NO782434L - PROCEDURES FOR REDUCING UNTALTED ETHYLENE RESULTS FROM THE PRODUCTION OF VINYL CHLORIDE FROM ETHYLENE - Google Patents
PROCEDURES FOR REDUCING UNTALTED ETHYLENE RESULTS FROM THE PRODUCTION OF VINYL CHLORIDE FROM ETHYLENEInfo
- Publication number
- NO782434L NO782434L NO782434A NO782434A NO782434L NO 782434 L NO782434 L NO 782434L NO 782434 A NO782434 A NO 782434A NO 782434 A NO782434 A NO 782434A NO 782434 L NO782434 L NO 782434L
- Authority
- NO
- Norway
- Prior art keywords
- ethylene
- molar ratio
- water
- chlorine
- catalyst
- Prior art date
Links
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 29
- 239000005977 Ethylene Substances 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000012071 phase Substances 0.000 claims 2
- 230000014759 maintenance of location Effects 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000007789 gas Substances 0.000 description 9
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 1
- -1 aluminum alkoxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007038 hydrochlorination reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
- C07C29/66—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens by addition of hypohalogenous acids, which may be formed in situ, to carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Forbedring i fremgangsmåten for å redusereImprovement in the procedure to reduce
ureagert ethylen som fremkommer ved frem-unreacted ethylene, which is produced by
stilling av vinylklorid fra ethylenposition of vinyl chloride from ethylene
Foreliggende oppfinnelse angår en forbedring av fremgangsmåten for reduksjon av ethylen i gassfase med klorgass i nærvær av en effektiv mengde katalysator og i nærvær av vann. The present invention relates to an improvement of the method for reducing ethylene in gas phase with chlorine gas in the presence of an effective amount of catalyst and in the presence of water.
Forbedringen omfatter i korthet gjennomføring av reaksjonen i nærvær av en effektiv mengde tilsatt HC1, hvorved mengden av biproduktets 2-klorethanol minskes. In short, the improvement includes carrying out the reaction in the presence of an effective amount of added HC1, whereby the amount of the by-product 2-chloroethanol is reduced.
En kommersiell fremgangsmåte til fremstilling av vinylklorid er oxyklorering av ethylen. En annen kommersiell fremgangsmåte er oxy-hydro-klorering av ethylen. Begge.disse prosesser produserer ethylendiklorid som så krakkes til vinylklorid. I begge disse prosesser er der også en liten mengde ureagert ethylen som burde fjernes fra avgasstrømmen. I flere år er katalytisk klorering i gassfase av avgasstrømmen blitt benyttet for å minske ethylenmengden. Mens denne fremgangsmåte faktisk fjerner betydelige mengder ethylen, så har den den ulempe at den produserer en vik- A commercial method for producing vinyl chloride is oxychlorination of ethylene. Another commercial process is oxy-hydrochlorination of ethylene. Both of these processes produce ethylene dichloride which is then cracked into vinyl chloride. In both of these processes, there is also a small amount of unreacted ethylene that should be removed from the exhaust gas stream. For several years, catalytic chlorination in the gas phase of the exhaust gas stream has been used to reduce the amount of ethylene. While this process actually removes significant amounts of ethylene, it has the disadvantage of producing a wick-
tig mengde 2-klorethanol. Nærvær av 2-klorethanol er uønsket, fordi det øker oxygenbehovsnivået i avløpsvannet. tig amount of 2-chloroethanol. The presence of 2-chloroethanol is undesirable, because it increases the oxygen demand level in the waste water.
Fremgangsmåter hvorved•avgass trømmen inneholder en, liten mengde HCl er kjent. Denne mengde er immidlertid.utilstrekkelig til å hemme dannelsen av 2-klorethanol. Processes in which the off-gas stream contains a small amount of HCl are known. This amount is, however, insufficient to inhibit the formation of 2-chloroethanol.
Det er funnet at 2-klorethanoldannelse kan' hemmes sterkt eller nesten helt elimineres ved tilsetning av saltsyre til det katalytiske rensesystem. It has been found that 2-chloroethanol formation can be strongly inhibited or almost completely eliminated by adding hydrochloric acid to the catalytic purification system.
En undersøkelse av teknikkens stand frembragte ingen omtaler som kunne ansees å være relevante av den person som utfør-te granskningen. An examination of the state of the art produced no mentions that could be considered relevant by the person who carried out the examination.
Den foreliggende oppfinnelse er generelt en forbedringThe present invention is generally an improvement
av fremgangsmåten til å'la ethylen i gassfase reagere med klor i nærvær av en effektiv mengde katalysator og i nærvær av vann, of the process of allowing ethylene in gas phase to react with chlorine in the presence of an effective amount of catalyst and in the presence of water,
hvor forbedringen omfatter gjennomføring av reaksjonen i nærvær av en effektiv mengde tilsatt HCl for derved å minske mengden av biproduktet 2-klorethanol. where the improvement comprises carrying out the reaction in the presence of an effective amount of added HCl to thereby reduce the amount of the by-product 2-chloroethanol.
I en foretrukken utførelsesform er oppfinnelsen rettet på en forbedring i fremgangsmåten til å redusere mengden ureagert ethylen, som følger av oxykloreringen eller oxyhydrokloreringen av ethylen for fremstilling av ethylendiklorid og hvorved det ureagerte ethylen reageres i gassfase med klorgass i nærvær av vann og i nærvær av en effektiv mengde katalysator, idet den nevnte forbedring omfatter å gjennomføre den katalytiske reaksjon av ethylen og klor i nærvær av en effektiv mengde tilsatt HCl. In a preferred embodiment, the invention is directed to an improvement in the method for reducing the amount of unreacted ethylene, which results from the oxychlorination or oxyhydrochlorination of ethylene for the production of ethylene dichloride and whereby the unreacted ethylene is reacted in gas phase with chlorine gas in the presence of water and in the presence of a effective amount of catalyst, said improvement comprising carrying out the catalytic reaction of ethylene and chlorine in the presence of an effective amount of added HCl.
Egnede katalysatorer for bruk i oppfinnelsen omfatter fuktbare, uorganiske katalysatorer såsom metalloxyder og kiseloxyd. Eksempler på egnede katalysatorer omfatter kiseldioxyd, kiseldioxyd-aluminiumoxyd, magnesiumoxyd og aluminiumoxyd. Den foretrukne katalysator er aluminiumoxyd. Suitable catalysts for use in the invention include wettable, inorganic catalysts such as metal oxides and silicon oxide. Examples of suitable catalysts include silicon dioxide, silicon dioxide-aluminium oxide, magnesium oxide and aluminum oxide. The preferred catalyst is aluminum oxide.
Et spesielt foretrukket aktivert aluminiumoxyd til brukA particularly preferred activated alumina for use
i fremgangsmåten er et som fremstilles ved hydrolyse av aluminium-'alkoxyder. Det spesielt foretrukne aluminiumoxyd har følgende egenskaper: in the method is one that is produced by hydrolysis of aluminum alkoxides. The particularly preferred aluminum oxide has the following properties:
x praktisk talt hele resten er vann x practically all the rest is water
Et aktivert aluminiumoxyd som tilsvarer de egenskaper som er nevnt i det foregående er å få fra Conoco Chemicals Division of Continental Oil Company under varemerket "CATAPAL" SB. An activated aluminum oxide corresponding to the properties mentioned above is available from Conoco Chemicals Division of Continental Oil Company under the trademark "CATAPAL" SB.
Katalysatormengden kan uttrykkes på to måter. Først, volumforholdet katalysator til de kombinerte pågangsmengder lig-ger i området 0,001 til 100. For det annet skal volumet av katalysator være tilstrekkelig til å gi en oppholdstid på ca. 1 se-kund til ca. 5 timer. The amount of catalyst can be expressed in two ways. First, the volume ratio of catalyst to the combined input amounts is in the range 0.001 to 100. Secondly, the volume of catalyst must be sufficient to give a residence time of approx. 1 see-customer to approx. 5 hours.
Reaksjonen utføres med de reagerende stoffer i gassfase. Den utføres ved en temperatur i området fra ca. 50 til ca. 250°C, fortrinnsvis ca. 120 til 200°C, og ved et trykk i området fra ca. The reaction is carried out with the reacting substances in gas phase. It is carried out at a temperature in the range from approx. 50 to approx. 250°C, preferably approx. 120 to 200°C, and at a pressure in the range from approx.
0,1 til ca. 20 atmosfærer, fortrinnsvis ca. 1 til ca. 5 atmosfærer, med tilleggsbetingelsen at temperatur og trykk er slik at de reagerende stoffer befinner seg i gassfase. 0.1 to approx. 20 atmospheres, preferably approx. 1 to approx. 5 atmospheres, with the additional condition that the temperature and pressure are such that the reacting substances are in the gas phase.
Ethylenmengden som brukes i forhold til klor er på mol-basis i området ca. 10:1 til ca. 1:10, fortrinnsvis ca. 1,5:1 til ca. 1:15. The amount of ethylene used in relation to chlorine is on a mole basis in the range of approx. 10:1 to approx. 1:10, preferably approx. 1.5:1 to approx. 1:15.
Vannmengden er i området fra ca. 0,001 til ca. 10 mol pr. mol klor. Vanligvis er vannmengden på samme basis i området fra ca. 0,1 til ca. 1. The amount of water is in the area from approx. 0.001 to approx. 10 moles per moles of chlorine. Usually, the amount of water on the same basis is in the area from approx. 0.1 to approx. 1.
Mengden tilsatt HCl er i området fra ca.. 0,001 til ca. 10 mol pr. mol vann. Fortrinnsvis er mengden HCl i området fra ca. 0,1 til-ca. 1 mol pr. mol vann. The amount of added HCl is in the range from approx. 0.001 to approx. 10 moles per moles of water. Preferably, the amount of HCl is in the range from approx. 0.1 to-approx. 1 mole per moles of water.
For å illustrere den foreliggende oppfinnelses'art enda klarere gis følgende eksempler. Det må imidlertid forståes at oppfinnelsen ikke er begrenset til de spesifikke forhold eller de-taljer som fremse tes i disse eksempler, unntatt så langt som sli-ke begrensninger er spesifisert i de vedlagte krav. To illustrate the nature of the present invention even more clearly, the following examples are given. However, it must be understood that the invention is not limited to the specific conditions or details presented in these examples, except insofar as such limitations are specified in the attached claims.
Eksempel 1Example 1
Dette eksempel er sammenlignende og viser gjennomføring av reaksjonen i fravær av HCl. This example is comparative and shows completion of the reaction in the absence of HCl.
Reaktoren var et U-rør av glass (ca. 1 cm innvendig dia-meter) som ble delvis fyllt med 1/32" aluminiumoxydkuler ("CATAPAL" SB aluminiumoxyd). Mengden aluminiumoxyd var 26,6 g (ca. 26 ml fritt volum) . Reaktoren ble senket i et oppvarmet, ol-jebad med omrøring. Tilgangen bestod av (A) en målt "slip"-strøm avledet fra en kombinert strøm av luft (10 l/min) og ethylen (200 ml/min) og (B) klorgass i målte mengder. "Slip"-strømmen av luft og ethylen (A) ble sendt gjennom et kar fyllt med vann ved 25°C, hvor den ble mettet med vann. Strømmen av luft og ethylen og strømmen av klorgass ble forenet før de gikk inn i reaktoren. Reaksjonen fikk løpe flere minutter. En prøve av produktet ble tatt ut av avløpet og analysert. The reactor was a glass U-tube (approx. 1 cm internal diameter) which was partially filled with 1/32" aluminum oxide balls ("CATAPAL" SB aluminum oxide). The amount of aluminum oxide was 26.6 g (approx. 26 ml free volume ) . The reactor was immersed in a heated, stirred oil bath. The feed consisted of (A) a metered "slip" flow derived from a combined flow of air (10 L/min) and ethylene (200 mL/min) and (B) metered amounts of chlorine gas. The "slip" stream of air and ethylene (A) was passed through a vessel filled with water at 25°C, where it was saturated with water. The stream of air and ethylene and the stream of chlorine gas were united before entering the reactor. The reaction was allowed to run for several minutes. A sample of the product was taken from the effluent and analyzed.
Man kjørte forsøk under flere forskjellige betingelser. For hver ny gruppe betingelser fikk pågangsstrømmen til reaktoren løpe på maksimum(>100 ml/min) i begynnelsen for at systemet skul-le komme i likevekt hurtig. Experiments were run under several different conditions. For each new group of conditions, the input flow to the reactor was allowed to run at maximum (>100 ml/min) at the beginning so that the system would reach equilibrium quickly.
Følgende tabell viser forsøksbetingelsene og analysene The following table shows the experimental conditions and analyses
■av produktet.■of the product.
Eksempel 2 r Dette eksempel illustrerer oppfinnelsen. Forsøksbetingelsene var de samme som i eksempel 1 med unntagelse av at "slip"-strømmen av luft og .ethylen ble sendt gjennom konsentrert HCl (37 vekt%) i stedet for gjennom vann. Example 2 r This example illustrates the invention. The test conditions were the same as in Example 1 with the exception that the "slip" stream of air and ethylene was passed through concentrated HCl (37% by weight) instead of through water.
Eksempel 3 Example 3
En forsøksserie ble utført i en stor reaktor med og uten nærvær av tilsatt HCl. Driftsbetingelsene var innenfor de foretrukne områder som er beskrevet tidligere. Tatt over ett tydet forsøkene på en lavere mengde 2-klorethanol i produktet. Mengden 2-klorethanol var ca. 75 % av den man fikk når HCl ikke ble brukt. A series of experiments was carried out in a large reactor with and without the presence of added HCl. The operating conditions were within the preferred ranges described earlier. Taken as a whole, the experiments indicated a lower amount of 2-chloroethanol in the product. The amount of 2-chloroethanol was approx. 75% of that obtained when HCl was not used.
Når oppfinnelsen således er beskrevet i detalj, vil. fag-mannen kunne forstå at visse variasjoner og modifikasjoner kan When the invention is thus described in detail, those skilled in the art could understand that certain variations and modifications may
gjøres uten å avvike fra oppfinnelsens område slik denne er beskrevet her og i kravene. is done without deviating from the scope of the invention as described here and in the claims.
Claims (8)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83311677A | 1977-09-14 | 1977-09-14 | |
| US88979178A | 1978-03-23 | 1978-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO782434L true NO782434L (en) | 1979-03-15 |
Family
ID=27125583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782434A NO782434L (en) | 1977-09-14 | 1978-07-13 | PROCEDURES FOR REDUCING UNTALTED ETHYLENE RESULTS FROM THE PRODUCTION OF VINYL CHLORIDE FROM ETHYLENE |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5448702A (en) |
| DE (1) | DE2831539A1 (en) |
| FR (1) | FR2403322A1 (en) |
| GB (1) | GB2004272A (en) |
| NO (1) | NO782434L (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0113513B1 (en) * | 1982-12-24 | 1986-03-12 | Imperial Chemical Industries Plc | Production of 1,2-dichloroethane |
| DE3608043A1 (en) * | 1986-03-11 | 1987-09-17 | Wacker Chemie Gmbh | IMPROVED METHOD FOR PRODUCING 1,2-DICHLORETHANE BY GAS PHASE CHLORINATION OF ETHYLENE-CONTAINING GASES |
-
1978
- 1978-07-13 NO NO782434A patent/NO782434L/en unknown
- 1978-07-18 DE DE19782831539 patent/DE2831539A1/en not_active Withdrawn
- 1978-07-18 FR FR7821242A patent/FR2403322A1/en not_active Withdrawn
- 1978-07-19 GB GB7830284A patent/GB2004272A/en not_active Withdrawn
- 1978-09-13 JP JP11183178A patent/JPS5448702A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2403322A1 (en) | 1979-04-13 |
| DE2831539A1 (en) | 1979-03-22 |
| GB2004272A (en) | 1979-03-28 |
| JPS5448702A (en) | 1979-04-17 |
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