EP1198442A1 - Utilisation de produits issus de la metathese de produits de traitement fischer-tropsch - Google Patents

Utilisation de produits issus de la metathese de produits de traitement fischer-tropsch

Info

Publication number
EP1198442A1
EP1198442A1 EP00952774A EP00952774A EP1198442A1 EP 1198442 A1 EP1198442 A1 EP 1198442A1 EP 00952774 A EP00952774 A EP 00952774A EP 00952774 A EP00952774 A EP 00952774A EP 1198442 A1 EP1198442 A1 EP 1198442A1
Authority
EP
European Patent Office
Prior art keywords
composition
branching
oxo
branched
drilling fluid
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Withdrawn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
EP00952774A
Other languages
German (de)
English (en)
Inventor
Dave Hedley Morgan
Robin John Nash
Hester De Wet
Jan Mattheus Botha
Sybrandus Kindermans
Alta Spamer
Bongani Simon Nkosi
Muzikayise Mthokozisi Justice Mbatha
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sasol Technology Pty Ltd
Original Assignee
Sasol Technology Pty Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sasol Technology Pty Ltd filed Critical Sasol Technology Pty Ltd
Publication of EP1198442A1 publication Critical patent/EP1198442A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02—Well-drilling compositions
    • C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
    • C09K8/34—Organic liquids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/107—Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
    • 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
    • C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds

Definitions

  • the invention relates to alkyl benzene (AB), drilling fluid and oxo-alcohols
  • Va ⁇ ous heterogeneous contact catalysts such as WO 3 /S1O 2 , Re ⁇ 7 /AI 2 ⁇ 3 and
  • a Fischer-Tropsch process product or feedstock is meant a product obtained by subjecting a synthesis gas including carbon monoxide and hydrogen, to Fischer-Tropsch reaction conditions in the presence of typically an iron based catalyst, a cobalt based catalyst, and iron/cobalt based catalyst, or any other Fischer- Tropsch catalyst under Fischer-Tropsch reaction conditions Summary of the Invention
  • This invention provides products in the 8 to 18 carbon range derived from 5 to 10 carbon Fischer-Tropsch process products, the products in the 8 to 18 carbon range having a desirable degree of branching or non-linearity.
  • an oxo- alcohol composition including oxo-alcohols having from 8 to 18 carbon atoms, the oxo-alcohols being derived from olefins obtained by metathesis of one or more of 5, 6, 7, 8, 9 and/or 10 carbon containing Fischer-Tropsch derived feedstock.
  • oxo-alcohols of the composition may be branched oxo-alcohols, typically between 10% and 90%.
  • the oxo-alcohols of the composition may be predominantly linear, with between 10% and 49% branched oxo-alcohols in the composition.
  • the composition includes between 15% and 35% branched oxo-alcohols.
  • the composition includes 24% branched oxo-alcohols.
  • the branching on the branched oxo-alcohols is predominantly mono-methyl branching, however, some di-methyl branching may also be present.
  • the mono-methyl branching will be in excess of 90% of the branching, or even in excess of 95%.
  • the branching may be predominantly on the C4+ carbon, with some branching present on the C2 carbon.
  • the branching is typically over 70% on the C4+ carbons.
  • the branching may exceed 90% on the C4+ carbons.
  • the oxo-alcohols of the composition in the 8 to 10 carbon range are usable as plasticizer alcohols.
  • the oxo-alcohols of the composition in the 10 to 16 carbon range are usable as detergent alcohols.
  • This product of Table 1 may typically be hydroformylated using a Co-EP catalyst, or any other suitable catalyst, to form predominantly linear alcohols, the ratio of linear to branched alcohols being related to the ratio of linear to branched product of the metathesis of the 7 carbon Fischer-Tropsch derived feedstock.
  • an alkyl benzene (AB) composition including AB having from 10 to 14 carbon atoms on the alkyl chain, the AB being derived from olefins obtained by metathesis of one or more of a 6,7 and/or 8 carbon containing Fischer-Tropsch derived feedstock.
  • the AB composition may contain between 10% and 90% of branched alkyl chain AB.
  • the AB composition may contain predominantly linear alkyl chain AB, with between 10% and 49% branched alkyl chain AB in the composition.
  • the composition includes between 15% and 35% branched alkyl chain AB.
  • the composition includes about 24% branched alkyl chain AB.
  • the branching on the branched alkyl chain of the AB is predominantly mono- methyl branching, however, some di-methyl and/or ethy branching may also be present.
  • the mono-methyl branching will be in excess of 90% of the branching, or even in excess of 95%.
  • the branching may be predominantly on the C4+ carbon, with some branching present on the C2 carbon.
  • the branching is typically over 70% on the C4+ carbons.
  • the branching may exceed 90% on the C4+ carbons.
  • a typical AB product make up produced from the products of metathesis of a 9 carbon Fischer-Tropsch derived feedstock is set out in Table 3 at the end of the specification.
  • the AB may be sulfonated to give an alkyl benzene sulfonate which may be used as a detergent.
  • the AB composition itself may have uses such as for drilling fluids.
  • Methyl branched internal olefins in the 10 to 14 carbon range make up most of the remainder.
  • a drilling fluid composition including hydrocarbons having from 14 to 18 carbon atoms, the hydrocarbons being derived from olefins obtained by metathesis of one or more of a 8, 9 and/or 10 carbon containing Fischer-Tropsch derived feedstock.
  • hydrocarbons derived from olefins obtained by metathesis of one or more of a 8, 9 and/or 10 carbon containing Fischer-Tropsch derived feedstock may be internal olefins.
  • the drilling fluid composition may include between 10% and 90% branched hydrocarbons.
  • the hydrocarbons of the drilling fluid composition may be predominantly linear, with between 10% and 49% branched hydrocarbons in the composition.
  • the composition includes between 15% and 35% branched hydrocarbons.
  • the composition includes about 24% branched hydrocarbons.
  • the branching on the branched hydrocarbons is predominantly mono-methyl branching, however, some di-methyl and/or ethyl branching may also be present.
  • the branching may be predominantly on the C4+ carbon, with some branching present on the C2 carbon.
  • the branching is typically over 70% on the C4+ carbons.
  • the branching may exceed 90% on the C4+ carbons.
  • the mono-methyl branching will be in excess of 90% of the branching, or even in excess of 95%.
  • a typical product make up from the metathesis of a 9 carbon Fischer-Tropsch derived feedstock and suitable for deriving the drilling fluid composition is set out in Table 2 at the end of the specification.
  • the product was sulfonated with an equivalent of chlorosulfonic acid using methylene chloride as solvent.
  • the methylene chloride was distilled away.
  • the sulfonated product was neutralized with sodium methoxide in methanol and the methanol was evaporated to give alkyl benzene sulfonate, sodium salt mixture.
  • the product mixture contained methyl and di-methyl branching on the alkyl chain portion of the AB.
  • the phenyl group of the AB's was predominantly on the C2 carbon of the alkyl chain.
  • Olefin content The olefin content of the metathesis feed was derived from the total gas consumption during the exhaustive hydroformylation studies. The total olefinic content of the metathesis feed was greater than 90%. This is significantly higher than that of conventional olefinic feed which is about 50%.
  • Hydroformylation rate The hydroformylation rate was calculated from the initial pressure drop with time. While the intrinsic rate (i.e. the rate constant) of metathesis feed hydroformylation is slower than that of conventional olefinic feed hydroformylation, this is more than compensated for by the significantly higher olefin content of the metathesis feed. For both the C 9 /C 10 and the Cn/C ⁇ 2 fractions the metathesis feed exhibited a 25% faster apparent hydroformylation rate than the conventional olefininc feed while the hydroformylation rate of the metathesis feed Ci3/C 14 was a little slower than that of a similar conventional olefinic feed. The slower intrinsic hydroformylation rate of the metathesis feed is most probably due to the greater number of internal olefins. Significant double bond isomerisation thus has to take place before hydroformylation can take place at the terminal position.
  • Linearity and n:iso ratio The linearity and the n:iso ratio of the metathesis product was comparable to that of the conventional olefinic feed product.
  • the supposed greater number of internal double bonds in the metathesis feed did not negatively affect the linearity of the alcohol product as hydroformylation at the terminal double-bond is favoured above internal double bond hydroformylation.
  • C16 Fischer-Tropsch internal olefins were obtained by metathesis and were useable as a drilling fluid composition.
  • the drilling fluid composition included about 75% internal linear olefins and about 25% internal branched olefins, which internal branched olefins were predominantly mono-methyl, di-methyl and ethyl branched.
  • the drilling fluid compositions in accordance with the invention had the following physical properties:
  • Examples of the internal olefins useful as drilling fluids include:
  • a drilling fluid including: A linear component making up about 75.1 % of the composition;
  • a mono-methyl branched component making up about 24.9% of the drilling fluid composition.
  • a drilling fluid composition including: A linear component of mainly hexadec-3-ene in amounts of between 2 and 40%, depending on process conditions; and
  • a mono-methyl branched component of between 60% and 98% of the drilling fluid composition is provided.
  • MASS PRODUCT (g) 28055 mol me-hexenes + n-heptenes in 290 mol me-hexenes + n-heptenes out 026 heptene conversion 9106 mol C10 - 14 formed 094 mol % yield 6518 selectivity (%) 7158 TABLE 2: Mass and component balance of the batch reaction acetonitrile washed .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne des oxo-alcools, et des compositions de liquide de forage dérivées d'hydrocarbures dérivés par métathèse d'hydrocarbures Fischer-Tropsch.
EP00952774A 1999-07-06 2000-07-06 Utilisation de produits issus de la metathese de produits de traitement fischer-tropsch Withdrawn EP1198442A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US14238199P 1999-07-06 1999-07-06
ZA994377 1999-07-06
ZA9904377 1999-07-06
US142381P 1999-07-06
PCT/ZA2000/000123 WO2001002328A1 (fr) 1999-07-06 2000-07-06 Utilisation de produits issus de la metathese de produits de traitement fischer-tropsch

Publications (1)

Publication Number Publication Date
EP1198442A1 true EP1198442A1 (fr) 2002-04-24

Family

ID=26840054

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00952774A Withdrawn EP1198442A1 (fr) 1999-07-06 2000-07-06 Utilisation de produits issus de la metathese de produits de traitement fischer-tropsch

Country Status (7)

Country Link
EP (1) EP1198442A1 (fr)
JP (1) JP2003527315A (fr)
CN (1) CN1402698A (fr)
AU (1) AU6541500A (fr)
BR (1) BR0012225A (fr)
CA (1) CA2376603A1 (fr)
WO (1) WO2001002328A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10305562A1 (de) * 2003-02-10 2004-08-26 Sasol Germany Gmbh Estermischungen auf Basis verzweigter Alkohole und/oder verzweigter Säuren und deren Verwendung als Polymeradditiv
US8524965B2 (en) 2005-12-21 2013-09-03 Chevron Oronite Company Llc Method of making an alkylated aromatic using acidic ionic liquid catalyst

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5116618A (en) * 1974-07-31 1976-02-10 Nissan Chemical Ind Ltd Arukirubenzenno seizohoho
US4544792A (en) * 1984-12-13 1985-10-01 Mobil Oil Corporation Upgrading Fischer-Tropsch olefins
EP0276096A1 (fr) * 1987-01-21 1988-07-27 Mobil Oil Corporation Procédé de métathèse d'oléfine
WO1994012589A1 (fr) * 1991-07-27 1994-06-09 Oilfield Chemical Technology Limited Boue de forage
GB2258258B (en) * 1991-07-27 1995-04-19 David Brankling Drilling fluid
GB9216014D0 (en) * 1992-07-28 1992-09-09 British Petroleum Co Plc Lubricating oils
EG22088A (en) * 1996-04-16 2002-07-31 Procter & Gamble Alkoxylated sulfates
MA24137A1 (fr) * 1996-04-16 1997-12-31 Procter & Gamble Fabrication d'agents de surface ramifies .
FR2789072B1 (fr) * 1999-01-29 2001-04-13 Inst Francais Du Petrole Procede de metathese des olefines en presence d'un agent stabilisant du catalyseur

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0102328A1 *

Also Published As

Publication number Publication date
AU6541500A (en) 2001-01-22
JP2003527315A (ja) 2003-09-16
CA2376603A1 (fr) 2001-01-11
CN1402698A (zh) 2003-03-12
BR0012225A (pt) 2002-03-26
WO2001002328A1 (fr) 2001-01-11

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