DE2437789C3 - Verfahren zur kontinuierlichen Herstellung von Trimethylolalkanallyläthern - Google Patents
Verfahren zur kontinuierlichen Herstellung von TrimethylolalkanallyläthernInfo
- Publication number
- DE2437789C3 DE2437789C3 DE19742437789 DE2437789A DE2437789C3 DE 2437789 C3 DE2437789 C3 DE 2437789C3 DE 19742437789 DE19742437789 DE 19742437789 DE 2437789 A DE2437789 A DE 2437789A DE 2437789 C3 DE2437789 C3 DE 2437789C3
- Authority
- DE
- Germany
- Prior art keywords
- trimethylolalkane
- reaction
- continuous production
- sodium hydroxide
- allyl ethers
- 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 description 13
- -1 allyl ethers Chemical class 0.000 title claims description 3
- 238000010924 continuous production Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 125000002061 L-isoleucyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])[C@](C([H])([H])[H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 238000010533 azeotropic distillation Methods 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
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000007306 turnover Effects 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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742437789 DE2437789C3 (de) | 1974-08-06 | 1974-08-06 | Verfahren zur kontinuierlichen Herstellung von Trimethylolalkanallyläthern |
| CA232,724A CA1059153A (en) | 1974-08-06 | 1975-08-01 | Process for the continuous preparation of trimethylolalkane allyl ethers |
| IT5080075A IT1041128B (it) | 1974-08-06 | 1975-08-04 | Procedimento per produrre in continuo eteri trimetilolalcanal lilici |
| BE158911A BE832086A (fr) | 1974-08-06 | 1975-08-04 | Procede de fabrication en continu d'ethers allyliques de trimethylolalcanes |
| JP9428575A JPS5141313A (ja) | 1974-08-06 | 1975-08-04 | Torimechirooruarukanarirueeteruno renzokuseizohoho |
| AT602575A ATA602575A (de) | 1974-08-06 | 1975-08-04 | Verfahren zur kontinuierlichen herstellung von trimethylolalkanallylathern |
| GB3269075A GB1473024A (en) | 1974-08-06 | 1975-08-05 | Process for the continuous preparation of trimethylol-alkane allyl ethers |
| SE7508823A SE7508823L (sv) | 1974-08-06 | 1975-08-05 | Sett for kontinuerlig framstellning av trimetylolalkanallyletrar. |
| FR7524557A FR2281348A1 (fr) | 1974-08-06 | 1975-08-06 | Procede de fabrication en continu d'ethers allyliques de trimethylolalcanes |
| NL7509370A NL7509370A (nl) | 1974-08-06 | 1975-08-06 | Werkwijze voor de continue bereiding van trimethylolalkaanallylethers. |
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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2437789A1 DE2437789A1 (de) | 1976-02-19 |
| DE2437789B2 DE2437789B2 (de) | 1979-06-21 |
| DE2437789C3 true DE2437789C3 (de) | 1980-03-20 |
Family
ID=5922553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742437789 Expired DE2437789C3 (de) | 1974-08-06 | 1974-08-06 | Verfahren zur kontinuierlichen Herstellung von Trimethylolalkanallyläthern |
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 |
|---|---|
| FR2281348B1 (enExample) | 1979-01-05 |
| DE2437789A1 (de) | 1976-02-19 |
| CA1059153A (en) | 1979-07-24 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |