US2133282A - Preparation of alkylated aromatic sulphonic acids - Google Patents
Preparation of alkylated aromatic sulphonic acids Download PDFInfo
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- US2133282A US2133282A US59548A US5954836A US2133282A US 2133282 A US2133282 A US 2133282A US 59548 A US59548 A US 59548A US 5954836 A US5954836 A US 5954836A US 2133282 A US2133282 A US 2133282A
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- US
- United States
- Prior art keywords
- sulphonic acids
- naphthalene
- temperature
- sulphuric acid
- acid
- 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 - Lifetime
Links
- 239000002253 acid Substances 0.000 title description 8
- 150000007513 acids Chemical class 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 4
- 125000003118 aryl group Chemical group 0.000 title 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 239000001117 sulphuric acid Substances 0.000 description 15
- 235000011149 sulphuric acid Nutrition 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 9
- 150000001491 aromatic compounds Chemical class 0.000 description 6
- -1 hexyl alcohols Chemical class 0.000 description 6
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical group CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 230000000149 penetrating effect Effects 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 238000010000 carbonizing Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 230000006208 butylation Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QNVRIHYSUZMSGM-UHFFFAOYSA-N n-butyl methyl carbinol Natural products CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/33—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems
- C07C309/34—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems formed by two rings
- C07C309/35—Naphthalene sulfonic acids
- C07C309/36—Naphthalene sulfonic acids substituted by alkyl groups
- C07C309/37—Naphthalene sulfonic acids substituted by alkyl groups by alkyl groups containing at least three carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/03—Organic sulfoxy compound containing
Definitions
- Patented 18, 1938 UNITED STATES PATENT OFFICE PREPARATION OF ALKYLATED AROMATIC SULPHONIC ACIDS of New York No Drawing. Application January 17, 1936, Serial No. 59,548
- the present invention relates to a process for preparing alkylated naphthalene sulphonic acids and their salts and it particularly relates to a process of preparing novel alkylated naphthalene sulphonic acids and compositions thereof containing between 4 to 8 carbon atoms in the alkyl group.
- the present invention will be illustratively described in connection with the production of mono-alkyl, alpha naphthalene sulphonic acids although it is to be understood that the present invention is also applicable to the production of other alkylated sulphonic acids than those specifically described.
- a further'object of the present invention is to prepare improved alkylated naphthalene sulphonic acids and their salts which may be directly utilized as penetrating and wetting out agents without requiring an expensive and diiiicultpurification process and which preparations may be readily shipped, stored and utilized.
- naphthalene may be successfully alkylated and sulphonated with high yields and may be maintained between 90 to 130 C. with a preferred range between 100 to 120 C. and for a time range of from 1 to hours, with a preferred range of from 2 to 3 hours.
- the tem- 5 perature is preferably maintained well below 70 C. with a preferred range of 40 to 50 C. and for a. relatively long time say for more than hours and preferably for less than 20'to 25 hours.
- naphthalene and secondary butyl carbinol in equimolecular portions are combined together in the presence of a large excess of concentrated sulphuric acid at a temperature of 100 to 120 .C. for a time of approximately 1 to 3 hours.
- naphthalene and 88 parts of secondary butyl carbinol are mixed together and 385 parts of 66 B. sulphuric acid are added.
- the mixture is gradually heated until the temperature reaches 100 C.
- the mixture When the reaction has been completed the mixture will separate into two layers, the upper layer containing the products of condensation and the lower layer containing a residual acid, which lower layer is drawn oil as waste acid.
- the top layer containing the amylated naphthalene is then treated with a mixture of 66 B. sulphuric acid and 20% oleum, the mixture for example being made of 100 parts of sulphuric acid and 100 parts of the oleum.
- Sulphonation is carried ,out from 16 to 18 hours at a temperature of from 40 to C.
- the resultant sulphonated product is then di- 50 luted with water, say about three times its own volume, and the diluted mixture is treated with parts of freshly sl'aked lime, which will be about sufficient to neutralize the free sulphuric acid.
- the solution is particularly suitable for carbonizing' since it is highly resistant to'5 Tw. sulphuric acid (about 4% by weight) which acid is largely used for carbonizing.
- the compound has a highresistance to calcium chloride and it will stand up to 2 parts of calcium chloride to 1 part of the sulphonic acid.
- alcohols or mixtures of alcohols may be utilized such as normal butyl alcohol, iso-butyl alcohol, secondary butyl alcohol, normal butyl carbinol, (or normal amyl'alcohol) iso-butyl carbinol, methyl propyl carbinol, diethyl carbinol, dimethyl ethyl carbinol, tertiary amyl alcohol, normal hexyl'alcohol, methyl amyl alcohol, 2- ethyl butyl alcohol and octyl alcohol, (2-ethyl hexanol)
- the octyl and hexyl alcohols require a somewhat higher proportion of sulphuric acid than the secondary butyl carbinol in the alkylation step.
- the beta product forms between 5 to 20% of the sulphonic acid while the alpha ranges from to 80% of the sulphonic acid.
- sulphonation and/or allgvlation operations described above may, in certain instances, be also applied to alkylation with less than four, or more than eight carbon atoms and/or to the treatment of other cyclic hydrocarbons or heterocyclic materials than naphthalene, such as cyclohexane, pyridine, quinolin, benzene, toluene, xylene, anthracene, phenanthrene, terpenes, (e. g.
- a process of successively butylating and sulphonating aromatic compounds which comprises butylating the aromatic compounds with a butyl alcohol and with a sulphonating agent successively at decreasing temperatures, the butylation being carried out at a temperature of 90 to 130 C. and the sulphonation being carried out at a temperature of between 30 and 60 C.
- a process of successively amylating and sulphonating aromatic compounds which comprises amylating aromatic compounds with an amyl alcohol and with a sulphonating agent successively at decreasing temperatures, the amylation being carried out at a temperature of 90 to 130 C. and the sulphonation being carried out at a temperature of between 30 and 60 C.
- a process of successively alkylating and sulphonating aromatic compounds which comprises treating the aromatic compounds with an alkylating agent and with a sulphonating agent successively at decreasing temperatures, the alkylation being carried out ata temperature of 90 to 130 C. and the sulphonation being carried out at a temperature of between 30 and 60 0., the alkylating agent consisting of one or more aliphatic alcohols having from 4 to 8 carbon atoms.
- a process of producing mono alkyl alphanaphthalene sulphonic acids which comprises combining naphthalene and an aliphatic alcohol in the presence of sulphuric acid at a temperature of to C. and then increasing the con- I centration of sulphuric acid and sulphonating at a temperature of 40 to 50 C.
- a process of producing mono alkyl alphanaphthalene sulphonic acids which comprises combining naphthalene and an aliphatic alcohol in the presence of sulphuric acid at a tempera ture of 100 to 120 C. and then increasing the concentration of sulphuric acid and sulphonating at a temperature of 40 to 50 0., said aliphatic alcohol containingfrom 4 to 8 carbon atoms.
- I V 6 A process of producing mono alkyl alphanaphthalene sulphonic acids which comprises combining naphthalene and an aliphatic alcohol in the presence of sulphuric acid at a temperature of 100 to 120 C. and then increasing the concentration of sulphuric acid and sulphonating at a temperature of 40 to 50 C., said naphthalene 1 and aliphatic alcohol being used in equi-molecular proportions.
- a process of producing mono alkyl alpha naphthalene sulphonic acid which comprises reacting about equimolecular weights of naphthalene and a lower alkanol having between 4 and 8 carbon atoms together in the presence of sulphuric acid at a temperature between 100 and 120 C. and then reacting the alkylated naphthalene witha sulphonating reagent containing oleum at a temperature between 40 and 50 C. to form the alpha-sulphonic acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented 18, 1938 UNITED STATES PATENT OFFICE PREPARATION OF ALKYLATED AROMATIC SULPHONIC ACIDS of New York No Drawing. Application January 17, 1936, Serial No. 59,548
. 7 Claims.
The present invention relates to a process for preparing alkylated naphthalene sulphonic acids and their salts and it particularly relates to a process of preparing novel alkylated naphthalene sulphonic acids and compositions thereof containing between 4 to 8 carbon atoms in the alkyl group.
Although not specifically limited thereto, the present invention will be illustratively described in connection with the production of mono-alkyl, alpha naphthalene sulphonic acids although it is to be understood that the present invention is also applicable to the production of other alkylated sulphonic acids than those specifically described.
It is among the objects of the present invention to provide an improved process for preparing alkylated naphthalene sulphonic acids and their compounds for use as penetrating and wetting out agents and which will be of high stability and substantial resistance to acids, and calcium and magnesium salts.
It is another object of the present invention to prepare alkylated naphthalene sulphonic acids and their compoundswith high yield and without the production of undesirable Icy-products which acids are particularly useful incarbonizing', in dye baths, in bleaching operations and for inclusion for soaping, scouring and detergent mixtures.
A further'object of the present invention is to prepare improved alkylated naphthalene sulphonic acids and their salts which may be directly utilized as penetrating and wetting out agents without requiring an expensive and diiiicultpurification process and which preparations may be readily shipped, stored and utilized.
' Other objects will be obvious and will appear during the course of the present specification.
In accomplishing the above objects it has been found that naphthalene may be successfully alkylated and sulphonated with high yields and may be maintained between 90 to 130 C. with a preferred range between 100 to 120 C. and for a time range of from 1 to hours, with a preferred range of from 2 to 3 hours.
In the second sulphonation operation, the tem- 5 perature is preferably maintained well below 70 C. with a preferred range of 40 to 50 C. and for a. relatively long time say for more than hours and preferably for less than 20'to 25 hours.
In the second operation it is most desirable to 0 utilize a mixture of concentrated sulphuric acid and oleum .which will assure substitution of a sulphonic acid group in the naphthalene nucleus.
It appears as a result of the above process that only one alkyl group enters the nucleus. The exact position of this alhl group has not been definitely determined.
It also appears as a result of the above process, that a small amount of the beta acid is formed and this has been found particularly advantageous inasmuch as a combination of a relatively large amount of the alpha with a relatively small amount of the beta acid is most stable and effective.
As an example of one method of carrying out the invention, naphthalene and secondary butyl carbinol in equimolecular portions are combined together in the presence of a large excess of concentrated sulphuric acid at a temperature of 100 to 120 .C. for a time of approximately 1 to 3 hours.
For example, 130 parts by weight of naphthalene and 88 parts of secondary butyl carbinol are mixed together and 385 parts of 66 B. sulphuric acid are added.
The mixture is gradually heated until the temperature reaches 100 C.
When the reaction has been completed the mixture will separate into two layers, the upper layer containing the products of condensation and the lower layer containing a residual acid, which lower layer is drawn oil as waste acid.
The top layer containing the amylated naphthalene is then treated with a mixture of 66 B. sulphuric acid and 20% oleum, the mixture for example being made of 100 parts of sulphuric acid and 100 parts of the oleum.
Sulphonation is carried ,out from 16 to 18 hours at a temperature of from 40 to C.
The resultant sulphonated product is then di- 50 luted with water, say about three times its own volume, and the diluted mixture is treated with parts of freshly sl'aked lime, which will be about sufficient to neutralize the free sulphuric acid. a
penetrative properties and will give a test result of 2 to 3 seconds with a standard sinking test on felt using a 1% solution at F.
The solution is particularly suitable for carbonizing' since it is highly resistant to'5 Tw. sulphuric acid (about 4% by weight) which acid is largely used for carbonizing.
Even after heating at 150-180 F. for several hours there' is no clouding or precipitation.
The compound has a highresistance to calcium chloride and it will stand up to 2 parts of calcium chloride to 1 part of the sulphonic acid.
Other alcohols or mixtures of alcohols may be utilized such as normal butyl alcohol, iso-butyl alcohol, secondary butyl alcohol, normal butyl carbinol, (or normal amyl'alcohol) iso-butyl carbinol, methyl propyl carbinol, diethyl carbinol, dimethyl ethyl carbinol, tertiary amyl alcohol, normal hexyl'alcohol, methyl amyl alcohol, 2- ethyl butyl alcohol and octyl alcohol, (2-ethyl hexanol) The octyl and hexyl alcohols require a somewhat higher proportion of sulphuric acid than the secondary butyl carbinol in the alkylation step.
In the preferred product the beta product forms between 5 to 20% of the sulphonic acid while the alpha ranges from to 80% of the sulphonic acid.
The above process may be illustrated by the following equations:
The sulphonation and/or allgvlation operations described above may, in certain instances, be also applied to alkylation with less than four, or more than eight carbon atoms and/or to the treatment of other cyclic hydrocarbons or heterocyclic materials than naphthalene, such as cyclohexane, pyridine, quinolin, benzene, toluene, xylene, anthracene, phenanthrene, terpenes, (e. g.
pine oil) and so forth, which hydrocarbons may T aisaaea V be made in the preparations, times and temperatures specified above and that the process, as described, may also be described for the sulphonation of other products and it is intended to include all such changes and modifications within the scope of the present invention.
What is claimed is:
1. A process of successively butylating and sulphonating aromatic compounds which comprises butylating the aromatic compounds with a butyl alcohol and with a sulphonating agent successively at decreasing temperatures, the butylation being carried out at a temperature of 90 to 130 C. and the sulphonation being carried out at a temperature of between 30 and 60 C.
2. A process of successively amylating and sulphonating aromatic compounds which comprises amylating aromatic compounds with an amyl alcohol and with a sulphonating agent successively at decreasing temperatures, the amylation being carried out at a temperature of 90 to 130 C. and the sulphonation being carried out at a temperature of between 30 and 60 C.
3. A process of successively alkylating and sulphonating aromatic compounds which comprises treating the aromatic compounds with an alkylating agent and with a sulphonating agent successively at decreasing temperatures, the alkylation being carried out ata temperature of 90 to 130 C. and the sulphonation being carried out at a temperature of between 30 and 60 0., the alkylating agent consisting of one or more aliphatic alcohols having from 4 to 8 carbon atoms.
4. A process of producing mono alkyl alphanaphthalene sulphonic acids which comprises combining naphthalene and an aliphatic alcohol in the presence of sulphuric acid at a temperature of to C. and then increasing the con- I centration of sulphuric acid and sulphonating at a temperature of 40 to 50 C.
5. A process of producing mono alkyl alphanaphthalene sulphonic acids which comprises combining naphthalene and an aliphatic alcohol in the presence of sulphuric acid at a tempera ture of 100 to 120 C. and then increasing the concentration of sulphuric acid and sulphonating at a temperature of 40 to 50 0., said aliphatic alcohol containingfrom 4 to 8 carbon atoms. I V 6. A process of producing mono alkyl alphanaphthalene sulphonic acids which comprises combining naphthalene and an aliphatic alcohol in the presence of sulphuric acid at a temperature of 100 to 120 C. and then increasing the concentration of sulphuric acid and sulphonating at a temperature of 40 to 50 C., said naphthalene 1 and aliphatic alcohol being used in equi-molecular proportions.
7. A process of producing mono alkyl alpha naphthalene sulphonic acid which comprises reacting about equimolecular weights of naphthalene and a lower alkanol having between 4 and 8 carbon atoms together in the presence of sulphuric acid at a temperature between 100 and 120 C. and then reacting the alkylated naphthalene witha sulphonating reagent containing oleum at a temperature between 40 and 50 C. to form the alpha-sulphonic acid.
ALTON A. COO
SWANEE V. VALJAVEC.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59548A US2133282A (en) | 1936-01-17 | 1936-01-17 | Preparation of alkylated aromatic sulphonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59548A US2133282A (en) | 1936-01-17 | 1936-01-17 | Preparation of alkylated aromatic sulphonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2133282A true US2133282A (en) | 1938-10-18 |
Family
ID=22023682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US59548A Expired - Lifetime US2133282A (en) | 1936-01-17 | 1936-01-17 | Preparation of alkylated aromatic sulphonic acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2133282A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573675A (en) * | 1948-02-28 | 1951-11-06 | Universal Oil Prod Co | Process for the sulfonation of alkyl aromatic hydrocarbons |
| US2820015A (en) * | 1949-11-25 | 1958-01-14 | Phillips Petroleum Co | Method for production of alkaryl sulfonate detergent compositions |
| US3167517A (en) * | 1960-08-11 | 1965-01-26 | American Cyanamid Co | Dyeing assistant and leveling compositions |
| US3377130A (en) * | 1960-08-11 | 1968-04-09 | American Cyanamid Co | Dyed nitrogenous fibers and anionic dye composition therefor |
| WO1992022524A1 (en) * | 1991-06-18 | 1992-12-23 | Henkel Corporation | Process for making alkyl naphthalene sulfonate surfactants |
-
1936
- 1936-01-17 US US59548A patent/US2133282A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573675A (en) * | 1948-02-28 | 1951-11-06 | Universal Oil Prod Co | Process for the sulfonation of alkyl aromatic hydrocarbons |
| US2820015A (en) * | 1949-11-25 | 1958-01-14 | Phillips Petroleum Co | Method for production of alkaryl sulfonate detergent compositions |
| US3167517A (en) * | 1960-08-11 | 1965-01-26 | American Cyanamid Co | Dyeing assistant and leveling compositions |
| US3377130A (en) * | 1960-08-11 | 1968-04-09 | American Cyanamid Co | Dyed nitrogenous fibers and anionic dye composition therefor |
| WO1992022524A1 (en) * | 1991-06-18 | 1992-12-23 | Henkel Corporation | Process for making alkyl naphthalene sulfonate surfactants |
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