GB858793A - Improvements in epoxidation - Google Patents
Improvements in epoxidationInfo
- Publication number
- GB858793A GB858793A GB7792/59A GB779259A GB858793A GB 858793 A GB858793 A GB 858793A GB 7792/59 A GB7792/59 A GB 7792/59A GB 779259 A GB779259 A GB 779259A GB 858793 A GB858793 A GB 858793A
- Authority
- GB
- United Kingdom
- Prior art keywords
- peracetic acid
- ethylenic
- carbon
- residence time
- zone
- 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
- 238000006735 epoxidation reaction Methods 0.000 title 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 16
- 150000001875 compounds Chemical class 0.000 abstract 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 5
- 229910052799 carbon Inorganic materials 0.000 abstract 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000007791 liquid phase Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- IMYZYCNQZDBZBQ-UHFFFAOYSA-N (+-)-8-(cis-3-octyl-oxiranyl)-octanoic acid Natural products CCCCCCCCC1OC1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-UHFFFAOYSA-N 0.000 abstract 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- YDIZFUMZDHUHSH-UHFFFAOYSA-N 1,7-bis(ethenyl)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene Chemical compound C12OC2C=CC2(C=C)C1(C=C)O2 YDIZFUMZDHUHSH-UHFFFAOYSA-N 0.000 abstract 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 abstract 1
- MBOPNDFEIXMJOS-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carbonitrile Chemical compound C1C(C#N)CCC2OC21 MBOPNDFEIXMJOS-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- VYXHEFOZRVPJRK-UHFFFAOYSA-N ethyl 3-methyloxirane-2-carboxylate Chemical compound CCOC(=O)C1OC1C VYXHEFOZRVPJRK-UHFFFAOYSA-N 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 150000003017 phosphorus Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Epoxy Compounds (AREA)
Abstract
A polymer or copolymer of butadiene, is epoxidised by introducing said compound and peracetic acid continuously into an elongated reaction zone, the length of which equals 100 to 10,000 4K/p where K is the area of the smallest perpendicular cross-section of said zone, and wherein the expression 4K/p is in the range of from 0,63 to 13,0 cm. under pressure sufficient to maintain a liquid phase reaction mixture; and for a residence time at least sufficient to epoxidise at least one carbon to carbon ethylenic bond of the ethylenically unsaturated compound, said residence time not exceeding 45 minutes. A plurality of elongated reaction zones may be used in series or parallel. Temperatures of 0-150 DEG C., preferably 20-130 DEG C. are specified, with pressures up to 100 atmospheres. The peracetic acid is preferably introduced in an inert organic solvent, specifically containing 5-50 weight per cent of peracetic acid. Generally the molar ratio of peracetic acid to ethylenic double bond should be 0,05 to 5,0, preferably 0,2 to 2,0 Specification 784,620 is referred to.ALSO:An ethylenically unsaturated compound containing at least 3 carbon atoms, the atoms directly joined to the ethylenic carbon atoms being hydrogen or carbon, is epoxidised by introducing said compound and peracetic acid continuously into an elongated reaction zone, the length of which equals 100 to 10,000 <FORM:0858793/IV(b)/1> where K is the area of the smallest perpendicular cross section of said zone, and wherein the expression <FORM:0858793/IV(b)/2> is in the range of from 0,63 to 13,0 cm. under pressure sufficient to maintain a liquid phase reaction mixture ; and for a residence time at least sufficient to epoxidise at least one carbon to carbon ethylenic bond of the ethylenically unsaturated compound, said residence time not exceeding 45 minutes. A plurality of elongated reaction zones may be used in series or parallel. Temperatures of 0-150 DEG C., preferably 20-130 DEG C. are specified, with pressures up to 100 atmospheres. The peracetic acid is preferably introduced in an inert organic solvent, specifically containing 5-50 weight per cent. of peracetic acid. Generally the molar ratio of peracetic acid to ethylenic double bond should be 0,05 to 5,0, preferably 0,2 to 2,0. A polymerisation inhibitor may be present. Specified ethylenic compounds include hydrocarbons, alcohols, phenols, ethers, amides, imides, nitriles, ketones, carboxylic acids and esters, acetals, halocarbons and esters of phosphorus acids. Compounds prepared in Examples from the corresponding ethylenic compounds are (1) and (2) propylene oxide ; (3) isobutylene oxide ; (4) butadiene monoxide ; (5) butadiene dioxide (from the monoxide) ; (6) divinylbenzene dioxide ; (7) ethyl 2, 3-epoxybutyrate ; (8) 6-methyl-3, 4-epoxycyclohexylmethyl 6-methyl-3,4-epoxy-cyclohexanecarboxylate ; (9) epoxystearic acid (from oleic acid) ; (10) 3, 4-epoxycyclohexane-carbonitrile ; and (11) bis (2, 3-epoxycyclopentyl) ether. Specification 784,620 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US858793XA | 1958-03-07 | 1958-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB858793A true GB858793A (en) | 1961-01-18 |
Family
ID=22194563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7792/59A Expired GB858793A (en) | 1958-03-07 | 1959-03-06 | Improvements in epoxidation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB858793A (en) |
-
1959
- 1959-03-06 GB GB7792/59A patent/GB858793A/en not_active Expired
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