JPH0443055B2 - - Google Patents
Info
- Publication number
- JPH0443055B2 JPH0443055B2 JP58242152A JP24215283A JPH0443055B2 JP H0443055 B2 JPH0443055 B2 JP H0443055B2 JP 58242152 A JP58242152 A JP 58242152A JP 24215283 A JP24215283 A JP 24215283A JP H0443055 B2 JPH0443055 B2 JP H0443055B2
- Authority
- JP
- Japan
- Prior art keywords
- methylpropyl
- propene
- methyl
- halogenobenzene
- halogenophenyl
- 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 methylpropyl halide Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 7
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- GUOBCKNZNKTEHF-UHFFFAOYSA-N 1-chloro-4-(1-chloro-2-methylpropan-2-yl)benzene Chemical compound ClCC(C)(C)C1=CC=C(Cl)C=C1 GUOBCKNZNKTEHF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-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
- UTVOHQFZZCVKAP-UHFFFAOYSA-N 1-bromo-4-(1-chloro-2-methylpropan-2-yl)benzene Chemical compound ClCC(C)(C)C1=CC=C(Br)C=C1 UTVOHQFZZCVKAP-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- GRPVJBJLNJCJAZ-UHFFFAOYSA-N 1-bromo-4-(1-bromo-2-methylpropyl)benzene Chemical compound CC(C)C(Br)C1=CC=C(Br)C=C1 GRPVJBJLNJCJAZ-UHFFFAOYSA-N 0.000 description 1
- OWXJKYNZGFSVRC-UHFFFAOYSA-N 1-chloroprop-1-ene Chemical compound CC=CCl OWXJKYNZGFSVRC-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000006208 butylation Effects 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000005406 washing 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
- 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 |
|---|---|---|---|
| JP58242152A JPS60136523A (ja) | 1983-12-23 | 1983-12-23 | ２−（４−ハロゲノフエニル）−２−メチルプロピルハライドの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58242152A JPS60136523A (ja) | 1983-12-23 | 1983-12-23 | ２−（４−ハロゲノフエニル）−２−メチルプロピルハライドの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60136523A JPS60136523A (ja) | 1985-07-20 |
| JPH0443055B2 true JPH0443055B2 (de) | 1992-07-15 |
Family
ID=17085095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58242152A Granted JPS60136523A (ja) | 1983-12-23 | 1983-12-23 | ２−（４−ハロゲノフエニル）−２−メチルプロピルハライドの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60136523A (de) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56118023A (en) * | 1980-02-22 | 1981-09-16 | Kureha Chem Ind Co Ltd | Preparation of aromatic compound containing fluorine |
-
1983
- 1983-12-23 JP JP58242152A patent/JPS60136523A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56118023A (en) * | 1980-02-22 | 1981-09-16 | Kureha Chem Ind Co Ltd | Preparation of aromatic compound containing fluorine |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60136523A (ja) | 1985-07-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS61227576A (ja) | 弗素置換有機化合物およびその製法 | |
| JPS6212212B2 (de) | ||
| US4079089A (en) | Fluorination of trichloromethyl groups | |
| JP2006188531A (ja) | 新規のシアン化ハロメチルベンゾイル | |
| CS235967B2 (en) | Method of 1,1-dihalogen-1,2,2,2-tetrafluorethans production | |
| JPH06157513A (ja) | ２−アセチルベンゾ［ｂ］チオフェンの製造法 | |
| JPH0443055B2 (de) | ||
| US4093669A (en) | Method for preparing trichloromethyl-trifluoromethyl-benzenes | |
| US4335057A (en) | 4-(2',2,2'-Trihalogenoethyl)-cyclobutane-1-sulfonic acid salts with optically active bases | |
| US6580002B2 (en) | Process for the preparation of trifluoromethyl-substituted biphenylcarboxylic acids and novel trichloromethyl-and trifluoromethyl-substituted biphenylcarbonitriles | |
| JP2682820B2 (ja) | 新規４−トリフルオロメチルーベンゾイル化合物 | |
| US4210766A (en) | Process for producing 2-halo-4-bromophenols | |
| JPS60184033A (ja) | パ−フルオロアルキルブロマイドの製造方法 | |
| JPH0390057A (ja) | クロロフルオロベンゾニトリル及びその製造方法 | |
| US4783562A (en) | Process for the preparation of trichloromethyl-substituted aromatic compounds, and trichloromethyl-substituted aromatic compounds obtained in this process | |
| JP4801270B2 (ja) | 新規な含フッ素アントラセン化合物及びそれらの製造方法 | |
| US5489715A (en) | Process for preparing 4,5-difluorobenzaldehydes | |
| US5336818A (en) | Process for the preparation of substantially fluorinated alkyl bromides | |
| AU594456B2 (en) | Process for the preparation of di-ortho-substituted di-meta-halogenated para-halomethylphenols | |
| RU2152926C1 (ru) | Способ получения галогенметилбензоилцианидов | |
| JPH0225896B2 (de) | ||
| JPS61122240A (ja) | ハロゲン化された３，３‐ジメチル‐５‐ヘキセン‐２‐オンの製造方法 | |
| US5047584A (en) | Process for the preparation of pentahaloethoxy benzoyl halide compounds | |
| JPH089590B2 (ja) | ４−アルキルスルホニル−１−アルキル−２−クロルベンゼンの製法及び該化合物 | |
| JPH10168051A (ja) | ２，３−ジハロゲノ−６−トリフルオロメチルベンゾニトリルの製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |