CA1059153A - Process for the continuous preparation of trimethylolalkane allyl ethers - Google Patents
Process for the continuous preparation of trimethylolalkane allyl ethersInfo
- Publication number
- CA1059153A CA1059153A CA232,724A CA232724A CA1059153A CA 1059153 A CA1059153 A CA 1059153A CA 232724 A CA232724 A CA 232724A CA 1059153 A CA1059153 A CA 1059153A
- Authority
- CA
- Canada
- Prior art keywords
- sodium hydroxide
- trimethylolalkane
- reaction
- weight
- allyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 16
- -1 allyl ethers Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 14
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002244 precipitate Substances 0.000 claims abstract description 6
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 10
- 238000006266 etherification reaction Methods 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 claims description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 4
- 229940113165 trimethylolpropane Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000009183 running Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- LZDXRPVSAKWYDH-UHFFFAOYSA-N 2-ethyl-2-(prop-2-enoxymethyl)propane-1,3-diol Chemical compound CCC(CO)(CO)COCC=C LZDXRPVSAKWYDH-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742437789 DE2437789C3 (de) | 1974-08-06 | 1974-08-06 | Verfahren zur kontinuierlichen Herstellung von Trimethylolalkanallyläthern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1059153A true CA1059153A (en) | 1979-07-24 |
Family
ID=5922553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,724A Expired CA1059153A (en) | 1974-08-06 | 1975-08-01 | Process for the continuous preparation of trimethylolalkane allyl ethers |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5141313A (enExample) |
| AT (1) | ATA602575A (enExample) |
| BE (1) | BE832086A (enExample) |
| CA (1) | CA1059153A (enExample) |
| DE (1) | DE2437789C3 (enExample) |
| FR (1) | FR2281348A1 (enExample) |
| GB (1) | GB1473024A (enExample) |
| IT (1) | IT1041128B (enExample) |
| NL (1) | NL7509370A (enExample) |
| SE (1) | SE7508823L (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2467186A1 (fr) | 1979-10-15 | 1981-04-17 | Elf France | Alkylethers de polyols, leur preparation et leurs emplois |
| JPS60231625A (ja) * | 1984-05-02 | 1985-11-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | トリメチロ−ルプロパンのアリルエ−テル化物の製法 |
| JPS60233026A (ja) * | 1984-05-02 | 1985-11-19 | Nippon Shokubai Kagaku Kogyo Co Ltd | トリメチロ−ルプロパンのアリルエ−テル化物の製造法 |
| JPS60252440A (ja) * | 1984-05-29 | 1985-12-13 | Nippon Shokubai Kagaku Kogyo Co Ltd | トリメチロ−ルプロパンのジアリルエ−テルの製造方法 |
| CN1052970C (zh) * | 1996-06-04 | 2000-05-31 | 中国石化齐鲁石油化工公司 | 一种多元醇烯丙基醚的制备方法 |
| SE520970C2 (sv) * | 1998-09-30 | 2003-09-16 | Perstorp Ab | Förfarande vid utvinning av trimethylolpropantriallyleter eller -diallyleter |
| EP1514861B1 (en) * | 2002-06-07 | 2007-09-12 | Daiso Co., Ltd. | Process for producing allyl ether |
| CN102040486B (zh) * | 2010-11-24 | 2013-03-13 | 山东省化工研究院 | 三羟甲基丙烷二烯丙基醚的制备方法 |
-
1974
- 1974-08-06 DE DE19742437789 patent/DE2437789C3/de not_active Expired
-
1975
- 1975-08-01 CA CA232,724A patent/CA1059153A/en not_active Expired
- 1975-08-04 IT IT5080075A patent/IT1041128B/it active
- 1975-08-04 BE BE158911A patent/BE832086A/xx unknown
- 1975-08-04 JP JP9428575A patent/JPS5141313A/ja active Pending
- 1975-08-04 AT AT602575A patent/ATA602575A/de not_active Application Discontinuation
- 1975-08-05 SE SE7508823A patent/SE7508823L/xx not_active Application Discontinuation
- 1975-08-05 GB GB3269075A patent/GB1473024A/en not_active Expired
- 1975-08-06 FR FR7524557A patent/FR2281348A1/fr active Granted
- 1975-08-06 NL NL7509370A patent/NL7509370A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2437789C3 (de) | 1980-03-20 |
| FR2281348B1 (enExample) | 1979-01-05 |
| DE2437789A1 (de) | 1976-02-19 |
| ATA602575A (de) | 1977-04-15 |
| NL7509370A (nl) | 1976-02-10 |
| IT1041128B (it) | 1980-01-10 |
| JPS5141313A (ja) | 1976-04-07 |
| DE2437789B2 (de) | 1979-06-21 |
| SE7508823L (sv) | 1976-02-09 |
| FR2281348A1 (fr) | 1976-03-05 |
| BE832086A (fr) | 1976-02-04 |
| GB1473024A (en) | 1977-05-11 |
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