JPS6244538B2 - - Google Patents
Info
- Publication number
- JPS6244538B2 JPS6244538B2 JP17147480A JP17147480A JPS6244538B2 JP S6244538 B2 JPS6244538 B2 JP S6244538B2 JP 17147480 A JP17147480 A JP 17147480A JP 17147480 A JP17147480 A JP 17147480A JP S6244538 B2 JPS6244538 B2 JP S6244538B2
- Authority
- JP
- Japan
- Prior art keywords
- diacrylate
- bmepp
- propane
- bis
- benzene
- 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
Links
- 125000004386 diacrylate group Chemical group 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 28
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000013078 crystal Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 241001550224 Apha Species 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000012535 impurity Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000001294 propane Substances 0.000 description 5
- -1 2,2-bis(4- Methacryloxydiisopropoxyphenyl)propane Chemical compound 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- VIYWVRIBDZTTMH-UHFFFAOYSA-N 2-[4-[2-[4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCCOC(=O)C(C)=C)C=C1 VIYWVRIBDZTTMH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JZOBIVDRMAPQDS-UHFFFAOYSA-N 2-[2,6-dibromo-4-[2-[3,5-dibromo-4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=C(Br)C(OCCOC(=O)C(=C)C)=C(Br)C=C1C(C)(C)C1=CC(Br)=C(OCCOC(=O)C(C)=C)C(Br)=C1 JZOBIVDRMAPQDS-UHFFFAOYSA-N 0.000 description 1
- SJSRCGZBJFXXSA-UHFFFAOYSA-N 2-[2,6-dichloro-4-[2-[3,5-dichloro-4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=C(Cl)C(OCCOC(=O)C(=C)C)=C(Cl)C=C1C(C)(C)C1=CC(Cl)=C(OCCOC(=O)C(C)=C)C(Cl)=C1 SJSRCGZBJFXXSA-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MYMLQDROXQYBMM-UHFFFAOYSA-N [2,6-dichloro-4-[2-[3,5-dichloro-4-(2-methylprop-2-enoyloxy)phenyl]propan-2-yl]phenyl] 2-methylprop-2-enoate Chemical compound C1=C(Cl)C(OC(=O)C(=C)C)=C(Cl)C=C1C(C)(C)C1=CC(Cl)=C(OC(=O)C(C)=C)C(Cl)=C1 MYMLQDROXQYBMM-UHFFFAOYSA-N 0.000 description 1
- NUJYRWXNUFEUHQ-UHFFFAOYSA-N [4-[2-[4-(2-methylprop-2-enoyloxy)-2-propan-2-yloxyphenyl]propan-2-yl]-3-propan-2-yloxyphenyl] 2-methylprop-2-enoate Chemical compound CC(C)OC1=CC(OC(=O)C(C)=C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1OC(C)C NUJYRWXNUFEUHQ-UHFFFAOYSA-N 0.000 description 1
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000005548 dental material Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17147480A JPS5795941A (en) | 1980-12-06 | 1980-12-06 | Purifying method of diacrylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17147480A JPS5795941A (en) | 1980-12-06 | 1980-12-06 | Purifying method of diacrylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5795941A JPS5795941A (en) | 1982-06-15 |
| JPS6244538B2 true JPS6244538B2 (fr) | 1987-09-21 |
Family
ID=15923768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17147480A Granted JPS5795941A (en) | 1980-12-06 | 1980-12-06 | Purifying method of diacrylate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5795941A (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH048517U (fr) * | 1990-05-10 | 1992-01-27 | ||
| JP2010064988A (ja) * | 2008-09-11 | 2010-03-25 | Toagosei Co Ltd | 多官能（メタ）アクリレートの製造方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3342601C1 (de) * | 1983-11-25 | 1985-03-14 | Blendax-Werke R. Schneider Gmbh & Co, 6500 Mainz | Verwendung von bromierten aromatischen Diacrylsaeure- bzw. Dimethacrylsaeureestern in dentalen Fuellungsmaterialien |
| US4603350A (en) * | 1984-12-21 | 1986-07-29 | Rca Corporation | Interlaced digital video input filter/decimator and/or expander/interpolator filter |
-
1980
- 1980-12-06 JP JP17147480A patent/JPS5795941A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH048517U (fr) * | 1990-05-10 | 1992-01-27 | ||
| JP2010064988A (ja) * | 2008-09-11 | 2010-03-25 | Toagosei Co Ltd | 多官能（メタ）アクリレートの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5795941A (en) | 1982-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH03200753A (ja) | 光学純度の高い光学活性アテノロール塩及びアテノロールの製法 | |
| US4511722A (en) | Process for preparing cyclic N-vinylacylamines | |
| JP4456939B2 (ja) | アダマンチルエステル類の精製方法 | |
| JPS6244538B2 (fr) | ||
| JPS6322540A (ja) | ４−ハイドロキシフエニル４−ハイドロキシベンゾエ−トの製法 | |
| JPS5918378B2 (ja) | アクリル酸若しくはメタクリル酸又はそれらのエステル類の重合禁止方法 | |
| JP2001226323A (ja) | 安息香酸ベンジルの回収方法 | |
| CN113330002A (zh) | 用于在水性介质中制备1,4-脱水山梨糖醇的方法 | |
| JPS6312462B2 (fr) | ||
| JPH02129163A (ja) | 不飽和カルボン酸−２−イソシアナトアルキルエステルの製造方法 | |
| JPH08295646A (ja) | ビス（ヒドロキシエトキシフェニル）化合物の製造方法 | |
| JP3640319B2 (ja) | ベンズアミド誘導体の製造方法 | |
| JP3022008B2 (ja) | トリスフェノール類のｔ−ブトキシカーボネートの混合物からなる組成物 | |
| JPS6218539B2 (fr) | ||
| AU2016215954B2 (en) | Method for producing 2-aminoethylmethacrylate hydrochloride | |
| JPS63130564A (ja) | ベンゾイルアクリル酸エステル類の製造法 | |
| JP2909571B2 (ja) | 高純度ベンゼンの製造方法 | |
| JPS62123161A (ja) | 新規ｎ，ｎ，ｎ′，ｎ′−テトラシクロヘキシル−ジカルボン酸ジアミド | |
| JP2514001B2 (ja) | アセチンの製造方法 | |
| JPH07157451A (ja) | 非対称ジエステルの製造方法 | |
| JPH0632768A (ja) | 不飽和第４級アンモニウム塩の製法 | |
| JPH03190856A (ja) | 精製ヒドロペルオキシドの製造方法 | |
| JPS6322557A (ja) | アシル化複素環化合物の製造方法 | |
| JPH01258678A (ja) | ヒドロキシフェニルプロピオン酸エステルの製造法 | |
| JPH0248559A (ja) | 不飽和カルボン酸アミドの製造方法 |