DE718057C - Process for the production of higher molecular weight chlorinated hydrocarbons - Google Patents
Process for the production of higher molecular weight chlorinated hydrocarbonsInfo
- Publication number
- DE718057C DE718057C DEC51442D DEC0051442D DE718057C DE 718057 C DE718057 C DE 718057C DE C51442 D DEC51442 D DE C51442D DE C0051442 D DEC0051442 D DE C0051442D DE 718057 C DE718057 C DE 718057C
- Authority
- DE
- Germany
- Prior art keywords
- production
- higher molecular
- chlorinated hydrocarbons
- molecular weight
- trichlorethylene
- 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 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 title claims description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 5
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C08F114/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F114/02—Monomers containing chlorine
- C08F114/04—Monomers containing two carbon atoms
- C08F114/12—1,2- Dichloroethene
-
- 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
- C08F114/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F114/02—Monomers containing chlorine
- C08F114/04—Monomers containing two carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Verfahren zur Herstellung von höhermolekularen Chlorkohlenwasserstoffen Es wurde gefunden, daß Trichloräthylen und symmetrisches Dichlnriäthylen beim Erhitzen mit organischen Superoxyden unter Druck glatt in polymere Verbindungen Übergehen.Process for the production of higher molecular weight chlorinated hydrocarbons It has been found that trichlorethylene and symmetrical dichloroethylene when heated With organic superoxides, smoothly converts into polymeric compounds under pressure.
Bisher waren nur zwei Wege bekannt, um neben völlig unverwertbaren teerigen, harzigen und kohligen Produkten überhaupt höhermolekulare Chlorkohlenwasserstoffe aus Trichloräthylen oder symmetrischem Dichloräthylen zu gewinnen: die Behandlung mit Aliiminiumchlorid bei verhältnismäßig niedrigen Temperaturen oder eins Art Crackprozeß bei 6oo bis 7oo°. Nach der .erstgenannten Arbeitsweise wird jedoch durch zu weit gehrende Kondensation des Trichloräthylens mit Al C13 der größte Teil des Trichloräthylens in eine schwarze, kohlige Masse Übergeführt. Was an flüssigen Produktren anfällt, ist nicht @einh@itlich, sondern ein Gemisch von verschiedenen Körpern. Die Reaktion kann nicht :als Polymerisation, sondern nur als Kondensation bezeichnet werden. Beim Durchleiten von Trichloräthylendämpfen durch ,ein auf 6oo bis 7oo° geheiztes Rohr entstieht das Dunere des Trichloräthylensnur meiner Ausbeute von 15 0'o neben einer großen Zahl und Menge unverwertbarer Nebenprodukte. Darüber hinaus -wird durch das Auftreten von Chlor und Chlonvasserstof6 bei 6oo bis 700° die Materialfrage für die Reaktionstemperatur so schwierig, daß auch aus diesem Grunde eine technische Durchführung des Verfahrens nicht oder nur mit sehr großen Schwierigkeiten möglich ist.So far, only two ways were known, besides being completely unusable tarry, resinous and carbonaceous products generally have higher molecular weight chlorinated hydrocarbons Obtaining from trichlorethylene or symmetrical dichloroethylene: the treatment with aluminum chloride at relatively low temperatures or some kind of cracking process at 6oo to 7oo °. After the first-mentioned working method, however, it becomes too far Including condensation of trichlorethylene with Al C13, most of the trichlorethylene Converted into a black, carbonaceous mass. What is the result of liquid products is not @ uniform, but a mixture of different bodies. The reaction cannot: be referred to as polymerization, but only as condensation. When passing trichlorethylene vapors through, a heated to 600 to 7oo ° In the tube, the trichlorethylene is produced only in addition to my yield of 150,000 a large number and quantity of unusable by-products. In addition, -will through the occurrence of chlorine and hydrogen chloride at 600 to 700 ° is the material question so difficult for the reaction temperature that for this reason, too, a technical one Implementation of the process is not possible or only possible with great difficulty is.
Demgegenüber ermöglicht das oben angegebene Verfahren eine wirtschaftlich und technisch voll befriedigende Herstellung der vor allem als Zwischenprodukte für weitere Umsetzungen wertvollen Polymeren des Trichlonäthylens und symmetrischen Dichloräthylens untrer Ausschaltung der Bildung von Abfallprodukten. Beispiel i i oo Teile symmetrisches Dichloräthylen wurden mit i Teil Benzoylsuperoxyd unter Druck 3 Stunden auf 9o' erhitzt. Danach wurden von dem Reaktionsprodukt 7o Teile unverändertes Dichloräthylen abdestilliert. Es verblieb eine Flüssigkeit, die unter i 2 mm Hg Druck bei etwa 78° überdestillierte und die Zusammensetzung des Dichloräthylens hatte. . Beispiel 2 ioo Teilte Trichloräthylen wurden mit i Teil Benzoylsuperoxyd unter Druck 3 Stunden auf 140' erhitzt. Von dem Reaktionsprodukt wurden sodann, 75 Teile unverändertes Trichloräthylen. bei.-.gewöhnlichem Druck abdestilliert. Das Polymerisat destillierte unter 12 mm Hg Druck bei etwa tos' fast vollständig über; es hatte die Zusammensetzung des Trichloräthyleris.In contrast, the method specified above enables an economical one and technically fully satisfactory production, especially as intermediate products for further reactions valuable polymers of trichlorethylene and symmetrical ones Dichloroethylene with elimination of the formation of waste products. Example i i oo parts of symmetrical dichloroethylene were mixed with i part of benzoyl peroxide Pressure heated to 90 'for 3 hours. Thereafter, the reaction product became 70 parts unchanged dichloroethylene distilled off. A liquid remained underneath i 2 mm Hg pressure distilled over at about 78 ° and the composition of dichloroethylene would have. . Example 2 100 parts of trichlorethylene were mixed with 1 part of benzoyl peroxide heated under pressure to 140 'for 3 hours. From the reaction product were then 75 parts unchanged trichlorethylene. distilled off at ordinary pressure. That Polymer distilled almost completely under 12 mm Hg pressure at about tos'; it had the composition of Trichloräthyleris.
Das ßenzoylsttperozyd ließ sich mit g1ei-. chem Erfolg durch Aeetylsuperoxyd Polymerisate können als Zwischenverbindungen für die Herstellung von anderen Kohlenstoffverbindungen oder als Lösungsmittel verwendet werden. .The ßenzoylstperozyd settled with g1ei-. chem success through acetyl peroxide Polymers can be used as intermediates for the production of other carbon compounds or used as a solvent. .
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC51442D DE718057C (en) | 1936-03-17 | 1936-03-17 | Process for the production of higher molecular weight chlorinated hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC51442D DE718057C (en) | 1936-03-17 | 1936-03-17 | Process for the production of higher molecular weight chlorinated hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE718057C true DE718057C (en) | 1942-02-28 |
Family
ID=7027396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC51442D Expired DE718057C (en) | 1936-03-17 | 1936-03-17 | Process for the production of higher molecular weight chlorinated hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE718057C (en) |
-
1936
- 1936-03-17 DE DEC51442D patent/DE718057C/en not_active Expired
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