JPS5982343A - キシリルアクリレ−トまたはキシリルメタクリレ−トの製造法 - Google Patents
キシリルアクリレ−トまたはキシリルメタクリレ−トの製造法Info
- Publication number
- JPS5982343A JPS5982343A JP57191938A JP19193882A JPS5982343A JP S5982343 A JPS5982343 A JP S5982343A JP 57191938 A JP57191938 A JP 57191938A JP 19193882 A JP19193882 A JP 19193882A JP S5982343 A JPS5982343 A JP S5982343A
- Authority
- JP
- Japan
- Prior art keywords
- xylyl
- acrylate
- alkali metal
- oil phase
- 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
- -1 xylyl acrylate Chemical compound 0.000 title claims abstract description 46
- 239000012071 phase Substances 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 18
- 239000008346 aqueous phase Substances 0.000 claims abstract description 18
- NVLHGZIXTRYOKT-UHFFFAOYSA-N 1-chloro-2,3-dimethylbenzene Chemical compound CC1=CC=CC(Cl)=C1C NVLHGZIXTRYOKT-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000007864 aqueous solution Substances 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 12
- 239000011541 reaction mixture Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 5
- 239000012736 aqueous medium Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 13
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract description 2
- 229920003002 synthetic resin Polymers 0.000 abstract description 2
- 239000000057 synthetic resin Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 229940048053 acrylate Drugs 0.000 description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 24
- 125000005023 xylyl group Chemical group 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- SYOAEJBDXDTKGC-UHFFFAOYSA-N (2,3-dimethylphenyl) prop-2-enoate Chemical compound CC1=CC=CC(OC(=O)C=C)=C1C SYOAEJBDXDTKGC-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- VQRBXYBBGHOGFT-UHFFFAOYSA-N 1-(chloromethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CCl VQRBXYBBGHOGFT-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000006839 xylylene group Chemical group 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 229940047670 sodium acrylate Drugs 0.000 description 2
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IWNLRYHTRXHMJE-UHFFFAOYSA-M Cl(=O)[O-].C(CCCCCCCCCCC)[N+](C)(C)CC1=CC=CC=C1 Chemical compound Cl(=O)[O-].C(CCCCCCCCCCC)[N+](C)(C)CC1=CC=CC=C1 IWNLRYHTRXHMJE-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 241000609816 Pantholops hodgsonii Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001504592 Trachurus trachurus Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 1
- FADYGXGJTNYCHZ-UHFFFAOYSA-M benzyl-dodecyl-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](CC)(CC)CC1=CC=CC=C1 FADYGXGJTNYCHZ-UHFFFAOYSA-M 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- PDSBZVAAFJAPFK-UHFFFAOYSA-N dibutyl(diphenyl)azanium Chemical compound C=1C=CC=CC=1[N+](CCCC)(CCCC)C1=CC=CC=C1 PDSBZVAAFJAPFK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- AYLBVKUPVXVTSO-UHFFFAOYSA-N n,n-diphenylnitramide Chemical compound C=1C=CC=CC=1N([N+](=O)[O-])C1=CC=CC=C1 AYLBVKUPVXVTSO-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000002351 wastewater 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 |
|---|---|---|---|
| JP57191938A JPS5982343A (ja) | 1982-11-02 | 1982-11-02 | キシリルアクリレ−トまたはキシリルメタクリレ−トの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57191938A JPS5982343A (ja) | 1982-11-02 | 1982-11-02 | キシリルアクリレ−トまたはキシリルメタクリレ−トの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5982343A true JPS5982343A (ja) | 1984-05-12 |
| JPH0234338B2 JPH0234338B2 (enrdf_load_stackoverflow) | 1990-08-02 |
Family
ID=16282948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57191938A Granted JPS5982343A (ja) | 1982-11-02 | 1982-11-02 | キシリルアクリレ−トまたはキシリルメタクリレ−トの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5982343A (enrdf_load_stackoverflow) |
-
1982
- 1982-11-02 JP JP57191938A patent/JPS5982343A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0234338B2 (enrdf_load_stackoverflow) | 1990-08-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2801330B2 (ja) | メタクリロキシ基又はアクリロキシ基を含むオルガノシランの製法 | |
| AU2012228866B2 (en) | Preparation method of carfentrazone-ethyl | |
| JPS6213345B2 (enrdf_load_stackoverflow) | ||
| JPS5982343A (ja) | キシリルアクリレ−トまたはキシリルメタクリレ−トの製造法 | |
| US3759985A (en) | Method for preparing salts of sulfoalkyl esters | |
| JP3467307B2 (ja) | ホスホニウム塩の製造方法 | |
| JPS5933584B2 (ja) | 置換ベンジルニトリル誘導体 | |
| US7115771B2 (en) | Process for producing fluorine-containing alkylsulfonylaminoethyl α-substituted acrylate | |
| JPS6241662B2 (enrdf_load_stackoverflow) | ||
| JP5242873B2 (ja) | フッ化アルキルアミン化合物の製造方法 | |
| JPH0585968A (ja) | ヒドロゲンペルフルオロアルカンの合成 | |
| JPS5978145A (ja) | キシリレンジアクリレ−トまたはキシリレンジメタクリレ−トの製造法 | |
| JPS60184033A (ja) | パ−フルオロアルキルブロマイドの製造方法 | |
| JP2002316956A (ja) | パーフルオロアルキルアイオダイドテロマーの製造方法 | |
| JP2886990B2 (ja) | 不飽和第四級アンモニウム塩の製造方法 | |
| JP2819502B2 (ja) | 大部分がフルオル化されたアルキルプロミドの製造方法 | |
| JPS5980631A (ja) | キシリレンジアクリレ−トまたはキシリレンジメタクリレ−トの製造方法 | |
| JPH045007B2 (enrdf_load_stackoverflow) | ||
| JP2009256305A (ja) | 含フッ素カルボン酸エステルの製造方法 | |
| JP6124015B2 (ja) | ペンタフルオロスルファニル安息香酸の製造方法 | |
| EP0465294B1 (fr) | Procédé de fabrication de bromures insaturés | |
| JP3624478B2 (ja) | ポリフルオロアルキルエステル化合物の製造方法 | |
| JP2971523B2 (ja) | トリアリルイソシアヌレートの製造法 | |
| JPH02172969A (ja) | ジチオールジ（メタ）アクリレートの製造法 | |
| JP3149537B2 (ja) | １ｈ−ペルフルオロアルカンの製造法 |