DE504730C - Process for polymerizing olefins - Google Patents
Process for polymerizing olefinsInfo
- Publication number
- DE504730C DE504730C DEH114439D DEH0114439D DE504730C DE 504730 C DE504730 C DE 504730C DE H114439 D DEH114439 D DE H114439D DE H0114439 D DEH0114439 D DE H0114439D DE 504730 C DE504730 C DE 504730C
- Authority
- DE
- Germany
- Prior art keywords
- boron fluoride
- polymerizing olefins
- ethylene
- hours
- oil
- 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 6
- 150000001336 alkenes Chemical class 0.000 title claims description 5
- 230000000379 polymerizing effect Effects 0.000 title claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- -1 boron fluoride halogen compounds Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 239000003921 oil Substances 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 3
- 229960003750 ethyl chloride Drugs 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 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
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/14—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C2/20—Acids of halogen; Salts thereof ; Complexes thereof with organic compounds
-
- 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
Description
Verfahren zum Polymerisieren von Olefinen Es ist bekannt, daß bei der Polymerisation von Olefinen mittels Borfluorids ein geringer Zusatz von Flußsäure die Polvmerisation sehr günstig beeinflußt.Process for polymerizing olefins It is known that in the polymerization of olefins by means of boron fluoride a small addition of hydrofluoric acid influences the polymerisation very favorably.
Es wurde nun gefunden, daß man die Flußsäure durch andere Halogenwasserstoffsäuren ersetzen kann. Ferner zeigte sich, daß man an Stelle dieser Säuren auch aliphatische oder alicyclische Halogenkohlenwasserstoffe setzen kann, die unter den Bedingungen des Prozesses ihr Halogen als Halogenwasserstoff abspalten.It has now been found that hydrofluoric acid can be replaced by other hydrohalic acids can replace. It was also found that aliphatic acids were also used in place of these acids or alicyclic halogenated hydrocarbons, which under the conditions the process split off their halogen as hydrogen halide.
Verwendet man z. B. als Beschleuniger neben Borfluorid Cyclohexylbromid, so wird die Polymerisation des Äthylens bei 16o bis 17o° in 12 Stunden beendet. Die Öle, die bei Verwendung der Halogenwasserstoffsäuren wie auch der Halogenkohlenwasserstoffe als Beschleuniger erhalten werden, sind hochviskos. Bei Verwendung von Äthylchlorid läßt sich ein großer Teil desselben durch Kondensation zurückgewinnen.If you use z. B. as an accelerator in addition to boron fluoride cyclohexyl bromide, so the polymerization of ethylene is completed at 16o to 17o ° in 12 hours. The oils that are produced when using the hydrohalic acids as well as the halogenated hydrocarbons obtained as accelerators are highly viscous. When using ethyl chloride a large part of it can be recovered by condensation.
Ein 01, welches bei gewöhnlicher Temperatur mit Borfluorid und Äthylchlorid als Beschleuniger gewonnen wurde. ist erheblich viskoser als ein bei erhöhter Temperatur hergestelltes. Im übrigen entsprechen. die Öle denen, die mittels Borfluorids oder dessen Doppelverbindungen in Verbindung mit fein verteilten Metallen oder auch durch Zusatz von Flußsäure erhalten werden können.An 01, which was obtained at normal temperature with boron fluoride and ethyl chloride as accelerators. is considerably more viscous than one made at elevated temperature. Otherwise correspond. the oils those that can be obtained by means of boron fluoride or its double compounds in connection with finely divided metals or by adding hydrofluoric acid.
Beispiel i io g Borfluorid, i2 g Äthylchlorid, ioo g Äthylen geben bei einem Anfangsdruck von 13o Atm. nach io Stunden 95 g 0l. Die Siedeanalyse ergibt folgende Zusaminensetzung: Kp,oo-22o° 6,9 %, KP., -1500 7,6 0/0, Kp. - 28o° 54,901" Rückstand und Verlust 3o,60/,. Der Rückstand stellt ein hochviskoses Öl dar. Die Fraktion vom Kps 15o bis 28o° zeigt folgende Viskosität: 2o'- 1,4ä abs. Zähigkeit, 5on =o,22 abs. Zähigkeit, 95' - 0,05 abs. Zähigkeit.Example: 10 g boron fluoride, 12 g ethyl chloride, 100 g ethylene at an initial pressure of 130 atm. after 10 hours 95 g of oil. The boiling point analysis gives the following composition: bp, oo-220 ° 6.9%, bp., -1500 7.6%, bp. -280 ° 54.901 "residue and loss 3o, 60 /,. The residue is a highly viscous one The fraction from Kps 15o to 28o ° shows the following viscosity: 20 '-1.4' absolute toughness, 5on = 0.22 absolute toughness, 95 ' - 0.05 absolute toughness.
ßeispiel2 io g Borfluorid, 12 g Jodwasserstoff, Zoo g Äthylen geben bei einem Anfangsdruck von Zoo Atm. nach io Stunden 75 g Öl.Example 2 give 10 g boron fluoride, 12 g hydrogen iodide, zoo g ethylene at an initial pressure of Zoo Atm. after 10 hours 75 g of oil.
Beispiel 3 io g Borfluorid, 5 g Äthylfluorid, ioo g Äthylen geben bei einem Anfangsdruck von i 3o Atm. nach i o Stunden i oo g Öl.Example 3 give 10 g boron fluoride, 5 g ethyl fluoride, 100 g ethylene at an initial pressure of 30 atm. after 10 hours 100 g of oil.
Beispiel 4.Example 4.
io g Borfluorid, 20 g Cyclohexylbrotnid, i oo g Äthylen geben bei einem Anfangsdruck von i2.1 Atin. beim Erhitzen auf i 6o bis 170° nach 12 Stunden 93 g Öl.Add 10 g of boron fluoride, 20 g of cyclohexyl brotnide, and 10 g of ethylene an initial pressure of i2.1 Atin. when heated to 150 to 170 ° after 12 hours 93 g of oil.
Beispiel io g Borfluorid, io g Chlorwasserstoff, ioo g Äthylen geben bei einem Anfangsdruck von ioo Atm. go g Öl.Example give 10 g boron fluoride, 10 g hydrogen chloride, 100 g ethylene at an initial pressure of 100 atm. go g of oil.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH114439D DE504730C (en) | 1927-12-21 | 1927-12-21 | Process for polymerizing olefins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH114439D DE504730C (en) | 1927-12-21 | 1927-12-21 | Process for polymerizing olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE504730C true DE504730C (en) | 1933-03-24 |
Family
ID=7172046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH114439D Expired DE504730C (en) | 1927-12-21 | 1927-12-21 | Process for polymerizing olefins |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE504730C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE867992C (en) * | 1936-03-12 | 1953-02-23 | Basf Ag | Process for converting ethylene homologues into oily or higher molecular weight products by polymerisation |
-
1927
- 1927-12-21 DE DEH114439D patent/DE504730C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE867992C (en) * | 1936-03-12 | 1953-02-23 | Basf Ag | Process for converting ethylene homologues into oily or higher molecular weight products by polymerisation |
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