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    Us2481845 PDF

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    Heri Rustamaji
    Terpin hydrate is produced by the reaction of pinene with dilute acid, usually 25% was steam distilled turpentine, which is 80 to sulfuric acid, at temperatures of about 30 to 40deg 90% pinene. When 25 parts of by side reactions resulting in the formation of the sulfuric acid were replaced by 25 parts of dipentene and other products which decrease the 25% toluene sulfonic acid, the yield in 15 hours was 34% and in 30 hours 59

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    © All Rights Reserved
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    Us2481845 PDF

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    Heri Rustamaji
    37 views2 pages
    Terpin hydrate is produced by the reaction of pinene with dilute acid, usually 25% was steam distilled turpentine, which is 80 to sulfuric acid, at temperatures of about 30 to 40deg 90% pinene. When 25 parts of by side reactions resulting in the formation of the sulfuric acid were replaced by 25 parts of dipentene and other products which decrease the 25% toluene sulfonic acid, the yield in 15 hours was 34% and in 30 hours 59

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    Terpin hydrate is produced by the reaction of pinene with dilute acid, usually 25% was steam distilled turpentine, which is 80 to sulfuric acid, at temperatures of about 30 to 40deg 90% pinene. When 25 parts of by side reactions resulting in the formation of the sulfuric acid were replaced by 25 parts of dipentene and other products which decrease the 25% toluene sulfonic acid, the yield in 15 hours was 34% and in 30 hours 59

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    © All Rights Reserved
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    37 views2 pages

    Us2481845 PDF

    Uploaded by

    Heri Rustamaji
    Terpin hydrate is produced by the reaction of pinene with dilute acid, usually 25% was steam distilled turpentine, which is 80 to sulfuric acid, at temperatures of about 30 to 40deg 90% pinene. When 25 parts of by side reactions resulting in the formation of the sulfuric acid were replaced by 25 parts of dipentene and other products which decrease the 25% toluene sulfonic acid, the yield in 15 hours was 34% and in 30 hours 59

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    Patented Sept.

    13,, 1949

    2,481,845

    u.N;ITEo;s TATES PAT EN 1'


    2,481,845

    oFFICE

    '

    PROCESS FOR CONVERSION OF PlNENE _' f '


    ; I 4

    To TERPIN HYDRATE

    '

    _ A ; Robert Gardner King, Norwalk, Conn., assignor


    .to King Organic Chemicals, Incorporated, Nor; . ,

    walk, Conn., a corporation of Connecticutv


    No Drawing. Application November 14, 1944, ' '
    Serial No. 563,455

    '

    7 Claims. (Cl. 260631.5)

    This invention relates to improvements in the

    tainable through the use of reduced quantities

    production of terpin hydrate, and in particular,

    of toluene sulfonic acid and the use of a small

    to improvements in the process of producing


    amount of mahogany acids in the reaction are
    terpin hydrate by the reaction of pinene with
    shown in the following table, which gives the
    dilute aqueous acid.
    5 results of several runs for the production of
    Terpin hydrate is commonly produced by re
    terpin hydrate from pinene. The product treated
    acting pinene with dilute acid, usually 25%
    was steam distilled turpentine, which is 80 to
    sulfuric acid, at temperatures of about 30 to 40
    90% pinene. Yields are based on the turpentine
    C. 10 to 15% of toluene sulfonic acid is used to
    used. In the ?rst run, sulfuric acid alone was
    promote the rate of reaction. The reaction which, 10 used. It will be noted that at the end of 15 hours
    as commonly carried out requires substantial
    only 8.7% of terpin hydrate had been produced
    time, for example, 30 to 40 hours, is accompanied
    and in 30 hours only 33%. When 25 parts of
    by side reactions resulting in the formation of
    the sulfuric acid were replaced by 25 parts of
    dipentene and other products which decrease the
    25% toluene sulfonic acid, the yield in 15 hours
    yield.
    15 was 34% and in 30 hours 59.2%. When, in addi
    In accordance with the present invention, the
    tion, 2% of mahogany soap was included in the
    reaction is carried out in the presence of greatly
    reaction mixture, the yield in 15 hours was 45.3%
    reduced quantities of toluene sulfonic acid and
    and in 30 hours 67.4%. Similar results were
    advantageously in the presence of relatively small
    obtained using sulfuric acid and other low
    amounts of mahogany acids. The use of reduced 20 proportions of toluene sulfuric acid, as shown in
    quantities of toluene sulfonic acid, i. e., about
    the table. Quantities shown are parts by weight.
    2 to 5% based on the total aqueous material gives
    better yields than have heretofore been obtain
    able. The use of a relatively small proportion of

    Turpentine _______ __

    150

    150

    150

    150

    150

    150

    150

    25% sulfuric acid____

    500

    475

    476

    460

    460

    440

    440

    mahogany acids greatly increases the speed of 25

    acid ____________ ._
    Mahoganysoap____

    ___

    25
    ___

    25
    2

    4o
    0

    40
    4

    60
    0

    60
    4

    25% toluene sulfonic

    Temperature, 0___ 35-38 34e37 34-37 34-37 34-37 3437 34-37


    the reaction, such that the reaction is as complete
    15 hr. yield
    in about 15 hours as it is in 30 to 40 hours, and
    percent__ 8.7 34.0 45.3 49.0 57.4 17.0 64.3
    also results in an increased yield through the
    iggnyielgmdauu 33.0 59.2 67.4 68.7 75.4 47.0 73.3
    r.y1e
    promotion of the rate and efficiency of the main
    30hr. yieldxloo
    reaction Without corresponding promotion of the 30
    percent_____ 26.4 57.7 67.3 62.2 76.2 36.2 87.6
    rate of side reactions. While the use of mahoga
    The amount of mahogany soap which is used
    ny acids with the reduced proportions of toluene
    in carrying out the process may be varied over
    sulfonic acid is of particular advantage, its use
    a relatively wide range from a fraction of 1%,
    is of advantage where larger quantities of the
    toluene sulfonic acid are used, as in previous 35 based on the quantity of pinene treated to as

    practice, or even where no toluene sulfonic acid


    is used, e. g., where sulfuric acid alone is used.
    The mahogany acids may be used as acids, or
    in the form of the mahogany soaps which are
    the common form in which mahogany acids are 40

    handled. It will be noted that the reaction mix


    ture is acid, and in view of the fact that relatively
    small quantities of the mahogany acids are used,
    it is probable that the product is present in acid
    form whether added as such or in the form of
    a soap or other compound.
    The mahogany acids which are used are pro

    duced, usually as by-products, by the treatment


    of petroleum oils with strong sulfuric acid. They

    much as 10% or even more.

    There seems to be

    little advantage in using more than about 5%.


    but increased quantities do not seem to interfere
    with the production of the desired product.
    I claim:
    1. In the production of terpin hydrate by the
    treatment of pinene with dilute acid at tempera
    tures of about 30 to 40 C., the step of including
    in the reaction mixture a small quantity of
    mahogany acids as a reaction promoter.

    2. In the production of terpin hydrate by the


    treatment of pinene with sulfuric acid and
    toluene sulfonic acid at temperatures of about
    30 to 40 C., the step of including in the reaction

    are the oil-soluble products, as distinguished 50 mixture a small quantity of mahogany acids as
    from green acids, which are water-soluble prod
    a reaction promoter.
    ucts produced in such treatment. The green
    3. In the production of terpin hydrate by the
    acids are not effective in promoting the reaction
    treatment of pinene with dilute acid at tempera
    of pinene to terpin hydrate.
    tures of about 30 to 40 C., the step of including
    The high reaction rates and high yields ob 55 in the reaction mixture 2 to 5% of toluene sul

    2,481,845

    3
    fonic acid as a. reaction promoter, based on the

    total aqueous material.


    4. In the production of terpin hydrate by the
    treatment of pinene with sulfuric acid and
    toluene sulfonic acid at temperatures of about

    '7. The process of claim 2 in which the quantity


    of mahogany acids is of the approximate order
    of 1% to 10% of the amount of pinene treated.
    ROBERT GARDNER KING.

    REFERFZWE QIEQ

    30 to 40f} Cr, the stepofincludinjgyin the reaction


    mixtur 72 to

    ofitoliiene s'iilfonieaciiibased

    on the total aqueous material.

    5. In the production of terpin hydrate by the

    treatment of pinene with dilute sulfuric acid at 10


    temperatures of about 30 toi?h {3.3 thestep of '
    including in the reaction mixture a quantity'of
    mahogany acids up to about 5% of theamount

    The following rererneesa? or record in the


    ?le of this patent:
    STATES PATENTS
    Number
    2,178,349

    Name
    Date
    She?igld ________ __ Oct. 31, 1939

    2,295,105

    Weisjsenbom ____ __ Sept. 15, 1942.

    of pinene and from 2 to 5% oftoluene suitor-lie

    ?asfsielstrom _____ __ Sept. 28, 1943'

    acid based on the total aqueousTrYnater-ial.~

    6. The process in claim 1 in which the quantity


    of mahogany acids is of the approximate creep
    of 1% to 10% of the amount of pinene treated.

    REFERENCES

    , 'Kiinura, JounSoc. Chem. Ind, Japan, vol. 40,

    July 1e37,.page 237B.

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