CA1233485A - Process for the production of methallyl chloride - Google Patents
Process for the production of methallyl chlorideInfo
- Publication number
- CA1233485A CA1233485A CA000472715A CA472715A CA1233485A CA 1233485 A CA1233485 A CA 1233485A CA 000472715 A CA000472715 A CA 000472715A CA 472715 A CA472715 A CA 472715A CA 1233485 A CA1233485 A CA 1233485A
- Authority
- CA
- Canada
- Prior art keywords
- oxygen
- reaction
- vol
- chlorine
- process according
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ABSTRACT
For the production of methallyl chloride from isobutene and chlorine in the gaseous phase, 0.001 - 1 vol-%, preferably 0.01 - 0.5 vol-% of oxygen and/or 0.01 - 5 vol-%
of hydrogen chloride is added to the gaseous starting materials. The oxygen can also be dosed in the form of air.
./.
For the production of methallyl chloride from isobutene and chlorine in the gaseous phase, 0.001 - 1 vol-%, preferably 0.01 - 0.5 vol-% of oxygen and/or 0.01 - 5 vol-%
of hydrogen chloride is added to the gaseous starting materials. The oxygen can also be dosed in the form of air.
./.
Description
~33~
Methallyl chloride (3-chloro-2-methyl-1-propene) is manufactured industrially by reacting isobutene with chlorine in the gaseous phase. The reaction takes place ln a cooled tubular reactor at temperatures around (if at all possible below) 100 C
and under approximately atmospheric pressure. The required reaction time ranges from 0.5 second to a few seconds. In order to avoid continued chlorination of the methallyl chloride, an excess of isobutene is employed in all cases. The starting compounds are fed into the reactor by way of a bicomponent (two-fluid) nozzle. The introduction of liquid isobutene through a nozzle, as the indirect coolant, has not proven it-self; this step leads to the increased formation of undesired, higher-chlorinated products, obviously a consequence of poor intermixing of the reactants (Ullmanns Encyklopaedie der technischen Chemie" 4th edition, volume 9, pp. 472 et seq., Publishers Chemie, Weinheim, 1975).
according to experiments by A. Striegler ~"Erfahrungen bei der Chlorierung von Isobutylen" [Experience Gained in Chlorinating Isobutylen~], Chem. TechnO 9 : 523 et seq., 9th year, 1957), irregularities occur in the reaction of isobutene with chlorine on a laboratory scale, manifesting themselves in a sudden, inexplicable rise in temperature (from 70 C to 100-140C), and causing a marked increase in the undesirable, higher chlorinated products (chapter 2.3, on page 525). On account of the difficult mixing of the reactants in a "semi-industrial"
experimental installation, the industrial realization of the gas-phase chlorination procedure has even been found to be entirely questionable: "It was found to be impossible to explain and to eliminate the uncontrollable fluctuations in -the compost tion of -the chlorination product" (chapter 2.45, pp. 526/527).
Although the large-scale industrial isobutene chlorina-tion could be realized in the meantime, in spite of the warning contained in the literature reference, -the aforedescribed irregu-larities can also be observed, according to own experience, with this reaction system on an industrial scale, namely with fluctua-ting frequency and duration with respect to the irregularlties.
The reaction temperature often rises within a few minutes to around 300C, accompanied by massive soot formation. The uniform nozzle dosing of the starting materials can then no longer be insured; the installation must be shut down and cleaned.
Due to uncontrollable irregularities in the prior-art pro-cesses, the object arises of finding a method which, contrary to the previous teaching, can be performed even on a large indus-trial scale without disturbances at an extensively constant temperature.
The present invention provides a process for the produc-tion of methallyl chloride, comprising reacting isobutene and chlorine in the gaseous phase in the presence of from 0.001 to 1 vol. % of oxygen or from 0.01 to 5 vol. % of hydrogen chloride as a reaction stabilizer thoroughly mixed with the reactants.
The addition of oxygen (in the form of air) to the reac-tion has been experimentally tested by A. Striegler (see above);
however, this researcher merely found that oxygen does not interfere with the reaction tchapter 2.34,p.526 at the top). This finding 3~
can, moreover, be derived from a work by J. Burgin et al. from the year 1939 (Ind. Eng. Chem. _ : 1413-1419 [1939]). Thus/ the fact that oxygen, in the specifically selected quantities as mentioned above, eliminates the aforementioned irregularities is surprising and is new, and it could not be forseen.
The use of oxygen for stabilizing the gas-phase chlori-nation of isobutene affords the advantage that there are no longer inactive periods of the manufacturing installa-tion due to constant high yields of methallyl chloride at constant low reaction temper-atures. This is advantageous, in particular, where the reaction is conducted under a slightly increased pressure (up to about 3 bar abs.), for my own experlence has shown that, under a slightly raised pressure, the reaction, which is otherwise carried out un-der normal pressure, exhibits especially frequently increased reaction temperatures and thus reduces yields of methallyl chloride.
The amount of oxygen to be used depends on various considerations, for example the purity of the starting materials employed. Contents of between 0.001 and 1 vol. % of oxygen, based on the total volume of the gaseous starting materials, are suffi-cient for ensuring a stable course of reaction. In most cases, a satisfactory result can be obtained with an oxygen quantity of less than about 1 vol. %. Preferably, 0.01 - 0.5 vol. % of oxygen is utilized. Amounts of above 1 vol. % of oxygen have the drawback that their removal leads to -the loss of the product.
3~
The oxygen may be utilized as such or in the form of air.
An essential aspect for the conductance of the process is -thorough mixing of the oxygen with the reaction mixture, which is to take place suitably before beginning of the reaction. The more -thorough such mixing the less oxygen is required.
It ist of course, also feasible to operate the process of this invention using chlorine which already contains oxygen in an adequate amount from its manufacture or processing stage (for example so-called residual chlorine). In such a case, the separate introduction of oxygen is, of course, superfluous.
It has furtIlermore been found that, in a few special cases hydroyen chloride can also he utilized as the reaction stabilizerr especially where the reactant chlorine contains dichloromonoxide [dichloro oxide] (C120) as the impurity. The required amount of hydrogen chloride ranges from 0.01 to 5 vol. %, preferably below 1 vol. %, based on the total volume of the gaseous feedstoc]c. It is also possible to employ a mixture of oxygen and hydrogen chloride.
The following examples will explain the process of this invention.
~3~
Example 1 Isobutene and chlorine are reacted in a jacket cooled tubular reactor in a molar ratio of 1.04 : 1 to methallyl chloride as the primary reaction product. The reactants are introduced into the reac'or by way of a two-fluid nozzle. The pressure ranges on the average around 1.6 bar (absolute). The reaction temperature is measured after a reaction route of 4, 8, and 12 meters (measuring points T4, T8 and T12). The reaction is "stabilized" wi-th 0.07 vol-% of air, corresponding to 0.013 vol-% of oxygen.
In order to demonstrate the stabilizing effect of the added oxygen, the oxygen feed was interrupted for testing purposes. Thereupon the reaction temperature rose, after a reaction route of 4 meters, from 94 to 220 C within 4 min-lS utes. The rise proceeded almost linearly. The reintroductionof oxygen in the original quantity resulted, within about 10 minutes in restoration of the original temperature level.
similar interruption in oxygen feed in a case of trouble in the installation resulted in a "runaway"
reaction; the reaction temperature reached values of above 400 C, and strong soot formation began; the installation had to be shut down.
Thy tabls jet out below gives an overview ox the temperature profiLe with the aforementioned, expexi~ental interruption of oxygen fled.
~33~
. . . .
Time Oxygen Content ! Temp-oratu:res min. of Gasous Feed ¦ T4 To i T12 Mixture vol-~ C C C
__ ____ _ ___ ---__ __. ___ _ _ _ ___ . __ _ _ __ ___ _ I_ ___ ___ 5 -10 O oO13 94 88 64 O O 000 9~ 188 64 1 0~000 113 194 66
Methallyl chloride (3-chloro-2-methyl-1-propene) is manufactured industrially by reacting isobutene with chlorine in the gaseous phase. The reaction takes place ln a cooled tubular reactor at temperatures around (if at all possible below) 100 C
and under approximately atmospheric pressure. The required reaction time ranges from 0.5 second to a few seconds. In order to avoid continued chlorination of the methallyl chloride, an excess of isobutene is employed in all cases. The starting compounds are fed into the reactor by way of a bicomponent (two-fluid) nozzle. The introduction of liquid isobutene through a nozzle, as the indirect coolant, has not proven it-self; this step leads to the increased formation of undesired, higher-chlorinated products, obviously a consequence of poor intermixing of the reactants (Ullmanns Encyklopaedie der technischen Chemie" 4th edition, volume 9, pp. 472 et seq., Publishers Chemie, Weinheim, 1975).
according to experiments by A. Striegler ~"Erfahrungen bei der Chlorierung von Isobutylen" [Experience Gained in Chlorinating Isobutylen~], Chem. TechnO 9 : 523 et seq., 9th year, 1957), irregularities occur in the reaction of isobutene with chlorine on a laboratory scale, manifesting themselves in a sudden, inexplicable rise in temperature (from 70 C to 100-140C), and causing a marked increase in the undesirable, higher chlorinated products (chapter 2.3, on page 525). On account of the difficult mixing of the reactants in a "semi-industrial"
experimental installation, the industrial realization of the gas-phase chlorination procedure has even been found to be entirely questionable: "It was found to be impossible to explain and to eliminate the uncontrollable fluctuations in -the compost tion of -the chlorination product" (chapter 2.45, pp. 526/527).
Although the large-scale industrial isobutene chlorina-tion could be realized in the meantime, in spite of the warning contained in the literature reference, -the aforedescribed irregu-larities can also be observed, according to own experience, with this reaction system on an industrial scale, namely with fluctua-ting frequency and duration with respect to the irregularlties.
The reaction temperature often rises within a few minutes to around 300C, accompanied by massive soot formation. The uniform nozzle dosing of the starting materials can then no longer be insured; the installation must be shut down and cleaned.
Due to uncontrollable irregularities in the prior-art pro-cesses, the object arises of finding a method which, contrary to the previous teaching, can be performed even on a large indus-trial scale without disturbances at an extensively constant temperature.
The present invention provides a process for the produc-tion of methallyl chloride, comprising reacting isobutene and chlorine in the gaseous phase in the presence of from 0.001 to 1 vol. % of oxygen or from 0.01 to 5 vol. % of hydrogen chloride as a reaction stabilizer thoroughly mixed with the reactants.
The addition of oxygen (in the form of air) to the reac-tion has been experimentally tested by A. Striegler (see above);
however, this researcher merely found that oxygen does not interfere with the reaction tchapter 2.34,p.526 at the top). This finding 3~
can, moreover, be derived from a work by J. Burgin et al. from the year 1939 (Ind. Eng. Chem. _ : 1413-1419 [1939]). Thus/ the fact that oxygen, in the specifically selected quantities as mentioned above, eliminates the aforementioned irregularities is surprising and is new, and it could not be forseen.
The use of oxygen for stabilizing the gas-phase chlori-nation of isobutene affords the advantage that there are no longer inactive periods of the manufacturing installa-tion due to constant high yields of methallyl chloride at constant low reaction temper-atures. This is advantageous, in particular, where the reaction is conducted under a slightly increased pressure (up to about 3 bar abs.), for my own experlence has shown that, under a slightly raised pressure, the reaction, which is otherwise carried out un-der normal pressure, exhibits especially frequently increased reaction temperatures and thus reduces yields of methallyl chloride.
The amount of oxygen to be used depends on various considerations, for example the purity of the starting materials employed. Contents of between 0.001 and 1 vol. % of oxygen, based on the total volume of the gaseous starting materials, are suffi-cient for ensuring a stable course of reaction. In most cases, a satisfactory result can be obtained with an oxygen quantity of less than about 1 vol. %. Preferably, 0.01 - 0.5 vol. % of oxygen is utilized. Amounts of above 1 vol. % of oxygen have the drawback that their removal leads to -the loss of the product.
3~
The oxygen may be utilized as such or in the form of air.
An essential aspect for the conductance of the process is -thorough mixing of the oxygen with the reaction mixture, which is to take place suitably before beginning of the reaction. The more -thorough such mixing the less oxygen is required.
It ist of course, also feasible to operate the process of this invention using chlorine which already contains oxygen in an adequate amount from its manufacture or processing stage (for example so-called residual chlorine). In such a case, the separate introduction of oxygen is, of course, superfluous.
It has furtIlermore been found that, in a few special cases hydroyen chloride can also he utilized as the reaction stabilizerr especially where the reactant chlorine contains dichloromonoxide [dichloro oxide] (C120) as the impurity. The required amount of hydrogen chloride ranges from 0.01 to 5 vol. %, preferably below 1 vol. %, based on the total volume of the gaseous feedstoc]c. It is also possible to employ a mixture of oxygen and hydrogen chloride.
The following examples will explain the process of this invention.
~3~
Example 1 Isobutene and chlorine are reacted in a jacket cooled tubular reactor in a molar ratio of 1.04 : 1 to methallyl chloride as the primary reaction product. The reactants are introduced into the reac'or by way of a two-fluid nozzle. The pressure ranges on the average around 1.6 bar (absolute). The reaction temperature is measured after a reaction route of 4, 8, and 12 meters (measuring points T4, T8 and T12). The reaction is "stabilized" wi-th 0.07 vol-% of air, corresponding to 0.013 vol-% of oxygen.
In order to demonstrate the stabilizing effect of the added oxygen, the oxygen feed was interrupted for testing purposes. Thereupon the reaction temperature rose, after a reaction route of 4 meters, from 94 to 220 C within 4 min-lS utes. The rise proceeded almost linearly. The reintroductionof oxygen in the original quantity resulted, within about 10 minutes in restoration of the original temperature level.
similar interruption in oxygen feed in a case of trouble in the installation resulted in a "runaway"
reaction; the reaction temperature reached values of above 400 C, and strong soot formation began; the installation had to be shut down.
Thy tabls jet out below gives an overview ox the temperature profiLe with the aforementioned, expexi~ental interruption of oxygen fled.
~33~
. . . .
Time Oxygen Content ! Temp-oratu:res min. of Gasous Feed ¦ T4 To i T12 Mixture vol-~ C C C
__ ____ _ ___ ---__ __. ___ _ _ _ ___ . __ _ _ __ ___ _ I_ ___ ___ 5 -10 O oO13 94 88 64 O O 000 9~ 188 64 1 0~000 113 194 66
2 0.000 L50 ~100 67
3 0 . 000 190 11~4 6~
4 Ox 013 ~18 lO~i 69 0~013 195 9~ 66 6 0~013 135 90 64 13 O ~013 ~?4 88 63 ___ _ _~_____________ ______ __~
Exan~le 2 Methallyl chloride is produced as described in Ex-ankle 1, but using a different oxygen content and tempo-rarily without special mixing.
The dosed amount of air is 0 . 44 vol-%, c:orrespond-20 ing to 0 . 088 vol-% of oxygen based on the sum total of gaseous ~eedstock; the adding step takes place without any spec:ial rnixin~ d~vlces on the side of chlorine upstreara of the two- f luid no z z le .
In order to check the amount of oxygen required for 25 stabilizing the reac'cion, the amount of air introduced is halved. Thereupon the reaction temperature vises, aflter a reaction route o 4 meters, withln about 5 minutes f:rom 88 ~3~
Jo 141 C. An observation of the temperature profile over the following 15 minutes shows that the reaction apparently can just barely be operated in a stable fash.ion even under these conditions. However, analysis ox the reaction mixture reveals a drop in the methallyl chloride yield from 85~
to 80-82~ (based on the amount of isobutene stoichiometric-ally required according to the reaction equation C4H8 C12~ C4~7Cl + HCl).
The attempt was made, directly following this test, to mix the reduced quantity of air especially thoroughly with the chlorine stream. For this purpose, the influx velocity of the air into the chlorine was increased by raising the pressure drop between feed air and chlorine at the charging vaLve; while initially the expansion ratio was maintained intenkionally at a low level, with a value of about 1.1, this value was then raised to between 1.5 and 2Ø It was found that this improvement in mixing of the reaction stabilizer with the feed gases was already enough to cause return of the temperature conditions to the levels present with the use of twice the amount of air; thi5, in turn, resulted in restoration of the original (higher) methallyl chloride yield.
The tab}e set forth below gives a overview of the measured data obtained:
~.~3~
, I
t ., , Ul ~~ N1~ D O tN O a o I coo o o o o o o a I o o I O O N I) ~4 anal CO X a t ---- -!
pa I,, o oo o ooo o o o o o o o, 1 I . . . . I f o o, o oo o ooo o o o o o o o, O
, ., , l I al - - N -_-I I O
I h I f I
I Q~ O I
C _ O _ Z
I N )-I I O
I X I O O
o 2: 1 æz I a) . ' ' aa o In o o ,~
I E^i ~3 1 1 --`
_ ., L .
~3~ 5 Example 3 Methallyl chloride is produced from isobutene and chlorine in the gaseous phase according to the description of Example 1, but with differen-t proportions of oxygen at differ-ing points in time.
Chlorine from a diaphragm electrolvsis is utilized.
Oxygen in the form of air is added to this chlorine as the reaction stabilizer; the proportlon, based on total feed, is 1.1 vol-%. After a reaction route of 4 meters, the reaction temperature is 103C.
This "normal procedure" is interrupted for testing purposes. Hydrogen chloride is added in place of air, namely with a quantity of 0.34 vol-%, based on total feed. There is no change in the reac-tion characteristic.
A subsequent experimental shutoff of hydrogen chloride feed leads, within 2 minutes, to an almost linear rise in reaction temperature to 140C, which clearly indicates the "runaway" of the reaction with continued lack of hydrogen chloride as the reaction stabilizer. The thereupon resumed feeding of hydrogen chloride effects restoration of the original reaction condition within about 15 minutes.
Thereafter the hydrogen chloride proportion is lowered from 0.34 to 0.12 vol-%. As a direct consequence, a (comparatively gradual) increase in reaction temperature from 103 to 110-115C can be observed. The condition of the reaction remains stable at this temperature level for at least 20 hours.
~3~
Example 4 Methallyl chloride is produced from isobutene and chlorine in the gaseous phase as describecl in Example 1, but feeding oxygen in this case in the form of pure oxygen with an amount of 0.020 vol-%, based on total feed.
The ambient temperature level is almost identical to that demonstrated in Example 1.
The experimental interruption of oxygen feed leads to an immediate rise in reaction temperature. After 5 min-utes of operating without oxygen dosing, the measuring pointT4 indicates a temperature of a little above 200 C. The re-introduction of oxygen in the aforementioned quantity at this point in time effects return of the temperature level to its original condition within 10~15 minutes.
The temperature profile in detail differs so little from that demonstrated in Example 1 thaw a renewed presentation can be dispensed with; instead, attention is invited to the tabular data in Example 1.
-ln-
Exan~le 2 Methallyl chloride is produced as described in Ex-ankle 1, but using a different oxygen content and tempo-rarily without special mixing.
The dosed amount of air is 0 . 44 vol-%, c:orrespond-20 ing to 0 . 088 vol-% of oxygen based on the sum total of gaseous ~eedstock; the adding step takes place without any spec:ial rnixin~ d~vlces on the side of chlorine upstreara of the two- f luid no z z le .
In order to check the amount of oxygen required for 25 stabilizing the reac'cion, the amount of air introduced is halved. Thereupon the reaction temperature vises, aflter a reaction route o 4 meters, withln about 5 minutes f:rom 88 ~3~
Jo 141 C. An observation of the temperature profile over the following 15 minutes shows that the reaction apparently can just barely be operated in a stable fash.ion even under these conditions. However, analysis ox the reaction mixture reveals a drop in the methallyl chloride yield from 85~
to 80-82~ (based on the amount of isobutene stoichiometric-ally required according to the reaction equation C4H8 C12~ C4~7Cl + HCl).
The attempt was made, directly following this test, to mix the reduced quantity of air especially thoroughly with the chlorine stream. For this purpose, the influx velocity of the air into the chlorine was increased by raising the pressure drop between feed air and chlorine at the charging vaLve; while initially the expansion ratio was maintained intenkionally at a low level, with a value of about 1.1, this value was then raised to between 1.5 and 2Ø It was found that this improvement in mixing of the reaction stabilizer with the feed gases was already enough to cause return of the temperature conditions to the levels present with the use of twice the amount of air; thi5, in turn, resulted in restoration of the original (higher) methallyl chloride yield.
The tab}e set forth below gives a overview of the measured data obtained:
~.~3~
, I
t ., , Ul ~~ N1~ D O tN O a o I coo o o o o o o a I o o I O O N I) ~4 anal CO X a t ---- -!
pa I,, o oo o ooo o o o o o o o, 1 I . . . . I f o o, o oo o ooo o o o o o o o, O
, ., , l I al - - N -_-I I O
I h I f I
I Q~ O I
C _ O _ Z
I N )-I I O
I X I O O
o 2: 1 æz I a) . ' ' aa o In o o ,~
I E^i ~3 1 1 --`
_ ., L .
~3~ 5 Example 3 Methallyl chloride is produced from isobutene and chlorine in the gaseous phase according to the description of Example 1, but with differen-t proportions of oxygen at differ-ing points in time.
Chlorine from a diaphragm electrolvsis is utilized.
Oxygen in the form of air is added to this chlorine as the reaction stabilizer; the proportlon, based on total feed, is 1.1 vol-%. After a reaction route of 4 meters, the reaction temperature is 103C.
This "normal procedure" is interrupted for testing purposes. Hydrogen chloride is added in place of air, namely with a quantity of 0.34 vol-%, based on total feed. There is no change in the reac-tion characteristic.
A subsequent experimental shutoff of hydrogen chloride feed leads, within 2 minutes, to an almost linear rise in reaction temperature to 140C, which clearly indicates the "runaway" of the reaction with continued lack of hydrogen chloride as the reaction stabilizer. The thereupon resumed feeding of hydrogen chloride effects restoration of the original reaction condition within about 15 minutes.
Thereafter the hydrogen chloride proportion is lowered from 0.34 to 0.12 vol-%. As a direct consequence, a (comparatively gradual) increase in reaction temperature from 103 to 110-115C can be observed. The condition of the reaction remains stable at this temperature level for at least 20 hours.
~3~
Example 4 Methallyl chloride is produced from isobutene and chlorine in the gaseous phase as describecl in Example 1, but feeding oxygen in this case in the form of pure oxygen with an amount of 0.020 vol-%, based on total feed.
The ambient temperature level is almost identical to that demonstrated in Example 1.
The experimental interruption of oxygen feed leads to an immediate rise in reaction temperature. After 5 min-utes of operating without oxygen dosing, the measuring pointT4 indicates a temperature of a little above 200 C. The re-introduction of oxygen in the aforementioned quantity at this point in time effects return of the temperature level to its original condition within 10~15 minutes.
The temperature profile in detail differs so little from that demonstrated in Example 1 thaw a renewed presentation can be dispensed with; instead, attention is invited to the tabular data in Example 1.
-ln-
Claims (6)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the production of methallyl chloride, comprising reacting isobutene and chlorine in the gaseous phase in the presence of from 0.001 to 1 vol. % of oxygen or from 0.01 to 5 vol. % of hydrogen chloride as a reaction stabilizer thoroughly mixed with the reactants.
2. A process according to claim 1, wherein the oxygen content is from 0.01 to 0.5 vol. %.
3. A process according to claim 1, wherein the required oxygen is supplied in the form of air.
4. A process according to claim 1, 2 or 3, wherein oxygen is mixed with the reactants before the beginning of the reaction.
5. A process according to claim 1, 2 or 3, wherein the reactant chlorine contains the required amount of oxygen.
6. A process according to claim 1, wherein the reactant chlorine contains the dichloromonoxide impurity and hydrogen chloride is employed as the reaction stabilizer.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843402446 DE3402446A1 (en) | 1984-01-25 | 1984-01-25 | METHOD FOR PRODUCING METHALLYL CHLORIDE |
| DEP3402446.8 | 1984-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1233485A true CA1233485A (en) | 1988-03-01 |
Family
ID=6225830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000472715A Expired CA1233485A (en) | 1984-01-25 | 1985-01-24 | Process for the production of methallyl chloride |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0150317B1 (en) |
| JP (1) | JPS60222430A (en) |
| AT (1) | ATE25963T1 (en) |
| CA (1) | CA1233485A (en) |
| DE (2) | DE3402446A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5397179A (en) * | 1992-08-28 | 1995-03-14 | Turbocom, Inc. | Method and apparatus for mixing fluids |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108164389B (en) * | 2018-01-29 | 2020-07-10 | 浙江大学 | Synthesis method and synthesis reactor of high-selectivity 2-methylallyl chloride |
| CN108299151B (en) | 2018-02-09 | 2020-03-10 | 浙江大学 | Method for preparing 2-methylallyl chloride from 1, 2-dichlorotert-butyl alkane |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1281430B (en) * | 1966-04-02 | 1968-10-31 | Chiyoda Chem Eng Construct Co | Process for the preparation of methallyl chloride |
-
1984
- 1984-01-25 DE DE19843402446 patent/DE3402446A1/en not_active Withdrawn
- 1984-11-27 EP EP84114293A patent/EP0150317B1/en not_active Expired
- 1984-11-27 AT AT84114293T patent/ATE25963T1/en not_active IP Right Cessation
- 1984-11-27 DE DE8484114293T patent/DE3462683D1/en not_active Expired
-
1985
- 1985-01-24 CA CA000472715A patent/CA1233485A/en not_active Expired
- 1985-01-24 JP JP60009980A patent/JPS60222430A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5397179A (en) * | 1992-08-28 | 1995-03-14 | Turbocom, Inc. | Method and apparatus for mixing fluids |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0150317B1 (en) | 1987-03-18 |
| ATE25963T1 (en) | 1987-04-15 |
| DE3462683D1 (en) | 1987-04-23 |
| JPH0471058B2 (en) | 1992-11-12 |
| DE3402446A1 (en) | 1985-07-25 |
| EP0150317A1 (en) | 1985-08-07 |
| JPS60222430A (en) | 1985-11-07 |
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