US20040210083A1 - Process for production of essentially chloride-free calcium sulfonate - Google Patents

Process for production of essentially chloride-free calcium sulfonate Download PDF

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Publication number
US20040210083A1
US20040210083A1 US10/417,788 US41778803A US2004210083A1 US 20040210083 A1 US20040210083 A1 US 20040210083A1 US 41778803 A US41778803 A US 41778803A US 2004210083 A1 US2004210083 A1 US 2004210083A1
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US
United States
Prior art keywords
sulfonic acid
mol
calcium hydroxide
reaction mixture
solvent
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.)
Abandoned
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US10/417,788
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English (en)
Inventor
Abraham De Kraker
Steven Holmes
Krishna Kaushik
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Shell USA Inc
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Individual
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 Individual filed Critical Individual
Priority to US10/417,788 priority Critical patent/US20040210083A1/en
Assigned to SHELL OIL COMPANY reassignment SHELL OIL COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HOLMES, STEVEN ALLEN, DE KRAKER, ABRAHAM ROBERT, KAUSHIK, KRISHNA RANGRAJ
Priority to PCT/US2004/011684 priority patent/WO2004094366A1/en
Priority to JP2006510090A priority patent/JP5000295B2/ja
Priority to US10/824,785 priority patent/US7094922B2/en
Priority to MXPA05011000A priority patent/MXPA05011000A/es
Priority to CN200480010183XA priority patent/CN1774416B/zh
Priority to EP04759891A priority patent/EP1631541A1/en
Priority to CA002522355A priority patent/CA2522355A1/en
Priority to AU2004232952A priority patent/AU2004232952B2/en
Publication of US20040210083A1 publication Critical patent/US20040210083A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/04—Detergent property or dispersant property
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions

Definitions

  • the invention relates to a process for the production of low base number essentially chloride-free calcium sulfonate.
  • Low base number calcium sulfonates are generally produced by the reaction of sulfonic acid with calcium hydroxide or calcium oxide, utilizing a promoter such as an alkanol. They can also be produced from sodium sulfonate by the use of calcium hydroxide or oxide and calcium chloride. Such sulfonates may be used as highly valued additives for lubricating oils such as passenger car, diesel, and marine engine lubricants. They may be further processed into overbased sulfonates, which have higher base numbers and are also used as additives for specialty lubricating oils.
  • U.S. Pat. No. 5,804,094 teaches a method of producing a low base number calcium sulfonate of greater than 500 molecular weight using carboxylic acid and a high base number calcium sulfonate.
  • U.S. Pat. No. 5,789,615 teaches the use of staged addition of calcium hydroxide to sulfonic acid to produce a low viscosity, low haze product without the use of promoters, especially without the use of chloride.
  • the calcium hydroxide is added in two or more steps, with 30-180 minutes heat soak after each step.
  • U.S. Pat. No. 4,615,841 describes a method of producing calcium sulfonates in the presence of an alkanol.
  • U.S. Pat. No. 4,279,837 teaches the preparation of alkaline earth metal salts of alkyl benzene sulfonic acids by neutralization of the acid using an oxyalkylate as a promoter, thus also producing a chloride free calcium sulfonate.
  • U.S. Pat. No. 3,719,596 describes a method of producing calcium sulfonate in which the reaction mixture is made acidic and then basic again using an alkanolamine.
  • U.S. Pat. No. 2,779,784 teaches a method of producing calcium sulfonate in which sulfonic acid is neutralized with calcium hydroxide at 220° F. to 390° F. (104° C. to 199° C.), in the presence of 1 ⁇ 2 to 10 parts water per part calcium hydroxide. This would correspond to between 0.12 and 2.4 mol water per mol calcium hydroxide.
  • a method has been discovered to produce low base number calcium sulfonate, which is essentially free of residual chlorine and easily concentrated.
  • the method can also produce a low viscosity product.
  • the method may also be practiced in a continuous manner.
  • the present invention relates to a process for the production of calcium sulfonate which comprises preparing sulfonic acid solution by adding about 1 to about 20 volumes of a miscible solvent to sulfonic acid and removing dissolved or entrained SO 2 or SO 3 if present, mixing the resultant sulfonic acid solution with about 1 to about 5 moles of water per mol of sulfonic acid and about 1 to about 10 moles of calcium hydroxide per mole of sulfonic acid to prepare a reaction mixture, heating the reaction mixture to between about 40° C. and about 200° C. for a period of time up to about 60 minutes with stirring, separating excess calcium hydroxide and calcium salts of mineral acid from such a reaction mixture, and recovering solvent and oil to make a final essentially chloride-free calcium sulfonate product.
  • FIG. 1 This figure shows a flow chart of a continuous process for producing calcium sulfonate.
  • FIG. 2 This figure shows the relationship between the Strong Base Number (SBNC) of the calcium sulfonate solution produced by the invention and the SBNC of the product after solvent stripping.
  • SBNC Strong Base Number
  • FIG. 3 This figure shows the relationship between product viscosity and the SBNC of the product after solvent stripping.
  • the present invention provides a process for the production of low base number essentially chloride-free calcium sulfonate.
  • a low base number calcium sulfonate has a base number of 0 to about 50.
  • essentially chloride-free is meant a maximum chlorine content of 1000 ppm.
  • Sulfonic acid in an oil/solvent solution or dispersion is neutralized by calcium hydroxide in the presence of a specific amount of water. Excess hydroxide and inorganic salt are subsequently removed from the reaction mixture by a suitable means such as centrifugation or filtration before removal of the solvent. After removal of the solvent, the calcium sulfonate in oil is concentrated by suitable means such as vacuum flashing or vacuum distillation, to produce a final product with a base number between 0 and about 50, and the desired final concentration.
  • the sulfonic acid utilized may be derived from petroleum oil.
  • the oil used in the process can be any suitably refined crude distillate.
  • An example of a suitable feedstock is a vacuum distillate of appropriate molecular weight that has been refined by solvent extraction and/or hydrotreating to reduce the polynuclear aromatics content.
  • the sulfonic acid solution used in the process is created by reacting the refined crude distillate with fuming sulfuric acid (about 27%—about 33% SO 3 ; oleum) or gaseous SO 3 .
  • fuming sulfuric acid about 27%—about 33% SO 3 ; oleum
  • gaseous SO 3 gaseous SO 3
  • the polysulfonic acid plus SO 3 depleted sulfuric acid form a sludge.
  • This reaction mixture is diluted with about 1 to about 20 volumes of a miscible solvent to reduce viscosity, and the sludge is separated out by gravity settling, leaving the sulfonic acid in a solvent/oil solution.
  • Dissolved or entrained SO 3 and/or SO 2 produced as a byproduct of side reactions between the oil and the SO 3 , are removed from the solution if present.
  • One method of removal is stripping with nitrogen or another inert gas.
  • the solution can also be centrifuged to remove traces of sludge prior to removal of dissolved or entrained SO 2 or SO 3 .
  • Suitable solvents include any C 3 to C 10 alkane, toluene or any low viscosity, miscible solvent. Most preferred is heptane or commercially available mixtures of heptane isomers.
  • the reaction mixture is heated with stirring to a temperature of from about 40° C. to about 200° C., preferably from about 80° C. to about 120° C.
  • the mixture is preferably stirred for a period of time up to about 60 minutes, more preferably up to about 30 minutes.
  • the resulting mixture is then separated to remove excess calcium hydroxide and any salts formed from residual sludge or SO 2 .
  • One method of separating the mixture is centrifugation. Centrifugation should be performed for a sufficient amount of time to remove the excess calcium hydroxide and any salts. This period of time can be any such sufficient amount of time, for example, 20 minutes.
  • the presence of the solvent greatly improves the speed of separation.
  • the solvent is recovered from the clear centrate for recycle by any convenient means such as a solvent stripper.
  • the product may be further concentrated via distillation or vacuum flashing to remove a portion or all of the unreacted oil.
  • This process may be operated in a continuous fashion in a manner such as that shown in FIG. 1.
  • Sulfonic acid 1 is added to a reactor 7 , followed by water 3 and lime 5 .
  • the resultant mixture then undergoes separation 9 , with the lime and water being removed.
  • the next step is solvent recovery 11 , followed by concentration 13 to produce the calcium sulfonate in base oil 15 .
  • a base number of up to 3.2 can be obtained by optimizing the amount of TBA, water, and temperature.
  • Table IV shows the resulting Strong Base Number (SBNC, measured according to ASTM D974, incorporated by reference) of the centrate for various values of water content measured in mol/mol of sulfonic acid, lime content measured in mol/mol of sulfonic acid, reaction temperature measured in ° C., and reaction time and centrifugation time measured in minutes.
  • FIG. 2 shows the correlation between the SBNC of the centrate and the concentrated product.
  • FIG. 2 shows that a base number of 3.6 correlates to a stripped centrate SBNC of about 9.1.
  • FIG. 3 shows the relationship between the base number of the stripped product of the invention and the viscosity of the product. From Table VI and FIG. 3 it can be seen that a viscosity of about 15 cSt at 100° C. correlates to a stripped centrate SBNC of about 9.1. TABLE VI Relationship between SBNC of Stripped Product and Viscosity of Stripped Product Stripped Centrate Stripped Centrate SBNC Viscosity/100° C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
US10/417,788 2003-04-17 2003-04-17 Process for production of essentially chloride-free calcium sulfonate Abandoned US20040210083A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US10/417,788 US20040210083A1 (en) 2003-04-17 2003-04-17 Process for production of essentially chloride-free calcium sulfonate
AU2004232952A AU2004232952B2 (en) 2003-04-17 2004-04-15 Process for production of essentially chloride-free calcium sulfonate
MXPA05011000A MXPA05011000A (es) 2003-04-17 2004-04-15 Proceso para la produccion de sulfonato de calcio esencialmente libre de cloruros.
JP2006510090A JP5000295B2 (ja) 2003-04-17 2004-04-15 本質的に塩化物を含まないスルホン酸カルシウムの製造方法
US10/824,785 US7094922B2 (en) 2003-04-17 2004-04-15 Process for production of essentially chloride-free calcium sulfonate
PCT/US2004/011684 WO2004094366A1 (en) 2003-04-17 2004-04-15 Process for production of essentially chloride-free calcium sulfonate
CN200480010183XA CN1774416B (zh) 2003-04-17 2004-04-15 制备基本上不含氯化物的磺酸钙的方法
EP04759891A EP1631541A1 (en) 2003-04-17 2004-04-15 Process for production of essentially chloride-free calcium sulfonate
CA002522355A CA2522355A1 (en) 2003-04-17 2004-04-15 Process for production of essentially chloride-free calcium sulfonate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10/417,788 US20040210083A1 (en) 2003-04-17 2003-04-17 Process for production of essentially chloride-free calcium sulfonate

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/824,785 Continuation-In-Part US7094922B2 (en) 2003-04-17 2004-04-15 Process for production of essentially chloride-free calcium sulfonate

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US10/417,788 Abandoned US20040210083A1 (en) 2003-04-17 2003-04-17 Process for production of essentially chloride-free calcium sulfonate
US10/824,785 Expired - Fee Related US7094922B2 (en) 2003-04-17 2004-04-15 Process for production of essentially chloride-free calcium sulfonate

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US (2) US20040210083A1 (zh)
EP (1) EP1631541A1 (zh)
JP (1) JP5000295B2 (zh)
CN (1) CN1774416B (zh)
AU (1) AU2004232952B2 (zh)
CA (1) CA2522355A1 (zh)
MX (1) MXPA05011000A (zh)
WO (1) WO2004094366A1 (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108218746A (zh) * 2018-04-04 2018-06-29 江苏丰益化工科技有限公司 一种高纯度高级醇硫酸盐的生产系统

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101602696B (zh) * 2009-05-26 2010-12-01 锦州康泰润滑油添加剂有限公司 一种低碱值磺酸钙盐的制备方法
US11473032B2 (en) 2010-02-02 2022-10-18 Fuchs Petrolub Se Constant velocity joint having a boot

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US2266325A (en) * 1938-02-21 1941-12-16 Tide Water Associated Oil Comp Lubricating composition and process of preparing same
US2402325A (en) * 1943-08-19 1946-06-18 Atlantic Refining Co Oil solutions of basic alkaline earth metal sulphonates and method of making same
US2418894A (en) * 1944-12-09 1947-04-15 Standard Oil Dev Co Compounded lubricating oil
US2779784A (en) * 1954-05-13 1957-01-29 Continental Oil Co Basic alkaline earth metal sulfonates and method of making same
US2846466A (en) * 1954-12-29 1958-08-05 Pure Oil Co Manufacture of basic petroleum sulfonate salts using two-step neutralization in non-aqueous phase
US2884445A (en) * 1956-12-17 1959-04-28 Phillips Petroleum Co Metal petroleum sulfonates
US2909563A (en) * 1955-09-06 1959-10-20 Phillips Petroleum Co Production of petroleum sulfonates
US2915517A (en) * 1957-05-08 1959-12-01 Lubrizol Corp Oil-soluble metal sulfonates and process for the preparation thereof
US3007868A (en) * 1959-05-19 1961-11-07 Gulf Oil Corp Light-color, oil-soluble alkaline earth metal sulfonates
US3023231A (en) * 1958-11-28 1962-02-27 Phillips Petroleum Co Production of calcium petroleum sulfonates
US3260670A (en) * 1962-11-29 1966-07-12 Standard Oil Co Alkaline metal sulfonates
US3719596A (en) * 1970-08-05 1973-03-06 Richardson Co Preparation of alkaline-earth alkylbenzene sulfonates
US4279837A (en) * 1979-03-02 1981-07-21 Hoechst Aktiengesellschaft Process for the preparation of alkaline earth metal salts of alkyl benzenesulfonic acids
US4615841A (en) * 1983-09-22 1986-10-07 Dresser Industries, Inc. Process for making alkaline-earth metal salts of alkaryl sulfonic acids
US5578235A (en) * 1990-12-31 1996-11-26 Ethyl Additives Corporation Overbased calcium sulfonate
US5789615A (en) * 1992-08-14 1998-08-04 Exxon Chemical Patents, Inc. Process for the preparation of sulphonates
US5804094A (en) * 1995-02-28 1998-09-08 Exxon Chemical Patents, Inc. Low base number sulphonates

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GB709587A (en) 1951-01-29 1954-05-26 Bataafsche Petroleum Lubricating oil compositions
US3367865A (en) 1961-05-19 1968-02-06 Exxon Research Engineering Co Oil-soluble metal sulfonates and lubricants containing them
FR1498638A (fr) 1966-09-08 1967-10-20 Exxon Standard Sa Procédé de préparation de sulfonates alcalino-terreux à partir d'acides sulfoniques à chaînes paliphatiques peu ramifiées
SU1002287A1 (ru) 1981-06-30 1983-03-07 Предприятие П/Я В-2287 Способ получени нейтрального алкилбензолсульфоната кальци
SU1002288A1 (ru) 1981-06-30 1983-03-07 Предприятие П/Я В-2287 Способ получени алкилбензолсульфоната кальци
CA2020509C (en) 1989-08-10 1998-04-28 William K. Reagen Chromium compounds and uses thereof

Patent Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2266325A (en) * 1938-02-21 1941-12-16 Tide Water Associated Oil Comp Lubricating composition and process of preparing same
US2402325A (en) * 1943-08-19 1946-06-18 Atlantic Refining Co Oil solutions of basic alkaline earth metal sulphonates and method of making same
US2418894A (en) * 1944-12-09 1947-04-15 Standard Oil Dev Co Compounded lubricating oil
US2779784A (en) * 1954-05-13 1957-01-29 Continental Oil Co Basic alkaline earth metal sulfonates and method of making same
US2846466A (en) * 1954-12-29 1958-08-05 Pure Oil Co Manufacture of basic petroleum sulfonate salts using two-step neutralization in non-aqueous phase
US2909563A (en) * 1955-09-06 1959-10-20 Phillips Petroleum Co Production of petroleum sulfonates
US2884445A (en) * 1956-12-17 1959-04-28 Phillips Petroleum Co Metal petroleum sulfonates
US2915517A (en) * 1957-05-08 1959-12-01 Lubrizol Corp Oil-soluble metal sulfonates and process for the preparation thereof
US3023231A (en) * 1958-11-28 1962-02-27 Phillips Petroleum Co Production of calcium petroleum sulfonates
US3007868A (en) * 1959-05-19 1961-11-07 Gulf Oil Corp Light-color, oil-soluble alkaline earth metal sulfonates
US3260670A (en) * 1962-11-29 1966-07-12 Standard Oil Co Alkaline metal sulfonates
US3719596A (en) * 1970-08-05 1973-03-06 Richardson Co Preparation of alkaline-earth alkylbenzene sulfonates
US4279837A (en) * 1979-03-02 1981-07-21 Hoechst Aktiengesellschaft Process for the preparation of alkaline earth metal salts of alkyl benzenesulfonic acids
US4615841A (en) * 1983-09-22 1986-10-07 Dresser Industries, Inc. Process for making alkaline-earth metal salts of alkaryl sulfonic acids
US5578235A (en) * 1990-12-31 1996-11-26 Ethyl Additives Corporation Overbased calcium sulfonate
US5789615A (en) * 1992-08-14 1998-08-04 Exxon Chemical Patents, Inc. Process for the preparation of sulphonates
US5804094A (en) * 1995-02-28 1998-09-08 Exxon Chemical Patents, Inc. Low base number sulphonates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108218746A (zh) * 2018-04-04 2018-06-29 江苏丰益化工科技有限公司 一种高纯度高级醇硫酸盐的生产系统

Also Published As

Publication number Publication date
WO2004094366A1 (en) 2004-11-04
MXPA05011000A (es) 2005-12-12
US7094922B2 (en) 2006-08-22
US20050004392A1 (en) 2005-01-06
JP5000295B2 (ja) 2012-08-15
CA2522355A1 (en) 2004-11-04
AU2004232952B2 (en) 2008-01-24
CN1774416B (zh) 2010-05-12
CN1774416A (zh) 2006-05-17
AU2004232952A1 (en) 2004-11-04
EP1631541A1 (en) 2006-03-08
JP2006523768A (ja) 2006-10-19

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