Document:

Exhibit 10.90

Exhibit 10.90

THIS WARRANT IS SUBJECT TO RESTRICTIONS ON TRANSFER SET FORTH IN 

THIS COMMON STOCK PURCHASE WARRANT.

SYNTROLEUM CORPORATION

COMMON STOCK PURCHASE WARRANT

December 30, 2009

This Warrant (the “Warrant”) entitles Fletcher International, Ltd., a company domiciled in Bermuda
(including any successors or assigns, the “Holder”), for value received, to purchase from
SYNTROLEUM CORPORATION, a Delaware corporation (the “Company”), during the Warrant Term (as defined
below) and subject to the terms and conditions set forth herein, all or any portion of the Warrant
Shares (as defined below) at the Exercise Price (as defined below). This Warrant is issued subject
to the following terms and conditions:

1. Warrants.

1.1 General. This Warrant has been issued pursuant to that certain Securities
Purchase Agreement, dated October 14, 2009, as it may be amended from time to time, by and among
the Company and the Holder (the “Securities Purchase Agreement”), and are subject to the terms and
conditions thereof. Unless otherwise defined herein, capitalized terms used herein shall have the
meanings set forth in the Securities Purchase Agreement. A copy of the Securities Purchase
Agreement may be obtained at no cost by the Holder upon written request to the Secretary of the
Company at the principal executive offices of the Company.

1.2 Warrant Amount. This Warrant shall entitle the Holder to purchase up to 2,365,362
shares of newly-issued Common Stock (the “Warrant Shares”).

1.3 Exercise Price. The per share exercise price for the Warrant Shares shall be
$3.3029 (the “Exercise Price”).

1.4 Warrant Term. Subject to the limitations contained herein, the Warrant may be
exercised (in whole or in part) at any time or from time to time after the date hereof until 11:59
P.M., New York City time on the date that is six (6) years after the date hereof (the “Warrant
Term”); provided, however, that in connection with a Change of Control (as defined in the
Securities Purchase Agreement), this Warrant shall be subject to Section 3.4.

2. Exercise of Warrant. 

2.1 Method of Exercise; Payment. Subject to all of the terms and conditions hereof
and the limitations set forth in Sections 2.6 and 2.7, the Holder shall
notify the Company prior to any exercise of this Warrant, in whole or in part, with respect to any
Warrant Shares, during the Warrant Term, by delivering a notice of intent to exercise substantially
in the form attached hereto, three (3) Business Days prior to the exercise date set forth therein;
provided that any such notice must be delivered to the Company at least three (3) Business Days
prior to the expiration of the Warrant Term. Upon the exercise date set forth in the applicable
notice, subject to all of the terms and conditions hereof and the limitations set forth in
Sections 2.6 and 2.7, the Holder shall (1) surrender this Warrant to the
Company at its principal office, (2) deliver to the Company a subscription substantially in the
form attached hereto, and (3) send a (a) wire transfer of immediately available funds or (b)
certified or official bank check

 

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 payable to the order of the Company, in each case in the amount obtained by multiplying (i)
the number of Warrant Shares for which the Warrant is being exercised, as designated in such notice
and subscription, by (ii) the Exercise Price. Thereupon, the Holder shall be entitled to receive
the applicable number of duly authorized, validly issued, fully paid and nonassessable Warrant
Shares. Notwithstanding the foregoing, each exercise of the Warrant by the Holder must be for at
least 1,000,000 Warrant Shares; provided, however, that the Warrant may be exercised for a lower
number of Warrant Shares if such exercise is for all remaining Warrant Shares subject to the
Warrant.

2.2 Delivery of Stock Certificates on Exercise. Upon the exercise date of this
Warrant, unless otherwise mutually agreed upon by the parties, to the extent reasonably
practicable, the Company, at its expense, and in accordance with applicable securities laws, shall
deliver the number of Warrant Shares purchased by the Holder on such exercise to Holder’s account
via The Depository Trust Company’s Deposit/Withdrawal at Custodian (DWAC) system using the account
information provided by Holder in its notice of intent to exercise.

2.3 Shares To Be Fully Paid and Nonassessable. All Warrant Shares issued upon the
exercise of this Warrant shall be duly authorized, validly issued, fully paid and nonassessable,
free of all liens, taxes, charges and other encumbrances or restrictions on sale (other than those
set forth herein).

2.4 Payment of Taxes and Expenses. The Company shall pay any recording, filing, stamp
or similar tax which may be payable in respect of any transfer involved in the issuance of, and the
preparation and, as applicable, the delivery of certificates representing or the delivery via The
Depository Trust Company’s Deposit/Withdrawal at Custodian (DWAC) system of, (i) any Warrant Shares
purchased upon exercise of this Warrant and/or (ii) new or replacement warrants in the Holder’s
name or the name of any transferee of all or any portion of this Warrant.

2.5 Cooperation with Filings. The Company shall assist and cooperate with the Holder
if the Holder is required to make any governmental or regulatory filings or obtain any governmental
or regulatory approvals prior to or in connection with any exercise of this Warrant (including,
without limitation, making any filings required to be made by the Company).

2.6 Limitation on Exercise. This Warrant shall not be exercisable (i) to the extent
that, on or immediately after exercise, the representations in Section 3.2(d) of the Securities
Purchase Agreement would be untrue, and (ii) unless and until such representations are made and the
Tax Covenants, as applicable, are performed.

2.7 Limitation on Exercise by Transferees. In the event this Warrant is transferred
in accordance with Section 5, this Warrant shall not be exercisable (i) to the extent that,
on or immediately after exercise, the representations in Section 3.2(d) of the Securities Purchase
Agreement would be untrue with respect to the person exercising the Warrant and such person’s Tax
Affiliates, and (ii) unless and until the person exercising the Warrant makes such representations
and performs the Tax Covenants. For purposes of this Section 2.7, references to the
Purchaser and its Tax Affiliates in Section 3.2(d) of the Securities Purchase Agreement and in the
Tax Covenants shall be treated as referring to the person exercising the Warrant and such person’s
Tax Affiliates.

2.8 The provisions of Section 4.2(g) of the Securities Purchase Agreement shall apply hereto,
to the extent relevant to the provisions hereof, substituting “Holder” for “Purchaser” therein.

 

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3. Adjustment of Exercise Price and Warrant Shares. The Exercise Price and the number
of Warrant Shares shall be subject to adjustment from time to time upon the happening of certain
events as described in this Section 3.

3.1 Subdivision or Combination of Stock. If at any time or from time to time after
the date hereof, the Company shall subdivide (by way of stock dividend, stock split or otherwise)
its outstanding shares of Common Stock, the Exercise Price in effect immediately prior to such
subdivision shall be reduced proportionately and the number of Warrant Shares (calculated to the
nearest whole share) shall be increased proportionately, and conversely, in the event the
outstanding shares of Common Stock shall be combined (whether by stock combination, reverse stock
split or otherwise) into a smaller number of shares, the Exercise Price in effect immediately prior
to such combination shall be increased proportionately and the number of Warrant Shares (calculated
to the nearest whole share) shall be decreased proportionately. The Exercise Price and the number
of Warrant Shares, as so adjusted, shall be readjusted in the same manner upon the happening of any
successive event or events described in this Section 3.1.

3.2 Adjustment for Stock Dividends. If at any time after the date hereof, the Company
shall declare a dividend or make any other distribution upon any class or series of stock of the
Company payable in shares of Common Stock, the Exercise Price in effect immediately prior to such
declaration or distribution shall be reduced proportionately and the number of Warrant Shares
(calculated to the nearest whole share) shall be increased proportionately, to reflect the issuance
of any shares of Common Stock, issuable in payment of such dividend or distribution. The Exercise
Price and the number of Warrant Shares, as so adjusted, shall be readjusted in the same manner upon
the happening of any successive event or events described in this Section 3.2.

3.3 Adjustments for Reclassifications. If the Common Stock issuable upon the exercise
of this Warrant shall be changed into the same or a different number of shares of any class(es) or
series of stock and/or the right to receive property, whether by reclassification or otherwise
(other than an adjustment under Sections 3.1 and 3.2 or a merger, consolidation, or
sale of assets provided for under Section 3.4), then and in each such event, the Holder
hereof shall have the right thereafter to convert each Warrant Share into the kind and amount of
shares of stock and other securities and property receivable upon such reclassification, or other
change by holders of the number of shares of Common Stock into which such Warrant Shares would have
been convertible immediately prior to such reclassification or change, all subject to successive
adjustments thereafter from time to time pursuant to and in accordance with, the provisions of this
Section 3.

3.4 Adjustments for Merger or Consolidation.

(a) If during the Warrant Term a Change of Control or plan or proposal with respect thereto is
publicly announced or occurs, and the Acquiring Person (as defined in the Securities Purchase
Agreement) (or its direct or indirect parent entity) does not have a class of common equity
securities listed or admitted for trading on any securities exchange or over-the-counter or other
organized market, whether U.S. or not, then this Warrant shall terminate upon the effective date of
a Change of Control; provided that between the date such Change of Control is announced and the
effective date of the Change of Control, but not thereafter, the Holder shall have the right to
submit to the Company an exercise notice (which exercise notice may, at the Holder’s option,
specify that the exercise and payment of the Exercise Price shall occur simultaneously with, and be
contingent upon, the occurrence of the Change of Control) in accordance with the terms and
conditions of this Warrant; provided, however, that so long as the Company has provided the Holder
with at least five (5) Business Days (as defined in the Securities Purchase Agreement) advance
written notice of the effective date for the Change of Control, the
Company shall not be required to postpone such closing date in order to facilitate the closing of
the exercise.

 

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(b) If during the Warrant Term a Change of Control or plan or proposal with respect thereto is
publicly announced or occurs, and the Acquiring Person (or its direct or indirect parent entity)
has a class of common equity securities listed or admitted for trading on any securities exchange
or over-the-counter or other organized market, whether U.S. or not, then:

(i) Between the date such Change of Control is announced and the effective date of the Change
of Control, the Holder shall have the right to submit to the Company an exercise notice (which
exercise notice may, at the Holder’s option, specify that the exercise and payment of the Exercise
Price shall occur simultaneously with, and be contingent upon, the occurrence of the Change of
Control) in accordance with the terms and conditions of this Warrant; provided, however, that so
long as the Company has provided the Holder with at least five (5) Business Days advance written
notice of the effective date for the Change of Control, the Company shall not be required to
postpone such closing date in order to facilitate the closing of the exercise;

(ii) The Company shall not enter into an agreement with the Acquiring Person resulting in such
Change of Control unless such agreement expressly obligates the Acquiring Person to assume all of
the Company’s obligations under this Warrant; and

(iii) In the event that any portion of this Warrant remains unexercised upon consummation of
the Change of Control, the Holder shall thereafter automatically have equivalent rights with
respect to the Acquiring Person, and from and after the effective date of the Change of Control and
regardless of whether the Acquiring Person expressly assumes the Company’s obligations:

(A) all references to the Company in this Warrant shall be references to the Acquiring Person,

(B) all references to Common Stock in this Warrant shall be references to the securities for
which the Common Stock are exchanged in the Change of Control (or if none, the most widely-held
class of common equity securities of the Acquiring Person),

(C) the Exercise Price shall be adjusted, employing the methodology set forth in the
example(s) on Annex I hereto, to equal the Exercise Price as in effect immediately prior to
the Change of Control multiplied by a fraction, (1) the numerator of which is the volume-weighted
average price, calculated to the nearest ten thousandth (i.e., four decimal places (.xxxx)), of the
securities for which Common Stock is exchanged in the Change of Control (or if none, the most
widely-held class of voting common equity securities of the Acquiring Person), and (2) the
denominator of which is the Daily Market Price of the Company, in the case of (1) and (2)
determined as of the Business Day immediately preceding and excluding the date on which the Change
of Control is consummated. For purposes of this Warrant, “Daily Market Price” has the meaning
given in the Securities Purchase Agreement, substituting references to the “Holder” for the
“Purchaser,” and

(D) the number of Warrant Shares shall be adjusted, employing the methodology set forth in the
example(s) on Annex I hereto, to equal the product of the number of Warrant Shares in
effect immediately prior to the Change of Control multiplied by a fraction, (1) the numerator of
which is the Daily Market Price of the Company, and (2) the denominator of which is the
volume-weighted average price, calculated to the nearest ten thousandth (i.e., four decimal places
(.xxxx)), of the securities for which Common Stock is exchanged in the Change of Control (or if
none, the most widely-held class of voting common equity securities of the Acquiring Person), in
the case of (1) and (2)
determined as of the Business Day immediately preceding and excluding the date on which the Change
of Control is consummated.

 

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3.5 Minimum Adjustment of Exercise Price. If the amount of any adjustment of the
Exercise Price required pursuant to this Section 3 would be less than one-tenth (1/10) of
one percent (1%) of the Exercise Price in effect at the time such adjustment is otherwise so
required to be made, such amount shall be carried forward and adjustment with respect thereto made
at the time of and together with any subsequent adjustment which, together with such amount and any
other amount or amounts so carried forward, shall aggregate at least one tenth (1/10) of one
percent (1%) of such Exercise Price.

3.6 Certificate as to Adjustments. Upon the occurrence of each adjustment or
readjustment of the Exercise Price and number of Warrant Shares pursuant to this Section 3,
this Warrant shall, without any action on the part of the Holder, be adjusted in accordance with
this Section 3, and the Company, at its expense, promptly shall compute such adjustment or
readjustment in accordance with the terms hereof and prepare and furnish to the Holder a
certificate setting forth such adjustment or readjustment, showing in detail the facts upon which
such adjustment or readjustment is based. The Company will forthwith send a copy of each such
certificate to the Holder in accordance with Section 7.4 below.

4. Notices of Record Date. Upon (a) any establishment by the Company of a record date
of the holders of any class of securities for the purpose of determining the holders thereof who
are entitled to receive any dividend or other distribution, or right or option to acquire
securities of the Company, or any other right, or (b) any capital reorganization, reclassification,
recapitalization, merger or consolidation of the Company with or into any other Person, any
transfer of all or substantially all the assets of the Company, or any voluntary or involuntary
dissolution, liquidation or winding up of the Company, or the sale, in a single transaction, of a
majority of the Company’s voting stock (whether newly issued, or from treasury, or previously
issued and then outstanding, or any combination thereof), the Company shall mail to the Holder at
least ten (10) Business Days, or such longer period as may be required by law, prior to the record
date specified therein and at least ten (10) Business Days prior to the date specified in clause
(ii) or (iii) hereof, a notice specifying (i) the date established as the record date for the
purpose of such dividend, distribution, option or right and a description of such dividend,
distribution, option or right, (ii) the date on which any such reorganization, reclassification,
transfer, consolidation, merger, dissolution, liquidation or winding up, or sale is expected to
become effective and (iii) the date, if any, fixed as to when the holders of record of Common Stock
shall be entitled to exchange their shares of Common Stock for securities or other property
deliverable upon such reorganization, reclassification, transfer, consolidation, merger,
dissolution, liquidation or winding up. Subject to the other limitations on exercise contained in
this Warrant, nothing in this Section 4 shall prohibit the Holder from exercising this
Warrant during the ten (10) Business Day period commencing on the date of such notice.

5. Transfer Provisions, etc.

5.1 Limitations on Transfer. None of the Holder, or any subsequent successor,
transferee or assign, shall sell or otherwise transfer this Warrant to any Person unless and until
(1) the transferee makes the representations in Section 3.2(d) of the Securities Purchase
Agreement, agrees to perform and, to the extent then applicable, performs the Tax Covenants and (2)
the transferor and the transferee, each represent in writing, under penalty of perjury, that it
does not have a principal purpose of avoiding or ameliorating the impact of an ownership change
within the meaning of Treasury Regulation Section 1.382-4(d) related to the transfer of the
Warrant. For purposes of this Section 5.1, references to the Purchaser and its Tax
Affiliates in Section 3.2(d) and in the Tax Covenants of the Securities Purchase Agreement shall be
treated as referring to the transferee and its Tax Affiliates. Upon any transfer by the
Holder, or any subsequent successor, transferee or assign, such Person shall deliver to the
Company the Notice of Transfer, in the form attached hereto.

 

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5.2 Warrant Register. The Company shall keep at its principal office a register for
the registration, and registration of transfers, of the Warrants. The name and address of each
Holder of one or more of the Warrants, each transfer thereof and the name and address of each
transferee of one or more of the Warrants shall be registered in such register.

6. Lost, Stolen or Destroyed Warrant. Upon receipt by the Company of evidence
satisfactory to it of loss, theft, destruction or mutilation of this Warrant and, in the case of
loss, theft or destruction, on delivery of a customary affidavit of the Holder and customary
unsecured indemnity agreement, or, in the case of mutilation, upon surrender of this Warrant, the
Company at its expense will execute and deliver, or will instruct its transfer agent to execute and
deliver, a new Warrant of like tenor and date and representing the same rights represented by such
lost, stolen, destroyed or mutilated warrant and any such lost, stolen, mutilated or destroyed
Warrant thereupon shall become void.

7. General.

7.1 Authorized Shares, Reservation of Shares for Issuance. At all times while this
Warrant is outstanding, the Company shall maintain its corporate authority to issue, and shall have
authorized and reserved for issuance upon exercise of this Warrant, such number of shares of Common
Stock, and any other capital stock or other securities as shall be sufficient to perform its
obligations under this Warrant (after giving effect to any and all adjustments to the number and
kind of Warrant Shares purchasable upon exercise of this Warrant).

7.2 No Impairment. The Company will not, by amendment of its certificate of
incorporation or through any reorganization, transfer of assets, consolidation, merger,
dissolution, issuance or sale of securities, sale or other transfer of any of its assets or
properties, or any other voluntary action, avoid or seek to avoid the observance or performance of
any of the terms of this Warrant, but will at all times in good faith assist in the carrying out of
all such terms and in the taking of all such action as may be necessary or appropriate in order to
protect the rights of the Holder hereunder against impairment. Without limiting the generality of
the foregoing, the Company (a) will not increase the par value of any shares of Common Stock
receivable upon the exercise of this Warrant above the amount payable therefor on such exercise,
and (b) will take all action that may be necessary or appropriate in order that the Company may
validly and legally issue fully paid and nonassessable shares of Common Stock upon the exercise of
this Warrant.

7.3 No Rights as Stockholder. Except as provided herein, the Holder shall not be
entitled to vote or to receive dividends or to be deemed the holder of Common Stock that may at any
time be issuable upon exercise of this Warrant for any purpose whatsoever, nor shall anything
contained herein be construed to confer upon the Holder any of the rights of a stockholder of the
Company or any right to vote for the election of directors or upon any matter submitted to
stockholders at any meeting thereof, or to give or withhold consent to any corporate action
(whether upon any recapitalization, issuance or reclassification of stock, change of par value or
change of stock to no par value, consolidation, merger or conveyance or otherwise), or to receive
notice of meetings (except to the extent otherwise provided in this Warrant), or to receive
dividends or subscription rights, until the Holder shall have exercised this Warrant and been
issued Warrant Shares in accordance with the provisions hereof and continues to hold Warrant
Shares.

 

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7.4 Notices. Any notices, reports or other correspondence (hereinafter collectively
referred to as “correspondence”) required or permitted to be given hereunder shall be sent by
postage
prepaid first class mail, overnight courier or facsimile transmission, or delivered by hand to
the party to whom such correspondence is required or permitted to be given hereunder. The date of
giving any notice shall be the date of its actual receipt.

(a) All correspondence to the Company shall be addressed as follows:

Syntroleum Corporation.

5416 South Yale, Suite 400

Tulsa, Oklahoma 74135

Attn: Principal Financial Officer

Facsimile: (918) 592-7900

with a copy to:

Syntroleum Corporation

5416 South Yale, Suite 400

Tulsa, Oklahoma 74135

Attention: Chief Executive Officer

Facsimile: (918) 592-7979

(b) All correspondence to the Holder shall be addressed to the Holder at its address appearing
in the books maintained by the Company.

8. Amendment and Waiver. No failure or delay of the Holder in exercising any power or
right hereunder shall operate as a waiver thereof, nor shall any single or partial exercise of any
such right or power, or any abandonment or discontinuance of steps to enforce such a right or
power, preclude any other or further exercise thereof or the exercise of any other right or power.
The rights and remedies of the Holder are cumulative and not exclusive of any rights or remedies
which it would otherwise have. Any term of this Warrant may be amended or waived upon the written
consent of the Company and the Holder.

9. Governing Law. All questions concerning the construction, validity, enforcement
and interpretation of the Warrant shall be governed by and construed and enforced in accordance
with the internal laws of the State of Delaware, without regard to the principles of conflicts of
law thereof.

10. Covenants To Bind Successor and Assigns. Except as expressly provided otherwise,
all covenants, stipulations, promises and agreements in this Warrant contained by or on behalf of
the Company shall bind its successors and assigns, whether so expressed or not.

11. Severability. In case any one or more of the provisions contained in this Warrant
shall be invalid, illegal or unenforceable in any respect, the validity, legality and
enforceability of the remaining provisions contained herein shall not in any way be affected or
impaired thereby. The parties shall endeavor in good faith negotiations to replace the invalid,
illegal or unenforceable provisions with valid provisions the economic effect of which comes as
close as possible to that of the invalid, illegal or unenforceable provisions.

 

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12. Construction. The definitions of this Warrant shall apply equally to both the
singular and the plural forms of the terms defined. Wherever the context may require, any pronoun
shall include the corresponding masculine, feminine and neuter forms. The section and paragraph
headings used herein are for convenience of reference only, are not part of this Warrant and are
not to affect the construction of or be taken into consideration in interpreting this Warrant.

[Signature Page to Follow]

 

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In Witness Whereof, the Company has executed this Common Stock Purchase Warrant as of
the date first written above.

	 	 	 	 	 
	 	COMPANY:

SYNTROLEUM CORPORATION

 	 
	 	By:  	/s/ Edward G. Roth
 	 
	 	 	Name:  	Edward G. Roth 	 
	 	 	Title:  	President/Chief Executive Officer 	 

 

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ANNEX I

	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 	 	 	 	 	 	Case 1: Acquiror	 	 	Case 2: Acquiror	 	 	Case 3: Acquiror	 
	 	 	 	 	 	 	Price Above SYNM	 	 	Price Below SYNM	 	 	Price Equals SYNM	 
	 	 	Units	 	 	Price	 	 	Price	 	 	Price	 
	Example Change of Control Calculations
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	(A): Acquiror share price daily VWAP on day prior to Closing
	 	$/share	 	$	25.0000	 	 	$	2.0000	 	 	$	5.0000	 
	(B): Daily Market Price of Syntroleum on day prior to Closing
	 	$/share	 	$	5.0000	 	 	$	5.0000	 	 	$	5.0000	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Adjusted Exercise Price
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Exercise Price in Effect Prior to Change of Control
	 	$/share	 	$	3.3750	 	 	$	3.3750	 	 	$	3.3750	 
	Multiplied by fraction (A) divided by (B)
	 	 	 	 	 	 	5.0000	 	 	 	0.4000	 	 	 	1.0000	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 
	Adjusted Exercise Price
	 	$/share	 	$	16.8750	 	 	$	1.3500	 	 	$	3.3750	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Adjusted Warrants Outstanding
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Fletcher Warrants in Effect Prior to Change of Control
	 	000 shares	 	 	5,556	 	 	 	5,556	 	 	 	5,556	 
	Multiplied by fraction (B) divided by (A)
	 	 	 	 	 	 	0.2000	 	 	 	2.5000	 	 	 	1.0000	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 
	Adjusted Warrants Outstanding
	 	000 shares	 	 	1,111	 	 	 	13,890	 	 	 	5,556	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Warrant Exercise Consideration Post Acquisition
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	New Exercise Price X
	 	$/share	 	$	16.8750	 	 	$	1.3500	 	 	$	3.3750	 
	New Warrants Outstanding
	 	000 shares	 	 	1,111	 	 	 	13,890	 	 	 	5,556	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 
	Exercise Consideration Post Acquisition
	 	 	000 $	 	 	$	18,748.12	**	 	$	18,751.50	 	 	$	18,751.50	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Equals
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Warrant Exercise Consideration Pre-Acquisition
	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 	 
	Original Exercise Price X
	 	$/share	 	$	3.3750	 	 	$	3.3750	 	 	$	3.3750	 
	Original Warrants
	 	000 shares	 	 	5,556	 	 	 	5,556	 	 	 	5,556	 
	 
	 	 	 	 	 	 	 	 	 	 	 	 	 
	Exercise Consideration Pre Acquisition
	 	 	000 $	 	 	$	18,751.50	 	 	$	18,751.50	 	 	$	18,751.50	 

	 	 	 
	**	 	The variation from “Exercise Consideration Pre Acquisition” is due to rounding to the nearest
whole share in computing the New Warrants Outstanding. 

 

 

 

NOTICE OF INTENT TO EXERCISE

	To: 	 	 Syntroleum Corporation.

5416 South Yale, Suite 400

Tulsa, Oklahoma 74135

The undersigned hereby irrevocably elects to exercise the right of purchase represented by the
attached Warrant for, and to exercise thereunder,                      shares of Common Stock, of Syntroleum
Corporation, a Delaware corporation (the “Company”), at a per share exercise price equal to $                    .

Exercise Date:                                                              (3 Business Days after the date of this Notice)

Upon the Exercise Date, to the extent reasonably practicable, please deliver the shares of
Common Stock described above to the undersigned’s account via The Depository Trust Company’s
Deposit/Withdrawal at Custodian (DWAC) system using the following account information:

 

 

 

 

If said number of shares of Common Stock shall not be all the shares of Common Stock issuable upon
exercise of the attached Warrant, a new Warrant is to be issued in the name of the undersigned for
the remaining balance of such shares of Common Stock.

	 	 	 
	 

	 	Holder
	 
	 	 
	Dated:                     ,           
	 	 
	 

	 	 
	 

	 	Signature

 

 

 

SUBSCRIPTION

	To: 	 	 Syntroleum Corporation.

5416 South Yale, Suite 400

Tulsa, Oklahoma 74135

The undersigned hereby irrevocably elects to exercise the right of purchase represented by the
attached Warrant for, and to exercise thereunder,                      shares of Common Stock, of Syntroleum
Corporation, a Delaware corporation (the “Company”), at a per share exercise price equal to $                    ,
and accordingly tenders herewith an aggregate payment of $                    , representing the aggregate
purchase price for such shares based on the price(s) per share provided for in such Warrant. Such
payment is being made in accordance with Section 2.1 of the attached Warrant.

The undersigned hereby represents and warrants as follows:

(a) the undersigned does not by the exercise of the Warrant pursuant to this notice violate
Section 2.6 and/or Section 2.7 of the Warrant;

(b) the undersigned and its “Tax Affiliates” (defined as any Person in which the undersigned
directly or indirectly through one or more intermediaries, owns any equity interest) do not and
will not own, immediately before or immediately after this exercise, more than 4.95% of the shares
of Common Stock of the Company outstanding as of the date hereof. For purposes of the foregoing
sentence and subsection (c) below: (A) ownership of Common Stock shall include any long derivative
or synthetic position and any other stock (as defined in Temporary Treasury Regulation Section
1.382-2T(f)(18) or any successor provision) of the Company held by the undersigned or its Tax
Affiliates; (B) notwithstanding the foregoing clause (A), ownership of Common Stock shall not
include any Common Stock which may be acquired pursuant to Section 2.1(b) of the Securities
Purchase Agreement or by exercise of this Warrant (other than this exercise) or any other Warrants
issued pursuant to the Securities Purchase Agreement until such Common Stock is purchased and
issued; (C) any short actual, synthetic or derivative positions shall not decrease the amount of
Common Stock that the undersigned and its Tax Affiliates are treated as owning, and (D) for
purposes of calculating the percentage ownership interest of the undersigned and its Tax Affiliates
as of a particular date, the aggregate number of shares of Common Stock outstanding shall be the
number of outstanding shares of Common Stock of the Company most recently reported prior to such
date by the Company in a filing with the SEC, provided, however, that if at least twenty (20)
Business Days prior to this exercise, the Company informs the undersigned in writing that it has
redeemed shares of its Common Stock and provides the undersigned with the number of outstanding
shares of Common Stock following such redemption which the undersigned can rely upon for this
purpose, the undersigned will use such revised number of outstanding shares instead, unless and
until further updated by a subsequent SEC filing and/or Company notice pursuant hereto; and

(c) the undersigned has delivered to the Company the Affidavits described in Section 4.2(d) of
the Securities Purchase Agreement and has performed all the Tax Covenants set forth in the
Securities Purchase Agreement, applying such Section 4.2(d) and the Tax Covenants as if the
undersigned were the Purchaser referenced therein.

[Signature Page to Follow]

 

 

 

	 	 	 
	 

	 	Holder
	 
	 	 
	Dated:                     ,           
	 	 
	 

	 	 
	 

	 	Signature

Syntroleum Corporation hereby acknowledges receipt of this Subscription and authorizes issuance of
the shares of Common Stock described above.

	 	 	 	 	 
	Syntroleum Corporation

 	 	 
	By:  	 	 	 
	 	Title: 	  	 	 
	 	Date:	  	 	 
	 

 

 

 

	 	 	 	 	 

NOTICE OF TRANSFER 

	To: 	 	 Syntroleum Corporation.

5416 South Yale, Suite 400

Tulsa, Oklahoma 74135

For value received, the undersigned hereby sells, assigns and transfers unto
                                         (the “Transferee”) [the attached Warrant] [                     Warrant Shares (the
“Transferred Warrant Shares”)], together with all right, title and interest therein, and does
hereby irrevocably constitute and appoint                      attorney to transfer said [Warrant]
[Transferred Warrant Shares] on the books of Syntroleum Corporation, a Delaware corporation (the
“Company”), with full power of substitution in the premises.

If not all of the attached Warrant is to be so transferred, a new Warrant is to be issued in
the name of the undersigned for the balance of said Warrant.

The undersigned transferor hereby represents and warrants as follows:

(a) the transfer is in compliance with the requirements and restrictions set forth in 4.2 of
the Securities Purchase Agreement, applied as if the undersigned transferor were the Purchaser
referenced in such provisions; and

(b) it does not have a principal purpose of avoiding or ameliorating the impact of an
ownership change within the meaning of Treasury Regulation Section 1.382-4(d) related to the
transfer of the Warrant.

The Transferee hereby represents and warrants as follows:

(a) the Transferee and its “Tax Affiliates” (defined as any Person in which the Transferee,
directly or indirectly through one or more intermediaries, owns any equity interest) do not and
will not own, immediately before or immediately after this transfer, more than 4.95% of the shares
of Common Stock of the Company outstanding as of the date hereof. For purposes of the foregoing
sentence and subsection (b) below: (A) ownership of Common Stock shall include any long derivative
or synthetic position and any other stock (as defined in Temporary Treasury Regulation Section
1.382-2T(f)(18) or any successor provision) of the Company held by the Transferee or its Tax
Affiliates; (B) notwithstanding the foregoing clause (A), ownership of Common Stock shall not
include any Common Stock which may be acquired pursuant to Section 2.1(b) of the Securities
Purchase Agreement or by exercise of this Warrant or any other Warrants issued pursuant to the
Securities Purchase Agreement until such Common Stock is purchased and issued; (C) any short
actual, synthetic or derivative positions shall not decrease the amount of Common Stock that the
Transferee and its Tax Affiliates are treated as owning, and (D) for purposes of calculating the
percentage ownership interest of the Transferee and its Tax Affiliates as of a particular date, the
aggregate number of shares of Common Stock outstanding shall be the number of outstanding shares of
Common Stock of the Company most recently reported prior to such date by the Company in a filing
with the SEC, provided, however, that if at least twenty (20) business days prior to the transfer,
the Company informs the Transferee in writing that it has redeemed shares of its Common Stock and
provides the Transferee with the number of outstanding shares of Common Stock following such
redemption which the Transferee can rely upon for this purpose, the Transferee will use such
revised number of outstanding shares instead, unless and until further updated by a subsequent SEC
filing and/or Company notice pursuant hereto.

 

 

 

(b) the Transferee has delivered to the Company an affidavit, attesting that immediately
before and immediately after the transfer of this Warrant the Transferee and its Tax Affiliates
(treated in the aggregate) are not a “5-percent shareholder” (as the term is defined under Section
382 of the Code treating, for this purpose, the Transferee and its Tax Affiliates in the aggregate
as one individual) based on the number of outstanding shares determined in the manner provided in
subsection (a) above.

(c) it does not have a principal purpose of the transfer is not to avoid or ameliorate the
impact of an ownership change within the meaning of Treasury Regulation Section 1.382-4(d) related
to the transfer of the Warrant;

(d) that it has performed and will continue to perform the Tax Covenants, applied as if the
Transferee were the Purchaser referenced therein;

(e) the Transferee shall be subject to the terms and conditions of the Warrant, as if it were
the original Holder thereunder, and Sections 4.2(a), (b), (c), (d), and (f) of the Securities
Purchase Agreement, as if it were the Purchaser referenced thereunder, with respect to any exercise
or transfer of the Warrant; and

(f) the Transferee understands and acknowledges that the transfer is dependent upon the
representations and warranties of the Transferee being true and correct and that the Company shall
be entitled to rely on and shall be the beneficiary of these representations and warranties.

[Signature Page to Follow]

 

 

 

	 	 	 
	 

	 	Holder
	 
	 	 
	Dated:                     ,           
	 	 
	 

	 	 
	 

	 	Signature
	 
	 	 
	Acknowledged and Agreed:
	 	 
	 
	 	 
	Transferee
	 	 
	 
	 	 
	 
	 	 
	 	 
	 
	Signature
	 	 

Syntroleum Corporation hereby acknowledges receipt of this Notice of Transfer.

	 	 	 	 	 
	Syntroleum Corporation

 	 	 
	By:  	 	 	 
	 	Title: 	  	 	 
	 	Date:exv4w1

Exhibit 4.1

SECOND AMENDMENT TO AMENDED AND RESTATED

SENIOR PREFERRED STOCK PURCHASE AGREEMENT

     SECOND AMENDMENT dated as of December 24, 2009, to the AMENDED AND RESTATED SENIOR
PREFERRED STOCK PURCHASE AGREEMENT dated as of September 26, 2008, between the UNITED STATES
DEPARTMENT OF THE TREASURY (“Purchaser”), and
FEDERAL NATIONAL MORTGAGE ASSOCIATION (“Seller”),
acting through the Federal Housing Finance Agency (the “Agency”) as its duly appointed conservator
(the Agency in such capacity, “Conservator”).

Background

     A. Purchaser and Seller have heretofore entered into the Amended and Restated Senior
Preferred Stock Purchase Agreement dated as of September 26, 2008 (the “Amended and Restated
Agreement”).

     B. In the Amended and Restated Agreement, Purchaser committed itself to provide to Seller, on
the terms and conditions provided in the Amended and Restated Agreement, immediately available
funds in an amount as determined from time to time as provided in the Amended and Restated
Agreement, but in no event in an aggregate amount exceeding $100,000,000,000.

     C. Purchaser and Seller have heretofore entered into the Amendment dated as of May 6, 2009, to
the Amended and Restated Agreement (the “First Amendment”).

     D. In the First Amendment, Purchaser increased to $200,000,000,000 the maximum aggregate
amount permitted to be provided to Seller under the Amended and Restated Agreement, and amended the
terms of the Amended and Restated Agreement in certain other respects.

     E. Purchaser and Seller are each authorized to enter into this Second Amendment to the Amended
and Restated Agreement (“this Second Amendment”) (i) modifying the Treasury’s funding commitment to
Seller to provide it with additional funding in amounts not to exceed the new formulaic maximum
amount specified herein, and (ii) amending the terms of the Amended and Restated Agreement, as
previously amended, in certain other respects.

     THEREFORE, for and in consideration of the mutual agreements herein contained and for other
good and valuable consideration, the receipt and sufficiency of which is hereby acknowledged,
Purchaser and Seller agree as follows:

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Terms and Conditions

1. Definitions.

     Capitalized terms used and not defined in this Amendment shall have the respective
meanings given such terms in the Amended and Restated Agreement, as amended by the First Amendment
(the Amended and Restated Agreement, as amended by the First Amendment, being the “Existing
Agreement”).

2. Amendment to Section 1 (Relating to Definition of “Indebtedness”).

     The definition of “Indebtedness” in Section 1 of the Existing Agreement is hereby
amended to read as follows:

     “Indebtedness” of any Person means, for purposes of Section 5.5 only, without
duplication, (a) all obligations of such Person for money borrowed by such Person, (b)
all obligations of such Person evidenced by bonds, debentures, notes or similar
instruments, (c) all obligations of such Person under conditional sale or other title
retention agreements relating to property or assets purchased by such Person, (d) all
obligations of such Person issued or assumed as the deferred purchase price of
property or services, other than trade accounts payable, (e) all Capital Lease
Obligations of such Person, (f) obligations, whether contingent or liquidated, in
respect of letters of credit (including standby and commercial), bankers’ and similar
instruments, and (g) any obligation of such Person, contingent or otherwise,
guaranteeing or having the economic effect of guaranteeing and Indebtedness of the
types set forth in clauses (a) through (f) payable by another Person other than
Mortgage Guarantee Obligations (and, for the avoidance of doubt, without giving effect
to any change that may be made hereafter in respect of Statement of Financial
Accounting Standards No. 140,166, or 167, or any similar accounting standard).
Indebtedness balances or amounts shall be measured at par value for purposes of
Section 5.5 only.

3. Amendment to Section 1 (Relating to Definition of “Maximum Amount”).

     The definition of “Maximum Amount” in Section 1 of the Existing Agreement is hereby
amended to read as follows:

     “Maximum Amount” means, as of any date of determination, the greater of (a)
$200,000,000,000 (two hundred billion dollars), or (b) $200,000,000,000 plus the
cumulative total of Deficiency Amounts determined for calendar quarters in calendar
years 2010, 2011, and 2012, less any Surplus Amount determined as of December 31,
2012, and in the case of either (a) or (b), less the aggregate amount of funding under
the Commitment prior to such date.

4. Amendment to Section 1 (Relating to Definition of “Mortgage Assets”).

     The definition of “Mortgage Assets” in Section 1 of the Existing Agreement is hereby
amended to read as follows:

     “Mortgage Assets” of any Person means assets of such Person consisting of
mortgages, mortgage loans, mortgage-related securities, participation

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certificates, mortgage-backed commercial paper, obligations of real estate
mortgage investment conduits and similar assets, in each case to the extent such
assets would appear on the balance sheet of such Person in accordance with GAAP as in
effect as of the date hereof (and, for the avoidance of doubt, without giving effect
to any change that may be made hereafter in respect of Statement of Financial
Accounting Standards No. 140, 166, or 167, or any similar accounting standard).
Mortgage Asset balances or amounts shall be measured at unpaid principal balance for
purposes of Section 5.7 only.

	5.	 	Amendment to Section 1 (Adding Definition for New Defined Term “Surplus Amount”).

     Section 1 of the Existing Agreement is hereby amended by inserting after the definition of the
term “Senior Preferred Stock” the following:

     “Surplus Amount” means, as of the date of determination, the amount if any by
which (a) the total assets of Seller (such assets excluding the Commitment and any
unfunded amounts thereof) exceed (b) the total liabilities of Seller, in each case as
reflected on the balance sheet of Seller as of the applicable date set forth in the
Agreement, prepared in accordance with GAAP.

	6.	 	Amendment to Section 2.1 (Relating to the Commitment).

     Section 2.1 of the Existing Agreement is hereby amended to read as follows:

     2.1 Commitment. Purchaser hereby commits to provide to Seller, on the terms and
conditions set forth herein, immediately available funds in an amount up to but not in
excess of the Available Amount, as determined from time to time (the
“Commitment”);
provided, that in no event shall the aggregate amount funded under the
Commitment exceed the greater of (a) $200,000,000,000 (two hundred billion dollars),
or (b) $200,000,000,000 plus the cumulative total of Deficiency Amounts determined for
calendar quarters in calendar years 2010, 2011, and 2012, less any Surplus Amount
determined as of December 31, 2012. The liquidation preference of Senior Preferred
Stock shall increase in connection with draws on the Commitment, as set forth in
Section 3.3 below.

	7.	 	Amendment to Section 2.5 (Relating to Termination of Purchaser’s Obligations).

     Section 2.5 of the Existing Agreement is hereby amended to read as follows:

     2.5 Termination of Purchaser’s Obligations. Subject to earlier termination
pursuant to Section 6.7, all of Purchaser’s obligations under and in respect of the
Commitment shall terminate upon the earliest of: (a) if the Liquidation End Date shall
have occurred, (i) the payment in full of Purchaser’s obligations with respect to any
valid request for funds pursuant to Section 2.4 or (ii) if there is no Deficiency
Amount on the Liquidation End Date or if no such request pursuant to Section 2.4 has
been made, the close of business on the 15th Business Day following the determination
of the Deficiency Amount, if any, as of the Liquidation End Date; (b) the payment in
full of, defeasance of or other reasonable provision for all liabilities of Seller,
whether or not contingent, including payment of any amounts that may become payable
on, or expiry of or other provision for, all Mortgage Guarantee Obligations and
provision for

- 3 - 

 

unmatured debts; and (c) the funding by Purchaser under the Commitment of an
aggregate equal to the greater of (a) $200,000,000,000 (two hundred billion dollars),
or (b) $200,000,000,000 plus the cumulative total of Deficiency Amounts determined
for calendar quarters in calendar years 2010, 2011, and 2012, less any Surplus Amount
determined as of December 31, 2012. For avoidance of doubt, the Commitment shall not
be terminable by Purchaser solely by reason of (i) the conservatorship, receivership
or other insolvency proceeding of Seller or (ii) the Seller’s financial condition or
any adverse change in Seller’s financial condition.

	8.	 	Amendment to Section 3.2 (Relating to Periodic Commitment Fee).

     Section 3.2 of the Existing Agreement is hereby amended to read as follows:

     3.2. Periodic Commitment Fee. (a) Commencing March 31, 2011, Seller shall pay to
Purchaser quarterly, on the last day of March, June, September and December of each calendar
year (each a “Periodic Fee Date”), a periodic commitment fee (the “Periodic Commitment
Fee”). The Periodic Commitment Fee shall accrue from January 1, 2011.

     (b) The Periodic Commitment Fee is intended to fully compensate Purchaser for
the support provided by the ongoing Commitment following December 31, 2010. The
amount of the Periodic Commitment Fee shall be set not later than December 31, 2010
with respect to the ensuing five-year period, shall be reset every five years
thereafter and
shall be determined with reference to the market value of the Commitment as then in
effect. The amount of the Periodic Commitment Fee shall be mutually agreed by
Purchaser and Seller, subject to their reasonable discretion and in consultation with
the
Chairman of the Federal Reserve; provided, that Purchaser may waive the
Periodic
Commitment Fee for up to one year at a time, in its sole discretion, based on adverse
conditions in the United States mortgage market.

     (c) At the election of Seller, the Periodic Commitment Fee may be paid in cash or
by adding the amount thereof ratably to the liquidation preference of each outstanding
share of Senior Preferred Stock so that the aggregate liquidation preference of all
such
outstanding shares of Senior Preferred Stock is increased by an amount equal to the
Periodic Commitment Fee. Seller shall deliver notice of such election not later than
three
(3) Business Days prior to each Periodic Fee Date. If the Periodic Commitment Fee is
not
paid in cash by 12:00 pm (New York time) on the applicable Periodic Fee Date
(irrespective of Seller’s election pursuant to this subsection), Seller shall be deemed
to
have elected to pay the Periodic Commitment Fee by adding the amount thereof to the
liquidation preference of the Senior Preferred Stock, and the aggregate liquidation
preference of the outstanding shares of Senior Preferred Stock shall thereupon be
automatically increased, in the manner contemplated by the first sentence of this
section,
by an aggregate amount equal to the Periodic Commitment Fee then due.

	9.	 	Amendment to Section 5.7 (Relating to Owned Mortgage Assets).

     Section 5.7 of the Existing Agreement is hereby amended to read as follows:

     5.7. Mortgage Assets. Seller shall not own, as of any applicable date, Mortgage
Assets in excess of (i) on December 31, 2009, $900 billion, or (ii) on December 31 of
each year thereafter, 90.0% of the aggregate amount of Mortgage Assets that Seller was
permitted to own as of December 31 of the immediately

- 4 - 

 

	 	 	preceding calendar year; provided, that in no event shall Seller be
required under this Section 5.7 to own less than $250 billion in Mortgage Assets.
	 
	10.	 	Existing Agreement to Continue, as Amended.

        Except as expressly modified by this Second Amendment, the Existing Agreement shall
continue in full force and effect.

	11.	 	Effective Date.

        This Second Amendment shall not become effective until it has been executed by both of
Purchaser and Seller. When this Second Amendment has been so executed, it shall become effective as
of the date first above written.

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	 	FEDERAL NATIONAL MORTGAGE ASSOCIATION, by

Federal Housing Finance Agency, 

its Conservator

 	 
	 	/s/ Edward J. DeMarco
 	 
	 	Edward J. DeMarco  	 
	 	Acting Director 	 
	 
	 	UNITED STATES DEPARTMENT OF THE TREASURY

 	 
	 	/s/ Timothy F. Geithner
 	 
	 	Timothy F. Geithner  	 
	 	Secretary of the Treasury 	 
	 

- 6 -

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