DE1037127B - Katalysatoren zur Polymerisation von Formaldehyd - Google Patents
Katalysatoren zur Polymerisation von FormaldehydInfo
- Publication number
- DE1037127B DE1037127B DEP10381A DEP0010381A DE1037127B DE 1037127 B DE1037127 B DE 1037127B DE P10381 A DEP10381 A DE P10381A DE P0010381 A DEP0010381 A DE P0010381A DE 1037127 B DE1037127 B DE 1037127B
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- polymerization
- monomeric
- catalysts
- under
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 145
- 238000006116 polymerization reaction Methods 0.000 title claims description 21
- 239000003054 catalyst Substances 0.000 title description 24
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052787 antimony Chemical group 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 230000007717 exclusion Effects 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229920006324 polyoxymethylene Polymers 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000000197 pyrolysis Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011089 carbon dioxide Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- -1 trinaphthylarsine Chemical compound 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- IIALFJBTHVVRJA-UHFFFAOYSA-N [Pb].CN(C)C Chemical compound [Pb].CN(C)C IIALFJBTHVVRJA-UHFFFAOYSA-N 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- KZTHCQYZOHMORT-UHFFFAOYSA-N dimethyl(phenyl)arsane Chemical compound C[As](C)C1=CC=CC=C1 KZTHCQYZOHMORT-UHFFFAOYSA-N 0.000 description 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- KQTKYCXEDDECIZ-UHFFFAOYSA-N ethylarsenic Chemical compound CC[As] KQTKYCXEDDECIZ-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IYGZNNLMGLWDQZ-UHFFFAOYSA-N methyl(dioctyl)stibane Chemical compound C[Sb](CCCCCCCC)CCCCCCCC IYGZNNLMGLWDQZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- KKOFCVMVBJXDFP-UHFFFAOYSA-N triethylstibane Chemical compound CC[Sb](CC)CC KKOFCVMVBJXDFP-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- GIIXTFIYICRGMZ-UHFFFAOYSA-N tris(2,3-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C(=C(C)C=CC=2)C)C=2C(=C(C)C=CC=2)C)=C1C GIIXTFIYICRGMZ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/08—Polymerisation of formaldehyde
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US742135XA | 1952-08-30 | 1952-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1037127B true DE1037127B (de) | 1958-08-21 |
Family
ID=22118355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP10381A Pending DE1037127B (de) | 1952-08-30 | 1953-08-29 | Katalysatoren zur Polymerisation von Formaldehyd |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE558695A (enrdf_load_stackoverflow) |
| DE (1) | DE1037127B (enrdf_load_stackoverflow) |
| FR (1) | FR1090028A (enrdf_load_stackoverflow) |
| GB (1) | GB742135A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1110863B (de) * | 1958-12-13 | 1961-07-13 | Glanzstoff Ag | Verfahren zur Polymerisation von Formaldehyd mittels metallorganischer Katalysatoren |
| DE1156235B (de) * | 1959-12-17 | 1963-10-24 | Hoechst Ag | Verfahren zur Polymerisation von Acetaldehyd |
| DE1162081B (de) * | 1961-02-01 | 1964-01-30 | Stamicarbon | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen |
| DE1192823B (de) * | 1961-05-12 | 1965-05-13 | Dynamit Nobel Ag | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen |
-
0
- BE BE558695D patent/BE558695A/xx unknown
-
1953
- 1953-08-28 FR FR1090028D patent/FR1090028A/fr not_active Expired
- 1953-08-28 GB GB23890/53A patent/GB742135A/en not_active Expired
- 1953-08-29 DE DEP10381A patent/DE1037127B/de active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1110863B (de) * | 1958-12-13 | 1961-07-13 | Glanzstoff Ag | Verfahren zur Polymerisation von Formaldehyd mittels metallorganischer Katalysatoren |
| DE1156235B (de) * | 1959-12-17 | 1963-10-24 | Hoechst Ag | Verfahren zur Polymerisation von Acetaldehyd |
| DE1162081B (de) * | 1961-02-01 | 1964-01-30 | Stamicarbon | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen |
| DE1192823B (de) * | 1961-05-12 | 1965-05-13 | Dynamit Nobel Ag | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1090028A (fr) | 1955-03-25 |
| BE558695A (enrdf_load_stackoverflow) | |
| GB742135A (en) | 1955-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1293453B (de) | Verfahren zur Herstellung von linearen, hochmolekularen, elastomeren, im wesentlichen homopolymerfreien und amorphen Copolymeren des Propylens oder Butens- 1 mit AEthylen | |
| DE2046722A1 (de) | Verfahren zur Herstellung cyclischer oelfimsch ungesättigter Kohlenwasser stoff polymere | |
| DE1256896B (de) | Verfahren zur Herstellung von Copolymerisaten des Formaldehyds | |
| DE1143333B (de) | Verfahren zur Herstellung von Polybutadien | |
| DE1037127B (de) | Katalysatoren zur Polymerisation von Formaldehyd | |
| DE2009580C3 (de) | Verfahren zur Polymerisation von Tetrahydrofuran | |
| DE1180939B (de) | Verfahren zur Herstellung von Copolymerisaten des Trioxans | |
| DE948088C (de) | Verfahren zur Herstellung von Corpolymerisaten | |
| DE1174987B (de) | Verfahren zur Herstellung von Homopoly-merisaten des Acetaldehyds oder Propionaldehyds oder von Copolymerisaten dieser beiden Aldehyde | |
| DE1147385B (de) | Verfahren zur Herstellung von Polymerisaten oder Copolymerisaten von Aldehyden | |
| DE1520242A1 (de) | Verfahren zur Herstellung von thermisch hochstabilem Polymethacrylnitril | |
| DE1595075C3 (de) | Verfahren zur Herstellung von Polymerisaten | |
| DE1091754B (de) | Verfahren zur Polymerisation von Vinylaethern | |
| DE875349C (de) | Verfahren zur Herstellung von Vinylidencyanid (1,1-Dicyanaethylen) | |
| AT222883B (de) | Verfahren zur Herstellung von linearen Polymeren | |
| AT255762B (de) | Verfahren zur Herstellung eines Copolymeren, das Oxymethylenglieder enthält | |
| DE1176862B (de) | Verfahren zur Herstellung von Copolymerisaten des Formaldehyds oder Trioxans | |
| AT227937B (de) | Verfahren zur Herstellung von neuen hochmolekularen linearen Polymeren | |
| AT213053B (de) | Verfahren zur Herstellung eines linearen, hochmolekularen Polymerisationsproduktes mit regelmäßiger Struktur | |
| AT229571B (de) | Verfahren zur Herstellung hochmolekularer, linearer, amorpher Copolymere von Äthylen mit höheren α - Olefinen | |
| AT257169B (de) | Verfahren zur Copolymerisation von Kohlenmonoxyd mit Formaldehyd oder seinen linearen oder cyclischen Polymeren | |
| DE1620906A1 (de) | Verfahren zur Polymerisation von Lactamen mit mindestens sieben Kohlenstoffatomen im Ring | |
| AT236646B (de) | Verfahren zur Herstellung von hochmolekularen Formaldehydpolymeren | |
| DE1595536A1 (de) | Verfahren zur kationischen Polymerisation | |
| DE1250124B (de) | Verfahren zur Herstellung von Copolymerisaten des Trioxans |