DE580075C - Process for the production of glycol monoalkyl ethers - Google Patents
Process for the production of glycol monoalkyl ethersInfo
- Publication number
- DE580075C DE580075C DEC36943D DEC0036943D DE580075C DE 580075 C DE580075 C DE 580075C DE C36943 D DEC36943 D DE C36943D DE C0036943 D DEC0036943 D DE C0036943D DE 580075 C DE580075 C DE 580075C
- Authority
- DE
- Germany
- Prior art keywords
- monoalkyl ethers
- ethylene oxide
- glycol monoalkyl
- production
- parts
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- -1 glycol monoalkyl ethers Chemical class 0.000 title description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 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 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHES REICHGERMAN EMPIRE
AUSGEGEBEN AM
5.JULI1933ISSUED ON
JULY 5, 1933
REICHSPATENTAMTREICH PATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
ΛΙ 580075 KLASSE 12 ο GRUPPE 5ΛΙ 580075 CLASS 12 ο GROUP 5
I. G. Farbenindustrie Akt.-Ges. in Frankfurt a. M.*) Verfahren zur Herstellung von GlykolmonoalkyläthernI. G. Farbenindustrie Akt.-Ges. in Frankfurt a. M. *) Process for the production of glycol monoalkyl ethers
Patentiert im Deutschen Reiche vom 14. Juli 1925 abPatented in the German Empire on July 14, 1925
Man hat schon Glykolmonoäthyläther durch Umsetzung von Äthylenoxyd mit Äthylalkohol in der Hitze hergestellt, doch verläuft diese Umsetzung sehr kompliziert. Auch durch Umsetzung von Äthylenoxyd mit äquimolekularen Mengen Natriumalkohol at kann man Glykolmonoäthyläther herstellen, doch ist ein solches Verfahren nicht wirtschaftlich. Man hat ferner bei der Umsetzung von Wasser mit Äthylenoxyd schon verdünnte Säuren als Katalysatoren verwendet.One already has glycol monoethyl ether by reacting ethylene oxide with ethyl alcohol produced in the heat, but this implementation is very complicated. Also by reacting ethylene oxide with equimolecular ones Glycol monoethyl ether can be produced in quantities of sodium alcohol, but such a process is not economical. The reaction of water with ethylene oxide also results in dilute acids used as catalysts.
Es wurde nun gefunden, daß man Glykolmonoalkyläther sehr vorteilhaft herstellen kann, wenn man die Umsetzung des Äthylenoxyds mit möglichst wasserarmen Alkoholen, d. h. solchen mit einem Wassergehalt von nicht mehr als etwa 4 Volumprozent, in Gegenwart geringer Mengen starker Säuren, wie Schwefelsäure, Phosphorsäure, Sulfonsäuren u. dgl., als Katalysatoren vornimmt. Auf diese Weise gelingt es, die Glykolmonoalkyläther in sehr einfacher Weise und in vorzüglicher Ausbeute herzustellen.It has now been found that glycol monoalkyl ethers can be produced very advantageously can, if you implement the ethylene oxide with alcohols that are as low in water as possible, d. H. those with a water content of no more than about 4 percent by volume, in the presence of small amounts of strong acids, such as sulfuric acid, phosphoric acid, sulfonic acids and the like, as catalysts. In this way it is possible to use the glycol monoalkyl ethers in a very simple manner and in produce excellent yield.
Man vermischt 1300 Gewichtsteile möglichst wasserarmen Äthylalkohols mit 30 Gewichtsteilen 96°/0iger Schwefelsäure und leitet 132 Gewichtsteile Äthylenoxyd in diese Mischung ein. Die Temperatur steigt dabei auf 6o°. Nach dem Einleiten kocht man noch 6 Stunden unter Rückfluß, neutralisiert die Schwefelsäure mit Natriumcarbonat und destilliert den Alkohol ab. Es hinterbleiben 195 Gewichtsteile Glykolmonoäthyläther, während der nicht umgesetzte Teil des Äthylenoxyds sich in dem abdestillierten Alkohol wiederfindet und im nächsten Arbeitsgang mit ausgenutzt wird.Mixing 1300 parts by weight of water-poor as possible with 30 parts by weight ethyl alcohol 96 ° / 0 sulfuric acid and 132 parts by weight of ethylene oxide passes into this mixture a. The temperature rises to 60 °. After the introduction, the mixture is refluxed for a further 6 hours, the sulfuric acid is neutralized with sodium carbonate and the alcohol is distilled off. 195 parts by weight of glycol monoethyl ether remain, while the unreacted part of the ethylene oxide is found in the alcohol which has been distilled off and is also used in the next operation.
Man löst 50 Teile kristallisierte Phosphorsäure in 1400 Teilen 98°/0igem Äthylalkohol und leitet in diese Lösung bei Siedetemperatür Äthylenoxyd ein. Dann kocht man noch 3 bis 4 Stunden unter Rückfluß, neutralisiert die Phosphorsäure mit Soda und destilliert den Alkohol ab. Es hinterbleiben Glykolmonoäthyläther und geringe Mengen Polyäthylenglykolmonoäthyläther. Dissolve 50 parts of crystallized phosphoric acid in 1400 parts of 98 ° / 0 sodium ethyl alcohol and initiates in this solution at Siedetemperatür ethylene oxide. The mixture is then refluxed for a further 3 to 4 hours, the phosphoric acid is neutralized with soda and the alcohol is distilled off. Glycol monoethyl ether and small amounts of polyethylene glycol monoethyl ether remain.
B e i s ρ i el 3B e i s ρ i el 3
Man löst 30 Teile /J-Naphthalinsulfonsäure in 1400 Teilen wasserfreiem Methylalkohol und leitet in diese Mischung bei Siedetemperatur Äthylenoxyd ein. Dann behandelt man weiter, wie in Beispiel 2 angegeben. In ähnlicher Weise verfährt man bei Anwendung von Butylalkohol.30 parts / I-naphthalenesulfonic acid are dissolved in 1400 parts of anhydrous methyl alcohol and passes into this mixture at boiling temperature Ethylene oxide. Then treatment is continued as indicated in Example 2. A similar procedure is used when applying of butyl alcohol.
*) Von dein Patentsucher ist als der Erfinder angegeben worden:*) Your patent seeker stated as the inventor:
Dr. Oskar Loehr in Leverkusen b. Köln.Dr. Oskar Loehr in Leverkusen b. Cologne.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC36943D DE580075C (en) | 1925-07-14 | 1925-07-14 | Process for the production of glycol monoalkyl ethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC36943D DE580075C (en) | 1925-07-14 | 1925-07-14 | Process for the production of glycol monoalkyl ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE580075C true DE580075C (en) | 1933-07-05 |
Family
ID=7022558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC36943D Expired DE580075C (en) | 1925-07-14 | 1925-07-14 | Process for the production of glycol monoalkyl ethers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE580075C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE944127C (en) * | 1941-10-29 | 1956-06-07 | Goldschmidt Ag Th | Process for the production of wetting, emulsifying and cleaning agents |
| DE1112637B (en) * | 1956-06-01 | 1961-08-10 | Union Carbide Corp | Process for the production of curable polyether resins |
| DE1112636B (en) * | 1957-05-17 | 1961-08-10 | Union Carbide Corp | Process for the production of curable polyether resins |
| DE1113575B (en) * | 1956-06-01 | 1961-09-07 | Union Carbide Corp | Process for the production of curable polyether resins containing epoxy groups |
-
1925
- 1925-07-14 DE DEC36943D patent/DE580075C/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE944127C (en) * | 1941-10-29 | 1956-06-07 | Goldschmidt Ag Th | Process for the production of wetting, emulsifying and cleaning agents |
| DE1112637B (en) * | 1956-06-01 | 1961-08-10 | Union Carbide Corp | Process for the production of curable polyether resins |
| DE1113575B (en) * | 1956-06-01 | 1961-09-07 | Union Carbide Corp | Process for the production of curable polyether resins containing epoxy groups |
| DE1112636B (en) * | 1957-05-17 | 1961-08-10 | Union Carbide Corp | Process for the production of curable polyether resins |
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