JPH02258734A - １，８―ビス（２―ハロゲノエチル）ナフタレンとその製造方法 - Google Patents
１，８―ビス（２―ハロゲノエチル）ナフタレンとその製造方法Info
- Publication number
- JPH02258734A JPH02258734A JP7932989A JP7932989A JPH02258734A JP H02258734 A JPH02258734 A JP H02258734A JP 7932989 A JP7932989 A JP 7932989A JP 7932989 A JP7932989 A JP 7932989A JP H02258734 A JPH02258734 A JP H02258734A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- naphthalene
- formula
- halogenoethyl
- reaction
- 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.)
- Granted
Links
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- NYFZLYHJRSCBJK-UHFFFAOYSA-N 1,8-bis(2-bromoethyl)naphthalene Chemical compound C1=CC(CCBr)=C2C(CCBr)=CC=CC2=C1 NYFZLYHJRSCBJK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- NTAAJJCJYRBUBY-UHFFFAOYSA-N 2-[8-(2-hydroxyethyl)naphthalen-1-yl]ethanol Chemical compound C1=CC(CCO)=C2C(CCO)=CC=CC2=C1 NTAAJJCJYRBUBY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- COIBFCUQUWJKEN-UHFFFAOYSA-N 1-(2-chloroethyl)naphthalene Chemical compound C1=CC=C2C(CCCl)=CC=CC2=C1 COIBFCUQUWJKEN-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- FTUDIUREWUBVKL-UHFFFAOYSA-N 1,8-bis(ethenyl)naphthalene Chemical compound C1=CC(C=C)=C2C(C=C)=CC=CC2=C1 FTUDIUREWUBVKL-UHFFFAOYSA-N 0.000 abstract description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 2
- VHAXQSFPTJUMLT-UHFFFAOYSA-N bis(3-methylbutan-2-yl)boron Chemical compound CC(C)C(C)[B]C(C)C(C)C VHAXQSFPTJUMLT-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005658 halogenation reaction Methods 0.000 abstract description 2
- 238000006197 hydroboration reaction Methods 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 229920000570 polyether Polymers 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 230000026030 halogenation Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- -1 1,8-bis(2-chloroethyl)naphthalene Chemical compound 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000006416 CBr Chemical group BrC* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 235000006545 Ziziphus mauritiana Nutrition 0.000 description 1
- 240000000038 Ziziphus mauritiana Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7932989A JPH02258734A (ja) | 1989-03-30 | 1989-03-30 | １，８―ビス（２―ハロゲノエチル）ナフタレンとその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7932989A JPH02258734A (ja) | 1989-03-30 | 1989-03-30 | １，８―ビス（２―ハロゲノエチル）ナフタレンとその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02258734A true JPH02258734A (ja) | 1990-10-19 |
| JPH0420896B2 JPH0420896B2 (enrdf_load_stackoverflow) | 1992-04-07 |
Family
ID=13686845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7932989A Granted JPH02258734A (ja) | 1989-03-30 | 1989-03-30 | １，８―ビス（２―ハロゲノエチル）ナフタレンとその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02258734A (enrdf_load_stackoverflow) |
-
1989
- 1989-03-30 JP JP7932989A patent/JPH02258734A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0420896B2 (enrdf_load_stackoverflow) | 1992-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |