GB2147290A - Alcohols from liquid petroleum gas - Google Patents

Alcohols from liquid petroleum gas Download PDF

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Publication number
GB2147290A
GB2147290A GB8326026A GB8326026A GB2147290A GB 2147290 A GB2147290 A GB 2147290A GB 8326026 A GB8326026 A GB 8326026A GB 8326026 A GB8326026 A GB 8326026A GB 2147290 A GB2147290 A GB 2147290A
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United Kingdom
Prior art keywords
mtbe
methanol
sba
ipa
mixture
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.)
Withdrawn
Application number
GB8326026A
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GB8326026D0 (en
Inventor
Michael John Pettman
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Humphreys and Glasgow Ltd
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Humphreys and Glasgow Ltd
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Publication date
Application filed by Humphreys and Glasgow Ltd filed Critical Humphreys and Glasgow Ltd
Priority to GB8326026A priority Critical patent/GB2147290A/en
Publication of GB8326026D0 publication Critical patent/GB8326026D0/en
Publication of GB2147290A publication Critical patent/GB2147290A/en
Withdrawn legal-status Critical Current

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    • 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
    • C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • 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
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00—Fermentation processes for beer
    • C12C11/02—Pitching yeast

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Isopropyl alcohol, secondary butyl alcohol, methyl tertiary butyl ether, or a mixture of at least two thereof are produced from liquid petroleum gas by dehydrogenating propane, n-butane, iso-butane, or a mixture of at least two thereof in the gas to propylene, n-butylene, and iso-butylene, respectively, and then etherifying with methanol and/or hydrating the dehydrogenated gas to yield isopropyl alcohol, secondary butyl alcohol, methyl tertiary butyl ether, or a mixture of at least two thereof. The alcohols and ether can be used as automobile petrol additives, particularly when mixed with methanol.

Description

SPECIFICATION Alcohols from LPGs This patent relates to the production of isopropyl alcohol (IPA), secondary butyl alcohol (SBA) and methyl tertiary butyl ether (MTBE) from liquid petroleum gases (LPG).
IPA, SBA, and MTBE have good petroleum blending octane characteristics and may be used in combination as petroleum additives. IPA and SBA also have gasoline co-solubility properties, i.e. they increase the solubility of methanol in petrol. The present invention utilises LPGs without significant distillation or isomerisation to manufacture IPA, SBA and MTBE.
The entire LPG fraction containing propane, normal and isobutane is dehydrogenated simultaneously to a mixture containing propylene, normal butylene and isobutylene. This stream, containing some unconverted paraffins, is passed to an etherification section where methanol is reacted with the isobutylene to produce MTBE. The methanol may be produced from an integrated methanol plant.
The normal butenes and propylene, which only react to a very small degree under the conditions used for MTBE production, are hydrated simultaneously with water in a subsequent hydration section to produce SBA and IPA. Unconverted paraffins are re-cycled to the dehydrogenation section.
Thus a petroleum additive containing methanol, MTBE, SBA and IPA can be produced. Alternatively MTBE may be separately produced as this is not difficult because the MTBE reactor produces MTBE in the liquid phase whilst the unreacted olefins carry through into the vapour phase.
An advantage of this process is that separation of the LPG components of propane and normal and isobutane is not required. A further advantage is that isomerisation of paraffins is not required. By these means the whole fraction of LPG can be utilised for manufacture of useful gasoline additives and allow larger quantities of methanol to be used in gasoline taking advantage of the co-solubility properties of the alcohols and ether.
Of course this process may also be used to produce IPA or SBA as a product in their own rights should these be required as, e.g., chemical solvents.
1. A process for producing isopropyl alcohol, secondary butyl alcohol, methyl tertiary butyl ether, or a mixture of at least two thereof from liquid petroleum gas, which process comprises dehydrogenating propane, n-butane, iso-butane, or a mixture of at least two thereof in the gas to propylene, n-butylene, and iso-butylene, respectively, and then etherifying with methanol and/or hydrating the dehydrogenated gas to yield isopropyl alcohol, secondary butyl alcohol, methyl tertiary butyl ether, or a mixture of at least two thereof.
2. A process as claimed in claim 1 wherein a mixture of propane, n-butane, and iso-butane are simultaneously dehydrated, etherified and hydrated, the conditions of the etherifying step being such that substantially none of the propylene or nbutylene is etherified.
3. A process as claimed in claim 1 or claim 2 wherein the etherifying step is carried out in the vapour phase, and wherein the product methyl tertiary butyl ether is produced in the liquid phase.
4. A process as claimed in any one of the preceding claims including the step of recycling unreacted gas to the dehydrogenating step.
5. Isopropyl alcohol, secondary butyl alcohol, methyl tertiary butyl ether, or a mixture of at least two thereof when produced by a process as claimed in any one of the preceding claims.
6. A petroleum additive comprising methanol and at least one of the alcohols or ether claimed in claim 5.
7. Automobile petrol comprising as an additive a petroleum additive as claimed in claim 6.
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (7)

**WARNING** start of CLMS field may overlap end of DESC **. SPECIFICATION Alcohols from LPGs This patent relates to the production of isopropyl alcohol (IPA), secondary butyl alcohol (SBA) and methyl tertiary butyl ether (MTBE) from liquid petroleum gases (LPG). IPA, SBA, and MTBE have good petroleum blending octane characteristics and may be used in combination as petroleum additives. IPA and SBA also have gasoline co-solubility properties, i.e. they increase the solubility of methanol in petrol. The present invention utilises LPGs without significant distillation or isomerisation to manufacture IPA, SBA and MTBE. The entire LPG fraction containing propane, normal and isobutane is dehydrogenated simultaneously to a mixture containing propylene, normal butylene and isobutylene. This stream, containing some unconverted paraffins, is passed to an etherification section where methanol is reacted with the isobutylene to produce MTBE. The methanol may be produced from an integrated methanol plant. The normal butenes and propylene, which only react to a very small degree under the conditions used for MTBE production, are hydrated simultaneously with water in a subsequent hydration section to produce SBA and IPA. Unconverted paraffins are re-cycled to the dehydrogenation section. Thus a petroleum additive containing methanol, MTBE, SBA and IPA can be produced. Alternatively MTBE may be separately produced as this is not difficult because the MTBE reactor produces MTBE in the liquid phase whilst the unreacted olefins carry through into the vapour phase. An advantage of this process is that separation of the LPG components of propane and normal and isobutane is not required. A further advantage is that isomerisation of paraffins is not required. By these means the whole fraction of LPG can be utilised for manufacture of useful gasoline additives and allow larger quantities of methanol to be used in gasoline taking advantage of the co-solubility properties of the alcohols and ether. Of course this process may also be used to produce IPA or SBA as a product in their own rights should these be required as, e.g., chemical solvents. CLAIMS
1. A process for producing isopropyl alcohol, secondary butyl alcohol, methyl tertiary butyl ether, or a mixture of at least two thereof from liquid petroleum gas, which process comprises dehydrogenating propane, n-butane, iso-butane, or a mixture of at least two thereof in the gas to propylene, n-butylene, and iso-butylene, respectively, and then etherifying with methanol and/or hydrating the dehydrogenated gas to yield isopropyl alcohol, secondary butyl alcohol, methyl tertiary butyl ether, or a mixture of at least two thereof.
2. A process as claimed in claim 1 wherein a mixture of propane, n-butane, and iso-butane are simultaneously dehydrated, etherified and hydrated, the conditions of the etherifying step being such that substantially none of the propylene or nbutylene is etherified.
3. A process as claimed in claim 1 or claim 2 wherein the etherifying step is carried out in the vapour phase, and wherein the product methyl tertiary butyl ether is produced in the liquid phase.
4. A process as claimed in any one of the preceding claims including the step of recycling unreacted gas to the dehydrogenating step.
5. Isopropyl alcohol, secondary butyl alcohol, methyl tertiary butyl ether, or a mixture of at least two thereof when produced by a process as claimed in any one of the preceding claims.
6. A petroleum additive comprising methanol and at least one of the alcohols or ether claimed in claim 5.
7. Automobile petrol comprising as an additive a petroleum additive as claimed in claim 6.
GB8326026A 1983-09-29 1983-09-29 Alcohols from liquid petroleum gas Withdrawn GB2147290A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB8326026A GB2147290A (en) 1983-09-29 1983-09-29 Alcohols from liquid petroleum gas

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB8326026A GB2147290A (en) 1983-09-29 1983-09-29 Alcohols from liquid petroleum gas

Publications (2)

Publication Number Publication Date
GB8326026D0 GB8326026D0 (en) 1983-11-02
GB2147290A true GB2147290A (en) 1985-05-09

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GB8326026A Withdrawn GB2147290A (en) 1983-09-29 1983-09-29 Alcohols from liquid petroleum gas

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0382956A1 (en) * 1987-10-30 1990-08-22 Uop Process for direct etherification of a dehydrogenation zone effluent stream
WO2008009648A1 (en) * 2006-07-20 2008-01-24 Basf Se Process for preparing isopropanol and 2-butanol from the corresponding alkanes
WO2009074574A1 (en) * 2007-12-10 2009-06-18 Basf Se Method for producing isopropanol and 2-butanol from the corresponding alkanes

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1280600A (en) * 1970-03-26 1972-07-05 British Petroleum Co Improvements relating to the recovery of liquified petroleum gas
GB1369890A (en) * 1971-11-22 1974-10-09 Sun Oil Co Pennsylvania Process for producing 2-methyl-2-methoxypropane and alkylate
GB1377211A (en) * 1971-03-24 1974-12-11 Davy Powergas Ltd Catalyst and oxidation process
GB1398531A (en) * 1972-08-14 1975-06-25 Ashland Oil Inc Dehydrogenation method
GB1444645A (en) * 1974-08-01 1976-08-04 Inst Orch Khim Im Nd Zelinskog Production of aliphatic alcohols
GB1506596A (en) * 1974-05-21 1978-04-05 Snam Progetti Production of tertiary alkyl ethers
GB1580652A (en) * 1976-07-02 1980-12-03 Huels Chemische Werke Ag Process for the manufacture of methyl tertiary butyl ehter
EP0037671A1 (en) * 1980-04-09 1981-10-14 Mobil Oil Corporation Shape selective acid catalyzed reactions of olefins over crystalline zeolites

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1280600A (en) * 1970-03-26 1972-07-05 British Petroleum Co Improvements relating to the recovery of liquified petroleum gas
GB1377211A (en) * 1971-03-24 1974-12-11 Davy Powergas Ltd Catalyst and oxidation process
GB1369890A (en) * 1971-11-22 1974-10-09 Sun Oil Co Pennsylvania Process for producing 2-methyl-2-methoxypropane and alkylate
GB1398531A (en) * 1972-08-14 1975-06-25 Ashland Oil Inc Dehydrogenation method
GB1506596A (en) * 1974-05-21 1978-04-05 Snam Progetti Production of tertiary alkyl ethers
GB1444645A (en) * 1974-08-01 1976-08-04 Inst Orch Khim Im Nd Zelinskog Production of aliphatic alcohols
GB1580652A (en) * 1976-07-02 1980-12-03 Huels Chemische Werke Ag Process for the manufacture of methyl tertiary butyl ehter
EP0037671A1 (en) * 1980-04-09 1981-10-14 Mobil Oil Corporation Shape selective acid catalyzed reactions of olefins over crystalline zeolites

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KIRK-OTHMER ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY 3RD EDITION VOLUME 17 PAGE 227 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0382956A1 (en) * 1987-10-30 1990-08-22 Uop Process for direct etherification of a dehydrogenation zone effluent stream
WO2008009648A1 (en) * 2006-07-20 2008-01-24 Basf Se Process for preparing isopropanol and 2-butanol from the corresponding alkanes
EP2070900A2 (en) 2006-07-20 2009-06-17 Basf Se Method for producing isopropanol and 2-butanol from the corresponding alkanes
US7750194B2 (en) 2006-07-20 2010-07-06 Basf Aktiengesellschaft Process for preparing isopropanol and 2-butanol from the corresponding alkanes
EP2070900A3 (en) * 2006-07-20 2012-01-11 Basf Se Method for producing isopropanol and 2-butanol from the corresponding alkanes
WO2009074574A1 (en) * 2007-12-10 2009-06-18 Basf Se Method for producing isopropanol and 2-butanol from the corresponding alkanes

Also Published As

Publication number Publication date
GB8326026D0 (en) 1983-11-02

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