by using a catalyst in which an alkali metal is supported on a potassium carbonate powder by mixing at a temperature above the melting point of the alkali metal in a medium is presented. It
触 媒 本発明で使用される触媒は特定の方法によつて炭酸カリ
ウム粉体にアルカリ金属を担持せしめた触媒である。す
なわち、本発明では、アルカリ金属と炭酸カリウム粉体
を脂肪族飽和炭化水素または脂環式炭化水素からなる分
散媒中でアルカリ金属の融点以上の温度で混合すること
により炭酸カリウム粉体にアルカリ金属を担持せしめた
触媒を用いて、アルキル置換芳香族炭化水素の側鎖アル
キル化反応が行われる。Catalyst The catalyst used in the present invention is a catalyst in which an alkali metal is supported on a potassium carbonate powder by a specific method. That is, in the present invention, the alkali metal and the potassium carbonate powder are mixed with the potassium carbonate powder by mixing them in a dispersion medium composed of an aliphatic saturated hydrocarbon or an alicyclic hydrocarbon at a temperature equal to or higher than the melting point of the alkali metal. The side-chain alkylation reaction of the alkyl-substituted aromatic hydrocarbon is carried out using the catalyst on which is carried.
本発明で使用されるアルカリ金属としてはリチウム、ナ
トリウム、カリウムなどであつて、この中でナトリウム
が好ましい。The alkali metal used in the present invention includes lithium, sodium, potassium and the like, of which sodium is preferred.
本発明で用いられる炭酸カリウム粉体については、従来
から知られている方法によつて得られる炭酸カリウム粉
体を使用することができる。本発明では特にどういつた
物性の炭酸カリウムを用いなければならならいというこ
とはないが、後述する反応の活性の点から本発明では以
下に示す物性を有する炭酸カリウム粉体を使用すること
が特に好ましい。すなわち、崇密度が通常0.85g/cm3以
下、平均粒径が通常100ないし800μでかつ粒径100ない
し800μの範囲にある粉体重量が全粉体重量の通常60％
以上を占める以上を占める炭酸カリウム粉体を用いて得
られる触媒を使用した場合には、本発明の側鎖アルキル
化反応によつて生成するアルキル置換芳香族炭化水素の
生成量が増大するので特に好ましい。なお前記平均粒径
はJIS規格標準ふるいを用いてふるい分け法によつて粒
度分布を求めRRS線図からメジアン径として求められ
る。As the potassium carbonate powder used in the present invention, the potassium carbonate powder obtained by a conventionally known method can be used. In the present invention, it is not particularly necessary to use potassium carbonate having different physical properties, but it is particularly preferable to use a potassium carbonate powder having the following physical properties in the present invention from the viewpoint of the activity of the reaction described below. preferable. That is, the weight of powders with a density of 0.85g / cm 3 or less, the average particle diameter of 100 to 800μ and the particle diameter of 100 to 800μ is usually 60% of the total powder weight.
When the catalyst obtained by using the potassium carbonate powder occupying the above or more is used, the production amount of the alkyl-substituted aromatic hydrocarbon produced by the side chain alkylation reaction of the present invention is particularly increased. preferable. The average particle diameter is obtained as a median diameter from the RRS diagram by obtaining a particle size distribution by a sieving method using a JIS standard sieve.
本発明で使用される脂肪族飽和炭化水素および脂環式炭
化水素としては、例えばヘキサン、ヘプタン、オクタ
ン、デカン、ドデカン、トリデカン等の脂肪族飽和炭化
水素およびテトラリン、デカリン、シクロヘキサン等の
脂環式炭化水素などを例示できるが、本発明ではこの中
でもヘキサン、ｎ−オクタン、ｎ−デカンを用いること
が好ましい。特に後述する本発明の反応において原料と
して用いられるアルキル置換芳香族炭化水素（ａ）を前
記分散媒として用いると、触媒調製に引き続いて反応を
開始できるので操作が簡単となり経済的かつ安全上有利
であるので特に好ましい。本発明では前記分散媒は単独
使用しても良いし、又必要に応じて混合使用することも
できる。Examples of the saturated aliphatic hydrocarbons and alicyclic hydrocarbons used in the present invention include aliphatic saturated hydrocarbons such as hexane, heptane, octane, decane, dodecane and tridecane, and alicyclic compounds such as tetralin, decalin and cyclohexane. Hydrocarbons can be exemplified, but in the present invention, it is preferable to use hexane, n-octane, and n-decane among them. In particular, when the alkyl-substituted aromatic hydrocarbon (a) used as a raw material in the reaction of the present invention described below is used as the dispersion medium, the reaction can be started subsequent to the preparation of the catalyst, which simplifies the operation and is economically and safety advantageous. It is particularly preferable because it exists. In the present invention, the dispersion medium may be used alone, or may be mixed and used if necessary.
本発明では、触媒を調製するに当たつて使用される炭酸
カリウム粉体とアルカリ金属の割合については、該粉体
の100重量部に対してアルカリ金属が通常0.5ないし10重
量部、好ましくは１ないし７重量部である。アルカリ金
属の量が0.5重量部以下の場合には後述する本発明の側
鎖アルキル化反応の活性が低く、又10重量部以上の場合
には均一な担持が困難であるばかりか、反応中に高重合
物を副生し、触媒を被毒する。また極端な場合にはピツ
チ様の固形物を発生し、反応器を閉塞する等のトラブル
を生ずるので好ましくない。また本発明で前記分散触媒
を使用する場合の割合については、炭酸カリウム粉体の
100重量部に対して通常100ないし1000重量部、好ましく
は150ないし500重量部である。In the present invention, the proportion of the potassium carbonate powder and the alkali metal used in preparing the catalyst is usually 0.5 to 10 parts by weight, preferably 1 part by weight of the alkali metal to 100 parts by weight of the powder. To 7 parts by weight. When the amount of the alkali metal is 0.5 parts by weight or less, the activity of the side chain alkylation reaction of the present invention described later is low, and when it is 10 parts by weight or more, it is difficult to uniformly carry out the reaction, and during the reaction, High polymer is produced as a by-product and poisons the catalyst. Further, in an extreme case, a pitch-like solid substance is generated and troubles such as clogging of the reactor occur, which is not preferable. Further, regarding the ratio when the dispersion catalyst is used in the present invention, the content of the potassium carbonate powder is
It is usually 100 to 1000 parts by weight, preferably 150 to 500 parts by weight, relative to 100 parts by weight.
本発明では、アルカリ金属と炭酸カリウム粉体を前記分
散触媒中にアルカリ金属の融点以上の温度で混合するこ
とによつてアルカリ金属を炭酸カリウム粉体に担持せし
めて本発明の触媒が得られるわけであるが、この場合の
該温度としては通常120ないし250℃、好ましくは150℃
ないし230℃である。該温度が120℃以下の場合には炭酸
カリウムのカリウムイオンとアルカリ金属との相互作用
ならびに炭酸カリウム粉体に由来するカリウムを担持し
ようとするアルカリ金属例えばナトリウムとの交換反応
が起こりにくいため高活性な触媒が得られないので好ま
しくない。また温度が250℃以上の場合には、金属状の
カリウムが多く副生し、反応中にピツチ状の固形物を生
成するので好ましくない。In the present invention, the catalyst of the present invention can be obtained by supporting the alkali metal on the potassium carbonate powder by mixing the alkali metal and the potassium carbonate powder in the dispersion catalyst at a temperature equal to or higher than the melting point of the alkali metal. However, the temperature in this case is usually 120 to 250 ° C, preferably 150 ° C.
To 230 ° C. When the temperature is 120 ° C or lower, the interaction between potassium ions of potassium carbonate and an alkali metal and the exchange reaction with an alkali metal such as sodium for supporting potassium derived from the potassium carbonate powder are unlikely to occur, resulting in high activity. It is not preferable because a good catalyst cannot be obtained. Further, if the temperature is 250 ° C. or higher, a large amount of metallic potassium is by-produced and a pitch-like solid substance is generated during the reaction, which is not preferable.
本発明では、前記方法によつて炭酸カリウム粉体にアル
カリ金属を担持して得られる触媒は、この後分散媒を除
去して水分を含まない不活性ガス雰囲気中にて反応に供
する迄保存しても良いし、あるいはそのまま水分を含ま
ない前記分散媒中にて保存しても良い。この場合、分散
媒として後述する本発明の側鎖アルキル化反応の原料と
して用いるアルキル置換芳香族炭化水素（ａ）を用いた
場合には、調製した触媒をそのまま次の反応に供するこ
とができるので特に好ましいことは前述したとおりであ
る。In the present invention, the catalyst obtained by carrying the alkali metal on the potassium carbonate powder by the above method is then stored in an inert gas atmosphere containing no water by removing the dispersion medium until the reaction. Alternatively, it may be stored in the dispersion medium containing no water as it is. In this case, when the alkyl-substituted aromatic hydrocarbon (a) used as a raw material for the side chain alkylation reaction of the present invention described below is used as the dispersion medium, the prepared catalyst can be directly used in the next reaction. Particularly preferable is as described above.
前記した本発明の方法によつて得られる触媒は、担体の
炭酸カリウム粉体に該炭酸カリウムに由来しないアルカ
リ金属が担体基準で通常0.5ないし10重量％、好ましく
は１ないし７重量％担持された触媒である。The catalyst obtained by the above-mentioned method of the present invention has a potassium carbonate powder as a carrier in which an alkali metal not derived from the potassium carbonate is normally supported in an amount of 0.5 to 10% by weight, preferably 1 to 7% by weight. It is a catalyst.
本発明の方法によれば従来法に比べて比較的低温でしか
も簡単な方法によつて後述する反応に対して高活性な触
媒が得られる。According to the method of the present invention, a catalyst having a high activity for the reaction described below can be obtained by a simple method at a relatively low temperature as compared with the conventional method.
反 応 本発明では前記方法によつて調製された触媒の存在下に
アルキル置換芳香族炭化水素（ａ）と脂肪族モノオレフ
インを反応させて側鎖アルキル化反応によつて炭素数を
増したアルキル置換芳香族炭化水素（ｂ）が製造され
る。Reaction In the present invention, an alkyl-substituted aromatic hydrocarbon (a) is reacted with an aliphatic monoolefin in the presence of a catalyst prepared by the above-mentioned method, and an alkyl having an increased number of carbon atoms is obtained by a side chain alkylation reaction. Substituted aromatic hydrocarbons (b) are produced.
本発明で使用されるアルキル置換芳香族炭化水素（ａ）
として具体的にはトルエン、エチルベンゼン、ｎ−プロ
ピルベンゼン、イソプロピルベンゼン、ｎ−ブチルベン
ゼン、sec-ブチルベンゼン、イソブチルベンゼン、ｎ−
デシルベンゼン、キシレン、メシチレン、テトラベンゼ
ン等のアルキル置換ベンゼン、メチルナフタレン、ジメ
チルナフタレン、イソプロピルナフタレン等のアルキル
置換ナフタレンおよびメチルインダン、エチルインダン
等のアルキル置換インダンなどを例示でき、本発明では
側鎖アルキル基においてα位の炭素に水素原子が結合し
たアルキル基を少なくとも１つ以上有するアルキル置換
芳香族炭化水素が使用される。本発明では前記したアル
キル置換芳香族炭化水素（ａ）の中でも特にトルエンを
使用することが好ましい。Alkyl-substituted aromatic hydrocarbon (a) used in the present invention
Specifically, toluene, ethylbenzene, n-propylbenzene, isopropylbenzene, n-butylbenzene, sec-butylbenzene, isobutylbenzene, n-
Examples include alkyl-substituted benzenes such as decylbenzene, xylene, mesitylene, and tetrabenzene, alkyl-substituted naphthalene such as methylnaphthalene, dimethylnaphthalene, and isopropylnaphthalene, and alkyl-substituted indan such as methylindane and ethylindane. An alkyl-substituted aromatic hydrocarbon having at least one alkyl group in which a hydrogen atom is bonded to the α-position carbon in the group is used. In the present invention, it is particularly preferable to use toluene among the above-mentioned alkyl-substituted aromatic hydrocarbons (a).
本発明で使用される脂肪族モノオレフインとして具体的
にはエチレン、プロピレン、１−ブテン、２−ブテン、
イソブチレン、１−ペンテン、２−ペンテン、１−ヘキ
セン、２−ヘキセン、３−ヘキセン、１−ヘプテン、２
−ヘプテン、２−オクテン、２−デセン、３−メチル−
１−ブテン、２−メチル−２−ブテン、４−メチル−１
−ペンテン等を例示できるが、この中ではエチレン、プ
ロピレン、１−ブテン、２−ブテン、イソブテンを使用
することが好ましい。Specific examples of the aliphatic monoolefin used in the present invention include ethylene, propylene, 1-butene, 2-butene,
Isobutylene, 1-pentene, 2-pentene, 1-hexene, 2-hexene, 3-hexene, 1-heptene, 2
-Heptene, 2-octene, 2-decene, 3-methyl-
1-butene, 2-methyl-2-butene, 4-methyl-1
-Pentene and the like can be exemplified, but among these, ethylene, propylene, 1-butene, 2-butene and isobutene are preferably used.
本発明の方法では、前記したアルキル置換芳香族炭化水
素（ａ）と脂肪族モノオレフインを反応させる場合の条
件として、これら原料の仕込み割合については、アルキ
ル置換芳香族炭化水素（ａ）の100モル部に対して脂肪
族モノオレフインは通常10ないし2000モル部、好ましく
は100ないし700モル部である。触媒の使用量について
は、アルキル置換芳香族炭化水素（ａ）の100重量部当
たり通常0.1ないし50重量部、好ましくは１ないし20重
量部の触媒が用いられる。本発明では触媒調製後、反応
を行うに当たつて必要に応じて例えばベンゼン、エチル
アミン、トリエチルアミン、ブチルアミン、シクロヘキ
シルアミン、トルイジン、ｎ−デカリン、ヘキサン、シ
クロヘキサン等の反応溶媒を適宜の量用いても差し支え
ない。In the method of the present invention, as a condition for reacting the alkyl-substituted aromatic hydrocarbon (a) with the aliphatic monoolefin, the charging ratio of these raw materials is 100 mol of the alkyl-substituted aromatic hydrocarbon (a). The amount of the aliphatic monoolefin is usually 10 to 2000 parts by mol, preferably 100 to 700 parts by mol based on parts. The amount of the catalyst used is usually 0.1 to 50 parts by weight, preferably 1 to 20 parts by weight, per 100 parts by weight of the alkyl-substituted aromatic hydrocarbon (a). In the present invention, after the catalyst is prepared, a reaction solvent such as benzene, ethylamine, triethylamine, butylamine, cyclohexylamine, toluidine, n-decalin, hexane and cyclohexane may be used in an appropriate amount, if necessary, in carrying out the reaction. It doesn't matter.
本発明の方法では、反応を例えば回分式の場合は以下の
方法によつて実施することができる。オートクレーブ等
の反応器にアルキル置換芳香族炭化水素（ａ）、触媒お
よび必要に応じて反応溶媒を所定量仕込み、所定の温度
に昇温してから脂肪族モノオレフインを所定量注入する
方法を示すことができるが、本発明では必ずしもこの方
法に限定されるものではなく、反応の他の方式として固
定床加圧流通式を用いることができる。反応は撹拌下に
実施され、反応温度としては通常140ないし250℃、好ま
しくは150ないし200℃であり、反応圧力は通常10ないし
200気圧の範囲にある。反応時間は通常１ないし20時間
である。In the method of the present invention, the reaction can be carried out, for example, in the case of a batch system by the following method. A method is shown in which a reactor such as an autoclave is charged with a predetermined amount of an alkyl-substituted aromatic hydrocarbon (a), a catalyst and optionally a reaction solvent, the temperature is raised to a predetermined temperature, and then a predetermined amount of aliphatic monoolefin is injected. However, the present invention is not necessarily limited to this method, and a fixed bed pressure flow system can be used as another system of the reaction. The reaction is carried out under stirring, the reaction temperature is usually 140 to 250 ° C, preferably 150 to 200 ° C, and the reaction pressure is usually 10 to 250 ° C.
It is in the range of 200 bar. The reaction time is usually 1 to 20 hours.
反応終了後、反応混合物を濾過して触媒を除き、蒸留、
晶析等の通常の分離手段によつて本発明の目的とする側
鎖アルキル化反応によつて炭素数を増したアルキル置換
芳香族炭化水素（ｂ）を分離することができる。本発明
では該アルキル置換芳香族炭化水素（ｂ）として具体的
には、ｎ−プロピルベンゼン、ｎ−プロピルトルエン、
sec-ブチルベンゼン、sec-ブチルトルエン、tert−アミ
ルベンゼン、イソブチルベンゼン、イソブチルトルエ
ン、２−メチルベンゼン、２−メチルブチルトルエン、
ｎ−プロピルナフタレン、等を例示できるが、この中で
はｎ−プロピルベンゼン、ｎ−プロピルトルエン、イソ
ブチルベンゼン、イソブチルトルエン、tert−アミルベ
ンゼン、２−メチルブチルベンゼン、２−メチルブチル
トルエンなどが好ましい。After completion of the reaction, the reaction mixture is filtered to remove the catalyst, distilled,
The alkyl-substituted aromatic hydrocarbon (b) having an increased number of carbon atoms can be separated by the side chain alkylation reaction aimed at by the present invention by a usual separation means such as crystallization. In the present invention, as the alkyl-substituted aromatic hydrocarbon (b), specifically, n-propylbenzene, n-propyltoluene,
sec-butylbenzene, sec-butyltoluene, tert-amylbenzene, isobutylbenzene, isobutyltoluene, 2-methylbenzene, 2-methylbutyltoluene,
Examples thereof include n-propylnaphthalene, and among them, n-propylbenzene, n-propyltoluene, isobutylbenzene, isobutyltoluene, tert-amylbenzene, 2-methylbutylbenzene, 2-methylbutyltoluene and the like are preferable.
本発明の方法によれば、従来法に比べて簡単な方法によ
つて分散媒中で調製される、アルカリ金属を炭酸カリウ
ム粉体に担持した触媒を用いることにより、側鎖アルキ
ル化反応により炭素数を増したアルキル置換芳香族炭化
水素（ｂ）を従来法に比べて高い収量で得ることができ
る。According to the method of the present invention, by using a catalyst prepared by dispersing an alkali metal on potassium carbonate powder, which is prepared in a dispersion medium by a simple method as compared with the conventional method, carbon atoms can be obtained by a side chain alkylation reaction. The increased number of alkyl-substituted aromatic hydrocarbons (b) can be obtained in a higher yield than the conventional method.
以下、本発明の方法を実施例によつて具体的に説明す
る。Hereinafter, the method of the present invention will be specifically described with reference to Examples.
実施例 １ 炭酸カリウム水溶液をエバポレーターで濃縮して得られ
た結晶を遠心分離器で脱水した後粉砕し、400℃で２時
間焼成することによつて炭酸カリウム粉末を得た。この
顆粒状粉末は嵩密度が0.78g/mlであり、平均粒径（Dme
d）は320μ、かつ粒度分布は100〜800μの粒径の粒子が
全体の85％を占めた。Example 1 A potassium carbonate powder was obtained by dehydrating a crystal obtained by concentrating an aqueous potassium carbonate solution with an evaporator using a centrifugal separator, pulverizing the crystal, and calcining at 400 ° C. for 2 hours. This granular powder has a bulk density of 0.78 g / ml and an average particle size (Dme
In d), particles having a particle size of 320μ and a particle size distribution of 100 to 800μ accounted for 85% of the whole.
この炭酸カリウム57gおよび金属ナトリウム3gならびに
ｎ−デカン 200mlとともにオートクレーブに入れ、230
度で３時間600rpmの回転数で撹拌することによつて触媒
を調製した。反応器の温度を160℃に下げ、β−メチル
ナフタレン200gを加えた後、エチレンを容器内の圧力が
50kg/cm2に達するまで圧入した。２時間後容器内の圧力
は28kg/cm2を示した。結果を第１表に示す。Into an autoclave with 57 g of potassium carbonate, 3 g of sodium metal and 200 ml of n-decane, 230
The catalyst was prepared by stirring for 3 hours at 600 rpm. After lowering the reactor temperature to 160 ° C and adding 200 g of β-methylnaphthalene, the ethylene pressure inside the vessel was adjusted.
It was pressed in until it reached 50 kg / cm 2 . After 2 hours, the pressure in the container was 28 kg / cm 2 . The results are shown in Table 1.
比較例１ 炭酸カリウム1.5水和塩のスラリーを150℃で噴霧乾燥し
て得られた顆粒状粉末を400℃で２時間焼成した後、乾
燥室雰囲気下に嵩密度および粒度分布をロータップ法に
て測定した。この炭酸カリウムの嵩密度は0.67g/mlであ
り、平均粒子径（メジアン径Dmed）は420μであり、さ
らに100〜800μの粒径の粒子が全体の92％を占めた。こ
の炭酸カリウムを撹拌装置についた円筒形のセパラブル
フラスコに入れ、マントルヒーターを用いて190℃に昇
温した。窒素雰囲気下に撹拌しながら、金属ナトリウム
を少量づつ落下し、添加後も約１時間同じ状態で撹拌を
継続した。室温まで昇温して調製した触媒60gをｎ−デ
カン200mlならびにβ−メチルナフタレン200gとともに
オートクレーブに入れ、160℃でエチレンを50kg/cm2ま
で圧入して反応させた結果を表３に示した。Comparative Example 1 A slurry of potassium carbonate hydrate was spray-dried at 150 ° C. to obtain a granular powder, which was calcined at 400 ° C. for 2 hours, and then the bulk density and particle size distribution were measured by a low tap method in a drying chamber atmosphere. It was measured. The bulk density of this potassium carbonate was 0.67 g / ml, the average particle diameter (median diameter Dmed) was 420μ, and particles having a particle diameter of 100 to 800μ accounted for 92% of the whole. This potassium carbonate was placed in a cylindrical separable flask equipped with a stirrer and heated to 190 ° C. using a mantle heater. While stirring under a nitrogen atmosphere, metallic sodium was dropped little by little, and stirring was continued in the same state for about 1 hour after the addition. 60 g of the catalyst prepared by raising the temperature to room temperature was put in an autoclave together with 200 ml of n-decane and 200 g of β-methylnaphthalene, and the reaction was carried out by pressurizing ethylene to 50 kg / cm 2 at 160 ° C. and showing the results in Table 3.
なお５時間で容器内の圧力は32kg/cm2を示した。The pressure in the container was 32 kg / cm 2 in 5 hours.
Claims (3)
オレフィンにより側鎖アルキル化するに際し、アルカリ
金属と炭酸カリウム粉体を脂肪族飽和炭化水素または脂
環式炭化水素からなる分散媒中でアルカリ金属の融点以
上の温度で混合することにより炭酸カリウム粉体にアル
カリ金属を担持せしめた触媒を用いることを特徴とする
アルキル置換芳香族炭化水素の側鎖アルキル化方法。1. When side-chain alkylating an alkyl-substituted aromatic hydrocarbon with an aliphatic monoolefin, an alkali metal and potassium carbonate powder are alkali-diluted in a dispersion medium composed of an aliphatic saturated hydrocarbon or an alicyclic hydrocarbon. A method for side-chain alkylation of an alkyl-substituted aromatic hydrocarbon, which comprises using a catalyst in which an alkali metal is supported on a potassium carbonate powder by mixing at a temperature equal to or higher than the melting point of the metal.
１に記載の側鎖アルキル化方法。2. The side chain alkylation method according to claim 1, wherein the dispersion medium is an aliphatic saturated hydrocarbon.
求項１に記載の側鎖アルキル化方法。3. The side chain alkylation method according to claim 1, wherein the saturated aliphatic hydrocarbon is n-decane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60061881A JPH0699329B2 (en) | 1985-03-28 | 1985-03-28 | Method for side-chain alkylation of alkyl-substituted aromatic hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60061881A JPH0699329B2 (en) | 1985-03-28 | 1985-03-28 | Method for side-chain alkylation of alkyl-substituted aromatic hydrocarbons |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61221133A JPS61221133A (en) | 1986-10-01 |
| JPH0699329B2 true JPH0699329B2 (en) | 1994-12-07 |
Family
ID=13183923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60061881A Expired - Fee Related JPH0699329B2 (en) | 1985-03-28 | 1985-03-28 | Method for side-chain alkylation of alkyl-substituted aromatic hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0699329B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI77387C (en) * | 1986-12-31 | 1989-03-10 | Neste Oy | KATALYSATORSYSTEM OCH FOERFARANDE FOER SELEKTIV ALKYLERING AV TOLUEN MED PROPEN. |
| US5157186A (en) * | 1990-11-13 | 1992-10-20 | Ethyl Corporation | Process for catalytic coupling of an alkene with an aromatic hydrocarbon |
| FR2703678B1 (en) * | 1993-04-08 | 1995-06-23 | Inst Francais Du Petrole | Process for the preparation of isobutylbenzene in the presence of a supported catalyst. |
| JP3250899B2 (en) * | 1993-12-27 | 2002-01-28 | 日石三菱株式会社 | Method for side-chain alkylation of alkyl-substituted aromatic hydrocarbons |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6153229A (en) * | 1984-08-22 | 1986-03-17 | Nippon Petrochem Co Ltd | Alkylation process |
| JPS6157526A (en) * | 1984-08-29 | 1986-03-24 | Nippon Petrochem Co Ltd | Production of aromatic hydrocarbon |
-
1985
- 1985-03-28 JP JP60061881A patent/JPH0699329B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61221133A (en) | 1986-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1259298A (en) | Dimerization process and catalysts therefor | |
| US4810688A (en) | Catalyst support and catalyst for olefin dimerization | |
| JP2748631B2 (en) | Method for producing alkyl-substituted aromatic hydrocarbon | |
| JPH0699329B2 (en) | Method for side-chain alkylation of alkyl-substituted aromatic hydrocarbons | |
| EP0351748B1 (en) | Potassium carbonate supports, catalysts, and olefin dimerization processes therewith | |
| KR0142427B1 (en) | Process for preparing alkyl-substituted aromatic hydrocarbons | |
| JPH0639396B2 (en) | Method for side-chain alkylation of alkyl-substituted aromatic hydrocarbons | |
| JPH05310613A (en) | Production of monoalkenylbenzene | |
| CA1326863C (en) | Process for preparing alkyl-substituted aromatic hydrocarbons | |
| EP0406867A1 (en) | Catalysts and catalyst supports, with inorganic nitrates, for olefin dimerization | |
| JP2748646B2 (en) | Method for producing alkyl-substituted aromatic hydrocarbon | |
| JPS61263643A (en) | Preparation of catalyst deposited with alkali metal | |
| JP2625985B2 (en) | Method for producing alkyl-substituted aromatic hydrocarbon | |
| JP2596108B2 (en) | Preparation of alkyl-substituted aromatic hydrocarbons | |
| JP2830129B2 (en) | Preparation of alkyl-substituted aromatic hydrocarbons | |
| GB2254802A (en) | Catalyst composition for coupling process | |
| US5347062A (en) | Process for preparing alkyl-substituted aromatic hydrocarbons | |
| US5157186A (en) | Process for catalytic coupling of an alkene with an aromatic hydrocarbon | |
| JP3028020B2 (en) | Method for producing monoalkenylbenzenes | |
| JP2792132B2 (en) | Process for producing alkyl-substituted aromatic hydrocarbons | |
| JP3317614B2 (en) | Method for producing monoalkenylbenzene | |
| JPH06256233A (en) | Side chain alkalation of alkyl-substituted aromatic hydrocarbon | |
| US5105048A (en) | Catalyst and catalyst supports, with inorganic nitrates, for olefin dimerization | |
| JP2748577B2 (en) | Process for producing alkyl-substituted aromatic hydrocarbons | |
| US5202515A (en) | Process for preparing alkyl-substituted aromatic hydrocarbons |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |