DE1074569B - Process for the preparation of aliphatic, olefinically unsaturated halodihydroxy compounds - Google Patents
Process for the preparation of aliphatic, olefinically unsaturated halodihydroxy compoundsInfo
- Publication number
- DE1074569B DE1074569B DENDAT1074569D DE1074569DA DE1074569B DE 1074569 B DE1074569 B DE 1074569B DE NDAT1074569 D DENDAT1074569 D DE NDAT1074569D DE 1074569D A DE1074569D A DE 1074569DA DE 1074569 B DE1074569 B DE 1074569B
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- olefinically unsaturated
- parts
- hydrogen
- diol
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 13
- 125000001931 aliphatic group Chemical group 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims 2
- -1 diol compounds Chemical class 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 230000000737 periodic Effects 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 230000001264 neutralization Effects 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims 3
- KDKYADYSIPSCCQ-UHFFFAOYSA-N 1-Butyne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims 2
- DLDJFQGPPSQZKI-UHFFFAOYSA-N 1,4-Butynediol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 claims 1
- 241000244206 Nematoda Species 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000010517 secondary reaction Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- 238000004448 titration Methods 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L Copper(II) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L Mercury(II) chloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229960002523 mercuric chloride Drugs 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M Copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940093915 Gynecological Organic acids Drugs 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L Mercury(II) acetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N Propargyl alcohol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 229940100892 mercury compounds Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/02—Halogenated hydrocarbons
- A61K31/035—Halogenated hydrocarbons having aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
- D06M13/148—Polyalcohols, e.g. glycerol or glucose
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Es ist bekannt, daß man aliphatische Halogenalkohole mit endständiger C = C-Bindung erhält, wenn man a-Acetylenalkohole mit Hälogenwasserstoffen umsetzt. Beispielsweise läßt sich 2-ChloraHylalkohol durch Einwirken von Chlorwasserstoff auf Propargylalkohol in Gegenwart von Quecksilberverbindungen bei mäßiger Wärme in dieser Weise herstellen.It is known that aliphatic halogen alcohols with a terminal C = C bond are obtained if a-acetylene alcohols with hemogenous hydrogen. For example, 2-ChloraHylalkohol can be acted upon from hydrogen chloride to propargyl alcohol in the presence of mercury compounds at moderate Produce heat in this way.
Man hat auch bereits versucht, Halogenwasserstoff an Diolverbindungen der Acetylenreihe anzulagern, dabei konnte man aber nur Verbindungen erhalten, in denen die Hydroxylgruppen wenigstens teilweise durch Halogenatome ersetzt waren (J. Gen. Chem. UdSSR., 15 [1945], S. 438, und Journ. Chem. Soc. [1946], S. 1015) oder die Acetylenbindung vollständig abgesättigt war (deutsche Patentschrift 823 882).Attempts have also been made to add hydrogen halide to diol compounds of the acetylene series, thereby but it was only possible to obtain compounds in which the hydroxyl groups were at least partially replaced by halogen atoms were replaced (J. Gen. Chem. USSR., 15 [1945], p. 438, and Journ. Chem. Soc. [1946], p. 1015) or the Acetylene bond was completely saturated (German patent 823 882).
Es wurde nun gefunden, daß man aliphatische, olefinisch ungesättigte Halogendihydroxyverbindungen erhält, wenn man auf Diolverbindungen der Acetylenreihe, die die Hydroxylgruppen in 1,4-Stellung enthalten, die also unmittelbar an beiden Seiten der —C=C-Gruppierung durch Hydroxylgruppen substituierte Kohlenstoffatome besitzen, Halogenwasserstoffe in Gegenwart von nicht komplexen Salzen von Metallen der I. und bzw. oder II. Nebengruppe des Periodischen Systems bei Temperaturen bis 60° C einwirken läßt.It has now been found that aliphatic, olefinically unsaturated halodihydroxy compounds can be used obtained when using diol compounds of the acetylene series which contain the hydroxyl groups in the 1,4-position, those immediately on both sides of the —C = C group have carbon atoms substituted by hydroxyl groups, hydrogen halides in the presence of non-complex salts of metals of the I. and / or II. subgroup of the periodic system Allowing temperatures of up to 60 ° C to act.
Geeignete Diole der Acetylenreihe sind beispielsweise die Acetylenglykole Butin-(2)-diol-(l,4), Pentin-(2)-diol-(l,4), Hexin-(3)-diol-(2,5), 2-Methylpentin-(3)-diol-(2,5) und 2,5-Diäthylhexin-(3)-diol-(2,5).Suitable diols of the acetylene series are, for example the acetylene glycols butyne- (2) -diol- (1,4), pentyne- (2) -diol- (1,4), hexyne- (3) -diol- (2,5), 2-methylpentin- (3 ) -diol- (2.5) and 2,5-diethylhexyne- (3) -diol- (2,5).
Als katalytisch wirkende Metallsalze seien vor allem die Mercuri- und Mercurosalze von anorganischen und organischen Säuren, ferner die Salze dieser Säuren mit ein- oder zweiwertigem Kupfer und von Silber genannt. Geeignete Verbindungen sind z. B. Mercurichlorid, Mercuriacetat, Mercurochlorid, Cuprichlorid, Cuprochlorid, Cupriacetat. Die Katalysatoren kann man ohne weitere Zusätze oder Aktivatoren verwenden. Vorteilhaft werden nur geringe Mengen benutzt, z. B. 1 bis 10 Gewichtsprozent, bezogen auf die Gewichtsmenge des umzusetzenden Diols.As catalytically active metal salts are above all the mercury and mercury salts of inorganic and organic acids, also called the salts of these acids with mono- or divalent copper and of silver. Suitable compounds are e.g. B. mercuric chloride, mercuric acetate, mercuric chloride, cuprichloride, cuprous chloride, Cupric acetate. The catalysts can be used without further additives or activators. Become beneficial only used small amounts, e.g. B. 1 to 10 percent by weight, based on the amount by weight of the reacted Diols.
Die für die Umsetzung geeigneten Temperaturen liegen zwischen 0 und 6O0C. Vorteilhaft arbeitet man zwischen etwa 20 und 300C, da insbesondere in diesem Bereich die Umsetzung sehr selektiv erfolgt und bisweilen bei höheren Temperaturen bereits Nebenreaktionen, wie teilweise Veresterung der Hydroxylgruppen, stattfinden können.Those suitable for reaction temperatures are between 0 and 6O 0 C. is advantageously carried out between about 20 and 30 0 C, there takes place in particular in this range, the reaction highly selective and sometimes at higher temperatures already side reactions such as partial esterification of the hydroxyl groups, take place can.
Die Durchführung des Verfahrens erfolgt vorteilhaft in der Weise, daß man zu dem Acetylenglykol oder zweckmäßig in seine Lösung den Halogenwasserstoff, z. B. Chlorwasserstoff oder Bromwasserstoff, gasförmig oder vorteilhaft gelöst, z. B. als konzentrierte wäßrige Halogenwasserstoffsäure, in. der berechneten Menge oder im Überschuß einbringt und den Katalysator einträgt. Als Lösungsmittel können dabei z. B. Wasser, niedrig-Verfahren zur HerstellungThe process is advantageously carried out in such a way that one adds to the acetylene glycol or expediently in its solution the hydrogen halide, e.g. B. hydrogen chloride or hydrogen bromide, gaseous or advantageously solved, z. B. as concentrated aqueous hydrohalic acid, in. The calculated amount or in Introduces excess and enters the catalyst. As a solvent, for. B. Water, low method for the production
von aliphatischen,of aliphatic,
olefinisch ungesättigtenolefinically unsaturated
HalogendihydroxyverbindungenHalodihydroxy compounds
Anmelder:Applicant:
Badische Anilin- & Soda-FabrikAniline & Soda Factory in Baden
Aktiengesellschaft,Corporation,
Ludwigshafen/RheinLudwigshafen / Rhine
Dr. Heinrich Pasedach, Ludwigshafen/Rhein,Dr. Heinrich Pasedach, Ludwigshafen / Rhine,
und Dr. Dieter Ludsteck,
Ludwigshafen/Rhein-Gartenstadt,
sind als Erfinder genannt wordenand Dr. Dieter Ludsteck,
Ludwigshafen / Rhine Garden City,
have been named as inventors
molekulare Alkohole, wie Methanol und Äthanol, halogenierte Kohlenwasserstoffe, wie Tetrachlorkohlenstoff, Chloroform, Eisessig, Tetrahydrofuran und Essigester, dienen. Die Reaktion ist beendet, sobald je Acetylenbindung des Acetylenglykols 1 Mol Halogenwasserstoff aufgenommen ist und keine weitere Umsetzung mehr erfolgt. Aus dem Umsetzungsgemisch läßt sich der nicht umgesetzte Halogenwasserstoff z. B. durch Destillation oder Neutralisation abtrennen und die ungesättigte Halogendihydroxyverbindung durch Extrahieren, Destillieren oder Umkristallisieren rein gewinnen. Die Ausbeute an den olefinisch ungesättigten Halogendihydroxyverbindungen läßt sich gegebenenfalls durch Verseifung der aus den Halogendihydroxyverbindungen durch Teilveresterung entstandenen Nebenprodukte mit Bicarbonatlösung noch erhöhen.molecular alcohols such as methanol and ethanol, halogenated hydrocarbons such as carbon tetrachloride, Chloroform, glacial acetic acid, tetrahydrofuran and ethyl acetate, serve. The reaction is ended as soon as there is an acetylene bond of the acetylene glycol 1 mol of hydrogen halide has been absorbed and no further reaction he follows. From the reaction mixture, the unreacted hydrogen halide z. B. by distillation or remove neutralization and remove the unsaturated halodihydroxy compound by extracting, distilling or recrystallize pure win. The yield of the olefinically unsaturated halodihydroxy compounds can optionally be obtained by saponification of the halodihydroxy compounds by partial esterification Increase by-products with bicarbonate solution.
Daß man erfindungsgemäß olefinisch ungesättigte Halogendihydroxyverbindungen erhält, war unerwartet, da bekanntlich das Reaktionsvermögen einer Hydroxygruppe ähnlich dem eines Halogenatoms ist und aus Chem. Reviews, 56 [1956], S. 599, bekannt war, daß das Reaktionsvermögen eines Halogenatoms in Verbindungen mit der GruppierungThe fact that olefinically unsaturated halodihydroxy compounds are obtained according to the invention was unexpected, since it is known that the reactivity of a hydroxyl group is similar to that of a halogen atom and is off Chem. Reviews, 56 [1956], p. 599, it was known that the reactivity of a halogen atom in compounds with the grouping
11 ββ αα
CH2 = CH-CH2Cl
zunimmt, wenn ein Wasserstoffatom am γ - C-atomCH 2 = CH-CH 2 Cl
increases when there is a hydrogen atom on the γ - C atom
909 728/519909 728/519
Claims (1)
verbindungen in guter Ausbeute erhalten lassen, wenn " -- ■ "
man Diolverbindungen der Acetylenreihe, die die Hy- . Patentanspruch =
droxygruppe in 1,4-Stellung enthalten, mit Halogen- 20 Verfahren zur Herstellung von aliphatischen, Wasserstoffen bei Temperaturen bis 6O0C in Gegenwart olefinisch ungesättigten Halogendihydroxyverbinvon nicht komplexen Salzen von Metallen der I. und düngen, dadurch gekennzeichnet, daß man auf bzw. oder II. Nebengruppe des Periodischen Systems Diolverbindungen der Acetylenreihe, die die Hydroumsetzt. xylgruppen in 1,4-Stellung enthalten, zweckmäßig Die erhaltenen olefinisch ungesättigten Halogendi- 25 auf ihre Lösungen, Halogenwasserstoffe bei Tempehydroxyverbindungen eignen sich als Schädlingsbe- raturen bis 60°C in Gegenwart von nicht komplexen kämpfungsmittel, insbesondere zur Bekämpfung von · Salzen von Metallen der I. und bzw. oder II. Nebeninsekten und Nematoden. Sie können ferner zur Her- gruppe des Periodischen Systems einwirken läßt.therefore it can be expected that the implementation of halogen 5. In a solution of 344 parts of butyne (2) hydrogen with diols of the acetylene series, which contain the hydrodiol (1,4) in 688 parts of concentrated hydrochloric acid under xyl groups in the 1,4-position, via the plant Stir in 20 parts of mercury chloride. The conversion stage, ie the formation of a monohalodihydroxy mixture, heats up and, by cooling to 25 to olefine, goes out and is kept as process products, due to 30 ° C. The esterification secondary reactions are determined by titration, essentially mono-io consumption of hydrochloric acid. As soon as 1 mole of hydrochloric acid to 1 mole of hydroxydichloroolefins are obtained. This existing butynediol is added, there is no further implementation. Prejudice was reinforced to the extent that from Journ. more instead. It is separated by distillation under ver-Chem. Soc. [1946], p. 1015, it was known that unconverted hydrochloric acid was removed under reduced pressure and the product of action of butyn- (2) -diol- (1,4) and chlorine fractionated the neutral reaction mixture in vacuo to hydrogen 1,3 -Dichlorobutene- (2) -ol- (4) is obtained. 15 next. 420 parts of 2-chloro-buten- (2) -diol- (1.4) are obtained. Surprisingly, however, it has been shown that the b.p. 0) 1 = 97 to 100.degree. The monohalodihydroxy crystals, which are still olefinically unsaturated from chloroform, melt at 38 to 39 ° C.
Keep compounds in good yield if "- ■"
one diol compounds of the acetylene series, which the Hy-. Claim =
containing hydroxy group in 1,4-position, with halogen 20 process for the preparation of aliphatic, hydrogen at temperatures up to 6O 0 C in the presence of olefinically unsaturated halogen dihydroxy compounds of non-complex salts of metals of I. and fertilize, characterized in that one on or or II. Subgroup of the Periodic System Diol compounds of the acetylene series, which converts the hydro. contain xyl groups in 1,4-position, expedient. The olefinically unsaturated halogenated salts obtained in their solutions, hydrogen halides in tempehydroxy compounds are suitable as pest temperatures up to 60 ° C. in the presence of non-complex control agents, in particular for combating salts of metals I. and or or II. Side insects and nematodes. You can also influence the grouping of the periodic table.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1074569B true DE1074569B (en) | 1960-02-04 |
Family
ID=598597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1074569D Pending DE1074569B (en) | Process for the preparation of aliphatic, olefinically unsaturated halodihydroxy compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1074569B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE764595C (en) * | 1939-02-14 | 1953-11-02 | Ig Farbenindustrie Ag | Process for the preparation of 1-oxy-2-chloropropene-2 |
-
0
- DE DENDAT1074569D patent/DE1074569B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE764595C (en) * | 1939-02-14 | 1953-11-02 | Ig Farbenindustrie Ag | Process for the preparation of 1-oxy-2-chloropropene-2 |
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