JP3078162B2 - α−メチルスチレン類の不飽和二量体の製造法 - Google Patents
α−メチルスチレン類の不飽和二量体の製造法Info
- Publication number
- JP3078162B2 JP3078162B2 JP05243536A JP24353693A JP3078162B2 JP 3078162 B2 JP3078162 B2 JP 3078162B2 JP 05243536 A JP05243536 A JP 05243536A JP 24353693 A JP24353693 A JP 24353693A JP 3078162 B2 JP3078162 B2 JP 3078162B2
- Authority
- JP
- Japan
- Prior art keywords
- methylstyrenes
- aqueous solution
- methylstyrene
- sulfonic acid
- acid compound
- 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
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 title claims description 39
- 239000000539 dimer Substances 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 28
- -1 sulfonic acid compound Chemical class 0.000 claims description 28
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 238000006471 dimerization reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- YWAKXRMUMFPDSH-UHFFFAOYSA-N propyl ethylene Natural products CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical class CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- ICLPNZMYHDVKKI-UHFFFAOYSA-N 1,1,3-trimethyl-3-phenyl-2h-indene Chemical compound C12=CC=CC=C2C(C)(C)CC1(C)C1=CC=CC=C1 ICLPNZMYHDVKKI-UHFFFAOYSA-N 0.000 description 1
- IBTHFIILQIUOEK-UHFFFAOYSA-N 1-ethyl-4-prop-1-en-2-ylbenzene Chemical compound CCC1=CC=C(C(C)=C)C=C1 IBTHFIILQIUOEK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VOOVDZMAQQVAEW-PFONDFGASA-N [(z)-2-methyl-4-phenylpent-3-en-2-yl]benzene Chemical compound C=1C=CC=CC=1C(/C)=C\C(C)(C)C1=CC=CC=C1 VOOVDZMAQQVAEW-PFONDFGASA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05243536A JP3078162B2 (ja) | 1993-09-06 | 1993-09-06 | α−メチルスチレン類の不飽和二量体の製造法 |
| TW083103596A TW272200B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-09-06 | 1994-04-22 | |
| EP94303125A EP0641756B1 (en) | 1993-09-06 | 1994-04-29 | Method of preparing unsaturated dimers of alpha-methylstyrenes |
| MYPI94001100A MY110392A (en) | 1993-09-06 | 1994-05-04 | Method of preparing unsaturated dimers of - ( ) methylstyrenes |
| CN94105198A CN1043878C (zh) | 1993-09-06 | 1994-05-17 | α－甲基苯乙烯类不饱和二聚体的制备方法 |
| US08/245,670 US5502264A (en) | 1993-09-06 | 1994-05-18 | Method of preparing unsaturated dimers of α-methylstyrenes |
| KR1019940012179A KR0139485B1 (ko) | 1993-09-06 | 1994-05-31 | 알파-메틸스틸렌류의 불포화 이량체의 제조법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05243536A JP3078162B2 (ja) | 1993-09-06 | 1993-09-06 | α−メチルスチレン類の不飽和二量体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0776533A JPH0776533A (ja) | 1995-03-20 |
| JP3078162B2 true JP3078162B2 (ja) | 2000-08-21 |
Family
ID=17105349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP05243536A Expired - Fee Related JP3078162B2 (ja) | 1993-09-06 | 1993-09-06 | α−メチルスチレン類の不飽和二量体の製造法 |
Country Status (7)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA34850C2 (uk) * | 1999-07-13 | 2001-10-15 | Горлівське Відкрите Акціонерне Товариство "Концерн Стирол" | СПОСІБ ОДЕРЖАННЯ НЕНАСИЧЕНОГО ДИМЕРУ <font face="Symbol">a</font>-МЕТИЛСТИРОЛУ ДЛЯ РЕГУЛЮВАННЯ РОСТУ ПОЛІМЕРНОГО ЛАНЦЮГА |
| RU2189963C1 (ru) * | 2001-05-28 | 2002-09-27 | ГУ Институт нефтехимии и катализа АН РБ и УНЦ РАН | СПОСОБ ПОЛУЧЕНИЯ НЕНАСЫЩЕННЫХ ДИМЕРОВ α-МЕТИЛСТИРОЛА |
| RU2189964C1 (ru) * | 2001-05-28 | 2002-09-27 | ГУ Институт нефтехимии и катализа АН РБ и УНЦ РАН | СПОСОБ ПОЛУЧЕНИЯ НЕНАСЫЩЕННЫХ ДИМЕРОВ α-МЕТИЛСТИРОЛА |
| RU2200142C1 (ru) * | 2001-07-23 | 2003-03-10 | ГУ Институт нефтехимии и катализа АН РБ и УНЦ РАН | СПОСОБ ПОЛУЧЕНИЯ НЕНАСЫЩЕННЫХ ДИМЕРОВ α-МЕТИЛСТИРОЛА |
| RU2239623C1 (ru) * | 2003-04-14 | 2004-11-10 | ГУ Институт нефтехимии и катализа АН РБ и УНЦ РАН | Способ получения ненасыщенных димеров альфа-метилстирола |
| RU2317967C1 (ru) * | 2006-09-04 | 2008-02-27 | Институт нефтехимии и катализа РАН | СПОСОБ ПОЛУЧЕНИЯ ЛИНЕЙНЫХ ДИМЕРОВ α-МЕТИЛСТИРОЛА |
| CN119930382B (zh) * | 2025-04-07 | 2025-07-29 | 山东富宇石化有限公司 | 一种制备α-甲基苯乙烯线性二聚体的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2249987A (en) | 1937-08-09 | 1941-07-22 | Distillers Co Yeast Ltd | Manufacture of derivatives of aryl substituted mono-olefins |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2646450A (en) * | 1951-05-25 | 1953-07-21 | Dow Chemical Co | Process for making unsaturated dimers of alpha-alkyl styrenes |
| JPS5557524A (en) * | 1978-10-25 | 1980-04-28 | Nippon Petrochem Co Ltd | Preparation of polycyclic aromatic hydrocarbon compound |
| US4334118A (en) * | 1981-06-01 | 1982-06-08 | Chevron Research | Solid phosphoric acid catalyzed olefin polymerization process |
| US4596896A (en) * | 1985-06-03 | 1986-06-24 | Phillips Petroleum Company | Acid catalyzed reactions of monovinyl aromatic compounds |
| JPH03203995A (ja) * | 1989-12-28 | 1991-09-05 | Nippon Steel Chem Co Ltd | 潤滑用油の製造方法 |
-
1993
- 1993-09-06 JP JP05243536A patent/JP3078162B2/ja not_active Expired - Fee Related
-
1994
- 1994-04-22 TW TW083103596A patent/TW272200B/zh active
- 1994-04-29 EP EP94303125A patent/EP0641756B1/en not_active Expired - Lifetime
- 1994-05-04 MY MYPI94001100A patent/MY110392A/en unknown
- 1994-05-17 CN CN94105198A patent/CN1043878C/zh not_active Expired - Fee Related
- 1994-05-18 US US08/245,670 patent/US5502264A/en not_active Expired - Lifetime
- 1994-05-31 KR KR1019940012179A patent/KR0139485B1/ko not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2249987A (en) | 1937-08-09 | 1941-07-22 | Distillers Co Yeast Ltd | Manufacture of derivatives of aryl substituted mono-olefins |
Also Published As
| Publication number | Publication date |
|---|---|
| US5502264A (en) | 1996-03-26 |
| EP0641756A1 (en) | 1995-03-08 |
| EP0641756B1 (en) | 1997-07-02 |
| CN1043878C (zh) | 1999-06-30 |
| KR0139485B1 (ko) | 1998-07-01 |
| JPH0776533A (ja) | 1995-03-20 |
| TW272200B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-03-11 |
| MY110392A (en) | 1998-04-30 |
| CN1100083A (zh) | 1995-03-15 |
| KR950008447A (ko) | 1995-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |