JPH0439449B2 - - Google Patents
Info
- Publication number
- JPH0439449B2 JPH0439449B2 JP58151502A JP15150283A JPH0439449B2 JP H0439449 B2 JPH0439449 B2 JP H0439449B2 JP 58151502 A JP58151502 A JP 58151502A JP 15150283 A JP15150283 A JP 15150283A JP H0439449 B2 JPH0439449 B2 JP H0439449B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chloride
- ethoxyphenyl
- methallyl
- chloro
- 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
- -1 methallyl halide Chemical class 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000003377 acid catalyst Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FISWUVUAFGHPHT-UHFFFAOYSA-N 2-chloro-4-(1-chloro-2-methylpropan-2-yl)-1-ethoxybenzene Chemical compound CCOC1=CC=C(C(C)(C)CCl)C=C1Cl FISWUVUAFGHPHT-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CUYNTLDCNGKIFN-UHFFFAOYSA-N 1-(1-chloro-2-methylpropan-2-yl)-4-ethoxybenzene Chemical compound CCOC1=CC=C(C(C)(C)CCl)C=C1 CUYNTLDCNGKIFN-UHFFFAOYSA-N 0.000 description 4
- IRYSAAMKXPLGAM-UHFFFAOYSA-N 1-chloro-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1Cl IRYSAAMKXPLGAM-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- KGLZPSRIHZQTQV-UHFFFAOYSA-N 1-chloro-3-(1-chloro-2-methylpropan-2-yl)-2-ethoxybenzene Chemical compound CCOC1=C(Cl)C=CC=C1C(C)(C)CCl KGLZPSRIHZQTQV-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XCOKKVWDJYSCRZ-UHFFFAOYSA-N 1-phenoxy-3-[(3-phenoxyphenyl)methoxymethyl]benzene Chemical class C=1C=CC(OC=2C=CC=CC=2)=CC=1COCC(C=1)=CC=CC=1OC1=CC=CC=C1 XCOKKVWDJYSCRZ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- QSTXUWDNHBTZGA-UHFFFAOYSA-N 1-(1-chloro-2-methylpropan-2-yl)-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1C(C)(C)CCl QSTXUWDNHBTZGA-UHFFFAOYSA-N 0.000 description 1
- YDUREWJTLPKYER-UHFFFAOYSA-N 1-ethoxy-4-[1-[1-(4-ethoxyphenyl)-2-methylpropoxy]-2-methylpropyl]benzene Chemical compound C(C)OC1=CC=C(C=C1)C(C(C)C)OC(C(C)C)C1=CC=C(C=C1)OCC YDUREWJTLPKYER-UHFFFAOYSA-N 0.000 description 1
- JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 1
- RKLWHVUANJCSQD-UHFFFAOYSA-N 2-bromopropoxybenzene Chemical compound CC(Br)COC1=CC=CC=C1 RKLWHVUANJCSQD-UHFFFAOYSA-N 0.000 description 1
- VQUYNUJARXBNPK-UHFFFAOYSA-N 2-chloroethoxybenzene Chemical compound ClCCOC1=CC=CC=C1 VQUYNUJARXBNPK-UHFFFAOYSA-N 0.000 description 1
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
- AVFLHUZZTDDBBS-UHFFFAOYSA-N 5-chloro-5-methoxycyclohexa-1,3-diene Chemical compound COC1(Cl)CC=CC=C1 AVFLHUZZTDDBBS-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CHIWXYAWZYPFJS-UHFFFAOYSA-N bromomethoxybenzene Chemical compound BrCOC1=CC=CC=C1 CHIWXYAWZYPFJS-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58151502A JPS6045542A (ja) | 1983-08-22 | 1983-08-22 | ３−ハロゲノ−４−アルコキシネオフィルハライドの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58151502A JPS6045542A (ja) | 1983-08-22 | 1983-08-22 | ３−ハロゲノ−４−アルコキシネオフィルハライドの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6045542A JPS6045542A (ja) | 1985-03-12 |
| JPH0439449B2 true JPH0439449B2 (sv) | 1992-06-29 |
Family
ID=15519908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58151502A Granted JPS6045542A (ja) | 1983-08-22 | 1983-08-22 | ３−ハロゲノ−４−アルコキシネオフィルハライドの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6045542A (sv) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5511787A (en) * | 1990-05-04 | 1996-04-30 | The Baum Research & Development Co. | Golf club |
| US5338024A (en) * | 1990-05-04 | 1994-08-16 | The Baum Research & Development Co., Inc. | Golf club |
| JP2585338Y2 (ja) * | 1991-11-25 | 1998-11-18 | 美和ロック 株式会社 | 自動車用盗難防止装置 |
-
1983
- 1983-08-22 JP JP58151502A patent/JPS6045542A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6045542A (ja) | 1985-03-12 |
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