CH341805A - Process for the production of ethers or thioethers - Google Patents
Process for the production of ethers or thioethersInfo
- Publication number
- CH341805A CH341805A CH341805DA CH341805A CH 341805 A CH341805 A CH 341805A CH 341805D A CH341805D A CH 341805DA CH 341805 A CH341805 A CH 341805A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- hours
- styrene oxide
- ethers
- production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000002170 ethers Chemical class 0.000 title claims description 4
- 150000003568 thioethers Chemical class 0.000 title claims description 4
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- XWCQSILTDPAWDP-UHFFFAOYSA-N 2-chloro-1-phenylethanol Chemical compound ClCC(O)C1=CC=CC=C1 XWCQSILTDPAWDP-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- -1 vinyl halides Chemical class 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/16—Aryl or aralkyl ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/16—Aryl or aralkyl ethers
- C08B11/18—Aryl or aralkyl ethers with substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/08—Ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung von Äthern bzw. Thioäthern
Es ist bekannt, dass sich Styroloxyd mit einer Reihe von Verbindungen umsetzen kann. Bereits beschrieben ist die Umsetzung von Styroloxyd mit Ammoniak und Aminen, mit einwertigen Alkoholen, mit Phenol, mit Mercaptanen, mit Keto-Enol-Verbindungen, mit Vinylhalogeniden, mit Natrium-Me- thylat, mit Maleinsäureanhydrid, mit organischen Säuren oder ihren Anhydriden, mit Pyridin und andern organischen Basen, mit Allylalkohol, mit 2 Naphthol und mit 4-Vinyl-cyclohexen-dioxyd.
Es wurde nun gefunden, dass Verbindungen, die mindestens zwei alkoholische OH-bzw. SH-Gruppen enthalten, mit Styroloxyd zu wertvollen Athern bzw.
Thioäthern veräthert werden können.
Die Reaktion wird vorteilhafterweise in der Weise durchgeführt, dass man Styroloxyd in mindestens äquimolekularem Verhältnis mit der zweiten Kom- ponente zusammen erwärmt. Bei der Kondensation von Hydroxylverbindungen mit Styroloxyd ist dabei die Verwendung eines alkalischen Katalysators, wie Ätzkali oder Ätznatron, vorteilhaft.
Die Reaktionsbedingungen hängen von der Re aktionsfähigkeit der verwendeten Ausgangssubstanz ab. In manchen Fällen ist es notwendig, in geschlossenem Gefäss mehrere Stunden unter Druck zu erhitzen.
Die Reaktionsprodukte können als Zwischenprodukte für die Herstellung von Farbstoffen, Kunststoffen, Textilhilfsmitteln oder Arzneimitteln verwendet werden. Bei Verwendung überschüssigen Styroloxyds werden die Produkte in steigendem Masse hydrophil und in Wasser löslich bzw. dispergierbar.
Das Styroloxyd kann man im Reaktionsgefäss aus Styrolchlorhydrin in Gegenwart der berechneten Menge einer chlorwasserstoffbindenden Substanz, wie NaOH oder KOH, entstehen lassen.
Beispiele
1. 100 Teile Polyvinylalkohol werden zusammen mit 500 Teilen Styroloxyd auf 80 C erwärmt. Bei dieser Ternperatur tritt eine stürmische Reaktion ein unter Bildung einer gummiartigen, braunen Masse.
2. 100 Teile Polyvinylalkohol werden zusammen mit 500 Teilen Styroloxyd und 5 Teilen Natronlauge während mehreren Stunden auf 60"C gehalten. Es entsteht eine gallertartige, weisse Masse.
3. 100 Teile Cellulose werden zusammen mit 500 Teilen Styroloxyd und 5 Teilen Natronlauge während mehreren Stunden auf 180 C gehalten. Es entsteht eine viskose, gelartige Masse.
4. 108 Teile Trimethylenthioglykol und 118 Teile Styroloxyd wurden in einem Autoklaven 15 Stunden auf 180 C erhitzt. Das Reaktionsprodukt stellt ein viskoses 01 dar.
Weitere Ausführungsbeispiele sind in nachfolgender Tabelle zusammengestellt.
Teile
L¯slichkeiten
Substanz Substanz Reaktions- Reaktions- Katalysator Reaktionsprodukt in pro Teil temperatur dauer
Styroloxyd H2O Alkohol Glykol 0, 5 Teile 190 C 10 Stunden farblose Flüssigkeit s.
Glykol 0, 5 Teile 130 C 5 Stunden KOH O1 0 s.
Trimethylenglykol 0, 2 Teile 1600 C 12 Stunden 61 s.
Trimethylenglykol 0, 2 Teile 150 C 6 Stunden KOH zähes Íl s.
Glycerin 0, 3 Teile 160 C 6 Stunden NaOH farbloser Sirup 0 s.
Glycerin 0, 3 Teile 150 C 6 Stunden NaOH dicker klarer Sirup s.
Pentaerythrit 0, 2 Teile 110 C 5 Stunden NaOH klares klebriges Harz s.
Pentaerythrit 0, 2 Teile 110 C 6 Stunden p-Toluyl-klares klebriges Harz s. säure Pentaerythrit 0, 2 Teile 110 C 5 Stunden H2SO4 klares klebriges Harz s.
Sorbit 0, 2 Teile 150 C 6 Stunden NaOH glasiges Harz zip s.
Stärke 0, 2 Teile 150 C 8 Stunden NaOH körnige Masse s.) Cellulose 0, 2 Teile 180 C 6 Stunden NaOH zähes Gel s.
Polyvinylalkohol 0, 2 Teile 80 C 5 Stunden gummiartige Masse)( Polyvinylalkohol 0,2 Teile 60¯ C 5 Stunden NaOH durchsichtiges Gel
Die Löslichkeiten in vorstehender Tabelle bedeuten : 0 = unlöslich s. = sehr gut löslich
Process for the production of ethers or thioethers
It is known that styrene oxide can react with a number of compounds. The reaction of styrene oxide with ammonia and amines, with monohydric alcohols, with phenol, with mercaptans, with keto-enol compounds, with vinyl halides, with sodium methylate, with maleic anhydride, with organic acids or their anhydrides, has already been described Pyridine and other organic bases, with allyl alcohol, with 2 naphthol and with 4-vinyl-cyclohexene-dioxide.
It has now been found that compounds containing at least two alcoholic OH- or. SH groups contain, with styrene oxide to valuable ethers or
Thioethers can be etherified.
The reaction is advantageously carried out in such a way that styrene oxide is heated together with the second component in at least an equimolecular ratio. When condensing hydroxyl compounds with styrene oxide, it is advantageous to use an alkaline catalyst such as caustic potash or caustic soda.
The reaction conditions depend on the reactivity of the starting substance used. In some cases it is necessary to heat for several hours under pressure in a closed vessel.
The reaction products can be used as intermediate products for the production of dyes, plastics, textile auxiliaries or pharmaceuticals. When using excess styrene oxide, the products become increasingly hydrophilic and soluble or dispersible in water.
The styrene oxide can be formed in the reaction vessel from styrene chlorohydrin in the presence of the calculated amount of a substance that binds hydrogen chloride, such as NaOH or KOH.
Examples
1. 100 parts of polyvinyl alcohol are heated to 80 C together with 500 parts of styrene oxide. At this temperature a stormy reaction occurs with the formation of a rubbery, brown mass.
2. 100 parts of polyvinyl alcohol, together with 500 parts of styrene oxide and 5 parts of sodium hydroxide solution, are kept at 60 ° C. for several hours. A gelatinous, white mass is formed.
3. 100 parts of cellulose, together with 500 parts of styrene oxide and 5 parts of sodium hydroxide solution, are kept at 180 ° C. for several hours. A viscous, gel-like mass is created.
4. 108 parts of trimethylene thioglycol and 118 parts of styrene oxide were heated to 180 ° C. in an autoclave for 15 hours. The reaction product is a viscous oil.
Further exemplary embodiments are compiled in the table below.
Parts
Solubilities
Substance substance reaction reaction catalyst reaction product in per part temperature duration
Styrene oxide H2O alcohol glycol 0, 5 parts 190 C 10 hours colorless liquid s.
Glycol 0.5 parts 130 C 5 hours KOH O1 0 s.
Trimethylene glycol 0.2 parts 1600 C 12 hours 61 s.
Trimethylene glycol 0.2 parts 150 C 6 hours KOH viscous oil s.
Glycerin 0.3 parts 160 ° C. 6 hours NaOH colorless syrup 0 s.
Glycerin 0.3 parts 150 C 6 hours NaOH thick clear syrup s.
Pentaerythritol 0.2 parts 110 ° C. 5 hours NaOH clear sticky resin s.
Pentaerythritol 0.2 parts 110C for 6 hours p-toluyl-clear sticky resin s. acid pentaerythritol 0.2 parts 110 C 5 hours H2SO4 clear sticky resin s.
Sorbitol 0.2 parts 150 C 6 hours NaOH glassy resin zip s.
Starch 0.2 parts 150 C 8 hours NaOH granular mass see) Cellulose 0.2 parts 180 C 6 hours NaOH tough gel see.
Polyvinyl alcohol 0.2 parts 80 C 5 hours gummy mass) (polyvinyl alcohol 0.2 parts 60¯ C 5 hours NaOH transparent gel
The solubilities in the table above mean: 0 = insoluble s. = very soluble
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE341805X | 1953-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH341805A true CH341805A (en) | 1959-10-31 |
Family
ID=6235915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH341805D CH341805A (en) | 1953-10-02 | 1954-10-02 | Process for the production of ethers or thioethers |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH341805A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384167A1 (en) * | 1989-01-31 | 1990-08-29 | Union Carbide Chemicals And Plastics Company, Inc. | Polysaccharides with alkaryl or aralkyl hydrophobes and latex compositions containing same |
| US5504123A (en) * | 1994-12-20 | 1996-04-02 | Union Carbide Chemicals & Plastics Technology Corporation | Dual functional cellulosic additives for latex compositions |
-
1954
- 1954-10-02 CH CH341805D patent/CH341805A/en unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384167A1 (en) * | 1989-01-31 | 1990-08-29 | Union Carbide Chemicals And Plastics Company, Inc. | Polysaccharides with alkaryl or aralkyl hydrophobes and latex compositions containing same |
| US6372901B1 (en) | 1989-01-31 | 2002-04-16 | Union Carbide Corporation | Polysaccharides with alkyl-aryl hydrophobes and latex compositions containing same |
| US6372902B1 (en) | 1989-01-31 | 2002-04-16 | Union Carbide Corporation | Process for preparing polysaccharides with alkyl-aryl hydrophobes and latex compositions containing same |
| US5504123A (en) * | 1994-12-20 | 1996-04-02 | Union Carbide Chemicals & Plastics Technology Corporation | Dual functional cellulosic additives for latex compositions |
| US5583214A (en) * | 1994-12-20 | 1996-12-10 | Union Carbide Chemicals & Plastics Technology Corporation | Dual functional cellulosic additives for latex compositions |
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