JPH0330577B2 - - Google Patents
Info
- Publication number
- JPH0330577B2 JPH0330577B2 JP57227039A JP22703982A JPH0330577B2 JP H0330577 B2 JPH0330577 B2 JP H0330577B2 JP 57227039 A JP57227039 A JP 57227039A JP 22703982 A JP22703982 A JP 22703982A JP H0330577 B2 JPH0330577 B2 JP H0330577B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- exchange resin
- carbinols
- cation exchange
- methylphenyl
- 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 - Lifetime
Links
- 238000006243 chemical reaction Methods 0.000 claims description 28
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical class CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 18
- -1 aromatic olefins Chemical class 0.000 claims description 18
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003729 cation exchange resin Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000006297 dehydration reaction Methods 0.000 description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 2
- UGPWRRVOLLMHSC-UHFFFAOYSA-N 2-[3-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(C(C)(C)O)=C1 UGPWRRVOLLMHSC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- YVJRCWCFDJYONJ-UHFFFAOYSA-N hydroperoxymethylbenzene Chemical class OOCC1=CC=CC=C1 YVJRCWCFDJYONJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- BHCGGVIVFXWATI-UHFFFAOYSA-N 1-[4-(1-hydroxyethyl)phenyl]ethanol Chemical compound CC(O)C1=CC=C(C(C)O)C=C1 BHCGGVIVFXWATI-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- UENHVTKPLPMSGQ-UHFFFAOYSA-N 2-(3-prop-1-en-2-ylphenyl)propan-2-ol Chemical compound CC(=C)C1=CC=CC(C(C)(C)O)=C1 UENHVTKPLPMSGQ-UHFFFAOYSA-N 0.000 description 1
- ABENQEFPIVJKAK-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)-3-methylphenyl]propan-2-ol Chemical compound CC1=CC(C(C)(C)O)=CC=C1C(C)(C)O ABENQEFPIVJKAK-UHFFFAOYSA-N 0.000 description 1
- LEARFTRDZQQTDN-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=C(C(C)(C)O)C=C1 LEARFTRDZQQTDN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57227039A JPS59118724A (ja) | 1982-12-27 | 1982-12-27 | メチルフエニルカルビノ−ル類の脱水方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57227039A JPS59118724A (ja) | 1982-12-27 | 1982-12-27 | メチルフエニルカルビノ−ル類の脱水方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59118724A JPS59118724A (ja) | 1984-07-09 |
| JPH0330577B2 true JPH0330577B2 (ru) | 1991-04-30 |
Family
ID=16854565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57227039A Granted JPS59118724A (ja) | 1982-12-27 | 1982-12-27 | メチルフエニルカルビノ−ル類の脱水方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59118724A (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007153783A (ja) * | 2005-12-02 | 2007-06-21 | Kansai Paint Co Ltd | 芳香環に共役した二重結合を有する化合物の製造方法 |
| JP2010143854A (ja) * | 2008-12-18 | 2010-07-01 | Sumitomo Chemical Co Ltd | 高純度ジイソプロペニルベンゼンの製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5314542A (en) * | 1976-07-26 | 1978-02-09 | Matsushita Electric Ind Co Ltd | Non-stable multi-vibrator |
| JPS5695132A (en) * | 1980-10-31 | 1981-08-01 | Sumitomo Chem Co Ltd | Preparation of high purity styrene by dehydration of alpha-phenylethyl alcohol |
-
1982
- 1982-12-27 JP JP57227039A patent/JPS59118724A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5314542A (en) * | 1976-07-26 | 1978-02-09 | Matsushita Electric Ind Co Ltd | Non-stable multi-vibrator |
| JPS5695132A (en) * | 1980-10-31 | 1981-08-01 | Sumitomo Chem Co Ltd | Preparation of high purity styrene by dehydration of alpha-phenylethyl alcohol |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59118724A (ja) | 1984-07-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100763216B1 (ko) | 고순도 디이소부텐의 제조방법 | |
| RU2282625C2 (ru) | Получение соединений оксирана | |
| KR100582808B1 (ko) | 비스페놀 에이의 제조방법 | |
| JP2001199919A (ja) | ビスフェノールａの製造方法 | |
| JPH05286879A (ja) | 高純度フェノールの製造方法 | |
| KR960002599B1 (ko) | 디올레핀의 선택적 히드로포르밀화 방법 | |
| JPS5858332B2 (ja) | フエノ−ルの製造法 | |
| JPH0330577B2 (ru) | ||
| JPH01149736A (ja) | １−アリール−アルケン−１の製法 | |
| US6593491B2 (en) | Production of tertiary butyl acetate | |
| EP1318135B1 (en) | Method for producing 1,1-bis-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane | |
| JP4012322B2 (ja) | ビスフェノールａの製造方法 | |
| JPH0244821B2 (ru) | ||
| JP4337815B2 (ja) | ω−シアノアルデヒド化合物の製造法 | |
| JPH052658B2 (ru) | ||
| US2555185A (en) | Recovery of organic compounds from aqueous carbon oxide hydrogenation product | |
| WO2002022535A1 (fr) | Procede de production de 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane | |
| US5688973A (en) | Process for the production of 2-vinyl-1,3-dioxolane | |
| JPH0812601A (ja) | α−アルキルスチレン類多量体の製造法 | |
| JPH0245439A (ja) | ビスフエノールの製造方法 | |
| JP4489549B2 (ja) | 高純度２，２−ビス（３’−シクロヘキセニル）プロパンの製造方法 | |
| KR20060021338A (ko) | 쿠멘 하이드로퍼옥사이드로부터의 비스페놀 ａ의 통합적제조방법 | |
| JP2000229899A (ja) | ビスフェノールａの製造方法 | |
| JPS6152821B2 (ru) | ||
| US5639922A (en) | Process for treatment of hydroperoxide mixture |