GB874558A - Organo-borane polymers - Google Patents
Organo-borane polymersInfo
- Publication number
- GB874558A GB874558A GB17887/59A GB1788759A GB874558A GB 874558 A GB874558 A GB 874558A GB 17887/59 A GB17887/59 A GB 17887/59A GB 1788759 A GB1788759 A GB 1788759A GB 874558 A GB874558 A GB 874558A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diborane
- reacted
- ether
- borane
- piperylene
- 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
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 title abstract 6
- 229910000085 borane Inorganic materials 0.000 title abstract 4
- 229920000642 polymer Polymers 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 6
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 3
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 abstract 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 abstract 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 abstract 2
- HVSYSQGJZITGQV-CCAGOZQPSA-N (1Z,3Z)-cyclonona-1,3-diene Chemical compound C1CC\C=C/C=C\CC1 HVSYSQGJZITGQV-CCAGOZQPSA-N 0.000 abstract 1
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 abstract 1
- ZOLLIQAKMYWTBR-MOLCZBCNSA-N (1z,5z,9z)-cyclododeca-1,5,9-triene Chemical compound C\1C\C=C/CC\C=C/CC\C=C/1 ZOLLIQAKMYWTBR-MOLCZBCNSA-N 0.000 abstract 1
- OGQVROWWFUXRST-FNORWQNLSA-N (3e)-hepta-1,3-diene Chemical compound CCC\C=C\C=C OGQVROWWFUXRST-FNORWQNLSA-N 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- FUPLVEAEPUKHAN-UHFFFAOYSA-N dibutylborane Chemical compound CCCCBCCCC FUPLVEAEPUKHAN-UHFFFAOYSA-N 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- AIGRXSNSLVJMEA-FQEVSTJZSA-N ethoxy-(4-nitrophenoxy)-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound O([P@@](=S)(OCC)C=1C=CC=CC=1)C1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-FQEVSTJZSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 239000000446 fuel Substances 0.000 abstract 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000005672 tetraenes Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000005671 trienes Chemical class 0.000 abstract 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/08—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing boron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
Linear or branched polyorgano boranes made up of 2-200 units each having the structural formula: <FORM:0874558/IV (a)/1> wherein R is a hydrocarbon radical containing at least 3 carbon atoms and wherein those valencies of the boron atoms which are not linked to carbon are satisfied by hydrogen, may be prepared by reacting a diolefin with a borane. Suitable borane starting materials are diborane, tetraborane, pentaborane (B5H11 or B5 H9), decaborane, and boron ethyl dihydride. Suitable diolefins are propadiene, butadiene; isoprene; piperylene; pentadiene 1, 4; hexadiene; 2, 3-dimethylbutadiene; 1, 4; heptadiene; cyclopentadiene; methyl cyclopentadiene; cyclohexadiene; cycloheptadiene; cyclooctadiene; cyclononadiene; also suitable are acetylene; methyl or ethyl acetylene; divinylbenzene; diallylbenzene; trienes; tetraenes. Inert solvents may be present, e.g. ethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether, pentane, heptane, or benzene, toluene or xylene together with a trace of an ether type solvent. The reaction may be performed at ambient or raised temperature. Raised pressure may also be used and an inert atmosphere, e.g. N2 is preferably maintained. In Examples (1) diborane is passed together with N2 through piperylene dissolved in ether. After 8 hours excess diborane was destroyed with methanol and a semi-solid polymer separated by distillation; (2) is similar; (3) isoprene was reacted with diborane; (4) cyclopentadiene was reacted with diborane in ether; (5) propadiene in ether was reacted with diborane; (6) cyclohexadiene dissolved in heptane with a trace of ether was reacted with diborane; (7) divinylbenzene was reacted with diborane; (8) butadiene was reacted with diborane; (9) butadiene was reacted with dibutyl borane; (10) pentadiene 1, 4 was reacted with tetrabutyl diborane; (11) piperylene and cycloheptadiene were reacted with diborane; (12) cyclododecatriene-1, 5, 9 was reacted with diborane. The products are useful as additives to gasoline or as rocket fuels.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US874558XA | 1958-09-23 | 1958-09-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB874558A true GB874558A (en) | 1961-08-10 |
Family
ID=22205287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17887/59A Expired GB874558A (en) | 1958-09-23 | 1959-05-26 | Organo-borane polymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB874558A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4638092A (en) * | 1982-01-21 | 1987-01-20 | Henkel Kommanditgesellschaft Auf Aktien | New organic boron polymers and their use |
| US4639498A (en) * | 1982-01-21 | 1987-01-27 | Henkel Kommanditgesellschaft Auf Aktien | Aerobically hardenable plastic compositions |
| US5382698A (en) * | 1988-08-01 | 1995-01-17 | Exxon Chemical Patents Inc. | Borated ethylene alpha-olefin copolymer substituted Mannich base lubricant dispersant additives |
| CN102604113A (en) * | 2012-03-15 | 2012-07-25 | 中国人民解放军国防科学技术大学 | Preparation method for boron carbide precursor |
-
1959
- 1959-05-26 GB GB17887/59A patent/GB874558A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4638092A (en) * | 1982-01-21 | 1987-01-20 | Henkel Kommanditgesellschaft Auf Aktien | New organic boron polymers and their use |
| US4639498A (en) * | 1982-01-21 | 1987-01-27 | Henkel Kommanditgesellschaft Auf Aktien | Aerobically hardenable plastic compositions |
| US5382698A (en) * | 1988-08-01 | 1995-01-17 | Exxon Chemical Patents Inc. | Borated ethylene alpha-olefin copolymer substituted Mannich base lubricant dispersant additives |
| US5433874A (en) * | 1988-08-01 | 1995-07-18 | Exxon Chemical Patents Inc. | Ethylene α-olefin copolymer substituted mannich base lubricant dispersant additives |
| CN102604113A (en) * | 2012-03-15 | 2012-07-25 | 中国人民解放军国防科学技术大学 | Preparation method for boron carbide precursor |
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