GB2116546A - Production of t-butyl alkyl ethers - Google Patents
Production of t-butyl alkyl ethers Download PDFInfo
- Publication number
- GB2116546A GB2116546A GB08304536A GB8304536A GB2116546A GB 2116546 A GB2116546 A GB 2116546A GB 08304536 A GB08304536 A GB 08304536A GB 8304536 A GB8304536 A GB 8304536A GB 2116546 A GB2116546 A GB 2116546A
- Authority
- GB
- United Kingdom
- Prior art keywords
- process according
- reactors
- reactor
- butadiene
- weight
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/06—Diethyl ether
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
In producing t-butyl alkyl ethers by etherifying with aliphatic alcohols isobutene in a hydrocarbon feedstock containing butadiene in addition to the isobutene, the increase in the pressure drop in the etherification reactor(s) that is due to the butadiene is eliminated by feeding the reactants from the bottom upwards. The reactors preferably contain an acidic ion-exchange resin catalyst.
Description
SPECIFICATION
Production of t-butyl alkyl ethers
This invention relates to a process for producing t-butyl alkyl ethers in the presence of butadiene.
The addition reaction of alcohols to tertiary olefins such as isobutene to produce t-butyl alkyl
ethers is an exothermic reaction which is acid catalysed. In the presence of suitable catalysts, such as
macroporous ion-exchange resins, the reaction proceeds to equilibrium in times which are of industrial
interest, even at relatively low temperatures (40-500C).
It is known that it is not necessary to operate with high purity isobutene; instead, any cut which
contains it is suitable, as the alcohol addition takes place selectively at the double bonds which are
bonded to a tertiary carbon atom. Cuts from catalytic cracking and cuts from steam cracking, the latter
either before or after extraction of butadiene, are particularly suitable.
When using as olefin feedstock the C4 fraction from catalytic cracking or from steam cracking afte
extraction of butadiene, and using methanol or ethanol as the alcohol and a sulphonic macroporous
resin type catalyst, namely Amberlyst (RTM) 1 5 or lewatit (RTM) SPC 108, the reaction can be carried
out industrially in a wide range of reactor designs and under a wide range of operating conditions,
directed towards optimising the conversion of one or other of the reactants. In these cases, a high selectivity is obtained, together with good performance of the catalyst both in terms of catalytic activity and life.
When operating with an olefin cut with a high butadiene content, such as the C4 cut from steam
cracking before extraction of butadiene, the operating conditions must be accurately defined in order to
obtain a butadiene recovery exceeding 9899%. In particular, it is necessary to maintain a strict
relationship between the temperature and spacial velocity, as described in US-A-4039590.
It has however been noted that when carrying out the isobutene etherification reaction in the presence of butadiene in a tubular reactor containing a macroporous resin, and feeding the reactants from the top downwards in the normal manner, an increase in the pressure drop takes place with time, even when operating under conditions which allow a high butadiene recovery of 99% or more, and in addition a slight conversion fall-off takes place with time.
However, an identical test carried out with a butadiene-free cut shows neither a pressure drop increase not a conversion reduction. It has been surprisingly found, in accordance with the present invention, that by feeding the butadiene-containing feedstock so that it flows from the bottom upwards,
under slight bed expansion conditions, the pressure drop remains constant with time.
The process according to the present invention comprises producing one or more t-butyl alkyl ethers, by reacting isobutene of a hydrocarbon feedstock, which feedstock contains butadiene in an amount of from 10 to 70% by weight, with one or more aliphatic alcohols, preferably methanol or ethanol, in one, two or more reactors, preferably in series. The process is characterised in that the reactants (i.e. the hydrocarbon feedstock containing butadiene and the alcohol or alcohols) and the
reaction products flow through the reactor or reactors, which preferably contain a macroporous acidic ion-exchange resin catalyst, from the bottom upwards.
The linear velocity of the reactants through the reactor or reactors is preferably from 0.5 to 2 cm/sec. The temperature in the reactor or reactors is preferably from 50 to 600 C, more preferably from 50 to 550C.
The invention will now be illustrated by the following Example and Comparative Examples, wherein the abbreviation "MTBE" means "methyl t-butyl ether".
EXAMPLE 1
There was used a C4 cut having the following composition:
Propylene 0.46% by weight
Isobutane 6.87% by weight
n-Butane 11.80% by weight
Butene-1 1 1.39% by weight
Isobutene 30.19% by weight
Butene-2 + 3.2 5% by weight
Cis-butene-2 1.55% by weight
Butadiene 34.43% by weight
The cut was mixed with methanol such that the isobutene:methanol molar ratio was 0.85:1. The
mixture was fed at a throughput of 14 litres/hour and a temperature of 500C through two reactors connected in series, having a total capacity of 4.5 litres and filled with 4 litres of catalyst. The catalyst was a macroporous sulphonic resin with an exchange capacity of 4.8 meq H+/g dry. The reactants flowed from the bottom upwards. The linear velocity was 1 cm/sec.
The conversion and pressure drops with respect to time were as given in the following Table 1.
TABLE 1
Time (hours) 24 500 2000 Pressure drop in 1 sot reactor (kg/cm2) 0.2 0.2 0.2 Pressure drop in 2nd reactor (kg/cm2) 0.2 0.2 0.2 MTBE (% by weight) 38.1 38 38 Dimers and codimers (% by weight) 0.05 0.05 0.05 Butenyl ethers (% by weight) 0.2 0.15 0.2 Isobutene conversion 96.6 96.4 96.4 Butadiene recovery > 99 > 99 > 99 EXAMPLE 2 (comparative)
The feedstock described in the preceding Example was fed under the same temperature and spacial velocity conditions to the two reactors connected in series, but in such a manner that the flow direction of the reactants was from the top downwards.
At the beginning of the test, the results were analogous to those of the preceding Example, but as time passed a progressive pressure drop increase and a slight conversion fall-off were observed, as can be seen from the following Table 2.
TABLE 2
Time (hours) 24 500 2000 Pressure drop in 1 st reactor (kg/cm2) 0.3 0.4 1.5 Pressure drop in 2nd reactor (kg/cm2) 0.3 0.5 1.8 MTBE (% by weight) 38 37.9 36 Dimers and codimers (% by weight) 0.1 0.1 0.05 Butenyl ethers (% by weight) 0.2 0.2 0.2 isobutene conversion 96.4 96.1 91.3 Butadiene recovery > 99 > 99 > 99 EXAMPLE 3 (comparative)
Methanol was added to an olefin cut containing 35% by weight of isobutene and 0.2% by weight of butadiene, such that the isobutene:methanol molar ratio was 0.85:1. The mixture was fed at a throughput of 1 4 litres/hour and a temperature of 500C to the two reactors connected in series, the flow direction being from the top downwards. In the absence of butadiene, no pressure drop increase or conversion fall-off with time were observed, as can be seen from the following table 3.
TABLE 3
Time (hours) 24 500 2000 Pressure drop in 1 sot reactor (kg/cm2) 0.3 0.3 0.3 Pressure drop in 2nd reactor (kg/cm2) 0.3 0.3 0.3 MTBE (% by weight) 43.1 42.9 43 Dimers and codimers (% by weight) 0.3 0.3 0.2 Isobutene conversion 96.8 96.6 96.6
Claims (9)
1. A process for producing one or more t-butyl alkyl ethers, which comprises reacting isobutene of a hydrocarbon feedstock, which feedstock contains butadiene in an amount of from 10 to 70% by weight, with one or more aliphatic alcohols in one or more reactors, the reactants and the reaction products being made to flow from the bottom upwards through the reactor or reactors.
2. A process according to claim 1 , wherein the reactants have a linear velocity of from 0.5 to 2 cm/sec.
3. A process according to claim 1 or 2, wherein the temperature in the reactor or reactors is from 50 to 600C.
4. A process according to claim 3, wherein the temperature in the reactor or reactors is from 50 to 550C.
5. A process according to any of claims 1 to 4, wherein the alcohol is methanol or ethanol.
6. A process according to any of claims 1 to 5, wherein the reaction is carried out in two or more reactors in series.
7. A process according to any of claims 1 to 6, wherein the reactor or reactors contain a catalyst comprising a macroporous acidic ion-exchange resin.
8. A process according to claim 1, substantially as described in the foregoing Example 1.
9. A t-butyl alkyl ether produced by a process according to any of claims 1 to 8.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT20122/82A IT1150678B (en) | 1982-03-12 | 1982-03-12 | PROCEDURE FOR THE PRODUCTION OF TERBUTYL ALCHYL ETHERS IN THE PRESENCE OF BUTADIENE |
Publications (3)
Publication Number | Publication Date |
---|---|
GB8304536D0 GB8304536D0 (en) | 1983-03-23 |
GB2116546A true GB2116546A (en) | 1983-09-28 |
GB2116546B GB2116546B (en) | 1986-01-02 |
Family
ID=11163984
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB08304536A Expired GB2116546B (en) | 1982-03-12 | 1983-02-18 | Production of t-butyl alkyl ethers |
Country Status (33)
Country | Link |
---|---|
JP (1) | JPS58167534A (en) |
KR (1) | KR860001359B1 (en) |
AT (1) | AT387959B (en) |
AU (1) | AU559931B2 (en) |
BE (1) | BE896127A (en) |
BR (1) | BR8301020A (en) |
CA (1) | CA1205824A (en) |
CS (1) | CS232749B2 (en) |
DD (1) | DD207194A5 (en) |
DE (1) | DE3308736A1 (en) |
DK (1) | DK65683A (en) |
EG (1) | EG16276A (en) |
ES (1) | ES520857A0 (en) |
FR (1) | FR2523121B1 (en) |
GB (1) | GB2116546B (en) |
GR (1) | GR78796B (en) |
HU (1) | HU196351B (en) |
IN (1) | IN159879B (en) |
IT (1) | IT1150678B (en) |
LU (1) | LU84665A1 (en) |
MX (1) | MX155984A (en) |
NL (1) | NL8300848A (en) |
NO (1) | NO156606C (en) |
NZ (1) | NZ203293A (en) |
PH (1) | PH19851A (en) |
PL (1) | PL140559B1 (en) |
PT (1) | PT76375B (en) |
RU (1) | RU1836318C (en) |
SE (1) | SE461853B (en) |
TR (1) | TR21654A (en) |
YU (1) | YU49483A (en) |
ZA (1) | ZA831152B (en) |
ZM (1) | ZM1583A1 (en) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1987007259A1 (en) * | 1986-05-27 | 1987-12-03 | Snamprogetti S.P.A. | Process for preparing alkyl-tert-butyl ethers |
EP0490571A2 (en) * | 1990-12-13 | 1992-06-17 | The British Petroleum Company P.L.C. | Hydrogenation process |
US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
US7847139B2 (en) | 2003-07-15 | 2010-12-07 | Grt, Inc. | Hydrocarbon synthesis |
US7880041B2 (en) | 2004-04-16 | 2011-02-01 | Marathon Gtf Technology, Ltd. | Process for converting gaseous alkanes to liquid hydrocarbons |
US7883568B2 (en) | 2006-02-03 | 2011-02-08 | Grt, Inc. | Separation of light gases from halogens |
US7964764B2 (en) | 2003-07-15 | 2011-06-21 | Grt, Inc. | Hydrocarbon synthesis |
US7998438B2 (en) | 2007-05-24 | 2011-08-16 | Grt, Inc. | Zone reactor incorporating reversible hydrogen halide capture and release |
US8008535B2 (en) | 2004-04-16 | 2011-08-30 | Marathon Gtf Technology, Ltd. | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
US8053616B2 (en) | 2006-02-03 | 2011-11-08 | Grt, Inc. | Continuous process for converting natural gas to liquid hydrocarbons |
US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
US8198495B2 (en) | 2010-03-02 | 2012-06-12 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
US8273929B2 (en) | 2008-07-18 | 2012-09-25 | Grt, Inc. | Continuous process for converting natural gas to liquid hydrocarbons |
US8282810B2 (en) | 2008-06-13 | 2012-10-09 | Marathon Gtf Technology, Ltd. | Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery |
US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
US8802908B2 (en) | 2011-10-21 | 2014-08-12 | Marathon Gtf Technology, Ltd. | Processes and systems for separate, parallel methane and higher alkanes' bromination |
US8815050B2 (en) | 2011-03-22 | 2014-08-26 | Marathon Gtf Technology, Ltd. | Processes and systems for drying liquid bromine |
US8829256B2 (en) | 2011-06-30 | 2014-09-09 | Gtc Technology Us, Llc | Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons |
US9193641B2 (en) | 2011-12-16 | 2015-11-24 | Gtc Technology Us, Llc | Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems |
US9206093B2 (en) | 2004-04-16 | 2015-12-08 | Gtc Technology Us, Llc | Process for converting gaseous alkanes to liquid hydrocarbons |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8686211B2 (en) | 2011-09-07 | 2014-04-01 | Shell Oil Company | Process for preparing ethylene and/or propylene and a butadiene-enriched product |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1506461A (en) * | 1974-05-21 | 1978-04-05 | Snam Progetti | Production of alkyl tertiary butyl ethers |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1224294B (en) * | 1961-01-09 | 1966-09-08 | Bayer Ag | Process for the production of tertiary butyl alkyl ethers |
JPS4961109A (en) * | 1972-10-12 | 1974-06-13 | ||
JPS5220963A (en) * | 1975-06-30 | 1977-02-17 | Daido Steel Co Ltd | Method of manufacturing precious metal powder |
JPS5232241A (en) * | 1975-09-05 | 1977-03-11 | Fujitsu Ltd | Wireless data transmission system |
FR2440931A1 (en) * | 1978-11-08 | 1980-06-06 | Inst Francais Du Petrole | PROCESS FOR PRODUCING ETHERS BY REACTION OF OLEFINS WITH ALCOHOLS |
DE2928509A1 (en) * | 1979-07-14 | 1981-01-29 | Basf Ag | METHOD FOR THE SIMULTANEOUS PRODUCTION OF METHYL-TERT.-BUTYL ETHER AND PRODUCTION OF ISOBUTEN |
JPS58146524A (en) * | 1982-02-25 | 1983-09-01 | Mitsubishi Gas Chem Co Inc | Preparation of tertiary ether |
-
1982
- 1982-03-12 IT IT20122/82A patent/IT1150678B/en active
-
1983
- 1983-02-15 DK DK65683A patent/DK65683A/en not_active Application Discontinuation
- 1983-02-15 NZ NZ203293A patent/NZ203293A/en unknown
- 1983-02-16 CA CA000421707A patent/CA1205824A/en not_active Expired
- 1983-02-18 GB GB08304536A patent/GB2116546B/en not_active Expired
- 1983-02-21 ZA ZA831152A patent/ZA831152B/en unknown
- 1983-02-21 KR KR1019830000697A patent/KR860001359B1/en active IP Right Grant
- 1983-02-22 AU AU11744/83A patent/AU559931B2/en not_active Expired - Fee Related
- 1983-02-23 GR GR70589A patent/GR78796B/el unknown
- 1983-02-24 PL PL1983240765A patent/PL140559B1/en unknown
- 1983-02-25 BR BR8301020A patent/BR8301020A/en unknown
- 1983-02-25 LU LU84665A patent/LU84665A1/en unknown
- 1983-02-25 SE SE8301069A patent/SE461853B/en not_active IP Right Cessation
- 1983-02-25 MX MX196394A patent/MX155984A/en unknown
- 1983-03-02 YU YU00494/83A patent/YU49483A/en unknown
- 1983-03-03 CS CS831493A patent/CS232749B2/en unknown
- 1983-03-04 NO NO830743A patent/NO156606C/en unknown
- 1983-03-07 ZM ZM15/83A patent/ZM1583A1/en unknown
- 1983-03-08 AT AT0080383A patent/AT387959B/en not_active IP Right Cessation
- 1983-03-08 PH PH28617A patent/PH19851A/en unknown
- 1983-03-09 NL NL8300848A patent/NL8300848A/en not_active Application Discontinuation
- 1983-03-09 TR TR21654A patent/TR21654A/en unknown
- 1983-03-10 BE BE0/210292A patent/BE896127A/en not_active IP Right Cessation
- 1983-03-11 ES ES520857A patent/ES520857A0/en active Granted
- 1983-03-11 PT PT76375A patent/PT76375B/en unknown
- 1983-03-11 DD DD83248748A patent/DD207194A5/en not_active IP Right Cessation
- 1983-03-11 RU SU833560849A patent/RU1836318C/en active
- 1983-03-11 HU HU83846A patent/HU196351B/en unknown
- 1983-03-11 FR FR8304015A patent/FR2523121B1/en not_active Expired
- 1983-03-11 JP JP58039308A patent/JPS58167534A/en active Granted
- 1983-03-11 IN IN302/CAL/83A patent/IN159879B/en unknown
- 1983-03-11 DE DE19833308736 patent/DE3308736A1/en active Granted
- 1983-03-12 EG EG167/83A patent/EG16276A/en active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1506461A (en) * | 1974-05-21 | 1978-04-05 | Snam Progetti | Production of alkyl tertiary butyl ethers |
Cited By (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1987007259A1 (en) * | 1986-05-27 | 1987-12-03 | Snamprogetti S.P.A. | Process for preparing alkyl-tert-butyl ethers |
EP0490571A2 (en) * | 1990-12-13 | 1992-06-17 | The British Petroleum Company P.L.C. | Hydrogenation process |
EP0490571A3 (en) * | 1990-12-13 | 1993-01-20 | The British Petroleum Company P.L.C. | Hydrogenation process |
US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
US8415512B2 (en) | 2001-06-20 | 2013-04-09 | Grt, Inc. | Hydrocarbon conversion process improvements |
US7964764B2 (en) | 2003-07-15 | 2011-06-21 | Grt, Inc. | Hydrocarbon synthesis |
US7847139B2 (en) | 2003-07-15 | 2010-12-07 | Grt, Inc. | Hydrocarbon synthesis |
US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
US9206093B2 (en) | 2004-04-16 | 2015-12-08 | Gtc Technology Us, Llc | Process for converting gaseous alkanes to liquid hydrocarbons |
US7880041B2 (en) | 2004-04-16 | 2011-02-01 | Marathon Gtf Technology, Ltd. | Process for converting gaseous alkanes to liquid hydrocarbons |
US8008535B2 (en) | 2004-04-16 | 2011-08-30 | Marathon Gtf Technology, Ltd. | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
US8232441B2 (en) | 2004-04-16 | 2012-07-31 | Marathon Gtf Technology, Ltd. | Process for converting gaseous alkanes to liquid hydrocarbons |
US7883568B2 (en) | 2006-02-03 | 2011-02-08 | Grt, Inc. | Separation of light gases from halogens |
US8053616B2 (en) | 2006-02-03 | 2011-11-08 | Grt, Inc. | Continuous process for converting natural gas to liquid hydrocarbons |
US8921625B2 (en) | 2007-02-05 | 2014-12-30 | Reaction35, LLC | Continuous process for converting natural gas to liquid hydrocarbons |
US7998438B2 (en) | 2007-05-24 | 2011-08-16 | Grt, Inc. | Zone reactor incorporating reversible hydrogen halide capture and release |
US8282810B2 (en) | 2008-06-13 | 2012-10-09 | Marathon Gtf Technology, Ltd. | Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery |
US8273929B2 (en) | 2008-07-18 | 2012-09-25 | Grt, Inc. | Continuous process for converting natural gas to liquid hydrocarbons |
US8415517B2 (en) | 2008-07-18 | 2013-04-09 | Grt, Inc. | Continuous process for converting natural gas to liquid hydrocarbons |
US8198495B2 (en) | 2010-03-02 | 2012-06-12 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
US9133078B2 (en) | 2010-03-02 | 2015-09-15 | Gtc Technology Us, Llc | Processes and systems for the staged synthesis of alkyl bromides |
US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
US8815050B2 (en) | 2011-03-22 | 2014-08-26 | Marathon Gtf Technology, Ltd. | Processes and systems for drying liquid bromine |
US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
US8829256B2 (en) | 2011-06-30 | 2014-09-09 | Gtc Technology Us, Llc | Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons |
US8802908B2 (en) | 2011-10-21 | 2014-08-12 | Marathon Gtf Technology, Ltd. | Processes and systems for separate, parallel methane and higher alkanes' bromination |
US9193641B2 (en) | 2011-12-16 | 2015-11-24 | Gtc Technology Us, Llc | Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19990218 |